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Sample records for benzoylation

  1. Benzoyl Peroxide Topical

    MedlinePlus

    ... Up® (as a combination product containing Benzoyl Peroxide, Sulfur) ... NuOx® (as a combination product containing Benzoyl Peroxide, Sulfur) ... Sulfoxyl® (as a combination product containing Benzoyl Peroxide, Sulfur)

  2. Erythromycin and Benzoyl Peroxide Topical

    MedlinePlus

    The combination of erythromycin and benzoyl peroxide is used to treat acne. Erythromycin and benzoyl peroxide are in a class of medications called topical antibiotics. The combination of erythromycin ...

  3. Clindamycin and Benzoyl Peroxide Topical

    MedlinePlus

    The combination of clindamycin and benzoyl peroxide is used to treat acne. Clindamycin and benzoyl peroxide are in a class of medications called topical antibiotics. The combination of clindamycin ...

  4. Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent.

    PubMed

    Burugupalli, Satvika; Shah, Sayali; van der Peet, Phillip L; Arora, Seep; White, Jonathan M; Williams, Spencer J

    2016-01-07

    Hydroxybenzotriazole (HOBt) and HOBt-derived reagents have been classified as Class I explosives, with restrictions on their transportation and storage. We explored a range of benzoylated oxime-based reagents as alternatives to benzoyloxybenzotriazole (BBTZ) for the selective benzoylation of carbohydrate polyols. Benzoylated oximes derived from 2-hydroximino-malononitrile, ethyl 2-hydroximino-2-cyanoacetate (Oxyma), and tert-butyl 2-hydroximino-2-cyanoacetate were most effective for benzoylation of a simple primary alcohol, with yields approaching that obtained for BBTZ. When applied to carbohydrate diols, the most effective reagent was identified as benzoyl-Oxyma. Benzoyl-Oxyma is a highly crystalline, readily prepared alternative to BBTZ, useful in the selective benzoylation of carbohydrate polyols.

  5. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2, CAS Reg. No. 94-36-0) is a colorless, rhombic crystalline solid. It is prepared by reaction of benzoyl chloride, sodium hydroxide,...

  6. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2, CAS... chloride, sodium hydroxide, and hydrogen peroxide. (b) The ingredient meets the specifications of the...

  7. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2, CAS... chloride, sodium hydroxide, and hydrogen peroxide. (b) The ingredient meets the specifications of the...

  8. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2, CAS Reg. No. 94-36-0) is a colorless, rhombic crystalline solid. It is prepared by reaction of...

  9. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2, CAS Reg. No. 94-36-0) is a colorless, rhombic crystalline solid. It is prepared by reaction of...

  10. The evolution of benzoyl peroxide therapy.

    PubMed

    Tanghetti, Emil

    2008-11-01

    Since its first use in dermatology last century, benzoyl peroxide (BPO) has undergone a number of reformulations, each enhancing its efficacy, tolerability, or both. Benzoyl peroxide can be used as monotherapy or in combination with oral or topical antibiotics or topical retinoids. Its antimicrobial activity is based on the generation of highly reactive oxygen radicals, a physicochemical effect to which Propionibacterium acnes has not developed resistance. In addition to its nonspecific antimicrobial activity, BPO has keratolytic, comedolytic, and anti-inflammatory activity in acne. Benzoyl peroxide can be added to antibiotic regimens to help maintain bacterial sensitivity to the antibiotic. Additive or synergistic effects of BPO-antibiotic combinations have been demonstrated. Fixed combinations of BPO with either antibiotics or a retinoid recently have become available and may improve compliance. New moisturizing vehicles and stabilized BPO formulations also have added to tolerability and convenience. Benzoyl peroxide may have underappreciated potential to treat noninflammatory acne as monotherapy or in combination with a topical retinoid, an important antibiotic-sparing strategy.

  11. A Three-Step Synthesis of Benzoyl Peroxide

    ERIC Educational Resources Information Center

    Her, Brenda; Jones, Alexandra; Wollack, James W.

    2014-01-01

    Benzoyl peroxide is used as a bleaching agent for flour and whey processing, a polymerization initiator in the synthesis of plastics, and the active component of acne medication. Because of its simplicity and wide application, benzoyl peroxide is a target molecule of interest. It can be affordably synthesized in three steps from bromobenzene using…

  12. A Three-Step Synthesis of Benzoyl Peroxide

    ERIC Educational Resources Information Center

    Her, Brenda; Jones, Alexandra; Wollack, James W.

    2014-01-01

    Benzoyl peroxide is used as a bleaching agent for flour and whey processing, a polymerization initiator in the synthesis of plastics, and the active component of acne medication. Because of its simplicity and wide application, benzoyl peroxide is a target molecule of interest. It can be affordably synthesized in three steps from bromobenzene using…

  13. Preparation and Cyclodextrin Solubilization of the Antibacterial Agent Benzoyl Metronidazole

    PubMed Central

    Yang, Shuo

    2013-01-01

    A one-pot method for the preparation of benzoyl metronidazole was achieved by using N,N′-carbonyldiimidazole as a coupling reagent. Moreover, it was found that the byproduct imidazole as the catalyst promoted the reaction. In addition, the β-cyclodextrin solubilization of benzoyl metronidazole was investigated by phase-solubility method. The phase-solubility studies indicated that the solubility of benzoyl metronidazole (S = 0.1435 g/L) was substantially increased 9.7-fold (S′ = 1.3881 g/L) by formation of 1 : 1 benzoyl metronidazole/β-cyclodextrin complexes in water, and the association constant K a value was determined to be 251 (±23) dm3/mol. Therefore, β-cyclodextrin can work as a pharmaceutical solubilizer for benzoyl metronidazole and may improve its oral bioavailability. PMID:23970831

  14. In vitro percutaneous absorption of benzoyl peroxide from three fixed combination acne formulations.

    PubMed

    Zeichner, Joshua A; Bhatt, Varsha; Pillai, Radhakrishnan

    2013-08-01

    Fixed combination therapy in acne is standard of care, and benzoyl peroxide is a common component of a number of fixed-dose combination products available today. Given that benzoyl peroxide can cause concentration-dependent irritation, newer combinations have been developed utilizing lower concentrations (2.5%) in their formulation. These formulations have been shown to provide better tolerability than products with higher benzoyl peroxide concentrations, while offering comparable efficacy. In vitro skin permeation studies can be used to determine the relative availability of benzoyl peroxide from different dosage forms. In this in vitro percutaneous absorption study, the authors compared three fixed combinations, two with 2.5% benzoyl peroxide and one with 5% benzoyl peroxide. Both 2.5% benzoyl peroxide products (1.2% clindamycin phosphate and 2.5% benzoyl peroxide, and 0.1% adapalene and 2.5% benzoyl peroxide) had similar benzoyl peroxide delivery profiles in terms of efficiency of deposition and total benzoyl peroxide tissue permeation. Although 1.2% clindamycin phosphate and 2.5% benzoyl peroxide delivered the same amount of benzoyl peroxide into the receptor fluid as 1.2% clindamycin phosphate and 5% benzoyl peroxide, it was statistically more efficient in terms of percent applied dose (P=0.002). This suggests a more advanced formulation, as it contains only half the concentration of benzoyl peroxide. All three products showed similar delivery characteristics in terms of the amount of benzoyl peroxide depositing into the dermis.

  15. Benzoylated ethyl 1-thioglycosides: direct preparation from per-O-benzoylated sugars.

    PubMed

    Sail, Deepak; Kováč, Pavol

    2012-08-01

    D-Glucose, lactose, maltose, and melibiose were benzoylated with Bz(2)O-Et(3)N reagent to give fully benzoylated β products. Under the same conditions, D-mannose produced a mixture where the β-benzoate predominated. Treatment of the foregoing compounds with EtSH at slightly elevated temperature (50-60°C) in the presence of BF(3)·Et(2)O as a promoter gave the corresponding ethyl 1-thio glycosides in high yields. The α-products predominated in all cases in the anomeric mixtures formed. Individual products of all reactions were isolated by chromatography, they were obtained in analytically pure state, and were fully characterized by (1)H and (13)C NMR data and physical constants.

  16. Benzoyl peroxide: enhancing antibiotic efficacy in acne management.

    PubMed

    Dutil, Maha

    2010-01-01

    Benzoyl peroxide is one of the most widely used topical agents for acne. It has potent antibacterial and mild anti-inflammatory and comedolytic effects. To treat mild to moderate acne, it can be used alone or in combination with topical antibiotics and topical retinoids. The combination of benzoyl peroxide with either erythromycin or clindamycin is synergistic and well-tolerated. In more severe acne, when oral antibiotics are required, benzoyl peroxide can contribute to suppressing the emergence of resistant strains of Propionibacterium acnes.

  17. Tetrafluoroethylene telomerization initiated by benzoyl peroxide

    NASA Astrophysics Data System (ADS)

    Bolshakov, A. I.; Kuzina, S. I.; Kiryukhin, D. P.

    2017-03-01

    The radical telomerization of tetrafluoroethylene initiated by benzoyl peroxide (BP) photolysis at λ ≥ 365 nm is studied in acetone, dichloromethane, carbon tetrachloride, and Freon 114B2 at 25°C. The products of synthesis are a mixture of telomers of different molar masses, segregated into soluble and insoluble fractions. To characterize the radicals initiating telomerization, crystalline BP and its solution in ethanol are subjected to low-temperature (77 K) photolysis, with the liquid system serving as a model for BP behavior in solutions of telogens. It is established that radicals are not only initiators but also participate in chain termination reactions, lowering the telomers' molar mass and thus raising the proportion of the soluble fraction. Telomerization initiated by an initiator compound versus initiation by gamma radiation are compared and discussed.

  18. A Three-Step Acne System Containing Solubilized Benzoyl Peroxide versus Benzoyl Peroxide/Clindamycin in Pediatric Patients with Acne.

    PubMed

    Eichenfield, Lawrence F; Thiboutot, Diane; Shalita, Alan; Swinyer, Leonard; Tanghetti, Emil; Tschen, Eduardo; Parr, Lisa

    2009-11-01

    Objective. To evaluate the clinical benefit in adolescents of a three-step acne system containing solubilized benzoyl peroxide. Design. Patients in this multicenter, investigator-blind trial were randomly assigned to receive 10 weeks of treatment with either the three-step acne system for normal-to-oily skin (proprietary 2% salicylic acid cleanser twice daily + proprietary 2% salicylic acid toner once daily + solubilized 5% benzoyl peroxide gel twice daily) or with control cleanser + 5% benzoyl peroxide/1% clindamycin gel twice daily. Setting. Patients seeking acne treatment from a dermatologist. Pediatric subgroup analysis from a larger trial. Participants. Eighty-two adolescents with mild-to-moderate facial acne vulgaris. Measurements. Noninflammatory and inflammatory lesion counts, erythema, dryness, peeling, burning/stinging, and itching. Results. The three-step acne system was significantly more effective than benzoyl peroxide/clindamycin in reducing the noninflammatory lesion count at Weeks 2 and 4. The antibiotic-free acne system was also comparably effective to benzoyl peroxide/clindamycin in reducing the inflammatory lesion count at all timepoints. Both regimens were generally well tolerated with mean levels of erythema, dryness, peeling, burning/stinging, and itching less than mild in both groups at all timepoints. Conclusions. The three-step acne system is an effective antibiotic-free acne treatment. Relative to benzoyl peroxide/clindamycin, its ability to achieve comparable reductions in inflammatory lesions, and significantly greater reductions in noninflammatory lesions in the early weeks of treatment is likely attributable to the solubilization of the benzoyl peroxide enhancing the bioavailability and intrafollicular penetration of the benzoyl peroxide.

  19. Two benzoyl coumarin amide fluorescence chemosensors for cyanide anions

    NASA Astrophysics Data System (ADS)

    Wang, Zian; Wu, Qianqian; Li, Jiale; Qiu, Shuang; Cao, Duxia; Xu, Yongxiao; Liu, Zhiqiang; Yu, Xueying; Sun, Yatong

    2017-08-01

    Two new benzoyl coumarin amide derivatives with ortho hydroxyl benzoyl as terminal group have been synthesized. Their photophysical properties and recognition properties for cyanide anions in acetonitrile have also been examined. The influence of electron donating diethylamino group in coumarin ring and hydroxyl in benzoyl group on recognition properties was explored. The results indicate that the compounds can recognize cyanide anions with obvious absorption and fluorescence spectral change and high sensitivity. The import of diethylamine group increases smartly the absorption ability and fluorescence intensity of the compound, which allows the recognition for cyanide anions can be observed by naked eyes. The in situ hydrogen nuclear magnetic resonance spectra combining photophysical properties change and job's plot data confirm that Michael addition between the chemosensors and cyanide anions occurs. Molecular conjugation is interrupted, which leads to fluorescence quenching. At the same time, there is a certain extent hydrogen bond reaction between cyanide and hydroxyl group in the compounds, which is beneficial to the recognition.

  20. N-Benzoyl-4-nitro-benzene-sulfonamide monohydrate.

    PubMed

    Suchetan, P A; Foro, Sabine; Gowda, B Thimme; Vidya, V M

    2012-01-01

    In the title compound, C(13)H(10)N(2)O(5)S·H(2)O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 83.4 (1)°. In the crystal, the water mol-ecule forms four hydrogen bonds with three different mol-ecules of N-benzoyl-4-nitro-benzene-sulfonamide. One of the H atoms of H(2)O forms a bifurcated hydrogen bond with a sulfonyl and the carbonyl O atoms. Mol-ecules are linked into a three-dimensional network by N-H⋯O and O-H⋯O hydrogen bonds.

  1. Selective assay of benzoyl peroxide in lotions and creams.

    PubMed

    Daly, R E; Lomner, J J; Chafetz, L

    1975-12-01

    A selective titrimetric method for the determination of benzoyl peroxide in lotions and creams was developed. It is based on the work of Horner and Jürgens, in which diacylperoxides, dialkylperoxides, peracids, and alkylhydroperoxides can be determined selectively by iodometry and acidimetry. The proposed assay is stability indicating with respect to peracids. Good recovery data were obtained.

  2. The utility of benzoyl peroxide in hydrophase base (Brevoxyl) in the treatment of acne vulgaris.

    PubMed

    Weinberg, Jeffrey M

    2006-04-01

    Available for more than 5 decades, benzoyl peroxide has been a "workhorse" of acne therapy. The benefits of this agent include reduction in Propionibacterium acnes (P. acnes) with decrease in inflammatory lesions, efficacy as both "leave on" and cleanser formulations and reduced emergence of antibiotic-resistant P. acnes strains. As the effect of benzoyl peroxide on P. acnes is a direct toxic effect rather than as a "true" antibiotic, resistance to benzoyl peroxide does not occur and has never been reported. Benzoyl peroxide in hydrophase base (Brevoxyl Creamy Washes and Gels) has shown significant efficacy in the treatment of acne, with lower irritancy than other benzoyl peroxide preparations. It is felt that the low irritancy of this product is related to a unique delivery vehicle containing dimethyl isosorbide, which dissolves benzoyl peroxide crystals on the skin. Clinical studies demonstrating the efficacy and safety of benzoyl peroxide in hydrophase base will be reviewed.

  3. Allergic Contact Dermatitis to Benzoyl Peroxide Resembling Impetigo.

    PubMed

    Kim, Changhyun; Craiglow, Brittany G; Watsky, Kalman L; Antaya, Richard J

    2015-01-01

    A 17-year-old boy presented with recurring severe dermatitis of the face of 5-months duration that resembled impetigo. He had been treated with several courses of antibiotics without improvement. Biopsy showed changes consistent with allergic contact dermatitis and patch testing later revealed sensitization to benzoyl peroxide, which the patient had been using for the treatment of acne vulgaris. © 2015 Wiley Periodicals, Inc.

  4. Preparation and characterization of N-benzoyl-O-acetyl-chitosan.

    PubMed

    Cai, Jinping; Dang, Qifeng; Liu, Chengsheng; Fan, Bing; Yan, Jingquan; Xu, Yanyan; Li, Jingjing

    2015-01-01

    A novel amphipathic chitosan derivative, N-benzoyl-O-acetyl-chitosan (BACS), was prepared by using the selective partial acylation of chitosan (CS), benzoyl chloride, and acetic acid under high-intensity ultrasound. The chemical structure and physical properties of BACS were characterized by FTIR, (1)H NMR, TGA, and XRD techniques. The degrees of substitution of benzoyl and acetyl for the chitosan derivatives were 0.26 and 1.15, respectively, which were calculated from the peak areas in NMR spectra by using the combined integral methods. The foaming properties of CS and BACS were determined and the results suggested BACS had better foam capacity and stability than those of chitosan. In addition, the antimicrobial activities of CS and BACS were also investigated against two species of bacteria (Escherichia coli and Staphylococcus aureus) and a fungus (Aspergillus niger), the results indicated that the antibacterial and antifungal activities of BACS were much stronger than those of the parent chitosan. These findings suggested that BACS was preferable for use as a food additive with a dual role of both foaming agent and food preservative.

  5. A Case of a Paediatric Patient With Allergic Contact Dermatitis to Benzoyl Peroxide.

    PubMed

    Sandre, Matthew; Skotnicki-Grant, Sandra

    2017-09-01

    Allergic contact dermatitis to benzoyl peroxide can occur in up to 6.5% of those with a history of exposure to this potential allergen. Conversely, irritant contact dermatitis is very common with benzoyl peroxide and can be differentiated from allergic contact dermatitis based on the patient's history and clinical signs and symptoms. We present a case of a paediatric patient with patch test-confirmed severe allergic contact dermatitis to benzoyl peroxide requiring hospitalisation and systemic treatment.

  6. Carcinogenesis studies with benzoyl peroxide (Panoxyl gel 5%)

    SciTech Connect

    Iversen, O.H.

    1986-04-01

    Several groups of hairless mice were given UV radiation with and without pretreatment with 7,12-dimethylbenz(a)anthracene (DMBA), 5% benzoyl peroxide in a gel (Panoxyl), and gel alone, in various combinations, with appropriate control groups included, in order to see whether benzoyl peroxide, which is known to enhance chemical skin carcinogenesis after a single, small dose of DMBA, also enhances UV carcinogenesis. The mice were observed for skin tumors, and all skin lesions were histologically investigated. The percentage of tumor-bearing animals with time is called the tumor rate, the total number of tumors occurring is called the tumor yield. Continual treatment with 5% benzoyl peroxide in gel twice a week, with or without a short pretreatment period of UV radiation resulted in only 2 skin carcinomas, which is remarkable, but not significant. Both Panoxyl and gel alone enhanced tumorigenicity significantly in animals pretreated with a single dose of 51.2 micrograms DMBA. There was no difference between the enhancement caused by Panoxyl and the gel as regards the tumor rate, but when measured as final tumor yield, Panoxyl was slightly more tumor-enhancing than gel alone. However, both Panoxyl and gel protected significantly against UV tumorigenesis (all tumors). There was no difference between the protective effect of the 2 types of treatment. Neither Panoxyl nor gel alone influenced significantly UV skin carcinogenesis (malignant tumors). It is concluded that under these experimental conditions both Panoxyl and gel alone tend to protect against the tumorigenicity and do not enhance the carcinogenicity of UV radiation in hairless mice, whereas both gel and Panoxyl enhance chemical carcinogenesis. The carcinogenic mechanisms may be different for UV and chemical carcinogenesis, respectively.

  7. Investigating the Stability of Benzoyl Peroxide in Over-the-Counter Acne Medications

    ERIC Educational Resources Information Center

    Kittredge, Marina Canepa; Kittredge, Kevin W.; Sokol, Melissa S.; Sarquis, Arlyne M.; Sennet, Laura M.

    2008-01-01

    One of the most commonly used ingredients in over-the-counter acne treatments in cream, gel, and wash form is benzoyl peroxide. It is an anti-bacterial agent that kills the bacterium ("Propionibacterium acne") involved in the formation of acne. The formulation of these products is extremely difficult owing to the instability of benzoyl peroxide.…

  8. Investigating the Stability of Benzoyl Peroxide in Over-the-Counter Acne Medications

    ERIC Educational Resources Information Center

    Kittredge, Marina Canepa; Kittredge, Kevin W.; Sokol, Melissa S.; Sarquis, Arlyne M.; Sennet, Laura M.

    2008-01-01

    One of the most commonly used ingredients in over-the-counter acne treatments in cream, gel, and wash form is benzoyl peroxide. It is an anti-bacterial agent that kills the bacterium ("Propionibacterium acne") involved in the formation of acne. The formulation of these products is extremely difficult owing to the instability of benzoyl peroxide.…

  9. A complete gear system in N-benzoyl-carbazole derivatives.

    PubMed

    Tabata, Hidetsugu; Kayama, Susumu; Takahashi, Yuka; Tani, Norihiko; Wakamatsu, Shintaro; Tasaka, Tomohiko; Oshitari, Tetsuta; Natsugari, Hideaki; Takahashi, Hideyo

    2014-03-07

    2',6'-Disubstituted N-benzoylated carbazole derivatives were found to exhibit atropisomerism. The bulky substituents restricted rotation about the N-C7' and C7'-C1' bonds to separate four atropisomers, in which rotation about the C7'-C1' bond was in perfect concert with rotation about the N-C7' bond. Complete geared rotation without slippage at 37 °C for 7 days was observed for the first time. Conformational analysis clarified the preference for the gear system over other internal conversion pathways.

  10. Methyl 3-(3-benzoyl-thio-ureido)propano-ate.

    PubMed

    Hassan, Ibrahim N; Yi, Chong Yan; Kassim, Mohammad B

    2011-04-01

    In the title compound, C(12)H(14)N(2)O(3)S, the propyl acetate group and the benzoyl group adopt a cis-trans conformation, respectively, with respect to the thiono S atom across the C-N bonds. The phenyl ring is twisted relative to the the thio-urea mean plane, forming a dihedral angle of 24.16 (9)°. An intra-molecular N-H⋯O hydrogen bond occurs. The crystal packing is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming a chain along the a axis.

  11. Efficacy and Tolerability of a Three-Step Acne System Containing a Solubilized Benzoyl Peroxide Lotion versus a Benzoyl Peroxide/Clindamycin Combination Product

    PubMed Central

    Del Rosso, James Q.

    2008-01-01

    A brand three-step acne treatment system containing a solubilized 5% benzoyl lotion and a designated cleanser and moisturizer was compared with a brand benzoyl peroxide 5%/clindamycin 1% gel in subjects with acne vulgaris. The single-center, four-week study was investigator-blinded and randomized. The three-step acne treatment system proved to be comparable in efficacy and tolerability. PMID:21203357

  12. Hydrogen peroxide as a new defensive compound in "benzoyl cyanide" producing polydesmid millipedes

    NASA Astrophysics Data System (ADS)

    Kuwahara, Yasumasa; Yamaguchi, Takuya; Ichiki, Yayoi; Tanabe, Tsutomu; Asano, Yasuhisa

    2017-04-01

    Hydrogen peroxide was newly and simultaneously demonstrated with well-known hydrogen cyanide as a component of defensive secretions of "benzoyl cyanide" producing polydesmid millipedes. Presence of hydrogen peroxide was successively evidenced by Trinder reagent's spray with colorless as well as oily smears of defensive secretions containing benzoyl cyanide and hydrogen cyanide by alkaline picrate paper treatment. Linear correlation was demonstrated between quantities of hydrogen peroxide and benzoyl cyanide. By qualitative assay, seven benzoyl cyanide containing polydesmidans (six species of adults and one species of a nymph at stadium I) tested positive to Trinder reagent, indicative of the presence of hydrogen peroxide (together with hydrogen cyanide), while two cyanogenic species without benzoyl cyanide exhibited negative responses to the reagent. Two types of millipedes were elucidated as species of cyanogenic Polydesmida.

  13. Hydrogen peroxide as a new defensive compound in "benzoyl cyanide" producing polydesmid millipedes.

    PubMed

    Kuwahara, Yasumasa; Yamaguchi, Takuya; Ichiki, Yayoi; Tanabe, Tsutomu; Asano, Yasuhisa

    2017-04-01

    Hydrogen peroxide was newly and simultaneously demonstrated with well-known hydrogen cyanide as a component of defensive secretions of "benzoyl cyanide" producing polydesmid millipedes. Presence of hydrogen peroxide was successively evidenced by Trinder reagent's spray with colorless as well as oily smears of defensive secretions containing benzoyl cyanide and hydrogen cyanide by alkaline picrate paper treatment. Linear correlation was demonstrated between quantities of hydrogen peroxide and benzoyl cyanide. By qualitative assay, seven benzoyl cyanide containing polydesmidans (six species of adults and one species of a nymph at stadium I) tested positive to Trinder reagent, indicative of the presence of hydrogen peroxide (together with hydrogen cyanide), while two cyanogenic species without benzoyl cyanide exhibited negative responses to the reagent. Two types of millipedes were elucidated as species of cyanogenic Polydesmida.

  14. Formulation and characterization of benzoyl peroxide gellified emulsions.

    PubMed

    Thakur, Naresh Kumar; Bharti, Pratibha; Mahant, Sheefali; Rao, Rekha

    2012-01-01

    The present investigation was carried out with the objective of formulating a gellified emulsion of benzoyl peroxide, an anti-acne agent. The formulations were prepared using four different vegetable oils, viz. almond oil, jojoba oil, sesame oil, and wheat germ oil, owing to their emollient properties. The idea was to overcome the skin irritation and dryness caused by benzoyl peroxide, making the formulation more tolerable. The gellified emulsions were characterized for their homogeneity, rheology, spreadability, drug content, and stability. In vitro permeation studies were performed to check the drug permeation through rat skin. The formulations were evaluated for their antimicrobial activity, as well as their acute skin irritation potential. The results were compared with those obtained for the marketed formulation. Later, the histopathological examination of the skin treated with various formulations was carried out. Formulation F3 was found to have caused a very mild dysplastic change to the epidermis. On the other hand, the marketed formulation led to the greatest dysplastic change. Hence, it was concluded that formulation F3, containing sesame oil (6%w/w), was the optimized formulation. It exhibited the maximum drug release and anti-microbial activity, in addition to the least skin irritation potential.

  15. Formulation and Characterization of Benzoyl Peroxide Gellified Emulsions

    PubMed Central

    Thakur, Naresh Kumar; Bharti, Pratibha; Mahant, Sheefali; Rao, Rekha

    2012-01-01

    The present investigation was carried out with the objective of formulating a gellified emulsion of benzoyl peroxide, an anti-acne agent. The formulations were prepared using four different vegetable oils, viz. almond oil, jojoba oil, sesame oil, and wheat germ oil, owing to their emollient properties. The idea was to overcome the skin irritation and dryness caused by benzoyl peroxide, making the formulation more tolerable. The gellified emulsions were characterized for their homogeneity, rheology, spreadability, drug content, and stability. In vitro permeation studies were performed to check the drug permeation through rat skin. The formulations were evaluated for their antimicrobial activity, as well as their acute skin irritation potential. The results were compared with those obtained for the marketed formulation. Later, the histopathological examination of the skin treated with various formulations was carried out. Formulation F3 was found to have caused a very mild dysplastic change to the epidermis. On the other hand, the marketed formulation led to the greatest dysplastic change. Hence, it was concluded that formulation F3, containing sesame oil (6%w/w), was the optimized formulation. It exhibited the maximum drug release and anti-microbial activity, in addition to the least skin irritation potential. PMID:23264949

  16. Rapid detection of benzoyl peroxide in wheat flour by using Raman scattering spectroscopy

    NASA Astrophysics Data System (ADS)

    Zhao, Juan; Peng, Yankun; Chao, Kuanglin; Qin, Jianwei; Dhakal, Sagar; Xu, Tianfeng

    2015-05-01

    Benzoyl peroxide is a common flour additive that improves the whiteness of flour and the storage properties of flour products. However, benzoyl peroxide adversely affects the nutritional content of flour, and excess consumption causes nausea, dizziness, other poisoning, and serious liver damage. This study was focus on detection of the benzoyl peroxide added in wheat flour. A Raman scattering spectroscopy system was used to acquire spectral signal from sample data and identify benzoyl peroxide based on Raman spectral peak position. The optical devices consisted of Raman spectrometer and CCD camera, 785 nm laser module, optical fiber, prober, and a translation stage to develop a real-time, nondestructive detection system. Pure flour, pure benzoyl peroxide and different concentrations of benzoyl peroxide mixed with flour were prepared as three sets samples to measure the Raman spectrum. These samples were placed in the same type of petri dish to maintain a fixed distance between the Raman CCD and petri dish during spectral collection. The mixed samples were worked by pretreatment of homogenization and collected multiple sets of data of each mixture. The exposure time of this experiment was set at 0.5s. The Savitzky Golay (S-G) algorithm and polynomial curve-fitting method was applied to remove the fluorescence background from the Raman spectrum. The Raman spectral peaks at 619 cm-1, 848 cm-1, 890 cm-1, 1001 cm-1, 1234 cm-1, 1603cm-1, 1777cm-1 were identified as the Raman fingerprint of benzoyl peroxide. Based on the relationship between the Raman intensity of the most prominent peak at around 1001 cm-1 and log values of benzoyl peroxide concentrations, the chemical concentration prediction model was developed. This research demonstrated that Raman detection system could effectively and rapidly identify benzoyl peroxide adulteration in wheat flour. The experimental result is promising and the system with further modification can be applicable for more products in near

  17. Genetic Diversity of Benzoyl Coenzyme A Reductase Genes Detected in Denitrifying Isolates and Estuarine Sediment Communities

    PubMed Central

    Song, Bongkeun; Ward, Bess B.

    2005-01-01

    Benzoyl coenzyme A (benzoyl-CoA) reductase is a central enzyme in the anaerobic degradation of organic carbon, which utilizes a common intermediate (benzoyl-CoA) in the metabolism of many aromatic compounds. The diversity of benzoyl-CoA reductase genes in denitrifying bacterial isolates capable of degrading aromatic compounds and in river and estuarine sediment samples from the Arthur Kill in New Jersey and the Chesapeake Bay in Maryland was investigated. Degenerate primers were developed from the known benzoyl-CoA reductase genes from Thauera aromatica, Rhodopseudomonas palustris, and Azoarcus evansii. PCR amplification detected benzoyl-CoA reductase genes in the denitrifying isolates belonging to α-, β-, or γ-Proteobacteria as well as in the sediment samples. Phylogenetic analysis, sequence similarity comparison, and conserved indel determination grouped the new sequences into either the bcr type (found in T. aromatica and R. palustris) or the bzd type (found in A. evansii). All the Thauera strains and the isolates from the genera Acidovorax, Bradyrhizobium, Paracoccus, Ensifer, and Pseudomonas had bcr-type benzoyl-CoA reductases with amino acid sequence similarities of more than 97%. The genes detected from Azarocus strains were assigned to the bzd type. A total of 50 environmental clones were detected from denitrifying consortium and sediment samples, and 28 clones were assigned to either the bcr or the bzd type of benzoyl-CoA reductase genes. Thus, we could determine the genetic capabilities for anaerobic degradation of aromatic compounds in sediment communities of the Chesapeake Bay and the Arthur Kill on the basis of the detection of two types of benzoyl-CoA reductase genes. The detected genes have future applications as genetic markers to monitor aromatic compound degradation in natural and engineered ecosystems. PMID:15812036

  18. Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase.

    PubMed

    Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao

    2016-05-17

    A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy.

  19. Benzoyl peroxide interferes with metabolic co-operation between cultured human epidermal keratinocytes

    SciTech Connect

    Lawrence, N.J.; Parkinson, E.K.; Emmerson, A.

    1984-03-01

    The ability of benzoyl peroxide to inhibit metabolic co-operation in rodent cell cultures may be relevant to its recently reported tumour promoting activity in mouse epidermis. We show here that non-toxic doses of this compound reduce metabolic co-operation between human epidermal keratinocytes to approximately 30% of that found in controls. The doses of benzoyl peroxide used did not affect keratinocyte morphology or their rate of attachment to the culture substratum. These results could be important as benzoyl peroxide is widely used in industry.

  20. Discriminative Dissolution Method for Benzoyl Metronidazole Oral Suspension.

    PubMed

    da Silva, Aline Santos; da Rosa Silva, Carlos Eduardo; Paula, Fávero Reisdorfer; da Silva, Fabiana Ernestina Barcellos

    2016-06-01

    A dissolution method for benzoyl metronidazole (BMZ) oral suspensions was developed and validated using a high-performance liquid chromatography (HPLC) method. After determination of sink conditions, dissolution profiles were evaluated using different dissolution media and agitation speeds. The sample insertion mode in dissolution media was also evaluated. The best conditions were obtained using a paddle, 50 rpm stirring speed, simulated gastric fluid (without pepsin) as the dissolution medium, and sample insertion by a syringe. These conditions were suitable for providing sink conditions and discriminatory power between different formulations. Through the tested conditions, the results can be considered specific, linear, precise, accurate, and robust. The dissolution profiles of five samples were compared using the similarity factor (f 2) and dissolution efficiency. The dissolution kinetics were evaluated and described by the Weibull model. Whereas there is no monograph for this pharmaceutical formulation, the dissolution method proposed can be considered suitable for quality control and dissolution profile comparison of different commercial formulations.

  1. Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound

    SciTech Connect

    Slaga, T.J.; Klein-Szanto, A.J.P.; Triplett, L.L.; Yotti, L.P.; Trosko, J.E.

    1981-08-28

    Benzoyl peroxide, a widely used free radical-generating compound, promoted both papillomas and carcinomas when it was topically applied to mice after 7, 12-dimethylbenz(a)anthracene initiation. Benzoyl peroxide was inactive on the skin as a complete carcinogen or as a tumor initiator. A single topical application of benzoyl peroxide produced a marked epidermal hyperplasia and induced a large number of dark basal keratinocytes, effects similar to those produced by the potent tumor promoter 12-O-tetradecanoyl phorbol-13-acetate. Benzoyl peroxide, like other known tumor promoters, also inhibited metabolic cooperation (intercellular communication) in Chinese hamster cells. In view of these results caution should be recommended in the use of this and other free radical-generating compounds.

  2. Clindamycin/benzoyl peroxide gel (BenzaClin): a review of its use in the management of acne.

    PubMed

    McKeage, Kate; Keating, Gillian M

    2008-01-01

    Clindamycin 1%/benzoyl peroxide 5% (BenzaClin) is a combination gel indicated for use twice daily, or as directed by a physician, for the topical treatment of inflammatory and noninflammatory lesions of acne vulgaris. In well designed clinical trials in patients with mild to moderately severe acne, the efficacy of once- or twice-daily clindamycin/benzoyl peroxide in the reduction of inflammatory lesion counts was greater than that of benzoyl peroxide alone, clindamycin alone, or tretinoin plus clindamycin, and not significantly different from that of erythromycin/benzoyl peroxide. In the reduction of noninflammatory lesion counts, the efficacy of once- or twice-daily clindamycin/benzoyl peroxide was greater than that of clindamycin alone, but not significantly different to that observed with benzoyl peroxide, tretinoin plus clindamycin, or erythromycin/benzoyl peroxide. Clindamycin/benzoyl peroxide has a fairly rapid onset of action, with acne improvement usually recorded within 2-4 weeks. Despite widespread use, bacterial resistance is not associated with clindamycin/benzoyl peroxide. The product is generally well tolerated, and the main treatment-related adverse events in clinical trials were application-site dryness, irritation, peeling, and erythema. Thus, clindamycin/benzoyl peroxide is an effective and well tolerated option for the management of mild to moderately severe acne.

  3. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae

    DOE PAGES

    Eudes, Aymerick; Teixeira Benites, Veronica; Wang, George; ...

    2015-10-02

    Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilatesmore » by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. Finally, this work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases.« less

  4. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae

    SciTech Connect

    Eudes, Aymerick; Teixeira Benites, Veronica; Wang, George; Baidoo, Edward E. K.; Lee, Taek Soon; Keasling, Jay D.; Loqué, Dominique

    2015-10-02

    Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. Finally, this work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases.

  5. X-ray investigations of sulfur-containing fungicides. IV. 4'-[[Benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl]acetanilide and 4'-[[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl]acetanilide.

    PubMed

    Wolf, W M

    2001-09-01

    The conformations of the two approximately isomorphous structures 4'-[[benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl]acetanilide, C(22)H(18)ClN(3)O(4)S, and 4'-[[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl]acetanilide, C(23)H(21)N(3)O(5)S, are stabilized by resonance-assisted intramolecular hydrogen bonds linking the hydrazone moieties and sulfonyl groups. The stronger bond is observed in the former compound. The difference in electronic properties between the Cl atom and the methoxy group is too small to significantly alter the non-bonding interactions of the sulfonyl and beta-carbonyl groups.

  6. [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid].

    PubMed

    Worret, Wolf-Ingo; Fluhr, Joachim W

    2006-04-01

    Benzoyl peroxide (BPO) was introduced in the treatment of acne in 1934. Despite the fact that only few randomized trials have been published, BPO is considered the standard in topical acne treatment. Anaerobic bacteria are reduced by oxidative mechanisms and the induction of resistant strains is reduced. Topical formulations are available at concentrations of 2.5, 5, 10 and 20 %. The effect is dose-dependent, but the irritation increases with higher concentrations. Usually 5 % BPO is sufficient to control acne grade I-II. Due to its strong oxidative potential, patients should be advised that BPO may bleach colored and dark clothing, bedding and even hair. BPO is safe for use in pregnant and lactating females because it is degraded to benzoic acid. It is a cost-effective treatment for acne grade I-II. Patients with papulopustular acne grade I-II, particularly with marked inflammation, show satisfactory improvement with topical antibiotic treatment. The following compounds are available and effective: erythromycin, clindamycin and tetracycline (the latter being less frequently used). A review in 1990 suggested that topical tetracycline was ineffective in the treatment of acne. Along with eliminating Propionibacterium acnes, the main mechanism of topical antibiotics is their antiinflammatory effect. All three penetrate the epidermal barrier well and are similarly efficacious. Randomized trials have shown that in concentrations of 2-4 %, their effects are comparable to oral tetracycline and minocycline. Combination therapy with retinoids or benzoyl peroxide (BPO) increases efficacy. Retinoids increase penetration and reduce comedones, while topical antibiotics primarily address inflammation. One side effect of topical antibacterial treatment is an increase in drug-resistant resident skin flora with gram-negative microorganisms prevailing, which can lead to gram-negative folliculitis. All three antibiotics fluoresce under black light which may produce interesting

  7. [Antibiotics, azelaic acid and benzoyl peroxide in topical acne therapy].

    PubMed

    Fluhr, Joachim W; Degitz, Klaus

    2010-03-01

    Benzoyl peroxide was introduced as a basic treatment already in acne therapy 1934. The mechanism of action is the reduction of anaerobe bacteria by strong oxidation processes. No resistancies have been ever reported. BPO is available in 2.5, 5 and 10 % formulations. Its efficacy is slightly related to the strength of concentrations, but the side effect profile with burning, erythema and desquamation is increasing with concentrations. BPO 5% mostly is efficient enough to control acne of grades I to II according to the Kligman & Plewig classification. BPO my bleach clothes and hair. It is the most costeffective topical drug in acne of grades I-II. Inflammatory acne of the papular-pustular type I-II can also be treated by topical antibiotics such as erythromycin, clindamycin, and, less frequent and today not anymore recommended tetracyclines. Mechanism of action is not alone an antibacterial but anti inflammatory effect. The efficacy and penetration of the topical antibiotics between the groups are similar. Randomized studies have shown that concentrations of 2-4% are equivalent to oral tetracycline and minocycline in mild to moderate acne. Combinatory formulations with BPO and with retinoids enhance the efficacy significantly. Topical antibiotics plus BPO show less bacterial resistancies as topical antibiotics alone. Antibiotics should therefore not be used as monotherapy. Moreover gram negative folliculitis may develop. Azelaic acid is acting as an antimicrobial and can also reduce comedones. It can also be used in pregnancy and during the lactation period.

  8. N-Benzoyl-2-nitro-benzene-sulfonamide.

    PubMed

    Suchetan, P A; Foro, Sabine; Gowda, B Thimme; Nirmala, B

    2012-02-01

    In the title compound, C(13)H(10)N(2)O(5)S, the N-C bond in the C-SO(2)-NH-C segment has gauche torsion angles with respect to the S=O bonds. The conformation between the N-H bond and the ortho-nitro group in the sulfonyl benzene ring is syn. The mol-ecule is twisted at the S-N bond with a torsion angle of -63.4 (2)°. The sulfonyl benzene ring is tilted by 77.1 (1)° relative to the -SO(2)-NH-C-O segment. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into inversion dimers, which are linked by weak C-H⋯O and C-H⋯π inter-actions along the b axis.

  9. Raman hyperspectral image analysis of benzoyl peroxide additive

    NASA Astrophysics Data System (ADS)

    Wang, Xiaobin; Huang, Wenqian; Wang, Qingyan; Liu, Chen; Wang, Chaopeng; Yang, Guiyan; Zhao, Chunjiang

    2017-06-01

    This study adopted a Raman hyperspectral imaging system to collect the Raman spectra and hyperspectral images of benzoyl peroxide (BPO) additive for subsequent analysis. The raw Raman spectra of BPO were preprocessed by wavelet denoising. Optimal parameters of wavelet denoising were selected by the orthogonal experimental design. The signal-noise (S/N) ratio of the optimal parameter combination was 32.848. The smoothed Raman spectra were divided into three regions (1900-1300, 1300-700, and 700-100 cm-1) for assignment and the band vibrational modes of BPO molecule were obtained. Wherein, the Raman bands at 1771, 1597, 1230, 999, 889 and 845 cm-1 are higher than others, and can be used as the Raman characteristic bands. Analysis of the grayscale images corresponding to different characteristic bands, it is found that the order of change of the image gray level was consistent with characteristic bands intensity. Findings of this study provide the research basics for the detection and analysis of BPO additive.

  10. Electrophysiological effects of L 9394 (benzoyl-indolizine) in man.

    PubMed Central

    Waleffe, A; Bordalo, A; Bruninx, P; Wellens, H J; Kulbertus, H E

    1979-01-01

    The electrophysiological effects of L 9394 (benzoyl-indolizine), a substance chemically related to amiodarone, but devoid of iodine atoms, were investigated by programmed electrical stimulation of the heart in 12 patients with various forms of tachycardia. Four subjects had electrocardiographic evidence of the WPW syndrome and episodes of circus movement tachycardia. Paroxysmal supraventricular tachycardia, confined to the atrioventricular (AV) node, was found in 3 patients. In 2 cases, where a short PR interval was present, the main complaint was the occurrence of paroxysmal atrial fibrillation. In the remaining 3 instances, the arrhythmia consisted of slow ventricular tachycardia (1 case), supraventricular tachycardia of the focal type (1 case), and episodes of primary ventricular fibrillation, not related to acute myocardial ischaemia (1 case). L 9394 injected intravenously was seen to lengthen the transnodal conduction time as well as the effective and functional refractory periods of the node. Similar effects were found on the retrograde VA pathway. The drug had no action on the infra-Hisian conduction system, on the refractory periods of ventricular muscle, or on the refractory periods of accessory bypasses. The drug was injected during an episode of tachycardia in 6 cases with reproducible supraventricular re-entrant tachycardia. Three had a tachycardia circuit confined to the node. In those instances, the drug had beneficial effects (slowing and interruption of tachycardia, decrease or abolition of echo zone; loss of ability to induce tachycardia). In the other 3 cases, an accessory pathway was incorporated in the circuit. L 9394 interrupted the tachycardia in 2 instances (by anterograde AV block), but failed to protect all 3 patients against reinitiation of tachycardia by premature stimuli. It is concluded that L9394 does not share all the pharmacological properties of amiodarone and will not replace it in all its indications. Images PMID:426960

  11. Loss of benzaldehyde in the fragmentation of protonated benzoylamines: Benzoyl cation as a hydride acceptor in the gas phase.

    PubMed

    Chai, Yunfeng; Shao, Yunlong; Wang, Lu; Wang, Lin

    2017-07-14

    In electrospray ionization tandem mass spectrometry of protonated 1-benzoylamines (1-benzoylpiperadine, 1-benzoylmorpholine, and 1-benzoyl-4-methylpiperazine), the dominant fragmentation pathway was amide bond cleavage to form benzoyl cation and neutral amine. Meanwhile, in their fragmentations, an interesting loss of benzaldehyde (106 Da) was observed and identified to derive from hydride transfer reaction between the benzoyl cation and amine. A stepwise mechanism for loss of 106 Da (benzene and CO) could be excluded with the aid of deuterium labeling experiment. Theoretical calculations indicated that hydride transfers from amines (piperadine, morpholine and 1-methylpiperazine) to benzoyl cation were thermodynamically permitted and 1-methylpiperazine was the best hydride donor among the three amines. The mass spectrometric experimental results were consistent with the computational results. The relative abundance of the iminium cation (relative to the benzoyl cation) in the fragmentation of protonated 1-benzoyl-4-methylpiperazine was higher than that in the fragmentation of the other two protonated 1-benzoylamines. By comparing the fragmentations of protonated 1-benzyl-4-methylpiperazine and protonated 1-benzoyl-4-methylpiperazine and the energetics of their hydride transfer reactions, this study revealed that benzoyl cation was a hydride acceptor in the gas phase, but which was weaker than benzyl cation. This article is protected by copyright. All rights reserved.

  12. Catalytic effects in the reaction of polypropylene with benzoyl peroxide and structural-kinetic model of the polymer

    SciTech Connect

    Mikheev, Yu.A.; Guseva, L.N.; Toptygin, D.Ya.

    1987-09-01

    The kinetic peculiarities of the chain arylation of polypropylene with benzoyl peroxide and the yields of the transformation products (arylated polypropylene benzene, and benzoic acid) were established. The equation of the reaction rate depends on the way in which the samples were prepared and on the benzoyl peroxide concentration in the polymer. The kinetic peculiarities found were explained by a heterophase mechanism.

  13. Solvolysis of benzoyl halides in water/NH4DEHP/isooctane microemulsions.

    PubMed

    García-Río, L; Hervella, P; Rodríguez-Dafonte, P

    2006-08-29

    A study was carried out on the solvolysis reactions of different benzoyl halides in microemulsions of water/NH4DEHP/isooctane, where NH4DEHP is ammonium bis(2-ethylhexyl) phosphate. Because of the low solubility of benzoyl halides in water, they are distributed between the continuous medium and the interface of the microemulsion, where the reaction takes place. The application of the pseudophase model has allowed us to obtain the distribution constants and the rate constants at the interface for the benzoyl halides. Reaction mechanisms and the changes in these mechanisms in terms of the water content of the microemulsion have been determined on the basis of kinetic data. The influence of the substituent and the leaving group on the reaction rate has been investigated. A comparison of kinetic results with those previously obtained in water/AOT/isooctane microemulsions allows a kinetic evaluation of the change in the microemulsion properties with the surfactant.

  14. Discovery of 4-Aryl-2-benzoyl-imidazoles As Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

    PubMed Central

    Xiao, Min; Ahn, Sunjoo; Wang, Jin; Chen, Jianjun; Miller, Duane. D.; Dalton, James T; Li, Wei

    2013-01-01

    A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogs. RABIs were evaluated for biological activity against 8 cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties with IC50 values in the low nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogs was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay and molecular docking studies. These studies confirmed that these new RABI analogs maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogs. PMID:23547728

  15. The barriers to internal rotation of benzaldehyde and benzoyl fluoride: "reconciliation" between theory and experiment.

    PubMed

    Godunov, Igor A; Bataev, Vadim A; Abramenkov, Alexander V; Pupyshev, Vladimir I

    2014-11-06

    This work is devoted to investigation of the known problem of the discrepancy between the experimental and theoretical values for the barrier to internal rotation of the molecules comprised of a benzene ring and a π-conjugated substituent, such as benzaldehyde and benzoyl fluoride. The possible reasons of such discrepancy are considered. As a result the conclusion was drawn that the origin of the problem is incorrectness of the assignments of the torsional levels higher than first, both for benzaldehyde and benzoyl fluoride. In addition the significant kinematic interaction between torsional vibration and out-of-plane CHO deformation was found for benzaldehyde.

  16. Vibrational overtone enhancement of methyl methacrylate polymerization initiated by benzoyl peroxide decomposition

    NASA Astrophysics Data System (ADS)

    Grinevich, Oleg; Snavely, D. L.

    1997-03-01

    Vibrational overtone initiated polymerization has been demonstrated using intracavity photolysis of a benzoyl peroxide/methyl methacrylate mixture. Excitation of the 6 νCH overtone transition of the ground electronic state of benzoyl peroxide creates radicals which subsequently begin the polymerization process. Polymer yield was monitored by comparison of the 2 νCH overtone absorptions for the methyl, methylenic and olefinic CH stretches at 5946 and 6170 cm -1, respectively. Plots of polymer yield versus time demonstrate an autoacceleration of the polymerization rate commencing many hours after the photolysis period. The delay before autoacceleration depends on the duration of the photolysis.

  17. Laser vibrational overtone activation of ethyl acrylate/benzoyl peroxide mixture

    NASA Astrophysics Data System (ADS)

    Grinevich, Oleg; Snavely, D. L.

    1999-04-01

    Intra- and extracavity laser vibrational overtone polymerization of ethyl acrylate/benzoyl peroxide mixture has been demonstrated. Five photolysis wavenumbers on and near the fifth CH stretch overtone absorption of benzoyl peroxide was investigated. The polymer yield was monitored by observing the decrease in the intensity ratio of the olefinic/methyl and methylenic first CH stretch overtone absorptions of ethyl acrylate. The rate of the polymerization did not depend on the photolysis wavenumber. Molecular weights of the overtone initiated polymers were an order of magnitude larger than those obtained by thermal polymerization. The polymerization rate is compared to the intracavity laser vibrational overtone polymerization of methyl methacrylate.

  18. Novel N-benzoyl-2-hydroxybenzamide disrupts unique parasite secretory pathway.

    PubMed

    Fomovska, Alina; Huang, Qingqing; El Bissati, Kamal; Mui, Ernest J; Witola, William H; Cheng, Gang; Zhou, Ying; Sommerville, Caroline; Roberts, Craig W; Bettis, Sam; Prigge, Sean T; Afanador, Gustavo A; Hickman, Mark R; Lee, Patty J; Leed, Susan E; Auschwitz, Jennifer M; Pieroni, Marco; Stec, Jozef; Muench, Stephen P; Rice, David W; Kozikowski, Alan P; McLeod, Rima

    2012-05-01

    Toxoplasma gondii is a protozoan parasite that can damage the human brain and eyes. There are no curative medicines. Herein, we describe our discovery of N-benzoyl-2-hydroxybenzamides as a class of compounds effective in the low nanomolar range against T. gondii in vitro and in vivo. Our lead compound, QQ-437, displays robust activity against the parasite and could be useful as a new scaffold for development of novel and improved inhibitors of T. gondii. Our genome-wide investigations reveal a specific mechanism of resistance to N-benzoyl-2-hydroxybenzamides mediated by adaptin-3β, a large protein from the secretory protein complex. N-Benzoyl-2-hydroxybenzamide-resistant clones have alterations of their secretory pathway, which traffics proteins to micronemes, rhoptries, dense granules, and acidocalcisomes/plant-like vacuole (PLVs). N-Benzoyl-2-hydroxybenzamide treatment also alters micronemes, rhoptries, the contents of dense granules, and, most markedly, acidocalcisomes/PLVs. Furthermore, QQ-437 is active against chloroquine-resistant Plasmodium falciparum. Our studies reveal a novel class of compounds that disrupts a unique secretory pathway of T. gondii, with the potential to be used as scaffolds in the search for improved compounds to treat the devastating diseases caused by apicomplexan parasites.

  19. Benzoyl-coenzyme A thioesterase of Azoarcus evansii: properties and function.

    PubMed

    Ismail, Wael

    2008-10-01

    The aerobic benzoate metabolism in Azoarcus evansii follows an unusual route. The intermediates of the pathway are processed as coenzyme A (CoA) thioesters and the cleavage of the aromatic ring is non-oxygenolytic. The enzymes of this pathway are encoded by the box gene cluster which harbors a gene, orf1, coding for a putative thioesterase. Benzoyl-CoA thioesterase activity (20 nmol min(-1) mg(-1) protein) was present in cells grown aerobically on benzoate, but was lacking in cells grown on other aromatic or aliphatic substrates under oxic or anoxic conditions. The gene was cloned and overexpressed in Escherichia coli to produce a C-terminal His-tag fusion protein. The recombinant enzyme was a homotetramer of 16 kDa subunits. It catalyzed not only the hydrolysis of benzoyl-CoA, but also of 2,3-dihydro-2,3-dihydroxybenzoyl-CoA, the second intermediate in the pathway. The enzyme exhibited higher activity with mono-substituted derivatives of benzoyl-CoA, showing highest activity with 4-hydroxybenzoyl-CoA. Di-substituted derivatives of benzoyl-CoA, phenylacetyl-CoA, and aliphatic CoA thioesters were not hydrolyzed but some acted as inhibitors. The thioesterase appears to protect the cell from CoA pool depletion. It may constitute the prototype of a new subfamily within the hotdog fold enzyme superfamily.

  20. Novel N-Benzoyl-2-Hydroxybenzamide Disrupts Unique Parasite Secretory Pathway

    PubMed Central

    Fomovska, Alina; Huang, Qingqing; El Bissati, Kamal; Mui, Ernest J.; Witola, William H.; Cheng, Gang; Zhou, Ying; Sommerville, Caroline; Roberts, Craig W.; Bettis, Sam; Prigge, Sean T.; Afanador, Gustavo A.; Hickman, Mark R.; Lee, Patty J.; Leed, Susan E.; Auschwitz, Jennifer M.; Pieroni, Marco; Stec, Jozef; Muench, Stephen P.; Rice, David W.; Kozikowski, Alan P.

    2012-01-01

    Toxoplasma gondii is a protozoan parasite that can damage the human brain and eyes. There are no curative medicines. Herein, we describe our discovery of N-benzoyl-2-hydroxybenzamides as a class of compounds effective in the low nanomolar range against T. gondii in vitro and in vivo. Our lead compound, QQ-437, displays robust activity against the parasite and could be useful as a new scaffold for development of novel and improved inhibitors of T. gondii. Our genome-wide investigations reveal a specific mechanism of resistance to N-benzoyl-2-hydroxybenzamides mediated by adaptin-3β, a large protein from the secretory protein complex. N-Benzoyl-2-hydroxybenzamide-resistant clones have alterations of their secretory pathway, which traffics proteins to micronemes, rhoptries, dense granules, and acidocalcisomes/plant-like vacuole (PLVs). N-Benzoyl-2-hydroxybenzamide treatment also alters micronemes, rhoptries, the contents of dense granules, and, most markedly, acidocalcisomes/PLVs. Furthermore, QQ-437 is active against chloroquine-resistant Plasmodium falciparum. Our studies reveal a novel class of compounds that disrupts a unique secretory pathway of T. gondii, with the potential to be used as scaffolds in the search for improved compounds to treat the devastating diseases caused by apicomplexan parasites. PMID:22354304

  1. Copper-Catalyzed Electrophilic Amination of Organoaluminum Nucleophiles with O-Benzoyl Hydroxylamines.

    PubMed

    Zhou, Shuangliu; Yang, Zhiyong; Chen, Xu; Li, Yimei; Zhang, Lijun; Fang, Hong; Wang, Wei; Zhu, Xiancui; Wang, Shaowu

    2015-06-19

    A copper-catalyzed electrophilic amination of aryl and heteroaryl aluminums with N,N-dialkyl-O-benzoyl hydroxylamines that affords the corresponding anilines in good yields has been developed. The catalytic reaction proceeds very smoothly under mild conditions and exhibits good substrate scope. Moreover, the developed catalytic system is also well suited for heteroaryl aluminum nucleophiles, providing facile access to heteroaryl amines.

  2. Copper(II)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines.

    PubMed

    Li, Gang; Jia, Chunqi; Sun, Kai; Lv, Yunhe; Zhao, Feng; Zhou, Kexiao; Wu, Hankui

    2015-03-21

    Copper acetate-catalyzed C-H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields. Electrophilic amination can also be performed in good yield on a gram scale.

  3. Mechanism of the oxidation of certain N-dialkylanilines by benzoyl peroxide

    SciTech Connect

    Titov, E.V.; Alaev, Yu.N.; Luk'yanenko, L.V.

    1986-03-01

    In the interaction of N-dialkylanilines with benzoyl peroxide there is a transfer of one electron with the formation of the corresponding radical cations. Radical cations of N,N'-tetraalkylbenzidines are formed as secondary conversion products of the radical cations of N-dialkylanilines, which exhibit paramagnetic properties.

  4. Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides.

    PubMed

    Sun, Meng; Wang, Zhe; Wang, Jiaxin; Guo, Peiyu; Chen, Xiangxiang; Li, Ya-Min

    2016-12-07

    A palladium catalyzed efficient strategy for regio-selective ortho-arylation of sulfoxides with benzoyl peroxides via decarboxylation has been developed. This reaction proceeds smoothly, tolerates a variety of functional groups, and provides easy access to the synthesis of different biaryl compounds.

  5. Investigation of the decomposition reaction and dust explosion characteristics of crystalline benzoyl peroxides.

    PubMed

    Lu, Kai-Tai; Chen, Ting-Chi; Hu, Kwan-Hua

    2009-01-15

    The benzoyl peroxide (BPO) is widely used in the chemical industry. Many catastrophes have been caused by its thermal instability or reactive incompatibility in storage or thermal decomposition reaction. Thus, its hazard characteristics have to be clearly identified. First of all, the differential scanning calorimeter (DSC) is used to measure the heat of decomposition reaction, which can contribute to understanding the reaction characteristics of benzoyl peroxide. The accelerating rate calorimeter (ARC) is used to measure the rates of temperature and pressure rises of decomposition reaction, and then the kinetics parameters are estimated. Furthermore, the MIKE 3 apparatus and the 20-l-Apparatus are used to measure and analyze the dust explosion characteristics of benzoyl peroxide under room temperature and atmospheric pressure. Finally, Semenov's thermal explosion theory is applied to investigate the critical runaway condition and the stability criterion of decomposition reaction, and to build the relationship of critical temperature, convective heat transfer coefficient, heat transfer surface area and ambient temperature. These results contribute to improving the safety in the reaction, transportation and storage processes of benzoyl peroxide.

  6. Temperature dependence of the enhancement factor of cidnp created by the photolysis of benzoyl peroxide

    NASA Astrophysics Data System (ADS)

    Takahashi, Satoshi; Terazima, Masahide; Azumi, Tohru

    1990-03-01

    The enhancement factor of the nuclear polarization created by the photolysis of benzoyl peroxide in CDCl 3 is measured at various temperatures. The experimental enhancement factor agrees with the theoretical value calculated by the theory proposed by Pedersen and Freed. Further, the temperature dependence of the enhancement factor is well interpreted by the continuous diffusion model.

  7. Enhancing intermolecular benzoyl-transfer reactivity in crystals by growing a "reactive" metastable polymorph by using a chiral additive.

    PubMed

    Murali, Chebrolu; Shashidhar, Mysore S; Gonnade, Rajesh G; Bhadbhade, Mohan M

    2009-01-01

    Racemic 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoacetate, which normally crystallizes in a monoclinic form (form I, space group P2(1)/n) could be persuaded to crystallize out as a metastable polymorph (form II, space group C2/c) by using a small amount of either D- or L- 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoformate as an additive in the crystallization medium. The structurally similar enantiomeric additive was chosen by the scrutiny of previous experimental results on the crystallization of racemic 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoacetate. Form II crystals can be thermally transformed to form I crystals at about 145 degrees C. The relative organization of the molecules in these dimorphs vary slightly in terms of the helical assembly of molecules, that is, electrophile (El)...nucleophile (Nu) and C-H...pi interactions, but these minor variations have a profound effect on the facility and specificity of benzoyl-group-transfer reactivity in the two crystal forms. While form II crystals undergo a clean intermolecular benzoyl-group-transfer reaction, form I crystals are less reactive and undergo non-specific benzoyl-group transfer leading to a mixture of products. The role played by the additive in fine-tuning small changes that are required in the molecular packing opens up the possibility of creating new polymorphs that show varied physical and chemical properties. Crystals of D-2,6-di-O-benzoyl-myo-inositol-1,3,5-orthoformate (additive) did not show facile benzoyl-group-transfer reactivity (in contrast to the corresponding racemic compound) due to the lack of proper juxtaposition and assembly of molecules.

  8. Europium luminescence in its complexes with 2-acetyl- and 2-benzoyl-1,3-indanediones

    SciTech Connect

    Vitkun, R.A.; Gerasimenko, T.M.; Ul'yanova, M.A.; Tishchenko, M.A.; Polyektov, N.S.

    1982-04-01

    We have previously studied the capacity of lanthanide ions to form complexes with the cyclic ..beta..-diketone, 2-acetyl-1,3-indanedione (AID). The complexation was studied spectrophotometrically for neodymium and erbium ions relative to change in the absorption bands corresponding to hyperfine transitions. The pH-potentiometric method was used to find the stability constants of the lanthanides with AID. The IR spectra of the coordination compounds of several lanthanides with 2-acetyl-1,3-indanedione and the thermal stability of these compounds were examined in our previous work. We found that the complexes of 2-acetyl-1,3-indanedione and 2-benzoyl-1,3-indanedione (BID) display strong luminescence upon their irradiation with ultraviolet light. The analogous compounds of samarium, terbium, and dysprosium have only weak luminescence. We carried out a luminescence study of the complexation of europium with 2-acetyl- and 2-benzoyl-1,3-indanedione.

  9. New neolignan glycoside and an unusual benzoyl malic acid derivative from Maytenus senegalensis leaves.

    PubMed

    Okoye, Festus Basden Chiedu; Agbo, Matthias Onyebuchi; Nworu, Chukwuemeka Sylvester; Nwodo, Ngozi Justina; Esimone, Charles Okechukwu; Osadebe, Patience Ogoamaka; Proksch, Peter

    2015-01-01

    Further investigation of the methanol leaf extract of Maytenus senegalensis led to the isolation of six compounds, including mayselignoside (1) and an unusual benzoyl malic acid derivative, benzoyl R-(+)-malic acid (2). Two known lignan derivatives (+)-lyoniresinol (3) and (-)-isolariciresinol (4), a known neolignan derivative dihydrodehydrodiconiferyl alcohol (5) and the triterpenoid, β-amyrin (6) were also isolated. The structures of these compounds were elucidated by a combination of 1D and 2D NMR and mass spectroscopy. All compounds were tested for cytotoxicity against mouse lymphoma cell line (L5178Y) and for antimicrobial activity against strains of bacteria and fungi. None of the compounds showed promising cytotoxic and/or antimicrobial activities.

  10. A method for benzoyl chloride derivatization of biogenic amines for high performance liquid chromatography.

    PubMed

    Ozdestan, Ozgül; Uren, Ali

    2009-06-15

    A new benzoylation procedure was developed which was more reliable than the most common benzoylation procedures in terms of reaction time, peak resolution, detector response and repeatability. Methylamine, putrescine, cadaverine, tryptamine, beta-phenylethylamine, spermidine, spermine, histamine, tyramine and agmatine were studied. Linearity for each biogenic amine was observed with a good regression coefficient. Limits of detection were found between 0.2mg/l and 2.5mg/l. Recovery rates varied from 72.8% to 103.4%. Temperature and pH of mobile phase were studied and found that 20 degrees C of column temperature with a pH of 8 was preferable. It was established that polyvinylpyrrolidone adsorbed biogenic amines and caused interference in HPLC determination of biogenic amines that had been used by some authors to eliminate interfering phenolic compounds in wine samples.

  11. Intense pulsed light versus benzoyl peroxide 5% gel in treatment of acne vulgaris.

    PubMed

    El-Latif, Azmy Ahmed Abd; Hassan, Faisal Abdel Aziz; Elshahed, Ahmed Rashad; Mohamed, Amr Ghareeb; Elsaie, Mohamed L

    2014-05-01

    Acne is a common disorder affecting the pilosebaceous unit. Despite many advances in the treatments of acne vulgaris the best option is still controversial as the pathogenesis of acne is rather complex, necessitating various combination therapies. The objective of this study is to compare the clinical efficacy of intense pulsed light therapy (IPL) versus benzoyl peroxide 5% for the treatment of inflammatory acne. Fifty patients of both sexes, (15 males and 35 females) aged (18-27 years), with mild-to-severe acne and Fitzpatrick skin phototype IV were enrolled in this study. The patients were equally divided into two groups. The first group was treated by benzoyl peroxide while the second group was treated by IPL. For both therapies, patients experienced a significant reduction in the mean of the inflammatory lesion counts over the treatment period. Comparing the effects of both therapies, BP produced better results than IPL. The difference in the results was statistically significant at the midpoint of the study. However, this difference was insignificant at the end of study. Treatment with both benzoyl peroxide and IPL resulted in considerable improvement of the acne after 5 weeks of treatment. Comparing the effects of both therapies, BP produced better results than IPL. The difference in the results was statistically significant at the midpoint of the study. However, this difference was insignificant at the end of study.

  12. The role of benzoyl peroxide in the new treatment paradigm for acne.

    PubMed

    Kircik, Leon H

    2013-06-01

    Bacterial resistance became a true clinical concern for dermatologists in the 1980s, when the first reports emerged of the resistance of Propionibacterium acnes to oral antibiotics. Subsequent studies have documented acne treatment failure associated with resistance to topical antibiotics. Beyond dermatology practice, antibiotic resistance has now become recognized as a worldwide health concern. In contrast to antibiotics commonly used in the treatment of acne, benzoyl peroxide (BP)'s mechanism of action is different. Benzoyl peroxide is a bactericidal agent. Combining BP with a topical antibiotic in a stable formulation has been proven in clinical trials to reduce total P acnes count by 99.7% after 1 week of therapy, eliminating both susceptible and resistant strains of P acnes. However, we have recently noticed BP's benefits as monotherapy in the treatment of acne. Benzoyl peroxide works rapidly on P acnes without causing antibiotic resistance. Hence, we may have to reconsider the role of topical antibiotics such as clindamycin in the treatment paradigm of acne vulgaris.

  13. Analysis of benzoyl-peroxide and formaldehyde as dental allergens by FT-SPR method

    NASA Astrophysics Data System (ADS)

    Bako, J.; Kelemen, M.; Hegedus, Cs

    2013-12-01

    In parallel with the appearance of new dental materials the number of induced allergic diseases increases. Based on this fact more sensitive detection of allergens is major importance. The Fourier-Transform Surface Plasmon Resonance (FT-SPR) is a sensitive, broadly applicable real-time method for analysing thin layers of materials on gold surfaces. FT-SPR measurement is performed at a fixed angel of incident light, and reflectivity is measured over a range of wavelength in the near infrared. In our study the formaldehyde and benzoyl-peroxide were examined as members of the most common dental allergens by FT-SPR spectroscopy. The aim of this work was the investigation of the suitability of this method for the direct detection of these materials. Different concentrations of formaldehyde and benzoyl-peroxide solutions were measured from this purpose. The individual spectra were measured for all of the solutions, and calibration curves were calculated for the materials for the possibility of the determination of an unknown concentration. In addition, series measurements were performed whereby the association and dissociation properties of formaldehyde or benzoyl-peroxide were described. The results of the experiments proved that the method capable to measure directly these materials and can provide appropriate calibration curves for determination of unknown concentrations.

  14. Thermochemistry and reaction paths in the oxidation reaction of benzoyl radical: C6H5C•(═O).

    PubMed

    Sebbar, Nadia; Bozzelli, Joseph W; Bockhorn, Henning

    2011-10-27

    Alkyl substituted aromatics are present in fuels and in the environment because they are major intermediates in the oxidation or combustion of gasoline, jet, and other engine fuels. The major reaction pathways for oxidation of this class of molecules is through loss of a benzyl hydrogen atom on the alkyl group via abstraction reactions. One of the major intermediates in the combustion and atmospheric oxidation of the benzyl radicals is benzaldehyde, which rapidly loses the weakly bound aldehydic hydrogen to form a resonance stabilized benzoyl radical (C6H5C(•)═O). A detailed study of the thermochemistry of intermediates and the oxidation reaction paths of the benzoyl radical with dioxygen is presented in this study. Structures and enthalpies of formation for important stable species, intermediate radicals, and transition state structures resulting from the benzoyl radical +O2 association reaction are reported along with reaction paths and barriers. Enthalpies, ΔfH298(0), are calculated using ab initio (G3MP2B3) and density functional (DFT at B3LYP/6-311G(d,p)) calculations, group additivity (GA), and literature data. Bond energies on the benzoyl and benzoyl-peroxy systems are also reported and compared to hydrocarbon systems. The reaction of benzoyl with O2 has a number of low energy reaction channels that are not currently considered in either atmospheric chemistry or combustion models. The reaction paths include exothermic, chain branching reactions to a number of unsaturated oxygenated hydrocarbon intermediates along with formation of CO2. The initial reaction of the C6H5C(•)═O radical with O2 forms a chemically activated benzoyl peroxy radical with 37 kcal mol(-1) internal energy; this is significantly more energy than the 21 kcal mol(-1) involved in the benzyl or allyl + O2 systems. This deeper well results in a number of chemical activation reaction paths, leading to highly exothermic reactions to phenoxy radical + CO2 products.

  15. Genes coding for the benzoyl-CoA pathway of anaerobic aromatic metabolism in the bacterium Thauera aromatica.

    PubMed

    Breese, K; Boll, M; Alt-Mörbe, J; Schägger, H; Fuchs, G

    1998-08-15

    Many aromatic compounds are anaerobically oxidized to CO2 via benzoyl-CoA as the common aromatic intermediate. In Thauera aromatica, the central benzoyl-CoA pathway comprises the ATP-driven two-electron reduction of the benzene ring; this reaction uses a ferredoxin as electron donor and is catalyzed by benzoyl-CoA reductase. The first intermediate, cyclohex-1,5-diene-1-carboxyl-CoA, is subsequently hydrated by dienoyl-CoA hydratase to 6-hydroxycyclohex-1-ene-1-carboxyl-CoA. Formation of the main product produced by cell extracts, 3-hydroxypimelyl-CoA, requires at least two further steps; the oxidation of a hydroxyl group and the hydrolytic carbon ring cleavage of a CoA-activated beta-oxoacid. In addition, enoyl-CoA hydratase may come into play. A cluster of eight adjacent genes, which are transcribed in the same direction and may form an operon, was found in this bacterium. The cluster codes for proven and postulated enzymes of the benzoyl-CoA pathway. The genes for the enzymes code for ferredoxin, four subunits of benzoyl-CoA reductase, dienoyl-CoA hydratase, 6-hydroxycyclohex-1-ene-1-carboxyl-CoA dehydrogenase (NAD+), and the ring hydrolyzing enzyme. The deduced amino acid sequences of these proteins were 35-86% similar to the corresponding sequences found in Rhodopseudomonas palustris. Benzoyl-CoA reductase subunits exhibit distinct similarities with 2-hydroxyglutaryl-CoA dehydratase and its ATP-hydrolysing activase protein of Acidaminococcus fermentans as well as with open reading frames of unknown function in other bacteria. Conversion of benzoyl-CoA to 3-hydroxypimelyl-CoA can be explained by a minimal model of the benzoyl-CoA pathway assuming the four enzymes whose genes were characterized and an additional enoyl-CoA hydratase. In R. palustris the dienoyl-CoA hydratase gene is lacking suggesting the operation of a modified benzoyl-CoA pathway with cyclohex-1-ene-1-carboxyl-CoA as intermediate.

  16. Profile of clindamycin phosphate 1.2%/benzoyl peroxide 3.75% aqueous gel for the treatment of acne vulgaris

    PubMed Central

    Nguyen, Tuyet A; Eichenfield, Lawrence F

    2015-01-01

    Acne vulgaris is a common and chronic skin disease, and is a frequent source of morbidity for affected patients. Treatment of acne vulgaris is often difficult due to the multifactorial nature of this disease. Combination therapy, such as that containing clindamycin and benzoyl peroxide, has become the standard of care. Several fixed formulations of clindamycin 1% and benzoyl peroxide of varying concentrations are available and have been used with considerable success. The major limitation is irritation and dryness from higher concentrations of benzoyl peroxide, and a combination providing optimal efficacy and tolerability has yet to be determined. Recently, a clindamycin and benzoyl peroxide 3.75% fixed combination formulation was developed. Studies have suggested that this formulation may be a safe and effective treatment regimen for patients with acne vulgaris. Here, we provide a brief review of acne pathogenesis, benzoyl peroxide and clindamycin, and profile a new Clindamycin-BP 3.75% fixed combination gel for the treatment of moderate-to-severe acne vulgaris. PMID:26604811

  17. Profile of clindamycin phosphate 1.2%/benzoyl peroxide 3.75% aqueous gel for the treatment of acne vulgaris.

    PubMed

    Nguyen, Tuyet A; Eichenfield, Lawrence F

    2015-01-01

    Acne vulgaris is a common and chronic skin disease, and is a frequent source of morbidity for affected patients. Treatment of acne vulgaris is often difficult due to the multifactorial nature of this disease. Combination therapy, such as that containing clindamycin and benzoyl peroxide, has become the standard of care. Several fixed formulations of clindamycin 1% and benzoyl peroxide of varying concentrations are available and have been used with considerable success. The major limitation is irritation and dryness from higher concentrations of benzoyl peroxide, and a combination providing optimal efficacy and tolerability has yet to be determined. Recently, a clindamycin and benzoyl peroxide 3.75% fixed combination formulation was developed. Studies have suggested that this formulation may be a safe and effective treatment regimen for patients with acne vulgaris. Here, we provide a brief review of acne pathogenesis, benzoyl peroxide and clindamycin, and profile a new Clindamycin-BP 3.75% fixed combination gel for the treatment of moderate-to-severe acne vulgaris.

  18. Clindamycin Phosphate 1.2% and Benzoyl Peroxide 2.5% Gel for the Treatment of Moderate-to-severe Acne: An Update.

    PubMed

    Gold, Michael H

    2012-01-01

    The use of fixed-combination products in acne is commonplace. Clindamycin and benzoyl peroxide are often used in combination, but benzoyl peroxide can cause irritation and dryness, sometimes limiting use. The true bothersome nature of this concentration-dependent tolerability has only recently been elucidated and is significant. An optimized formulation of clindamycin-benzoyl peroxide containing 2.5% benzoyl peroxide has been shown to be highly effective and well-tolerated when used to treat moderate-to-severe acne. A meta-analysis has shown clindamycin phosphate 1.2%-benzoyl peroxide 2.5% gel to be as effective as combinations containing 5% benzoyl peroxide, with possibly greater efficacy in treating noninflammatory lesions. Efficacy in moderate-to-severe and adolescent subpopulations has also been highlighted. Clinical objective assessments, such as lesion counts and physician grading classifications, alone do not adequately capture the impact of acne severity from a patient's perspective. Clindamycin phosphate 1.2%-benzoyl peroxide 2.5% has shown a high level of patient satisfaction and significant improvement in all four acne quality of life domains. This review brings together some of the most recent work on clindamycin phosphate 1.2%-benzoyl peroxide 2.5% gel from one of the most extensive clinical programs ever in moderate-to-severe acne.

  19. Biosynthesis of benzoylformic acid from benzoyl cyanide with a new bacterial isolate of Brevibacterium sp. CCZU12-1.

    PubMed

    He, Yu-Cai; Pan, Xue-He; Xu, Xiao-Feng; Wang, Li-Qun

    2014-03-01

    Brevibacterium sp. CCZU12-1 with high nitrilase activity could effectively hydrolyze benzoyl cyanide into benzoylformic acid. After the culture optimization, the preferred carbon sources, nitrogen sources, and inducer were glucose (10 g/L), a composite of peptone (10 g/L) plus yeast extract (2.5 g/L), and ε-caprolactam (2.0 mM), respectively. After the reaction optimization, the optimum reaction temperature, reaction pH, organic cosolvent, and metal ion were 30 °C, 7.0, ethanol (2%, v/v), and Ca(2+) (0.1 mM), respectively. At biotransformation of 120-mM benzoyl cyanide for 24 h, the yield of benzoylformic acid reached 91.8%. Moreover, the microbial nitrilase from Brevibacterium sp. CCZU12-1 could hydrolyze various nitriles, and it significantly exhibited high nitrilase activity against benzoyl cyanide, 3-cyanopyridine, and α-cyclohexyl-mandelonitrile.

  20. A case of pyoderma gangrenosum stabilized with lymecycline, topical benzoyl peroxide and treated by autograft.

    PubMed

    Vereecken, P; Wautrecht, J C; De Dobbeleer, G; Heenen, M

    1997-01-01

    Pyoderma gangrenosum is a chronic inflammatory ulcerative skin disease of unknown etiology, often associated with various systemic disorders such as inflammatory bowel disease, rheumatoid arthritis, chronic active hepatitis, diabetes mellitus and hematologic malignancies. The ulcers are characterized by their undermined violaceous borders. The disease remains a therapeutic challenge. Corticosteroids are the mainstay of therapy; however, side effects from this treatment and recalcitrant pyoderma gangrenosum require therapeutic alternatives. We report the case of a large subacute pyoderma gangrenosum stabilized with lymecycline, topical benzoyl peroxide and successfully treated by an autograft. This observation supports the opinion that the risk of pathergy of a graft can be avoided by the stabilization of the disease.

  1. Sensory and Functionality Differences of Whey Protein Isolate Bleached by Hydrogen or Benzoyl Peroxide.

    PubMed

    Smith, Tucker J; Foegeding, E Allen; Drake, MaryAnne

    2015-10-01

    Whey protein is a highly functional food ingredient used in a wide variety of applications. A large portion of fluid whey produced in the United States is derived from Cheddar cheese manufacture and contains annatto (norbixin), and therefore must be bleached. The objective of this study was to compare sensory and functionality differences between whey protein isolate (WPI) bleached by benzoyl peroxide (BP) or hydrogen peroxide (HP). HP and BP bleached WPI and unbleached controls were manufactured in triplicate. Descriptive sensory analysis and gas chromatography-mass spectrometry were conducted to determine flavor differences between treatments. Functionality differences were evaluated by measurement of foam stability, protein solubility, SDS-PAGE, and effect of NaCl concentration on gelation relative to an unbleached control. HP bleached WPI had higher concentrations of lipid oxidation and sulfur containing volatile compounds than both BP and unbleached WPI (P < 0.05). HP bleached WPI was characterized by high aroma intensity, cardboard, cabbage, and fatty flavors, while BP bleached WPI was differentiated by low bitter taste. Overrun and yield stress were not different among WPI (P < 0.05). Soluble protein loss at pH 4.6 of WPI decreased by bleaching with either hydrogen peroxide or benzoyl peroxide (P < 0.05), and the heat stability of WPI was also distinct among WPI (P < 0.05). SDS PAGE results suggested that bleaching of whey with either BP or HP resulted in protein degradation, which likely contributed to functionality differences. These results demonstrate that bleaching has flavor effects as well as effects on many of the functionality characteristics of whey proteins. Whey protein isolate (WPI) is often used for its functional properties, but the effect of oxidative bleaching chemicals on the functional properties of WPI is not known. This study identifies the effects of hydrogen peroxide and benzoyl peroxide on functional and flavor characteristics of WPI

  2. A Review of the Safety and Efficacy of Benzoyl Peroxide (5.3%) Emollient Foam in the Management of Truncal Acne Vulgaris

    PubMed Central

    2010-01-01

    This article reviews findings of studies regarding the treatment of truncal acne with benzoyl peroxide formulations and, in particular, studies utilizing a 5.3% benzoyl peroxide foam. Its formulation of micronized benzoyl peroxide particles in an emollient foam vehicle offers significant clinical and bioavailability advantages that enhance follicular penetration and skin moisturization. A key consideration for topical management of truncal acne is whether the treatment application method allows adequate skin contact time to reduce Propionibacterium acnes colony counts. The foam formulation has demonstrated significant reduction in Propionibacterium acnes on the back when used either as a leave-on or as short-contact therapy for five minutes. Short-contact therapy with a benzoyl peroxide foam is a novel approach to minimize the risk of benzoyl peroxide bleaching of clothing in truncal acne patients. PMID:21103313

  3. A review of the safety and efficacy of benzoyl peroxide (5.3%) emollient foam in the management of truncal acne vulgaris.

    PubMed

    Bikowski, Joseph

    2010-11-01

    This article reviews findings of studies regarding the treatment of truncal acne with benzoyl peroxide formulations and, in particular, studies utilizing a 5.3% benzoyl peroxide foam. Its formulation of micronized benzoyl peroxide particles in an emollient foam vehicle offers significant clinical and bioavailability advantages that enhance follicular penetration and skin moisturization. A key consideration for topical management of truncal acne is whether the treatment application method allows adequate skin contact time to reduce Propionibacterium acnes colony counts. The foam formulation has demonstrated significant reduction in Propionibacterium acnes on the back when used either as a leave-on or as short-contact therapy for five minutes. Short-contact therapy with a benzoyl peroxide foam is a novel approach to minimize the risk of benzoyl peroxide bleaching of clothing in truncal acne patients.

  4. Structural, antimicrobial and computational characterization of 1-benzoyl-3-(5-chloro-2-hydroxyphenyl)thiourea

    NASA Astrophysics Data System (ADS)

    Atiş, Murat; Karipcin, Fatma; Sarıboğa, Bahtiyar; Taş, Murat; Çelik, Hasan

    2012-12-01

    A new thiourea derivative, 1-benzoyl-3-(5-chloro-2-hydroxyphenyl)thiourea (bcht) has been synthesized from the reaction of 2-amino-4-chlorophenol with benzoyl isothiocyanate. The title compound has been characterized by elemental analyses, FT-IR, 13C, 1H NMR spectroscopy and the single crystal X-ray diffraction analysis. The structure of bcht derived from X-ray diffraction of a single crystal has been presented. The structural and spectroscopic data of the molecule in the ground state were calculated by using density functional method using 6-311++G(d,p) basis set. The complete assignments of all vibrational modes were performed on the basis of the total energy distributions (TED). Isotropic chemical shifts (13C NMR and 1H NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. Theoretical calculations of bond parameters, harmonic vibration frequencies and nuclear magnetic resonance are in good agreement with experimental results. The UV absorption spectra of the compound that dissolved in ACN and MeOH were recorded. Bcht was also screened for antimicrobial activity against pathogenic bacteria and fungi.

  5. Matrix isolation, time-resolved IR, and computational study of the photochemistry of benzoyl azide

    SciTech Connect

    Pritchina, Elena A.; Gritsan, Nina; Maltsev, Alexander; Bally, Thomas; Autrey, Thomas; Liu, Yonglin; Wang, Yuhong; Toscano, John P.

    2003-06-01

    It was shown recently on the basis of DFT calculations (N. P. Gritsan and E. A. Pritchina, Mendeleev Commun., 2001, 11, 94) that the singlet states of aroylnitrenes undergo tremendous stabilization due to an extra N-O bonding interaction. To test experimentally the multiplicity and the structure of the lowest state of benzoylnitrenes we performed a study of their photochemistry in Ar matrices at 12 K. Formation of two species was observed on irradiation of benzoyl azide (1b) and its 4-acetyl derivative (1c). One of these species has an IR spectrum, which is consistent with that of isocyanate (2b,c). The IR and UV spectra of the second intermediate are in very good agreement with the calculated spectra of the singlet species (3b,c), whose structure is intermediate between that of a carbonylnitrene and an oxazirene. We further examined the photochemistry of benzoyl azide in solution at ambient temperatures by nanosecond time-resolved IR methods and obtained additional evidence for the singlet ground state of benzoylnitrene as well as insight into its reactivity in acetonitrile, cyclohexane, and dichloromethane. The above experiments were accompanied by quantum chemical calculations which included also a thorough investigation of the parent species, formylnitrene, at different levels of theory.

  6. Novel antimicrobial superporous cross-linked chitosan/pyromellitimide benzoyl thiourea hydrogels.

    PubMed

    Mohamed, Nadia A; Abd El-Ghany, Nahed A; Fahmy, Mona M

    2016-01-01

    In this work, chitosan (CS) was cross-linked with different amounts of pyromellitimide benzoyl thiourea moieties. The structure of the cross-linked CS was confirmed by elemental analyses, FTIR and (1)H- NMR spectroscopy. The cross-linking process proceeds via reacting of the amino groups of CS with the isothiocyanate groups of the N,N'-bis [4-(isothiocyanate carbonyl)phenyl] pyromellitimide cross-linker. The amount of the cross-linker was varied with respect to CS to produce four new pyromellitimide benzoyl thiourea cross-linked CS (PIBTU-CS) hydrogels designated as PIBTU-CS-1, PIBTU-CS-2, PIBTU-CS-3, and PIBTU-CS-4 of increasing cross-linking degree percent of 11, 22, 44 and 88%, respectively. The scanning electron microscopy observation indicates the extremely porous structure of the hydrogels. XRD results showed that the crystallinity of CS was decreased upon cross-linking. The four hydrogels exhibit a higher antibacterial activity on Bacillus subtilis and Streptococcus pneumoniae as Gram positive bacteria and against Escherichia coli as Gram negative bacteria and higher antifungal activity on Aspergillus fumigatus, Syncephalastrum racemosum and Geotricum candidum than that of the parent CS as shown from their higher inhibition zone diameters and their lower MIC values. The swell ability of the hydrogel as well as their antimicrobial activity increased with increasing cross-linking density.

  7. Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae.

    PubMed

    Sfara, Valeria; De Licastro, Susana A; Masuh, Hector M; Seccacini, Emilia A; Alzogaray, Raul A; Zerba, Eduardo N

    2007-03-01

    Emulsifiable concentrate formulations of 2 insect growth regulator (IGR) benzoyl ureas (novaluron and diflubenzuron) and the pyrethroid cis-permethrin were individually bioassayed against late 3rd- or early 4th-stage larvae of susceptible Aedes aegypti. The emergence inhibition 50% were 0.038, 0.048, and 0.179 ppb for novaluron, diflubenzuron, and cis-permethrin, respectively. We also tested 1:1 (v:v) mixtures of cis-permethrin and benzoyl ureas. Emergence inhibition 50% for novaluron plus cis-permethrin and diflubenzuron plus cis-permethrin were 0.030 and 0.037, respectively, with combination indexes of 0.49 and 0.56, indicating a synergistic interaction between these insecticides. The percentage of larval mortality produced by 0.5 ppb of the mixtures of cis-permethrin and each IGR was compared to the addition of larval mortality produced in separated experiments by 0.25 ppb of each component, after 5, 9 and 13 days of continuous exposure. In all bioassays, the novaluron plus cis-permethrin mixture produced a significantly higher larvicidal effect (P < 0.05) compared with the individual contribution of each compound. The diflubenzuron plus cis-permethrin mixture showed significantly higher larval mortality (P < 0.05) compared with the contributive effect of each insecticide after 9 and 13 days of exposure, but there was no significant difference after 5 days of exposure.

  8. Structural, antimicrobial and computational characterization of 1-benzoyl-3-(5-chloro-2-hydroxyphenyl)thiourea.

    PubMed

    Atiş, Murat; Karipcin, Fatma; Sarıboğa, Bahtiyar; Taş, Murat; Çelik, Hasan

    2012-12-01

    A new thiourea derivative, 1-benzoyl-3-(5-chloro-2-hydroxyphenyl)thiourea (bcht) has been synthesized from the reaction of 2-amino-4-chlorophenol with benzoyl isothiocyanate. The title compound has been characterized by elemental analyses, FT-IR, (13)C, (1)H NMR spectroscopy and the single crystal X-ray diffraction analysis. The structure of bcht derived from X-ray diffraction of a single crystal has been presented. The structural and spectroscopic data of the molecule in the ground state were calculated by using density functional method using 6-311++G(d,p) basis set. The complete assignments of all vibrational modes were performed on the basis of the total energy distributions (TED). Isotropic chemical shifts ((13)C NMR and (1)H NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. Theoretical calculations of bond parameters, harmonic vibration frequencies and nuclear magnetic resonance are in good agreement with experimental results. The UV absorption spectra of the compound that dissolved in ACN and MeOH were recorded. Bcht was also screened for antimicrobial activity against pathogenic bacteria and fungi.

  9. Comparison of a chlorhexidine and a benzoyl peroxide shampoo as sole treatment in canine superficial pyoderma.

    PubMed

    Loeffler, A; Cobb, M A; Bond, R

    2011-09-03

    The clinical and antibacterial efficacy of two shampoos used as a sole antibacterial treatment in dogs with superficial pyoderma were investigated and compared. In a randomised, partially blinded study, a 3 per cent chlorhexidine gluconate shampoo (Chlorhex 3; Leo Animal Health) was compared against a 2.5 per cent benzoyl peroxide shampoo (Paxcutol; Virbac) in 22 dogs with superficial pyoderma. Dogs were washed two to three times weekly with a 10-minute contact time over 21 days. Clinical scores and bacterial counts were assessed on days 1, 8 and 22 and compared within and between treatment groups; overall response was assessed at the end of the study. Twenty dogs completed the study; 15 (68.2 per cent) showed an overall clinical improvement and the clinical signs resolved in three chlorhexidine-treated dogs. In the chlorhexidine-treated group, scores for papules/pustules (P<0.001), investigator-assessed pruritus (P=0.003), total bacterial counts (P=0.003) and counts for coagulase-positive staphylococci (P=0.003) were reduced after three weeks. Scores and bacterial counts did not vary significantly in the benzoyl peroxide-treated group.

  10. Topical 5% benzoyl peroxide and 3% erythromycin gel: experience with 191 patients with papulopustular acne.

    PubMed

    Rallis, Efstathios; Verros, Constantinos; Katoulis, Alexandros; Katsarou, Alexandra

    2013-01-01

    Acne is the most common skin disease, with a relative prevalence of 85%-100% among young individuals. It affects the cosmetic appearance of the patients provoking severe distress. A number of different topical treatments have been used for the treatment of acne. In this study, we investigated the efficacy and safety of the topical treatment with 5% benzoyl peroxide and 3% erythromycin gel in patients with papulopustular acne. One hundred and ninety-one patients with inflammatory acne completed the study. The patients included 54 males and 137 females, mean age 22.3 ± 8.1 years. Topical gel was applied on the face once daily for 3 months. The mean number of non-inflammatory and inflammatory lesions after 3 months of therapy decreased significantly with respect to baseline, with a mean percentage reduction of the non-inflammatory and inflammatory lesions by 42.2% and 57.5%, respectively. In conclusion, topical 5% benzoyl peroxide and erythromycin 3% as monotherapy is efficient for the treatment of papulopustular acne.

  11. 2-Benzoyl-6-benzylidenecyclohexanone analogs as potent dual inhibitors of acetylcholinesterase and butyrylcholinesterase.

    PubMed

    Leong, Sze Wei; Abas, Faridah; Lam, Kok Wai; Shaari, Khozirah; Lajis, Nordin H

    2016-08-15

    In the present study, a series of 2-benzoyl-6-benzylidenecyclohexanone analogs have been synthesized and evaluated for their anti-cholinesterase activity. Among the forty-one analogs, four compounds (38, 39, 40 and 41) have been identified as lead compounds due to their highest inhibition on both AChE and BChE activities. Compounds 39 and 40 in particular exhibited highest inhibition on both AChE and BChE with IC50 values of 1.6μM and 0.6μM, respectively. Further structure-activity relationship study suggested that presence of a long-chain heterocyclic in one of the rings played a critical role in the dual enzymes' inhibition. The Lineweaver-Burk plots and docking results suggest that both compounds could simultaneously bind to the PAS and CAS regions of the enzyme. ADMET analysis further confirmed the therapeutic potential of both compounds based upon their high BBB-penetrating. Thus, 2-benzoyl-6-benzylidenecyclohexanone containing long-chain heterocyclic amine analogs represent a new class of cholinesterase inhibitor, which deserve further investigation for their development into therapeutic agents for cognitive diseases such as Alzheimer.

  12. Quantitative detection of benzoyl peroxide in wheat flour by line-scan macro-scale Raman chemical imaging

    USDA-ARS?s Scientific Manuscript database

    A high-throughput Raman chemical imaging method was developed for direct inspection of benzoyl peroxide (BPO) mixed in wheat flour. A 5 W 785 nm line laser (240 mm long and 1 mm wide) was used as a Raman excitation source in a push-broom Raman imaging system. Hyperspectral Raman images were collecte...

  13. An IR Study of Benzoyl Chloride Adsorbed on KA, NaA, and CaA Zeolites

    NASA Astrophysics Data System (ADS)

    Bardakçı, B.; Bahçeli, Semiha

    2005-09-01

    Infrared spectroscopy has been used to investigate the adsorption of liquid benzoyl chloride on A-type zeolites. The data show that at room temperature the Fermi resonance phenomenon occurs in the adsorption on KA, NaA and CaA zeolites which are little acidic aluminosilicates.

  14. cis-Bis(N-benzoyl-N′,N′-dibenzyl­thio­ureato-κ2 O,S)nickel(II)

    PubMed Central

    Pérez, Hiram; Corrêa, Rodrigo S.; Duque, Julio; Plutín, Ana M.; O’Reilly, Beatriz

    2008-01-01

    In the title compound, [Ni(C22H19N2OS)2], the NiII atom is coordinated by the S and O atoms of two N-benzoyl-N′,N′-dibenzyl­thio­ureate ligands in a slightly distorted square-planar geometry. The two O atoms are cis, as are the two S atoms. PMID:21202775

  15. Adapalene 0.1%/benzoyl peroxide 2.5% gel: a review of its use in the treatment of acne vulgaris in patients aged ≥ 12 years.

    PubMed

    Keating, Gillian M

    2011-12-01

    Adapalene 0.1%/benzoyl peroxide 2.5% gel (Epiduo™, Tactuo™) is the only fixed-dose combination product available that combines a topical retinoid with benzoyl peroxide; it targets three of the four main pathophysiologic factors in acne. This article reviews the therapeutic efficacy and tolerability of topical adapalene 0.1%/benzoyl peroxide 2.5% gel in the treatment of patients aged ≥ 12 years with acne vulgaris, as well as summarizing its pharmacologic properties. In three 12-week trials in patients aged ≥ 12 years with moderate acne, success rates were significantly higher with adapalene 0.1%/benzoyl peroxide 2.5% gel than with adapalene 0.1% gel or benzoyl peroxide 2.5% gel alone, and combination therapy had an earlier onset of action. In addition, significantly greater reductions in total, inflammatory, and noninflammatory lesion counts were seen in patients receiving adapalene 0.1%/benzoyl peroxide 2.5% gel than in those receiving adapalene 0.1% gel or benzoyl peroxide 2.5% gel alone. Adapalene 0.1%/benzoyl peroxide 2.5% gel did not significantly differ from clindamycin 1%/benzoyl peroxide 5% gel in terms of the reduction in the inflammatory, noninflammatory, or total lesion counts in patients with mild to moderate acne, according to the results of a 12-week trial. Twelve-week studies showed that topical adapalene 0.1%/benzoyl peroxide 2.5% gel in combination with oral lymecycline was more effective than oral lymecycline alone in patients with moderate to severe acne, and topical adapalene 0.1%/benzoyl peroxide 2.5% gel in combination with oral doxycycline hyclate was more effective than oral doxycycline hyclate alone in patients with severe acne. In patients with severe acne who responded to 12 weeks' therapy with topical adapalene 0.1%/benzoyl peroxide 2.5% gel plus oral doxycycline hyclate or oral doxycycline hyclate alone, an additional 6 months' therapy with adapalene 0.1%/benzoyl peroxide 2.5% gel was more effective than vehicle gel at

  16. Efficacy of benzoyl peroxide (5.3%) emollient foam and benzoyl peroxide (8%) wash in reducing Propionibacterium acnes on the back.

    PubMed

    Leyden, James J

    2010-06-01

    Topical treatment of acne vulgaris on the back is challenging largely due to the extensive broad surface with difficult to reach areas. A "leave-on" foam is suited for application to the trunk due to ease of application and spreadability. Prior to this trial, no data on Propionibacterium acnes (P. acnes) reduction on the back has existed for any benzoyl peroxide (BP) formulations or other acne treatments. To evaluate the effectiveness of BP (5.3%) emollient foam and BP (8%) wash in reducing P. acnes levels on the back. Five-week open-label single-center study of 20 healthy subjects (> 18 years old), colonized with P. acnes on their backs (> 10,000 colonies per cm2). Subjects were treated once daily with BP (5.3%) foam for two weeks; no treatment in week 3, and BP (8%) wash once daily for two further weeks. Quantitative bacteriologic cultures obtained at baseline and weeks 1, 2, 3, 5 and 6. Nineteen evaluable patients. Total P. acnes counts were reduced by 1.9 log (one week) and 2.1 log (two weeks) with BP (5.3%) emollient foam. BP (8%) wash did not reduce P. acnes counts after two weeks. BP (5.3%) emollient foam was superior to BP (8%) wash in reducing P. acnes on the back. The lack of effect of BP (8%) wash is surprising in view of the demonstrated results on the face and warrants further study.

  17. GC-MS and FTIR evaluation of the six benzoyl-substituted-1-pentylindoles: isomeric synthetic cannabinoids.

    PubMed

    Smith, Forrest T; DeRuiter, Jack; Abdel-Hay, Karim; Clark, C Randall

    2014-11-01

    This report compares the GC-MS and FTIR properties of all 6 regioisomeric benzoyl substituted-1-n-pentylindoles. These compounds have the benzoyl-group attached at each of the possible ring substituent positions of the indole ring. The six compounds have the same elemental composition C20H21NO yielding identical nominal and exact masses. Additionally, the substituents attached to the indole ring, benzoyl- and 1-n-pentyl-groups, are identical for all six isomers. The electron ionization mass spectra show equivalent regioisomeric major fragments resulting from cleavage of the groups attached to the central indole nucleus. Fragment ions occur at m/z 77 and 105 for the phenyl and benzoyl cations common to all six regioisomeric substances. Fragmentation of the benzoyl and/or pentyl groups yields the cations at m/z 234, 220, 214, 186 and 144. While the relative abundance of the ions varies among the six regioisomeric substances the 1-n-pentyl-3-benzoylindole and 1-n-pentyl-5-benzoylindole share very similar relative abundances for the major fragment ions. Chromatographic separations on a capillary column containing a 0.5μm film of 100% trifluoropropyl methyl polysiloxane (Rtx-200) provided excellent resolution of these six compounds. The elution order appears related to the relative distance between the two indole substituted groups. The latest eluting compounds (highest retention time) have the two substituents on opposite sides of the indole nucleus. Infrared absorption spectral data show the carbonyl absorption band for each of the benzoylindoles and provide distinguishing and characteristic information to individualize each of the regioisomers in this set of compounds. Copyright © 2014 Elsevier B.V. All rights reserved.

  18. N-Benzoyl-N′,N′′-dicyclo­hexyl­phospho­ric triamide

    PubMed Central

    Pourayoubi, Mehrdad; Rostami Chaijan, Mahnaz; Torre-Fernández, Laura; García-Granda, Santiago

    2011-01-01

    In the title compound, C19H30N3O2P, the central P atom has a distorted tetra­hedral configuration. The N atoms in both cyclo­hexyl­amide moieties exhibit a slight deviation [0.32 (7) and 0.44 (6) Å] from planarity, while the benzoyl­amide N atom is planar [0.11 (3) Å]. In the crystal, mol­ecules are linked via N—H⋯O(P) and N—H⋯O(C) hydrogen bonds, forming R 2 2(10) rings within linear arrangements parallel to the b axis. PMID:21754754

  19. Design and synthesis of N-benzoyl amino acid derivatives as DNA methylation inhibitors.

    PubMed

    Garella, Davide; Atlante, Sandra; Borretto, Emily; Cocco, Mattia; Giorgis, Marta; Costale, Annalisa; Stevanato, Livio; Miglio, Gianluca; Cencioni, Chiara; Fernández-de Gortari, Eli; Medina-Franco, José L; Spallotta, Francesco; Gaetano, Carlo; Bertinaria, Massimo

    2016-11-01

    The inhibition of human DNA Methyl Transferases (DNMT) is a novel promising approach to address the epigenetic dysregulation of gene expression in different diseases. Inspired by the validated virtual screening hit NSC137546, a series of N-benzoyl amino acid analogues was synthesized and obtained compounds were assessed for their ability to inhibit DNMT-dependent DNA methylation in vitro. The biological screening allowed the definition of a set of preliminary structure-activity relationships and the identification of compounds promising for further development. Among the synthesized compounds, L-glutamic acid derivatives 22, 23, and 24 showed the highest ability to prevent DNA methylation in a total cell lysate. Compound 22 inhibited DNMT1 and DNMT3A activity in a concentration-dependent manner in the micromolar range. In addition, compound 22 proved to be stable in human serum and it was thus selected as a starting point for further biological studies. © 2016 John Wiley & Sons A/S.

  20. Benzoyl Peroxide Oxidation Route to the Synthesis of Solvent Soluble Polycarbazole

    PubMed Central

    Boddula, Rajender; Srinivasan, Palaniappan

    2014-01-01

    Carbazole was oxidized by benzoyl peroxide in presence of p-toluenesulfonic acid to polycarbazole salt at room temperature for the first time. Polycarbazole salts were synthesized via solution and emulsion polymerization pathways. Polycarbazole bases were prepared by dedoping from polycarbazole salts. Formation of polycarbazoles was confirmed from infrared, electronic absorption and EDAX spectra. Polycarbazole salt was obtained in amorphous nature in semiconductor range (10−5 S/cm), which was found to be soluble in less and high polar solvents. Polycarbazole salt prepared by emulsion polymerization pathway showed mixture of shapes with microrod, sphere, and pores, whereas its corresponding base showed only micropores structure. On the other hand, polycarbazole salt and its corresponding base prepared by solution polymerization pathway showed flake-like morphology. Higher thermal stability was obtained for polycarbazole salt prepared by emulsion polymerization pathway than that of the salt prepared by solution polymerization pathway. PMID:27336060

  1. Benzoyl radicals from (hetero)aromatic aldehydes. Decatungstate photocatalyzed synthesis of substituted aromatic ketones.

    PubMed

    Ravelli, Davide; Zema, Michele; Mella, Mariella; Fagnoni, Maurizio; Albini, Angelo

    2010-09-21

    Benzoyl radicals are generated directly from (hetero)aromatic aldehydes upon tetrabutylammonium decatungstate ((n-Bu(4)N)(4)W(10)O(32)), TBADT) photocatalysis under mild conditions. In the presence of alpha,beta-unsaturated esters, ketones and nitriles radical conjugate addition ensues and gives the corresponding beta-functionalized aryl alkyl ketones in moderate to good yields (stereoselectively in the case of 3-methylene-2-norbornanone). Due to the mild reaction conditions the presence of various functional groups on the aromatic ring is tolerated (e.g. methyl, methoxy, chloro). The method can be applied to hetero-aromatic aldehydes whether electron-rich (e.g. thiophene-2-carbaldehyde) or electron-poor (e.g. pyridine-3-carbaldehyde).

  2. Vitiligo and allergic complications from orthopaedic joint implants: the role of benzoyl peroxide.

    PubMed

    Dudda, Marcel; Godau, Peter; Al-Benna, Sammy; Schildhauer, Thomas A; Gothner, Martin

    2013-05-01

    Orthopaedic joint implants and osteosynthetic materials are progressively being employed more often. Complications mainly include physical-mechanical problems and infections. Uncommonly, allergic reactions to an alloy metal or a bone cement component have been implicated. Less attention has been paid to the components of bone cement, such as acrylate, catalysers (e.g. peroxide), additive polymers or stabilisers. An important bone cement component is benzoylperoxide (BPO), an initiator of the process enhancement of the bone cement. Vitiligo is an acquired, progressive depigmenting disorder that can induce autoimmune diseases. The occurrence of vitiligo in combination with an infection or allergy is not well described, and this manuscript highlights the possibility of an occurrence of a vitiligo whenever the immunesystem is activated and T-cell activation is observed. The aim of this article was to analyze the diagnosis and management of vitiligo and allergic complications from orthopaedic joint implants due to benzoyl-peroxide and relevant patents.

  3. DFT MODELING OF BENZOYL PEROXIDE ADSORPTION ON α-Cr2O3 (0001) SURFACE

    NASA Astrophysics Data System (ADS)

    Maldonado, Frank; Stashans, Arvids

    2016-04-01

    Density functional theory (DFT) within the generalized gradient approximation (GGA) has been used to investigate possible adsorption configurations of benzoyl peroxide (BPO) molecule on the chromium oxide (α-Cr2O3) (0001) surface. Two configurations are found to lead to the molecular adsorption with corresponding adsorption energies being equal to -0.16 and -0.48eV, respectively. Our work describes in detail atomic displacements for both crystalline surface and adsorbate as well as discusses electronic and magnetic properties of the system. The most favorable adsorption case is found when the chemical bond between one of the molecular oxygens and one of the surface Cr atoms has been formed.

  4. Identification of Minor Benzoylated 4-Phenylcoumarins from a Mammea neurophylla Bark Extract.

    PubMed

    Dang, Bach Tai; Rouger, Caroline; Litaudon, Marc; Richomme, Pascal; Séraphin, Denis; Derbré, Séverine

    2015-09-25

    Through dereplication analysis, seven known Mammea coumarins were identified in a fraction obtained from Mammea neurophylla dichloromethane bark extract selected for its ability to prevent advanced glycation end-product (AGE) formation. Among them, a careful examination of the NMR dataset of pedilanthocoumarin B led to a structural revision. Inspection of LC-DAD-MS(n) chromatograms allowed us to predict the presence of four new compounds, which were further isolated. Using spectroscopic methods (¹H-, (13)C- and 2D-NMR, HRMS, UV), these compounds were identified as new benzoyl substituted 4-phenylcoumarins (iso-pedilanthocoumarin B and neurophyllol C) and 4-(1-acetoxypropyl)coumarins cyclo F (ochrocarpins H and I).

  5. Synthesis of 1-O-(2'-acetoxy)benzoyl-alpha-D-2-deoxyglucopyranose, a novel aspirin prodrug.

    PubMed

    Truelove, J E; Hussain, A A; Kostenbauder, H B

    1980-02-01

    The synthesis and characterization of 1-O-(2'-acetoxy)benzoyl-alpha-D-2-deoxyglucopyranose, a novel aspirin prodrug, are described. 3,4,6-Tri-O-benzyl-alpha-D-2-deoxyglucopyranose was synthesized by methylating the anomeric hydroxyl group of 2-deoxyglucose, benzylating the 3-, 4-, and 6-hydroxy functional grups, and cleaving hydrolytically the anomeric methyl group. Reaction of the tribenzylated sugar with the acid chloride of aspirin and subsequent hydrogenolysis of the benzyl groups resulted in the prodrug, mp 128 degrees. The compound was further characterized by elemental analysis and PMR and 13C-NMR spectroscopy. In vitro, the compound cleaved to aspirin with a half-life of 7 min at 37 degrees. Prodrug cleavage was independent of pH over the pH 3--9 range.

  6. Ultrasonic degradation of N-di and trihydroxy benzoyl chitosans and its effects on antioxidant activity.

    PubMed

    Taghizadeh, Mohamad Taghi; Bahadori, Ali

    2014-05-01

    Modified chitosans with 3,4-dihydroxy benzoyl groups (CS-DHBA) and 3,4,5-trihydroxy benzoyl groups (CS-THBA) were synthesized and their chemical structures were determined by Fourier transform infrared (FT-IR) and (1)H nuclear magnetic resonance ((1)H NMR) spectroscopy. Then, ultrasonic degradation of CS, CS-DHBA and CS-THBA in 1% acetic acid solution was investigated. The kinetics studies of degradation were followed by gel permeation chromatography (GPC). The results indicated that the weight-average molecular weight of chitosan decreased obviously after ultrasound treatment, but molecular weights of CS-DHBA and CS-THBA decreased slowly with increasing sonication time. Degradation kinetics model based on 1/Mt-1/M0=kt was used to estimate the degradation rate constant. It was found that the rates of degradation of CS-DHBA and CS-THBA are lower than CS, and follow the order: CS4>CS8>CS12>CS-THBA4>CS-THBA8 ≈ CS-DHBA4>CS-THBA12>CS-DHBA8>CS-DHBA12. The antioxidant activity of the CS, CS-DHBA and CS-THBA before and after sonication was investigated by the radical scavenging activity method using 1,1-diphenyl-2-picrylhydrazyl (DPPH). The DPPH scavenging free radical capacity of CS-THBA and CS-DHBA increased up to 89% and 74% respectively, when the concentration reached 6 μg/ml. The ultrasonic treatment of CS-DHBA and CS-THBA after 30 min decreased the DPPH free radical scavenging activity but ultrasonic treatment of CS increased the DPPH free radical scavenging activity.

  7. Benzoyl peroxide and clindamycin topical skin preparation decreases Propionibacterium acnes colonization in shoulder arthroscopy.

    PubMed

    Dizay, Hailey H; Lau, Diana G; Nottage, Wesley M

    2017-07-01

    Propionibacterium acnes is a gram-positive anaerobe that can lead to devastating postoperative shoulder infections. The objective of this study was to investigate whether a benzoyl peroxide and clindamycin preoperative skin preparation reduces the incidence of P. acnes colonization during shoulder arthroscopy. Sixty-five shoulder arthroscopy patients were prospectively enrolled. A skin culture specimen was taken at the preoperative visit from standard arthroscopic portal sites. Topical benzoyl peroxide 5% and clindamycin 1.2% (BPO/C) gel was applied to the shoulder every night before surgery. Skin culture was repeated in the operating room before preparation with chlorhexidine gluconate. Shoulder arthroscopy proceeded, with final culture specimens obtained from within the shoulder. P. acnes skin colonization remained similar to prior studies at 47.7% (31 of 65 patients.) With >1 application, BPO/C was 78.9% (15 of 19 patients) effective in eliminating P. acnes superficial colonization. With 1 application, it was 66.7% (8 of 12 patients) effective in eliminating superficial colonization. Deep colonization was reduced to 3.1% (2 of 65 patients) compared with previous studies of 15% to 20% (P = .006). BPO/C was 100% effective at decreasing deep colonization with >1 application. P. acnes skin colonization is high at arthroscopic shoulder portals, especially in men. Despite standard skin preparation and prophylactic antibiotics, the rate of joint inoculation is much higher than the rate of infection reported in the literature. BPO/C effectively reduces P. acnes colonization in shoulder arthroscopy. It should be considered for use before shoulder procedures with a time-related trend of >1 application. Copyright © 2017 Journal of Shoulder and Elbow Surgery Board of Trustees. Published by Elsevier Inc. All rights reserved.

  8. In vivo neurochemical monitoring using benzoyl chloride derivatization and liquid chromatography-mass spectrometry.

    PubMed

    Song, Peng; Mabrouk, Omar S; Hershey, Neil D; Kennedy, Robert T

    2012-01-03

    In vivo neurochemical monitoring using microdialysis sampling is important in neuroscience because it allows correlation of neurotransmission with behavior, disease state, and drug concentrations in the intact brain. A significant limitation of current practice is that different assays are utilized for measuring each class of neurotransmitter. We present a high performance liquid chromatography (HPLC)-tandem mass spectrometry method that utilizes benzoyl chloride for determination of the most common low molecular weight neurotransmitters and metabolites. In this method, 17 analytes were separated in 8 min. The limit of detection was 0.03-0.2 nM for monoamine neurotransmitters, 0.05-11 nM for monoamine metabolites, 2-250 nM for amino acids, 0.5 nM for acetylcholine, 2 nM for histamine, and 25 nM for adenosine at sample volume of 5 μL. Relative standard deviation for repeated analysis at concentrations expected in vivo averaged 7% (n = 3). Commercially available (13)C benzoyl chloride was used to generate isotope-labeled internal standards for improved quantification. To demonstrate utility of the method for study of small brain regions, the GABA(A) receptor antagonist bicuculline (50 μM) was infused into a rat ventral tegmental area while recording neurotransmitter concentration locally and in nucleus accumbens, revealing complex GABAergic control over mesolimbic processes. To demonstrate high temporal resolution monitoring, samples were collected every 60 s while neostigmine, an acetylcholine esterase inhibitor, was infused into the medial prefrontal cortex. This experiment revealed selective positive control of acetylcholine over cortical glutamate.

  9. Supra­molecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N6-benzoyl­adenine salt: N 6-benzoyl­adeninium nitrate

    PubMed Central

    Karthikeyan, Ammasai; Jeeva Jasmine, Nithianantham; Thomas Muthiah, Packianathan; Perdih, Franc

    2016-01-01

    In the title molecular salt, C12H10N5O+·NO3 −, the adenine unit has an N 9-protonated N(7)—H tautomeric form with non-protonated N1 and N3 atoms. The dihedral angle between the adenine ring system and the phenyl ring is 51.10 (10)°. The typical intra­molecular N7—H⋯O hydrogen bond with an S(7) graph-set motif is also present. The benzoyl­adeninium cations also form base pairs through N—H⋯O and C—H⋯N hydrogen bonds involving the Watson–Crick face of the adenine ring and the C and O atoms of the benzoyl ring of an adjacent cation, forming a supra­molecular ribbon with R 2 2(9) rings. Benzoyl­adeninum cations are also bridged by one of the oxygen atoms of the nitrate anion, which acts as a double acceptor, forming a pair of N—H⋯O hydrogen bonds to generate a second ribbon motif. These ribbons together with π–π stacking inter­actions between the phenyl ring and the five- and six-membered adenine rings of adjacent mol­ecules generate a three-dimensional supra­molecular architecture. PMID:26958373

  10. Amperometric detection of benzoyl peroxide in pharmaceutical preparations using carbon paste electrodes with peroxidases naturally immobilized on coconut fibers.

    PubMed

    Kozan, J V B; Silva, R P; Serrano, S H P; Lima, A W O; Angnes, L

    2010-01-15

    This paper describes the applications of a new carbon paste electrode containing fibers of coconut (Cocus nucifera L.) fruit, which are very rich in peroxidase enzymes naturally immobilized on its structure. The new sensor was applied for the amperometric quantification of benzoyl peroxide in facial creams and dermatological shampoos. The amperometric measurements were performed in 0.1 mol L(-1) phosphate buffer (pH 5.2), at 0.0 V (versus Ag/AgCl). On these conditions, benzoyl peroxide was rapidly determined in the 5.0-55 micromol L(-1), with a detection limit of 2.5 micromol L(-1) (s/n=3), response time of 4.1 s (90% of the steady state) and sensitivity limit of 0.33 A mol L(-1) cm(-2). The amperometric results are in good agreement with those obtained by spectrophotometric technique, used as a standard method.

  11. catena-Poly[[diaqua-strontium(II)]-bis-[μ-2-(3-benzoyl-phen-yl)propano-ato

    PubMed

    Zhang, Zhu-Yan; Yu, Nan; Li, Min; Wu, Ning-Xin; Liu, Bing-Yi

    2010-09-04

    In the title coordination polymer, [Sr(C(16)H(13)O(3))(2)(H(2)O)(2)](n), the Sr(II) cation is eight-coordinated by six O atoms from four different 2-(3-benzoyl-phen-yl)propano-ate ligands and two O atoms of two water mol-ecules in a distorted dodeca-hedral geometry. Adjacent Sr(II) cations are bridged by two 2-(3-benzoyl-phen-yl)propano-ate ligands, forming an infinite chain along the b axis; the chains are further linked by inter-molecular O-H-O hydrogen bonds into a three-dimensional supra-molecular network.

  12. Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory

    NASA Astrophysics Data System (ADS)

    Callam, Christopher S.; Lowary, Todd L.

    2001-01-01

    We report an organic chemistry laboratory experiment in which methyl 2,3,5-tri-O-benzoyl-a-D-arabinofuranoside is synthesized. The product is obtained in two steps from commercially available D-arabinose, via Fischer glycosylation and benzoylation. The product is easily purified by crystallization. The primary purpose in implementing this experiment was to give students additional exposure to carbohydrate chemistry. In addition, the experiment provides an opportunity to discuss a number of other topics including kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity. It is also possible to incorporate 2-D NMR spectroscopy into this experiment.

    See Correction to this article.

  13. [Association between allergy to benzoyl peroxide, vitiligo and implantation of a cemented total knee joint prosthesis: Is there a connection?].

    PubMed

    Gothner, M; Ozokyay, L; Godau, P; Kälicke, T; Muhr, G; Schildhauer, T A; Dudda, M

    2011-09-01

    Allergies against bone cement or bone cement components have been well-described. We report on a 63-year-old patient who presented with progressive vitiligo all over the body after implantation of a cemented total knee replacement. A dermatological examination was performed and an allergy to benzoyl peroxide was found. A low-grade infection was diagnosed 5 months after implantation of the total knee replacement and the prosthesis was replaced with a cement spacer. After treating the infection of the knee replacement non-cemented arthrodesis of the knee was performed. In cases of new, unknown skin efflorescence, urticaria and periprosthetic loosening of cemented joint replacement, the differential diagnosis should include not only infections but also possible allergies against bone-cement and components such as benzoyl peroxide or metal components.

  14. Interaction of the O-Benzoyl-β-aminopropioamidoximes with Lawesson's Reagent and Spectral Characterization of the Products

    PubMed Central

    Kayukova, Lyudmila; Praliyev, Kaldubai; Kemelbekov, Ulan; Abdildanova, Asel; Gutyar, Vanda

    2012-01-01

    Interaction of O-benzoyl-β-aminopropioamidoximes [β-amino group: pyperidin-1-yl; morpholin-1-yl; thiomorpholin-1-yl; 4-phenylpiperazin-1-yl; benzimidazol-1-yl] with Lawesson's reagent was done in tetrahydrofuran at heating to 70°C during 10 h. New O-thiobenzoyl-β-aminopropioamidoximes were obtained with the outputs 57–96%; they were characterized with the help of physicochemical, IR, and NMR spectra. PMID:24052857

  15. Tris(N-benzoyl-N′,N′-diphenyl­thio­ureato-κ2 O,S)cobalt(III)

    PubMed Central

    Pérez, Hiram; Mascarenhas, Yvonne; Plutín, Ana María; de Souza Corrêa, Rodrigo; Duque, Julio

    2008-01-01

    In the title compound, [Co(C20H15N2OS)3], the CoIII atom is coordinated by the S and O atoms of three N-benzoyl-N′,N′-diphenyl­thio­urea ligands in a slightly distorted octa­hedral geometry. The O and S atoms are in cis positions, while the positions between the O and S atoms are trans. PMID:21201883

  16. The use of lymecycline and benzoyl peroxide for the treatment of progressive macular hypomelanosis: a prospective study.

    PubMed

    Cavalcanti, Silvana Maria de Morais; Querino, Marina Coutinho Domingues; Magalhães, Vera; França, Emmanuel Rodrigues de; Magalhães, Marcelo; Alencar, Eliane

    2011-01-01

    Progressive macular hypomelanosis is a dermatosis of uncertain etiology. The participation of Propionibacterium acnes has been suggested in view of the response achieved following therapy with drugs that are active against this bacterium. This report describes a series of thirteen patients with progressive macular hypomelanosis who were treated with an association of lymecycline and benzoyl peroxide over a three-month period. Response to treatment was excellent and the positive results were maintained during the entire follow up period.

  17. Development and in-vitro characterization of fish oil oleogels containing benzoyl peroxide and salicylic acid as keratolytic agents.

    PubMed

    Rehman, K; Tan, C M; Zulfakar, M H

    2014-03-01

    Topical keratolytic agents such as benzoyl peroxide (BP) and salicylic acid (SA) are one of the common treatments for inflammatory skin diseases. However, the amount of drug delivery through the skin is limited due to the stratum corneum. The purposes of this study were to investigate the ability of fish oil to act as penetration enhancer for topical keratolytic agents and to determine the suitable gelator for formulating stable fish oil oleogels. 2 types of gelling agents, beeswax and sorbitan monostearate (Span 60), were used to formulate oleogels. To investigate the efficacy of fish oil oleogel permeation, commercial hydrogels of benzoyl peroxide (BP) and salicylic acid (SA) were used as control, and comparative analysis was performed using Franz diffusion cell. Stability of oleogels was determined by physical assessments at 20°C and 40°C storage. Benzoyl peroxide (BP) fish oil oleogels containing beeswax were considered as better formulations in terms of drug permeation and cumulative drug release. All the results were found to be statistically significant (p<0.05, ANOVA) and it was concluded that the beeswax-fish oil combination in oleogel can prove to be beneficial in terms of permeation across the skin and stability.

  18. Orientation of N-benzoyl glycine on silver nanoparticles: SERS and DFT studies

    NASA Astrophysics Data System (ADS)

    Parameswari, A.; Asath, R. Mohamed; Premkumar, R.; Benial, A. Milton Franklin

    2017-05-01

    Surface enhanced Raman scattering (SERS) studies of N-benzoyl glycine (NBG) adsorbed on silver nanoparticles (AgNPs) was studied by experimental and density functional theory (DFT) approach. Single crystals of NBG were prepared using slow evaporation method. The AgNPs were prepared and characterized. The DFT/ B3PW91 method with LanL2DZ basis set was used to optimize the molecular structure of NBG and NBG adsorbed on silver cluster. The calculated and observed vibrational frequencies were assingned on the basis of potential energy distribution calculation. The reduced band gap value was obtained for NBG adsorbed on silver nanoparticles from the frontier molecular orbitals analysis. Natural bond orbital analysis was carried out to inspect the intra-molecular stabilization interactions, which are responsible for the bio activity and nonlinear optical property of the molecule. The spectral analysis was also evidenced that NBG would adsorb tilted orientation on the silver surface over the binding sites such as lone pair electron of N atom in amine group and through phenyl ring π system.

  19. [Detection of benzoyl peroxide in wheat flour by NIR diffuse reflectance spectroscopy technique].

    PubMed

    Zhang, Zhi-yong; Li, Gang; Liu, Hai-xue; Lin, Ling; Zhang, Bao-ju; Wu, Xiao-rong

    2011-12-01

    Adding benzoyl peroxide (BPO) into wheat flour was prohibited by the relevant government departments since May 1, 2011. And it is of great importance to detect BPO additive amount in wheat flour quickly and accurately. Part of BPO which was added into wheat flour will be deoxidized into benzoic acid, and this make it complex to detect the original BPO additive amount. The objective of the present research is to investigate the potential of NIR diffuse reflectance spectroscopy as a way for measurement of BPO original adding amount in wheat flour. A total of 133 wheat flour samples were prepared by adding different content of BPO into pure wheat flour. Spectra data were obtained by NIR spectrometer and then denoised by wavelet transform. Ninety seven samples were taken as calibration set and other 36 samples as prediction set. Partial least squares regression (PLSR) was applied to establish the calibration model between BPO original adding contents and the spectra data. The determination coefficient of model for the calibration set is 0.8901, and root mean squared error of calibration (RMSEC) is 40.85 mg x kg(-1). The determination coefficient for the prediction set is 0.8865, and root mean squared error of prediction (RMSEP) is 44.69 mg x kg(-1). The result indicates that it is feasible to detect the BPO adding contents in wheat flour by NIR diffuse reflectance spectroscopy technique and this technique has the potential to measure some other additives in food.

  20. Design, synthesis, and anti-melanogenic effects of (E)-2-benzoyl-3-(substituted phenyl)acrylonitriles

    PubMed Central

    Yun, Hwi Young; Kim, Do Hyun; Son, Sujin; Ullah, Sultan; Kim, Seong Jin; Kim, Yeon-Jeong; Yoo, Jin-Wook; Jung, Yunjin; Chun, Pusoon; Moon, Hyung Ryong

    2015-01-01

    Background Tyrosinase is the most prominent target for inhibitors of hyperpigmentation because it plays a critical role in melaninogenesis. Although many tyrosinase inhibitors have been identified, from both natural and synthetic sources, there remains a considerable demand for novel tyrosinase inhibitors that are safer and more effective. Methods (E)-2-Benzoyl-3-(substituted phenyl)acrylonitriles (BPA analogs) with a linear β-phenyl-α,β-unsaturated carbonyl scaffold were designed and synthesized as potential tyrosinase inhibitors. We evaluated their effects on cellular tyrosinase activity and melanin biosynthesis in murine B16F10 melanoma cells and their ability to inhibit mushroom tyrosinase activity. Results BPA analogs exhibited inhibitory activity against mushroom tyrosinase. In particular, BPA13 significantly suppressed melanin biosynthesis and inhibited cellular tyrosinase activity in B16F10 cells in a dose-dependent manner. A docking study revealed that BPA13 had higher binding affinity for tyrosinase than kojic acid. Conclusion BPA13, which possesses a linear β-phenyl-α,β-unsaturated carbonyl scaffold, is a potential candidate skin-whitening agent and treatment for diseases associated with hyperpigmentation. PMID:26347064

  1. Benzoyl Peroxide as an Efficient Dopant for Spiro-OMeTAD in Perovskite Solar Cells.

    PubMed

    Liu, Qiuju; Fan, Lisheng; Zhang, Qin'e; Zhou, An'an; Wang, Baozeng; Bai, Hua; Tian, Qingyong; Fan, Bin; Zhang, Tongyi

    2017-08-10

    Although organic small molecule spiro-OMeTAD is widely used as a hole-transport material in perovskite solar cells, its limited electric conductivity poses a bottleneck in the efficiency improvement of perovskite solar cells. Here, a low-cost and easy-fabrication technique is developed to enhance the conductivity and hole-extraction ability of spiro-OMeTAD by doping it with commercially available benzoyl peroxide (BPO). The experimental results show that the conductivity increases several orders of magnitude, from 6.2×10(-6)  S cm(-1) for the pristine spiro-OMeTAD to 1.1×10(-3)  S cm(-1) at 5 % BPO doping and to 2.4×10(-2)  S cm(-1) at 15 % BPO doping, which considerably outperform the conductivity of 4.62×10(-4)  S cm(-1) for the currently used oxygen-doped spiro-OMeTAD. The fluorescence spectra suggest that the BPO-doped spiro-OMeTAD-OMeTAD layer is able to efficiently extract holes from CH3 NH3 PbI3 and thus greatly enhances the charge transfer. The BPO-doped spiro-OMeTAD is used in the fabrication of perovskite solar cells, which exhibit enhancement in the power conversion efficiency. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  2. CXCR4 antagonist 4F-benzoyl-TN14003 inhibits leukemia and multiple myeloma tumor growth.

    PubMed

    Beider, Katia; Begin, Michal; Abraham, Michal; Wald, Hanna; Weiss, Ido D; Wald, Ori; Pikarsky, Eli; Zeira, Evelyne; Eizenberg, Orly; Galun, Eithan; Hardan, Izhar; Engelhard, Dan; Nagler, Arnon; Peled, Amnon

    2011-03-01

    The chemokine receptor CXCR4 and its ligand CXCL12 are involved in the progression and dissemination of a diverse number of solid and hematological malignancies. Binding CXCL12 to CXCR4 activates a variety of intracellular signal transduction pathways that regulate cell chemotaxis, adhesion, survival, proliferation, and apoptosis. Here, we demonstrate that the CXCR4 antagonist, 4F-benzoyl-TN14003 (BKT140), but not AMD3100, exhibits a CXCR4-dependent preferential cytotoxicity toward malignant cells of hematopoietic origin. BKT140 significantly and preferentially stimulated multiple myeloma apoptotic cell death. BKT140 treatment induced morphological changes, phosphatidylserine externalization, decreased mitochondrial membrane potential, caspase-3 activation, sub-G1 arrest, and DNA double-stranded breaks. In vivo, subcutaneous injections of BKT140 significantly reduced, in a dose-dependent manner, the growth of human acute myeloid leukemia and multiple myeloma xenografts. Tumors from animals treated with BKT140 were smaller in size and weights, had larger necrotic areas and high apoptotic scores. Taken together, these results suggest a potential therapeutic use for BKT140 in multiple myeloma and leukemia patients. Copyright © 2011 ISEH - Society for Hematology and Stem Cells. Published by Elsevier Inc. All rights reserved.

  3. Crystal structure of N-(2-benzoyl-5-ethynylphen-yl)quinoline-2-carboxamide.

    PubMed

    Peña-Solórzano, Diana; König, Burkhard; Sierra, Cesar A; Ochoa-Puentes, Cristian

    2017-04-01

    In the title compound, C25H16N2O2, the quinoline ring system is essentially planar, with a maximum deviation of 0.030 (1) Å, and forms a dihedral angle of 20.9 (1)° with benzoyl benzene ring. The unsubstituted phenyl ring forms dihedral angles of 52.7 (1)° with the quinoline ring system and 54.1 (1)° with the ethynyl-substituted benzene ring. The mol-ecule contains an intra-molecular bifurcated N-H⋯(O,N) hydrogen bond, forming S(5) and S(6) rings, which may influence the conformation of the mol-ecule. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. In addition, the three-dimensional structure contains π-π stacking inter-actions, with centroid-centroid distances of 3.695 (1) and 3.751 (1) Å.

  4. Ex vivo demonstration of a synergistic effect of Adapalene and benzoyl peroxide on inflammatory acne lesions.

    PubMed

    Zuliani, Thomas; Khammari, Amir; Chaussy, Hélène; Knol, Anne Chantal; Dréno, Brigitte

    2011-10-01

    Acne is a chronic inflammatory disease of the pilosebaceous follicle. Thanks to its ability to reduce both comedones and inflammatory lesions, the association of a retinoid and benzoyl peroxide (BPO) is now recommended for the treatment of acne. However, the mechanisms of action of this combined therapy on inflammatory acne lesions are not well understood. In an ex vivo immunohistochemistry study, we investigated the potential synergistic modulator effect of Adapalene associated with BPO on keratinocytes proliferation/differentiation and innate immunity in inflammatory acne lesions. We demonstrated that proliferation (Ki-67), adhesion/differentiation (integrin α(2), α(3) and α(6)) and innate immunity (TLR-2, β-defensin 4, IL-8) markers are overexpressed in inflammatory acne skin compared with uninvolved acne skin. Association of Adapalene and BPO significantly decreased expression of Ki67, α(2) and α(6) integrins, TLR-2, β-defensin 4 and IL-8 in inflammatory acne skin, whereas single treatments with Adapalene or BPO alone were less effective. These results contribute to explain the comedolytic and anti-inflammatory activities of this combined therapy observed in recent clinical trials. © 2011 John Wiley & Sons A/S.

  5. Detecting benzoyl peroxide in wheat flour by line-scan macro-scale Raman chemical imaging

    NASA Astrophysics Data System (ADS)

    Qin, Jianwei; Kim, Moon S.; Chao, Kuanglin; Gonzalez, Maria; Cho, Byoung-Kwan

    2017-05-01

    Excessive use of benzoyl peroxide (BPO, a bleaching agent) in wheat flour can destroy flour nutrients and cause diseases to consumers. A macro-scale Raman chemical imaging method was developed for direct detection of BPO mixed in the wheat flour. A 785 nm line laser was used in a line-scan Hyperspectral Raman imaging system. Raman images were collected from wheat flour mixed with BPO at eight concentrations (w/w) from 50 to 6,400 ppm. A sample holder (150×100×2 mm3) was used to present a thin layer (2 mm thick) of the powdered sample for image acquisition. A baseline correction method was used to correct the fluctuating fluorescence signals from the wheat flour. To isolate BPO particles from the flour background, a simple thresholding method was applied to the single-band fluorescence-free images at a unique Raman peak wavenumber (i.e., 1001 cm-1) preselected for the BPO detection. Chemical images were created to detect and map the BPO particles. Limit of detection for the BPO was estimated in the order of 50 ppm, which is on the same level with regulatory standards.

  6. Deciphering the intercalative binding modes of benzoyl peroxide with calf thymus DNA.

    PubMed

    Xia, Kaixin; Zhang, Guowen; Gong, Deming

    2017-01-24

    The binding of benzoyl peroxide (BPO), a flour brightener, with calf thymus DNA (ctDNA) was predicted by molecular simulation, and this were confirmed using multi-spectroscopic techniques and a chemometrics algorithm. The molecular docking result showed that BPO could insert into the base pairs of ctDNA, and the adenine bases were the preferential binding sites which were validated by the analysis of Fourier transform infrared spectra. The mode of binding of BPO with ctDNA was an intercalation as supported by the results from ctDNA melting and viscosity measurements, iodide quenching effects and competitive binding investigations. The circular dichroism and DNA cleavage assays indicated that BPO induced a conformational change from B-like DNA structure towards to A-like form, but did not lead to significant damage in the DNA. The complexation was driven mainly by hydrogen bonds and hydrophobic interactions. Moreover, the ultraviolet-visible (UV-vis) spectroscopic data matrix was resolved by a multivariate curve resolution-alternating least-squares algorithm. The equilibrium concentration profiles for the components (BPO, ctDNA and BPO-ctDNA complex) were extracted from the highly overlapping composite response to quantitatively monitor the BPO-ctDNA interaction. This study has provided insights into the mechanism of the interaction of BPO with ctDNA and potential hazards of the food additive.

  7. Polymeric micellar nanocarriers of benzoyl peroxide as potential follicular targeting approach for acne treatment.

    PubMed

    Kahraman, Emine; Özhan, Gül; Özsoy, Yıldız; Güngör, Sevgi

    2016-10-01

    The aim of this work was to optimize polymeric nano-sized micellar carriers of the anti-acne compound benzoyl peroxide (BPO) and to examine the ability of these carriers to deposit into hair follicles with the objective of improving skin delivery of BPO. BPO loaded polymeric micelles composed of Pluronic(®) F127 were prepared by the thin film hydration method and characterized in terms of size, loading capacity, morphology and physical stability. The optimized micelle formulation was then selected for skin delivery studies. The penetration of BPO loaded micellar carriers into skin and skin appendages across full thickness porcine skin was examined in vitro. Confocal microscopy images confirmed the penetration of Nile Red into hair follicles, which was loaded into micellar carriers as a model fluorescent compound. The relative safety of the polymeric micelles was evaluated with the MTT viability test using mouse embryonic fibroblasts. The results indicated that nano-sized polymeric micelles of BPO composed of Pluronic(®) F127 offer a potential approach to enhance skin delivery of BPO and that targeting of micelles into hair follicles may be an effective and safe acne treatment.

  8. N-benzoyl-n-phenylhydroxylamine impregnated Amberlite XAD-4 beads for selective removal of thorium.

    PubMed

    Chandramouleeswaran, S; Ramkumar, Jayshree

    2014-09-15

    n-Benzoyl-n-phenylhydroxylamine impregnated Amberlite XAD-4 beads were used for the removal of Th(IV) from a mixture of ions. The impregnated XAD was characterized using different techniques like weight and colour change, IR spectra, surface area and pore size measurements to confirm the presence of n-BPHA within the macroreticular resin structure. The experimental conditions were optimized to make the separation fast and selective. It was seen that the maximum sorption was achieved in the pH range of 3-7.5 and uptake was nearly complete within half an hour. The results obtained in the present study were subjected to extensive modelling in order to get a complete understanding of the sorption process. It is seen that the maximum uptake was calculated to be 500 mg/g and has very fast kinetics it was seen that the process is chemisorption. It was further deduced from the modelling that the overall sorption process was controlled dominantly by external mass transfer. Considering the simplicity this procedure, the present study has a possible application for the removal of thorium from different mixtures.

  9. Case-based experience with the simultaneous use of a fixed topical antibiotic/benzoyl peroxide combination and a topical retinoid in the optimization of acne management.

    PubMed

    Ditre, Chérie M

    2009-12-01

    Treatment options for acne vulgaris have expanded considerably in the past decade. The main goals of treatment continue to be reducing acne lesions while maintaining patient satisfaction and adherence to treatment. As dermatologists, the art of treatment is to develop, fine-tune, and utilize combinations of agents to increase compliance, thereby optimizing patient outcomes. In acne management, one strategy involves concomitant use of topical retinoids with benzoyl peroxide or a fixed combination of topical antibiotic/benzoyl peroxide. This strategy requires application of one product in the morning and one in the evening due to concerns of benzoyl peroxide-induced degradation of retinoid activity. Presented are two cases in which a topical retinoid and a topical fixed combination of clindamycin/benzoyl peroxide were used concomitantly in patients with mild-to-moderate acne. Research-based and practical rationale on the simultaneous use of newer-generation retinoids and benzoyl peroxide-based products, without concern of retinoid degradation, is discussed.

  10. Efficacy of the addition of salicylic acid to clindamycin and benzoyl peroxide combination for acne vulgaris.

    PubMed

    Akarsu, Sevgi; Fetil, Emel; Yücel, Filiz; Gül, Eylem; Güneş, Ali T

    2012-05-01

    Clindamycin phosphate (CDP), benzoyl peroxide (BPO) and salicylic acid (SA) are known to be effective acne therapy agents depending on their anti-inflammatory and comedolytic properties. The purpose of this study was to investigate the efficacy and tolerability of the addition of SA treatment to CDP and BPO (SA and CDP + BPO) and compare it with CDP + BPO in patients with mild to moderate facial acne vulgaris. Forty-nine patients were enrolled in a 12 week prospective, single-blind, randomized, comparative clinical study. Efficacy was assessed by lesion counts, global improvement, quality of life index and measurements of skin barrier functions. Local side effects were also evaluated. Both combinations were effective in reducing total lesion (TL), inflammatory lesion (IL) and non-inflammatory lesion (NIL) counts. There were statistically significant differences between treatment groups for reductions in NIL counts beyond 2 weeks, IL counts and TL counts throughout the all study weeks, and global improvement scores evaluated by patients and investigator at the end of the study in favor of SA and CDP + BPO treatment when compared to CDP + BPO treatment. Both combinations significantly decreased stratum corneum hydration, although skin sebum values decreased with SA and CDP + BPO treatment. These combinations were also well tolerated except significantly higher frequency of mild to moderate transient dryness in patients applied SA and CDP + BPO. The addition of SA to CDP + BPO treatment demonstrated significantly better and faster results in terms of reductions in acne lesion counts and well tolerated except for higher frequency of mild to moderate transient dryness. © 2011 Japanese Dermatological Association.

  11. Photochemically-induced fluorescence properties of two benzoyl- and phenylurea pesticides and determination in natural waters.

    PubMed

    Diaw, P A; Mbaye, O M A; Gaye-Seye, M D; Aaron, J-J; Coly, A; Tine, A; Oturan, N; Oturan, M A

    2014-07-01

    A photo-induced fluorescence (PIF) method was developed for the determination of two benzoyl- and phenylurea pesticides, namely diflubenzuron (DFB) and fenuron (FEN). The photoconversion under UV irradiation of both pesticides into strongly fluorescent photoproducts was performed in several media (methanol, ethanol, acetonitrile, pH4 aqueous solution and pH4 water-methanol (30:70, v/v) mixture). PIF parameters were optimized. Analytical figures of merit for the PIF determination of DFB and FEN were satisfactory, with rather wide linear dynamic range (LDR) values of one to two orders of magnitude, relatively low limit of detection (LOD) values of, respectively, 9-24 ng/mL for DFB and 1-28 ng/mL for FEN, and limit of quantification (LOQ) values of, respectively, 30-80 ng/mL for DFB and 4-95 ng/mL for FEN, according to the medium. Relative standard deviation (RSD) values were in the range 1.7-5.6%. PIF was validated by comparing its analytical performances to those of a standard UV absorption spectrophotometric method. The optimized PIF method was applied to the quantitative analysis of both pesticides in various spiked natural water samples collected in a Senegal agricultural area by the standard addition procedure prior to extraction steps in dichloromethane, with satisfactory mean recovery percentage values (97.0-105.3 for DFB and 98.3-102.8% for FEN). An interference study of foreign species, including pesticides and inorganic ions, likely to be present in natural waters, was also carried out.

  12. A North American study of adapalene-benzoyl peroxide combination gel in the treatment of acne.

    PubMed

    Gold, Linda Stein; Tan, Jerry; Cruz-Santana, Alma; Papp, Kim; Poulin, Yves; Schlessinger, Joel; Gidner, Judi; Liu, Yin; Graeber, Michael

    2009-08-01

    A fixed-dose combination gel with adapalene 0.1% and benzoyl peroxide (BPO) 2.5% recently has been developed for the treatment of acne vulgaris. In this multicenter, randomized, double-blind, parallel-group, active- and vehicle-controlled study conducted at 60 centers in the United States, Puerto Rico, and Canada, we assessed the efficacy and safety of adapalene-BPO combination gel in comparison with adapalene and BPO monotherapies as well as the gel vehicle. Participants with moderate facial acne vulgaris (rated 3 on the 5-point investigator global assessment of acne severity scale) were recruited and randomized to receive once-daily treatment with adapalene-BPO combination gel, adapalene monotherapy, BPO monotherapy, or gel vehicle for 12 weeks. They were assessed for success rate (the percentage of participants with investigator global assessment of acne severity rated clear or almost clear) and percentage change in inflammatory lesion (IL), noninflammatory lesion (NIL), and total lesion counts. Of the 1668 participants enrolled, 1429 (85.7%) completed the study. At study end point, adapalene-BPO combination gel showed a significantly higher success rate (P < or = .006) and a greater percentage reduction in all acne lesion counts (P < or = .017) compared with the other treatment groups. A significant early treatment effect of adapalene-BPO combination gel at week 1 compared with adapalene monotherapy and vehicle also was observed for all lesion count reductions (P<.001). The safety of adapalene-BPO combination gel was comparable with adapalene and BPO monotherapies and vehicle. In a large clinical trial, the adapalene-BPO fixed-dose combination gel has shown superiority in efficacy compared with adapalene and BPO monotherapies and vehicle, with an early onset of efficacy and a good safety profile.

  13. The efficacy of adapalene-benzoyl peroxide combination increases with number of acne lesions.

    PubMed

    Feldman, Steven R; Tan, Jerry; Poulin, Yves; Dirschka, Thomas; Kerrouche, Nabil; Manna, Vasant

    2011-06-01

    There is no direct correlation between acne severity and lesion numbers and patients with moderate acne may present with varying lesion counts. The fixed-dose adapalene 0.1%-benzoyl peroxide (BPO) 2.5% combination gel is an efficacious and safe acne treatment. We sought to evaluate whether the benefit of adapalene-BPO relative to vehicle varies with baseline lesion counts. Data were pooled from 3 randomized, double-blind, controlled studies, which compared efficacy in 4 treatment groups (adapalene-BPO, adapalene, BPO, and the gel vehicle). Three lesion count subgroups (Low, Mid, and High) were defined based on the number of total, inflammatory, or noninflammatory lesion at baseline. Efficacy of each treatment and benefit of each treatment relative to vehicle were evaluated on the entire population and in all lesion count subgroups. Safety was assessed by local tolerability score and adverse events. Adapalene-BPO provided significant benefit relative to vehicle and monotherapies on the entire population and in all lesion count subgroups (P < .05). At study end point, the benefit of adapalene-BPO relative to vehicle was greatest in the High subgroup, suggesting that patients with the highest baseline lesion counts contributed the most to the treatment benefit observed in the entire population. This effect was only observed with adapalene-BPO and not with monotherapies. Higher baseline lesion counts did not lead to more related adverse event or worse tolerability score for adapalene-BPO. These results were generated from clinical trials. Results in clinical practice could differ. The relative benefit of adapalene-BPO increases with higher lesion counts at baseline. Copyright © 2010 American Academy of Dermatology, Inc. Published by Mosby, Inc. All rights reserved.

  14. A New, Once-daily, Optimized, Fixed Combination of Clindamycin Phosphate 1.2% and Low-concentration Benzoyl Peroxide 2.5% Gel for the Treatment of Moderate-to-Severe Acne.

    PubMed

    Gold, Michael H

    2009-05-01

    The treatment of acne with combination therapy is commonplace with treatment aimed at sustained efficacy with minimal side effects, maximum adherence, and the avoidance of bacterial resistance. Combinations containing clindamycin and benzoyl peroxide have been shown to be effective, but the irritation caused by the concentration of benzoyl peroxide 5% in the more commonly used, fixed combinations can be limiting. In addition, surfactants, preservatives, and high levels of organic solvents, including alcohols, often used in combination with benzoyl peroxide, are potential irritants. An optimized formulation of clindamycin and benzoyl peroxide using a lower concentration of benzoyl peroxide (clindamycin-benzoyl peroxide 2.5% gel) has been developed without the use of surfactants or alcohol. It was recently introduced for the once-daily treatment of inflammatory and noninflammatory lesions in moderate-to-severe acne. Following a clinical program that studied more than 2,800 patients, clindamycin-benzoyl peroxide 2.5% was found to be highly effective and well tolerated. This review highlights the development of clindamycin-benzoyl peroxide 2.5% gel and the data from clinical trials.(J Clin Aesthetic Dermatol. 2009;2(5):44-48.).

  15. Chloroxylenol and zinc oxide containing cream (Nels cream) vs. 5% benzoyl peroxide cream in the treatment of acne vulgaris. A double-blind, randomized, controlled trial.

    PubMed

    Papageorgiou, P P; Chu, A C

    2000-01-01

    Forty-one subjects completed a double-blind controlled randomized study comparing the following: (i) Nels cream (containing chloroxylenol and zinc oxide); (ii) 5% benzoyl peroxide cream; and (iii) the vehicle of the Nels cream. Patients applied the medications twice daily for 8 weeks. At the end of the test period there was no significant difference in the reduction of inflammatory and noninflammatory lesion counts achieved by Nels cream and benzoyl peroxide. Both creams proved superior to the vehicle. Efficacy grading by subjects and investigators showed no significant difference between Nels cream and benzoyl peroxide. However, side-effects such as peeling and dryness caused by the treatment were significantly less in the Nels cream group.

  16. Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,4-anhydro-D-xylitol.

    PubMed

    Wang, N; Gray, G R

    1995-09-08

    Described herein is a general method for the synthesis of all positional isomers of methylated and acetylated or benzoylated 1,4-anhydro-D-xylitol. The benzoates are generated simultaneously from 1,4-anhydro-D-xylitol by sequential partial methylation and benzoylation or sequential partial benzoylation and methylation. The individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation provided the corresponding acetates. The 1H NMR spectra of the benzoates and the electron ionization mass spectra of the acetates and the tri-O-methyl derivative are reported herein as are the linear temperature programmed gas-liquid chromatography retention indices of the acetates and the tri-O-methyl derivative on three different capillary columns.

  17. Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives.

    PubMed

    Leong, Sze Wei; Mohd Faudzi, Siti Munirah; Abas, Faridah; Mohd Aluwi, Mohd Fadhlizil Fasihi; Rullah, Kamal; Lam, Kok Wai; Abdul Bahari, Mohd Nazri; Ahmad, Syahida; Tham, Chau Ling; Shaari, Khozirah; Lajis, Nordin H

    2015-08-15

    A series of twenty-four 2-benzoyl-6-benzylidenecyclohexanone analogs were synthesized and evaluated for their nitric oxide inhibition and antioxidant activity. Six compounds (3, 8, 10, 17, 18 and 19) were found to exhibit significant NO inhibitory activity in LPS/IFN-induced RAW 264.7 macrophages, of which compound 10 demonstrated the highest activity with the IC50 value of 4.2 ± 0.2 μM. Furthermore, two compounds (10 and 17) displayed antioxidant activity upon both the DPPH scavenging and FRAP analyses. However, none of the 2-benzoyl-6-benzylidenecyclohexanone analogs significantly scavenged NO radical. Structure-activity comparison suggested that 3,4-dihydroxylphenyl ring is crucial for bioactivities of the 2-benzoyl-6-benzylidenecyclohexanone analogs. The results from this study and the reports from previous studies indicated that compound 10 could be a candidate for further investigation on its potential as a new anti-inflammatory agent.

  18. An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation.

    PubMed

    Doan, Tan L H; Dao, Thong Q; Tran, Hai N; Tran, Phuong H; Le, Thach N

    2016-05-04

    A zirconium-based metal-organic framework, an effective heterogeneous catalyst, has been developed for the Friedel-Crafts benzoylation of aromatic compounds under microwave irradiation. Constructed by a Zr(iv) cluster and a linker 1,4-bis(2-[4-carboxyphenyl]ethynyl)benzene (H2CPEB), the MOF, possessing large pores and high chemical stability, was appropriate for the enhancement of Lewis acid activity under microwave irradiation. The reaction studies demonstrated that the material could give high yields for a few minutes and maintain its reactivity and structure over several cycles.

  19. (8-Benzoyl-2,7-dieth­oxy­naphthalen-1-yl)(phen­yl)methanone

    PubMed Central

    Isogai, Atsumi; Tsumuki, Takehiro; Murohashi, Shun; Okamoto, Akiko; Yonezawa, Noriyuki

    2013-01-01

    In the title compound, C28H24O4, the benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti­parallel, and the benzene rings make a dihedral angle of 20.03 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 68.42 (5) and 71.69 (5)°. In the crystal, adjacent mol­ecules are linked via C—H⋯O hydrogen bonds, forming chains propagating along [100]. PMID:23476452

  20. Palladium(II)-catalyzed ortho-C-H arylation/alkylation of N-benzoyl α-amino ester derivatives.

    PubMed

    Misal Castro, Luis C; Chatani, Naoto

    2014-04-14

    The palladium-catalyzed arylation/alkylation of ortho-C-H bonds in N-benzoyl α-amino ester derivatives is described. In such a system both the NH-amido and the CO2R groups in the α-amino ester moieties play a role in successful C-H activation/C-C bond formation using iodoaryl coupling partners. A wide variety of functional groups and electron-rich/deficient iodoarenes are tolerated. The yields obtained range from 20 to 95%.

  1. 1-(1,3-Benzothia­zol-2-yl)-3-benzoyl­thio­urea

    PubMed Central

    Yunus, Uzma; Tahir, Muhammad Kalim; Bhatti, Moazzam Hussain; Ali, Saqib; Wong, Wai-Yeung

    2008-01-01

    The title compound, C15H11N3OS2, was synthesized from benzoyl thio­cyanate and 2-amino­benzothia­zole in dry acetone. The thio­urea group is in the thio­amide form. The mol­ecules are stabilized by two inter­molecular C—H⋯S and C—H⋯O hydrogen bonds. Intra­molecular N—H⋯O hydrogen bonding results in a pseudo-S(6) planar ring with dihedral angles of 11.23 and 11.91° with the benzothiazole ring system and the phenyl ring, respectively. PMID:21200765

  2. Evaluating clinical trial design: systematic review of randomized vehicle-controlled trials for determining efficacy of benzoyl peroxide topical therapy for acne.

    PubMed

    Lamel, Sonia A; Sivamani, Raja K; Rahvar, Maral; Maibach, Howard I

    2015-11-01

    Determined efficacies of benzoyl peroxide may be affected by study design, implementation, and vehicle effects. We sought to elucidate areas that may allow improvement in determining accurate treatment efficacies by determining rates of active treatment and vehicle responders in randomized controlled trials assessing the efficacy of topical benzoyl peroxide to treat acne. We conducted a systematic review of randomized vehicle-controlled trials evaluating the efficacy of topical benzoyl peroxide for the treatment of acne. We compared response rates of vehicle treatment arms versus those in benzoyl peroxide arms. Twelve trials met inclusion criteria with 2818 patients receiving benzoyl peroxide monotherapy treatment and 2004 receiving vehicle treatment. The average percent reduction in total number of acne lesions was 44.3 (SD = 9.2) and 27.8 (SD = 21.0) for the active and vehicle treatment groups, respectively. The average reduction in non-inflammatory lesions was 41.5 % (SD = 9.4) in the active treatment group and 27.0 % (SD = 20.9) in the vehicle group. The average percent decrease in inflammatory lesions was 52.1 (SD = 10.4) in the benzoyl peroxide group and 34.7 (SD = 22.7) in the vehicle group. The average percentage of participants achieving success per designated study outcomes was 28.6 (SD = 17.3) and 15.2 (SD = 9.5) in the active treatment and vehicle groups, respectively. Patient responses in randomized controlled trials evaluating topical acne therapies may be affected by clinical trial design, implementation, the biologic effects of vehicles, and natural disease progression. "No treatment" groups may facilitate determination of accurate treatment efficacies.

  3. Adapalene-benzoyl Peroxide Gel is Efficacious and Safe in Adult Female Acne, with a Profile Comparable to that Seen in Teen-aged Females

    PubMed Central

    Baldwin, Hilary; Rueda, Maria Jose; Kerrouche, Nabil; DrÉno, Brigitte

    2016-01-01

    Objectives: To evaluate the efficacy and safety of adapalene 0.1% benzoyl peroxide 2.5% gel in women aged 25 years or older via subgroup analysis of existing Phase 2 and 3 study data. Methods: Meta-analysis of pooled data from three multicenter, randomized, double-blind, vehicle-controlled, parallel-group, clinical trials compared results of treatment with either adapalene 0.1% benzoyl peroxide 2.5% gel or vehicle gel in adult females and teen-aged females. Efficacy assessments included investigator’s global assessment and median percent change in acne lesions. Safety assessments included skin tolerability and adverse events. Results: Two hundred fifty-four adult females and 488 teen-aged females were included in the analyses, and baseline characteristics were comparable between subjects receiving adapalene 0.1% benzoyl peroxide 2.5% or vehicle. Both adult females and teen-aged females in the adapalene 0.1% benzoyl peroxide 2.5% arm were significantly more often rated clear/almost clear compared with those in the vehicle arm at Weeks 8 (P=0.016) and 12 (P<0.001); at endpoint, success was achieved in 39.2 percent with adapalene 0.1% benzoyl peroxide 2.5% and 18.5 percent with vehicle. Comparison of the amount of difference between active and vehicle reductions in investigator’s global assessment showed that efficacy was similar for adult females versus teen-aged females (20.7% vs. 19.9%, respectively). Adapalene 0.1% benzoyl peroxide 2.5% had a rapid onset of action, with statistically significant reductions in all acne lesion types versus vehicle observed by Week 1. Adapalene 0.1% benzoyl peroxide 2.5% was safe and well-tolerated by adult females with a tolerability profile consistent with that seen in teen-aged females. Conclusions: The once-daily fixed-dose combination product adapalene 0.1% benzoyl peroxide 2.5% is an efficacious, safe, and well-tolerated treatment for adult female acne, with a profile similar to that in teen-aged females. PMID:28331557

  4. Stereochemistry of N-Benzoyl-5-substituted-1-benzazepines Revisited: Synthesis of the Conformationally Biased Derivatives and Revision of the Reported Structure.

    PubMed

    Tabata, Hidetsugu; Yoneda, Tetsuya; Tasaka, Tomohiko; Ito, Shigekazu; Oshitari, Tetsuta; Takahashi, Hideyo; Natsugari, Hideaki

    2016-04-15

    The syn (aR*,5R*) and anti (aS*,5R*) diastereomers of N-benzoyl-C5-substituted-1-benzazepines originating in the chiralities at C5 and the Ar-N(C═O) axis were first stereoselectively synthesized by biasing the conformation with a substituent at C6 and C9, respectively. Detailed examination of the stereochemistry (i.e., conformation and configuration) of these N-benzoyl-1-benzazepines by X-ray crystallographic analysis, VT NMR, and DFT calculations revealed new physicochemical aspects of these heterocycles including revision of the stereochemistry previously reported.

  5. Synthesis of the kyotorphin precursor benzoyl-L-tyrosine-L-argininamide with immobilized α-chymotrypsin in sequential batch with enzyme reactivation.

    PubMed

    Bahamondes, Carola; Wilson, Lorena; Bernal, Claudia; Illanes, Andrés; Álvaro, Gregorio; Guzmán, Fanny

    2016-01-01

    α-Chymotrypsin was immobilized in activated agarose support and the stability of the biocatalyst was assessed in three polar organic solvents, namely, ethanol, diglyme, and acetonitrile. Ethanol was the solvent in which the stability of the enzyme was higher and was then selected to perform the synthesis of the kyotorphin derivative benzoyl-tyrosine argininamide, evaluating enzyme reactivation after synthesis. Substrates for reaction were benzoyl tyrosine ethyl ester and argininamide, the reaction being performed under kinetic control. High conversion yield (85%) was obtained and the immobilized enzyme was successfully used in sequential batch reactor operation with enzyme reactivation after three batches. © 2015 American Institute of Chemical Engineers.

  6. Adapalene-benzoyl Peroxide Gel is Efficacious and Safe in Adult Female Acne, with a Profile Comparable to that Seen in Teen-aged Females.

    PubMed

    Gold, Linda Stein; Baldwin, Hilary; Rueda, Maria Jose; Kerrouche, Nabil; DrÉno, Brigitte

    2016-07-01

    Objectives: To evaluate the efficacy and safety of adapalene 0.1% benzoyl peroxide 2.5% gel in women aged 25 years or older via subgroup analysis of existing Phase 2 and 3 study data. Methods: Meta-analysis of pooled data from three multicenter, randomized, double-blind, vehicle-controlled, parallel-group, clinical trials compared results of treatment with either adapalene 0.1% benzoyl peroxide 2.5% gel or vehicle gel in adult females and teen-aged females. Efficacy assessments included investigator's global assessment and median percent change in acne lesions. Safety assessments included skin tolerability and adverse events. Results: Two hundred fifty-four adult females and 488 teen-aged females were included in the analyses, and baseline characteristics were comparable between subjects receiving adapalene 0.1% benzoyl peroxide 2.5% or vehicle. Both adult females and teen-aged females in the adapalene 0.1% benzoyl peroxide 2.5% arm were significantly more often rated clear/almost clear compared with those in the vehicle arm at Weeks 8 (P=0.016) and 12 (P<0.001); at endpoint, success was achieved in 39.2 percent with adapalene 0.1% benzoyl peroxide 2.5% and 18.5 percent with vehicle. Comparison of the amount of difference between active and vehicle reductions in investigator's global assessment showed that efficacy was similar for adult females versus teen-aged females (20.7% vs. 19.9%, respectively). Adapalene 0.1% benzoyl peroxide 2.5% had a rapid onset of action, with statistically significant reductions in all acne lesion types versus vehicle observed by Week 1. Adapalene 0.1% benzoyl peroxide 2.5% was safe and well-tolerated by adult females with a tolerability profile consistent with that seen in teen-aged females. Conclusions: The once-daily fixed-dose combination product adapalene 0.1% benzoyl peroxide 2.5% is an efficacious, safe, and well-tolerated treatment for adult female acne, with a profile similar to that in teen-aged females.

  7. Substitution Effects and Linear Free Energy Relationships During Reduction of 4- Benzoyl-n-(4-substituted Benzyl)pyridinium Cations

    NASA Technical Reports Server (NTRS)

    Leventis, Nicholas; Zhang, Guo-Hui; Rawashdeh, Abdel-Monem M.; Sotiriou-Leventis, Chariklia; Gray, Hugh R. (Technical Monitor)

    2003-01-01

    In analogy to 4-(para-substituted benzoyl)-N-methylpyridinium cations (1-X's), the title species (2-X's, -X = -OCH3, -CH3, -H, -Br, -COCH3, -NO2) undergo two reversible, well-separated (E(sub 1/2) greater than or equal to 650 mV) one-electron reductions. The effect of substitution on the reduction potentials of 2-X's is much weaker than the effect of the same substituents on 1-X's: the Hammett rho-values are 0.80 and 0.93 for the 1st- and 2nd-e reduction of 2-X's vs. 2.3 and 3.3 for the same reductions of 1-X's, respectively. Importantly, the nitro group of 2-NO2 undergoes reduction before the 2nd-e reduction of the 4-benzoylpyridinium system. These results suggest that the redox potentials of the 4-benzoylpyridinium system can be course-tuned via p-benzoyl substitution and fine-tuned via para-benzyl substitution. Introducing the recently derived substituent constant of the -NO2(sup)- group (sigma para-NO2(sup)- = -0.97) yields an excellent correlation for the 3rd-e reduction of 2- NO2 (corresponding to the reduction of the carbonyl group) with the 2nd-e reduction of the other 2-X's, and confirms the electron donating properties of -NO2(sup)-.

  8. Synthesis and biological activity of novel amino acid-(N'-benzoyl) hydrazide and amino acid-(N'-nicotinoyl) hydrazide derivatives.

    PubMed

    Khattab, Sherine N

    2005-09-30

    The coupling reaction of benzoic acid and nicotinic acid hydrazides with N- protected L-amino acids including valine, leucine, phenylalanine, glutamic acid and tyrosine is reported. The target compounds, N-Boc-amino acid-(N;-benzoyl)- and N- Boc-amino acid-(N;-nicotinoyl) hydrazides 5a-5e and 6a-6e were prepared in very high yields and purity using N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl- methylene]-N-methyl-methanaminium hexafluorophosphate N-oxide (HATU) as coupling reagent. The antimicrobial activity of the Cu and Cd complexes of the designed compounds was tested. The products were deprotected affording the corresponding amino acid-(N;-benzoyl) hydrazide hydrochloride salts (7a-7e) and amino acid-(N;- nicotinoyl) hydrazide hydrochloride salts (8a-8e). These compounds and their Cu and Cd complexes were also tested for their antimicrobial activity. Several compounds showed comparable activity to that of ampicillin against S. aureus and E. coli.

  9. Structure and Function of the Unusual Tungsten Enzymes Acetylene Hydratase and Class II Benzoyl-Coenzyme A Reductase.

    PubMed

    Boll, Matthias; Einsle, Oliver; Ermler, Ulrich; Kroneck, Peter M H; Ullmann, G Matthias

    2016-01-01

    In biology, tungsten (W) is exclusively found in microbial enzymes bound to a bis-pyranopterin cofactor (bis-WPT). Previously known W enzymes catalyze redox oxo/hydroxyl transfer reactions by directly coordinating their substrates or products to the metal. They comprise the W-containing formate/formylmethanofuran dehydrogenases belonging to the dimethyl sulfoxide reductase (DMSOR) family and the aldehyde:ferredoxin oxidoreductase (AOR) families, which form a separate enzyme family within the Mo/W enzymes. In the last decade, initial insights into the structure and function of two unprecedented W enzymes were obtained: the acetaldehyde forming acetylene hydratase (ACH) belongs to the DMSOR and the class II benzoyl-coenzyme A (CoA) reductase (BCR) to the AOR family. The latter catalyzes the reductive dearomatization of benzoyl-CoA to a cyclic diene. Both are key enzymes in the degradation of acetylene (ACH) or aromatic compounds (BCR) in strictly anaerobic bacteria. They are unusual in either catalyzing a nonredox reaction (ACH) or a redox reaction without coordinating the substrate or product to the metal (BCR). In organic chemical synthesis, analogous reactions require totally nonphysiological conditions depending on Hg2+ (acetylene hydration) or alkali metals (benzene ring reduction). The structural insights obtained pave the way for biological or biomimetic approaches to basic reactions in organic chemistry.

  10. Rare earth complexes with 3-carbaldehyde chromone-(benzoyl) hydrazone: synthesis, characterization, DNA binding studies and antioxidant activity.

    PubMed

    Li, Yong; Yang, Zheng-Yin

    2010-01-01

    A new ligand, 3-carbaldehyde chromone-(benzoyl) hydrazone (L), was prepared by condensation of 3-carbaldehyde chromone with benzoyl hydrazine. Its four rare earth complexes have been prepared and characterized on the basis of elemental analyses, molar conductivities, mass spectra, (1)H NMR spectra, UV-vis spectra, fluorescence studies and IR spectra. The Sm(III) complex exhibits red fluorescence under UV light and the fluorescent properties of Sm(III) complex in solid state and different solutions were investigated. In addition, the DNA binding properties of the ligand and its complexes have been investigated by electronic absorption spectroscopy, fluorescence spectra, ethidium bromide displacement experiments, iodide quenching experiments, salt effect and viscosity measurements. Experimental results suggest that all the compounds can bind to DNA via an intercalation binding mode. Furthermore, the antioxidant activities of the ligand and its complexes were determined by superoxide and hydroxyl radical scavenging methods in vitro. The rare earth complexes were found to possess potent antioxidant activities that are better than those of the ligand alone.

  11. Stability of benzoyl peroxide in aromatic ester-containing topical formulations.

    PubMed

    Majekodunmi, Bola D; Lau-Cam, Cesar A; Nash, Robert A

    2007-01-01

    The chemical stability of benzoyl peroxide (BPO) was studied in solutions and gels. The solutions (1% w/v) were prepared in single solvents (alcohol USP, isopropyl alcohol USP, ethyl benzoate, C12-15 alkyl benzoate, dimethyl isosorbide, propylene carbonate, and acetone) and in binary and tertiary combinations of these solvents, with and without the addition of antioxidant(s) (BHT, BHA, eugenol, tert-butyl hydroquinone, Tenox-2, vitamin E, and vitamin C). The solutions were stored at 37 degrees C for 5 weeks, and each week were analyzed for remaining BPO. Using first-order kinetics, the stability of BPO in solution was found to decrease in the order: ternary>binary>single solvent systems. Regardless of the number of solvents present, the highest stability of BPO (t1/2>7.5 weeks) was attained in the presence of ethyl benzoate and C12-15 alkyl benzoate. The stability of BPO in solution did not change significantly with the addition of most antioxidants. The solutions in which BPO remained most stable were one in alcohol USP-ethyl benzoate-C12-15 alkyl benzoate (60:20:20; t1/2=18.15 weeks) and another in alcohol USP-C12-15 alkyl benzoate-isopropanol plus 0.1% BHT (65:20:15; t1/2=12.44 weeks). In turn, these two solutions were converted to homogeneous gels by the addition of Cab-O-Sil. The chemical stability of BPO in these gels was evaluated at 37 degrees, 45 degrees, 50 degrees, and 55 degrees C for 5 weeks. Parallel experiments were conducted with two commercial BPO products, a 2.5% tinted gel and 5% vanishing lotion. BPO was less stable in commercial products (t1/2

  12. Phototoxic effects of topical azelaic acid, benzoyl peroxide and adapalene were not detected when applied immediately before UVB to normal skin.

    PubMed

    Cetiner, Salih; Ilknur, Turna; Ozkan, Sebnem

    2004-01-01

    The enhancing effects on UVB erythema of topical agents applied on sun exposed areas are important due to their increased sunburn risk. Since the lesions in acne vulgaris are seen primarily on the face, the effects of topical agents used in acne treatment on the erythemogenicity of UVB is important. The aim of the present study was to examine whether azelaic acid cream, benzoyl peroxide gel, adapalene gel have the enhancing effects on UVB erythema which are widely used in the topical treatment of acne vulgaris. The minimal erythema dose (MED) was determined with phototest in 30 volunteers and the test was repeated with thin (0.1 cc/25 cm(2)) and thick (0.3 cc/25 cm(2)) azelaic acid cream, benzoyl peroxide gel, adapalene gel. The effects of each agent on MED was determined after 24 hours. MEDs of UVB were unaffected by azelaic acid cream, benzoyl peroxide gel and adapalene gel when applied immediately before irradiation. According to our results azelaic acid, benzoyl peroxide and adapalene do not seem to have enhancing effects on UVB erythema and thus increased sunburn risk.

  13. Benzoylation of Ergosterol through Nucleophilic Acyl Substitution and Subsequent Formation of Ergosterol Benzoate Endoperoxide by Reaction with Singlet Oxygen Generated by Photosensitization

    ERIC Educational Resources Information Center

    Roslaniec, Mary C.; Sanford, Elizabeth M.

    2011-01-01

    Reactive oxygen species such as singlet oxygen have been a major focus of research in medicine. The effect of singlet oxygen on sterols within biological membranes is becoming increasingly more important. Ergosterol, a vitamin D precursor, is one such sterol. The benzoylation of ergosterol and subsequent reaction with singlet oxygen to form an…

  14. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL...-), potassium salt (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180; CAS...

  15. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL...-), potassium salt (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180; CAS...

  16. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL...-), potassium salt (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180; CAS...

  17. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL...-), potassium salt (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180; CAS...

  18. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL...-), potassium salt (1:1). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180; CAS...

  19. Benzoylation of Ergosterol through Nucleophilic Acyl Substitution and Subsequent Formation of Ergosterol Benzoate Endoperoxide by Reaction with Singlet Oxygen Generated by Photosensitization

    ERIC Educational Resources Information Center

    Roslaniec, Mary C.; Sanford, Elizabeth M.

    2011-01-01

    Reactive oxygen species such as singlet oxygen have been a major focus of research in medicine. The effect of singlet oxygen on sterols within biological membranes is becoming increasingly more important. Ergosterol, a vitamin D precursor, is one such sterol. The benzoylation of ergosterol and subsequent reaction with singlet oxygen to form an…

  20. Randomized, Observer-blind, Split-face Compatibility Study with Clindamycin Phosphate 1.2%/Benzoyl Peroxide 3.75% gel and Facial Foundation Makeup.

    PubMed

    Bhatia, Neal; Pillai, Radhakrishnan

    2015-09-01

    Cosmetic compatibility in the treatment of acne is an important issue significantly impacting quality of life, but often overlooked, as dermatologists commonly recommended avoidance of cosmetic foundations when treating adult female patients. Fixed combinations of clindamycin/benzoyl peroxide are widely used in the treatment of acne, but little is known about the impact of their concomitant use with facial foundation. To assess the compatibility of clindamycin phosphate 1. 2%/benzoyl peroxide 3. 75% gel with foundation makeup for up to six hours after application. Twenty-nine female subjects applied makeup to their face after randomly applying clindamycin phosphate 1. 2%/benzoyl peroxide 3. 75% gel to one side of the face. Investigator and subject self- assessment included facial skin attributes, facial tolerability, and cosmetic compatibility post-application and at Hour 6; as well as cutaneous tolerability. No statistical difference was noted between the treated and untreated side of the face in terms of coverage, blotchiness, appearance, skin tone, or visual smoothness. Tolerability was excellent, with no erythema, edema, dryness, and peeling post-makeup application. For both the treated and untreated side, there was a slight lack of improvement in cosmetic appearance six hours post-makeup application. Clindamycin/benzoyl peroxide 3. 75% gel was shown to have excellent cosmetic compatibility with facial foundation.

  1. Separation of niobium and tantalum using a chelating ion exchange resin with N-benzoyl phenyl hydroxyl amine as functional group

    SciTech Connect

    Pobi, M.; Das, J. )

    1993-04-01

    Niobium is separated from Ta and V by elution with 0.5 M HF in a column of chelating resin containing N-benzoyl-N-phenyl-hydroxylamine (NBPHA) as a function group. Niobium and tantalum can also be separated using their differential distribution coefficient and elution behavior, monitored by radiometric and also be spectrophotometric methods. 15 refs., 1 fig., 2 tabs.

  2. Randomized, Observer-blind, Split-face Compatibility Study with Clindamycin Phosphate 1.2%/Benzoyl Peroxide 3.75% gel and Facial Foundation Makeup

    PubMed Central

    Pillai, Radhakrishnan

    2015-01-01

    Background: Cosmetic compatibility in the treatment of acne is an important issue significantly impacting quality of life, but often overlooked, as dermatologists commonly recommended avoidance of cosmetic foundations when treating adult female patients. Fixed combinations of clindamycin/benzoyl peroxide are widely used in the treatment of acne, but little is known about the impact of their concomitant use with facial foundation. Objective: To assess the compatibility of clindamycin phosphate 1. 2%/benzoyl peroxide 3. 75% gel with foundation makeup for up to six hours after application. Methods: Twenty-nine female subjects applied makeup to their face after randomly applying clindamycin phosphate 1. 2%/benzoyl peroxide 3. 75% gel to one side of the face. Investigator and subject self- assessment included facial skin attributes, facial tolerability, and cosmetic compatibility post-application and at Hour 6; as well as cutaneous tolerability. Results: No statistical difference was noted between the treated and untreated side of the face in terms of coverage, blotchiness, appearance, skin tone, or visual smoothness. Tolerability was excellent, with no erythema, edema, dryness, and peeling post-makeup application. For both the treated and untreated side, there was a slight lack of improvement in cosmetic appearance six hours post-makeup application. Conclusion: Clindamycin/benzoyl peroxide 3. 75% gel was shown to have excellent cosmetic compatibility with facial foundation. PMID:26430488

  3. Effect of temperature and concentration on benzoyl peroxide bleaching efficacy and benzoic acid levels in whey protein concentrate.

    PubMed

    Smith, T J; Gerard, P D; Drake, M A

    2015-11-01

    Much of the fluid whey produced in the United States is a by-product of Cheddar cheese manufacture and must be bleached. Benzoyl peroxide (BP) is currently 1 of only 2 legal chemical bleaching agents for fluid whey in the United States, but benzoic acid is an unavoidable by-product of BP bleaching. Benzoyl peroxide is typically a powder, but new liquid BP dispersions are available. A greater understanding of the bleaching characteristics of BP is necessary. The objective of the study was to compare norbixin destruction, residual benzoic acid, and flavor differences between liquid whey and 80% whey protein concentrates (WPC80) bleached at different temperatures with 2 different benzoyl peroxides (soluble and insoluble). Two experiments were conducted in this study. For experiment 1, 3 factors (temperature, bleach type, bleach concentration) were evaluated for norbixin destruction using a response surface model-central composite design in liquid whey. For experiment 2, norbixin concentration, residual benzoic acid, and flavor differences were explored in WPC80 from whey bleached by the 2 commercially available BP (soluble and insoluble) at 5 mg/kg. In liquid whey, soluble BP bleached more norbixin than insoluble BP, especially at lower concentrations (5 and 10 mg/kg) at both cold (4°C) and hot (50°C) temperatures. The WPC80 from liquid whey bleached with BP at 50°C had lower norbixin concentration, benzoic acid levels, cardboard flavor, and aldehyde levels than WPC80 from liquid whey bleached with BP at 4°C. Regardless of temperature, soluble BP destroyed more norbixin at lower concentrations than insoluble BP. The WPC80 from soluble-BP-bleached wheys had lower cardboard flavor and lower aldehyde levels than WPC80 from insoluble-BP-bleached whey. This study suggests that new, soluble (liquid) BP can be used at lower concentrations than insoluble BP to achieve equivalent bleaching and that less residual benzoic acid remains in WPC80 powder from liquid whey

  4. Benzoyl-L-arginine methyl ester (BAME)-esterase activity in human plasma during the gravidic-puerperal cycle.

    PubMed

    Salles Meirelles, R

    1977-01-01

    Benzoyl-L-arginine methyl ester (BAME)-esterase activity of plasma was measured in women going through the gravidic-puerperal cycle and compared with plasma of non-pregnant women. Plasma from women in the 36th to 40th week of pregnancy hydrolyzes BAME two times more rapidly than that from non-pregnant women. During pregnancy, BAME-esterase activity in plasma increases progressively up to the 40th week, decreases during labor, and after delivery reaches the same level as in non-pregnant women. The BAME-esterase activity of plasma was affected by the storage temperature, with differences demonstrable between -20 and -4 C and between pregnant and non-pregnant women.

  5. Mechanisms of the inhibition and catalysis by ionol of the chain decomposition of benzoyl peroxide in cellulose triacetate

    SciTech Connect

    Mikheev, Yu.A.; Guseva, L.N.; Mikheeva, L.E.; Toptygin, D.Ya.

    1987-09-01

    It was established that the sterically hindered phenol ionol inhibits the kinetic chains of allylation of a polymer by benzoyl peroxide (BP) and catalyzes the decomposition of BP according to a new pathway, only slightly influencing the initiated destruction of the macromolecules. Two types of free radicals are formed from ionol: sigma-complexes, responsible for the chain decomposition of BP, and phenoxyls, responsible for termination of the kinetic chains. The concept that the nonchain and chain steps of the decomposition of BP proceed in different structural zones of the polymer matrix - dissociation on the surface of microcells and chain propagation in the volume of the microcells of the polymer framework - was confirmed. It was shown that the conversion of BP in the presence of ionol is described by means of heterophase kinetics.

  6. Do tutorials on application method enhance adapalene-benzoyl peroxide combination gel tolerability in the treatment of acne?

    PubMed

    Kwon, Hyuck Hoon; Park, Seon Yong; Yoon, Ji Young; Min, Seonguk; Suh, Dae Hun

    2015-11-01

    Fixed-dose combination adapalene 0.1% and benzoyl peroxide 2.5% gel (A-BPO) has rarely been studied for Asian acne patients, while they have complained of local irritations more often when applying individual components. In this study, we compared A-BPO gel with benzoyl peroxide (BPO) in terms of efficacy and tolerability in Korean patients first, and assessed the clinical benefit of a dermatological tutorial on application technique in reducing irritations for A-BPO. This study was conducted as a single-blind controlled split-face trial for a 12-week period. Each half facial side of 85 patients was randomly assigned to either A-BPO or BPO. Success rate, lesion counts and safety profiles were evaluated (analysis I). During initial assignment, all patients were further randomized to either dermatological tutorial (DT) or non-tutorial (NT) subgroups depending on the presence of dermatologists' tutorials for application methods to their A-BPO sides. Clinical data of the A-BPO side was compared between two subgroups (analysis II). As a result, A-BPO gel outperformed BPO, demonstrating better efficacy in success rates and lesion counts as early as 1 week. However, A-BPO proved significantly less tolerable compared with both BPO and previous A-BPO data from Caucasians. Bioengineering measurements further confirmed clinical data (analysis I). The DT subgroup achieved much better tolerability with comparable therapeutic efficacies compared with the NT subgroup (analysis II). In conclusion, A-BPO demonstrated higher efficacies in acne compared with BPO in Korean patients, while skin irritation levels were notable concurrently. Dermatologists' education for application methods would significantly decrease these side-effects, maintaining superior efficacy levels.

  7. Anaerobic degradation of 2-aminobenzoic acid (anthranilic acid) via benzoyl-coenzyme A (CoA) and cyclohex-1-enecarboxyl-CoA in a denitrifying bacterium.

    PubMed Central

    Lochmeyer, C; Koch, J; Fuchs, G

    1992-01-01

    The enzymes catalyzing the initial reactions in the anaerobic degradation of 2-aminobenzoic acid (anthranilic acid) were studied with a denitrifying Pseudomonas sp. anaerobically grown with 2-aminobenzoate and nitrate as the sole carbon and energy sources. Cells grown on 2-aminobenzoate are simultaneously adapted to growth with benzoate, whereas cells grown on benzoate degrade 2-aminobenzoate several times less efficiently than benzoate. Evidence for a new reductive pathway of aromatic metabolism and for four enzymes catalyzing the initial steps is presented. The organism contains 2-aminobenzoate-coenzyme A ligase (2-aminobenzoate-CoA ligase), which forms 2-aminobenzoyl-CoA. 2-Aminobenzoyl-CoA is then reductively deaminated to benzoyl-CoA by an oxygen-sensitive enzyme, 2-aminobenzoyl-CoA reductase (deaminating), which requires a low potential reductant [Ti(III)]. The specific activity is 15 nmol of 2-aminobenzoyl-CoA reduced min-1 mg-1 of protein at an optimal pH of 7. The two enzymes are induced by the substrate under anaerobic conditions only. Benzoyl-CoA is further converted in vitro by reduction with Ti(III) to six products; the same products are formed when benzoyl-CoA or 2-aminobenzoyl-CoA is incubated under reducing conditions. Two of them were identified preliminarily. One product is cyclohex-1-enecarboxyl-CoA, the other is trans-2-hydroxycyclohexane-carboxyl-CoA. The complex transformation of benzoyl-CoA is ascribed to at least two enzymes, benzoyl-CoA reductase (aromatic ring reducing) and cyclohex-1-enecarboxyl-CoA hydratase. The reduction of benzoyl-CoA to alicyclic compounds is catalyzed by extracts from cells grown anaerobically on either 2-aminobenzoate or benzoate at almost the same rate (10 to 15 nmol min-1 mg-1 of protein). In contrast, extracts from cells grown anaerobically on acetate or grown aerobically on benzoate or 2-aminobenzoate are inactive. This suggests a sequential induction of the enzymes. Images PMID:1592816

  8. Solvent extraction behaviour of lanthanum(III), cerium(III), europium(III), thorium(IV) and uranium(VI) with 3-phenyl-4-benzoyl-5-isoxazolone.

    PubMed

    Jyothi, A; Rao, G N

    1990-04-01

    The extraction behaviour of La(III), Ce(III), Eu(III), Th(IV) and U(VI) with 3-phenyl-4- benzoyl-5-isoxazolone (HPBI) in chloroform has been studied. The mechanism of extraction and the species extracted have been identified. Extraction constants for each system have been calculated. The system has been used to separate Th(IV) from U(VI) and from La(III), Ce(III) and Eu(III). A comparison of the extraction constants with those for the 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (HPMBP) and thenoyltrifluoroacetone (HTTA) systems indicates that HPBI extracts these metal species better than HPMBP and HTTA do.

  9. Analytical studies of the interaction of Tb(III)-2-{[(4-methoxy benzoyl) oxy]} methyl benzoic acid binary complex with nucleosides

    NASA Astrophysics Data System (ADS)

    Shehata, A. M. A.; Azab, H. A.; El-assy, N. B.; Anwar, Z. M.; Mostafa, H. M.

    2016-01-01

    The interaction of Tb(III)-2-{[(4-methoxy benzoyl) oxy]} methyl benzoic acid binary complex with nucleosides (adenosine, cytidine, guanosine and inosine) was investigated using UV and fluorescence methods. The reaction of Tb-complex with cytidine, guanosine and adenosine is accompanied by shift to longer wavelength in the absorption band, while there is a blue shift in the absorption band with an enhancement in the molar absorptivity upon the reaction with inosine. The fluorescence intensity of Tb(III)-2-{[(4- methoxy benzoyl) oxy]} methyl benzoic acid binary complex at λ = 545 nm (5D4 → 7F5) was decreased with the addition of the nucleoside molecule following the order: cytidine > inosine > guanosine > adenosine.

  10. 4-Halo-1,3-oxazoles: Unambiguous structural assignment of 2-halo-2-benzoyl-2 H-azirine-3-carboxylates thermal ring expansion products

    NASA Astrophysics Data System (ADS)

    Lopes, Susy; Nunes, Cláudio M.; Fausto, Rui; Melo, Teresa M. V. D. Pinho e.

    2009-02-01

    IR spectroscopy in cryogenic argon matrix of methyl 4-chloro-5-phenyl-1,3-oxazole-2-carboxylate and methyl 4-chloro-5-phenylisoxazole-3-carboxylate was applied for the structural assignment of these isomeric heterocycles. It was demonstrated that methyl 2-benzoyl-2-halo-2 H-azirine-3-carboxylates undergo thermal ring expansion to give 4-halo-5-phenyl-1,3-oxazole-2-carboxylates and not the isomeric isoxazoles.

  11. Results of a Multicenter, Randomized, Controlled Trial of a Hydrogen Peroxide-based Kit versus a Benzoyl Peroxide-based Kit in Mild-to-moderate Acne.

    PubMed

    Veraldi, Stefano; Micali, Giuseppe; Berardesca, Enzo; Dall'Oglio, Federica; Sinagra, Jo Linda; Guanziroli, Elena

    2016-10-01

    Objective:To evaluate the efficacy and tolerability of a novel hydrogen peroxide-based regimen versus a benzoyl peroxide-based regimen in mild-to-moderate acne. Methods: In this eight-week multicenter study, patients were randomized to either a hydrogen peroxide-based or a benzoyl peroxide-based regimen.The primary outcome measure of clinical response was assessed using the Global Acne Grading System (GAGS) at baseline,four weeks, and eight weeks. At Week 8, a patient self-satisfaction questionnaire was administered. Investigators were also queried at that time regarding assessment of tolerability and cosmetic acceptability. Tolerability was also measured at each visit. Results: Both treatment regimens were associated with improvement of GAGS score at Week 8 compared to baseline (p<0.0001). GAGS score did not differ significantly between the two regimens over the same period (p=0.7765). No significant adverse events were reported or observed in either treatment arm. Both patients and investigators found both regimens to be similarly effective and cosmetically acceptable. Conclusion: A novel hydrogen peroxide-based regimen was shown to be comparable in efficacy, safety, and cosmetic acceptability to a benzoyl peroxide-based regimen in the treatment of mild-to-moderate acne.

  12. Results of a Multicenter, Randomized, Controlled Trial of a Hydrogen Peroxide-based Kit versus a Benzoyl Peroxide-based Kit in Mild-to-moderate Acne

    PubMed Central

    Micali, Giuseppe; Berardesca, Enzo; Dall’Oglio, Federica; Sinagra, Jo Linda; Guanziroli, Elena

    2016-01-01

    Objective:To evaluate the efficacy and tolerability of a novel hydrogen peroxide-based regimen versus a benzoyl peroxide-based regimen in mild-to-moderate acne. Methods: In this eight-week multicenter study, patients were randomized to either a hydrogen peroxide-based or a benzoyl peroxide-based regimen.The primary outcome measure of clinical response was assessed using the Global Acne Grading System (GAGS) at baseline,four weeks, and eight weeks. At Week 8, a patient self-satisfaction questionnaire was administered. Investigators were also queried at that time regarding assessment of tolerability and cosmetic acceptability. Tolerability was also measured at each visit. Results: Both treatment regimens were associated with improvement of GAGS score at Week 8 compared to baseline (p<0.0001). GAGS score did not differ significantly between the two regimens over the same period (p=0.7765). No significant adverse events were reported or observed in either treatment arm. Both patients and investigators found both regimens to be similarly effective and cosmetically acceptable. Conclusion: A novel hydrogen peroxide-based regimen was shown to be comparable in efficacy, safety, and cosmetic acceptability to a benzoyl peroxide-based regimen in the treatment of mild-to-moderate acne. PMID:27847549

  13. Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents

    PubMed Central

    Chen, Jianjun; Wang, Zhao; Li, Chien-Ming; Lu, Yan; Vaddady, Pavan K.; Meibohm, Bernd; Dalton, James T.; Miller, Duane D.; Li, Wei

    2010-01-01

    A series of 2-aryl-4-benzoyl-imidazoles (ABI) was synthesized as a result of structural modifications based on the previous set of 2-aryl-imidazole-4-carboxylic amide (AICA) derivatives and 4-substituted methoxylbenzoyl-aryl-thiazoles (SMART). The average IC50 of the most active compound (5da) was 15.7 nM. ABI analogs have substantially improved aqueous solubility (48.9 μg/mL for 5ga vs. 0.909 μg/mL for SMART-1, 0.137 μg/mL for paclitaxel, and 1.04 μg/mL for Combretastatin A4). Mechanism of action studies indicate that the anticancer activity of ABI analogs is through inhibition of tubulin polymerization by interacting with the colchicine binding site. Unlike paclitaxel and colchicine, the ABI compounds were equally potent against multidrug resistant cancer cells and the sensitive parental melanoma cancer cells. In vivo results indicated that 5cb was more effective than DTIC in inhibiting melanoma xenograph tumor growth. Our results suggest that the novel ABI compounds may be developed to effectively treat drug-resistant tumors. PMID:20919720

  14. Design, synthesis and biological evaluation of 4-benzoyl-1-dichlorobenzoylthiosemicarbazides as potent Gram-positive antibacterial agents.

    PubMed

    Paneth, Agata; Plech, Tomasz; Kaproń, Barbara; Hagel, Dominika; Kosikowska, Urszula; Kuśmierz, Edyta; Dzitko, Katarzyna; Paneth, Piotr

    2016-01-01

    Twelve 4-benzoyl-1-dichlorobenzoylthiosemicarbazides have been tested as potential antibacterials. All the compounds had MICs between 0.49 and 15.63 µg/ml toward Micrococcus luteus, Bacillus cereus, Bacillus subtilis and Staphylococcus epidermidis indicating, in most cases, equipotent or even more effective action than cefuroxime. In order to clarify if the observed antibacterial effects are universal, further research were undertaken to test inhibitory potency of two most potent compounds 3 and 11 on clinical isolates of Staphylococcus aureus. Compound 11 inhibited the growth of methicillin-sensitive S. aureus (MSSA) at MICs of 1.95-7.81 µg/ml, methicillin-resistant S. aureus (MRSA) at MICs of 0.49-1.95 µg/ml and MDR-MRSA at MIC of 0.98 and 3.90 µg/ml, respectively. Finally, inhibitory efficacy of 3 and 11 on planktonic cells and biofilms formation in clinical isolates of S. aureus and Haemophilus parainfluenzae was tested. The majority of cells in biofilm populations of MSSA and MRSA were eradicated at low level of 3, with MBICs in the range of 7.82-15.63 µg/ml.

  15. Enhanced unique pattern of hematopoietic cell mobilization induced by the CXCR4 antagonist 4F-benzoyl-TN14003.

    PubMed

    Abraham, Michal; Biyder, Katia; Begin, Michal; Wald, Hanna; Weiss, Ido D; Galun, Eithan; Nagler, Arnon; Peled, Amnon

    2007-09-01

    An increase in the number of stem cells in blood following mobilization is required to enhance engraftment after high-dose chemotherapy and improve transplantation outcome. Therefore, an approach that improves stem cell mobilization is essential. The interaction between CXCL12 and its receptor, CXCR4, is involved in the retention of stem cells in the bone marrow. Therefore, blocking CXCR4 may result in mobilization of hematopoietic progenitor and stem cells. We have found that the CXCR4 antagonist known as 4F-benzoyl-TN14003 (T-140) can induce mobilization of hematopoietic stem cells and progenitors within a few hours post-treatment in a dose-dependent manner. Furthermore, although T-140 can also increase the number of white blood cells (WBC) in blood, including monocytes, B cells, and T cells, it had no effect on mobilizing natural killer cells. T-140 was found to efficiently synergize with granulocyte colony-stimulating factor (G-CSF) in its ability to mobilize WBC and progenitors, as well as to induce a 660-fold increase in the number of erythroblasts in peripheral blood. Comparison between the CXCR4 antagonists T-140 and AMD3100 showed that T-140 with or without G-CSF was significantly more potent in its ability to mobilize hematopoietic stem cells and progenitors into blood. These results demonstrate that different CXCR4 antagonists may have different therapeutic potentials.

  16. The CXCR4 antagonist 4F-benzoyl-TN14003 stimulates the recovery of the bone marrow after transplantation.

    PubMed

    Abraham, M; Beider, K; Wald, H; Weiss, I D; Zipori, D; Galun, E; Nagler, A; Eizenberg, O; Peled, A

    2009-08-01

    Cytopenia represents a significant complication after chemotherapy, irradiation before bone marrow (BM) transplantation or as a therapy for cancer. The mechanisms that determine the pace of BM recovery are not fully understood. During the recovery phase after chemotherapy or irradiation, the signals for retention of white blood cells within the BM increase significantly. This leads to a delay in the release of WBC, which can be overcome by targeting the CXCR4 axis with the antagonist 4F-benzoyl-TN14003 (T140). The delay in the release of WBC is also accompanied by suppression in the production of progenitor cells and mature cells by the BM stroma. Administration of T140 to mice transplanted with BM cells stimulates the production of all types of progenitors and mature cells, and increases the exit of mature cells to the periphery. Moreover, addition of T140, but not AMD3100, to BM stromal cultures stimulates the production of mature cells and progenitors from all lineages. The unique ability of the CXCR4 antagonist, T140 to stimulate the production and exit of WBC cells may be used as a novel therapeutic approach to overcome cytopenia associated with treatments for cancer and BM transplantation.

  17. 2-Amino-3-(hy­droxy­meth­yl)pyridinium 2-benzoyl­benzoate monohydrate

    PubMed Central

    Odabaşoğlu, Hakkı Yasin; Büyükgüngör, Orhan; Avinç, Osman Ozan; Odabaşoğlu, Mustafa

    2012-01-01

    In the title hydrated salt, C6H9N2O+·C14H9O3 −·H2O, the dihedral angle between the benzene rings of the 2-benzoyl­benzoate anion is 82.04 (14)°, while the angles between the aromatic ring of the pyridinium cation and each of the benzene rings of the anion are 4.42 (14) and 82.04 (14)°. In the crystal, mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, generating a three-dimensional network with R 2 2(8), R 6 6(16) and R 4 4(6) motifs. The crystal packing is further stabilized by two π–π inter­actions, one between pyridinium rings, and another between the benzene benzoate and pyridinium rings of neighbouring mol­ecules, with centroid-to-centroid distances of 3.559 (2) and 3.606 (2) Å, respectively. PMID:22412594

  18. Efficacy of adapalene/benzoyl peroxide combination in moderate inflammatory acne and its impact on patient adherence.

    PubMed

    Gollnick, Harald P M; Funke, Gisela; Kors, Christian; Titzmann, Thomas; Jöstingmeyer, Petra; Jäckel, Andreas

    2015-06-01

    Adapalene 0.1 %/benzoyl peroxide (BPO) 2.5 % (Epiduo®) is the first, fixed-dose topical combination gel developed for the once-daily treatment of acne. The objective of this observational study was to assess efficacy and patient adherence under daily clinical practice conditions in a large population of young adults and adolescents (12 to 20 years) with moderate inflammatory acne. A total of 2 780 patients receiving adapalene-BPO were evaluated in this multicenter, open-label, prospective non-interventional observational study. Observation time per patient was approximately 12 weeks. Assessment parameters included changes in acne severity, treatment success, safety, and therapeutic adherence. After 12 weeks, the majority of patients (91.5 %) showed improvement of acne under adapalene-BPO treatment, with an initial therapeutic response noted after a median time of 14 days. Overall, 21.8 % of participants displayed complete resolution of visible acne lesions. Treatment adherence was assessed as good in 63.2 % of patients. The majority of individuals (69.5 %) experienced no or only mild local skin irritations. No serious adverse drug reactions (ADR) were reported during the course of the study. Adapalene-BPO is effective and safe in the treatment of moderate inflammatory acne. The fixed-dose combination and easy application simplifies the therapeutic regimen, leading to good treatment adherence in the majority of patients. © 2015 Deutsche Dermatologische Gesellschaft (DDG). Published by John Wiley & Sons Ltd.

  19. Synergistic efficacy of adapalene 0.1%-benzoyl peroxide 2.5% in the treatment of 3855 acne vulgaris patients.

    PubMed

    Tan, Jerry; Gollnick, Harald P M; Loesche, Christian; Ma, Y May; Gold, Linda Stein

    2011-08-01

    The adapalene-benzoyl peroxide (adapalene-BPO) combination gel is efficacious and safe in the treatment of acne vulgaris. We aimed in this pooled analysis to determine whether the adapalene-BPO combination demonstrates synergistic efficacy. Data were pooled and analyzed from three double-blind controlled studies, in which patients were randomized to receive adapalene-BPO, adapalene, BPO or vehicle once daily for 12 weeks. Efficacy assessments included percent reduction in lesion counts and Investigator's Global Assessment (IGA) success. Benefit of each treatment relative to vehicle was calculated by subtracting the vehicle result from the efficacy result. Synergy was defined as the benefit of the combination greater than the sum of benefits of adapalene and BPO monotherapies. Adapalene-BPO was significantly more efficacious than its monotherapies in decreasing lesion counts as early as week 1 and throughout the study (p < 0.05). Synergy in total lesion count reduction was observed up to week 8, contributing 48.7% of the benefit of adapalene-BPO relative to vehicle in decreasing total lesions at week 1. Synergy of the combination in IGA success was observed at weeks 1, 4, 8 and 12. In conclusion, the fixed-dose adapalene-BPO combination gel provides synergistic and significantly greater efficacy than its monotherapies in the treatment of acne vulgaris.

  20. Synthesis, structure, infrared and fluorescence spectra of new rare earth complexes with 6-hydroxy chromone-3-carbaldehyde benzoyl hydrazone

    NASA Astrophysics Data System (ADS)

    Wang, Bao-Dui; Yang, Zheng-Yin; Zhang, Ding-Wa; Wang, Yan

    2006-01-01

    A novel 6-hydroxy chromone-3-carbaldehyde benzoyl hydrazone ligand and its four complexes, [LnL2(NO3)2]NO3 [Ln = Eu(1), Sm(2), Tb(3), Dy(4)], were synthesized. The complexes were characterized by the elemental analyses, molar conductivity and IR spectra. The crystal and molecular structure of Sm(III) complex was determined by single-crystal X-ray diffraction: crystallized in the triclinic system, space group P-1, Z = 1, a = 11.037(4) Å, b = 14.770(5) Å, c = 15.032(7) Å, α = 60.583(4), β = 75.528(7), γ = 88.999(4), R1 = 0.0349. The fluorescence properties of complexes in the solid state and in the organic solvent were studied in detail, respectively. Under the excitation of ultraviolet light, strong red fluorescence of solid europium complex was observed. But the green fluorescence of solid terbium complex was not observed. These observations show that the ligand favor energy transfers to the emitting energy level of Eu3+. Some factors that influence the fluorescent intensity were also discussed.

  1. Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity

    NASA Astrophysics Data System (ADS)

    Odame, Felix; Hosten, Eric C.; Betz, Richard; Lobb, Kevin; Tshentu, Zenixole R.

    2015-11-01

    The reaction of benzoyl isothiocyanate with L-serine, L-proline, D-methionine and L-alanine gave 2-[(benzoylcarbamothioyl)amino]-3-hydroxypropanoic acid (I), 1-(benzoylcarbamothioyl)pyrrolidine-2-carboxylic acid (II), 2-[(benzoylcarbamothioyl)amino]-4-(methylsulfanyl)butanoic acid (III) and 2-[(benzoylcarbamothioyl)amino]propanoic acid (IV), respectively. The compounds have been characterized by IR, NMR, microanalyses and mass spectrometry. The crystal structures of all the compounds have also been discussed. Compound II showed rotamers in solution. DFT calculations of the frontier orbitals of the compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity of these compounds. The calculations indicated that the carboxylic acid group in these compounds is unreactive hence making the conversion to benzimidazoles via cyclization on the carboxylic acids impractical. This has been further confirmed by the reaction of compounds I-IV, respectively, with o-phenylene diamine which was unsuccessful but gave compound V.

  2. Topical therapy for acne in women: is there a role for clindamycin phosphate-benzoyl peroxide gel?

    PubMed

    Del Rosso, James Q

    2014-10-01

    Acne vulgaris (AV) in adult women is commonly encountered in clinical dermatology practice. This patient subset often experiences psychosocial effects that differ in some ways from those experienced by adolescent females with AV, as they were not expecting to have to deal with this disorder beyond their adolescent years. Most of the emphasis on therapy for adult women with AV has focused on use of oral contraceptives (OCs) and/or oral spironolactone, with little to no evaluation or discussion of topical agents in this patient group. This article provides an overview of AV in adult women and presents the results of a subanalysis of data from female patients who were treated in phase 3 studies with clindamycin phosphate (CP) 1.2%-benzoyl peroxide (BP) 2.5% gel once daily for facial AV. The subanalysis compared outcomes in females younger than 25 years and in those 25 years and older. Overall, the data showed that therapeutic outcomes were comparable between the 2 groups.

  3. Establishment of an activated peroxide system for low-temperature cotton bleaching using N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride.

    PubMed

    Xu, Changhai; Hinks, David; Sun, Chang; Wei, Qufu

    2015-03-30

    Cotton bleaching is traditionally carried out in strongly alkaline solution of hydrogen peroxide (H2O2) at temperatures close to the boil. Such harsh processing conditions can result in extensive water and energy consumptions as well as severe chemical damage to textiles. In this study, an activated peroxide system was established for low-temperature cotton bleaching by incorporating a bleach activator, namely N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride (TBBC) into an aqueous H2O2 solution. Experimental results showed that the TBBC-activated peroxide system exhibited the most effective bleaching performance in a pH range of 6-8 which could be approximated by adding sodium bicarbonate (NaHCO3). The TBBC/H2O2/NaHCO3 system led to rapid bleaching of cotton at a temperature as low as 50°C. In comparison with the hot alkaline peroxide bleaching system, the TBBC/H2O2/NaHCO3 system provided cotton fabric with an equivalent degree of whiteness, higher degree of polymerization, and slightly lower water absorbency. The new activated peroxide system may provide a more environmentally benign approach to cotton bleaching.

  4. In vitro antimicrobial activity of benzoyl peroxide against Propionibacterium acnes assessed by a novel susceptibility testing method.

    PubMed

    Okamoto, Kazuaki; Ikeda, Fumiaki; Kanayama, Shoji; Nakajima, Akiko; Matsumoto, Tatsumi; Ishii, Ritsuko; Umehara, Masatoshi; Gotoh, Naomasa; Hayashi, Naoki; Iyoda, Takako; Matsuzaki, Kaoru; Matsumoto, Satoru; Kawashima, Makoto

    2016-06-01

    Benzoyl peroxide (BPO), a therapeutic agent for acne vulgaris, was assessed for in vitro antimicrobial activity against Propionibacterium acnes using a novel broth microdilution testing that improved BPO solubility. We searched for a suitable culture medium to measure the minimum inhibitory concentration (MIC) of BPO against P. acnes and finally found the Gifu anaerobic medium (GAM) broth supplemented with 0.1(v/v)% glycerol and 2(v/v)% Tween 80, in which BPO dissolved up to 1250 μg/mL and P. acnes grew well. The MICs and minimum bactericidal concentrations (MBCs) of BPO against 44 clinical isolates of P. acnes collected from Japanese patients with acne vulgaris were determined by our testing method using the supplemented GAM broth. The MICs of BPO were 128 or 256 μg/mL against all isolates of P. acnes regardless of susceptibility to nadifloxacin or clindamycin. The MBCs of BPO were also 128 or 256 μg/mL against the same isolates. Moreover, BPO at the MIC showed a rapid bactericidal activity against P. acnes ATCC11827 in time-kill assay. In conclusion, we could develop a novel assay for the MIC and MBC determinations of BPO against P. acnes, which is reliable and reproducible as a broth microdilution testing and the present results suggest that BPO has a potent bactericidal activity against P. acnes.

  5. HIV-1 Reverse Transcriptase Structure with RNase H Inhibitor dihydroxy benzoyl naphthyl Hydrazone Bound at a Novel Site

    SciTech Connect

    Himmel,D.; Sarafianos, S.; Dharmasena, S.; Hossain, M.; McCoy-Simandle, K.; Ilina, T.; Clark, A.; Knight, J.; Julias, J.; et al.

    2007-01-01

    The rapid emergence of drug-resistant variants of human immunodeficiency virus, type 1 (HIV-1), has limited the efficacy of anti-acquired immune deficiency syndrome (AIDS) treatments, and new lead compounds that target novel binding sites are needed. We have determined the 3.15 {angstrom} resolution crystal structure of HIV-1 reverse transcriptase (RT) complexed with dihydroxy benzoyl naphthyl hydrazone (DHBNH), an HIV-1 RT RNase H (RNH) inhibitor (RNHI). DHBNH is effective against a variety of drug-resistant HIV-1 RT mutants. While DHBNH has little effect on most aspects of RT-catalyzed DNA synthesis, at relatively high concentrations it does inhibit the initiation of RNA-primed DNA synthesis. Although primarily an RNHI, DHBNH binds >50 {angstrom} away from the RNH active site, at a novel site near both the polymerase active site and the non-nucleoside RT inhibitor (NNRTI) binding pocket. When DHBNH binds, both Tyr181 and Tyr188 remain in the conformations seen in unliganded HIV-1 RT. DHBNH interacts with conserved residues (Asp186, Trp229) and has substantial interactions with the backbones of several less well-conserved residues. On the basis of this structure, we designed substituted DHBNH derivatives that interact with the NNRTI-binding pocket. These compounds inhibit both the polymerase and RNH activities of RT.

  6. The tolerability profile of clindamycin 1%/benzoyl peroxide 5% gel vs. adapalene 0.1%/benzoyl peroxide 2.5% gel for facial acne: results of a randomized, single-blind, split-face study.

    PubMed

    Gonzalez, Pablo; Vila, Ricardo; Cirigliano, Marcela

    2012-12-01

    Topical combination therapy, such as that with fixed-dose clindamycin/benzoyl peroxide (BPO) or adapalene/BPO, is the recommended first-line approach for the treatment of facial acne. To compare the tolerability of clindamycin 1%/BPO 5% gel vs. adapalene 0.1% BPO 2.5% gel for the first 2 weeks of treatment in patients with facial acne. Using a randomized, single-blind, split-face method, 48 patients with acne received both clindamycin/BPO and adapalene/BPO once daily for 2 weeks. The primary endpoint was investigator-assessed tolerability. Treatment efficacy, patient-assessed tolerability and satisfaction, and safety were also investigated. Forty-five patients completed treatment. Investigator-rated scores for erythema, dryness, and peeling were significantly higher with adapalene/BPO than clindamycin/BPO. Patients rated clindamycin/BPO as significantly more tolerable than adapalene/BPO for redness, dryness, burning, itching, and scaling. Investigator Static Global Assessment scores and lesion counts improved with both products, with no significant difference between treatments. Patients' Global Change Assessment showed a statistically significant difference in favor of clindamycin/BPO at week 1, but not week 2. Overall, >80% of patients were "satisfied" or "very satisfied" with treatment at week 2, but 63% of patients stated that they preferred clindamycin/BPO. Both products were well tolerated, with no serious adverse events (AEs), but a post hoc analysis indicated that treatment-related AEs, including irritation, dryness and erythema, were significantly less common with clindamycin/BPO. Clindamycin/BPO had a better tolerability profile than adapalene/BPO during 2 weeks of split-face treatment. Treatment satisfaction was highest with clindamycin/BPO. © 2012 Wiley Periodicals, Inc.

  7. Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4'-bipyridine cocrystal with their crystal structures.

    PubMed

    Tamboli, Majid I; Bahadur, Vir; Gonnade, Rajesh G; Shashidhar, Mysore S

    2014-11-01

    Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8, (1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4'-bipyridine molecules in its cocrystal, C21H18O8·C10H8N2, (1)·BP, inhibits the intermolecular benzoyl-group transfer reaction. In (1), molecules are assembled around the crystallographic twofold screw axis (b axis) to form a helical self-assembly through conventional O-H···O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy group (nucleophile, Nu) in proximity, with a preorganized El···Nu geometry favourable for the acyl transfer reaction. In the cocrystal (1)·BP, the dibenzoate and bipyridine molecules are arranged alternately through O-H···N interactions. The presence of the bipyridine molecules perturbs the regular helical assembly of the dibenzoate molecules and thus restricts the solid-state reactivity. Hence, unlike the parent dibenzoate crystals, the cocrystals do not exhibit benzoyl-transfer reactions. This approach is useful for increasing the stability of small molecules in the crystalline state and could find application in the design of functional solids.

  8. Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives.

    PubMed

    Matin, Mohammed Mahbubul; Nath, Amit R; Saad, Omar; Bhuiyan, Mohammad M H; Kadir, Farkaad A; Abd Hamid, Sharifah Bee; Alhadi, Abeer A; Ali, Md Eaqub; Yehye, Wageeh A

    2016-08-27

    Benzyl α-l-rhamnopyranoside 4, obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound 5 which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside 7 in reasonable yield. Di-O-acetyl derivative of benzoate 7 was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides 5 and 6 exhibited slight distortion from regular ¹C₄ conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides 4-8 were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives 4-8 were 0.49 < Pa < 0.60 (where Pa is probability 'to be active') as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives 4-8 were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures 4-8 have not been reported with antimicrobial activity, making it a possible valuable lead compound.

  9. Antinociceptive effects of (O-methyl)-N-benzoyl tyramine (riparin I) from Aniba riparia (Nees) Mez (Lauraceae) in mice.

    PubMed

    Araújo, F L O; Melo, C T V; Rocha, N F M; Moura, B A; Leite, C P; Amaral, J F; Barbosa-Filho, J M; Gutierrez, S J C; Vasconcelos, S M M; Viana, G S B; de Sousa, Francisca Cléa Florenço

    2009-10-01

    The present study examined the antinociceptive effects of (O-methyl) N-benzoyl-tyramine (riparin I, ripI) isolated from the unripe fruit of Aniba riparia in chemical and thermal behavioral models of pain, such as acetic acid-induced abdominal writhing, formalin, and hot-plate tests in mice. Moreover, the involvement of the nitric oxide pathway as well as the opioid system in the antinociceptive action of ripI in the formalin test was investigated. RipI was administered both orally and intraperitoneally to male mice at single doses of 25 and 50 mg/kg. In the acetic acid-induced abdominal writhing, ripI decreased the number of writhings at both doses. In addition, in the formalin test, ripI reduced the paw licking time at both phases of the test. The effect of the highest dose of ripI in mice formalin test on the early phase was not reversed by naloxone (opioid receptor antagonist) but it was reversed by l-arginine (a nitric oxide precursor) in the late phase, suggesting that ripI may not act through opioid system and possibly acts through inhibition of nitric oxide pathway. In the hot-plate test, ripI increased the reaction time in the hot-plate test at the dose of 25 mg/kg, i.p., confirming the result found in the formalin test. Based on the obtained results, it is suggested that ripI presents antinociceptive activity that may be due to peripheral mechanisms (nitric oxide pathway) and central mechanisms, discarding the involvement of opioid system.

  10. Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives

    PubMed Central

    Matin, Mohammed Mahbubul; Nath, Amit R.; Saad, Omar; Bhuiyan, Mohammad M. H.; Kadir, Farkaad A.; Abd Hamid, Sharifah Bee; Alhadi, Abeer A.; Ali, Md. Eaqub; Yehye, Wageeh A.

    2016-01-01

    Benzyl α-l-rhamnopyranoside 4, obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound 5 which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside 7 in reasonable yield. Di-O-acetyl derivative of benzoate 7 was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides 5 and 6 exhibited slight distortion from regular 1C4 conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides 4–8 were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives 4–8 were 0.49 < Pa < 0.60 (where Pa is probability ‘to be active’) as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives 4–8 were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures 4–8 have not been reported with antimicrobial activity, making it a possible valuable lead compound. PMID:27618893

  11. Community study of fixed-combination adapalene 0.1% and benzoyl peroxide 2.5% in acne.

    PubMed

    Troielli, Patricia A; Asis, Beatriz; Bermejo, Alcira; Bittar, Mario; Cabrera, Hugo; Castro, Carla; Chouela, Ezequiel; Cordero, Andrés; Dobrinin, Roberto; Escobar, Sergio; Fortino, Mirta; Galimberti, Daniel; Galimberti, Gaston; Giovo, Maria Elsa; Gomez, Beatriz; Gras, Maria del Carmen; Ibarra, Mónica; Kizlansky, Viviana; Chabbert, Patricio Martinez; Ramonda, Sergio

    2010-01-01

    A new fixed-dose combination formulation of adapalene 0.1% and benzoyl peroxide (BPO) 2.5% has shown excellent efficacy and safety in registration studies; however, it can be difficult to judge the real-world performance of a product using only the results from controlled clinical trials. This 12-week, open-label, community-based study evaluated adapalene/BPO in 91 patients with mild to moderate acne (20-50 inflammatory lesions and 30-100 noninflammatory lesions) who were treated at dermatology centers throughout Argentina. The study evaluated efficacy, described the most common side effects, determined tolerability, and assessed the level of patient satisfaction with treatment. By week 12, there were statistically significant reductions in both inflammatory and noninflammatory lesions (80.6% and 69.3% from baseline, respectively; P < .001); there were also significant improvements in the Investigator's Global Assessment scores (median score, 2.9 at baseline and 1.0 at week 12; P < .001). By week 12, 67% of patients were rated clear or almost clear by investigators. Local tolerability was good overall. When cutaneous irritation was present, it typically occurred in the first 2 weeks of treatment and improved or resolved with continuing therapy. Patients were highly satisfied with the results of treatment, and 74% of patients felt that they had marked or total improvement by week 12. Patient survey also revealed that 94% rated the efficacy as good or very good and 87.5% rated tolerability as good or very good. A significant majority (81%) felt that the treatment met expectations, and 62% perceived that improvement had been rapid during adapalene/BPO therapy. These results demonstrate that adapalene/BPO has good efficacy and tolerability in routine practice, resulting in continuous reductions in lesion counts throughout the study. Adapalene/BPO therapy is also associated with high patient satisfaction, which is important for therapeutic adherence and satisfaction

  12. Preadolescent moderate acne vulgaris: a randomized trial of the efficacy and safety of topical adapalene-benzoyl peroxides.

    PubMed

    Eichenfield, Lawrence F; Draelos, Zoe; Lucky, Anne W; Hebert, Adelaide A; Sugarman, Jeffrey; Stein Gold, Linda; Rudisill, Diane; Liu, Hong; Manna, Vasant

    2013-06-01

    Evaluate the efficacy and safety of adapalene 0.1%-benzoyl peroxide 2.5% gel (adapalene-BPO) in patients 9-11 years old with acne vulgaris.
    Enrolled subjects were male or female, with a score of 3 (moderate) on the Investigator's Global Assessment (IGA) scale. Subjects were randomized to receive adapalene-BPO or vehicle once daily for up to 12 weeks. Efficacy was evaluated by success rate (percentage of subjects rated "clear" or "almost clear") at each visit, median percentage changes from baseline in total, inflammatory and non-inflammatory lesion counts at each visit, the Children's Dermatology Life Quality Index (C DLQI) at baseline and week 12, and the Parent Assessment of Acne at week 12. Safety was assessed through evaluations of adverse events (AEs) and local tolerability [erythema, scaling, dryness, and stinging/burning on scales ranging from 0 (none) to 3 (severe)].
    A total of 142 subjects were randomized to adapalene-BPO and 143 to vehicle. At study endpoint (week 12), adapalene-BPO was significantly superior to vehicle regarding treatment success (49.3% vs 15.9%, respectively), and regarding percentage reduction in total lesion counts (68.6% vs 19.3%), inflammatory (63.2% vs 14.3%), and non-inflammatory lesion counts (70.7% vs 14.6%) (all P<.001). More subjects using adapalene-BPO reported that their acne had no effect on their quality of life, and parents noted that their child's acne significantly improved. Adapalene-BPO was well tolerated, with mean tolerability scores less than 1 (mild).
    In preadolescents with acne, adapalene-BPO leads to significantly superior treatment success and lesion count reduction compared to vehicle.

  13. Digital videography assessment of patients' experiences using adapalene-benzoyl peroxide gel in the treatment of acne vulgaris.

    PubMed

    Feldman, Steven R; Fried, Richard G; Herndon, James H; Johnson, Lori; Preston, Norman; Gottschalk, Ronald W; Caveney, Scott W

    2012-08-01

    Acne profoundly affects patients' lives, but the effect of treatment is not fully characterized. The purpose of this study was to explore patients' experiences and viewpoints regarding treatment for mild to moderate acne vulgaris. This was an open-label, single-center study of 30 patients with mild to moderate acne vulgaris, treated with adapalene 0.1%/benzoyl peroxide 2.5% (adapalene-BPO gel) once daily for 12 weeks. An acne-specific quality of life questionnaire (Acne-QoL©) was conducted. Each subject's global assessment (SGA) was recorded at baseline and weeks 4, 8, and 12. Photographs were taken and video interviews were recorded. Local tolerability assessments and incidence of adverse events were documented. A statistically significant number of patients were clear/almost clear (treatment success) at week 12 (P<.001). At week 12, patients experienced a 44.1% and 57.1% mean reduction in inflammatory and noninflammatory lesions, respectively. By week 12, 67% of the patients in the video population (n=27) believed they had achieved treatment success (P<.001). Patients reported higher Acne-QoL© scores at week 12 compared to baseline, indicating better quality of life after treatment with adapalene-BPO gel (P<.001 for all domains). No unexpected adverse or serious adverse events were reported. This was an open-label study of 12 weeks duration. Overall, patients with mild to moderate acne treated with adapalene-BPO gel showed significant improvement in disease severity and quality of life. The video recordings chronicled the patients' experiences throughout the treatment process.

  14. Successful co-encapsulation of benzoyl peroxide and chloramphenicol in liposomes by a novel manufacturing method - dual asymmetric centrifugation.

    PubMed

    Ingebrigtsen, Sveinung G; Škalko-Basnet, Nataša; de Albuquerque Cavalcanti Jacobsen, Cristiane; Holsæter, Ann Mari

    2017-01-15

    Encapsulation of more than one active pharmaceutical ingredient into nanocarriers such as liposomes is an attractive approach to achieve a synergic drug effect and less complicated dosing schedules in multi-drug treatment regimes. Liposomal drug delivery in acne treatment may improve drug efficiency by targeted delivery to pilosebaceous units, reduce adverse effects and improve patient compliance. We therefore aimed to co-encapsulate benzoyl peroxide (BPO) and chloramphenicol (CAM) into liposomes using the novel liposome processing method - dual asymmetric centrifugation (DAC). Liposomes were formed from soybean lecithin, propylene glycol and distilled water (2:1:2w/v/v ratio), forming a viscous liposome dispersion. Liposomes containing both drugs (BPO-CAM-Lip), single drug (BPO-Lip and CAM-Lip), and empty liposomes were prepared. Drug entrapment of BPO and CAM was determined by a newly developed HPLC method for simultaneous detection and quantification of both drugs. Encapsulation of around 50% for BPO and 60% for CAM respectively was obtained in both single-drug encapsulated formulations (BPO-Lip and CAM-Lip) and co-encapsulated formulations (BPO-CAM-Lip). Liposome sizes were comparable for all liposome formulations, ranging from 130 to 150nm mean diameter, with a polydispersity index <0.2 for all formulations. CAM exhibited a sustained release from all liposomal formulations, whereas BPO appeared retained within the liposomes. BPO retention could be attributed to its poor solubility. However, HaCaT cell toxicity was found dependent on BPO released from the liposomes. In the higher concentration range (4%v/v), liposomal formulations were less cytotoxic than the corresponding drug solutions used as reference. We have demonstrated that DAC is a fast, easy, suitable method for encapsulation of more than one drug within the same liposomes.

  15. Para-(benzoyl)-phenylalanine as a potential inhibitor against LpxC of Leptospira spp.: homology modeling, docking, and molecular dynamics study.

    PubMed

    Pradhan, Dibyabhaba; Priyadarshini, Vani; Munikumar, Manne; Swargam, Sandeep; Umamaheswari, Amineni; Bitla, Aparna

    2014-01-01

    Leptospira interrogans, a Gram-negative bacterial pathogen is the main cause of human leptospirosis. Lipid A is a highly immunoreactive endotoxic center of lipopolysaccharide (LPS) that anchors LPS into the outer membrane of Leptospira. Discovery of compounds inhibiting lipid-A biosynthetic pathway would be promising for dissolving the structural integrity of membrane leading to cell lysis and death of Leptospira. LpxC, a unique enzyme of lipid-A biosynthetic pathway was identified as common drug target of Leptospira. Herein, homology modeling, docking, and molecular dynamics (MD) simulations were employed to discover potential inhibitors of LpxC. A reliable tertiary structure of LpxC in complex with inhibitor BB-78485 was constructed in Modeller 9v8. A data-set of BB-78485 structural analogs were docked with LpxC in Maestro v9.2 virtual screening workflow, which implements three stage Glide docking protocol. Twelve lead molecules with better XP Gscore compared to BB-78485 were proposed as potential inhibitors of LpxC. Para-(benzoyl)-phenylalanine - that showed lowest XP Gscore (-10.35 kcal/mol) - was predicted to have best binding affinity towards LpxC. MD simulations were performed for LpxC and para-(benzoyl)-phenylalanine docking complex in Desmond v3.0. Trajectory analysis showed the docking complex and inter-molecular interactions was stable throughout the entire production part of MD simulations. The results indicate para-(benzoyl)-phenylalanine as a potent drug molecule against leptospirosis. An animated Interactive 3D Complement (I3DC) is available in Proteopedia at http://proteopedia.org/w/Journal:JBSD:10.

  16. Classification of benzoyl peroxide as safe and effective and revision of labeling to drug facts format; topical acne drug products for over-the-counter human use; final rule.

    PubMed

    2010-03-04

    We, the Food and Drug Administration (FDA), are issuing this final rule to include benzoyl peroxide as a generally recognized as safe and effective (GRASE) active ingredient in over-the-counter (OTC) topical acne drug products. In addition, this final rule includes new warnings and directions required for OTC acne drug products containing benzoyl peroxide. We are also revising labeling for OTC topical acne drug products containing resorcinol, resorcinol monoacetate, salicylic acid and/or sulfur to meet OTC drug labeling content and format requirements in a certain FDA regulation. This final rule is part of our ongoing review of OTC drug products and represents our conclusions on benzoyl peroxide in OTC acne drug products.

  17. Synthesis, Structure and Antibacterial Activity of Potent DNA Gyrase Inhibitors: N′-Benzoyl-3-(4-Bromophenyl)-1H-Pyrazole-5-Carbohydrazide Derivatives

    PubMed Central

    Yin, Yong; Yuan, Rong-Ju; Ma, Jian; Zhu, Hai-Liang

    2013-01-01

    A total of 19 novel (3a–3s) N′-benzoyl-3-(4-bromophenyl)-1H-pyrazole-5-carbohydrazide analogs were designed, synthesized, and evaluated for biological activities as potential DNA gyrase inhibitors. The results showed that compound 3k can strongly inhibit Staphylococcus aureus DNA gyrase and Bacillus subtilis DNA gyrase (with IC50 of 0.15 µg/mL and 0.25 µg/mL, respectively). Structure-activity relationships were also discussed base on the biological and docking simulation results. PMID:23922790

  18. FT-IR and Raman spectroscopic and DFT studies of anti-cancer active molecule N-{(meta-ferrocenyl) Benzoyl} - L-Alanine - Glycine ethyl ester

    NASA Astrophysics Data System (ADS)

    Xavier, T. S.; Kenny, Peter T. M.; Manimaran, D.; Joe, I. Hubert

    2015-06-01

    FT-Raman and FT-IR spectra of N-{(meta-ferrocenyl) Benzoyl} - L-alanine - glycine ethyl ester were recorded in solid phase. The optimized molecular geometry, the vibrational wavenumbers, the infrared intensities and the Raman scattering intensities were calculated by using density functional method(B3LYP) with 6-31G(d, p) basis set. Vibrational assignment of the molecule was done by using potential energy distribution analysis. Natural bond orbital analysis, Mulliken charge analysis and HOMO-LUMO energy were used to elucidate the reasons for intra molecular charge transfer. Docking studies were conducted to predict its anticancer activity.

  19. 3-O-Benzyl-6-O-benzoyl-1,2-O-isopropil­idene-5-C-nitro­methyl-a-d-glucofuran­ose

    PubMed Central

    Pampín, Begoña; Valencia, Laura; Estévez, Juan C.; Estévez, Ramón J.

    2009-01-01

    The title compound, C24H27NO9, is one of the epimers of the Henry reaction of 3-O-benzyl-6-O-benzoyl-2-O-isopropyl­idene-a-d-glucofuran-5-one with nitro­methane. The conformation of the five membered rings is as expected from the precursor compound and the mol­ecule is folded with a dihedral angle of 51.4 (2)° between the aromatic rings. One O—H⋯O hydrogen bond and some intra­molecular and inter­molecular C—H⋯O inter­actions are observed in the structure. PMID:21581936

  20. N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring.

    PubMed

    Yoneda, Tetsuya; Tabata, Hidetsugu; Tasaka, Tomohiko; Oshitari, Tetsuta; Takahashi, Hideyo; Natsugari, Hideaki

    2015-04-09

    The stereochemistry of N-benzoyl-1,5-benzothiazepine and its S-oxide derivatives as vasopressin receptor ligands was examined in detail by freezing the conformation with a methyl group at the C6 or C9 of 1,5-benzothiazepine. It was revealed that the active forms recognized by the receptors are (cis,aS) for 1,5-benzothiazepine (5-7)-II and (cis,1S,aS) (syn) for its S-oxide (8-10)-II. The C9-methyl derivative of 1,5-benzothiazepine S-oxide (10-II) was designed and synthesized, achieving the putative active syn-isomer.

  1. Synthesis, structure and antibacterial activity of potent DNA gyrase inhibitors: N'-benzoyl-3-(4-bromophenyl)-1H-pyrazole-5-carbohydrazide derivatives.

    PubMed

    Sun, Juan; Lv, Peng-Cheng; Yin, Yong; Yuan, Rong-Ju; Ma, Jian; Zhu, Hai-Liang

    2013-01-01

    A total of 19 novel (3a-3s) N'-benzoyl-3-(4-bromophenyl)-1H-pyrazole-5-carbohydrazide analogs were designed, synthesized, and evaluated for biological activities as potential DNA gyrase inhibitors. The results showed that compound 3k can strongly inhibit Staphylococcus aureus DNA gyrase and Bacillus subtilis DNA gyrase (with IC50 of 0.15 µg/mL and 0.25 µg/mL, respectively). Structure-activity relationships were also discussed base on the biological and docking simulation results.

  2. Optimization and validation of high-performance chromatographic condition for simultaneous determination of adapalene and benzoyl peroxide by response surface methodology.

    PubMed

    Chen, Yi-Cheng; Tsai, Pi-Ju; Huang, Yaw-Bin; Wu, Pao-Chu

    2015-01-01

    The aim of this study was to develop a simple and reliable high-performance chromatographic (HPLC) method for simultaneous analysis of adapalene and benzoyl peroxide in pharmaceutical formulation by response surface methodology (RSM). An optimized mobile phase composed of acetonitrile, tetrahydrofuran and water containing 0.1% acetic acid at a ratio of 25:50:25 by volume was successfully predicted by using RSM. An isocratic separation was achieved by using the condition. Furthermore, the analytical method was validated in terms of specificity, linearity, accuracy and precision in a range of 80% to 120% of the expected concentration. Finally, the method was successfully applied to the analysis of a commercial product.

  3. Sub-group Analyses from a Trial of a Fixed Combination of Clindamycin Phosphate 1.2% and Benzoyl Peroxide 3.75% Gel for the Treatment of Moderate-to-severe Acne Vulgaris

    PubMed Central

    Korotzer, Andrew

    2015-01-01

    Background: Acne vulgaris is commonplace and can be difficult to manage. Providing an effective and well-tolerated treatment may lead to improved adherence, increased patient satisfaction, and improved clinical outcomes. Methods: A review of efficacy, safety, and cutaneous tolerability of clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel in 498 patients with moderate-to-severe acne vulgaris enrolled in a multicenter Phase III study randomized to receive active or vehicle once daily for 12 weeks, including the most recent post-hoc analyses. Results: Significantly superior reductions in lesion counts were observed with clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel from Week 4, with median percent reductions in inflammatory and noninflammatory lesions from baseline of 68.4 and 57.9 percent, respectively (bothp<0.001 versus vehicle). More than half (55.1%) of the severe acne vulgaris patients treated with clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel achieved ≥2-grade improvement from baseline in their Evaluator’s Global Severity Score, and almost a third of the adolescent acne vulgaris patients (32.4%) achieved at least a marked improvement in their acne vulgaris as early as Week 2. In adult female acne overall treatments success was achieved in 52.7 percent of patients treated with clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel. Overall, and in the specific subpopulations, clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel was well-tolerated with a similar adverse event profile to vehicle. Limitations: Post-hoc analyses from a single clinical trial with demographic imbalances that could potentially confound the results. Conclusion: Clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel appears to be effective in treating acne across various clinically relevant sub-groups. PMID:26705445

  4. Kinetics and mechanisms for the two-phase reaction between aqueous aniline and benzoyl chloride in chloroform, with and without pyridine catalysis

    SciTech Connect

    Wamser, C.C.; Yates, J.A.

    1989-01-06

    This paper reports relative rates and product yields for the reaction of aniline with benzoyl chloride under conditions in which the two reactants begin in separate immiscible phases. Typically the aniline is initially in an aqueous phase over a chloroform phase containing benzoyl chloride, and the lower solution is stirred slowly. Under these conditions, the observed reaction rate, monitored by appearance of chloride into the aqueous phase, is slower than the rate of mass transport of aniline from the aqueous to the chloroform phase. Addition of pyridine as a nucleophilic catalyst significantly increases the reaction rate, in particular when the pyridine is initially in the chloroform phase. The observed rate of chloride ion appearance in the pyridine-catalyzed reaction exceeds the sum of the rates of aniline transport (from water) and benzoylpyridinium chloride transport (into water), indicating that reaction occurs in both phases. In the uncatalyzed reaction, the product is benzanilide, in high yield (80-90%). The benzanilide yields are lower in the pyridine-catalyzed reactions (37-70%), where hydrolysis to benzoic acid competes significantly. 13 references, 3 figures, 3 tables.

  5. Peroxisomal ATP-Binding Cassette Transporter COMATOSE and the Multifunctional Protein ABNORMAL INFLORESCENCE MERISTEM Are Required for the Production of Benzoylated Metabolites in Arabidopsis Seeds1[W

    PubMed Central

    Bussell, John D.; Reichelt, Michael; Wiszniewski, Andrew A.G.; Gershenzon, Jonathan; Smith, Steven M.

    2014-01-01

    Secondary metabolites derived from benzoic acid (BA) are of central importance in the interactions of plants with pests, pathogens, and symbionts and are potentially important in plant development. Peroxisomal β-oxidation has recently been shown to contribute to BA biosynthesis in plants, but not all of the enzymes involved have been defined. In this report, we demonstrate that the peroxisomal ATP-binding cassette transporter COMATOSE is required for the accumulation of benzoylated secondary metabolites in Arabidopsis (Arabidopsis thaliana) seeds, including benzoylated glucosinolates and substituted hydroxybenzoylcholines. The ABNORMAL INFLORESCENCE MERISTEM protein, one of two multifunctional proteins encoded by Arabidopsis, is essential for the accumulation of these compounds, and MULTIFUNCTIONAL PROTEIN2 contributes to the synthesis of substituted hydroxybenzoylcholines. Of the two major 3-ketoacyl coenzyme A thiolases, KAT2 plays the primary role in BA synthesis. Thus, BA biosynthesis in Arabidopsis employs the same core set of β-oxidation enzymes as in the synthesis of indole-3-acetic acid from indole-3-butyric acid. PMID:24254312

  6. Adapalene/Benzoyl Peroxide Gel 0.3%/2.5%: A Safe and Effective Acne Therapy in All Skin Phototypes.

    PubMed

    Alexis, Andrew F; Cook-Bolden, Fran E; York, J P

    2017-06-01

    BACKGROUND: Acne affects individuals of all races and ethnicities; however, lighter and darker skin phototypes face different treatment challenges that may affect treatment response and tolerability. This analysis investigated possible differences in the efficacy and safety of the fixed dose combination of 0.3% adapalene with 2.5% benzoyl peroxide (A/BPO gel 0.3%/2.5%) in subjects with Fitzpatrick Skin Types (FST) I-VI.

    METHODS: This was a post-hoc analysis of a Phase 3, multicenter, randomized, double-blind, parallel-group study of moderate to severe acne in subjects with FST I-VI. Subjects received A/BPO gel 0.3%/2.5%, A/BPO gel 0.1%/2.5% (benchmark), or vehicle, once daily for 12 weeks. Efficacy measurements included success rate (IGA of Clear or Almost Clear), change in inflammatory and noninflammatory lesions from baseline to week 12, safety, and tolerability. The intent to treat (ITT) and safety populations were analyzed. Demographics and disposition were analyzed with descriptive statistics; categorical variables by frequency and percentage; and continuous variables with means, medians, minimum, maximum, and standard deviations.

    RESULTS: The A/BPO gel 0.3%/2.5% treatment group included 128 subjects with FST I-III, and 89 subjects with FST IV-VI. At week 12, A/BPO gel 0.3%/2.5% was safe, tolerable, and significantly superior to vehicle for all FST and severity groups in inflammatory and noninflammatory lesion reduction (P less than equal to .05). Compared to baseline, 32% of subjects with FST I-III were clear or almost clear, compared to 7% in the vehicle group (P=.001). In FST IV-VI, 28% of subjects were clear or almost clear, compared to 15% for vehicle (P=NS). In all treatment groups and skin phototypes, week 12 tolerability scores were similar to baseline scores, and tolerability scores for most subjects of all skin phototypes were "none" or "mild" for all measures.

    SUMMARY: We report that the fixed dose combination of A/BPO gel 0

  7. The efficacy, safety, and tolerability of adapalene versus benzoyl peroxide in the treatment of mild acne vulgaris: a randomized trial.

    PubMed

    Babaeinejad, S H; Fouladi, R F

    2013-07-01

    Topical treatments, such as adapalene and benzoyl peroxide (BPO), are popular in mild-to-moderate acne vulgaris. This study aimed to compare the efficacy, safety and tolerability of adapalene and BPO in mild acne vulgaris. In this single-center, randomized, double-blind, clinical trial, 60 patients with mild acne vulgaris received either topical adapalene 0.1% gel or topical BPO 2.5% gel on their face once daily for two months. The changes of acne lesion count (efficacy), any adverse effect (safety), and the patients' overall satisfaction (tolerability) were compared after 3 months of follow-up. In both groups the mean number of noninflammatory, inflammatory and total lesions decreased significantly from baseline (10.77±5.54, 9.73±5.09, and 20.50±7.54, respectively in adapalene group; 11.50±5.92, 8.43±5.45, and 19.93±9.01, respectively in BPO group) to the third month (1.70±1.68, 0.33±0.66, and 0.50±0.78, respectively in adapalene group; 4.23±4.14, 0.33±0.71, and 4.13±4.44, respectively in BPO group; P<0.001 for all), posttreatment. Although the mean number of inflammatory lesions was significantly lower in BPO receivers only at first month (P =0.001), the mean number of noninflammatory and total lesions was significantly lower in adapalene group at second (P = 0.04 and 0.03, respectively) and third (P =0.02 and <0.001, respectively) months, posttreatment. The adverse events were minimal and self-limited (26.7% in adapalene group, 20% in BPO group, p=0.54). The patients' overall satisfaction was good to excellent in 93.3% of adapalene receivers vs. 73.3% in BPO group (P=0.08). Both topical adapalene 0.1% and BPO 2.5% gels seem safe and effective in mild acne vulgaris, with a marginal tendency toward the former.

  8. The efficacy, safety and tolerability of adapalene versus benzoyl peroxide in the treatment of mild acne vulgaris; a randomized trial.

    PubMed

    Babaeinejad, S H; Fouladi, R F

    2013-09-01

    Topical treatments, such as adapalene and benzoyl peroxide (BPO), are popular in mild-to-moderate acne vulgaris. This study aimed to compare the efficacy, safety and tolerability of adapalene and BPO in mild acne vulgaris. In this single-center, randomized, double-blind, clinical trial, 60 patients with mild acne vulgaris received either topical adapalene 0.1% gel or topical BPO 2.5% gel on their face once daily for two months. The changes of acne lesion count (efficacy), any adverse effect (safety), and the patients' overall satisfaction (tolerability) were compared after 3 months of follow-up. In both groups the mean number of noninflammatory, inflammatory and total lesions decreased significantly from baseline (10.77±5.54, 9.73±5.09, and 20.50±7.54, respectively in adapalene group; 11.50±5.92, 8.43±5.45, and 19.93±9.01, respectively in BPO group) to the third month (1.70±1.68, 0.33±0.66, and 0.50±0.78, respectively in adapalene group; 4.23±4.14, 0.33±0.71, and 4.13±4.44, respectively in BPO group; P<0.001 for all), posttreatment. Although the mean number of inflammatory lesions was significantly lower in BPO receivers only at first month (P=0.001), the mean number of noninflammatory and total lesions was significantly lower in adapalene group at second (P= 0.04 and 0.03, respectively) and third (P=0.02 and <0.001, respectively) months, posttreatment. The adverse events were minimal and self-limited (26.7% in adapalene group, 20% in BPO group, P=0.54). The patients' overall satisfaction was good-excellent in 93.3% of adapalene receivers vs. 73.3% in BPO group (P=0.08). Both topical adapalene 0.1% and BPO 2.5% gels seem safe and effective in mild acne vulgaris, with a marginal tendency toward the former.

  9. Formulation and evaluation of a topical niosomal gel containing a combination of benzoyl peroxide and tretinoin for antiacne activity.

    PubMed

    Gupta, Ankush; Singh, Sima; Kotla, Niranjan G; Webster, Thomas J

    2015-01-01

    A skin disease, like acne, is very common and normally happens to everyone at least once in their lifetime. The structure of the stratum corneum is often compared with a brick wall, with corneocytes surrounded by the mortar of the intercellular lipid lamellae. One of the best options for successful drug delivery to the affected area of skin is the use of elastic vesicles (niosomes) which can be transported through the skin through channel-like structures. In this study, a combination of tretinoin (keratolytic agent) and benzoyl peroxide (BPO) (a potent antibacterial) was given by using niosomes as promising carriers for the effective treatment of acne by acting on a pathogenic site. In this section, niosomal gel formulation encapsulated drugs have been evaluated for in vitro, ex vivo, and in vivo, for their predetermined characteristics; and finally the stability of the niosome gel was tested at different temperature conditions for understanding of the storage conditions required for maintaining the quality of formulation attributes. The prepared niosome was found to be in the range of 531 nm with a zeta potential of -43 mV; the entrapment efficiencies of tretinoin (TRA) and BPO niosomes were found to be 96.25%±0.56% and 98.75%±1.25%, respectively. The permeated amount of TRA and BPO from the niosomal gel after 24 hours was calculated as 6.25±0.14 μg/cm(2) and 5.04±0.014 μg/cm(2), respectively. A comparative drug retention study in Wistar rat skin using cream, an alcoholic solution, and a niosomal gel showed 11.54 μg, 2.68 μg, and 15.54 μg amounts of TRA and 68.85 μg, 59.98 μg, and 143.78 μg amounts of BPO were retained in the layers of skin, respectively. In vivo studies of the niosomal gel and antiacne cream of TRA and BPO showed that the niosomal gel was more efficacious than the antiacne cream because niosomal gels with a 4.16-fold lower dose of BPO provided the same therapeutic index at targeted sites in comparison to the antiacne cream.

  10. Cyclization of nitriles. XXIV. Reactions of cyanamide derivatives of thiocarbamic acids with cyanothioacetamide. Crystal structure of 2-allylamino-4-amino-5-benzoyl-1,3-thiazole

    SciTech Connect

    Nesterov, V.N.; Sharanin, Yu.A.; Shestopalov, A.M.; Shklover, V.E.; Struchkov, Yu.T.

    1988-09-20

    2-Allylamino-4-amino-5-aroyl-1,3-thiazoles were obtained from S-alkylisoureas. An x-ray crystallographic investigation of 2-allylamino-4-amino-5-benzoyl-1,3-thiazole was undertaken. Dimethyl dithiocarbamate was used in the synthesis of 2-amino-4-methylthio-5-cyano-1H-pyrimidine-6-thione and, from the latter, 4-allylthio-2-amino-6-methylthio-5-cyanopyrimidine. The latter is easily quaternized by the action of iodine to 4-amino-3-iodomethyl-7-methylthio-8-cyano-2,3-dihydrothiazolo(3,2-c)pyrimidinium triiodide. In reaction with iodine 2-allyl-amino-1,3-thiazoles form N-allyl-N-iodo derivatives of 1,3-thiazole and not imidazo(2,3-b)thiazolium salts.

  11. Vibrational and theoretical analysis of pentyl-4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate.

    PubMed

    Arı, Hatice; Büyükmumcu, Zeki; Özpozan, Talat; İlhan, İlhan Özer; Bahadır, Özlem

    2013-06-01

    Infrared spectrum of the compound, pentyl-4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate (PBDPPC) has been measured. Conformational search through relaxed scan has been carried out to find the most stable conformational isomer. After the full geometry optimization for the most stable conformer using B3LYP and BLYP hybrid functionals of Density Functional Theory (DFT), vibrational normal modes have been calculated at the same theoretical levels. Potential Energy Distribution (PED) of each normal mode has been calculated by means of VEDA4 to obtain contributions of internal coordinates to the normal modes. Natural Bond Orbital (NBO) analysis has been performed to get insights into the possible hydrogen bonding sites for all the conformational isomers. Copyright © 2013 Elsevier B.V. All rights reserved.

  12. Synthesis, characterization, antioxidant activity and DNA-binding studies of two rare earth(III) complexes with naringenin-2-hydroxy benzoyl hydrazone ligand.

    PubMed

    Li, Tian-Rong; Yang, Zheng-Yin; Wang, Bao-Dui; Qin, Dong-Dong

    2008-08-01

    Two novel rare earth complexes, Y(III) complex (1) and Eu(III) complex (2), with naringenin-2-hydroxy benzoyl hydrazone ligand were synthesized and characterized. The interaction of the two metal complexes and the free ligand with calf thymus DNA (CT DNA) was investigated by electronic absorption spectroscopy, fluorescence spectroscopy and viscosity measurement. All the experimental evidences indicate that these three compounds can strongly bind to CT DNA via an intercalation mechanism. The intrinsic binding constants of the Y(III) complex (1), Eu(III) complex (2) and the free ligand with CT DNA were 2.1 x 10(4), 8.5 x 10(4) and 1.6 x 10(4) M(-1), respectively. Furthermore, the antioxidant activity of the metal complexes was determined by hydroxyl radical scavenging method in vitro.

  13. Optimization and Validation of High-Performance Chromatographic Condition for Simultaneous Determination of Adapalene and Benzoyl Peroxide by Response Surface Methodology

    PubMed Central

    Huang, Yaw-Bin; Wu, Pao-Chu

    2015-01-01

    The aim of this study was to develop a simple and reliable high-performance chromatographic (HPLC) method for simultaneous analysis of adapalene and benzoyl peroxide in pharmaceutical formulation by response surface methodology (RSM). An optimized mobile phase composed of acetonitrile, tetrahydrofuran and water containing 0.1% acetic acid at a ratio of 25:50:25 by volume was successfully predicted by using RSM. An isocratic separation was achieved by using the condition. Furthermore, the analytical method was validated in terms of specificity, linearity, accuracy and precision in a range of 80% to 120% of the expected concentration. Finally, the method was successfully applied to the analysis of a commercial product. PMID:25793581

  14. Maintenance therapy for acne vulgaris: efficacy of a 12-month treatment with adapalene-benzoyl peroxide after oral isotretinoin and a review of the literature.

    PubMed

    Bettoli, Vincenzo; Borghi, Alessandro; Zauli, Stefania; Toni, Giulia; Ricci, Michela; Giari, Silvia; Virgili, Annarosa

    2013-01-01

    The correct therapeutic management of acne should include a maintenance therapy with topical retinoids to prevent recurrences after discontinuing a successful treatment. To investigate the efficacy of a 12-month maintenance treatment with adapalene 0.1% and benzoyl peroxide (BPO) 2.5% fixed combination gel to control acne relapse after treatment with oral isotretinoin (OI). The study consisted of 2 phases, namely an active treatment phase (AP) and a maintenance phase (MP). In the AP, 70 consecutive patients with moderate to severe acne were treated with OI until acne remission. Then, patients entered the MP and were treated with adapalene-BPO fixed combination once daily for 12 months. The primary efficacy parameter was the relapse rate during MP. Sixty-eight patients completed the study. Relapse occurred in 2 patients (2.94%). Comparing our findings with published data, the association of a topical retinoid and BPO seems to provide favorable evidence for this combination as maintenance therapy.

  15. A subgroup analysis to evaluate the efficacy and safety of adapalene-benzoyl peroxide topical gel in black subjects with moderate acne.

    PubMed

    Alexis, Andrew F; Johnson, Lori A; Kerrouche, Nabil; Callender, Valerie D

    2014-02-01

    Three multicenter, randomized, double blind, parallel-group, placebo controlled studies involving 3,855 subjects established the safety and efficacy of an adapalene benzoyl peroxide topical gel in the treatment of acne for all skin types. The data from these 3 studies were pooled and the subgroup of self-identified black subjects was analyzed separately. Significantly more black subjects had IGA success with adapalene-BPO than with vehicle at week 12. Significantly more black subjects also had decreased total, inflammatory, and noninflammatory lesion counts with adapalene-BPO that were seen as early as week 1. Adapalene-BPO was well tolerated in the black subjects included in this analysis and no cases of treatment-related PIH were observed. Similar results were obtained for this subgroup as the overall population from the 3 studies. Based on the results from this analysis, adapalene-BPO is a safe and effective treatment for acne in black skin.

  16. Vibrational and theoretical analysis of pentyl-4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate

    NASA Astrophysics Data System (ADS)

    Arı, Hatice; Büyükmumcu, Zeki; Özpozan, Talat; İlhan, İlhan Özer; Bahadır, Özlem

    2013-06-01

    Infrared spectrum of the compound, pentyl-4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate (PBDPPC) has been measured. Conformational search through relaxed scan has been carried out to find the most stable conformational isomer. After the full geometry optimization for the most stable conformer using B3LYP and BLYP hybrid functionals of Density Functional Theory (DFT), vibrational normal modes have been calculated at the same theoretical levels. Potential Energy Distribution (PED) of each normal mode has been calculated by means of VEDA4 to obtain contributions of internal coordinates to the normal modes. Natural Bond Orbital (NBO) analysis has been performed to get insights into the possible hydrogen bonding sites for all the conformational isomers.

  17. Crystal structure of 5-O-benzoyl-2,3-O-iso­propyl­idene-d-ribono-1,4-lactone

    PubMed Central

    Bortoluzzi, Adailton J.; Silveira, Gustavo P.; Sá, Marcus M.

    2017-01-01

    In the title compound, C15H16O6, obtained from the acyl­ation reaction between 2,3-O-iso­propyl­idene-d-ribono-1,4-lactone and benzoyl chloride, the known absolute configuration for the lactone moiety of the ester substituent has been confirmed. The five-membered rings of the bicyclic lactone–dioxolane moiety both show envelope conformations and form a dihedral angle of 19.82 (7)° between the lactone ring and the benzene ring. In the crystal, mol­ecules of the acyl­ated sugar are linked by very weak inter­molecular C—H⋯O inter­actions, forming a three-dimensional network. PMID:28316820

  18. Stabilization of the bicontinuous cubic phase in siloxane-terminated mesogens, 1,2-bis[4'-(n-(oligodimethylsiloxyl)alkoxy)benzoyl]hydrazine.

    PubMed

    Kutsumizu, Shoichi; Tokiwa, Issei; Kawafuchi, Akane; Miwa, Yohei; Yamamura, Yasuhisa; Saito, Kazuya

    2016-04-07

    The introduction of oligodimethyl siloxane segments at the termini of the alkyl tails has been employed to stabilize the bicontinuous cubic (Cub(bi)) phase of a chain-core-chain type molecule having a 1,2-bis(benzoyl)hydrazine central core with two chains attached at the 4' position of each benzoyl moiety. In this study, three silylated molecules, bis-C10Si2, bis-C10Si3, and C10Si2-C8C=C, were synthesized, where "CnSim" represents the number of carbon and silicon atoms in the chain and "bis" indicates the two chains being the same, whereas the last one is asymmetric with respect to the core. The phase behaviors were examined by using polarized optical microscopy, differential scanning calorimetry, and X-ray diffraction techniques. All three compounds form Cub(bi) phases and their syntheses were compared including their parent compound bis-C18. It was clearly revealed that the introduction of oligodimethyl siloxane segments effectively suppresses the crystallization at low temperatures, and as a result stabilizes the Cub(bi) phases, in an extreme case down to room temperature. The semi-quantitative analyses in terms of lattice constant and three-dimensional electron density map help us to better understand the self-assembly process in the Cub(bi) phases. The study also revealed that the introduction of oligodimethyl siloxane segments is not only an alternative for the hydrocarbon segment but also is able to provide a versatile design strategy for obtaining stable Cub(bi) phases.

  19. Ultrasound-assisted phase-transfer catalysis: benzoylation of sodium 4-acetylphenoxide by dual-site phase-transfer catalyst in a tri-liquid system.

    PubMed

    Yang, Hung-Ming; Chiu, Chun-Cheng

    2011-01-01

    A novel dual-site phase-transfer catalyst (PTC) was prepared and used to conduct the benzoylation of sodium 4-acetylphenoxide by ultrasound-assisted third-liquid phase-transfer catalysis. The catalyst 1,4-bis(tributylammoniomethyl)benzene dibromide (BTBAMBB) was synthesized from the reaction of p-xylylene dibromide and tributylamine in toluene at 70°C. The dual-site PTC was employed to form the third-liquid phase by extra addition of 0.04-0.05 mol of NaCl into 10 cm(3) of water. In the condition of 0.0425 mol of NaCl at 30°C, the catalytic intermediate in the third-liquid phase reached a maximum value. Almost 80% of the catalyst was transferred from the aqueous phase into the third-liquid phase. The distributions of the catalytic intermediate and dual-site PTC between phases and the kinetics of benzoylation of sodium 4-acetylphenoxide catalyzed by BTBAMBB with ultrasound irradiation were performed. The pseudo-first-order kinetic equation was applied to describe the overall reaction. Under ultrasound irradiation (28 kHz/300 W) in a batch reactor, the yield of product 4-acetylphenyl benzoate in the organic phase was 98.1% in 2 min at 30°C and 250 rpm with the apparent rate constant k(app) to be 0.0075 s(-1), which was 6 times faster than that without using ultrasound (yield=14.4%, k(app)=0.0013 s(-1)). The present study provides a green method to synthesize esters by ultrasound-assisted third-liquid phase-transfer catalysis. Copyright © 2010 Elsevier B.V. All rights reserved.

  20. Attenuation of benzoyl peroxide-mediated cutaneous oxidative stress and hyperproliferative response by the prophylactic treatment of mice with spearmint (Mentha spicata).

    PubMed

    Saleem, M; Alam, A; Sultana, S

    2000-10-01

    The modulating effect of spearmint (Mentha spicata) on benzoyl peroxide-induced responses of tumor promotion in murine skin was investigated. Benzoyl peroxide (BPO) is an effective cutaneous tumor promoter acting through the generation of oxidative stress, induction of ornithine decarboxylase activity and by enhancing DNA synthesis. BPO treatment (20 mg/animal) increased cutaneous microsomal lipid peroxidation and hydrogen peroxide generation. The activity of cutaneous antioxidant enzymes, namely catalase, glutathione peroxidase, glutathione reductase and glutathione S-transferase, was decreased and the level of cutaneous glutathione was depleted. BPO treatment also induced the ornithine decarboxylase activity and enhanced the [3H]thymidine uptake in DNA synthesis in murine skin. Prophylactic treatment of mice with spearmint extract (10, 15 and 20 mg/kg) 1 hr before BPO treatment resulted in the diminution of BPO-mediated damage. The susceptibility of cutaneous microsomal membrane to lipid peroxidation and hydrogen peroxide generation was significantly reduced (P < 0.05 ). In addition, depleted levels of glutathione, inhibited activity of glutathione dependent and antioxidant enzymes were recovered to a significant level (P < 0.01, P < 0.05 and P < 0.01, respectively). Similarly, the elevated ornithine decarboxylase activity and enhanced thymidine uptake in DNA synthesis was inhibited significantly (P < 0.05 ) in a dose-dependent manner. The protective effect of spearmint was dose dependent in all parameters. The result suggests that spearmint is an effective chemopreventive agent that may suppress BPO-induced cutaneous oxidative stress, toxicity and hyperproliferative effects in the skin of mice.

  1. Clindamycin phosphate 1.2%-benzoyl peroxide (5% or 2.5%) plus tazarotene cream 0.1% for the treatment of acne.

    PubMed

    Dhawan, Sunil S; Gwazdauskas, Jennifer

    2013-02-01

    Acne is a multifactorial chronic dermatosis that can be effectively treated with adjuvant medications. The objective of our study was to compare the tolerability and efficacy of 2 adjuvant therapies combining clindamycin phosphate 1.2%-benzoyl peroxide 5% (CLNP-BPO5) or clindamycin phosphate 1.2%-benzoyl peroxide 2.5% (CLNP-BPO2.5) fixed-dose gels with tazarotene (TZ) cream 0.1% (CLNP-BPO5/TZ vs CLNP-BPO2.5/TZ) when applied topically once daily for 12 weeks in participants with moderate to severe facial acne. Forty participants were randomized to receive CLNP-BPO5/TZ or CLNP-BPO2.5/TZ in a parallel-group study and were evaluated at baseline as well as weeks 1, 2, 4, 8, and 12 (or at early termination). In both groups, tolerability assessments increased by week 1 but gradually returned toward baseline levels by week 12. At week 4, the mean change in burning/stinging was significantly higher in the CLNP-BPO5/TZ group compared with the CLNP-BPO2.5/TZ group (P<.05). No other significant differences were observed for the tolerability, efficacy, quality of life (QOL), or participant preference assessments. Our study shows that CLNP-BPO5 or CLNP-BPO2.5 fixed-dose gels in combination with TZ cream 0.1% are generally well-tolerated and effective treatments of moderate to severe facial acne when applied once daily for up to 12 weeks.

  2. Crystal structure and computational studies of (3Z)-4-benzoyl-3-[(2,4-di­nitro­phen­yl)hydrazinyl­idene]-5-phenyl­furan-2(3H)-one

    PubMed Central

    Köysal, Yavuz; Bülbül, Hakan; İlhan, İlhan Özer; Akın, Nazenin; Dege, Necmi

    2016-01-01

    In the mol­ecular structure of the title compound, C23H14N4O7, the furan, di­nitro­phenyl and phenyl rings are almost in the same plane (r.m.s. deviation = 0.127 Å), with the benzoyl ring inclined by a dihedral angle of 56.4 (1)° to the three-ring system. A bifurcated intra­molecular N—H⋯(O,O) hydrogen bond is present. In the crystal, adjacent mol­ecules are linked by C—H⋯O hydrogen bonds into chains parallel to [001]. A π–π stacking inter­action between the benzoyl and di­nitro­phenyl moieties contributes to the crystal packing. Theoretical calculations using DFT(B3YLP) methods were used to confirm the mol­ecular structure. PMID:27980848

  3. Acid- and base-catalysis in the mononuclear rearrangement of some (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole in toluene: effect of substituents on the course of reaction.

    PubMed

    D'Anna, Francesca; Frenna, Vincenzo; Ghelfi, Franco; Marullo, Salvatore; Spinelli, Domenico

    2011-04-15

    The reaction rates for the rearrangement of eleven (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole 3a-k into the relevant (2-aryl-5-phenyl-2H-1,2,3-triazol-4-yl)ureas 4a-k in the presence of trichloroacetic acid or of piperidine have been determined in toluene at 313.1 K. The results have been related to the effect of the aryl substituent by using Hammett and/or Ingold-Yukawa-Tsuno correlations and have been compared with those previously collected in a protic polar solvent (dioxane/water) as well as with those on the analogous rearrangement of the corresponding (Z)-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole 1a-k in benzene. Some light can thus be shed on the general differences of chemical reactivity between protic polar (or dipolar aprotic) and apolar solvents.

  4. Dapsone gel 5% in combination with adapalene gel 0.1%, benzoyl peroxide gel 4% or moisturizer for the treatment of acne vulgaris: a 12-week, randomized, double-blind study.

    PubMed

    Fleischer, Alan B; Shalita, Alan; Eichenfield, Lawrence F; Abramovits, William; Lucky, Anne; Garrett, Steven

    2010-01-01

    To evaluate the safety and efficacy of dapsone gel 5% in the treatment of acne when used in combination with adapalene gel 0.1%, benzoyl peroxide gel 4% or moisturizer. This was a twelve-week, randomized, double-blind study. Patients aged 12 years and older (n=301) applied dapsone gel twice daily and were randomly assigned (1:1:1) to one of three additional treatments, applied once daily. By week 12, dapsone gel combined with any of the three additional treatments reduced the mean number of inflammatory lesions. However, the authors did not detect a significant difference in the reduction of inflammatory lesions when dapsone was used in combination with adapalene gel or with benzoyl peroxide gel compared to the dapsone plus moisturizer combination group (P=0.052 for both versus moisturizer combination). Patients treated with dapsone gel combined with adapalene showed a significantly better response in reduction in non-inflammatory and total acne lesion count than those who received the moisturizer combination. Local adverse reactions in all three treatment groups were minimal and generally mild in severity. Dapsone gel in combination with adapalene gel or benzoyl peroxide gel is safe and well tolerated for the treatment of acne vulgaris.

  5. Efficacy and Tolerability of a Combined 445nm and 630nm Over-the-counter Light Therapy Mask with and without Topical Salicylic Acid versus Topical Benzoyl Peroxide for the Treatment of Mild-to-moderate Acne Vulgaris

    PubMed Central

    Swenson, Nicole; Macri, Angela; Manway, Mitchell; Paparone, Paige

    2016-01-01

    Objective: To evaluate the efficacy and tolerance of a combined 445nm/630nm light therapy mask for the treatment of mild-to-moderate acne vulgaris with and without topical 1% salicylic acid with retinol versus 2.5% benzoyl peroxide. Design: A 12-week evaluator-blinded, randomized study. Subjects were randomized to be treated with the 445nm/630nm light therapy mask alone, benzoyl peroxide, or 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol. Participants: Healthy male and female subjects 12 to 35 years old with Fitzpatrick skin types I to VI and mild-to-moderate facial acne vulgaris. Measurements: The primary endpoint was the change in the number of inflammatory acne lesions after 12 weeks of treatment. Secondary endpoints included the change in noninflammatory acne lesions, change in total acne lesions, change in Investigator Global Acne Assessments, and overall responder rate. Results: 445nm/630nm light therapy mask-treated subjects showed a 24.4-percent improvement in inflammatory acne lesions (p<0.01) versus 17.2 percent (p<0.05) and 22.7 percent (p<0.01) in benzoyl peroxide and 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol, respectively, a 19.5-percent improvement in noninflammatory lesions (p<0.001) versus 6.3 and 4.8 percent for benzoyl peroxide and 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol, respectively. Subjects in the 445nm/630nm light therapy mask group also achieved a 19.0-percent improvement in the Investigator Global Acne Assessment (p<0.001) versus 4.7 percent in benzoyl peroxide and 13.9 percent in 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol (p<0.01). Treatments were well-tolerated overall with trends toward less early irritation in the 445nm/630nm light therapy mask group. Conclusion: 445nm/630nm light therapy mask appears to be a safe and effective therapy for mild-to-moderate acne. PMID:27354885

  6. Sensitive quantitation of polyamines in plant foods by ultrasound-assisted benzoylation and dispersive liquid-liquid microextraction with the aid of experimental designs.

    PubMed

    Pinto, Edgar; Melo, Armindo; Ferreira, Isabel M P L V O

    2014-05-14

    A new method involving ultrasound-assisted benzoylation and dispersive liquid-liquid microextraction was optimized with the aid of chemometrics for the extraction, cleanup, and determination of polyamines in plant foods. Putrescine, cadaverine, spermidine, and spermine were derivatized with 3,5-dinitrobenzoyl chloride and extracted by dispersive liquid-liquid microextraction using acetonitrile and carbon tetrachloride as dispersive and extraction solvents, respectively. Two-level full factorial design and central composite design were applied to select the most appropriate derivatization and extraction conditions. The developed method was linear in the 0.5-10.0 mg/L range, with a R(2) ≥ 0.9989. Intra- and interday precisions ranged from 0.8 to 6.9% and from 3.0 to 10.3%, respectively, and the limit of detection ranged between 0.018 and 0.042 μg/g of fresh weight. This method was applied to the analyses of six different types of plant foods, presenting recoveries between 81.7 and 114.2%. The method is inexpensive, versatile, simple, and sensitive.

  7. Synthesis, multiple interactions and spectroscopy analysis of ethyl-4-[(benzoyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate: Through experimental and quantum chemical approaches

    NASA Astrophysics Data System (ADS)

    Singh, R. N.; Kumar, Amit; Tiwari, R. K.; Rawat, Poonam

    2013-03-01

    The carboxaldehydes of pyrrole form important class of precursors for synthesis of acid hydrazide-hydrazones and their derivatives which show the various applications. A novel hydrazide-hydrazone of pyrrole: Ethyl-4-[(benzoyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate (3) has been synthesized by condensation of ethyl-4-formyl-3,5-dimetyl-1H-pyrrole-2-carboxylate and benzohydrazide. The product was characterized by spectroscopy methods (FT-IR, 1H NMR, UV-Vis and DART Mass) and quantum chemical calculations. The calculated thermodynamic parameters show that the formation of (3) is exothermic and spontaneous at room temperature. The local electronic descriptors analysis and molecular electrostatic potential surface were used to predict the sites and nature of interactions which indicate the dimer formation through multiple interaction through Nsbnd H⋯O and C-H⋯O. The vibrational analysis shows red shifts in vNsbnd H and vCdbnd O as result of dimer formation. Topological and energetic parameters generated by AIM show the nature of interactions in dimer. The interaction energies of dimer formation using DFT and AIM calculations are found to be 14.19 and 15.19 kcal/mol respectively. Ellipticity analysis confirms the presence of resonance assisted heteronuclear H-bonding in dimer.

  8. Comparison of chloroxylenol 0.5% plus salicylic acid 2% cream and benzoyl peroxide 5% gel in the treatment of acne vulgaris: a randomized double-blind study.

    PubMed

    Boutli, F; Zioga, M; Koussidou, T; Ioannides, D; Mourellou, O

    2003-01-01

    A 12-week double-blind randomized study was performed to compare benzoyl peroxide 5% (BP) gel and chloroxylenol 0.5% plus salicylic acid 2% (PCMX + SA) cream (Nisal cream) for efficacy and adverse reactions. Thirty-seven volunteers participated in the study, 19 in the BP group and 18 in the PCMX + SA group. The patients applied the medication twice daily to the entire face. Clinical evaluation and lesion counts were obtained at 0, 3, 6, 9 and 12 weeks. At week 12 both groups showed a marked improvement in both inflammatory and noninflammatory lesions (60% and 54% for the BP group and 62% and 56% for and 56% for the PCMX + SA group, respectively). Although PCMX + SA showed a slightly stronger keratolytic effect throughout the study period, there was no statistically significant difference in the reduction of the papulopustules or comedones between the two groups. Adverse effects such as erythema and photosensitivity were significantly fewer in the PCMX + SA group at week 12 (p = 0.0002 and p = 0.05, respectively). These results suggest that PCMX + SA cream is as effective as BP gel in the treatment of papulopustular and comedonal acne and that it is better tolerated.

  9. Synthesis, theoretical calculation, electrochemistry and total antioxidant capacity of 5-benzoyl-6-phenyl-4-(4-methoxyphenyl)-1,2,3,4-tetrahydro-2-thioxopyrimidine and derivatives

    NASA Astrophysics Data System (ADS)

    Ergan, Erdem; Akbas, Esvet; Levent, Abdulkadir; Sahin, Ertan; Konus, Metin; Seferoglu, Nurgul

    2017-05-01

    5-Benzoyl-6-phenyl-4-(4-mehtoxyphenyl)-1,2,3,4-tetrahydro-2-thioxopyrimidine (1) have been prepared via Biginelli cyclocondensation reaction in acetic acid under reflux condition in good yield. The structure of 1 was determined by using spectroscopic techniques like 1H/13C NMR and elemental analyses. And also their molecular characterizations of compounds were analyzed by X-ray crystal analysis. A series of novel pyrimidine derivatives were obtained by reaction compound 1 with various reactive. All synthesized pyrimidine derivatives and related keto and enol tautomeric forms have been optimized geometrically with DFT in Gaussian at the B3LYP/6-31 + G (d, p) level in order to obtain information about the 3D geometries and electronic structures. The results showed that the keto tautomer is more stable than enol tautomer. However, the non-linear optical (NLO) properties were evaluated theoretically. The electrochemical properties of the novel compounds were investigated by CV and DPV. In addition, the total antioxidant capacities of all new synthesized compounds were measured in vitro by ABTS assay.

  10. Synthesis, biological evaluation, and structure-activity relationships of N-benzoyl-2-hydroxybenzamides as agents active against P. falciparum (K1 strain), Trypanosomes, and Leishmania.

    PubMed

    Stec, Jozef; Huang, Qingqing; Pieroni, Marco; Kaiser, Marcel; Fomovska, Alina; Mui, Ernest; Witola, William H; Bettis, Samuel; McLeod, Rima; Brun, Reto; Kozikowski, Alan P

    2012-04-12

    In our efforts to identify novel chemical scaffolds for the development of new antiprotozoal drugs, a compound library was screened against Toxoplasma gondii tachyzoites with activity discovered for N-(4-ethylbenzoyl)-2-hydroxybenzamide 1a against T. gondii as described elsewhere. Synthesis of a compound set was guided by T. gondii SAR with 1r found to be superior for T. gondii , also active against Thai and Sierra Leone strains of Plasmodium falciparum , and with superior ADMET properties as described elsewhere. Herein, synthesis methods and details of the chemical analysis of the compounds in this series are described. Further, this series of N-benzoyl-2-hydroxybenzamides was repurposed for testing against four other protozoan parasites: Trypanosoma brucei rhodesiense , Trypanosoma cruzi , Leishmania donovani , and P. falciparum (K1 isolate). Structure-activity analyses led to the identification of compounds in this set with excellent antileishmanial activity (compound 1d). Overall, compound 1r was the best and had activity 21-fold superior to that of the standard antimalarial drug chloroquine against the K1 P. falciparum isolate.

  11. Anti-UVC Irradiation and Metal Chelation Properties of 6-Benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: An Implications for Anti-Cataract Agent

    PubMed Central

    Liao, Jiahn-Haur; Wu, Tzu-Hua; Hsu, Feng-Lin; Huang, Yi-Shiang; Chiang, Po-Hung; Huang, Zih-You; Huang, Chi-Hsien; Wu, Shih-Hsiung; Lin, Mei-Hsiang

    2011-01-01

    Coumarin derivative 1, 5,7-dihydroxy-6-(3-methyl-1-butyryl)-4-phenyl-chromen- 2-one, has been reported to possess radical scavenging activity and DNA protection. We have synthesized a series of coumarins with structural modifications at positions C4, C5, C6 and C7 and evaluated them for their anti-UVC properties. Coumarin 7, 6-benzoyl-5,6-dihydroxy-4-phenyl-chromen-2-one, was found to have the most potent activity in protecting porcine γ-crystallin against UVC insults. Results of fluorescence assays indicated that compound 7 was capable of decreasing the loss of intensity while lens crystallins and DNA PUC19 were irradiated with UVC. Presence of compound 7 decreased hydroxyl radical levels determined by probe 1b and the free iron concentrations determined by Ferrozine reagent. The chelation assay showed that compound 7 was chelated to metal via 6-CO and 5-OH on the benzopyrone ring. The observed protective effects of compound 7 towards crystallins from insults of UVC and free radicals may be due to its iron-chelating activity and its peak absorption at 254 nm. PMID:22072936

  12. Benzoyl Peroxide Formulated Polycarbophil/Carbopol 934P Hydrogel with Selective Antimicrobial Activity, Potentially Beneficial for Treatment and Prevention of Bacterial Vaginosis

    PubMed Central

    Cavera, Veronica L.; Rogers, Michael A.; Huang, Qingrong; Zubovskiy, Konstantin; Chikindas, Michael L.

    2013-01-01

    The human vagina is colonized by a variety of indigenous microflora; in healthy individuals the predominant bacterial genus is Lactobacillus while those with bacterial vaginosis (BV) carry a variety of anaerobic representatives of the phylum Actinobacteria. In this study, we evaluated the antimicrobial activity of benzoyl peroxide (BPO) encapsulated in a hydrogel against Gardnerella vaginalis, one of the causative agents of BV, as well as indicating its safety for healthy human lactobacilli. Herein, it is shown that in well diffusion assays G. vaginalis is inhibited at 0.01% hydrogel-encapsulated BPO and that the tested Lactobacillus spp. can tolerate concentrations of BPO up to 2.5%. In direct contact assays (cells grown in a liquid culture containing hydrogel with 1% BPO or BPO particles), we demonstrated that hydrogels loaded with 1% BPO caused 6-log reduction of G. vaginalis. Conversely, three of the tested Lactobacillus spp. were not inhibited while L. acidophilus growth was slightly delayed. The rheological properties of the hydrogel formulation were probed using oscillation frequency sweep, oscillation shear stress sweep, and shear rate sweep. This shows the gel to be suitable for vaginal application and that the encapsulation of BPO did not alter rheological properties. PMID:24382940

  13. Benzoyl peroxide formulated polycarbophil/carbopol 934P hydrogel with selective antimicrobial activity, potentially beneficial for treatment and prevention of bacterial vaginosis.

    PubMed

    Xu, Shiqi; Cavera, Veronica L; Rogers, Michael A; Huang, Qingrong; Zubovskiy, Konstantin; Chikindas, Michael L

    2013-01-01

    The human vagina is colonized by a variety of indigenous microflora; in healthy individuals the predominant bacterial genus is Lactobacillus while those with bacterial vaginosis (BV) carry a variety of anaerobic representatives of the phylum Actinobacteria. In this study, we evaluated the antimicrobial activity of benzoyl peroxide (BPO) encapsulated in a hydrogel against Gardnerella vaginalis, one of the causative agents of BV, as well as indicating its safety for healthy human lactobacilli. Herein, it is shown that in well diffusion assays G. vaginalis is inhibited at 0.01% hydrogel-encapsulated BPO and that the tested Lactobacillus spp. can tolerate concentrations of BPO up to 2.5%. In direct contact assays (cells grown in a liquid culture containing hydrogel with 1% BPO or BPO particles), we demonstrated that hydrogels loaded with 1% BPO caused 6-log reduction of G. vaginalis. Conversely, three of the tested Lactobacillus spp. were not inhibited while L. acidophilus growth was slightly delayed. The rheological properties of the hydrogel formulation were probed using oscillation frequency sweep, oscillation shear stress sweep, and shear rate sweep. This shows the gel to be suitable for vaginal application and that the encapsulation of BPO did not alter rheological properties.

  14. Determination of rhenium content in molybdenite by ICP-MS after separation of the major matrix by solvent extraction with N-benzoyl-N-phenylhydroxalamine.

    PubMed

    Li, Jie; Zhong, Li-feng; Tu, Xiang-lin; Liang, Xi-rong; Xu, Ji-feng

    2010-05-15

    A simple and rapid analytical method for determining the concentration of rhenium in molybdenite for Re-Os dating was developed. The method used isotope dilution-inductively coupled plasma-mass spectrometry (ID-ICP-MS) after the removal of major matrix elements (e.g., Mo, Fe, and W) from Re by solvent extraction with N-benzoyl-N-phenylhydroxylamine (BPHA) in chloroform solution. The effect on extraction efficiency of parameters such as pH (HCl concentration), BPHA concentration, and extraction time were also assessed. Under the optimal experimental conditions, the validity of the separation method was accessed by measuring (187)Re/(185)Re values for a molybdenite reference material (JDC). The obtained values were in good agreement with previously measured values of the Re standard. The proposed method was applied to replicate Re-Os dating of JDC and seven samples of molybdenite from the Yuanzhuding large Cu-Mo porphyry deposit. The results demonstrate good precision and accuracy for the proposed method. The advantages of the method (i.e., simplicity, efficiency, short analysis time, and low cost) make it suitable for routine analysis.

  15. Synthesis, spectroscopic and structural characterization of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine with theoretical calculations using density functional theory

    NASA Astrophysics Data System (ADS)

    İnkaya, Ersin; Dinçer, Muharrem; Şahan, Emine; Yıldırım, İsmail

    2013-10-01

    In this paper, we will report a combined experimental and theoretical investigation of the molecular structure and spectroscopic parameters (FT-IR, 1H NMR, 13C NMR) of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine. The compound crystallizes in the triclinic space group P-1 with Z = 2. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping electron density isosurface with electrostatic potential (ESP). Also, non-linear optical properties of the title compound were performed at B3LYP/6-311++G(d,p) level. The theoretical results showed an excellent agreement with the experimental values.

  16. Synthesis, spectroscopic and structural characterization of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine with theoretical calculations using density functional theory.

    PubMed

    Inkaya, Ersin; Dinçer, Muharrem; Sahan, Emine; Yıldırım, Ismail

    2013-10-01

    In this paper, we will report a combined experimental and theoretical investigation of the molecular structure and spectroscopic parameters (FT-IR, (1)H NMR, (13)C NMR) of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine. The compound crystallizes in the triclinic space group P-1 with Z=2. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping electron density isosurface with electrostatic potential (ESP). Also, non-linear optical properties of the title compound were performed at B3LYP/6-311++G(d,p) level. The theoretical results showed an excellent agreement with the experimental values.

  17. Quantitative determination of methylphenidate in plasma by gas chromatography negative ion chemical ionisation mass spectrometry using o-(pentafluorobenzyloxycarbonyl)-benzoyl derivatives.

    PubMed

    Leis, Hans J; Schütz, Helmut; Windischhofer, Werner

    2011-06-01

    The use of a novel electrophoric derivatisation reagent, o-(pentafluorobenzyloxycarbonyl)-benzoyl chloride, for the quantitative determination of methylphenidate in plasma is described. The drug can be quantitatively measured down to 72 pg/mL plasma using only 250 μL of sample due to the extraordinary sensitivity of the derivatives under negative ion chemical ionisation mass spectrometry. Plasma samples were made alkaline with carbonate buffer and treated with extraction solvent n-hexane and reagent solution for 30 min, which, after concentration, was measured by GC-NICI-MS. The method is rapid as extraction and derivatisation occur in one single step. A stable isotope-labelled internal standard was used and its synthesis described. Full validation data are given to demonstrate the usefulness of the assay, including specificity, linearity, accuracy and precision, long-term stability, short-term stability, freeze-thaw stability, stock solution stability, autosampler stability, aliquot analysis, robustness, matrix effect, and prospective analytical batch size accuracy. The method has been successfully applied to pharmacokinetic profiling of the drug after oral application.

  18. Synthesis, spectral characterization, thermal behaviour, antibacterial activity and DFT calculation on N‧-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide and N‧-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester

    NASA Astrophysics Data System (ADS)

    Bharty, M. K.; Dani, R. K.; Kushawaha, S. K.; Prakash, Om; Singh, Ranjan K.; Sharma, V. K.; Kharwar, R. N.; Singh, N. K.

    2015-06-01

    Two new compounds N‧-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N‧-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized and characterized with the aid of elemental analyses, IR, NMR and single crystal X-ray diffraction data. Compounds 1 and 2 crystallize in orthorhombic and monoclinic systems with space group Pna21 and P21/n, respectively. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH⋯π and NH⋯π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. Compounds 1 and 2 are thermally stable and show NLO behaviour better than the urea crystal.

  19. Crystal structures and theoretical calculations of two peculiar compounds derived from 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one

    NASA Astrophysics Data System (ADS)

    Yan, Xingchen; Wu, Xiaojing; Xu, Jiakun; Fan, Yuhua; Bi, Caifeng; Zhang, Xia; Zhang, Zhongyu

    2014-09-01

    A potassium coordination polymer [K2(PMBP)2(H2O)3]n·2nH2O (1) was prepared by reaction of 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one (HPMBP) with potassium hydroxide. The single crystal of the supermolecule C6H11NH3+·PMBP- (2) was then obtained by utilizing cyclohexylamine as the proton acceptor. It is a diketonate salt with an organic base where the PMBP- anions are stabilized by the intermolecular weak interactions (including hydrogen bonding, π-π stacking interactions and Van der Waals forces), rather than by coordination to a metal centre. Geometrical parameters of the isolated PMBP- anion were optimized through quantum chemistry calculation to simulate the state without any disturbances or interactions. Comparison of geometric parameters of compound 1 with the optimized structure of PMBP- provides an approach to study weak intermolecular interactions in the crystal state. The coordination sites and the proton acceptors of hydrogen bonds predicted by theoretical calculations are consistent to the experimental results.

  20. Crystal structure of 4-(2-azido-phen-yl)-5-benzoyl-2-(1H-indol-3-yl)-1H-pyrrole-3-carbo-nitrile.

    PubMed

    Vimala, G; Raja, J Kamal; Naaz, Y Amina; Preumal, P T; SubbiahPandi, A

    2015-05-01

    In the title compound, C26H16N6O, the dihedral angles between the central pyrrole ring and the pendant indole ring system (r.m.s. deviation = 0.027 Å) and the azide-bearing benzene ring are 37.56 (8) and 51.62 (11)°, respectively. The azide group is almost coplanar with its attached benzene ring [C-C-N-N = 3.8 (3)°]. The benzoyl benzene ring is disordered over two orientations twisted with respect to each other by 9.29 (8)° in a 0.514 (2):0.486 (2) ratio. In the crystal, inversion dimers linked by pairs of Np-H⋯O (p = pyrrole) hydrogen bonds generate R 2 (2)(10) loops. A second inversion dimer arises from a pair of Ni-H⋯Nc (i = indole and c = cyanide) hydrogen bonds, which generates an R 2 (2)(16) loop. Together, the hydrogen bonds lead to [011] chains in the crystal.

  1. Combination of benzoyl peroxide 5% gel with liquid cleanser and moisturizer SPF 30 in acne treatment results in high levels of subject satisfaction, good adherence and favorable tolerability.

    PubMed

    Kim, Mi-Ran; Kerrouche, Nabil

    2017-07-05

    Skin care products (cleansers and moisturizers) to complement benzoyl peroxide (BPO) in the treatment of acne may improve treatment tolerability and adherence. Evaluate subject satisfaction after use of BPO 5% gel in combination with liquid cleanser and moisturizer SPF 30. Open-label study including subjects aged ≥12 years with mild-to-moderate facial acne; ClinicalTrials.gov Identifier: NCT02589405. Once daily BPO 5% gel, twice daily liquid cleanser and once daily moisturizer SPF 30 were applied for 12 weeks. Assessments included a subject satisfaction questionnaire, investigator global assessment of improvement, lesion counts, the presence of Propionibacterium acnes, and safety. Fifty subjects were enrolled. Most subjects were overall satisfied with the three-part regimen (87%) and felt better about themselves (94%). Subjects indicated the skin care products helped prepare the skin for treatment (85%), relieve itchy skin (81%) and reduce irritation (87%). Most subjects considered that the liquid cleanser (80%) and moisturizer SPF 30 (84%) were a necessary part of acne treatment. BPO reduced P. acnes load by 89% at week 1. The treatment was well tolerated. The combination of BPO 5% gel with liquid cleanser and moisturizer SPF 30 resulted in high levels of subject satisfaction, good tolerability and treatment adherence.

  2. Anti-UVC irradiation and metal chelation properties of 6-benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: an implications for anti-cataract agent.

    PubMed

    Liao, Jiahn-Haur; Wu, Tzu-Hua; Hsu, Feng-Lin; Huang, Yi-Shiang; Chiang, Po-Hung; Huang, Zih-You; Huang, Chi-Hsien; Wu, Shih-Hsiung; Lin, Mei-Hsiang

    2011-01-01

    Coumarin derivative 1, 5,7-dihydroxy-6-(3-methyl-1-butyryl)-4-phenyl-chromen- 2-one, has been reported to possess radical scavenging activity and DNA protection. We have synthesized a series of coumarins with structural modifications at positions C4, C5, C6 and C7 and evaluated them for their anti-UVC properties. Coumarin 7, 6-benzoyl-5,6-dihydroxy-4-phenyl-chromen-2-one, was found to have the most potent activity in protecting porcine γ-crystallin against UVC insults. Results of fluorescence assays indicated that compound 7 was capable of decreasing the loss of intensity while lens crystallins and DNA PUC19 were irradiated with UVC. Presence of compound 7 decreased hydroxyl radical levels determined by probe 1b and the free iron concentrations determined by Ferrozine reagent. The chelation assay showed that compound 7 was chelated to metal via 6-CO and 5-OH on the benzopyrone ring. The observed protective effects of compound 7 towards crystallins from insults of UVC and free radicals may be due to its iron-chelating activity and its peak absorption at 254 nm.

  3. Enhanced solubility and antibacterial activity of lipophilic fluoro-substituted N-benzoyl-2-aminobenzothiazoles by complexation with β-cyclodextrins.

    PubMed

    Trapani, A; De Laurentis, N; Armenise, D; Carrieri, A; Defrenza, I; Rosato, A; Mandracchia, D; Tripodo, G; Salomone, A; Capriati, V; Franchini, C; Corbo, F

    2016-01-30

    Some lipophilic fluoro-substituted N-benzoyl-2-aminobenzothiazole antibacterial agents have been evaluated for their activity in the presence of cyclodextrins (CDs) containing aqueous solutions where CDs are adopted as solubilizing excipients for improving the poor water solubility of these compounds. For such purpose both the natural β-CD and one of FDA/EMA approved CDs for parenteral use (i.e. HP-β-CD) have been employed. The solubility rank order observed was accounted for by thermal analysis (Differential Scanning Calorimetry) and FT-IR spectroscopy. The most promising compound was subjected to further NMR spectroscopic studies and molecular modelling simulations to verify the interactions between the guest molecule and the CD cavity. The assessment of the antibacterial activity of such compounds against selected Gram positive and Gram negative bacterial strains clearly showed that their antimicrobial effectiveness may, quite in all instances, be positively affected by complexation with β-CD and HP-β-CD. These results, which are in some ways in contrast with those already reported in the literature, are herein discussed on the basis of plausible mechanisms. Moreover, this investigation also reveals that the described methodology of complexing both lipophilic and hydrophilic antimicrobial agents with CDs may be an useful approach to enhance their effectiveness as well as a promising strategy to overcome even the microbial resistance problem. Copyright © 2015 Elsevier B.V. All rights reserved.

  4. Solid phase extraction of mercury on sulfur loaded with N-(2-chloro benzoyl)-N'-phenylthiourea as a new adsorbent and determination by cold vapor atomic absorption spectrometry.

    PubMed

    Pourreza, N; Parham, H; Kiasat, A R; Ghanemi, K; Abdollahi, N

    2009-06-15

    This paper reports sulfur powder loaded with N-(2-chloro benzoyl)-N'-phenylthiourea as a new solid phase extractor for determination of ultra trace amounts of mercury. The mercury ions were retained on a mini-column filled with the solid phase at a flow rate of 16 mL min(-1). The retained Hg(II) ions were eluted with 3 mol L(-1) solution of HCl and measured by cold vapor atomic absorption spectrometry (CV-AAS). The mercury vapors were generated by a homemade Reaction Cell-Gas Liquid Separator (RC-GLS). The effect of different variables such as pH, sample flow rate, amounts of ligand loaded on sulfur and SnCl2 concentration was investigated. Calibration curve was linear in the range of 0.02-1.20 microg L(-1) with r=0.9991 (n=8). The limit of detection (LOD) based on three times the standard deviation of the blank was 0.012 and 0.003 microg L(-1) when 250 and 1000 mL sample volumes were used, respectively. The relative standard deviation (R.S.D.) for determination of 0.04 and 1.00 microg L(-1) of Hg(II) was 3.9 and 1.2% (n=8), respectively. The method was successfully applied to determine Hg(II) in water and marine samples.

  5. Design, Synthesis and Biological Evaluation of N4-Sulfonamido-Succinamic, Phthalamic, Acrylic and Benzoyl Acetic Acid Derivatives as Potential DPP IV Inhibitors

    PubMed Central

    Khalaf, Reema Abu; Sheikha, Ghassan Abu; Al-Sha'er, Mahmoud; Taha, Mutasem

    2013-01-01

    As incidence rate of type II diabetes mellitus continues to rise, there is a growing need to identify novel therapeutic agents with improved efficacy and reduced side effects. Dipeptidyl peptidase IV (DPP IV) is a multifunctional protein involved in many physiological processes. It deactivates the natural hypoglycemic incretin hormone effect. Inhibition of this enzyme increases endogenous incretin level, incretin activity and should restore glucose homeostasis in type II diabetic patients making it an attractive target for the development of new antidiabetic drugs. One of the interesting reported anti- DPP IV hits is Gemifloxacin which is used as a lead compound for the development of new DPP IV inhibitors. In the current work, design and synthesis of a series of N4-sulfonamido-succinamic, phthalamic, acrylic and benzoyl acetic acid derivatives was carried out. The synthesized compounds were evaluated for their in vitro anti-DPP IV activity. Some of them have shown reasonable bioactivity, where the most active one 17 was found to have an IC50 of 33.5 μM. PMID:24358058

  6. Synthesis, spectral characterization, thermal behaviour, antibacterial activity and DFT calculation on N'-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide and N'-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester.

    PubMed

    Bharty, M K; Dani, R K; Kushawaha, S K; Prakash, Om; Singh, Ranjan K; Sharma, V K; Kharwar, R N; Singh, N K

    2015-06-15

    Two new compounds N'-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N'-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized and characterized with the aid of elemental analyses, IR, NMR and single crystal X-ray diffraction data. Compounds 1 and 2 crystallize in orthorhombic and monoclinic systems with space group Pna21 and P21/n, respectively. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH⋯π and NH⋯π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. Compounds 1 and 2 are thermally stable and show NLO behaviour better than the urea crystal. Copyright © 2015 Elsevier B.V. All rights reserved.

  7. A double-blind, randomized, bilateral comparison of skin irritancy following application of the combination acne products clindamycin/tretinoin and benzoyl peroxide/adapalene.

    PubMed

    Goreshi, Renato; Samrao, Aman; Ehst, Benjamin D

    2012-12-01

    The use of topical medications for acne vulgaris is often limited by their irritant properties. Newer combination preparations are available and offer convenience, but irritant potential may still be a hindrance, perhaps more so with the combination of 2 agents. Few studies have compared these formulations directly for tolerability. We sought to compare the tolerability of 2 combination topical acne products, clindamycin 1.2%-tretinoin 0.025% (CLIN/RA) gel and benzoyl peroxide 2.5%-adapalene 0.1% (BPO/ADA) gel. CLIN/RA and BPO/ADA were applied daily to opposite sides of a subject's face for 21 days in a double-blinded fashion. Investigators' Global Assessments and study subject self-assessments of burning/stinging, itching, erythema, and dryness/scaling were collected. Transepidermal water loss (TEWL) was also measured as an objective measure of skin irritation. A mixed model analysis and repeated-measures analysis of variance were used to compare outcomes for both acne formulations. CLIN/RA produced significantly less burning/stinging than BPO/ADA (P<.001) as well as significantly less pruritus than BPO/ ADA (P<.001). BPO/ADA caused significantly more TEWL than CLIN/RA (P=.005). There was no significant difference in the amount of erythema or the amount of dryness/scaling caused by either formulation. CLIN/RA produced significantly less skin irritancy and TEWL than BPO/ADA.

  8. Treatment of 2,453 acne vulgaris patients aged 12-17 years with the fixed-dose adapalene-benzoyl peroxide combination topical gel: efficacy and safety.

    PubMed

    Eichenfield, Lawrence E; Jorizzo, Joseph L; Dirschka, Thomas; Taub, Amy Forman; Lynde, Charles; Graeber, Michael; Kerrouche, Nabil

    2010-11-01

    Acne vulgaris is a common disease in adolescents, and early treatment may minimize its physical and psychological effects. A fixed-dose combination gel of adapalene 0.1% and benzoyl peroxide 2.5% (adapalene-BPO) is efficacious and safe in the treatment of acne patients aged 12 years or older, as demonstrated in three randomized and controlled studies. The current study is a subgroup analysis of the efficacy and safety of adapalene-BPO among 2,453 patients aged 12-17 years. After 12 weeks of treatment, significantly more patients in the adapalene-BPO group were "clear" or "almost clear" (30.9%, P < 0.001) compared to the monotherapies and vehicle. The percentage reduction from baseline in total, inflammatory and non-inflammatory lesions was 56, 63 and 54.5 percent in the adapalene-BPO group, respectively, significantly higher than in the monotherapy groups and vehicle (all P < 0.001). Significantly earlier onset of effect was observed at week 1. Adapalene-BPO was also well tolerated, with the mean scores of dryness, erythema, scaling and stinging/burning less than 1 (mild) at all study visits. Overall, the adapalene-BPO combination gel provides significantly greater and synergistic efficacy and a fast onset of action compared to the monotherapies and vehicle in young acne patients aged 12-17 years.

  9. Adapalene-benzoyl peroxide, a fixed-dose combination for the treatment of acne vulgaris: results of a multicenter, randomized double-blind, controlled study.

    PubMed

    Thiboutot, Diane M; Weiss, Jonathan; Bucko, Alicia; Eichenfield, Lawrence; Jones, Terry; Clark, Scott; Liu, Yin; Graeber, Michael; Kang, Sewon

    2007-11-01

    A fixed-dose combination gel with adapalene 0.1% and benzoyl peroxide (BPO) 2.5% has been developed for the once-daily treatment of acne. To evaluate the efficacy and safety of adapalene 0.1% -BPO 2.5% fixed combination gel (adapalene-BPO) for the treatment of acne. A total of 517 subjects were randomized in a double-blind controlled trial to receive either adapalene-BPO, adapalene, BPO, or vehicle for 12 weeks (2:2:2:1 randomization). Evaluation included success rate (subjects "clear" or "almost clear"), lesion count, cutaneous tolerability, and adverse events. The fixed-dose combination gel of adapalene and BPO was significantly more effective than corresponding monotherapies, with significant differences in total lesion counts observed as early as 1 week. Adverse event frequency and cutaneous tolerability profile for adapalene-BPO were similar to adapalene monotherapy. These data were generated in a controlled trial. Results obtained in clinical practice could differ. The fixed-dose combination of adapalene and BPO provides significantly greater efficacy for the treatment of acne vulgaris as early as week 1 relative to monotherapies, with a comparable safety profile to adapalene.

  10. Pilot randomized-control trial to assess the effect product sampling has on adherence using adapalene/benzoyl peroxide gel in acne patients.

    PubMed

    Sandoval, Laura F; Semble, Ashley; Gustafson, Cheryl J; Huang, Karen E; Levender, Michelle M; Feldman, Steven R

    2014-02-01

    The treatment of acne can be difficult, with suboptimal adherence resulting in poor treatment outcomes. To determine whether demonstrating to patients how to properly apply a topical acne medication through the use of a sample product will improve adherence. Subjects with mild to moderate acne were instructed to use adapalene/benzoyl peroxide gel once daily for six weeks. Subjects were randomized into sample or no sample group. Sample group received a demonstration on how to apply the medication using a product sample. The primary outcome was median adherence, recorded using electronic monitoring, and secondary outcomes were efficacy measures including the Acne Global Assessment (AGA) and lesion counts and the Perceived Medical Condition Self-Management Scale (PMCSMS). Data from 17 patients was collected and analyzed. Median adherence rates were 50% in the sample group and 35% in the no sample group (p=0.67). The median percent improvement in non-inflammatory lesions were 46% for the sample group and 33% for the no-sample group (p=0.10). The small size of this pilot study limited the extent of subgroup analyses. Objective electronic monitoring expanded our previous observations of poor adherence in the treatment of acne. There is a considerable potential effect size on adherence for the use of samples, supporting the need for future, well powered studies to assess the value of using samples in the treatment of acne and other dermatologic skin diseases.

  11. Evaluation of the efficacy, tolerability, and safety of an over-the-counter acne regimen containing benzoyl peroxide and salicylic acid in subjects with acne.

    PubMed

    Kircik, Leon H; Gwazdauskas, Jennifer; Butners, Victoria; Eastern, Joseph; Green, Lawrence J

    2013-03-01

    Benzoyl peroxide (BPO) is a widely used over-the-counter (OTC) topical acne treatment often used in combination with salicylic acid (SA) to achieve better comedone control than that achieved with BPO alone. MaxClarity™ is an OTC acne treatment system comprising BPO and SA in an aqueous foam delivery vehicle, VersaFoam AF™. This paper describes 2 open-label, single-arm studies conducted to assess the efficacy, safety, tolerability, and patient preference of MaxClarity in the treatment of mild, moderate, and severe acne. Subjects applied MaxClarity twice daily for 8 weeks in study 402 and for 12 weeks in study 405. Reductions in all lesion types were seen throughout both studies. At week 8 (study 402), there was a mean reduction from baseline of -56.9 ± 32.7% in total lesions in subjects with mild, moderate, or severe acne. At week 12 (study 405), there was a reduction from baseline of -61.6 ± 22.0% in total lesions in subjects with moderate or severe acne. Overall, both studies demonstrated that MaxClarity is a generally well tolerated and effective treatment for mild, moderate, and severe acne.

  12. Recent advances in the use of adapalene 0.1%/benzoyl peroxide 2.5% to treat patients with moderate to severe acne.

    PubMed

    Leyden, James

    2016-01-01

    The central role of inflammation in acne is now more clearly understood. Adapalene, a third-generation topical retinoid, down-regulates toll-like receptor 2 expression and inhibits activator protein-1 activity. In a fixed-dose combination, adapalene and benzoyl peroxide (BPO) act synergistically on inflammatory patterns through regulation of innate immunity. In addition to reducing inflammatory and non-inflammatory lesions, adapalene/BPO helps prevent lesion and microcomedone formation. The combination of a topical retinoid and antimicrobial agent remains the preferred approach for almost all patients with acne. In cases of more severe disease, there is a clinical benefit in combining adapalene/BPO with an oral antibiotic for 12 weeks. Most recently, adapalene/BPO plus doxycycline 200 mg was found to be highly effective when compared with isotretinoin in the treatment of patients with severe acne with nodules. Long-term maintenance therapy is needed for most patients. Retinoids are the preferred agents, with BPO added in patients with more severe disease if needed. Adapalene is anticomedogenic, reduces comedones and has anti-inflammatory properties, while BPO is a unique antimicrobial agent not shown to induce microbial resistance after more than 50 years of use. Maintenance therapy for 6 months with adapalene/BPO prevents relapse among patients with severe acne and continues to reduce disease symptoms.

  13. Investigation of the formation of benzoyl peroxide, benzoic anhydride, and other potential aerosol products from gas-phase reactions of benzoylperoxy radicals

    NASA Astrophysics Data System (ADS)

    Strollo, Christen M.; Ziemann, Paul J.

    2016-04-01

    The secondary organic aerosol (SOA) products of the reaction of benzaldehyde with Cl atoms and with OH radicals in air in the absence of NOx were investigated in an environmental chamber in order to better understand the possible role of organic peroxy radical self-reactions in SOA formation. SOA products and authentic standards were analyzed using mass spectrometry and liquid chromatography, and results show that the yields of benzoyl peroxide (C6H5C(O)OO(O)CC6H5) and benzoic anhydride (C6H5C(O)O(O)CC6H5), two potential products from the gas-phase self-reaction of benzoylperoxy radicals (C6H5C(O)OO·), were less than 0.1%. This is in contrast to results of recent studies that have shown that the gas-phase self-reactions of β-nitrooxyperoxy radicals formed from reactions of isoprene with NO3 radicals form dialkyl peroxides that contribute significantly to gas-phase and SOA products. Such reactions have also been proposed to explain the gas-phase formation of extremely low volatility dimers from autooxidation of terpenes. The results obtained here indicate that, at least for benzoylperoxy radicals, the self-reactions form only benzoyloxy radicals. Analyses of SOA composition and volatility were inconclusive, but it appears that the SOA may consist primarily of oligomers formed through heterogeneous/multiphase reactions possibly involving some combination of phenol, benzaldehyde, benzoic acid, and peroxybenzoic acid.

  14. Topical alpha-tocotrienol supplementation inhibits lipid peroxidation but fails to mitigate increased transepidermal water loss after benzoyl peroxide treatment of human skin.

    PubMed

    Weber, Stefan U; Thiele, Jens J; Han, Nancy; Luu, Chate; Valacchi, Giuseppe; Weber, Stefanie; Packer, Lester

    2003-01-15

    Benzoyl peroxide (BPO) is a commonly used drug in the treatment of acne vulgaris, but it induces unwanted side effects related to stratum corneum (SC) function. Since it has been recently shown to oxidize SC antioxidants, it was hypothesized that antioxidant supplementation may mitigate the BPO-induced SC changes. To test this, 11 subjects were selected to be topically supplemented with alpha-tocotrienol (5% w/vol) for 7 d on defined regions of the upper back, while the contralateral region was used for vehicle-only controls. Starting on day 8, all test sites were also treated with BPO (10%) for 7 d; the alpha-tocotrienol supplementation was continued throughout the study. A single dose of BPO depleted 93.2% of the total vitamin E. While continuing the BPO exposure for 7 d further depleted vitamin E in both vehicle-only and alpha-tocotrienol-treated sites, significantly more vitamin E remained in the alpha-tocotrienol-treated areas. Seven BPO applications increased lipid peroxidation. Alpha-tocotrienol supplementation significantly mitigated the BPO-induced lipid peroxidation. The transepidermal water loss was increased 1.9-fold by seven BPO applications, while there was no difference between alpha-tocotrienol treatment and controls. The data suggest that alpha-tocotrienol supplementation counteracts the lipid peroxidation but not the barrier perturbation in the SC induced by 10% BPO.

  15. Diverse Cd(II) compounds based on N-benzoyl-L-glutamic acid and N-donor ligands: Structures and photoluminescent properties

    SciTech Connect

    Ma, Ning; Guo, Wei-Ying; Song, Hui-Hua Yu, Hai-Tao

    2016-01-15

    Five new Cd(II) coordination polymers with N-benzoyl-L-glutamic acid (H{sub 2}bzgluO) and different N-donor ligands, [Cd(bzgluO)(2,2′-bipy)(H{sub 2}O)]{sub n} (1), [Cd(bzgluO)(2,4′-bipy){sub 2}(H{sub 2}O)·3H{sub 2}O]{sub n} (2), [Cd(bzgluO)(phen)·H{sub 2}O]{sub n} (3), [Cd(bzgluO)(4,4′-bipy)(H{sub 2}O)]{sub n} (4), [Cd(bzgluO)(bpp)(H{sub 2}O)·2H{sub 2}O]{sub n} (5) were synthesized (2,2′-bipy=2,2′-bipyridine, 2,4′-bipy=2,4′-bipyridine, phen=1,10-phenanthroline, 4,4′-bipy=4,4′-bipyridine, bpp=1,3-di(4-pyridyl)propane). Compounds 1–2 exhibit a 1D single-chain structure. Compound 1 generates a 2D supramolecular structure via π–π stacking and hydrogen bonding, 3D architecture of compound 2 is formed by hydrogen bonding. Compound 3 features a 1D double-chain structure, which are linked by π–π interactions into a 2D supramolecular layer. Compounds 4-5 display a 2D network structure. Neighboring layers of 4 are extended into a 3D supramolecular architecture through hydrogen bonding. The structural diversity of these compounds is attributed to the effect of ancillary N-donor ligands and coordination modes of H{sub 2}bzgluO. Luminescent properties of 1–5 were studied at room temperature. Circular dichroism of compounds 1, 2 and 5 were investigated. - Graphical abstract: Five new Cd(II) metal coordination compounds with H{sub 2}bzgluO and different N-donor ligands were synthesized and characterized. Compounds 1, 2 and 3 present 1D structures, compounds 4 and 5 display 2D networks. Results indicate that auxiliary ligands and coordination modes of H{sub 2}bzgluO play an important role in governing the formation of final frameworks, and the hydrogen-bonding and π–π stacking interactions contribute the formation of the diverse supramolecular architectures. Furthermore, the different crystal structures influence the emission spectra significantly. - Highlights: • It is rarely reported that complexes prepared with N-benzoyl-L-glutamic acid

  16. The effect of benzoyl peroxide 9.8% emollient foam on reduction of Propionibacterium acnes on the back using a short contact therapy approach.

    PubMed

    Leyden, James J; Del Rosso, James Q

    2012-07-01

    Benzoyl peroxide (BP) exerts its therapeutic effect for acne vulgaris through reduction of Propionibacterium acnes. A 1.0 to 2.0 log reduction in P acnes has been demonstrated primarily on the face with use of "leave-on" BP formulations, but also with some BP cleansers. In addition to use for facial acne vulgaris, cleanser formulations of BP are commonly used for truncal acne vulgaris due to ease of use on a large body-surface area and to avoid bleaching of fabric. To date, evaluation of P acnes reduction on the trunk has not been well studied with BP formulations, especially with the use of recognized and standardized methods to accurately determine P acnes colony counts. A previous study demonstrated that a BP 8% cleanser did not reduce counts of P acnes on the back when subjects were instructed to apply the cleanser in the shower, allow it to dry for 20 seconds on the skin, and then rinse off the cleanser. Evaluation of specified time intervals between application on the back and rinsing with BP formulations would help to better define the necessary skin contact time associated with high reductions of P acnes (>90%), recognizing also the potential roles of BP concentration and vehicle. This 2 week study using quantitative bacteriologic cultures evaluates the effectiveness of BP 9.8% emollient foam in reducing P acnes levels on the back with 2 minutes of skin contact time and compares results with a BP 5.3% "leave-on" emollient foam formulation. Short contact therapy utilizing a 2 minute skin contact time with BP 9.8% emollient foam used once daily over a 2 week duration was highly effective in reducing the quantity of P acnes organisms on the back and provided comparable colony count reduction to "leave on" therapy using BP 5.3% emollient foam.

  17. Site-specific oxidation at GG and GGG sequences in double-stranded DNA by benzoyl peroxide as a tumor promoter.

    PubMed

    Kawanishi, S; Oikawa, S; Murata, M; Tsukitome, H; Saito, I

    1999-12-21

    Benzoyl peroxide (BzPO), a free-radical generator, has tumor-promoting activity. As a method for approaching the mechanism of tumor promoter function, the ability of oxidative DNA damage by BzPO was investigated by using (32)P-labeled DNA fragments obtained from the human p53 tumor suppressor gene and c-Ha-ras-1 protooncogene. BzPO induced piperidine-labile sites at the 5'-site guanine of GG and GGG sequences of double-stranded DNA in the presence of Cu(I), whereas the damage occurred at single guanine residues of single-stranded DNA. Both methional and dimethyl sulfoxide (DMSO) inhibited DNA damage induced by BzPO and Cu(I), but typical hydroxyl radical ((*)OH) scavengers, superoxide dismutase (SOD) and catalase, did not inhibit it. On the other hand, H(2)O(2) induced piperidine-labile sites at cytosine and thymine residues of double-stranded DNA in the presence of Cu(I). Phenylhydrazine, which is known to produce phenyl radicals, induced Cu(I)-dependent damage at thymine residues but not at guanine residues. These results suggest that the BzPO-derived reactive species causing DNA damage is different from (*)OH and phenyl radicals generated from benzoyloxyl radicals. BzPO/Cu(I) induced 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG) formation in double-stranded DNA more effectively than that in single-stranded DNA. Furthermore, we observed that BzPO increased the amount of 8-oxodG in human cultured cells. Consequently, it is concluded that benzoyloxyl radicals generated by the reaction of BzPO with Cu(I) may oxidize the 5'-guanine of GG and GGG sequences in double-stranded DNA to lead to 8-oxodG formation and piperidine-labile guanine lesions, and the damage seems to be relevant to the tumor-promoting activity of BzPO.

  18. Diverse Cd(II) compounds based on N-benzoyl-L-glutamic acid and N-donor ligands: Structures and photoluminescent properties

    NASA Astrophysics Data System (ADS)

    Ma, Ning; Guo, Wei-Ying; Song, Hui-Hua; Yu, Hai-Tao

    2016-01-01

    Five new Cd(II) coordination polymers with N-benzoyl-L-glutamic acid (H2bzgluO) and different N-donor ligands, [Cd(bzgluO)(2,2‧-bipy)(H2O)]n (1), [Cd(bzgluO)(2,4‧-bipy)2(H2O)·3H2O]n (2), [Cd(bzgluO)(phen)·H2O]n (3), [Cd(bzgluO)(4,4‧-bipy)(H2O)]n (4), [Cd(bzgluO)(bpp)(H2O)·2H2O]n (5) were synthesized (2,2‧-bipy=2,2‧-bipyridine, 2,4‧-bipy=2,4‧-bipyridine, phen=1,10-phenanthroline, 4,4‧-bipy=4,4‧-bipyridine, bpp=1,3-di(4-pyridyl)propane). Compounds 1-2 exhibit a 1D single-chain structure. Compound 1 generates a 2D supramolecular structure via π-π stacking and hydrogen bonding, 3D architecture of compound 2 is formed by hydrogen bonding. Compound 3 features a 1D double-chain structure, which are linked by π-π interactions into a 2D supramolecular layer. Compounds 4-5 display a 2D network structure. Neighboring layers of 4 are extended into a 3D supramolecular architecture through hydrogen bonding. The structural diversity of these compounds is attributed to the effect of ancillary N-donor ligands and coordination modes of H2bzgluO. Luminescent properties of 1-5 were studied at room temperature. Circular dichroism of compounds 1, 2 and 5 were investigated.

  19. Dinuclear manganese(II) complexes of hexaazamacrocycles bearing N-benzoylated pendant separated by aromatic spacers: Antibacterial, DNA interaction, cytotoxic and molecular docking studies.

    PubMed

    Arthi, P; Shobana, S; Srinivasan, P; Prabhu, D; Arulvasu, C; Kalilur Rahiman, A

    2015-12-01

    Three new homodinuclear manganese(II) complexes of the type [Mn2L(1-3)(ClO4)(H2O)](ClO4)3 (1-3) have been synthesized via cyclocondensation of terephthalaldehyde with three different benzoylated pendants in the presence of manganese(II) perchlorate and characterized by spectroscopic methods. Cyclic voltammetric investigation of complexes (1-3) depict two quasi-reversible one electron reduction processes in the cathodic potential region (E(1)pc=-0.73 to-0.83 V, E(2)pc=-1.31 to -1.40 V) and two quasi-reversible one electron oxidation processes in the anodic potential region (E(1)pa=1.03 to 1.10 V, E(2)pa=1.69 to 1.77 V). Electronic absorption spectra of the complexes suggested tetrahedral geometry around the central metal ion. The observed low magnetic moment values (μeff, 5.60-5.68 B.M.) of the complexes indicate the presence of an antiferromagnetic spin-exchange interaction between two metal centers, which was also supported by the broad EPR signal. All the compounds were tested for antibacterial activity against Gram (-ve) and Gram (+ve) bacterial strains. The binding studies of complexes with CT-DNA suggested minor-groove mode of interaction. Molecular docking studies were carried out in order to find the binding affinity of complexes with DNA and protein EGFR Kinase. The complexes are stabilized by additional electrostatic and van der Waals interaction with the DNA, and support minor groove mode of binding. The cleavage activity of complexes on pBR322 plasmid DNA displays efficient activity through a mechanistic pathway involving hydroxyl radicals. The cytotoxicity of complexes 2 and 3 have been tested against human liver adenocarcinoma (HepG2) cell line. Nuclear-chromatin cleavage has also been observed with propidium iodide (PI) staining and alkaline single-cell gel electrophoresis (comet assay) techniques.

  20. Selective inhibition of MAO-A activity results in an antidepressant-like action of 2-benzoyl 4-iodoselenophene in mice.

    PubMed

    Velasquez, Daniela; Quines, Caroline; Pistóia, Renan; Zeni, Gilson; Nogueira, Cristina W

    2017-03-01

    Depression is a leading cause of disability worldwide. For this reason, the aim of this study was to investigate the possible antidepressant-like activity of 2-benzoyl-4-iodoselenophene (C17H11IOSe), a selenophene compound, in two well-consolidated behavioral assays for screening antidepressant activity (forced swimming test and tail suspension test) in mice. In order to investigate the mechanism of action of C17H11IOSe, it was investigated the activities of cerebral enzymes: monoamine oxidase MAO A and B and Na(+), K(+) ATPase, and if an inhibitor of serotonin synthesis, p-chlorophenylalanine (pCPA) (100mg/kg) blocks the antidepressant-like effect of C17H11IOSe. Swiss mice received (C17H11IOSe) (5-50mg/kg) or canola oil by the intragastric (i.g.) route before behavioral tests. The results showed that C17H11IOSe at dose range of 5-50mg/kg decreased immobility time in the tail suspension test. In the forced swimming test, C17H11IOSe reduced the immobility time at the doses of 10 and 50mg/kg. C17H11IOSe differently affected the cerebral cortical Na(+), K(+) ATPase; the effects on this enzyme were dependent of the dose tested. At a dose of 10mg/kg, the compound increased Na(+), K(+) ATPase activity, while the activity was inhibited at a dose of 50mg/kg. pCPA blocked the antidepressant-like action of C17H11IOSe in mice. Therefore, C17H11IOSe (5-50mg/kg) selectively inhibited MAO-A activity in cerebral cortices of mice. The modulation of serotonergic system contributed to the antidepressant-like action of C17H11IOSe in mice. Copyright © 2016 Elsevier Inc. All rights reserved.

  1. Synthesis and photoluminescence properties of silver(I) complexes based on N-benzoyl-L-glutamic acid and N-donor ligands with different flexibility

    NASA Astrophysics Data System (ADS)

    Yan, Ming-Jie; Feng, Qi; Song, Hui-Hua

    2016-05-01

    By changing the N-donor ancillary ligand, three novel silver (I) complexes {[Ag(HbzgluO) (4,4‧-bipy)]·H2O}n (1), {[Ag2(HbzgluO)2 (bpe)2]·2H2O}n (2) and {[Ag(HbzgluO)(bpp)]·2H2O}n (3) (H2bzgluO = N-benzoyl-L-glutamic acid, 4,4‧-bipy = 4,4ˊ-bipyridine, bpe = 1,2-di(4-pyridyl)ethane, bpp = 1,3-di(4-pyridyl)propane) were synthesized. Their structures have been determined by single-crystal X-ray diffraction analyses and further characterized by elemental analyses, IR spectra, powder X-ray diffraction (PXRD), and thermogravimetric analyses (TGA). In this study, the N-donor ligands are changed from rigidity (4,4‧-bipy), quasi-flexibility (bpe) to flexibility (bpp), the structures of complexes also change. Complex 1 features a 1D chain structure which is further linked together to construct a 2D supramolecular structure through hydrogen bonds. Complex 2 is a 1D double-chains configuration which eventually forms a 3D supramolecular network via hydrogen bonding interactions. Whereas, complex 3 exhibits a 2D pleated grid structure which is linked by hydrogen bonding interactions into a 3D supramolecular network. The present observations demonstrate that the modulation of coordination polymers with different structures can accomplish by changing the spacer length of N-donor ligands. In addition, the solid-state circular dichroism (CD) spectra indicated that compound 2 exhibited negative cotton effect which originated from the chiral ligands H2bzgluO and the solid-state fluorescence spectra of the three complexes demonstrated the auxiliary ligands have influence on the photoluminescence properties of the complexes.

  2. Combination therapy with adapalene-benzoyl peroxide and oral lymecycline in the treatment of moderate to severe acne vulgaris: a multicentre, randomized, double-blind controlled study.

    PubMed

    Dréno, B; Kaufmann, R; Talarico, S; Torres Lozada, V; Rodríguez-Castellanos, M A; Gómez-Flores, M; De Maubeuge, J; Berg, M; Foley, P; Sysa-Jedrzejowska, A; Kerrouche, N; Paliargues, F; Bettoli, V

    2011-08-01

    Oral antibiotics in association with a topical retinoid with or without benzoyl peroxide (BPO) are the recommended first-line option in the treatment of moderate to severe acne vulgaris. To evaluate the efficacy and safety of oral lymecycline 300 mg with adapalene 0·1%-BPO 2·5% (A/BPO) fixed-dose gel in comparison with oral lymecycline 300 mg with a vehicle gel in subjects with moderate to severe acne vulgaris. A total of 378 subjects were randomized in a double-blind, controlled trial to receive once-daily lymecycline with either A/BPO or vehicle for 12 weeks. Evaluations included percentage changes from baseline in lesion counts, success rate (subjects 'clear' or 'almost clear'), skin tolerability, adverse events and patients' satisfaction. The median percentage reduction from baseline in total lesion counts at week 12 was significantly higher (P < 0·001) in the lymecycline with A/BPO group (-74·1%) than in the lymecycline with vehicle group (-56·8%). The success rate was significantly higher (47·6% vs. 33·7%, P = 0·002) in subjects treated with lymecycline and A/BPO. Both inflammatory and noninflammatory lesions were significantly reduced at week 12 (both P < 0·001) with a rapid onset of action from week 2 for noninflammatory lesions (P < 0·001) and week 4 for inflammatory lesions (P = 0·005). The A/BPO and lymecycline combination was well tolerated. The proportion of satisfied and very satisfied subjects was similar in both groups, but the number in the A/BPO group who were 'very satisfied' was significantly greater (P = 0·031). These results demonstrate the clinical benefit of combining A/BPO with lymecycline in the treatment of moderate to severe acne vulgaris. © 2011 The Authors. BJD © 2011 British Association of Dermatologists 2011.

  3. Effects of Adapalene-Benzoyl Peroxide Combination Gel in Treatment or Maintenance Therapy of Moderate or Severe Acne Vulgaris: A Meta-Analysis

    PubMed Central

    Zhou, Rongying

    2014-01-01

    Background An antibiotic-free, fixed-dose combination gel with adapalene (A) 0.1% and benzoyl peroxide (BPO) 2.5% has been developed for treatment of acne vulgaris. Objective To compare the clinical outcomes of A-BPO combination gel with vehicle gel for treatment or maintenance therapy of patients with acne vulgaris. Methods An electronic search of the database PubMed (1966 to September 2012), Embase (1984 to September 2012), and Cochrane Controlled Trials Register (CENTRAL; 3rd Quarter, 2012) was undertaken to identify relevant studies. Main clinical outcomes were success rate, treatment-related adverse events (AEs), AEs leading to discontinuation, satisfaction with the effectiveness, and overall satisfaction. Results Six studies were finally included in this meta-analysis. The A-BPO group yielded better clinical outcomes regarding the success rate (p<0.00001), satisfaction with the effectiveness of treatment (p=0.005), and overall satisfaction (p=0.005) compared to the vehicle group. The incidence of treatment-related AEs in the A-BPO group was comparable with that of vehicle group (p=0.09), while the A-BPO group was associated with a slightly increase in the incidence of AEs leading to discontinuation when compared with the vehicle group (p=0.02). Conclusion A-BPO combination gel yields better clinical outcomes including success rate, satisfaction with the effectiveness, and overall satisfaction compared to vehicle gel, despite an increased incidence of AEs leading to discontinuation. The A-BPO combination agent most likely contributes to the treatment of moderate acne vulgaris rather than severe acne vulgaris, but it may be useful in maintenance therapy of patients with severe acne vulgaris. PMID:24648685

  4. A treatment for severe nodular acne: a randomized investigator-blinded, controlled, noninferiority trial comparing fixed-dose adapalene/benzoyl peroxide plus doxycycline vs. oral isotretinoin.

    PubMed

    Tan, J; Humphrey, S; Vender, R; Barankin, B; Gooderham, M; Kerrouche, N; Audibert, F; Lynde, C

    2014-12-01

    Oral isotretinoin (ISO) is the gold standard for severe nodular acne. However, as some patients are unwilling or unable to take, or are intolerant to, ISO, other options are needed. To compare efficacy and safety of oral ISO vs. doxycycline 200 mg plus adapalene 0·1%/benzoyl peroxide 2·5% gel (D+A/BPO) in severe nodular acne over 20 weeks. This was a multicentre, randomized, controlled, noninferiority investigator-blinded study involving 266 subjects. D+A/BPO showed a significantly earlier onset of action in reducing nodules, papules/pustules and total lesions at week 2. ISO was superior in reducing nodules (95·6% vs. 88·7%), papules/pustules (95·2% vs. 79·6%) and total lesions (92·9% vs. 78·2%; all P < 0·01) at week 20. Half as many subjects for D+A/BPO compared with ISO had treatment-related, medically relevant adverse events (33 events in 18·0% of subjects vs. 73 in 33·8% of subjects, respectively). D+A/BPO was noninferior to ISO in the intent-to-treat population [95% confidence interval (CI) -2·7 to 20·8 (P = 0·13); 63·9% vs. 54·9% of subjects, respectively] and per-protocol population [95% CI 3·9-28·6 (P = 0·01); 74·3% vs. 58% of subjects, respectively), based on the composite efficacy/safety end point. D+A/BPO showed a favourable composite efficacy/safety profile compared with ISO. This combination is an alternative to ISO in patients intolerant to, or unable or unwilling to take, oral ISO, and is an option for treatment of severe nodular acne. © 2014 British Association of Dermatologists.

  5. Metal complexes of the nanosized ligand N-benzoyl-N‧-(p-amino phenyl) thiourea: Synthesis, characterization, antimicrobial activity and the metal uptake capacity of its ligating resin

    NASA Astrophysics Data System (ADS)

    Elhusseiny, Amel F.; Eldissouky, Ali; Al-Hamza, Ahmed M.; Hassan, Hammed H. A. M.

    2015-11-01

    The new nanosized N-benzoyl-N‧-(p-amino phenyl) thiourea ligand H2L was synthesized by nanoprecipitation method. The [Cu (H2L)2 Cl]·2H2O, [Zn (H2L)2(OAc)2], [Cd (H2L)2Cl2] and [Hg (H2L)2Cl2] complexes were synthesized and characterized by various physicochemical methods. Results revealed that the ligand act as hypodentate and bonded to the metal ion via the sulfur atom forming mononuclear non-electrolyte diamagnetic complex. Magnetic moment results indicated a reduction of Cu (II) to Cu (I) during the coordination process. Thermal studies demonstrated variable stabilities of the complexes and [Zn (H2L)2(OAc)2] exhibited the highest thermal stability while [Hg (H2L)2Cl2] was volatile. The prepared compounds were screened against different pathogenic microorganisms. The ligand performed high antibacterial activity against certain bacterial strain compared to its complexes, and the standard bacteriocide in use. The ligand was successfully immobilized on modified Amberlite XAD-16 forming the hypodentate ligating resin PS-SO2-H2L. The new resin was characterized and the extent of metal adsorption reached maximum at pH 6.0 for Cu (II), Cd (II) and Ag (I), with an adsorption amount of 4.3, 4.0 and 3.7 mmol g-1 respectively. The nanosized H2L represents a new category of promising adsorbent that would have a practical impact on biological and water treatment applications.

  6. Randomized tolerability analysis of clindamycin phosphate 1.2%-tretinoin 0.025% gel used with benzoyl peroxide wash 4% for acne vulgaris.

    PubMed

    Draelos, Zoe Diana; Potts, Aaron; Alió Saenz, Alessandra B

    2010-12-01

    The multiple etiologic factors involved in acne vulgaris make the use of several medications necessary to treat the condition. Use of a fixed combination of clindamycin phosphate 1.2% and tretinoin 0.025% in conjunction with a benzoyl peroxide (BPO) wash 4% targets several pathologic factors simultaneously and mitigates the potential for clindamycin-induced Propionibacterium acnes-resistant strains. New formulations may allow such regimens to be effectively used without overly reduced tolerability resulting from the irritation potential of tretinoin and BPO. This randomized, single-blind study investigated the local tolerability, irritation potential, and safety of an aqueous-based gel (clindamycin phosphate 7.2%-tretinoin 0.025% [CT gel]) when used in conjunction with a BPO wash 4% in participants with mild to moderate acne vulgaris. Participants applied the CT gel once daily in the evening for 4 weeks in conjunction with once-daily morning use of either BPO wash 4% or nonmedicated soap-free cleanser lotion (SFC). Local tolerability and irritation potential were assessed by participants and investigators using separate 6-point scales. The frequency and severity of dryness, scaling, erythema, burning/stinging, and itching increased during the first week of treatment in both treatment arms but decreased thereafter. Local tolerability reactions were slightly more frequent in the CT gel + BPO wash group versus the CT gel + SFC group at week 1 but were generally mild and improved within 1 to 2 weeks. In conclusion, therapy with CT gel + BPO wash appears safe and well-tolerated in participants with mild to moderate acne vulgaris.

  7. Multicenter study for efficacy and safety evaluation of a fixeddose combination gel with adapalen 0.1% and benzoyl peroxide 2.5% (Epiduo® for the treatment of acne vulgaris in Brazilian population*

    PubMed Central

    Sittart, José Alexandre de Souza; da Costa, Adilson; Mulinari-Brenner, Fabiane; Follador, Ivonise; Azulay-Abulafia, Luna; de Castro, Lia Cândida Miranda

    2015-01-01

    BACKGROUND The current options for the treatment of acne vulgaris present many mechanisms of action. For several times, dermatologists try topical agents combinations, looking for better results. OBJECTIVES To evaluate the efficacy, tolerability and safety of a topical, fixed-dose combination of adapalene 0.1% and benzoyl peroxide 2.5% gel for the treatment of acne vulgaris in the Brazilian population. METHODS This is a multicenter, open-label and interventionist study. Patients applied 1.0 g of the fixed-dose combination of adapalene 0.1% and benzoyl peroxide 2.5% gel on the face, once daily at bedtime, during 12 weeks. Lesions were counted in all of the appointments, and the degree of acne severity, overall improvement, tolerability and safety were evaluated in each visit. RESULTS From 79 recruited patients, 73 concluded the study. There was significant, fast and progressive reduction of non-inflammatory, inflammatory and total number of lesions. At the end of the study, 75.3% of patients had a reduction of >50% in non-inflammatory lesions, 69.9% in inflammatory lesions and 78.1% in total number of lesions. Of the 73 patients, 71.2% had good to excellent response and 87.6% had satisfactory to good response. In the first week of treatment, erythema, burning, scaling and dryness of the skin were frequent complaints, but, from second week on, these signals and symptoms have reduced. CONCLUSION The fixed-dose combination of adapalene 0.1% and benzoyl peroxide 2.5% gel is effective, safe, well tolerated and apparently improves patient compliance with the treatment. PMID:27168522

  8. Comparison of clindamycin 1% and benzoyl peroxide 5% gel to a novel composition containing salicylic acid, capryloyl salicylic acid, HEPES, glycolic acid, citric acid, and dioic acid in the treatment of acne vulgaris.

    PubMed

    Baumann, Leslie S; Oresajo, Christian; Yatskayer, Margarita; Dahl, Amanda; Figueras, Kristian

    2013-03-01

    This study evaluated the tolerance and efficacy of 2 facial skin products in subjects with acne using the following acne treatments: 1) treatment A, a combination of salicylic acid, capryloyl salicylic acid, HEPES, glycolic acid, citric acid, and dioic acid, and 2) treatment B (BenzaClin®, clindamycin 1% and benzoyl peroxide 5% gel). The treatment design included the split-face application of treatment A and treatment B and the full-face application of the cleanser, moisturizer, and sunscreen. Data were collected through physician visual assessments, subject irritation questionnaires and assessments, along with clinical photography. Results showed similar tolerance and efficacy for both treatments.

  9. 6,7-dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain.

    PubMed

    Zhu, Yun-Fei; Wilcoxen, Keith; Gross, Timothy; Connors, Patrick; Strack, Nathalie; Gross, Raymond; Huang, Charles Q; McCarthy, James R; Xie, Qiu; Ling, Nicholas; Chen, Chen

    2003-06-02

    A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of 1 included the replacement of the 3,4-dihydroxybenzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K(i)=9.4 nM) but with one less of the labile catechol functionality of 1.

  10. Crystal structures of 2′-benzoyl-1′-(4-methyl­phenyl)-1,1′,2,2′,5′,6′,7′,7a′-octa­hydro­spiro­[indole-3,3′-pyrrolizin]-2-one and 2′-(4-bromo­benzoyl)-1′-(2-chloro­phen­yl)-1,1′,2,2′,5′,6′,7′,7a′-octa­hydro­spiro­[indole-3,3′-pyrrolizin]-2-one

    PubMed Central

    Chandrarekha, M.; Srinivasan, N.; Kottala Vijaya, P.; Siva, A.; Krishnakumar, R. V.

    2016-01-01

    The two title compounds, C28H26N2O2, (I), and C27H22BrClN2O2, (II), differ in their substituents, viz.4-methyl­phenyl and benzoyl rings in (I) replaced by 2-chloro­phenyl and 4- bromo­benzoyl, respectively, in (II). A significant difference between the two mol­ecules is found in the deviation of the benzoyl O atom from the least-squares plane of the ring to which it is attached [0.593 (4) and 0.131 (3) Å, respectively], a fact which may be attributed to the different participation of the benzoyl O atoms as acceptors in their inter­molecular C—H⋯O inter­actions. The chemical modifications in (I) and (II) do not seem to affect the type nor strength of the inter­molecular N—H⋯N and C—H⋯O hydrogen bonds responsible for the two crystal structures, such that the aggregation of mol­ecules appears similar in spite of the mol­ecular changes. PMID:27840725

  11. Determination of the tautomeric equilibria of pyridoyl benzoyl β-diketones in the liquid and solid state through the use of deuterium isotope effects on (1)H and (13)C NMR chemical shifts and spin coupling constants.

    PubMed

    Hansen, Poul Erik; Borisov, Eugeny V; Lindon, John C

    2015-02-05

    The tautomeric equilibria for 2-pyridoyl-, 3-pyridoyl-, and 4-pyridoyl-benzoyl methane have been investigated using deuterium isotope effects on (1)H and (13)C chemical shifts both in the liquid and the solid state. Equilibria are established both in the liquid and the solid state. In addition, in the solution state the 2-bond and 3-bond J((1)H-(13)C) coupling constants have been used to confirm the equilibrium positions. The isotope effects due to deuteriation at the OH position are shown to be superior to chemical shift in determination of equilibrium positions of these almost symmetrical -pyridoyl-benzoyl methanes. The assignments of the NMR spectra are supported by calculations of the chemical shifts at the DFT level. The equilibrium positions are shown to be different in the liquid and the solid state. In the liquid state the 4-pyridoyl derivative is at the B-form (C-1 is OH), whereas the 2-and 3-pyridoyl derivatives are in the A-form. In the solid state all three compounds are on the B-form. The 4-pyridoyl derivative shows unusual deuterium isotope effects in the solid, which are ascribed to a change of the crystal structure of the deuteriated compound. Copyright © 2013 Elsevier B.V. All rights reserved.

  12. Synthesis, spectroscopic and theoretical studies of ethyl (2E)-3-amino-2-({[(4-benzoyl-1,5-diphenyl-1H-pyrazol-3-yl)carbonyl]amino}carbonothioyl)but-2-enoate butanol solvate.

    PubMed

    Koca, İrfan; Sert, Yusuf; Gümüş, Mehmet; Kani, İbrahim; Çırak, Çağrı

    2014-01-24

    We have synthesized ethyl (2E)-3-amino-2-({[(4-benzoyl-1,5-diphenyl-1H-pyrazol-3-yl)carbonyl]amino}carbonothioyl)but-2-enoate (2) by the reaction of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carbonyl chloride (1), ammonium thiocyanate and ethyl 3-aminobut-2-enoate and then characterized by elemental analyses, IR, Raman, (1)H NMR, (13)C NMR and X-ray diffraction methods. The experimental and theoretical vibrational spectra of 2 were investigated. The experimental FT-IR (4000-400 cm(-1)) and Laser-Raman spectra (4000-100 cm(-1)) of the molecule in the solid phase were recorded. Theoretical vibrational frequencies and geometric parameters (bond lengths, bond angles) were calculated using Ab Initio Hartree Fock (HF), Density Functional Theory (B3LYP) methods with 6-311++G(d,p) basis set by Gaussian 09W program. The computed values of frequencies are scaled using a suitable scale factor to yield good coherence with the observed values. The assignments of the vibrational frequencies were performed by potential energy distribution (PED) analysis by using VEDA 4 program. The theoretical optimized geometric parameters and vibrational frequencies were compared with the corresponding experimental X-ray diffraction data, and they were seen to be in a good agreement with each other. Also, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies were calculated.

  13. Supra-molecular architecture in a co-crystal of the N(7)-H tautomeric form of N (6)-benzoyl-adenine with adipic acid (1/0.5).

    PubMed

    Swinton Darious, Robert; Thomas Muthiah, Packianathan; Perdih, Franc

    2016-06-01

    The asymmetric unit of the title co-crystal, C12H9N5O·0.5C6H10O4, consists of one mol-ecule of N (6)-benzoyl-adenine (BA) and one half-mol-ecule of adipic acid (AA), the other half being generated by inversion symmetry. The dihedral angle between the adenine and phenyl ring planes is 26.71 (7)°. The N (6)-benzoyl-adenine mol-ecule crystallizes in the N(7)-H tautomeric form with three non-protonated N atoms. This tautomeric form is stabilized by intra-molecular N-H⋯O hydrogen bonding between the carbonyl (C=O) group and the N(7)-H hydrogen atom on the Hoogsteen face of the purine ring, forming an S(7) ring motif. The two carboxyl groups of adipic acid inter-act with the Watson-Crick face of the BA mol-ecules through O-H⋯N and N-H⋯O hydrogen bonds, generating an R 2 (2)(8) ring motif. The latter units are linked by N-H⋯N hydrogen bonds, forming layers parallel to (10-5). A weak C-H⋯O hydrogen bond is also present, linking adipic acid mol-ecules in neighbouring layers, enclosing R (2) 2(10) ring motifs and forming a three-dimensional structure. C=O⋯π and C-H⋯π inter-actions are also present in the structure.

  14. Cardiotonic agents. 7. Prodrug derivatives of 4-ethyl-1,3-dihydro- 5-[4-(2-methyl-1H-imidazol-1-yl)benzoyl]-2H-imidazol-2-one.

    PubMed

    Shaw, K J; Erhardt, P W; Hagedorn, A A; Pease, C A; Ingebretsen, W R; Wiggins, J R

    1992-04-03

    The cardiotonic agent 4-ethyl-1,3-dihydro-5-4-(2-methyl-1H-imidazol-1-yl)benzoyl]-2H- imidazol-2-one (1) was found to have low bioavailability when administered orally to rats and dogs. A series of N-acyl derivatives, an underutilized prodrug of acidic NH compounds, has been synthesized and tested for their ability to improve the oral bioavailability of 1. Reaction of the monosodium salt of 1 with various anhydrides afforded the N-1 monoacylimidazolones with surprisingly high regioselectivity. In addition to the prodrugs, acylation of 1 with propionic or phenylacetic anhydride led to the novel 3H-pyrrolo[1,2-c]imidazole-3,5(2H)-diones 6. The prodrugs showed a significant increase in the partition coefficients with a minor decrease in the aqueous solubility. The benzoyl derivative 4b exhibited the highest stability in both pH 1.5 and 7.4 buffer solutions. Further evaluation of 4b showed rapid conversion to 1 in canine plasma (t1/2 = 38 min), and human plasma (t1/2 = 10 min). Oral studies indicated that the bioavailability of 4b was increased to greater than 75% (compared to less than 20% for 1), and hemodynamic studies demonstrated that the selective inotropic profile of 1 was retained.

  15. Adapalene 0.1% and benzoyl peroxide 2.5% as a fixed-dose combination gel is as well tolerated as the individual components alone in terms of cumulative irritancy.

    PubMed

    Loesche, Christian; Pernin, Colette; Poncet, Michel

    2008-01-01

    International guidelines recommend the combination of retinoids (e.g. adapalene, tazarotene) and benzoyl peroxide for treating acne because of their complementary mechanisms of action. A new fixed-dose combination gel of adapalene 0.1% and benzoyl peroxide (BPO) 2.5% (adapalene/BPO*) is an effective acne treatment and offers the advantage of a once daily application. This paper reports the results of a cumulative irritancy study in healthy volunteers comparing adapalene/BPO to adapalene 0.1% and BPO 2.5% applied separately, BPO 10% gel, tazarotene 0.1% gel and the gel vehicle as a control.There was no significant difference between the mean cumulative irritation index (MCII) for adapalene/BPO and any test product except tazarotene 0.1% gel, which had a significantly greater MCII than all other test products (p < 0.05). This study showed that adapalene/BPO as a fixed-dose combination is as well tolerated as BPO 2.5% gel alone or adapalene 0.1% gel alone in terms of cumulative irritancy.*Epiduo, Galderma S.A.

  16. Synthesis, spectroscopic and theoretical studies of ethyl (2E)-3-amino-2-({[(4-benzoyl-1,5-diphenyl-1H-pyrazol-3-yl)carbonyl]amino}carbonothioyl)but-2-enoate butanol solvate

    NASA Astrophysics Data System (ADS)

    Koca, İrfan; Sert, Yusuf; Gümüş, Mehmet; Kani, İbrahim; Çırak, Çağrı

    2014-01-01

    We have synthesized ethyl (2E)-3-amino-2-({[(4-benzoyl-1,5-diphenyl-1H-pyrazol-3-yl)carbonyl]amino}carbonothioyl)but-2-enoate (2) by the reaction of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carbonyl chloride (1), ammonium thiocyanate and ethyl 3-aminobut-2-enoate and then characterized by elemental analyses, IR, Raman, 1H NMR, 13C NMR and X-ray diffraction methods. The experimental and theoretical vibrational spectra of 2 were investigated. The experimental FT-IR (4000-400 cm-1) and Laser-Raman spectra (4000-100 cm-1) of the molecule in the solid phase were recorded. Theoretical vibrational frequencies and geometric parameters (bond lengths, bond angles) were calculated using Ab Initio Hartree Fock (HF), Density Functional Theory (B3LYP) methods with 6-311++G(d,p) basis set by Gaussian 09W program. The computed values of frequencies are scaled using a suitable scale factor to yield good coherence with the observed values. The assignments of the vibrational frequencies were performed by potential energy distribution (PED) analysis by using VEDA 4 program. The theoretical optimized geometric parameters and vibrational frequencies were compared with the corresponding experimental X-ray diffraction data, and they were seen to be in a good agreement with each other. Also, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies were calculated.

  17. Acne subject preference for pump over tube for dispensing fixed-dose combination adapalene 0.1%-benzoyl peroxide 2.5% gel.

    PubMed

    Rueda, Maria J

    2014-06-01

    Acne is a chronic inflammatory disease. Key to a patient's success on fixed-dose adapalene-benzoyl peroxide (BPO) gel is ensuring adherence. Use of a pump system to deliver a pre-measured amount of gel with each pressure enables application of a more consistent dose vs. the tube, which should improve adherence. In the present study, we evaluate patient preference for two different containers for dispensing adapalene-BPO gel. In this 15-day, open-label study, 300 subjects were asked to treat their acne using fixed-dose adapalene 0.1%-BPO 2.5% gel dispensed in either a tube or a pump once-daily for up to 7 days. At week 1, subjects switched to the alternative packaging design for the same timeframe. At the end of the treatment period, subjects were asked to complete a subject preference survey. Among subjects completing the survey (n = 291), 79.0% (n = 230) preferred the pump for dispensing adapalene-BPO gel and 21.0% (n = 61) preferred the tube (p < 0.001). The top three characteristics of the pump were that it was easy to use (89.0%; n = 259/291), clean (73.2%; n = 213/291) and convenient (69.4%; n = 202/291). When asked to rate their experience with using the pump, 91.8% (n = 267/291; p < 0.001) of subjects reported being satisfied on a self-assessment scale. The majority of subjects stated they would tell their doctor about their preference for the pump next time adapalene-BPO gel was prescribed (76.6%; n = 223/291; p < 0.001) and would prefer the pump if both containers cost the same amount (80.1%; n = 233/291; p < 0.001). Patients prefer using a pump instead of a tube to dispense adapalene-BPO gel. This delivery mechanism helps to ensure consistent application and thus may improve patient adherence to the prescribed acne treatment regimen.

  18. Fixed-Combination Gels of Adapalene and Benzoyl Peroxide Provide Optimal Percutaneous Absorption Compared to Monad Formulations of These Compounds: Results from Two In Vitro Studies.

    PubMed

    Osman-Ponchet, Hanan; Sevin, Karine; Gaborit, Alexandre; Wagner, Nathalie; Poncet, Michel

    2017-03-01

    Adapalene 0.1%/benzoyl peroxide 2.5% (0.1% A/BPO) and adapalene 0.3%/BPO 2.5% (0.3% A/BPO) gels are fixed-combination options for the topical treatment of acne. However, the active compounds of these combinations are also available as monads, to be used in association or as monotherapy. These two in vitro studies determined the effect of different treatment regimens on the percutaneous absorption of adapalene (0.1% and 0.3%) gels and BPO 2.5% gel in ex vivo human skin. In vitro percutaneous absorption studies were conducted using full-thickness human skin from six donors. Treatment regimens included the application of 0.1% A/BPO, 0.3% A/BPO, or four free-combination regimens of the monads. Skin samples were incubated for 24 h. Concentrations of adapalene and BPO equivalent (BPO-eq) (i.e. benzoic acid after chemical transformation of BPO) were measured using high-performance liquid chromatography. Comparison of regimens was performed using a bioequivalence criterion (estimated ratio bewteen 0.8 and 1.25). The fixed combination 0.3% A/BPO regimen demonstrated more than three times higher absorption of adapalene versus the fixed-combination 0.1% A/BPO. Based on the bioequivalence acceptance criterion, all four free-combination regimens were different from 0.1% A/BPO and 0.3% A/BPO, with higher adapalene release delivered by the fixed combinations versus the free combinations. For BPO-eq, the results showed that the free-combination regimens where adapalene 0.1% was applied first were different from 0.1% A/BPO, with lower BPO-eq release delivered by these regimens compared to the fixed combination. The regimen adapalene 0.3% for 10 h followed by BPO 2.5% delivered lower BPO-eq release compared to the fixed combination. The fixed-combination A/BPO gels provide optimal percutaneous absorption of the active compounds compared to free combinations of adapalene 0.1%, adapalene 0.3%, and BPO 2.5%. The higher concentration of adapalene in the 0.3% A/BPO gel and the

  19. Fixed-Dose Combination Gel of Adapalene and Benzoyl Peroxide plus Doxycycline 100 mg versus Oral Isotretinoin for the Treatment of Severe Acne: Efficacy and Cost Analysis.

    PubMed

    Penna, Pete; Meckfessel, Matthew H; Preston, Norman

    2014-01-01

    Acne vulgaris is a chronic skin disease with a high prevalence. Left untreated or inadequately treated, acne vulgaris can lead to psychological and physical scarring, as well as to unnecessary medical expenses. Oral isotretinoin is an effective treatment for severe resistant nodular and conglobate acne vulgaris. A regimen consisting of a fixed-dose combination of adapalene and benzoyl peroxide gel, 0.1%/2.5% (A-BPO) with oral doxycycline 100 mg (A-BPO/D) has been demonstrated to be efficacious and well tolerated in patients with severe acne and may be an alternative to oral isotretinoin for some patients with severe acne. The objective of this analysis was to compare the relative efficacy and associated costs of A-BPO/D versus oral isotretinoin. In this analysis, comparisons of relative efficacy were made using previously published studies involving similar patient populations with severe acne that warrant the use of oral isotretinoin. The pricing for oral doxycycline and oral isotretinoin was estimated based on the maximum allowable cost from 9 states, and the pricing for A-BPO was calculated as the range between the average wholesale price and the wholesale acquisition cost. For this analysis, 2 treatment models were generated to compare costs: (1) a basic treatment model that examined the costs of an initial regimen of either A-BPO/D or oral isotretinoin without considering probable outcomes, and (2) a long-term model that factored in likely treatment outcomes and subsequent treatments into associated costs. The basic treatment model assumed that patients would be prescribed a single regimen of A-BPO/D for 12 weeks or oral isotretinoin for 20 weeks. The long-term model considered the probability of each treatment successfully managing patients' acne, as well as likely additional regimens of A-BPO monotherapy or an additional regimen of oral isotretinoin. As a result of different treatment durations, the costs for each treatment were normalized to weekly cost of

  20. Vibrational spectroscopy investigation using ab initio and density functional theory analysis on the structure of 3-(6-benzoyl-2-oxobenzo[ d]oxazol-3(2 H)-yl)propanoic acid

    NASA Astrophysics Data System (ADS)

    Arslan, Hakan; Algül, Öztekin; Önkol, Tijen

    2008-08-01

    The molecular structure, vibrational frequencies and infrared intensities of the 3-(6-benzoyl-2-oxobenzo[ d]oxazol-3(2 H)-yl)propanoic acid were calculated by the HF and DFT methods using 6-31G(d) basis set. The FT-infrared spectra have been measured for the title compound in the solid state. We obtained 11 stable conformers for the title compound, however the Conformer 1 is approximately 3.88 kcal/mol more stable than the Conformer 11. The comparison of the theoretical and experimental geometry of the title compound shows that the X-ray parameters fairly well reproduce the geometry of the Conformer 1. The harmonic vibrations computed of this compound by the B3LYP/6-31G(d) method are in a good agreement with the observed IR spectral data. Theoretical vibrational spectra of the title compound were interpreted by means of PEDs using VEDA 4 program.

  1. Crystal structure of bis­(μ-2-benzoyl­benzoato-κ2 O:O′)bis­[bis­(2,2′-bi­pyridine-κ2 N,N′)manganese(II)] bis­(perchlorate)

    PubMed Central

    Kani, Ibrahim

    2015-01-01

    The title compound, [Mn2(C6H5COC6H4COO)2(C10H8N2)4](ClO4)2, comprises a centrosymmetric binuclear cation and two perchlorate anions. In the complex cation, two MnII atoms are bridged by two O atoms of two different 2-benzoyl­benzoate ligands, each MnII atom being further coordinated by two 2,2′-bi­pyridine (bipy) ligands in a distorted octa­hedral environment. Within the binuclear mol­ecule, the Mn⋯Mn separation is 4.513 (7) Å. Inter­molecular C—H⋯O and C—H⋯ π inter­actions link the mol­ecules into a three-dimensional network. PMID:26870457

  2. Synthesis and pharmacological evaluation of novel 1-(2-(benzoyl-substituted-2-phenyl-1H-indol-5-carbony) hydrazinyloxy) vinyl nitrate derivatives as potent non-ulcerogenic, analgesic and anti-inflammatory agents.

    PubMed

    Mokale, Vinod J; Raut, Mayuresh K; Burange, Prashant J; Dhoot, Navneet S; Bhandari, Shashikant V; Bothara, Kailash G; Naik, Jitendra B

    2010-07-01

    Six derivatives of 1-(2-(benzoyl-(substituted)-2-phenyl-1H-indole-5-carbony) hydrazinyloxy) vinyl nitrate were synthesized and tested in vivo for anti-inflammatory, analgesic, and ulcerogenic properties. Synthesized compounds shown significant anti-inflammatory activity comparable to that of Diclofenac sodium in the carrageenan-induced rat paw edema test and all of the compounds were found to be equipotent to Diclofenac sodium in the acetic acid induced writhing analgesic model. Out of six derivatives two derivatives found to produce no ulceration in stomach specimen of rats; nitric oxide seems to contribute to their excellent safety profile which supports several endogenous GIT defense mechanisms, including increase in mucus, bicarbonate secretions, increase in mucosal blood flow, and inhibition of the activation of pro-inflammatory cells by which NO-Indomethacin protects GI mucosa.

  3. Design and synthesis of a new class of fluorescent photoaffinity label with specific reference to 4-benzoyl-1-benzamidofluorescein: a new photolabel for adenine nucleotide binding domains on enzymes

    NASA Astrophysics Data System (ADS)

    Rosen, Jane E.

    1993-05-01

    Benzophenone was used as the photoreactive moiety in the synthesis of several water soluble, fluorescent photoaffinity labels. The following compounds were synthesized: 5-(2-(p- benzoylbenzamido)ethylamino-1-napthalenesulfonate (BzEDANS); 5-(2-(p- benzoylbenzamido)hexylamino-1-napthalenesulfonate (BzHDANS); and 4-benzoyl-1- benzamidofluorescein (BzAF). BzEDANS and BzHDANS were found to be unsuitable for use as photochemical probes. They were incapable of photoinduced covalent binding to methylene carbon due to intramolecular triplet-triplet energy transfer. BzAF was synthesized because its fluorescent moiety, fluorescein, is an inefficient acceptor for intramolecular quenching of the benzophenone triplet state diradical intermediate. BzAF was found to be a suitable and efficient photolabel and is presently a prototype for a new class of fluorescent photolabel.

  4. Efficacy and safety of tretinoin 0.025%/clindamycin phosphate 1.2% gel in combination with benzoyl peroxide 6% cleansing cloths for the treatment of facial acne vulgaris.

    PubMed

    Zeichner, Joshua A; Wong, Vicky; Linkner, Rita V; Haddican, Madelaine

    2013-03-01

    Combination therapy using medications with complementary mechanisms of action is the standard of care in treating acne. We report results of a clinical trial evaluating the use of a fixed-dose tretinoin 0.025%/clindamycin phosphate 1.2% (T/CP) gel in combination with a benzoyl peroxide 6% foaming cloth compared with T/CP alone for facial acne. At week 12, the combination therapy group showed a trend toward greater efficacy compared with T/CP alone. There was a high success rate observed in the study, which may be attributable to the large percentage of adult female acne patients enrolled. Cutaneous adverse events were not statistically different in using combination therapy compared with T/CP alone.

  5. Solid state structure and solution thermodynamics of three-centered hydrogen bonds (O∙∙∙H∙∙∙O) using N-(2-benzoyl-phenyl) oxalyl derivatives as model compounds.

    PubMed

    Gómez-Castro, Carlos Z; Padilla-Martínez, Itzia I; García-Báez, Efrén V; Castrejón-Flores, José L; Peraza-Campos, Ana L; Martínez-Martínez, Francisco J

    2014-09-12

    Intramolecular hydrogen bond (HB) formation was analyzed in the model compounds N-(2-benzoylphenyl)acetamide, N-(2-benzoylphenyl)oxalamate and N1,N2-bis(2-benzoylphenyl)oxalamide. The formation of three-center hydrogen bonds in oxalyl derivatives was demonstrated in the solid state by the X-ray diffraction analysis of the geometric parameters associated with the molecular structures. The solvent effect on the chemical shift of H6 [δH6(DMSO-d6)-δH6(CDCl3)] and Δδ(ΝΗ)/ΔT measurements, in DMSO-d6 as solvent, have been used to establish the energetics associated with intramolecular hydrogen bonding. Two center intramolecular HB is not allowed in N-(2-benzoylphenyl)acetamide either in the solid state or in DMSO-d6 solution because of the unfavorable steric effects of the o-benzoyl group. The estimated ΔHº and ΔSº values for the hydrogen bonding disruption by DMSO-d6 of 28.3(0.1) kJ·mol-1 and 69.1(0.4) J·mol-1·K-1 for oxalamide, are in agreement with intramolecular three-center hydrogen bonding in solution. In the solid, the benzoyl group contributes to develop 1-D and 2-D crystal networks, through C-H∙∙∙A (A = O, π) and dipolar C=O∙∙∙A (A = CO, π) interactions, in oxalyl derivatives. To the best of our knowledge, this is the first example where three-center hydrogen bond is claimed to overcome steric constraints.

  6. Supra­molecular architecture in a co-crystal of the N(7)—H tautomeric form of N 6-benzoyl­adenine with adipic acid (1/0.5)

    PubMed Central

    Swinton Darious, Robert; Thomas Muthiah, Packianathan; Perdih, Franc

    2016-01-01

    The asymmetric unit of the title co-crystal, C12H9N5O·0.5C6H10O4, consists of one mol­ecule of N 6-benzoyl­adenine (BA) and one half-mol­ecule of adipic acid (AA), the other half being generated by inversion symmetry. The dihedral angle between the adenine and phenyl ring planes is 26.71 (7)°. The N 6-benzoyl­adenine mol­ecule crystallizes in the N(7)—H tautomeric form with three non-protonated N atoms. This tautomeric form is stabilized by intra­molecular N—H⋯O hydrogen bonding between the carbonyl (C=O) group and the N(7)—H hydrogen atom on the Hoogsteen face of the purine ring, forming an S(7) ring motif. The two carboxyl groups of adipic acid inter­act with the Watson–Crick face of the BA mol­ecules through O—H⋯N and N—H⋯O hydrogen bonds, generating an R 2 2(8) ring motif. The latter units are linked by N—H⋯N hydrogen bonds, forming layers parallel to (10-5). A weak C—H⋯O hydrogen bond is also present, linking adipic acid mol­ecules in neighbouring layers, enclosing R 2 2(10) ring motifs and forming a three-dimensional structure. C=O⋯π and C—H⋯π inter­actions are also present in the structure. PMID:27308047

  7. 5-Amino-6-benzoyl-8-nitro-2,3-di-hydro-1H-spiro-[imidazo[1,2-a]pyridine-7,3'-indolin]-2'-one dimethyl sulfoxide monosolvate.

    PubMed

    Nagalakshmi, R A; Suresh, J; Sivakumar, S; Kumar, R Ranjith; Lakshman, P L Nilantha

    2014-05-01

    In the title compound C21H17N5O4·C2H6OS, the central six-membered ring derived from 1,4-di-hydro-pyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp(2) hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH2 group forms an intra-molecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N-H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N-H⋯O and C-H⋯O hydrogen bonds enclosing R (2) 2(14) ring motifs. The chains are linked via N-H⋯O and C-H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent mol-ecule which acts as both an acceptor and a donor..

  8. Effects of systematic N-terminus deletions and benzoylations of endogenous RF-amide peptides on NPFF1R, NPFF2R, GPR10, GPR54 and GPR103.

    PubMed

    Rouméas, Laurent; Humbert, Jean-Paul; Schneider, Séverine; Doebelin, Christelle; Bertin, Isabelle; Schmitt, Martine; Bourguignon, Jean-Jacques; Simonin, Frédéric; Bihel, Frédéric

    2015-09-01

    Mammalian RF-amide peptides including RF-amide-related peptides-1 and -3, neuropeptides AF and FF, Prolactin releasing peptides, Kisspeptins and RFa peptides are currently considered endogenous peptides for the GPCRs NPFF1R, NPFF2R, GPR10, GPR54 and GPR103, respectively. While NPFF1R and NPFF2R displayed high affinity for all the RF-amide peptides, GPR10, GPR54 and GPR103 only bind their cognate ligands. Through a systematic and sequential N-terminus deletion and benzoylation of either RF-amide neuropeptide (RFRP-3, NPFF, Kp-10, PrRP20, and 26RFa), we report the corresponding impact on affinity and activity towards all the RF-amide receptors (NPFF1R, NPFF2R, GPR10, GPR54 and GPR103). Our results highlight the difficulty to develop selective peptide ligands for GPR10, GPR54 or GPR103 without a modification of the C-terminus RF-amide signature, but open the door to the design of new RF-amide peptides acting as agonist for one receptor and antagonist for another one.

  9. Comparison of the benzoyl-DL-arginine-naphthylamide (BANA) test, DNA probes, and immunological reagents for ability to detect anaerobic periodontal infections due to Porphyromonas gingivalis, Treponema denticola, and Bacteroides forsythus.

    PubMed Central

    Loesche, W J; Lopatin, D E; Giordano, J; Alcoforado, G; Hujoel, P

    1992-01-01

    Most forms of periodontal disease are associated with the presence or overgrowth of anaerobic species that could include Treponema denticola, Porphyromonas gingivalis, and Bacteroides forsythus among others. These three organisms are among the few cultivable plaque species that can hydrolyze the synthetic trypsin substrate benzoyl-DL-arginine-naphthylamide (BANA). In turn, BANA hydrolysis by the plaque can be associated with periodontal morbidity and with the presence of these three BANA-positive organisms in the plaque. In this investigation, the results of the BANA test, which simultaneously detects one or more of these organisms, were compared with the detection of these organisms by (i) highly specific antibodies to P. gingivalis, T. denticola, and B. forsythus; (ii) whole genomic DNA probes to P. gingivalis and T. denticola; and (iii) culturing or microscopic procedures. The BANA test, the DNA probes, and an enzyme-linked immunosorbent assay or an indirect immunofluorescence assay procedure exhibited high sensitivities, i.e., 90 ot 96%, and high accuracies, i.e., 83 to 92%, in their ability to detect combinations of these organisms in over 200 subgingival plaque samples taken from the most periodontally diseased sites in 67 patients. This indicated that if P. gingivalis, T. denticola, and B. forsythus are appropriate marker organisms for an anaerobic periodontal infection, then the three detection methods are equally accurate in their ability to diagnose this infection. The same statement could not be made for the culturing approach, where accuracies of 50 to 62% were observed. PMID:1311335

  10. Synthesis, crystal structures, insecticidal activities, and structure--activity relationships of novel N'-tert-Butyl-N'-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives.

    PubMed

    Huang, Zhiqiang; Liu, Yuxiu; Li, Yongqiang; Xiong, Lixia; Cui, Zhipeng; Song, Hongjian; Liu, Hongli; Zhao, Qiqi; Wang, Qingmin

    2011-01-26

    Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by (1)H NMR spectra, HRMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.

  11. Twelve-week, multicenter, placebo-controlled, randomized, double-blind, parallel-group, comparative phase II/III study of benzoyl peroxide gel in patients with acne vulgaris: A secondary publication.

    PubMed

    Kawashima, Makoto; Sato, Shinichi; Furukawa, Fukumi; Matsunaga, Kayoko; Akamatsu, Hirohiko; Igarashi, Atsuyuki; Tsunemi, Yuichiro; Hayashi, Nobukazu; Yamamoto, Yuki; Nagare, Toshitaka; Katsuramaki, Tsuneo

    2017-03-11

    A placebo-controlled, randomized, double-blind, parallel-group, comparative, multicenter study was conducted to investigate the efficacy and safety of benzoyl peroxide (BPO) gel, administrated once daily for 12 weeks to Japanese patients with acne vulgaris. Efficacy was evaluated by counting all inflammatory and non-inflammatory lesions. Safety was evaluated based on adverse events, local skin tolerability scores and laboratory test values. All 609 subjects were randomly assigned to receive the study products (2.5% and 5% BPO and placebo), and 607 subjects were included in the full analysis set, 544 in the per protocol set and 609 in the safety analyses. The median rates of reduction from baseline to the last evaluation of the inflammatory lesion counts, the primary end-point, in the 2.5% and 5% BPO groups were 72.7% and 75.0%, respectively, and were significantly higher than that in the placebo group (41.7%). No deaths or other serious adverse events were observed. The incidences of adverse events in the 2.5% and 5% BPO groups were 56.4% and 58.8%, respectively; a higher incidence than in the placebo group, but there was no obvious difference between the 2.5% and 5% BPO groups. All adverse events were mild or moderate in severity. Most adverse events did not lead to study product discontinuation. The results suggested that both 2.5% and 5% BPO are useful for the treatment of acne vulgaris.

  12. Extraction studies of selected actinide ions from aqueous solutions with 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and tri-n-octylphosphine oxide

    SciTech Connect

    Hannink, N.J.; Hoffman, D.C. |; Smith, B.F.

    1991-11-01

    The first measurements of distribution coefficients (K{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}`s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}`s for these actinides are about a factor of 5 to 10 greater than the K{sub d}`s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}`s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand.

  13. Extraction studies of selected actinide ions from aqueous solutions with 4-benzoyl-2,4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and Tri-n-octylphosphine oxide

    SciTech Connect

    Hannink, N.J.; Hoffman, D.C.; Smith, B.F.

    1992-07-01

    The first measurements of distribution coefficients (k{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}`s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}`s for these actinides are about about a factor of 10 greater than the K{sub d}`s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}`s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand. 9 refs., 2 figs., 1 tab.

  14. Extraction studies of selected actinide ions from aqueous solutions with 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and tri-n-octylphosphine oxide

    SciTech Connect

    Hannink, N.J.; Hoffman, D.C. California Univ., Berkeley, CA . Dept. of Chemistry); Smith, B.F. )

    1991-11-01

    The first measurements of distribution coefficients (K{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}'s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}'s for these actinides are about a factor of 5 to 10 greater than the K{sub d}'s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}'s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand.

  15. Development and validation of high-performance liquid chromatography-tandem mass spectrometry assay for 6-(3-benzoyl-ureido)-hexanoic acid hydroxyamide, a novel HDAC inhibitor, in mouse plasma for pharmacokinetic studies.

    PubMed

    Yeo, Pauline; Xin, Liu; Goh, Evelyn; New, Lee Sun; Zeng, Peizi; Wu, Xiaofeng; Venkatesh, P; Kantharaj, Ethirajulu

    2007-02-01

    A liquid chromatography/tandem mass spectrometric method for the quantification of 6-(3-benzoyl-ureido)-hexanoic acid hydroxyamide (EX-2), a novel histone deacetylase (HDAC) inhibitor, in mouse plasma was developed to support in-house pharmacokinetic (PK) studies in the lead optimization stage. In order to determine the PK parameters for EX-2 in comparison to other HDAC inhibitors such as suberoylanilide hydroxamic acid (SAHA), PXD-101 and LBH-589, which are currently in different stages of clinical trials, research-grade bio-analytical method validations were carried out for EX-2 and these reference HDAC inhibitors, which were synthesized by in-house medicinal chemists. The components of validation consisted of specificity, extraction efficiency, signal-response of calibration standards, lower limit of quantification, autosampler stability and accuracy and precision of quality control samples. The validated LC/MS/MS methods were accurate and precise. The calibration curve ranged from 1 to 1600 ng/mL for all the analytes. The methods developed were used to quantify EX-2 and other HDAC inhibitors in mouse plasma obtained from pharmacokinetic studies. The results suggest that EX-2 has better PK parameters compared with the reference drugs and is a promising drug development candidate. Copyright 2007 John Wiley & Sons, Ltd.

  16. Synthesis, crystal structure analysis, spectral IR, NMR UV-Vis investigations, NBO and NLO of 2-benzoyl-N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide with use of X-ray diffractions studies along with DFT calculations

    NASA Astrophysics Data System (ADS)

    Demir, Sibel; Sarioğlu, Ahmet Oral; Güler, Semih; Dege, Necmi; Sönmez, Mehmet

    2016-08-01

    The title compound, 2-benzoyl-N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide compound (C22H16NO3Cl) has been synthesized and characterized by X-ray diffraction, IR, 1H and 13C NMR and UV-Vis spectra. Optimized geometrical structure, harmonic vibrational frequencies and chemical shifts were computed using hybrid-DFT (B3LYP and B3PW91) methods and 6-311G(d,p) as the basis set. The results of the optimized molecular structure are presented and compared with the experimental X-ray diffraction. The calculated optimized geometries, vibrational frequencies and 1H NMR chemical shift values are in strong agreement with experimentally measured values. UV-Vis spectrum of the title compound, was also recorded and the electronic properties, such as calculated energies, excitation energies, oscillator strengths, dipole moments and frontier orbital energies and band gap energies were computed with TDDFT-B3LYP methodolgy and using 6-311G(d,p) as the basis set. Furthermore, frontier molecular orbitals (FMO), molecular electrostatic potential (MEP), natural bond orbital (NBO) and non linear optical (NLO) properties were performed by using B3LYP/6-311G(d,p) level for the title compound.

  17. Separation studies of yttrium(III) and lanthanide(III) ions with 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and trioctylphosphine oxide using a robotic extraction system

    SciTech Connect

    Nekimken, H.L.; Smith, B.F.; Jarvinen, G.D.; Bartholdi, C.S.

    1992-07-01

    We studied the extraction of trivalent Y, La, Pr, Nd, Sm, Eu, Gd, Dy, Er, and Lu from aqueous perchlorate solutions using a mixture of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (HBMPPT) and trioctylphosphine oxide (TOPO). The metal ion distribution coefficients (D-values) as a function of increasing lanthanide atomic number increased initially, reached a maximum value at Nd, then decreased to a nearly constant value for Gd and the later lanthanides. The D-values vary slightly across the lanthanide series, the maximum difference being a factor of 14 between La and Nd. Analysis of slopes of plots of log D versus pH, log [HBMPPT], and log [TOPO] indicated that the stoichiometries of the extraction complexes varied across the lanthanide series showing a decrease in the number of HBMPPT (and/or BMPPT) units and an increase in the number of TOPO molecules involved in the major extraction species. This extraction system can provide a good way to separate the trivalent actinides from the trivalent lanthanides. 21 refs., 2 figs., 3 tabs.

  18. Adapalene-benzoyl peroxide, a unique fixed-dose combination topical gel for the treatment of acne vulgaris: a transatlantic, randomized, double-blind, controlled study in 1670 patients.

    PubMed

    Gollnick, H P M; Draelos, Z; Glenn, M J; Rosoph, L A; Kaszuba, A; Cornelison, R; Gore, B; Liu, Y; Graeber, M

    2009-11-01

    Combination therapy utilizing agents with complementary mechanisms of action is recommended by acne guidelines to help simultaneously target multiple pathogenic factors. A unique, topical, fixed-dose combination gel with adapalene 0.1% and benzoyl peroxide (BPO) 2.5% has recently been developed for the once-daily treatment of acne. To evaluate the efficacy and safety of adapalene 0.1%-BPO 2.5% fixed-dose combination gel (adapalene-BPO) relative to adapalene 0.1% monotherapy (adapalene), BPO 2.5% monotherapy (BPO), and the gel vehicle (vehicle) in a large population for the treatment of acne vulgaris. In total, 1670 subjects were randomized in a double-blind controlled trial to receive adapalene-BPO, adapalene, BPO or vehicle for 12 weeks (1 : 1 : 1 : 1 randomization). Evaluations included success rate (subjects 'clear' or 'almost clear'), percentage change in lesion count from baseline, cutaneous tolerability and adverse events. Adapalene-BPO was significantly more effective than corresponding monotherapies, with significant differences in percentage lesion count change observed as early as 1 week. Cutaneous tolerability profile was similar to adapalene. Adverse events were more frequent with the combination therapy (mainly due to an increase in mild-to-moderate dry skin), occurred early in the study, and were transient. Adapalene-BPO provides significantly greater and synergistic efficacy and a faster onset of action with an acceptable safety profile in the treatment of acne vulgaris when compared with the corresponding vehicle and the adapalene and BPO monotherapies.

  19. Crystal structure of di-μ-methano­lato-bis­{[N′-(1-benzoyl­prop-1-en-2-yl)thio­phene-2-carbohydrazidato-κ3 O,N′,O′]oxidovanadium(V)}

    PubMed Central

    Carroccia, Murilo C.; Pesci, Rafaela B. P.; Maia, Pedro Ivo da S.; Deflon, Victor M.

    2014-01-01

    The neutral binuclear mol­ecule of the title complex, [V2(C15H12N2O2S)2(CH3O)2O2], exhibits inversion symmetry and consists of two oxidovanadium(V) (VO)3+ fragments, each coordinated by a dianionic and O,N′,O′-chelating N′-(1-benzoyl­prop-1-en-2-yl)thio­phene-2-carbohydrazidate ligand. The V5+ cations are bridged by two asymmetrically bonding methano­late ligands [V—O = 1.8155 (12) and 2.3950 (13) Å] originating from the deprotonation of the methanol solvent. The coordination sphere of the VV atom is distorted octa­hedral, with the equatorial plane defined by the three donor atoms of the thio­phene-2-carbohydrazidate ligand and the O atom of a methano­late unit. The axial positions are occupied by the oxide group and the remaining methano­late ligand. The axially bound methano­late ligand shows a longer V—O bond length due to the trans influence caused by the tightly bonded oxide group. The packing of the complex mol­ecules is dominated by dispersion forces. PMID:25484678

  20. Crystal structure of di-μ-methano-lato-bis-{[N'-(1-benzoyl-prop-1-en-2-yl)thio-phene-2-carbohydrazidato-κ(3) O,N',O']oxidovanadium(V)}.

    PubMed

    Carroccia, Murilo C; Pesci, Rafaela B P; Maia, Pedro Ivo da S; Deflon, Victor M

    2014-10-01

    The neutral binuclear mol-ecule of the title complex, [V2(C15H12N2O2S)2(CH3O)2O2], exhibits inversion symmetry and consists of two oxidovanadium(V) (VO)(3+) fragments, each coordinated by a dianionic and O,N',O'-chelating N'-(1-benzoyl-prop-1-en-2-yl)thio-phene-2-carbohydrazidate ligand. The V(5+) cations are bridged by two asymmetrically bonding methano-late ligands [V-O = 1.8155 (12) and 2.3950 (13) Å] originating from the deprotonation of the methanol solvent. The coordination sphere of the V(V) atom is distorted octa-hedral, with the equatorial plane defined by the three donor atoms of the thio-phene-2-carbohydrazidate ligand and the O atom of a methano-late unit. The axial positions are occupied by the oxide group and the remaining methano-late ligand. The axially bound methano-late ligand shows a longer V-O bond length due to the trans influence caused by the tightly bonded oxide group. The packing of the complex mol-ecules is dominated by dispersion forces.

  1. An in situ benzoylation-dispersive liquid-liquid microextraction method based on solidification of floating organic droplets for determination of biogenic amines by liquid chromatography-ultraviolet analysis.

    PubMed

    Jia, Shaodong; Ryu, Yeonsuk; Kwon, Sung Won; Lee, Jeongmi

    2013-03-22

    A novel analytical method consisting of in situ derivatization combined with liquid phase microextraction followed by liquid chromatography-ultraviolet detection (LC-UV) was developed to determine the biogenic amines (BAs) of alcoholic beverages. Nine BAs (putrescine, cadaverine, 1,3-diaminopropane, tryptamine, phenylethylamine, spermidine, spermine, histamine, and tyramine) were derivatized in situ with benzoyl chloride, extracted by dispersive liquid-liquid microextraction based on solidification of floating organic droplets (DLLME-SFO), and then chromatographed by LC-UV. Factors influencing the derivatization and extraction efficiency were optimized, including the reaction buffer pH and concentration, amount of derivatization reagent, reaction time, types and volumes of extraction and dispersive solvents, and extraction time. Under the optimized conditions, the method was linear over 0.05-8.0μgmL(-1) with an r(2)≥0.992 and exhibited intra- and inter-day precision less than 8.8% and 11.5%, respectively. The limit of detection ranged between 0.005 and 0.01μgmL(-1). The developed method using a basic LC-UV system is sensitive, rapid, convenient, green, and cost-effective. Moreover, it is versatile and practical for the analysis of BAs, as demonstrated by the successful application in four different types of popular alcoholic beverages (white wine, red wine, rice wine, and beer). Copyright © 2013 Elsevier B.V. All rights reserved.

  2. Synthesis, spectral, electrochemical and X-ray single crystal studies on Ni(II) and Co(II) complexes derived from 1-benzoyl-3-(4-methylpyridin-2-yl) thiourea

    NASA Astrophysics Data System (ADS)

    Saad, Fawaz A.

    2014-07-01

    1-Benzoyl-3-(4-methylpyridin-2-yl) thiourea ligand was coordinated with Ni(II) and Co(II) perchlorate salts to isolate complexes. All the prepared compounds are deliberately investigated by all possible spectral tools. A comparative study for IR spectra reveals the neutral bidentate coordinating nature of the ligand towards the two metal ions. The UV/Vis spectra of the complexes display d-d transition bands proposed an octahedral geometry for the complexes. MS analysis data are concerned especially with the base peak which is corresponding to C28H25N6O2S2 M ion. The fragmentation patterns are relatively matched with each others. Electrochemical studies were carried out using platinum wire and Ag/AgNO3 as counter and reference electrodes, respectively. The data reflect the irreversible nature of the electrode couple and showed two successive one electron transfer process. X-ray single crystal studies are used to verifying the octahedral geometry proposed as well as calculating crystal parameters beside the structural refinements.

  3. Upregulation of DR5 receptor by the diaminothiazole DAT1 [4-amino-5-benzoyl-2-(4-methoxy phenyl amino) thiazole] triggers an independent extrinsic pathway of apoptosis in colon cancer cells with compromised pro and antiapoptotic proteins.

    PubMed

    Thomas, Sannu A; Vasudevan, Smreti; Thamkachy, Reshma; Lekshmi, Swathi U; Santhoshkumar, Thankayyan R; Rajasekharan, Kallikat N; Sengupta, Suparna

    2013-06-01

    Mitochondria mediated signalling is the more common way of apoptosis induction exhibited by many chemotherapeutic agents in cancer cells. Death receptor mediated signalling for apoptosis in many cells also requires further amplification from the mitochondrial pathway activation through tBid. Thus the potential of most chemotherapeutic agents in tumours with intrinsic apoptosis resistance due to changes in molecules involved in the mitochondrial pathway is limited. Diaminothiazoles were shown earlier to bind to tubulin thereby exhibiting cytotoxicity towards different cancer cells. We observed that the lead diaminothiazole, DAT1 [4-amino-5-benzoyl-2-(4-methoxy phenyl amino) thiazole] could induce apoptosis in the colon cancer cell line HCT116 by both pathways. However, in contrast to many other chemotherapeutic agents, DAT1 triggered apoptosis where the intrinsic pathway was blocked by changing the pro and antiapoptotic proteins. An independent extrinsic pathway activation triggered by the upregulation of DR5 receptor accounted for that. The induction of DR5 occurred in the transcriptional level and the essential role of DR5 was confirmed by the fact that siRNA downregulation of DR5 significantly reduced DAT1 induced apoptosis. HCT116 cells were earlier shown to have a type II response for apoptosis induction where extrinsic pathway was connected to the intrinsic pathway via the mediator protein tBid. Our finding thus indicates that the signalling events in the manifestation of apoptosis depend not only on the cancer cell type, but also on the inducer. Our results also place diaminothiazoles in a promising position in the treatment of tumours with compromised apoptotic factors.

  4. Synthesis, spectroscopic and structural evaluation of ethyl 2-cyano-3-{5-[(4-nitro-benzoyl)-hydrazonomethyl]-1H-pyrrol-2-yl}-acrylate using experimental and theoretical approaches

    NASA Astrophysics Data System (ADS)

    Singh, R. N.; Kumar, Amit; Rawat, Poonam; Srivastsva, Anchal

    2013-10-01

    A new C-vinylpyrrole containing aroylhydrazone, ethyl 2-cyano-3-{5-[(4-nitro-benzoyl)-hydrazonomethyl]-1H-pyrrol-2-yl}-acrylate (ECNBHPA) derived from ethyl 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)-acrylate and 4-nitro-benzohydrazide has been characterized by various spectroscopic techniques (1H NMR, 13C NMR, Mass, UV-Visible, Emission, FT-IR). TD-DFT has been used to calculate the various electronic excitations and their nature within molecule. The emission spectra of ECNBHPA show photoluminescent behavior of title molecule. Natural bond orbital (NBO) analysis has been carried out to explore the various conjugative/hyperconjugative interactions within molecule and their second order stabilization energy (E(2)). A combined experimental and theoretical vibrational analysis designates presence of the classical hydrogen bonding N1sbnd H29⋯N9 between pyrrole Nsbnd H as proton donor and N atom of cyanide as proton acceptor. To determine the strength and nature of hydrogen bonding, topological parameters at bond critical points (BCP) have been analyzed by 'Quantum theory of atoms in molecules' (QTAIM) in detail. The result of hydrogen bonding is obvious in 1H NMR, FT-IR and ESP map as down field chemical shift, vibrational red shift and absence of blue colur relative to pyrrole Nsbnd H proton, respectively. Global electrophilicity index (ω = 6.573 eV) shows that title molecule behaves as a strong electrophile. The local reactivity descriptors analyses such as Fukui functions (fk+,fk-), local softnesses (sk+,sk-) and electrophilicity indices (ωk+,ωk-) have been performed to determine the reactive sites within molecule. The first hyperpolarizability (β0) of ECNBHPA has been computed to evaluate the non-linear optical (NLO) response of the investigated molecule.

  5. Synthesis, Characterization And Antitumor Activity Of Copper(II) Complexes, [CuL2] [HL1-3=N,N-Diethyl-N'-(R-Benzoyl)Thiourea (R=H, o-Cl and p-NO2)

    PubMed Central

    Hernández, Wilfredo; Beyer, Lothar; Schröder, Uwe; Richter, Rainer; Ferreira, Jorge; Pavani, Mario

    2005-01-01

    The copper (II) complexes (CuL2) were prepared by reaction of Cu(CH3COO)2 with the corresponding derivatives of acylthioureas in a Cu:HL molar ratio of 1:2. Acylthiourea ligands, N,N-diethyl-N'-(R-benzoyl) thiourea (HL1-3) [R=H, o-Cl and p-NO2] were synthesized in high yield (78-83%) and characterized by elemental analysis, infrared spectroscopy, 1H and 13C NMR spectroscopy. The complexes CuL2 were characterized by elemental analysis, IR, FAB(+)-MS, magnetic susceptibility measurements, EPR and cyclic voltammetry. The crystal structure of the complex Cu(L2)2 shows a nearly square-planar geometry with two deprotonated ligands (L) coordinated to CuII through the oxygen and sulfur atoms in a cis arrangement. The antitumor activity of the copper(II) complexes with acylthiourea ligands was evaluated in vitro against the mouse mammary adenocarcinoma TA3 cell line. These complexes exhibited much higher cytotoxic activity (IC50 values in the range of 3.9-6.9 μM) than their corresponding ligands (40-240 μM), which indicates that the coordination of the chelate ligands around the CuII enhances the antitumor activity and, furthermore, this result confirmed that the participation of the nitro and chloro substituent groups in the complex activities is slightly relevant. The high accumulation of the complexes Cu(L2)2 and Cu(L3)2 in TA3 tumor cells and the much faster binding to cellular DNA than Cu(L1)2 are consistent with the in vitro cytotoxic activities found for these copper complexes. PMID:18365106

  6. N-α-Benzoyl-N5-(2-Chloro-1-Iminoethyl)-L-Ornithine Amide, a Protein Arginine Deiminase Inhibitor, Reduces the Severity of Murine Collagen-Induced Arthritis

    PubMed Central

    Willis, Van C.; Gizinski, Alison M.; Banda, Nirmal K.; Causey, Corey P.; Knuckley, Bryan; Cordova, Kristen N.; Luo, Yuan; Levitt, Brandt; Glogowska, Magdalena; Chandra, Piyanka; Kulik, Liudmila; Robinson, William H.; Arend, William P.; Thompson, Paul R.; Holers, V. Michael

    2011-01-01

    Rheumatoid arthritis is associated with the development of autoantibodies to citrullinated self-proteins. Citrullinated synovial proteins, which are generated via the actions of the protein arginine deiminases (PADs), are known to develop in the murine collagen-induced arthritis (CIA) model of inflammatory arthritis. Given these findings, we evaluated whether N-α-benzoyl-N5-(2-chloro-1-iminoethyl)-L-ornithine amide (Cl-amidine), a recently described pan-PAD inhibitor, could affect the development of arthritis and autoimmunity by treating mice in the CIA model with Cl-amidine on days 0–35. Cl-amidine treatment reduced total synovial and serum citrullination, decreased clinical disease activity by ∼50%, and significantly decreased IgG2a anti-mouse type II collagen Abs. Additionally, histopathology scores and total complement C3 deposition were significantly lower in Cl-amidine–treated mice compared with vehicle controls. Synovial microarray analyses demonstrated decreased IgG reactivity to several native and citrullinated epitopes compared with vehicle controls. Cl-amidine treatment had no ameliorative effect on collagen Ab-induced arthritis, suggesting its primary protective mechanism was not mediated through effector pathways. Reduced levels of citrullinated synovial proteins observed in mice treated with Cl-amidine are consistent with the notion that Cl-amidine derives its efficacy from its ability to inhibit the deiminating activity of PADs. In total, these results suggested that PADs are necessary participants in the autoimmune and subsequent inflammatory processes in CIA. Cl-amidine may represent a novel class of disease-modifying agents that modulate aberrant citrullination, and perhaps other immune processes, necessary for the development of inflammatory arthritis. PMID:21346230

  7. Adapalene-benzoyl peroxide once-daily, fixed-dose combination gel for the treatment of acne vulgaris: a randomized, bilateral (split-face), dose-assessment study of cutaneous tolerability in healthy participants.

    PubMed

    Andres, Philippe; Pernin, Colette; Poncet, Michel

    2008-03-01

    Combination therapy is an effective approach to simultaneously target multiple pathogenic factors of acne. International consensus guidelines recommend the use of topical retinoids and benzoyl peroxide (BPO) for acne treatment. These drugs are often prescribed as a free combination without any safety concern associated with antibiotic use. A 3-week, randomized, controlled, investigator-blinded, single-center, bilateral (split-face), dose-assessment study was conducted comparing the cutaneous tolerability of 2 adapalene-BPO fixed-dose combination products versus various concentrations of BPO monotherapy applied once daily. Sixty healthy participants were randomized to one of the following treatment groups: adapalene 0.1%-BPO 2.5% combination product versus BPO 2.5% monotherapy; adapalene 0.1%-BPO 2.5% combination product versus BPO 5% monotherapy; adapalene 0.1%-BPO 5% combination product versus BPO 5% monotherapy; and adapalene 0.1%-BPO 5% combination product versus BPO 10% monotherapy. Assessments included total sum score (TSS) of irritation signs/ symptoms (erythema, scaling/desquamation, dryness, pruritus, stinging/burning) averaged over all postbaseline visits, individual irritation signs/symptoms (worst score), and adverse events. The overall cutaneous tolerability profile of the adapalene 0.1%-BPO 2.5% combination product was better than the combination with BPO 5% and similar to BPO 2.5% or 5% monotherapy. The combination product with BPO 5% induced significantly more irritation than BPO 5% monotherapy (P < .001) or BPO 10% monotherapy (P = .001). In conclusion, the new fixed-dose adapalene 0.1%-BPO 2.5% combination product provided the best overall cutaneous tolerability profile relative to BPO monotherapy.

  8. A 6-month maintenance therapy with adapalene-benzoyl peroxide gel prevents relapse and continuously improves efficacy among patients with severe acne vulgaris: results of a randomized controlled trial.

    PubMed

    Poulin, Y; Sanchez, N P; Bucko, A; Fowler, J; Jarratt, M; Kempers, S; Kerrouche, N; Dhuin, J-C; Kunynetz, R

    2011-06-01

    Acne vulgaris is a chronic and frequently recurring disease. A fixed-dose adapalene-benzoyl peroxide (adapalene-BPO) gel is an efficacious and safe acne treatment. To assess the long-term effect of adapalene-BPO on relapse prevention among patients with severe acne after successful initial treatments. This is a multicentre, double-blind, randomized and controlled study. In total, 243 subjects who had severe acne vulgaris and at least 50% global improvement after a previous 12-week treatment were randomized into the present study to receive adapalene-BPO gel or its vehicle once daily for 24 weeks. At week 24, compared with vehicle, adapalene-BPO resulted in significantly higher lesion maintenance success rate (defined as having at least 50% improvement in lesion counts achieved in initial treatment) for all types of lesions (total lesions: 78·9% vs. 45·8%; inflammatory lesions: 78·0% vs. 48·3%; noninflammatory lesions: 78·0% vs. 43·3%; all P < 0·001). Significantly more subjects with adapalene-BPO than with vehicle had the same or better Investigator's Global Assessment score at week 24 than at baseline (70·7% vs. 34·2%; P < 0·001). The time when 25% of subjects relapsed was 175 days with adapalene-BPO and 56 days with vehicle (17 weeks earlier; P < 0·0001). Adapalene-BPO led to further decrease of lesion counts during the study and 45·7% of subjects were 'clear' or 'almost clear' at week 24. It was also safe and well tolerated in the study. Adapalene-BPO not only prevents the occurrence of relapse among patients with severe acne, but also continues to reduce disease symptoms during 6 months. © 2011 The Authors. BJD © 2011 British Association of Dermatologists.

  9. Is benzoyl peroxide 3% topical gel effective and safe in the treatment of acne vulgaris in Japanese patients? A multicenter, randomized, double-blind, vehicle-controlled, parallel-group study.

    PubMed

    Kawashima, Makoto; Hashimoto, Hirofumi; Alio Sáenz, Alessandra B; Ono, Makoto; Yamada, Masahiro

    2014-09-01

    Benzoyl peroxide (BPO) as an anti-acne medication is not yet approved in Japan. This study evaluated the efficacy and safety of a once-daily topical application of BPO 3% gel versus an inert vehicle gel in Japanese acne patients. Three hundred and sixty patients were randomized to receive BPO 3% or vehicle for 12 weeks. The primary efficacy end-point was absolute change in number of total lesions (TL) from baseline to week 12 to demonstrate the superiority of BPO 3% versus vehicle. Secondary efficacy end-points were absolute and percent change in TL, inflammatory lesions (IL), non-inflammatory lesions (non-IL) and Investigator's Static Global Assessment (ISGA). Change in TL counts from baseline to week 12 for BPO 3% was superior to vehicle (difference, -21.0; P < 0.001). Absolute and percent reductions in TL, IL and non-IL counts were greater for BPO 3% at all study visits. The proportion of patients with improvement in ISGA scores was significantly higher with BPO 3% than with vehicle from week 2. All adverse events were mild or moderate. Adverse drug-related reactions were higher for BPO 3% (30%) than with vehicle (5%). Local tolerability scores of grade 1 or more (slight to moderate) were more frequent with BPO 3% than vehicle with the most significant differences observed in dryness (56% vs 27% at week 1-4), peeling (19% vs 9% at week 1-2) and burning/stinging (58% vs 15% at week 1-12). These results indicate that BPO 3% is effective while maintaining a favorable safety and tolerability profile in Japanese acne patients.

  10. Open-label, randomized, multicenter, phase III study to evaluate the safety and efficacy of benzoyl peroxide gel in long-term use in patients with acne vulgaris: A secondary publication.

    PubMed

    Kawashima, Makoto; Nagare, Toshitaka; Katsuramaki, Tsuneo

    2017-02-02

    An open-label, randomized, multicenter study was conducted to evaluate the safety and efficacy of long-term use of 2.5% and 5% benzoyl peroxide (BPO) gels administrated once daily for 52 weeks to Japanese patients with acne vulgaris. The efficacy of the study drugs was evaluated by counting inflammatory lesions and non-inflammatory lesions. Safety was evaluated based on adverse events, local skin tolerability scores and laboratory test values. In total, 458 subjects were included in the efficacy and safety analyses. The total lesion count, the efficacy end-point, was similarly changed both in the 2.5% and 5% BPO groups over the course of the study. The median rates of reduction from baseline to week 12 were approximately 65%. Thereafter, the counts were maintained at a reduced level without increasing until week 52. The median rates at week 52 were approximately 80%. Similar trends were observed for inflammatory and non-inflammatory lesion counts. Bacteriological evaluation indicated similar distribution of the minimum inhibitory concentration of each of the antibacterial drugs against Propionibacterium acnes between the values at baseline and at week 52, suggesting that long-term use did not result in changes in the drug sensitivity. The incidence of adverse events was 84.0% in the 2.5% BPO group and 87.2% in the 5% BPO group. Many of the adverse events occurred within the first month and were mild or moderate in severity and transient. The results suggest that both 2.5% and 5% BPO gels are effective and safe for long-term treatment of patients with acne vulgaris.

  11. 1H NMR spectroscopic and quantum chemical studies on a poly(ester amide) model compound: Nalpha-benzoyl-L-argininate ethyl ester chloride. Structural preferences for the isolated molecule and in solution.

    PubMed

    Fonseca, A C; Jarmelo, S; Carvalho, R A; Fausto, R; Gil, M H; Simões, P N

    2010-05-13

    The molecular structure of the L-arginine derivative, N(alpha)-benzoyl-L-argininate ethyl ester chloride (BAEEH(+).Cl(-)), was characterized by combining quantum chemical methods and (1)H NMR spectroscopy. A conformational search on the potential energy surfaces of the three lowest-energy tautomers of BAEEH(+) [A: R-N(+)H=(NH(2))(2); B: R-NH-C(=NH)N(+)H(3); C: R-N(+)H(2)-C(=NH)NH(2); R = C(6)H(5)C(=O)NH-CH(COOCH(2)CH(3))CH(2)CH(2)CH(2)-] was carried out using the semiempirical PM3 method. The lowest-energy conformations obtained using this method were then optimized at the DFT(B3LYP)/6-31++G(d,p) level of theory. For all tautomers, it was found that all low-energy conformers present folded structures, in which a H-bond interaction between the guanidinium group and the amide carbonyl oxygen atom appears to be the most relevant stabilizing factor. (1)H NMR spectra of BAEEH(+).Cl(-) in DMF-D(7) were acquired in the temperature range [-55 to 75 degrees C], providing information about the rotational motions in the guanidinium group and showing that the tautomeric form of BAEEH(+) that exists in solution is tautomer A. The interpretation of the experimental findings was supported by (1)H NMR chemical shifts obtained theoretically at the DFT(B3LYP)/6-31++G(d,p) level of approximation, using both the polarized continuum model and a BAEEH(+)-water complex model.

  12. Synthesis and Characterization of Ru(II) Tris(1,1O-phenanthroline)-Electron Acceptor Dyads Incorporating the 4-benzoyl-N-methylpyridinium Cation or N-Benzyl-N'-methyl-viologen. Improving the Dynamic Range, Sensitivity and Response Time of Sol-Gel Based Optical Oxygen Sensors

    NASA Technical Reports Server (NTRS)

    Leventis, Nicholas; Rawashdeh, Abdel-Monen M.; Elder, Ian A.; Yang, Jinhua; Dass, Amala; Sotiriou-Leventis, Chariklia

    2004-01-01

    The title compounds (1 and 2, above) were synthesized by Sonogashira coupling reactions of appropriate Ru(1I) complexes with the electron a cceptors. Characterization was conducted in solution and in frozen ma trices. Finally, the title compounds were evaluated as dopants of sol-gel materials. It was found that the intramolecular quenching efficie ncy of 4-benzoyl-Nmethylpyridinium cation in solution depends on the solvent: photoluminescence is quenched completely in CH,CN, but not i n methanol or ethanol. On the other hand, intramolecular emission que nching by 4-benzyl-N-methyl viologen is complete in all solvents. The difference between the two quenchers is traced electrochemically to t he solvation of the 4-benzoyl-Nmethylpyridiniums by alcohol. In froze n matrices or adsorbed on the surfaces of silica aerogel, both Ru(I1) complex/electron acceptor dyads of this study are photoluminescent, and the absence of quenching has been traced to the environmental rigi dity. When doped aerogels are cooled at 77 K, the emission intensity increases by approximately 4x, and the spectra shift to the blue, analogous to what is observed with Ru(I1) complexes in solutions undergoi ng fluid-to-rigid transition. However, in contrast to frozen solution s, the luminescent moieties in the bulk of aerogels kept at low tempe ratures are still accessible to gas-phase quenchers diffusing through the mesopores, leading to more sensitive platforms for sensors than o ther room-temperature configurations. Thus the photoluminescence of o ur Ru(I1) complex dyads adsorbed on aerogel is quenchable by O2 both at room temperature and at 77 K. Furthermore, it was also found that O 2 modulates the photoluminescence of aerogels doped with 4-benzoyl -N -methylpyridinium-based dyads over a wider dynamic range compared wi th aerogels doped with either our vislogen-based dyads or with Ru(I1) tris(1,lO-phenanthroline) itself.

  13. Synthesis and Characterization of Ru(II) Tris(1,1O-phenanthroline)-Electron Acceptor Dyads Incorporating the 4-benzoyl-N-methylpyridinium Cation or N-Benzyl-N'-methyl-viologen. Improving the Dynamic Range, Sensitivity and Response Time of Sol-Gel Based Optical Oxygen Sensors

    NASA Technical Reports Server (NTRS)

    Leventis, Nicholas; Rawashdeh, Abdel-Monen M.; Elder, Ian A.; Yang, Jinhua; Dass, Amala; Sotiriou-Leventis, Chariklia

    2004-01-01

    The title compounds (1 and 2, above) were synthesized by Sonogashira coupling reactions of appropriate Ru(1I) complexes with the electron a cceptors. Characterization was conducted in solution and in frozen ma trices. Finally, the title compounds were evaluated as dopants of sol-gel materials. It was found that the intramolecular quenching efficie ncy of 4-benzoyl-Nmethylpyridinium cation in solution depends on the solvent: photoluminescence is quenched completely in CH,CN, but not i n methanol or ethanol. On the other hand, intramolecular emission que nching by 4-benzyl-N-methyl viologen is complete in all solvents. The difference between the two quenchers is traced electrochemically to t he solvation of the 4-benzoyl-Nmethylpyridiniums by alcohol. In froze n matrices or adsorbed on the surfaces of silica aerogel, both Ru(I1) complex/electron acceptor dyads of this study are photoluminescent, and the absence of quenching has been traced to the environmental rigi dity. When doped aerogels are cooled at 77 K, the emission intensity increases by approximately 4x, and the spectra shift to the blue, analogous to what is observed with Ru(I1) complexes in solutions undergoi ng fluid-to-rigid transition. However, in contrast to frozen solution s, the luminescent moieties in the bulk of aerogels kept at low tempe ratures are still accessible to gas-phase quenchers diffusing through the mesopores, leading to more sensitive platforms for sensors than o ther room-temperature configurations. Thus the photoluminescence of o ur Ru(I1) complex dyads adsorbed on aerogel is quenchable by O2 both at room temperature and at 77 K. Furthermore, it was also found that O 2 modulates the photoluminescence of aerogels doped with 4-benzoyl -N -methylpyridinium-based dyads over a wider dynamic range compared wi th aerogels doped with either our vislogen-based dyads or with Ru(I1) tris(1,lO-phenanthroline) itself.

  14. Supra­molecular hydrogen-bonding patterns in a 1:1 co-crystal of the N(7)—H tautomeric form of N 6-benzoyl­adenine with 4-hy­droxy­benzoic acid

    PubMed Central

    Swinton Darious, Robert; Thomas Muthiah, Packianathan

    2017-01-01

    The asymmetric unit of the title co-crystal, C12H9N5O·C7H6O3, contains one mol­ecule of N 6-benzoyl­adenine (BA) and one mol­ecule of 4-hy­droxy­benzoic acid (HBA). The N 6-benzoyl­adenine (BA) has an N(7)—H tautomeric form with nonprotonated N-1 and N-3 atoms. This tautomeric form is stabilized by a typical intra­molecular N—H⋯O hydrogen bond between the carbonyl (C=O) group and the N(7)—H hydrogen on the Hoogsteen face of the purine ring, forming a graph-set S(7) ring motif. The primary robust R 2 2(8) ring motif is formed in the Watson–Crick face via N—H⋯O and O—H⋯N hydrogen bonds (involving N1, N6—H and the carboxyl group of HBA). Weak inter­actions, such as, C—H⋯π and π–π are also observed in this crystal structure. PMID:28316815

  15. Safety and efficacy of clindamycin phosphate 1.2%-benzoyl peroxide 3% fixed-dose combination gel for the treatment of acne vulgaris: a phase 3, multicenter, randomized, double-blind, active- and vehicle-controlled study.

    PubMed

    Eichenfield, Lawrence F; Alió Sáenz, Alessandra B

    2011-12-01

    Topical fixed-combination therapy containing 1% clindamycin as 1.2% clindamycin phosphate (CLNP) and 3% benzoyl peroxide (BPO) is an effective treatment for acne vulgaris (acne). To demonstrate that the combination of 1.2% CLNP with lower strength BPO (CLNP 1.2%-BPO 3%) in a gel formulation is superior to each individual ingredient, CLNP 1.2% and BPO 3%, and vehicle gel. A total of 1,319 patients with acne, aged 12 years or older, were enrolled and randomized (1:1:1:1) to receive CLNP 1.2%-BPO 3%, CLNP 1.2% gel, BPO 3% gel, or vehicle gel once-daily in a 12-week, multicenter, double-blind, parallel-group, vehicle-controlled study. Subjects were evaluated at baseline, weeks 2, 4, 8, and 12 or early termination. Assessment of efficacy was evaluated using a six-point Investigator's Static Global Assessment (ISGA) and Subject's Global Assessment (SGA) of acne severity and lesion counts (inflammatory, non-inflammatory, and total). Safety assessments included skin tolerability and adverse events (AEs). A greater proportion of subjects who used CLNP 1.2%-BPO 3% gel (39%) had a two grade improvement in ISGA from baseline to week 12 compared with CLNP 1.2% (25%; P<0.001), BPO 3% (30%; P=0.016), and vehicle (18%; P<0.001). CLNP 1.2%- BPO 3% was superior to CLNP 1.2% and vehicle alone in the absolute reduction from baseline to week 12 in all three lesion types (P<0.001 all pair-wise comparisons). CLNP 1.2%-BPO 3% was superior to BPO 3% alone in the absolute reduction from baseline to week 12 in inflammatory (P=0.015) and total (P=0.032) lesion counts. The incidence of product-related AEs was low and similar in all study groups (1% with CLNP 1.2%-BPO 3%, 2% with CLNP 1.2%, 2% with BPO 3%, and 2% with vehicle). Local tolerability assessments showed similar minimal changes from baseline to week 12 in all study groups. CLNP 1.2%-BPO 3% gel provides superior efficacy to improve ISGA score and reduce inflammatory and total lesion counts compared with the individual active

  16. Customized Single-agent Therapy Management of Severe Inflammatory Acne: A Randomized, Double-blind, Parallel-group, Controlled Study of a New Treatment--Adapalene 0.3%-Benzoyl Peroxide 2.5% Gel.

    PubMed

    Weiss, Jonathan; Stein Gold, Linda; Leoni, Matthew; Rueda, Maria Jose; Liu, Hong; Tanghetti, Emil

    2015-12-01

    More effective therapies are needed in the specific treatment of severe inflammatory acne vulgaris. To demonstrate superior efficacy of adapalene 0.3%-benzoyl peroxide 2.5% gel (0.3% A/BPO) vs. vehicle, and to assess efficacy of 0.3% A/BPO vs. 0.1% A/BPO in subjects with severe inflammatory acne (Investigator's Global Assessment [IGA] of 4) in the context of a larger trial in a moderate and severe population. This was a multicenter, randomized, double-blind, parallel-group, 12-week study. Subjects were randomized to receive 0.3% A/BPO, 0.1% A/BPO (benchmark) or vehicle (comparator) once daily for 12 weeks. Co-primary efficacy endpoints were success rate at week 12 (percentage of subjects rated "clear" or "almost clear," ≥ 3-grade IGA improvement), and change in inflammatory (IN) and noninflammatory (NIN) lesion counts from baseline to week 12. Secondary efficacy endpoints were percent changes in IN and NIN lesion counts. Safety endpoints were incidence of adverse events (AEs) and local tolerability signs/symptoms. In the severe inflammatory acne population, a total of 252 subjects were randomized with 106, 112 and 34 subjects in the 0.3% A/BPO, 0.1% A/BPO and vehicle groups, respectively, reaching a high rate of study completion (88.5%). At week 12, both 0.3% A/BPO and 0.1% A/BPO were superior to vehicle in terms of lesion count reduction. However for success rate, only 0.3% A/BPO achieved significantly greater efficacy over vehicle with a treatment difference of 20.1% (31.9% vs. 11.8%; 95% Confidence Interval (CI): [6.0%, 34.2%], P=.029), whereas 0.1% A/BPO did not (treatment difference vs. vehicle of 8.8%; P=.443). This translates to an 11% difference between active treatments in favor of 0.3% A/BPO. Also, 0.3% A/BPO was safe and well tolerated. Availability of this new treatment option should allow clinicians to better customize severe inflammatory acne management, and the high-strength product provides a step-up treatment when needed.

  17. Safety and efficacy of adapalene 0.1% / benzoyl peroxide 2.5% in the long-term treatment of predominantly moderate acne with or without concomitant medication - results from the non-interventional cohort study ELANG.

    PubMed

    Gollnick, H P M; Friedrich, M; Peschen, M; Pettker, R; Pier, A; Streit, V; Jöstingmeyer, P; Porombka, D; Rojo Pulido, I; Jäckel, A

    2015-06-01

    Acne is a chronic inflammatory disease requiring long-term treatment. The fixed-dose combination adapalene 0.1%/benzoyl peroxide 2.5% (adapalene-BPO) is indicated for the once-daily topical treatment of Acne vulgaris when comedones, papules and pustules are present. The main objectives of this non-interventional study were to assess long-term efficacy and safety of adapalene-BPO in moderate to severe acne with and without concomitant medication. Patients with moderate to severe acne received adapalene-BPO alone or in combination with concomitant medication over a course of 9 months. The primary efficacy endpoint was changes in acne severity according to the Leeds Revised Acne Grading System; secondary endpoints included treatment success assessed by the patient and safety. In total, 5131 patients were eligible for efficacy and 5141 for safety evaluation. The majority of patients (78.8%) received adapalene-BPO alone. About 21.2% received adapalene-BPO in combination with another agent, mostly topical antibiotics (8.8%) or systemic antibiotics (8.7%). Mean (±SD) acne severity improved from 5.6 ± 1.5 at baseline to 3.3 ± 1.9 at month 3, and further to 1.9 ± 1.9 at month 9 (both P < 0.0001). The degree of improvement correlated significantly with the severity at baseline. After 3 and 9 months of treatment, the facial skin was cleared completely (no more visible acne lesions) in 420 (8.2%) and 1326 patients (25.8%), respectively. A therapeutic effect was noted by the patients after a median time of 3 weeks (range: from 1 day to 12 weeks). No serious adverse events were reported. Facial skin irritations, mostly mild to moderate, occurred in 49.5% of patients and led to discontinuation in only 1.7% of cases. In consistence with previous clinical findings, the use of adapalene-BPO in daily practice routine is safe and effective in the long-term management of patients with moderate to severe acne. © 2015 European Academy of Dermatology and Venereology.

  18. A multicentre, randomized, single-blind, parallel-group study comparing the efficacy and tolerability of benzoyl peroxide 3%/clindamycin 1% with azelaic acid 20% in the topical treatment of mild-to-moderate acne vulgaris.

    PubMed

    Schaller, M; Sebastian, M; Ress, C; Seidel, D; Hennig, M

    2016-06-01

    Mild-to-moderate acne vulgaris is treated with a range of mono- and combination therapies; however, clinical evidence is still required to optimize treatment recommendations. To compare the efficacy, tolerability and safety of a combination of benzoyl peroxide 3% and clindamycin 1% (BPO + CLN) with azelaic acid 20% (AzA) for the topical treatment of mild-to-moderate acne vulgaris. This was a randomized, assessor-blinded, parallel-group, multicentre study conducted in Germany. Patients with a confirmed diagnosis of acne vulgaris, aged 12-45 years, were randomized 1 : 1 to once-daily BPO + CLN gel or twice-daily AzA cream for up to 12 weeks. The primary endpoint was the percentage change in inflammatory lesions from baseline at Week 4. Secondary endpoints included total and inflammatory lesion counts and tolerability assessments. For selected secondary endpoints, inductive statistical analysis was performed post hoc. Patient safety was assessed by adverse event (AE) monitoring. Efficacy was assessed in the modified intent-to-treat (mITT) population [patients using ≥1 dose of study medication (ITT), plus baseline and ≥1 post-baseline lesion count (n = 215)]. There was a statistically significant difference in the primary endpoint, with a median decrease of -52.6% for BPO + CLN (n = 107) vs.-38.8% for AzA (n = 108; P = 0.0004). There was also a greater difference in secondary lesion endpoints at Week 12, with a median decrease in inflammatory lesions of -78.8% and -65.3% and total lesions of -69.0% and -53.9% with BPO + CLN and AzA, respectively (both P < 0.0001). Tolerability was acceptable for both treatments. Overall, 55.6% (BPO + CLN) and 69.7% (AzA) of patients reported treatment-emergent AEs, and 15.7% and 35.8% of patients experienced application site reactions with BPO + CLN (24 events; 17 patients) and AzA (60 events; 39 patients) treatment, respectively (ITT population). BPO + CLN demonstrated greater efficacy than AzA in the treatment of mild

  19. Kinetics of the hydrolysis of N-benzoyl-l-serine methyl ester catalysed by bromelain and by papain. Analysis of modifier mechanisms by lattice nomography, computational methods of parameter evaluation for substrate-activated catalyses and consequences of postulated non-productive binding in bromelain- and papain-catalysed hydrolyses

    PubMed Central

    Wharton, Christopher W.; Cornish-Bowden, Athel; Brocklehurst, Keith; Crook, Eric M.

    1974-01-01

    1. N-Benzoyl-l-serine methyl ester was synthesized and evaluated as a substrate for bromelain (EC 3.4.22.4) and for papain (EC 3.4.22.2). 2. For the bromelain-catalysed hydrolysis at pH7.0, plots of [S0]/vi (initial substrate concn./initial velocity) versus [S0] are markedly curved, concave downwards. 3. Analysis by lattice nomography of a modifier kinetic mechanism in which the modifier is substrate reveals that concave-down [S0]/vi versus [S0] plots can arise when the ratio of the rate constants that characterize the breakdown of the binary (ES) and ternary (SES) complexes is either less than or greater than 1. In the latter case, there are severe restrictions on the values that may be taken by the ratio of the dissociation constants of the productive and non-productive binary complexes. 4. Concave-down [S0]/vi versus [S0] plots cannot arise from compulsory substrate activation. 5. Computational methods, based on function minimization, for determination of the apparent parameters that characterize a non-compulsory substrate-activated catalysis are described. 6. In an attempt to interpret the catalysis by bromelain of the hydrolysis of N-benzoyl-l-serine methyl ester in terms of substrate activation, the general substrate-activation model was simplified to one in which only one binary ES complex (that which gives rise directly to products) can form. 7. In terms of this model, the bromelain-catalysed hydrolysis of N-benzoyl-l-serine methyl ester at pH7.0, I=0.1 and 25°C is characterized by Km1 (the dissociation constant of ES)=1.22±0.73mm, k (the rate constant for the breakdown of ES to E+products, P)=1.57×10−2±0.32×10−2s−1, Ka2 (the dissociation constant that characterizes the breakdown of SES to ES and S)=0.38±0.06m, and k′ (the rate constant for the breakdown of SES to E+P+S)=0.45±0.04s−1. 8. These parameters are compared with those in the literature that characterize the bromelain-catalysed hydrolysis of α-N-benzoyl-l-arginine ethyl ester and

  20. Formation of a dinuclear copper(II) complex through the cleavage of CN bond of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole

    SciTech Connect

    Shardin, Rosidah; Pui, Law Kung; Yamin, Bohari M.; Kassim, Mohammad B.

    2014-09-03

    A simple mononuclear octahedral copper(II) complex was attempted from the reaction of three moles of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole and one mole of copper(II) perchlorate hexahydrate in methanol. However, the product of the reaction was confirmed to be a dinuclear copper(II) complex with μ-(3-(pyridin-2-yl)-pyrazolato) and 3-(pyridin-2-yl)-1H-pyrazole ligands attached to each of the Cu(II) centre atom. The copper(II) ion assisted the cleavage of the C{sub benzoyl}N bond afforded a 3-(pyridin-2-yl)-1H-pyrazole molecule. Deprotonation of the 3-(pyridin-2-yl)-1H-pyrazole gave a 3-(pyridin-2-yl)-pyrazolato, which subsequently reacted with the Cu(II) ion to give the (3-(pyridin-2-yl)-pyrazolato)(3-(pyridin-2-yl)-1H-pyrazole)Cu(II) product moiety. The structure of the dinuclear complex was confirmed by x-ray crystallography. The complex crystallized in a monoclinic crystal system with P2(1)/n space group and cell dimensions of a = 12.2029(8) Å, b = 11.4010(7) Å, c = 14.4052(9) Å and β = 102.414(2)°. The compound was further characterized by mass spectrometry, CHN elemental analysis, infrared and UV-visible spectroscopy and the results concurred with the x-ray structure. The presence of d-d transition at 671 nm (ε = 116 dm{sup 3} mol{sup −1} cm{sup −1}) supports the presence of Cu(II) centres.

  1. Synthesis, structure, and reactivity of N-benzoyl iminophosphoranes ortho lithiated at the benzoyl group.

    PubMed

    Aguilar, David; Fernández, Ignacio; Cuesta, Luciano; Yañez-Rodríguez, Víctor; Soler, Tatiana; Navarro, Rafael; Urriolabeitia, Esteban P; López Ortiz, Fernando

    2010-10-01

    Ortho lithiation of N-benzamido-P,P,P-triaryliminophosphoranes through deprotonation with alkyllithium bases was achieved with ortho-C═O and ortho-P═N chemoselectivity. However, the synthetic scope of these processes was rather limited. Ortho-lithiated N-benzamido-P,P,P-triphenyliminophosphorane 8 was efficiently prepared via lithium/halogen exchange of the corresponding ortho-brominated precursor with s-BuLi in THF at -90 °C. The reaction of 8 with a variety of electrophiles provides an easy and mild method for the regioselective synthesis of ortho-modified iminophosphoranes via C-C (alkylation and hydroxyalkylation) and C-X (X = I, Si, P, Sn, and Hg) bond-forming reactions. NMR characterization of 8 in THF solution showed that 8 exists as an equilibrium mixture of one monomer and two dimers. The Li atoms of these species become members of five-membered rings through chelation by the ortho-metalated carbon and the carbonyl oxygen. The dimers differ in the relative orientation of the two chelates with respect to the plane defined by the C(2)Li(2) core. The equilibrium between all species is established by splitting the dimers into monomers and subsequent recombination with formation of a different dimer.

  2. A novel one-pot synthesis of heterocyclic compound (4-benzoyl-5-phenyl-2-(pyridin-2-yl)-3,3a-dihydropyrazolo[1,5-c]pyrimidin-7(6H)-one): Structural (X-ray and DFT) and spectroscopic (FT-IR, NMR, UV-Vis and Mass) characterization Studies

    NASA Astrophysics Data System (ADS)

    Özdemir, Mecit; Sönmez, Mehmet; Şen, Fatih; Dinçer, Muharrem; Özdemir, Namık

    2015-02-01

    In this study, the title compound named as 4-benzoyl-5-phenyl-2-(pyridin-2-yl)-3,3a-dihydropyrazolo[1,5-c]pyrimidin-7(6H)-one (C24H18N4O2) was both experimentally and theoretically investigated. The compound was synthesized and characterized by FT-IR, NMR (1H NMR, 13C NMR and HETCOR-NMR), Mass spectroscopies and single-crystal X-ray diffraction methods. The compound crystallizes in the monoclinic space group P21/n with a = 6.1402 (3) Å, b = 21.4470 (15) Å, c = 15.0049 (8) Å and β = 97.407 (4)°. The molecular geometry was obtained from the X-ray structure determination optimized using density functional theory (DFT/B3LYP) method with the 6-31+G(d, p) basis set in ground state. From the optimized structure, geometric parameters, vibrational wavenumbers and chemical shifts of molecule were obtained. Experimental measurements were compared with its corresponding the calculated data. An excellent harmony between the two data was ascertained. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs) and non-linear optical (NLO) properties of the title molecule were investigated by theoretical calculations at the B3LYP/6-31+G(d, p) level.

  3. Development and Binding Mode Assessment of N-[4-[2-propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-L-γ-glutamyl-D-glutamic acid (BGC 945), a Novel Thymidylate Synthase Inhibitor that Targets Tumor Cells

    PubMed Central

    Tochowicz, Anna; Dalziel, Sean; Eidam, Oliv; O’Connell, Joseph D.; Griner, Sarah; Finer-Moore, Janet S.; Stroud, Robert M.

    2013-01-01

    N-[4-[2-propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-L-γ-glutamyl-D-glutamic acid 1 (BGC 945, now known as ONX 0801), is a small molecule thymidylate synthase (TS) inhibitor discovered at the Institute of Cancer Research in London. It is licensed by Onyx Pharmaceuticals and is in Phase 1 clinical studies. It is a novel antifolate drug resembling TS inhibitors plevitrexed and raltitrexed that combines enzymatic inhibition of thymidylate synthase with α-folate receptor-mediated targeting of tumor cells. Thus, it has potential for efficacy with lower toxicity due to selective intracellular accumulation through α-folate receptor (α-FR) transport. The α-FR, a cell-surface receptor glycoprotein, which is over expressed mainly in ovarian and lung cancer tumors, has an affinity for 1 similar to that for its natural ligand, folic acid. This study describes a novel synthesis of 1, an X-ray crystal structure of its complex with Escherichia coli TS and 2’-deoxyuridine-5’-monophosphate, and a model for a similar complex with human TS. PMID:23710599

  4. Structural, spectral, thermal and biological studies on (Z)-N-benzoyl-N‧-(2-oxo-2-(phenylamino)acetyl)carbamohydrazonothioic acid (H2PABT) and its Cd(II), Hg(II), Zn(II) and U(VI)O22+ complexes

    NASA Astrophysics Data System (ADS)

    Yousef, T. A.; Ahmed, Sara F.; El-Gammal, O. A.; Abu El-Reash, G. M.

    2015-07-01

    A new metal complexes formed by the reaction of (Z)-N-benzoyl-N‧-(2-oxo-2-(phenylamino)acetyl)carbamohydrazonothioic acid (H2PABT) and Cd(II), Hg(II), Zn(II) and U(VI)O22+ ions. The isolated complexes were prepared and characterized by conventional techniques. The IR data revealed that the ligand behaves as mononegative tridentate in Zn(II) and U(VI)O22+ complexes also, binegative tetradentate on Cd(II) and Hg(II) complexes. On the basis of magnetic and electronic spectral data an octahedral geometry for the U(VI)O22+ complex, a tetrahedral structure for the Cd(II), Zn(II) and Hg(II) complexes have been proposed. The IR spectrum of ligand which determined experimentally is compared with those obtained theoretically from DFT calculations. Also, the bond lengths, bond angles, HOMO, LUMO and dipole moments have been calculated. The calculated HOMO-LUMO energy gap reveals that charge transfer occurs within the ligand molecules. The calculated values of binding energies indicates the stability of complexes is higher that of ligand. Also, the kinetic and thermodynamic parameters for the different thermal degradation steps of the complexes were determined by Coats-Redfern and Horowitz-Metzger methods. Moreover, the ligand and its complexes were screened against Bacillus subtilis as Gram positive bacteria and Escherichia coli Gram negative bacteria using the inhibitory zone diameter. Also the antitumor activities of the ligand and its complexes have been evaluated against liver (HePG2) and breast (MCF-7) cancer cells. Out of all the synthesized compounds, [Hg2(PABT)Cl2(H2O)2] and [(UO2)(HPABT)(OAc)(H2O)] complexes showed high antibacterial activity with 55.5% while H2PABT showed the best cytotoxic effect on liver and breast cancer cells with IC50 2.10 and 5.91 of cytotoxicity respectively.

  5. Anti-diabetic and anti-adipogenic effects of a novel selective 11β-hydroxysteroid dehydrogenase type 1 inhibitor, 2-(3-benzoyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-2-yl-1-phenylethanone (KR-66344).

    PubMed

    Park, Ji Seon; Rhee, Sang Dal; Kang, Nam Sook; Jung, Won Hoon; Kim, Hee Youn; Kim, Jun Hyoung; Kang, Seung Kyu; Cheon, Hyae Gyeong; Ahn, Jin Hee; Kim, Ki Young

    2011-04-15

    The selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) have considerable potential for treating type 2 diabetes mellitus and metabolic syndrome. In the present study, we investigated the anti-diabetic and anti-adipogenic effects of 2-(3-benzoyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-2-yl-1-phenylethanone (KR-66344), as a 11β-HSD1 inhibitor; we also investigated the underlying molecular mechanisms in the cortisone-induced 3T3-L1 adipogenesis model system and C57BL/6-Lep(ob/ob) mice. KR-66344 concentration-dependently inhibited 11β-HSD1 activity in human liver microsome, mouse C2C12 myotube and human SW982 cells. In the C57BL/6-Lep(ob/ob) mice study, the administration of KR-66344 (200mg/kg/d, orally for 5 days) improved the glucose intolerance as determined by the oral glucose tolerance test, in which the area under the curve (AUC) of the plasma glucose concentration was significantly reduced by 27% compared with the vehicle treated group. Further, KR-66344 suppressed adipocyte differentiation on cortisone-induced adipogenesis in 3T3-L1 cells is associated with the suppression of the cortisone-induced mRNA levels of FABP4, G3PD, PPARγ2 and Glut4, and 11β-HSD1 expression and activity. Our results additionally demonstrate evidence showing that KR-66344 improved glycemic control and inhibited adipogenesis via 11β-HSD1 enzyme activity. Taken together, these results may provide evidence of the therapeutic potential of KR-66344, as a 11β-HSD1 inhibitor, in obesity and type 2 diabetes patients with metabolic syndrome. Copyright © 2011 Elsevier Inc. All rights reserved.

  6. Formation of a dinuclear copper(II) complex through the cleavage of CN bond of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole

    NASA Astrophysics Data System (ADS)

    Shardin, Rosidah; Pui, Law Kung; Yamin, Bohari M.; Kassim, Mohammad B.

    2014-09-01

    A simple mononuclear octahedral copper(II) complex was attempted from the reaction of three moles of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole and one mole of copper(II) perchlorate hexahydrate in methanol. However, the product of the reaction was confirmed to be a dinuclear copper(II) complex with μ-{3-(pyridin-2-yl)-pyrazolato} and 3-(pyridin-2-yl)-1H-pyrazole ligands attached to each of the Cu(II) centre atom. The copper(II) ion assisted the cleavage of the CbenzoylN bond afforded a 3-(pyridin-2-yl)-1H-pyrazole molecule. Deprotonation of the 3-(pyridin-2-yl)-1H-pyrazole gave a 3-(pyridin-2-yl)-pyrazolato, which subsequently reacted with the Cu(II) ion to give the {3-(pyridin-2-yl)-pyrazolato}{3-(pyridin-2-yl)-1H-pyrazole}Cu(II) product moiety. The structure of the dinuclear complex was confirmed by x-ray crystallography. The complex crystallized in a monoclinic crystal system with P2(1)/n space group and cell dimensions of a = 12.2029(8) Å, b = 11.4010(7) Å, c = 14.4052(9) Å and β = 102.414(2)°. The compound was further characterized by mass spectrometry, CHN elemental analysis, infrared and UV-visible spectroscopy and the results concurred with the x-ray structure. The presence of d-d transition at 671 nm (ɛ = 116 dm3 mol-1 cm-1) supports the presence of Cu(II) centres.

  7. Clindamycin phosphate 1·2%-benzoyl peroxide 3·0% fixed-dose combination gel has an effective and acceptable safety and tolerability profile for the treatment of acne vulgaris in Japanese patients: a phase III, multicentre, randomised, single-blinded, active-controlled, parallel-group study.

    PubMed

    Kawashima, M; Hashimoto, H; Alió Sáenz, A B; Ono, M; Yamada, M

    2015-02-01

    A topical fixed-dose clindamycin phosphate 1·2% and benzoyl peroxide 3·0% combination gel (CLNP/BPO 3%) is known to be effective and safe in white people with acne. To evaluate the efficacy and safety of CLNP/BPO 3·0% topically applied once or twice daily vs. CLNP twice daily in Japanese patients with acne. Eight hundred patients were randomized to receive CLNP/BPO 3·0% once daily, CLNP/BPO 3·0% twice daily or CLNP twice daily for 12 weeks. Primary endpoints were absolute change in number of total lesions (TLs) from baseline to week 12 to demonstrate the superiority of CLNP/BPO 3·0% twice daily and noninferiority of CLNP/BPO 3·0% once daily vs. CLNP twice daily. Secondary endpoints were absolute and percentage changes in TLs, inflammatory lesions (ILs), noninflammatory lesions (non-ILs) and Investigator's Static Global Assessment (ISGA) score. Safety assessments included adverse events (AEs), laboratory tests, vital signs and local skin tolerability. Change in TL counts from baseline to week 12 for CLNP/BPO 3·0% twice daily was superior to CLNP twice daily (difference -11·0; P < 0·01); CLNP/BPO 3·0% once daily was not inferior to CLNP twice daily (difference -10·3; P < 0·01). Absolute and percentage reductions in TL, IL and non-IL counts and ISGA score were greater for CLNP/BPO 3·0% once or twice daily than for CLNP twice daily with significant differences seen from early on. Most AEs were mild or moderate. The incidence of adverse drug reactions was higher for CLNP/BPO 3·0% once (24·0%) or twice (35·1%) daily than for CLNP twice daily (9·0%). Compared with CLNP twice daily, CLNP/BPO 3·0% once daily was more effective and CLNP/BPO 3·0% twice daily at least as effective, with an early onset of action and an acceptable safety and tolerability profile in Japanese patients. © 2014 British Association of Dermatologists.

  8. Effect of adapalene 0.1%/benzoyl peroxide 2.5% topical gel on quality of life and treatment adherence during long-term application in patients with predominantly moderate acne with or without concomitant medication - additional results from the non-interventional cohort study ELANG.

    PubMed

    Gollnick, H P M; Friedrich, M; Peschen, M; Pettker, R; Pier, A; Streit, V; Jöstingmeyer, P; Porombka, D; Rojo Pulido, I; Jäckel, A

    2015-06-01

    In addition to physical long-lasting effects such as permanent scarring and disfigurement, acne has acute and long-term psychosocial effects that affect the individual's quality of life. As with other chronic diseases, treatment success is often compromised by poor adherence. Two main objectives of this non-interventional study were to assess the long-term effect of the fixed-dose combination adapalene 0.1%/benzoyl peroxide 2.5% (adapalene-BPO gel) on quality of life and treatment adherence. Patients with moderate to severe facial acne receiving adapalene-BPO alone or in combination with other drugs were enrolled in this non-interventional study. Data were documented at baseline and after 3 and 9 months of adapalene-BPO treatment. The secondary outcomes reported here include quality of life determined by the Cardiff Acne Disability Index (CADI), treatment adherence assessed by the ECOB (Elaboration d'un outil d'evaluation de l'observance des traitements medicamenteux) questionnaire, and patient satisfaction. In total, 5131 patients were included in the efficacy evaluation. After 9 months, mean (±SD) quality of life (CADI) improved significantly from 5.9 ± 3.0 to 2.4 ± 2.7 (P < 0.0001). Patients with more severe acne at baseline tended to achieve a greater improvement in quality of life. Long-term adherence was found to be good in 83.9% of patients. Adherence had a significant effect on efficacy and quality of life (P < 0.0001 respectively). The vast majority of patients (92.1%) reported subjective improvement at the interim analysis. Accordingly, most patients (84.8%) were satisfied or very satisfied with adapalene-BPO by the end of the observation period. The clinical improvement of the disease led to an increase in quality of life among acne patients. The treatment success may be a motivation factor for patients to stay adherent over the long-term treatment course, indicating the qualification of adapalene-BPO topical gel as an appropriate medication also in

  9. N-Benzoyl-3-nitro-benzene-sulfonamide.

    PubMed

    Suchetan, P A; Foro, Sabine; Gowda, B Thimme

    2011-12-01

    In the title compound, C(13)H(10)N(2)O(5)S, the dihedral angle between the phenyl and benzene rings is 86.7 (1)°. In the crystal, mol-ecules are linked into zigzag C(4) chains running along the b axis via N-H⋯O hydrogen bonds.

  10. N-Benzoyl-N′,N′-dimethyl­thio­urea

    PubMed Central

    Pérez, Hiram; Corrêa, Rodrigo S.; Plutín, Ana María; Álvarez, Anislay; Mascarenhas, Yvonne

    2011-01-01

    In the title compound, C10H12N2OS, the amide NCO group is twisted relative to the thio­ureido SCN2 group, forming a dihedral angle of 55.3 (2)°. The crystal packing shows inter­molecular N—H⋯S and weak C—H⋯O inter­actions, the former giving rise to the formation of centrosymmetric R 2 2(8) dimers. PMID:21522399

  11. 9-Benzoyl 9-deazaguanines as potent xanthine oxidase inhibitors.

    PubMed

    Rodrigues, Marili V N; Barbosa, Alexandre F; da Silva, Júlia F; dos Santos, Deborah A; Vanzolini, Kenia L; de Moraes, Marcela C; Corrêa, Arlene G; Cass, Quezia B

    2016-01-15

    A novel potent xanthine oxidase inhibitor, 3-nitrobenzoyl 9-deazaguanine (LSPN451), was selected from a series of 10 synthetic derivatives. The enzymatic assays were carried out using an on-flow bidimensional liquid chromatography (2D LC) system, which allowed the screening¸ the measurement of the kinetic inhibition constant and the characterization of the inhibition mode. This compound showed a non-competitive inhibition mechanism with more affinity for the enzyme-substrate complex than for the free enzyme, and inhibition constant of 55.1±9.80 nM, about thirty times more potent than allopurinol. Further details of synthesis and enzymatic studies are presented herein.

  12. N-[[(Mercaptoacetyl)amino]benzoyl]glycines as mucolytic agents.

    PubMed

    Martin, T A; Comer, W T

    1985-07-01

    m- and p-aminobenzoic acids were converted to the title compounds by sequential use of ClCH2COCl, SOCl2, glycine methyl or ethyl ester, AcSK, and hydrolysis. The title compounds and a number of salts were compared for mucolytic activity, toxicity, stability, and hygroscopicity. When compared to N-acetyl-L-cysteine (NAC), the compounds exhibit several times the in vitro mucolytic activity of NAC on a molar basis. The most promising candidate appears to be the sodium salt 3.5H2O 2 of the meta series.

  13. Moderate and Severe Inflammatory Acne Vulgaris Effectively Treated with Single-Agent Therapy by a New Fixed-Dose Combination Adapalene 0.3 %/Benzoyl Peroxide 2.5 % Gel: A Randomized, Double-Blind, Parallel-Group, Controlled Study.

    PubMed

    Stein Gold, Linda; Weiss, Jonathan; Rueda, Maria Jose; Liu, Hong; Tanghetti, Emil

    2016-06-01

    A need exists for topical treatments in managing more severe inflammatory acne. The objectives of this study were to evaluate the efficacy and safety of adapalene 0.3 %/benzoyl peroxide 2.5 % (0.3 % A/BPO) topical gel in subjects with moderate and severe inflammatory acne. This was a multicenter, randomized, double-blind, parallel-group study. Randomization was stratified by acne severity (50 % moderate and 50 % severe). Subjects received 0.3 % A/BPO, 0.1 % A/BPO (benchmark), or vehicle (comparator) once daily for 12 weeks. Co-primary efficacy endpoints were success rate at week 12 (the percentage of subjects rated 'clear' or 'almost clear' with at least a 2-grade improvement on Investigator's Global Assessment [IGA]) and change in inflammatory (IN) and noninflammatory (NIN) lesion counts from baseline to week 12. Secondary efficacy endpoints were percent changes in IN and NIN lesion counts. Safety endpoints were incidence of adverse events (AEs) and local tolerability signs/symptoms. A total of 503 subjects were randomized: 217, 217, and 69 subjects in the 0.3 % A/BPO, 0.1 % A/BPO, and vehicle groups, respectively. For success rate (subjects rated 'clear' or 'almost clear' with ≥2-grade improvement in IGA), 0.3 % A/BPO was superior to vehicle, with a treatment difference of 22.7 % (33.7 vs. 11.0 %; 95 % confidence interval [CI] 12.8-32.6, p < 0.001). At week 12, 0.3 % A/BPO was superior to vehicle for mean reduction from baseline in IN (27.0 vs. 14.4) and NIN lesion counts (40.2 vs. 18.5), as well as for percentage reduction from baseline in IN (68.7 vs. 39.2 %) and NIN lesion counts (68.3 vs. 37.4 %) (all p < 0.001). Among subjects with severe inflammatory acne (IGA = 4), 0.1 % A/BPO did not reach statistical significance for success rate compared with vehicle (p = 0.443), whereas 0.3 % A/BPO demonstrated significantly greater efficacy (p = 0.029, requiring ≥3-point IGA improvement). Additionally, 0.3 % A/BPO was safe and well

  14. Absorption spectroscopic study of synergistic extraction of praseodymium with benzoyl acetone in presence of crown ether.

    PubMed

    Banerjee, Shrabanti; Bhattacharya, Sumanta; Basu, Sukalyan

    2005-04-01

    The extraction behaviour of Pr(III) from aqueous nitric acid medium employing benzoylacetone has been studied in presence of two crown ethers, viz., 15-crown-5 and benzo-15-crown-5 in chloroform medium using UV-vis absorption spectroscopy. The binary equilibrium constant (logk(ex)) for the complex [Pr(benzoylacetonate)(NO3(-))2(H(2)O)] in organic phase was found to be 1.170. The overall equilibrium constants (logK) for the ternary species [Pr(benzoylacetonate)(crown ether)(NO3(-))(2)] were estimated to be 4.01 and 4.41 for 15-crown-5 and benzo-15-crown-5, respectively. The trend in the equilibrium constant values were very much in accordance with the nature of substitution of the donor moiety. The extraction of Pr(III) by the benzoylacetone-crown ether combination was maximum at pH 3.0 and extraction decreases with increase in pH. It has been found that the extent of extraction of Pr(III) in organic phase as the binary as well as ternary complex [Pr(benzoylacetonate)(NO3(-))(2)(H(2)O)] and [Pr(benzoylacetonate)(crown ether)(NO3(-))(2)] increases with increase in concentration of the ligand. Similar trend is observed in the extraction by only donors. Enthalpies and entropies of formation for the ternary extraction process have been estimated. In addition, the effect of NaNO(3) as foreign salt was also studied and it was observed that with increase in ionic strength, percentage extraction increases.

  15. Copper-mediated electrophilic imination of alkenylzirconocenes with O-benzoyl ketoximes and aldoximes.

    PubMed

    Liu, Hailan; Yan, Xiaoyu; Chen, Chao; Liu, Qingbin; Xi, Chanjuan

    2013-06-18

    Copper-mediated electrophilic imination of alkenylzirconocenes generated in situ from alkynes and zirconocenes is accomplished under mild reaction conditions. The reaction can be used to prepare various 2-azadienes.

  16. /sup 35/Cl NQR spectra of complexes of tetrachlorostannane with substituted benzoyl chlorides

    SciTech Connect

    Feshin, V.P.; Dogushin, G.V.; Lazarev, I.M.; Voronkov, M.G.; Feshina, E.V.

    1987-05-01

    /sup 35/Cl NQR spectra of mixtures of SnCl/sub 4/ with 2-, 3- and 4-XC/sub 6/H/sub 4/COCl were obtained. The electronic and steric structure of the complexes obtained was established. Their formation and structure depend on the nature of substituents X. Complexes with a trigonal-bipyramidal structure are formed with the participation of the carbonyl oxygen atom of the ligand as an electron-donor-center, and complexes with trans-octahedral structure, with the participation of the sulfur atom of the X = CH/sub 3/S substituent.

  17. Surface chemistry of benzoyl compounds on oxides, an FT-IR study

    SciTech Connect

    Koutstaal, C.A.; Angevaare, P.A.J.M.; Ponec, V. )

    1993-10-01

    Adsorption and surface reactions on various oxides have been monitored by IR spectroscopy, with benzaldehyde, benzoic acid, methylphenylketone, and 2-phenyl-2-propanol. The oxides were chosen to represent typical adsorption properties (SiO[sub 2], [gamma]-Al[sub 2]O[sub 3], and [alpha]-Mn[sub 3]O[sub 4]). Surface reactions were observed at various temperatures, starting from room temperature. The results concern three points: (i) identification of adsorbed species, arising on different oxides under increasing temperatures; (ii) the possible sequence of reaction steps in the insertion (oxidation) or removal (reduction) of oxygen, into or from the molecules studied; and (iii) the conclusion that a Cannizzaro reaction is not likely so that the insertion (and removal) is most probably by the Mars and van Krevelen mechanism. 17 refs., 10 figs., 1 tab.

  18. Ethyl N-(2-benzoyl-3-oxo-3-phenyl-propano-yl)carbamate.

    PubMed

    Akkurt, Mehmet; Sarıoğlu, Ahmet Oral; Sönmez, Mehmet; Tahir, Muhammad Nawaz

    2013-02-01

    In the title compound, C(19)H(17)NO(5), the dihedral angle between the phenyl groups is 79.55 (15)°. The terminal eth-oxy group is disordered over two orientations in a 0.873 (6):0.127 (6) ratio. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into [001] chains which incorporate R(1) (2)(6) loops. A very weak C-H⋯π contact also occurs.

  19. Ethyl N-(2-benzoyl-3-oxo-3-phenyl­propano­yl)carbamate

    PubMed Central

    Akkurt, Mehmet; Sarıoğlu, Ahmet Oral; Sönmez, Mehmet; Tahir, Muhammad Nawaz

    2013-01-01

    In the title compound, C19H17NO5, the dihedral angle between the phenyl groups is 79.55 (15)°. The terminal eth­oxy group is disordered over two orientations in a 0.873 (6):0.127 (6) ratio. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into [001] chains which incorporate R 1 2(6) loops. A very weak C—H⋯π contact also occurs. PMID:23424501

  20. A new silver nanorod SPR probe for detection of trace benzoyl peroxide

    NASA Astrophysics Data System (ADS)

    Jiang, Zhiliang; Wen, Guiqing; Luo, Yanghe; Zhang, Xinghui; Liu, Qingye; Liang, Aihui

    2014-06-01

    The stable silver nanorod (AgNR) sol in red was prepared by the two-step procedure of NaBH4-H2O2 and citrate heating reduction. The AgNR had a transverse and a longitudinal surface plasmon resonance (SPR) absorption peak at 338 nm and 480 nm. Meanwhile, two transverse and longitudinal SPR Rayleigh scattering (SPR-RS) peaks at 340 nm and 500 nm were observed firstly using common fluorescence spectrometer. The SPR absorption, RS, surface enhanced Raman scattering (SERS) and electron microscope technology were used to study the formation mechanism of red silver nanorods and the SERS enhancement mechanism of nano-aggregation. The AgNR-BPO SPR absorption and AgNR-NaCl-BPO SPR-RS analytical systems were studied to develop two new simple, rapid, and low-cost SPR methods for the detection of trace BPO.

  1. A new silver nanorod SPR probe for detection of trace benzoyl peroxide

    PubMed Central

    Jiang, Zhiliang; Wen, Guiqing; Luo, Yanghe; Zhang, Xinghui; Liu, Qingye; Liang, Aihui

    2014-01-01

    The stable silver nanorod (AgNR) sol in red was prepared by the two-step procedure of NaBH4-H2O2 and citrate heating reduction. The AgNR had a transverse and a longitudinal surface plasmon resonance (SPR) absorption peak at 338 nm and 480 nm. Meanwhile, two transverse and longitudinal SPR Rayleigh scattering (SPR-RS) peaks at 340 nm and 500 nm were observed firstly using common fluorescence spectrometer. The SPR absorption, RS, surface enhanced Raman scattering (SERS) and electron microscope technology were used to study the formation mechanism of red silver nanorods and the SERS enhancement mechanism of nano-aggregation. The AgNR-BPO SPR absorption and AgNR-NaCl-BPO SPR-RS analytical systems were studied to develop two new simple, rapid, and low-cost SPR methods for the detection of trace BPO. PMID:24937042

  2. Rapid determination and chemical change tracking of benzoyl peroxide in wheat flour by multi-step IR macro-fingerprinting

    NASA Astrophysics Data System (ADS)

    Guo, Xiao-Xi; Hu, Wei; Liu, Yuan; Sun, Su-Qin; Gu, Dong-Chen; He, Helen; Xu, Chang-Hua; Wang, Xi-Chang

    2016-02-01

    BPO is often added to wheat flour as flour improver, but its excessive use and edibility are receiving increasing concern. A multi-step IR macro-fingerprinting was employed to identify BPO in wheat flour and unveil its changes during storage. BPO contained in wheat flour (< 3.0 mg/kg) was difficult to be identified by infrared spectra with correlation coefficients between wheat flour and wheat flour samples contained BPO all close to 0.98. By applying second derivative spectroscopy, obvious differences among wheat flour and wheat flour contained BPO before and after storage in the range of 1500-1400 cm- 1 were disclosed. The peak of 1450 cm- 1 which belonged to BPO was blue shifted to 1453 cm- 1 (1455) which belonged to benzoic acid after one week of storage, indicating that BPO changed into benzoic acid after storage. Moreover, when using two-dimensional correlation infrared spectroscopy (2DCOS-IR) to track changes of BPO in wheat flour (0.05 mg/g) within one week, intensities of auto-peaks at 1781 cm- 1 and 669 cm- 1 which belonged to BPO and benzoic acid, respectively, were changing inversely, indicating that BPO was decomposed into benzoic acid. Moreover, another autopeak at 1767 cm- 1 which does not belong to benzoic acid was also rising simultaneously. By heating perturbation treatment of BPO in wheat flour based on 2DCOS-IR and spectral subtraction analysis, it was found that BPO in wheat flour not only decomposed into benzoic acid and benzoate, but also produced other deleterious substances, e.g., benzene. This study offers a promising method with minimum pretreatment and time-saving to identify BPO in wheat flour and its chemical products during storage in a holistic manner.

  3. Rapid determination and chemical change tracking of benzoyl peroxide in wheat flour by multi-step IR macro-fingerprinting.

    PubMed

    Guo, Xiao-Xi; Hu, Wei; Liu, Yuan; Sun, Su-Qin; Gu, Dong-Chen; He, Helen; Xu, Chang-Hua; Wang, Xi-Chang

    2016-02-05

    BPO is often added to wheat flour as flour improver, but its excessive use and edibility are receiving increasing concern. A multi-step IR macro-fingerprinting was employed to identify BPO in wheat flour and unveil its changes during storage. BPO contained in wheat flour (<3.0 mg/kg) was difficult to be identified by infrared spectra with correlation coefficients between wheat flour and wheat flour samples contained BPO all close to 0.98. By applying second derivative spectroscopy, obvious differences among wheat flour and wheat flour contained BPO before and after storage in the range of 1500-1400 cm(-1) were disclosed. The peak of 1450 cm(-1) which belonged to BPO was blue shifted to 1453 cm(-1) (1455) which belonged to benzoic acid after one week of storage, indicating that BPO changed into benzoic acid after storage. Moreover, when using two-dimensional correlation infrared spectroscopy (2DCOS-IR) to track changes of BPO in wheat flour (0.05 mg/g) within one week, intensities of auto-peaks at 1781 cm(-1) and 669 cm(-1) which belonged to BPO and benzoic acid, respectively, were changing inversely, indicating that BPO was decomposed into benzoic acid. Moreover, another autopeak at 1767 cm(-1) which does not belong to benzoic acid was also rising simultaneously. By heating perturbation treatment of BPO in wheat flour based on 2DCOS-IR and spectral subtraction analysis, it was found that BPO in wheat flour not only decomposed into benzoic acid and benzoate, but also produced other deleterious substances, e.g., benzene. This study offers a promising method with minimum pretreatment and time-saving to identify BPO in wheat flour and its chemical products during storage in a holistic manner.

  4. 75 FR 9767 - Classification of Benzoyl Peroxide as Safe and Effective and Revision of Labeling to Drug Facts...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-03-04

    .... Benefits of This Rule E. Alternatives and Steps Taken to Minimize Impacts on Small Entities F. Impact on... CFR part 314) OTC: Over-the-Counter--medicines sold without a prescription Panel: Advisory Review...). The study authors concluded that the past history of acne was the second strongest correlation to the...

  5. 4-Benzoyl-3,4-dihydro-2H-1,4-benzoxazine-2-carbonitrile: refinement using a multipolar atom model.

    PubMed

    Ejsmont, Krzysztof; Joly, Jean Pierre; Wenger, Emmanuel; Guillot, Benoit; Jelsch, Christian

    2009-07-01

    The structural model for the title compound, C(16)H(12)N(2)O(2), was refined using a multipolar atom model transferred from an experimental electron-density database. The refinement showed some improvements of crystallographic statistical indices when compared with a conventional spherical neutral-atom refinement. The title compound adopts a half-chair conformation. The amide N atom lies almost in the plane defined by the three neighbouring C atoms. In the crystal structure, molecules are linked by weak intermolecular C-H...O and C-H...pi hydrogen bonds.

  6. Bis(2-benzoyl-1-phenyl­ethenolato-κ2 O,O′)(ethanol-κO)dioxidouranium(VI)

    PubMed Central

    Takao, Koichiro; Ikeda, Yasuhisa

    2008-01-01

    In the title compound, [U(C15H11O2)2O2(C2H6O)], the UVI atom has a penta­gonal–bipyramidal coordination geometry. The two so-called ‘-yl’ O atoms occupy the axial positions whereas four O atoms from the two chelating dibenzoyl­methanate ligands and the O atom from the ethanol mol­ecule are situated in the equatorial plane. Inter­molecular hydrogen bonds between one of the ‘-yl’ O atoms and the ethanol OH group assemble mol­ecules into a centrosymmetric dimer. PMID:21200566

  7. 2-{2-[(E)-(2-Benzoyl-hydrazin-1-yl-idene)meth-yl]phen-oxy}acetic acid.

    PubMed

    Fun, Hoong-Kun; Chia, Tze Shyang; Alafeefy, Ahmed M; Abdel-Aziz, Hatem A

    2012-07-01

    In the title compound, C(16)H(14)N(2)O(4), the dihedral angle between the aromatic rings is 12.45 (6)°. The central C(=O)-N-N=C bridge is roughly planar (r.m.s. deviation = 0.0346 Å) and makes dihedral angles of 13.01 (7) and 0.56 (7)° with the attached phenyl and benzene rings, respectively. The acetic acid unit (r.m.s. deviation = 0.0066 Å) is twisted from its attached benzene ring [dihedral angle = 19.48 (6)°]. In the crystal, mol-ecules are linked by O-H⋯(O,N), N-H⋯O and C-H⋯O hydrogen bonds into sheets lying parallel to the bc plane. A weak aromatic π-π stacking inter-action is also observed [centroid-centroid distance = 3.7330 (7) Å].

  8. Adenosine-guanosine preferential photocleavage of DNA by azido-benzoyl- and diazocyclopenta-dienylcarbonyloxy derivatives of 9-aminoacridine.

    PubMed Central

    Nielsen, P E; Jeppesen, C; Egholm, M; Buchardt, O

    1988-01-01

    The photoreactions of 9-[6-(4-azidobenzamido)hexylamino]acridine (AHA) and 9-[6-(2-diazocyclopentadienylcarbonyloxy)hexylamino]acridine (DHA) with double stranded DNA result in formation of single strand nicks and alkali labile sites (adducts) with an efficiency of 6 x 10(-3) nicks per AHA and 3 x 10(-2) nicks per DHA molecule. The alkali dependent DNA cleavage by AHA shows a pronounced A+G preference whereas that by DHA is practically sequence independent. In the presence of diacridines, however, DHA exhibits a preference for cleavage at guanosines. These DNA photocleaving reagents could be useful for DNA photofootprinting and photosequencing. Images PMID:2836803

  9. Discovery of novel 2-aryl-4-benzoyl-imidazole (ABI-III) analogues targeting tubulin polymerization as antiproliferative agents.

    PubMed

    Chen, Jianjun; Ahn, Sunjoo; Wang, Jin; Lu, Yan; Dalton, James T; Miller, Duane D; Li, Wei

    2012-08-23

    Novel ABI-III compounds were designed and synthesized based on our previously reported ABI-I and ABI-II analogues. ABI-III compounds are highly potent against a panel of melanoma and prostate cancer cell lines, with the best compound having an average IC(50) value of 3.8 nM. They are not substrate of Pgp and thus may effectively overcome Pgp-mediated multidrug resistance. ABI-III analogues maintain their mechanisms of action by inhibition of tubulin polymerization.

  10. Teens and Acne Treatment

    MedlinePlus

    ... those zits under control. Types of treatments Benzoyl peroxide Benzoyl peroxide wash, lotion, or gel—the most effective acne ... wash or lotion first. How to use benzoyl peroxide Start slowly—only once a day with a ...

  11. 75 FR 67378 - Pediatric Advisory Committee; Notice of Meeting

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-11-02

    ... solution, Flovent HFA (fluticasone propionate), Acanya Gel (clindamycin/benzoyl peroxide combination), Epiduo Gel (adapalene and benzoyl peroxide), Ulesfia Lotion 5% (benzyl alcohol), Axert (almotriptan...

  12. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added...

  13. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added...

  14. 21 CFR 133.181 - Provolone cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... the cheese. (v) Benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is... weight of the benzoyl peroxide used. If milk is bleached in this manner, vitamin A is added to the...

  15. 21 CFR 133.195 - Swiss and emmentaler cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... cheese. (v) Benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is not more... benzoyl peroxide used. If milk is bleached in this manner, vitamin A is added to the curd in such...

  16. Effects of polar aprotic solvents on the rate of the topochemical reaction of benzoyl chloride with sodium azide in o-xylene

    SciTech Connect

    Zlobin, V.A.

    1985-10-01

    The kinetics of the topochemical reaction of benozyl chloride with sodium azide in o-xylene have been examined in the presence of varying amounts of acetonitrile and dimethylformamide. The specific rates and activation energies for the reaction have been found. These parameters have been found to increase with the amounts of polar aprotic solvent added. The observed dependence is explained by a change in the mechanism of the reaction.

  17. Grafting of 4-(2,4,6-Trimethylphenoxy)benzoyl onto Single-Walled Carbon Nanotubes in Poly(phosphoric acid) via Amide Function

    NASA Astrophysics Data System (ADS)

    Han, Sang-Wook; Oh, Se-Jin; Tan, Loon-Seng; Baek, Jong-Beom

    2009-07-01

    Single-walled carbon nanotubes (SWCNTs), which were commercial grade containing 60-70 wt% impurity, were treated in a mild poly(phosphoric acid) (PPA). The purity of PPA treated SWCNTs was greatly improved with or without little damage to SWCNTs framework and stable crystalline carbon particles. An amide model compound, 4-(2,4,6-trimethylphenoxy)benzamide (TMPBA), was reacted with SWCNTs in PPA with additional phosphorous pentoxide as “direct” Friedel-Crafts acylation reaction to afford TMPBA functionalized SWCNTs. All evidences obtained from Fourier-transform infrared spectroscopy, Raman spectroscopy, thermogravimetric analysis, scanning electron microcopy, and transmission electron microscopy strongly supported that the functionalization of SWCNTs with benzamide was indeed feasible.

  18. Structure and spectroscopic properties of ruthenium(II) bipyridyl N-benzoyl-N'-(1,10-phenanthrolin-5-Yl)-thiourea

    SciTech Connect

    Tan, Siew San; Kassim, Mohammad B.

    2015-09-25

    Ruthenium bipyridyl incorporating phenanthroline with thiourea molecules, [Ru(bpy){sub 2}(Phen-BT)](PF{sub 6}){sub 2}], has been synthesized and characterized by spectroscopic and electrochemical techniques. The infrared spectra of the complex shows the characteristics stretching frequencies for N-H at 3646 and 3585 cm{sup −1}, ν(C-N){sub phen} 1426 cm{sup −1}, ν(C=O) 1675 cm{sup −1}, ν(C=S) 1246 cm{sup −1}, ν(C-H){sub aromatic} 3353-3086 cm{sup −1}, ν(C-N){sub aliphatic} 1169-1026 cm{sup −1}, ν(C-H){sub bend} 764 cm{sup −1} and ν(PF{sub 6}{sup −}){sub free} 842 cm{sup −1}. The complex reveals two π→π* absorption bands at 237 (ε=26,302) and 286 nm (ε=36,848), which were assigned to the phenanthroline and bipyridyl moieties, respectively. A slightly broad and low energy band in the UV-vis spectrum at 450 nm (ε=7,209) of the complex was assigned to a MLCT transition. Besides, the complex also exhibits an emission band at 615 nm that arises from an excitation with a 440 nm light energy. The cyclic voltammetry of the complex shows an oxidation potential at +1.305 V vs. SCE that corresponds to the formal oxidation of Ru(II) to Ru(III)

  19. Chiral Recognition in Molecular and Macromolecular Pairs of(S)- and (R)- 1-Cyano-2-Methylpropyl 4’((4-(8-Vinyloxyoctyloxy)Benzoyl) Biphenyl-4-Carboxylate Enantiomers

    DTIC Science & Technology

    1994-06-30

    2ArH, o to - COOH ), 7.60 (d, J=8.oHz. -kArll. m to - COOH and m to -OCOO-), 7.33 (d, J=8.7Hz, 2ArH, o to -OCOO-), 3.89 ýS )- i-lBnzyloxycarhonyl-2...1H, -COOCH( COOH )-), 3.94 (s. 3t . (1 I CH -. 2.4-4 m. 111. -ClhC’i; r2. 1.17-1-13 (2d, J=5.8Hz, 6H, -CH(CH 3)2). iS - i-(" Cano-2- 1eth,, Ipropil 4...protecting group of (S)-6 and (R)-6 was removed by hydrogenolysis to produce (S)-7 and (R)-7, respectively. Afterwards, the - COOH group of (S)-7 and (R

  20. Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.

    PubMed

    Rivero-Buceta, Eva; Carrero, Paula; Doyagüez, Elisa G; Madrona, Andrés; Quesada, Ernesto; Camarasa, María José; Peréz-Pérez, María Jesús; Leyssen, Pieter; Paeshuyse, Jan; Balzarini, Jan; Neyts, Johan; San-Félix, Ana

    2015-03-06

    Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

  1. Synthesis and Characterization of Bioactive Acylpyrazolone Sulfanilamides and Their Transition Metal Complexes: Single Crystal Structure of 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Sulfanilamide

    PubMed Central

    Idemudia, Omoruyi G.; Sadimenko, Alexander P.; Afolayan, Anthony J.; Hosten, Eric C.

    2015-01-01

    Two Schiff base ligands Ampp-Sn 1 and Bmpp-Sn 2, afforded by a condensation reaction between sulfanilamide and the respective acylpyrazolone carbonyl precursors, their Mn(II), Co(II), Ni(II), and Cu(II) complexes prepared by the reaction of ligands and corresponding metal salts in aqueous solutions, were synthesized and then characterized by both analytical and spectroscopic methods, in a view to developing new improved bioactive materials with novel properties. On the basis of elemental analysis, spectroscopic and TGA results, transition metal complexes, with octahedral geometry having two molecules of the bidentate keto-imine ligand each, have been proposed. The single crystal structure of Bmpp-Sn according to X-ray crystallography showed a keto-imine tautomer type of Schiff base, having three intramolecular bonds, one short N2⋯H2⋯O3 hydrogen bond of 1.90 Å and two long C13⋯H13⋯O2 and C32⋯H32⋯O3 hydrogen bonds of 2.48 Å. A moderate to low biological activities have been exhibited by synthesized compounds when compared with standard antimicrobial agents on screening the synthesized compounds against Staphylococcus aureus, Bacillus pumilus, Proteus vulgaris, and Aeromonas hydrophila for antibacterial activity and against free radical 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) for antioxidant activity. PMID:26106285

  2. 13C and 14N Solid State NMR Characterization of Aramid-Containing Nylon-6 Polymers Synthesized by In Situ Polymerization of Caprolactam with Benzoyl Caprolactam Derivatives.

    DTIC Science & Technology

    1987-12-01

    261.3 show equivalent areas consistant with tiie alternating copolymer structure. Comparison with the model acetanilide (-241.5) indicates the...T.; Fujito, T.; Deguchi. 1\\.; Ando, 1. Macromolecules. 1987, 2?0, 2441. 4 TABLE I CP MNAS ,_’ii N-methyl benzamide -2-o3.3 -226. Acetanilide -241.9

  3. 13C and 15N Solid State MMR Characterization of Aramid-Containing Nylon-6 by In Situ Polymerization with Benzoyl Caprolactam Derivatives.

    DTIC Science & Technology

    1987-12-01

    areas consistant with the alternating copolymer structure. Comparison with the model acetanilide (-241.9) indicates the downfield resonance is due to the...Deguchi, l.; Ando, 1. Macromclecule’-, 1987, 20, 2441. 4 S..:! TABLE I CP-NIAS u N-methyl benzainide -23. 3 2 Acetanilide -241.9 ’iC poly(p-benzamide

  4. Isopropyl 1-benzoyl-4-benzo­yloxy-2,6-di­phenyl-1,2,3,6-tetrahydropyridine-3-carboxyl­ate

    PubMed Central

    Govindan, E.; Murugavel, K.; Amirthaganesan, S.; SubbiahPandi, A.

    2014-01-01

    In the title compound, C35H31NO5, the piperidine ring has an envelope conformation, with the phenyl-substituted C atom adjacent to the methyl­ene C atom as the flap. This flap atom deviates by 0.633 (2) Å from the mean plane of the other five essentially coplanar atoms in the ring (r.m.s. deviation = 0.044 Å). Intra­molecular C—H⋯O hydrogen bonds form S(7) and S(9) ring motifs. In the crystal, mol­ecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with R 2 2(16) loops. PMID:25249905

  5. Separation and purification of berkelium(III) from trivalent actinides and lanthanides using 1-phenyl-3-methyl-4-benzoyl-pyrazolone-5 (HPBMP)

    SciTech Connect

    Mathur, J.N.; Khepkar, P.K.

    1983-01-01

    A solvent extraction method based on the preferential extraction of Bk(III) by 1-phenyl-3-methyl-4-benzeyl-pyrazolone-5 (HPMBP) has been devised for the separation and purification of Bk from other trivalent actinides and lanthanides. A single cycle purification of Bk(III) from most of the impurities is obtained by this method. An alternate method purification of Bk has been given using extraction chromatography with HPMBP impregnated celite columns wherein decontamination factors of approx. 10/sup 4/ are obtained from other trivalent actinides, lanthanides and inactive impurities like iron(Fe), chromium(Cr), aluminum(Al) and nickel(Ni). For Ce(III) (cerium III) a decontamination factor of approx. 60 is obtained.

  6. catena-Poly[[aqua-bis-[2-(3-benzoyl-phen-yl)propano-ato-κO,O]cadmium(II)]-μ-4,4'-bipyridine-κN:N'].

    PubMed

    Jiang, Tao; Ng, Seik Weng

    2011-01-15

    The 4,4'-bipyridine heterocycle in the polymeric title compound, [Cd(C(16)H(13)O(3))(2)(C(10)H(8)N(2))(H(2)O)](n), links adjacent Cd(II) ions into a chain running along the c axis. The Cd atom, which lies on a twofold rotation axis, is chelated by the carboxyl-ate unit and exists in a seven-coordinate penta-gonal-bipyramidal geometry. The apical sites are occupied by N atoms. The water mol-ecule also lies on the twofold rotation axis. The methyl substituent of the propano-ate group is disordered over two positions in a 1:1 ratio. O-H⋯O hydrogen bonding between water molecules and adjacent carboxylate O atoms is observed.

  7. Structure and spectroscopic properties of ruthenium(II) bipyridyl N-benzoyl-N'-(1,10-phenanthrolin-5-Yl)-thiourea

    NASA Astrophysics Data System (ADS)

    Tan, Siew San; Kassim, Mohammad B.

    2015-09-01

    Ruthenium bipyridyl incorporating phenanthroline with thiourea molecules, [Ru(bpy)2(Phen-BT)](PF6)2], has been synthesized and characterized by spectroscopic and electrochemical techniques. The infrared spectra of the complex shows the characteristics stretching frequencies for N-H at 3646 and 3585 cm-1, ν(C-N)phen 1426 cm-1, ν(C=O) 1675 cm-1, ν(C=S) 1246 cm-1, ν(C-H)aromatic 3353-3086 cm-1, ν(C-N)aliphatic 1169-1026 cm-1, ν(C-H)bend 764 cm-1 and ν(PF6-)free 842 cm-1. The complex reveals two π→π* absorption bands at 237 (ɛ=26,302) and 286 nm (ɛ=36,848), which were assigned to the phenanthroline and bipyridyl moieties, respectively. A slightly broad and low energy band in the UV-vis spectrum at 450 nm (ɛ=7,209) of the complex was assigned to a MLCT transition. Besides, the complex also exhibits an emission band at 615 nm that arises from an excitation with a 440 nm light energy. The cyclic voltammetry of the complex shows an oxidation potential at +1.305 V vs. SCE that corresponds to the formal oxidation of Ru(II) to Ru(III).

  8. Synthesis and X-ray crystal structure determination of N-p-methylphenyl-4-benzoyl-3,4-diphenyl-2-azetidinone

    SciTech Connect

    Kabak, Mehmet; Senoez, Huelya; Elmali, Ayhan; Adar, Vildan; Svoboda, Ingrid; Dusek, Michal; Fejfarova, Karla

    2010-12-15

    The title compound, C{sub 29}H{sub 23}NO{sub 2}, has been characterized by single-crystal X-ray diffraction at two different temperatures (303 K and 120 K) and wavelengths (MoK{sub {alpha}} and CuK{sub {alpha}}). The non-centrosymmetric hexagonal crystal structure contains four-membered planar {beta}-lactam ring with an unusually long C-C bond. The {beta}-lactam ring is almost planar.

  9. Topical Acne Treatments and Pregnancy

    MedlinePlus

    ... different ingredients, but common active ingredients are benzoyl peroxide, azelaic acid, glycolic acid, and salicylic acid. Can ... to a developing baby. Can using topical benzoyl peroxide during pregnancy cause birth defects? There are no ...

  10. Acne

    MedlinePlus

    ... ones to see which helps. Products with benzoyl peroxide (say: BEN-zoil peh - ROK - side) or salicylic ( ... are usually pretty helpful for treating acne. Benzoyl peroxide kills the bacteria that can lead to acne ...

  11. Acne

    MedlinePlus

    ... to your skin. These products may contain benzoyl peroxide, sulfur, resorcinol, or salicylic acid. They work by ... gel (tretinoin, Retin-A) Prescription formulas of benzoyl peroxide, sulfur, resorcinol, or salicylic acid Topical azelaic acid ...

  12. Fluorogenic detection of hydrogen sulfide via reductive unmasking of o-azidomethylbenzoyl-coumarin conjugate.

    PubMed

    Wu, Zhisheng; Li, Zhu; Yang, Liu; Han, Jiahuai; Han, Shoufa

    2012-10-18

    Selective detection of hydrogen sulfide was achieved with 7-o-2'-(azidomethyl)benzoyl-4-methylcoumarin via analyte mediated reductive removal of the 2'-(azidomethyl)benzoyl moiety and concurrent generation of fluorescent 7-hydroxy-4-methylcoumarin.

  13. Acne -- self-care

    MedlinePlus

    ... It may help to use a wash with salicylic acid or benzoyl if your skin is oily and ... products may contain benzoyl peroxide, sulfur, resorcinol, or salicylic acid. They work by killing bacteria, drying up skin ...

  14. A Convinient Procedure for Microscale Bezoylations

    NASA Astrophysics Data System (ADS)

    Pandita, Sangeeta; Goyla, Samta

    1997-11-01

    Benzoylation by the Schotten - Baumann method is a useful way to identify and characterize aromatic amines, phenols, sugars, etc. However, for best results, the method requires vigorous shaking in well-stoppered vessels with dropwise addition of benzoyl chloride (1). The fact that benzoyl chloride is a lachrymator may require that these reactions be done outside the laboratory environment in open areas. We report here a convenient procedure for the microscale benzoylation of aromatic amines and phenols.

  15. Deformation and Thermal Properties of Energetic Materials.

    DTIC Science & Technology

    1980-12-01

    decomposition of PETN/polymer samples 5 (b) Thermal decomposition of PETN/ Benzoyl peroxide samples ......... 6 (c) Effect of ultra-violet light on... Benzoyl peroxide samples The results of the preceeding section show that the additives tested have very little effect on the thermal decomposition of PETN...nitrate. In order to test this hypothesis, mixtures of benzoyl peroxide and PETN were used in a series of TG experiments. Benzoyl peroxide is an

  16. Holographic Polymer Dispersed Liquid Crystal (HPDLC) Transmission Gratings Formed by Visible Light Initiated Thiol-Ene Photopolymerization (Postprint)

    DTIC Science & Technology

    2006-10-01

    ion laser. The photoinitiator system consists of the dye oxazine 170 perchlorate and the co-initiator benzoyl peroxide . Electron transfer occurs...between the singlet excited state of the oxazine dye and benxoyl peroxide with subsequent decomposition of the peroxide yielding benzoyl oxy radicals...initiator benzoyl peroxide . Electron transfer occurs between the singlet excited state of the oxazine dye and benzoyl peroxide with subsequent

  17. 21 CFR 133.141 - Gorgonzola cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... manufacturing practice, may be added to the surface of the cheese. (v) Benzoyl peroxide, or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the...

  18. 21 CFR 133.106 - Blue cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is not more than 0.002 percent... magnesium carbonate, singly or combined, is not more than six times the weight of the benzoyl peroxide...

  19. 21 CFR 133.111 - Caciocavallo siciliano cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... concentrated or dried products used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the...

  20. 21 CFR 133.141 - Gorgonzola cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... manufacturing practice, may be added to the surface of the cheese. (v) Benzoyl peroxide, or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the...

  1. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... nonfat dry milk used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the weight of...

  2. 76 FR 36307 - Guidance for Industry on Topical Acne Drug Products for Over-the-Counter Human Use-Revision of...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-06-22

    ... Products for Over-the- Counter Human Use--Revision of Labeling and Classification of Benzoyl Peroxide as...-Counter Human Use--Revision of Labeling and Classification of Benzoyl Peroxide as Safe and Effective... final rule that adds benzoyl peroxide as a generally recognized as safe and effective (GRASE)...

  3. 21 CFR 133.183 - Romano cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk... combined, is not more than six times the weight of the benzoyl peroxide used. If milk is bleached in...

  4. 21 CFR 333.350 - Labeling of acne drug products.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...) For products containing benzoyl peroxide identified in § 333.310(a). (i) The labeling states “Do not use if you have very sensitive skin are sensitive to benzoyl peroxide.” (ii) The labeling states “When... benzoyl peroxide identified in § 333.310(a). (i) The labeling states the directions in paragraph (d)(1)...

  5. 21 CFR 133.106 - Blue cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is not more than 0.002 percent... magnesium carbonate, singly or combined, is not more than six times the weight of the benzoyl peroxide...

  6. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... nonfat dry milk used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the weight of...

  7. 21 CFR 133.183 - Romano cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk... combined, is not more than six times the weight of the benzoyl peroxide used. If milk is bleached in...

  8. 21 CFR 133.111 - Caciocavallo siciliano cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... concentrated or dried products used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the...

  9. [(1R)-3-Benzoyl-1,7,7-trimethyl­bicyclo­[2.2.1]heptan-2-onato-κ2 O,O′]chlorido(η6-p-cymene)ruthenium(II)

    PubMed Central

    Harrad, Mohamed Anouar; Valerga, Pedro; Puerta, M. Carmen; Ali, Mustapha Ait; El Firdoussi, Larbi; Karim, Abdellah

    2010-01-01

    The asymmetric unit of the title compound, [RuCl(C10H14)(C17H19O2)], contains two diastereomers. In both, the RuII ion has a tetra­hedral coordination, formed by two O atoms of the camphor-derived ligand and the p-cymene and Cl ligands. In the crystal structure, weak inter­molecular C—H⋯Cl inter­actions link the mol­ecules into columns propagated along [010]. PMID:21580227

  10. Synthesis, Spectroscopic Characterization, and In Vitro Antimicrobial Studies of Pyridine-2-Carboxylic Acid N'-(4-Chloro-Benzoyl)-Hydrazide and Its Co(II), Ni(II), and Cu(II) Complexes.

    PubMed

    Singh, Jagvir; Singh, Prashant

    2012-01-01

    N-substituted pyridine hydrazide (pyridine-2-carbonyl chloride and 4-chloro-benzoic acid hydrazide) undergoes hydrazide formation of the iminic carbon nitrogen double bond through its reaction with cobalt(II), nickel(II), and copper(II) metal salts in ethanol which are reported and characterized based on elemental analyses, IR, solid reflectance, magnetic moment, molar conductance, and thermal analysis (TG). From the elemental analyses data, 1 : 2 metal complexes are formed having the general formulae [MCl(2)(HL)(2)] ·yH(2)O (where M = Co(II), Ni(II), and Cu(II), y = 1-3). The important infrared (IR) spectral bands corresponding to the active groups in the ligand and the solid complexes under investigation were studied. IR spectra show that ligand is coordinated to the metal ions in a neutral bidentate manner with ON donor sites. The solid complexes have been synthesized and studied by thermogravimetric analysis. All the metal chelates are found to be nonelectrolytes. From the magnetic and solid reflectance spectra, the complexes (cobalt(II), nickel(II), and copper(II)) have octahedral and square planner geometry, respectively. The antibacterial and antifungal activity's data show that the metal complexes have a promising biological activity comparable with the parent ligand against bacterial and fungal species.

  11. Synthesis of novel binary and ternary complexes derived from 1-(2-hydroxy benzoyl)-4-phenylthiosemicarbazide (L1) and 2,2‧-dipyridyl (L2) with CoII, CuII and ZnII salts

    NASA Astrophysics Data System (ADS)

    Azhari, Shaker J.; Mlahi, Mosaad R.; Al-Asmy, Ahmed A.; Mostafa, Mohsen M.

    2015-02-01

    The complexes derived the reactions of 1-(2-hydroxybenzoyl)-4-phenylthiosemicarbazide (L1) with MX2 (M = CoII, CuII and ZnII ions; X = Cl- in case of CoII and CuII ions, Cl- and Ac- in case of ZnII) in EtOH, were synthesized and characterized. The results suggested that the complexes have the general formulae, [Cu(L1-2H)(EtOH)(H2O)2]ṡH2O, [Co(L1-2H)(EtOH)(H2O)]ṡ2H2O and [Zn(L1-2H)(EtOH)]. Also, the ternary complexes, derived from the reactions 2,2‧-dipyridyl (L2) with the metals salts followed by adding a solution of the L1 were synthesized and having the general formulae, [Cu2(L2)(L1-2H)(H2O)(OH)2]ṡ1/2H2O, [Co(L2)(L1-2H)]ṡ1.5EtOHṡ3H2O and [Zn(L2)(L1-2H)]ṡEtOH. The binary and ternary complexes were characterized by elemental analyses, molar conductivities, spectral (IR, UV-Vis, 1H-NMR and mass), thermal and magnetic measurements. The existence of OH group in the ternary complexes was confirmed by IR spectra. The amounts of solvent were determined from the results of TGA. The biological activity for the ligand and two complexes were tested against DNA.

  12. The efficacy and tolerability of a fixed combination clindamycin (1.2%) and benzoyl peroxide (3.75%) aqueous gel in patients with facial acne vulgaris: gender as a clinically relevant outcome variable.

    PubMed

    Harper, Julie C

    2015-04-01

    To investigate whether treatment differences exist in male and female patients with moderate to severe acne treated with clindamycin phosphate 1.2%/BP 3.75% gel or vehicle as monotherapy. A post hoc analysis comparing the efficacy and cutaneous tolerability in 498 male and female patients with moderate to severe acne receiving clindamycin phosphate 1.2%/BP 3.75% gel, or vehicle for 12 weeks. The efficacy of clindamycin phosphate 1.2%/BP 3.75% gel was greater than vehicle (P>.001) in both genders. Within the clindamycin phosphate 1.2%/BP 3.75% gel group, the mean percent change from baseline in inflammatory and noninflammatory lesion counts was greater among females than males, as was the percentage of subjects who achieved a 2-grade reduction in the EGSS (P=.049). It is not possible to determine the contributions of the individual active ingredients. Clindamycin phosphate 1.2%/BP 3.75% gel provides statistically significant greater efficacy than vehicle with a favorable safety and tolerability profile. It appears to be more effective in female patients.

  13. N1-Benzoyl-N2-[1-(1-naphthyl)ethyl]-trans-1,2-diaminocyclohexanes: Development of 4-chlorophenylcarboxamide (calhex 231) as a new calcium sensing receptor ligand demonstrating potent calcilytic activity.

    PubMed

    Kessler, Albane; Faure, Hélène; Petrel, Christophe; Rognan, Didier; Césario, Michèle; Ruat, Martial; Dauban, Philippe; Dodd, Robert H

    2006-08-24

    A structure-activity relationship (SAR) study was performed principally at the N1 position of N1-arylsulfonyl-N2-[1-(1-naphthyl)ethyl]-trans-1,2-diaminocyclohexanes, a new family of calcilytics acting at the calcium sensing receptor (CaSR). The most active compound in this series was the 4-(trifluoromethoxy)benzenesulfonyl derivative 7e, which displayed an IC50 of 5.4 +/- 0.5 microM with respect to the inhibition of calcium-induced tritiated inositol phosphate ([3H]IP) accumulation in Chinese hamster ovarian (CHO) cells expressing the CaSR. Replacement of the sulfonamide linkage of this compound by a carboxamide led to a 6-fold increase in activity (7m, IC50 = 0.9 +/- 0.2 microM). Among the carboxamides synthesized, one of the most active compounds was the 4-chlorophenylcarboxamide (1S,2S,1'R)-7n (Calhex 231, IC50 = 0.33 +/- 0.02 microM). The absolute configuration of (1S,2S,1'R)-7n was deduced from an X-ray crystallographic study of one of the diastereomers of compound 7d. The stereochemical preference for the (1S,2S,1'R)-isomers can be rationalized on the basis of a three-dimensional model of the calcilytic binding pocket of the CaSR. Removal of the C-1' methyl group or replacement of the 1-naphthyl group by a 2-naphthyl or biphenyl moiety led to appreciable loss of calcilytic activity. Compounds 7e, 7m, and Calhex 231 did not stimulate [3H]IP accumulation in CHO cells expressing or not expressing the CaSR.

  14. Experimental and theoretical studies on the functionalization reactions of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid and acid chloride with 2,3-diaminopyridine.

    PubMed

    Yildirim, Ismail; Kandemirli, Fatma; Demir, Elif

    2005-03-31

    The 1H-pyrazole-3-carboxylic acid 2 was converted in good yield (69%) into the corresponding 1H-pyrazole-3-carboxamide 5 via reaction of the acid chloride 3 with 2,3- diaminopyridine (4). A different product, the 3H-imidazo[4,5-b] pyridine derivative 6, was formed from the reaction of 3 with 4 and base in benzene for 5 hours. The structures of the synthesized compounds were determined spectroscopically. The mechanism of the reaction between 3 and 4 was examined theoretically.

  15. Synthesis, Spectroscopic Characterization, and In Vitro Antimicrobial Studies of Pyridine-2-Carboxylic Acid N′-(4-Chloro-Benzoyl)-Hydrazide and Its Co(II), Ni(II), and Cu(II) Complexes

    PubMed Central

    Singh, Jagvir; Singh, Prashant

    2012-01-01

    N-substituted pyridine hydrazide (pyridine-2-carbonyl chloride and 4-chloro-benzoic acid hydrazide) undergoes hydrazide formation of the iminic carbon nitrogen double bond through its reaction with cobalt(II), nickel(II), and copper(II) metal salts in ethanol which are reported and characterized based on elemental analyses, IR, solid reflectance, magnetic moment, molar conductance, and thermal analysis (TG). From the elemental analyses data, 1 : 2 metal complexes are formed having the general formulae [MCl2(HL)2] ·yH2O (where M = Co(II), Ni(II), and Cu(II), y = 1–3). The important infrared (IR) spectral bands corresponding to the active groups in the ligand and the solid complexes under investigation were studied. IR spectra show that ligand is coordinated to the metal ions in a neutral bidentate manner with ON donor sites. The solid complexes have been synthesized and studied by thermogravimetric analysis. All the metal chelates are found to be nonelectrolytes. From the magnetic and solid reflectance spectra, the complexes (cobalt(II), nickel(II), and copper(II)) have octahedral and square planner geometry, respectively. The antibacterial and antifungal activity's data show that the metal complexes have a promising biological activity comparable with the parent ligand against bacterial and fungal species. PMID:23125560

  16. Synthesis of a new heterocyclic Schiff base ligand "(E)-5-benzoyl-4-phenyl-1-((pyridin-2-ylmethylene) amino) pyrimidin-2(1H)-one": An experimental and computational modeling study

    NASA Astrophysics Data System (ADS)

    Ozdemir, Mecit; Sonmez, Mehmet; Sen, Fatih; Dincer, Muharrem; Ozdemir, Namık

    2017-01-01

    In this study, a new heterocyclic Schiff base has been synthesized and characterized using FT-IR, NMR (1H NMR, 13C NMR), UV-Vis, Mass spectroscopies and single-crystal X-ray diffraction method. The molecular geometry obtained from the X-ray structure determination was optimized using Density Functional Theory (DFT/B3LYP) method with the 6-31G+(d, p) basis set in ground state. From the optimized geometry of the title molecule, the geometric parameters (bond lengths, bond angles and torsion angles), vibrational wavenumbers and chemical shifts were computed. In addition, the molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs) and nonlinear optical (NLO) property of this molecule were determined using a DFT protocol at the B3LYP/6-31+G (d, p) level. For the purpose of the structural conformity of the title molecule, the theoretical results were compared with the experimental values. This comparison indicated that the theoretically calculated results are in agreement with the experimental data on the whole.

  17. A novel synthesis of beta-D-mannopyranosyl azide by phase transfer catalysis.

    PubMed

    Abronina, Polina I; Kachala, Vadim V; Kononov, Leonid O

    2009-01-26

    A simple stereoselective synthesis of per-O-benzoyl-beta-d-mannopyranosyl azide from per-O-benzoyl-alpha-d-mannopyranosyl bromide using phase transfer catalysis was developed. The stereochemistry at C-1 of the anomeric O-benzoylated alpha- and beta-d-mannopyranosyl azides was unambiguously established using 2D NOESY NMR spectroscopy. Pure deprotected beta-d-mannopyranosyl azide was prepared by debenzoylation with sodium methoxide in methanol.

  18. Synthesis of Improved Polyester Resins.

    DTIC Science & Technology

    1979-07-05

    peroxides as initiator. The peroxides used were benzoyl peroxide , cumene hydroperoxide, t-butyl peroxybenzoate and 2,5... benzoyl peroxide , while allyl type polyester resins require a higher temperature cure and use a peroxide such as dicumyl peroxide . Numerous other peroxides ...using MEKP (methylethylketone peroxide ) or BZP ( benzoyl peroxide ) catalysts. 47 01 "I 4 C C~ >~> .0 00 Q) . x> x (. C. a, 0 + 0) 0. 0 0 a,. E S- >0>

  19. Initial Development of Composite Repair Resins With Low Hazardous Air Pollutant Contents

    DTIC Science & Technology

    2008-12-01

    giving the proper viscosity and consistency for repair applications. Benzoyl peroxide is typically used as the initiator in repair resin putties...resin (component A) and acts as a promoter to break down the benzoyl peroxide and allow for free radical polymerization at room temperature. N,N...Aldrich) was added to the part A formulation because this chemical promotes free radical cure of benzoyl peroxide initiators, which are typically used

  20. High Refractive Index Si/SiOx Based Nanocomposites

    DTIC Science & Technology

    2000-01-01

    also provide the means for performing chemistry, in the presence of oxidizing agents such as benzoyl peroxide or 3- 328 chloroperbenzoic acid.[32,33...A small amount of benzoyl peroxide (1.79x10" 4 M) was found to produce the optimum results in terms of concentration of Si nanoparticles. Scheme 1...benzoylethyl ester and tetraethoxysilane (TEOS), along with unreacted benzoyl peroxide indicate that sonication can provide considerable amount of

  1. Characterization by Tin-Specific Size Exclusion Chromatography of the Free Radical Copolymerization of Tributyltin Methacrylate and Methyl Methacrylate,

    DTIC Science & Technology

    1980-12-11

    presence of a free radical initiator ( benzoyl peroxide ) at 80.1 OC. Aliquots, taken at preselected intervals from 0 to 1440 min, were fractionated by size...Commercial benzoyl peroxide was employed as the initiator. The THF employed as solvent and chromatographic eluent, containing butylated hydroxytoluene...liter, 3-neck flask equipped with a thermometer, septum, and condenser. To this mixture was added 4.29 g (.018 mole) of benzoyl peroxide . The flask and

  2. 21 CFR 133.195 - Swiss and emmentaler cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... days old. (2) If pasteurized dairy ingredients are used, the phenol equivalent value of 0.25 gram of... treated with hydrogen peroxide/catalase, and is subjected to the action of lactic acid-producing and... cheese. (v) Benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate,...

  3. 4'''-N-demethylspiramycin derivatives: synthesis and evaluation of effectiveness against drug-resistant bacteria.

    PubMed

    Sunazuka, Toshiaki; Shudo, Hiroko; Nagai, Kenichiro; Yoshida, Kiminari; Yamaguchi, Yukie; Hanaki, Hideaki; Omura, Satoshi

    2008-03-01

    18-amino-4''-O-benzoyl-4'''-N-demethyl-18-deoxospiramycins were designed and synthesized. Synthetic strategy involved selective demethylation of the dimethylamino group in forosamine, benzoylation of the hydroxyl group at the C4'' position and reductive N-amination of the formyl group. Antibacterial characteristics of spiramycin derivatives were tested. The derivatives exhibited promising activity against drug-resistant bacterial strains.

  4. Vulnerary Factors to Improve Bone Healing

    DTIC Science & Technology

    2007-04-01

    into the sample was achieved by incubation in infiltration media (90% Methyl Methacrylate, 10% Dibutyl Phthalate, and 70% Benzoyl peroxide 1gm...Methacrylate, 10% Dibutyl Phthalate, and 2gm/100ml 70% Benzoyl peroxide . Once bones were embedded, the blocks were trimmed down using a diamond band

  5. A facile and effective synthesis of alpha-(1-->6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodecasaccharides, and beta-(1-->6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors.

    PubMed

    Zhu, Y; Kong, F

    2001-05-08

    Reaction of 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl trichloroimidate with allyl alpha-D-mannopyranoside in the presence of TMSOTf selectively gave allyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl-(1-->6)-alpha-D-mannopyranoside through an orthoester intermediate. Benzoylation of 3, followed by deallylation, and then trichloroimidation afforded the disaccharide donor 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroimidate, while benzoylation of 3 followed by selective removal of acetyl groups yielded the disaccharide acceptor allyl alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside. Coupling of 5 with 6 gave the tetrasaccharide allyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside, which were converted into the tetrasaccharide donor 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroimdate and the tetrasaccharide acceptor allyl alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside, respectively, by the same strategies as used for conversion of 3 into 5 and 6. Condensation of 5 with 13 gave the hexasaccharide 14, while condensation of 12 with 13 gave the octasaccharide 17. Dodecasaccharide 21 was obtained by the coupling of 12 with the octasaccharide acceptor 20. Similar strategies were used for the syntheses of beta-(1-->6)-linked glucose di-, tri-, tetra-, hexa-, and octamers. Deprotection of the oligosaccharides in ammonia-saturated methanol yielded the free alpha-(1-->6)-linked mannosyl and beta-(1-->6)-linked glucosyl oligomers.

  6. Affinity labeling of protein synthesis factors

    SciTech Connect

    Anthony, D.D.; Dever, T.E.; Abramson, R.D.; Lobur, M.; Merrick, W.C.

    1986-05-01

    The authors laboratory is interested in determining those eukaryotic protein synthesis factors which interact with nucleotides and mRNA. To study the binding the authors have used the nucleotides, their analogs, and mRNA analogs as listed below: (1) UV cross-linking with normal (/sup 32/P)XTP; (2) Oxidized GTP; (3) 3'p-azido benzoyl GDP (GTP); (4) 5'p-fluoro sulfonyl benzoyl guanosine; (5) 5'p-fluoro sulfonyl benzoyl adenosine; (6) oxidized mRNA. Currently, they are continuing their efforts to specifically label the proteins, and they are also trying to isolate a single labeled tryptic peptide from the proteins.

  7. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... whereby the separated fatty acid fraction of the resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen...

  8. Chem Ed Compacts.

    ERIC Educational Resources Information Center

    Wolf, Walter A., Ed.

    1979-01-01

    Tips are presented for chemistry teachers on the use of acid-base half-reactions in review lessons, the use of calculators by chemistry students, significant figures, and the preparation of benzoyl peroxide from acne medicine. (BB)

  9. Natural Acne Treatment: What's Most Effective?

    MedlinePlus

    ... helpful in reducing acne inflammation and breakouts: Tea tree oil. Gels containing 5 percent tea tree oil may be as effective as are lotions containing 5 percent benzoyl peroxide, although tea tree oil might work more slowly. Possible side effects ...

  10. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  11. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  12. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  13. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  14. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  15. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  16. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... separated fatty acid fraction of the resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and...

  17. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used or...

  18. Topical Acne Treatments and Pregnancy

    MedlinePlus

    ... are benzoyl peroxide, azelaic acid, glycolic acid, and salicylic acid. Can I use tretinoin (Retin A®) for severe ... harmful effects on the baby. I read that salicylic acid can cause birth defects in babies. Why is ...

  19. Combination azelaic acid therapy for acne vulgaris.

    PubMed

    Webster, G

    2000-08-01

    There is no topical antiacne medication that acts against all four of the major pathophysiologic features of acne: hyperkeratinization, sebum production, bacterial proliferation, and inflammation. Topical azelaic acid cream helps both to normalize keratinization and to reduce the proliferation of Propionibacterium acnes, and has proven to be effective against both noninflammatory and inflammatory lesions. The results of a recent study now demonstrate that its efficacy can be enhanced, and patient ratings of overall impression improved, when it is used in combination with other topical medications such as benzoyl peroxide 4% gel, clindamycin 1% gel, tretinoin 0.025% cream, and erythromycin 3%/benzoyl peroxide 5% gel. Furthermore, another study has shown that azelaic acid plus benzoyl peroxide achieves greater efficacy and higher patient ratings of convenience than monotherapy with erythromycin-benzoyl peroxide gel.

  20. Iridoid glucosides in the genus Veronica (Plantaginaceae) from New Zealand.

    PubMed

    Kroll-Møller, Phillip; Pedersen, Katja D; Gousiadou, Chrysoula; Kokubun, Tetsuo; Albach, Dirk; Taskova, Rilka; Garnock-Jones, Phil J; Gotfredsen, Charlotte H; Jensen, Søren Rosendal

    2017-08-01

    Four simple iridoid glucosides, three known esters of catalpol, seven esters of aucubin, and two phenylethanoids were isolated from Veronica hookeri (syn. Hebe ciliolata; Plantaginaceae). Of these, none of four aromatic (p-methoxybenzoyl, isovanilloyl, veratroyl, caffeoyl) 6-O-esters of aucubin and 6″-O-benzoyl mussaenosidic acid, had been reported from nature before. Similarly, three simple iridoid glucosides, two esters of 6-O-rhamnopyranosylcatapol, and two phenylethanoid glucosides, as well as 1-O-benzoyl-3-α-glucuronosylglycerol, and 1-O-β-benzoyl rutinoside were isolated from Veronica pinguifolia (syn. Hebe pinguifolia). The compound 3″-O-benzoyl-2″-O-caffeoyl 6-O-rhamnopyranosylcatalpol had not been reported previously. The pattern of the structural features of the iridoid glucosides is overlaid onto the latest molecular phylogenetic framework of Veronica sects. Hebe and Labiatoides, and discussed in the context of evolutionary trends. Copyright © 2017 Elsevier Ltd. All rights reserved.

  1. Sensitive radiometric assay for enkephalin convertase and other carboxypeptidase B-like enzymes

    SciTech Connect

    Stack, G.; Fricker, L.D.; Snyder, S.H.

    1984-01-09

    A sensitive radiometric assay for carboxypeptidase B-like enzymes has been developed using enkephalin convertase, an enkephalin synthesizing carboxypeptidase. The assay is based on the differential solubility of /sup 3/H-labeled substrate and product in chloroform. The substrates /sup 3/H-benzoyl-Phe-Ala-Arg or /sup 3/H-benzoyl-Phe-Leu-Arg are poorly soluble in chloroform due to the charged arginine. The products of carboxypeptidase B-like activity on these substrates, /sup 3/H-benzoyl-Phe-Ala or /sup 3/H-benzoyl Phe-Leu partition quantitatively into chloroform, allowing rapid separation of product from substrate. This assay is approximately 100 times more sensitive than a similar fluorometric assay utilizing dansyl-Phe-Ala-Arg as a substrate.

  2. Chem Ed Compacts.

    ERIC Educational Resources Information Center

    Wolf, Walter A., Ed.

    1979-01-01

    Tips are presented for chemistry teachers on the use of acid-base half-reactions in review lessons, the use of calculators by chemistry students, significant figures, and the preparation of benzoyl peroxide from acne medicine. (BB)

  3. Modified Polypropylene with Improved Physical-Mechanical Properties

    NASA Astrophysics Data System (ADS)

    Chervakov, D. O.; Bashtanyk, P. I.; Burmistr, M. V.

    2015-03-01

    The use of mixtures of benzoyl peroxide and polysiloxane polyol compounds as polypropylene modifiers is suggested. It is established that, in such a way, its physical-mechanical properties can be changed purposefully.

  4. Triplet quenching by diacyl peroxides

    NASA Astrophysics Data System (ADS)

    Ingold, K. U.; Johnston, L. J.; Lusztyk, J.; Scaiano, J. C.

    1984-10-01

    Benzoyl and decanoyl peroxides are efficient quenchers of various triplet sensitizers: kinetic studies using laser photolysis techniques indicate that electronic energy transfer and charge transfer to the peroxide are important factors contributing to the quenching process.

  5. New phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Li, Fa-Sheng; Dou, De-Qiang; Xu, Liang; Chi, Xiao-Feng; Kang, Ting-Guo; Kuang, Hai-Xue

    2009-07-01

    Two new phenolic glycosides were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as (2-hydroxy)phenylcarbinyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1) and 4-beta-D-(glucopyranosyl hydroxymethyl)phenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence.

  6. Directed evolution of a thermostable l-aminoacylase biocatalyst.

    PubMed

    Parker, Brenda M; Taylor, Ian N; Woodley, John M; Ward, John M; Dalby, Paul A

    2011-10-10

    Enzymes from extreme environments possess highly desirable traits of activity and stability for application under process conditions. One such example is l-aminoacylase (E.C. 3.5.1.14) from Thermococcus litoralis (TliACY), which catalyzes the enantioselective amide hydrolysis of N-protected l-amino acids, useful for resolving racemic mixtures in the preparation of chiral intermediates. Variants of this enzyme with improved activity and altered substrate preference are highly desirable. We have created a structural homology model of the enzyme and applied various two different directed evolution strategies to identify improved variants. Mutants P237S and F251Y were 2.4-fold more active towards N-benzoyl valine relative to the wild type at 65°C. F251 mutations to basic residues resulted in 4.5-11-fold shifts in the substrate preference towards N-benzoyl phenylalanine relative to N-benzoyl valine. The substrate preference of wild type decreases with increasingly branched and sterically hindered substrates. However, the mutant S100T/M106K disrupted this simple trend by selectively improving the substrate preference for N-benzoyl valine, with a >30-fold shift in the ratio of k(cat) values for N-benzoyl valine and N-benzoyl phenylalanine. Mutations that favoured N-benzoyl-phenylalanine appeared at the active site entrance, whereas those improving activity towards N-benzoyl-valine occurred in the hinge region loops linking the dimerization and zinc-binding domains in each monomer. These observations support a previously proposed substrate induced conformational transition between open and closed forms of aminoacylases.

  7. Synthesis of dinucleoside (N3'-->MeP5') methanephosphonamidates.

    PubMed

    Nawrot, Barbara; Sobczak, Milena; Antoszczyk, Slawomir

    2002-05-16

    [structure: see text] Three different approaches were used for the synthesis of dinucleoside methanephosphonamidates [3'-NH-P(O)(CH3)O-5'], starting from dichloromethylphosphine or dichloromethanephosphonate as the phosphorus-containing moiety. 5'-DMT-3'-amino-3'-deoxythymidine and N(4)-benzoyl-5'-DMT-3'-amino-2',3'-dideoxycytidine were used as the aminonucleoside precursors and the respective 3'-protected nucleosides (thymidine or N(4)-benzoyl-2'-deoxycytidine) as the 5'-hydroxyl reagents.

  8. Quantitative determination of free glycerol and myo-inositol from plasma and tissue by high-performance liquid chromatography

    PubMed Central

    Frieler, Ryan A.; Mitteness, Dane J.; Golovko, Mikhail Y.; Gienger, Heidi M.; Rosenberger, Thad A.

    2009-01-01

    A high-performance liquid chromatographic method that accurately measures glycerol and myo-inositol from plasma and tissue is described. The method incorporates a pre-column derivatization reaction using aqueous extracts with benzoyl chloride as a modifying agent. The benzoylated derivatives are isolated by HPLC using reversed-phase gradient chromatography and quantified via absorbance detection at 231 nm. The benzoylated derivatives of glycerol and myo-inositol are well resolved from` other know carbohydrates, internal standard and other contaminants encountered within samples and during incubation. The benzoylation of these analytes reach a maximum between 3.5 and 6 h of incubation and are stable for at least 24 days at 4° C. The limit of quantization (LOQ) of glycerol was equal to 2.5 nmol/ml plasma and 6.4 nmol/g tissue and the LOQ of myo-inositol was 1.8 nmol/mL plasma and 3.6 nmol/g tissue. Incubation of known standards and samples with benzoyl chloride at 40° C for 4 h showed fully benzoylated products as determined by mass spectral analysis. Calibration curves were linear between 2.7 and 174 nmol for glycerol and 1.4 to 89 nmol for myo-inositol. Comparison of tissue and plasma concentrations of glycerol and myo-inositol found using this method are in good agreement with other reported values using other techniques. PMID:19783233

  9. Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitro-benzamido)-2-hy-droxy-prop-yl]deca-hydro-isoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitro-benzoyl)pyrrolidin-2-yl]-2-hy-droxy-eth-yl}deca-hydro-iso-quinoline-3-carboxamide.

    PubMed

    Maxson, Tucker; Bertke, Jeffery A; Gray, Danielle L; Mitchell, Douglas A

    2015-11-01

    The crystal structure and absolute configuration of the two new title nelfinavir analogs, C24H35ClN4O5, (I), and C27H39ClN4O5, (II), have been determined. Each of these mol-ecules exhibits a number of disordered moieties. There are intra-molecular N-H⋯O hydrogen bonds in both (I) and (II). In (I) it involves the two carboxamide groups, while in (II) it involves the N-tert-butyl carboxamide group and the 2-hydroxyl O atom. The inter-molecular hydrogen bonding in (I) (O-H⋯O and N-H⋯O) leads to two-dimensional sheets that extend parallel to the ac plane. The inter-molecular hydrogen bonding in (II) (O-H⋯O) leads to chains that extend parallel to the a axis.

  10. 2-Chloro-N-(3-chloro­phen­yl)benzamide

    PubMed Central

    Gowda, B. Thimme; Foro, Sabine; Sowmya, B. P.; Fuess, Hartmut

    2008-01-01

    In the structure of the the title compound, C13H9Cl2NO, the N—H and C=O groups are mutually trans. Furthermore, the conformation of the C=O group is syn to the ortho-chloro group in the benzoyl ring, while the N—H bond is anti to the meta-chloro group in the aniline ring. The amide group forms dihedral angles of 89.11 (19) and 22.58 (37)°, respectively, with the benzoyl and aniline rings, while the benzoyl and aniline rings form a dihedral angle of 69.74 (14)°. The mol­ecules are linked into infinite chains through inter­molecular N—H⋯O hydrogen bonds. PMID:21202929

  11. NMR analysis of diacyl peroxide decomposition in methanol in response to temperature and microwave radiation

    NASA Astrophysics Data System (ADS)

    Haidukevich, O. A.; Skakovskii, E. D.; Tychinskaya, L. Yu.; Zvereva, T. D.; Dikusar, E. A.; Lamotkin, S. A.; Rykov, S. V.

    2012-05-01

    We have studied the decomposition of benzoyl and acetyl benzoyl peroxides in methanol-d4 in response to temperature and microwave radiation. We have shown that chemically-induced dynamic nuclear polarization (CIDNP) can be observed even when the reactions are carried out in spectrometers with high magnetic fields. In this case, spin correlation persists in geminal radical pairs involving labile acyloxyl radicals. Regardless of the method used to initiate peroxide decomposition, the same amount of products are formed. Homolysis occurs according to a chain mechanism. The contribution of induced decomposition decreases over the course of the reaction. Dissolved oxygen molecules efficiently terminate the chain, decreasing the rate of peroxide decomposition. In the case of acetyl benzoyl peroxide, the product yield depends on the initiation mechanism: for microwave irradiation, the solvent molecules are more active while dissolved oxygen is less active than in thermolysis.

  12. Holographic polymer dispersed liquid crystal (HPDLC) transmission gratings formed by visible light initiated thiol-ene photopolymerization

    NASA Astrophysics Data System (ADS)

    Wofford, Jeremy M.; Natarajan, Lalgudi V.; Tondiglia, Vincent P.; Sutherland, Richard L.; Lloyd, Pamela F.; Siwecki, Stephen A.; Bunning, Timothy J.

    2006-08-01

    We report on the initial development of a visible initiator for thiol-ene photopolymerization using the 647 nm radiation from a Krypton ion laser. The photoinitiator system consists of the dye oxazine 170 perchlorate and the co-initiator benzoyl peroxide. Electron transfer occurs between the singlet excited state of the oxazine dye and benzoyl peroxide with subsequent decomposition of the peroxide yielding benzoyl oxy radicals capable of free radical initiation. We demonstrate that this photoinitiation system enables holographic patterning of HPDLC gratings as initial Bragg transmission gratings with a periodicity less than one micron using 647 nm radiation. These gratings were electrically switchable between a diffractive and transmissive state. Morphology studies using bright field transmission electron microscopy (BFTEM) indicate the phase separation of nearly spherical shaped nematic liquid crystal droplets of several hundred nanometers in diameter. This demonstration suggests that reflection gratings can be written using this photoinitiator system and 647 nm radiation which have switchable notch wavelengths approaching 2 microns.

  13. Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones.

    PubMed

    Kim, Hun Young; Song, Eunsun; Oh, Kyungsoo

    2017-01-20

    A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.

  14. Palladium-catalyzed N-acylation of monosubstituted ureas using near-stoichiometric carbon monoxide.

    PubMed

    Bjerglund, Klaus; Lindhardt, Anders T; Skrydstrup, Troels

    2012-04-20

    The palladium-catalyzed carbonylation of urea derivatives with aryl iodides and bromides afforded N-benzoyl ureas (20 examples) in yields attaining quantitative via the application of near-stoichiometric amounts of carbon monoxide generated from the decarbonylation of the CO precursor, 9-methylfluorene-9-carbonyl chloride. The synthetic protocol displayed good functional group tolerance. The methodology is also highly suitable for (13)C isotope labeling, which was demonstrated through the synthesis of three benzoyl ureas, including the insecticide triflumuron, whereby (13)CO was incorporated into the core structure. © 2012 American Chemical Society

  15. N-(3-Chloro-benzo-yl)-2-methyl-benzene-sulfonamide.

    PubMed

    Suchetan, P A; Foro, Sabine; Gowda, B Thimme

    2011-12-01

    In the title compound, C(14)H(12)ClNO(3)S, the N-H bond in the C-SO(2)-NH-C(O) segment is anti to the C=O bond. Further, the C=O bond and the meta-Cl atom in the benzoyl ring are also anti to each other. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

  16. Acne Vulgaris in the Athlete.

    PubMed

    Conklin, R J; Taunton, J E

    1988-10-01

    In brief: The treatment of acne is basically the same for athletes and nonathletes. However, certain aspects of sports can affect acne adversely, and in some cases treating athletes may require a cautious approach. The best treatments are topical tretinoin for comedonal acne, benzoyl peroxide or topical antibiotics and tretinoin for comedonal and mild pustular acne, and a combination of oral antibiotics and long-term benzoyl peroxide or topical antibiotics (with the eventual aim of stopping the oral antibiotics in three to five months) for moderate to severe pustular acne. For severe cystic/nodular acne, highdose oral antibiotics and intralesional steroid injections or oral isotretinoin should be considered.

  17. A highly sensitive quantification of phytosterols through an inexpensive derivatization.

    PubMed

    Liu, Songbai; Ruan, Huina

    2013-01-01

    A highly sensitive method for quantification of phytosterols based on HPLC has been developed by derivatization with the benzoyl chromophore. Introduction of the chromophore, benzoyl group, to phytosterols via simple and inexpensive derivatization greatly improved the UV response at 254 nm. Quantification of phytosterols was effectively performed by HPLC analysis with methyl benzoate as the internal standard after derivatization. This new method demonstrated outstanding yield of recovery (> 95%) and excellent sensitivity (ng level) and was applicable for sterols from either plant or animal sources. This method is generally useful in phytosterol studies.

  18. (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl benzoate

    PubMed Central

    Oubabi, Radouane; Auhmani, Aziz; Ait Itto, My Youssef; Auhmani, Abdelwahed; Daran, Jean-Claude

    2014-01-01

    The title compound, C27H34O2, was hemisynthesized through direct benzoyl­ation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the mol­ecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter. PMID:25249914

  19. Photolysis of alpha-azidoacetophenones: trapping of triplet alkyl nitrenes in solution.

    PubMed

    Mandel, S M; Krause Bauer, J A; Gudmundsdottir, A D

    2001-02-22

    [reaction: see text] Selective excitation of the ketone chromophore in alpha-azidoacetophenones, 1, leads to intramolecular triplet energy transfer to the azido group, which forms the corresponding triplet alkyl nitrene, 2. Azides 1 also undergo alpha-cleavage to form benzoyl and methyl azido radicals in competition with nitrene formation. Thus the major photoproduct, 2-benzoylamino-1-phenylethanone, 3, comes from trapping of 2 with a benzoyl radical. This appears to be the first observation of bimolecular trapping of triplet alkyl nitrenes in solution.

  20. Preparation of the different derivatives of the low-molecular-weight porphyran from Porphyra haitanensis and their antioxidant activities in vitro.

    PubMed

    Zhang, Zhongshan; Zhang, Quanbin; Wang, Jing; Zhang, Hong; Niu, Xizhen; Li, Pengcheng

    2009-07-01

    Porphyran extracted from Porphyra haitanensis is a sulfated polysaccharide, which possesses excellent antioxidant activities. In this study, we prepared one low-molecular-weight porphyran and its sulfated, acetylated, phosphorylated and benzoylated derivatives. Their antioxidant activities were investigated including scavenging effect of superoxide, hydroxyl and 1,1-diphenyl-2-picrylhydrazyl radicals. The results of chemical analysis and FT-IR spectrums showed the modification was successful. And in addition, we found that certain derivative exhibited stronger antioxidant activity than low-molecular-weight porphyran. The benzoylated derivative showed the most excellent antioxidant activity in three assays, so this derivative needs to be attended to.

  1. 21 CFR 137.105 - Flour.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... or inferiority or makes the flour appear to be better or of greater value than it is, one or any...) Chlorine. (3) Nitrosyl chloride. (4) Chlorine dioxide. (5) One part by weight of benzoyl peroxide mixed... phosphate, starch, calcium carbonate. (6) Acetone peroxides complying with the provisions of § 172.802...

  2. 21 CFR 177.2420 - Polyester resins, cross-linked.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...: Total not to exceed 1.5 percent, except that methyl ethyl ketone peroxide may be used as the sole catalyst at levels not to exceed 2 percent. Azo-bis-isobutyronitrile Benzoyl peroxide tert-Butyl perbenzoate Chlorbenzoyl peroxide Cumene hydroperoxide Dibutyltin oxide (CAS Reg. No. 818-08-6) For use in...

  3. The "Mushroom Cloud" Demonstration Revisited

    ERIC Educational Resources Information Center

    Panzarasa, Guido; Sparnacci, Katia

    2013-01-01

    A revisitation of the classical "mushroom cloud" demonstration is described. Instead of aniline and benzoyl peroxide, the proposed reaction involves household chemicals such as alpha-pinene (turpentine oil) and trichloroisocyanuric acid ("Trichlor") giving an impressive demonstration of oxidation and combustion reactions that…

  4. Influence of Bleaching on Flavor of 34% Whey Protein Concentrate and Residual Benzoic Acid Concentration in Dried Whey Proteins

    USDA-ARS?s Scientific Manuscript database

    Previous studies have shown that bleaching negatively affects the flavor of 70% whey protein concentrate (WPC70), but bleaching effects on lower-protein products have not been established. Benzoyl peroxide (BP), a whey bleaching agent, degrades to benzoic acid (BA) and may elevate BA concentrations...

  5. Characterization of AlFe-pillared Unye bentonite: A study of the surface acidity and catalytic property

    NASA Astrophysics Data System (ADS)

    Caglar, Bulent; Cubuk, Osman; Demir, Ersin; Coldur, Fatih; Catir, Mustafa; Topcu, Cihan; Tabak, Ahmet

    2015-06-01

    Aluminium-iron-pillared bentonite has been prepared by incorporation of the iron mixed aluminium-polyoxocation into bentonite layers and characterized by the powder X-ray diffraction, Fourier transform infrared, thermal analysis and surface area measurement techniques. The characteristic d001 basal spacing of raw bentonite increased with the pillaring process and reached to 18.05 Å. The siloxane layers of bentonite were perturbed and the positions of Si-O stretching vibrations were altered by pillaring process. However, these pillars in the interlayer gallery spacing enhanced the thermal stability of bentonite. The new micropores were formed by the pillaring process and the specific surface area of raw bentonite increased by ca. 2-fold for aluminium-iron-pillared bentonite. FTIR spectra and thermal analysis curves of pyridine adsorbed samples clearly show that the surface Lewis acidity of aluminium-iron-pillared bentonite is greater than that of raw bentonite. Raw and aluminium-iron-pillared bentonites have been utilized as solid catalysts for benzoylation of benzene with benzoyl chloride. The aluminium-iron-pillared bentonite catalyst showed promising catalytic activity whereas raw bentonite showed no catalytic activity in benzoylation of benzene with benzoyl chloride.

  6. Carbohydrates from Detarium microcarpum bark extract.

    PubMed

    Abreu, Pedro; Relva, Angela

    2002-10-08

    The bark extract of the medicinal plant Detarium microcarpum was analysed for its carbohydrate content by GLC-CIMS. Preparative HPLC of the benzoylated carbohydrate fraction led to the isolation of L-quino-1,5-lactone, D-(-)-bornesitol, D-pinitol, myo-inositol, sucrose, D-glucose, and D-fructose benzoates, which were characterised by NMR spectroscopy experiments.

  7. 21 CFR 172.345 - Folic acid (folacin).

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Folic acid (folacin). 172.345 Section 172.345 Food... Special Dietary and Nutritional Additives § 172.345 Folic acid (folacin). Folic acid (CAS Reg. No. 59-30-3... following prescribed conditions: (a) Folic acid is the chemical N- amino]benzoyl]-L-glutamic acid. (b) Folic...

  8. Thermomechanical pulp fiber surface modification for enhancing the interfacial adhesion with polypropylene

    Treesearch

    Sangyeob Lee; Todd F. Shupe; Leslie H. Groom; Chung Y. Hse

    2007-01-01

    Chemical coupling on the thermomechanical pulp (TMP) fiber improved tensile strength of the TMP fiber handsheet and isotactic polypropylene film laminates (TPL). For the maleic anhydride W) with benzoyl peroxide (BPO)a an initiator, tensile strength increaded 52: with the TMP fiber treatment over untreated laminates. The optimum strength properties were obtained with...

  9. Ability of m-chloroperoxybenzoic acid to induce the ornithine decarboxylase marker of skin tumor promotion and inhibition of this response by gallotannins, oligomeric proanthocyanidins, and their monomeric units in mouse epidermis in vivo

    Treesearch

    Guilan Chen; Elisabeth M. Perchellet; Xiao Mei Gao; Steven W. Newell; Vittorio Bottari; Richard W. Hemingway; Jean-Pierre Perchellet

    1995-01-01

    m-Chloroperoxybenzoic acid (CPBA) was tested for its ability to induce the ornithine decarboxylase (ODC) marker of skin tumor promotion. In contrast to benzoyl peroxide, dicumyl peroxide, and 2-butanol peroxide, 5 mg of CPBA applied twice at a 72-h interval induce DOC activity at least as much as 3 µg of 12-O-tetradecanoylphorbol-13.acetate (TPA)....

  10. Ability of m-chloroperoxybenzoic acid to induce the ornithine decarboxylase marker of skin tumor promotion and inhibition of this response by gallotannins, oligomeric proanthocyanidins, and their monomeric units in mouse epidermis in Vivo

    Treesearch

    Guilan Chen; Elisabeth M. Perchellet; Xiao Mei Gao; Steven W. Newell; richard W. Hemingway; Vittorio Bottari; Jean-Pierre Perchellet

    1995-01-01

    m-Chloroperoxybenzoic acid (CPBA) was tested for its ability to induce the ornithine decarboxylase (ODC) marker of skin tumor promotion. In contrast to benzoyl peroxide, dicumyl peroxide, and 2-butanol peroxide, 5 mg of CPBA applied twice at a 72-h interval induce ODC activity at least as much as 3 ug of 12-O-tetradecanoylphorbol-13-acetate (TPA). ODC induction peaks...

  11. Structure-Based Design of Inhibitors to the Cytotoxin Ricin

    DTIC Science & Technology

    2007-04-01

    route (Scheme 1) requires elaboration of appropriate 2-substituted 5-amino- oxazoles , which are then acylated with benzoyl isocyanate, activated by...propyl oxazoles 4a,b in base affords the 8- substituted 3-thio-9-oxo-xanthines 10a,b. Alkylation of the 8-methyl derivative 10a proceeded well with a

  12. Maleated polypropylene film and wood fiber handsheet laminates

    Treesearch

    Sangyeob Lee; Todd F. Shupe; Leslie H. Groom; Chung Y. Hse

    2008-01-01

    The grafting effect of maleic anhydride (MA) as an interfacial bonding agent and its influence on the tensile strength properties of thermomechanical pulp handsheet-isotactic polypropylene (iPP) film laminates was studied. For the MA treated with benzoyl peroxide (BPO) as an initiator, tensile strength properties increased 76% with PP film over untreated laminates. The...

  13. 21 CFR 178.3570 - Lubricants with incidental food contact.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... tall oil fatty acid (C16 and C18) amine and ethylene diamine in a 2:2:1 molar ratio For use only as an... Limitations Aluminum stearoyl benzoyl hydroxide For use only as a thickening agent in mineral oil lubricants at a level not to exceed 10 pct by weight of the mineral oil....

  14. 21 CFR 178.3570 - Lubricants with incidental food contact.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... tall oil fatty acid (C16 and C18) amine and ethylene diamine in a 2:2:1 molar ratio For use only as an... Limitations Aluminum stearoyl benzoyl hydroxide For use only as a thickening agent in mineral oil lubricants at a level not to exceed 10 pct by weight of the mineral oil....

  15. The "Mushroom Cloud" Demonstration Revisited

    ERIC Educational Resources Information Center

    Panzarasa, Guido; Sparnacci, Katia

    2013-01-01

    A revisitation of the classical "mushroom cloud" demonstration is described. Instead of aniline and benzoyl peroxide, the proposed reaction involves household chemicals such as alpha-pinene (turpentine oil) and trichloroisocyanuric acid ("Trichlor") giving an impressive demonstration of oxidation and combustion reactions that…

  16. High chemiluminescence activity of an Fe(III)-TAML activator in aqueous-organic media and its use in the determination of organic peroxides.

    PubMed

    Demiyanova, Alexandra S; Sakharov, Ivan Yu

    2015-05-07

    High activity of Fe(III)-TAML, peroxidase mimic, upon the catalytic oxidation of luminol in aqueous-organic media (ethanol, isopropanol and acetonitrile) was determined. Using Fe(III)-TAML the sensitive chemiluminescence assays for the determination of benzoyl peroxide and tert-butyl hydroperoxide in the presence of organic solvents were performed.

  17. Free-radical reactions of 2-ethoxy-1,3-oxathiolane

    SciTech Connect

    Taganliev, A.; Pastushenko, E.V.; Rakhmankulov, D.L.; Rol'nik, L.Z.; Zlotskii, S.S.

    1986-01-01

    Homolytic reactions of 2-ethoxy-1,3-oxathiolane in the presence of benzoyl peroxide and tert-butyl peroxide in chlorobenzene have been studied. The principal reaction products are diethyl monothiocarbonate and 1,3-oxathiolane-2-one. The yields and ratios of the products are temperature-dependent.

  18. Sorption properties of perbenzoylated β-cyclodextrin deposited onto a carbon support

    NASA Astrophysics Data System (ADS)

    Kopytin, K. A.; Kudryashov, S. Yu.; Gerasimova, N. G.; Onuchak, L. A.

    2012-11-01

    Thermodynamic parameters are determined for the adsorption of vapors of hydrocarbons and polar compounds of different structure on carbon adsorbent modified by a monomolecular layer of heptakis(2,3,6-tri- O-benzoyl)-β-cyclodextrin. The effect of the structure and polarity of organic compounds on adsorption onto an adsorbent support with a chiral macrocyclic modifier are considered.

  19. 21 CFR 172.345 - Folic acid (folacin).

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... following prescribed conditions: (a) Folic acid is the chemical N- amino]benzoyl]-L-glutamic acid. (b) Folic... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Folic acid (folacin). 172.345 Section 172.345 Food... Special Dietary and Nutritional Additives § 172.345 Folic acid (folacin). Folic acid (CAS Reg. No. 59-30-3...

  20. Direct interactions between the coiled-coil tip of DksA and the trigger loop of RNA polymerase mediate transcriptional regulation

    USDA-ARS?s Scientific Manuscript database

    E. coli DksA is in a class of transcription factors that modify RNA polymerase (RNAP) in all three kingdoms of life. DksA potentiates the effects of the global regulator ppGpp and the initiating NTP, controlling transcription initiation without binding to DNA. Incorporating benzoyl-phenylalanine (Bp...

  1. METHOD OF PREPARING COMPLEXES OF PLUTONIUM WITH DIKETONES

    DOEpatents

    Dixon, J.S.; Katz, J.J.; Orlemann, E.F.

    1961-06-20

    A process is described for sepsrating Pu from an aqueous alkaline solution by either precipitating with a beta -diketone or extracting into a solution of the beta -dixetone in an organic water-immiscible solvent. Acetyl acetone and benzoyl acetone are the beta -diketones used.

  2. Influence of bleaching on flavor of 34% whey protein concentrate and residual benzoic acid concentration in dried whey products

    USDA-ARS?s Scientific Manuscript database

    Previous studies have shown that bleaching negatively affects the flavor of 70% whey protein concentrate (WPC70), but bleaching effects on lower-protein products have not been established. Benzoyl peroxide (BP), a whey bleaching agent, degrades to benzoic acid (BA) and may elevate BA concentrations...

  3. New artificial siderophores based on a monosaccharide scaffold.

    PubMed

    Heggemann, S; Schnabelrauch, M; Klemm, D; Möllmann, U; Reissbrodt, R; Heinisch, L

    2001-03-01

    New artificial catecholate siderophores with methyl alpha-D-glucopyranoside as scaffold were synthesized. The dihydroxy- or di(acetoxy)benzoyl moieties were attached either directly or via aminopropyl spacer groups, to the carbohydrate scaffold. The siderophore activity of the prepared siderophore analogs was examined by a growth promotion assay using various Gram-negative bacteria and mycobacteria and by the CAS-assay.

  4. Safe Preparation of HCl and DCl for IR Spectroscopy

    ERIC Educational Resources Information Center

    Furlong, William R.; Grubbs, W. Tandy

    2005-01-01

    The widely used method of synthesizing HCl and DCl gases for infrared analysis by hydrolysis of benzoyl chloride includes a potentially dangerous final step whereby the frozen product is allowed to heat and expand into an infrared gas cell. The subsequent rapid rise in vapor pressure can "pop" open glass joints in the vacuum line and vent the…

  5. 2,2'-(1,4-Phenyl-ene)bis-(propane-2,2-di-yl) bis-(benzodi-thio-ate).

    PubMed

    Moreno-Fuquen, Rodolfo; Grande, Carlos; Advincula, Rigoberto C; Tenorio, Juan C; Ellena, Javier

    2014-02-01

    The title compound, C26H26S4, shows a dihedral angle of 76.64 (15)° between the central and peripheral benzene rings. An inversion center is located at the centroid of the thio-benzoyl ring. In the crystal, weak C-H⋯S inter-actions form C(5) chains along [001]. There are no classical hydrogen bonds.

  6. Constituents of cultivated Agaricus blazei.

    PubMed

    Ueguchi, Yumi; Matsunami, Katsuyoshi; Otsuka, Hideaki; Kondo, Kazunari

    2011-04-01

    Two phenylhexane derivatives (1, 2), benzoylergostane (3), N-benzoyl-L-leucine methyl ester (4), two known ergostanes, and highly degraded incisterol were isolated from fruit bodies of Agaricus blazei. Compound 3 exhibited strong cytotoxicity toward HepG2 cells (IC(50) = 6.0 ± 0.33 μM).

  7. Safe Preparation of HCl and DCl for IR Spectroscopy

    ERIC Educational Resources Information Center

    Furlong, William R.; Grubbs, W. Tandy

    2005-01-01

    The widely used method of synthesizing HCl and DCl gases for infrared analysis by hydrolysis of benzoyl chloride includes a potentially dangerous final step whereby the frozen product is allowed to heat and expand into an infrared gas cell. The subsequent rapid rise in vapor pressure can "pop" open glass joints in the vacuum line and vent the…

  8. 2-Isopropyl-4-meth­oxy-5-methyl­phenyl benzoate

    PubMed Central

    Moumou, Mohamed; Akssira, Mohamed; Elhakmaoui, Ahmed; El Ammari, Lahcen; Benharref, Ahmed; Berraho, Moha

    2010-01-01

    The title compound, C18H20O3, a hemisynthetic product, was obtained by the reaction of benzoyl chloride and p-methoxy­thymol. The structure comprises two benzene rings bridged by a carboxyl group; the dihedral angle between the rings is 73.54 (8)°. PMID:21580674

  9. Effects of silane on the properties of wood-plastic composites with polyethylene-polypropylene blends as matrices

    Treesearch

    Craig M. Clemons; Ronald C. Sabo; Michael L. Kaland; Kolby C. Hirth

    2011-01-01

    The influence of 3-(trimethoxysilyl)propyl methacrylate and benzoyl peroxide on gel content, crystallinity, and mechanical performance of unfilled PP-PE blends, and their composites with wood was investigated. All materials were compounded in a twin screw extruder and then injection molded. Specimens were then exposed to high-humidity and elevated temperature in a...

  10. Synthesis and antitumor activity of novel dibutyltin carboxylates of aminoglucosyl derivatives.

    PubMed

    Li, Wei; Zhang, Zhong-Wei; Ren, Su-Mei; Sibiril, Yann; Parent Massin, Dominique; Jiang, Tao

    2009-06-01

    In this study, di-n-butyltin(IV) oxide was reacted with the amino glucose analog, cis-4-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl)imido]-4-oxo-2-butenoic acid (1a) and o-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl) carbamoyl] benzoic acid (2a) to give the complexes bis-{cis-4-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl)imido-4-oxo-2-butenoic acid]-di-n-butyltin} carboxylate (1) and bis-{o-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl) carbamoyl-benzoic acid]-di-n-butyltin}carboxylate (2). These two compounds were then characterized by IR, NMR and MS. In vitro tests showed that both compounds have high cytotoxicity in four tumor cell lines (P388, HL-60, A549 and BEL-7402). Clonogenic assays demonstrated that both compounds 1 and 2 have hematopoietic cell toxicity at 10(-6) M.

  11. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... whereby the separated fatty acid fraction of the resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used or intended for use, in accordance with...

  12. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... whereby the separated fatty acid fraction of the resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used or intended for use, in accordance with...

  13. Sidewall functionalization of single-walled carbon nanotubes with organic peroxides.

    PubMed

    Peng, Haiqing; Reverdy, Paul; Khabashesku, Valery N; Margrave, John L

    2003-02-07

    Single-wall carbon nanotubes (SWNTs) and their fluorinated derivatives (F-SWNTs) were reacted with organic peroxides including benzoyl and lauroyl peroxide to produce phenyl and undecyl sidewall functionalized SWNTs, respectively, which were characterized by Raman, FTIR, and UV-Vis-NIR spectra as well as TGA/MS, TGA/FTIR, and TEM data.

  14. 21 CFR 184.1400 - Lecithin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Lecithin. 184.1400 Section 184.1400 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) DIRECT FOOD... benzoyl peroxide and dried by heating. (b) The ingredient meets the specifications of the Food Chemicals...

  15. Tissue-specific PhBPBT expression is differentially regulated in response to endogenous ethylene

    USDA-ARS?s Scientific Manuscript database

    Ethylene is a gaseous plant hormone involved in many physiological processes including senescence, fruit ripening, and defense. Here we show the effects of pollination and wound-induced ethylene signals on transcript accumulation of benzoyl CoA:benzyl alcohol/phenylethanol benzoyltransferase (PhBPBT...

  16. Small Crater Expedient Repair Test.

    DTIC Science & Technology

    1980-08-01

    Crater 4, the timed polymer-concrete repair, failed due to material quality. An estimated 20 of the 464 bags of SilikalO lacked the benzoyl ... peroxide catalyst required for polymerization. As a result of this omission, several areas of the repair failed to harden, causing the unpolymerized mateiial

  17. Hydrophosphorylation of alkynes with phosphinous acids

    SciTech Connect

    Nifant'ev, E.E.; Solovetskaya, L.A.; Magdeeva, R.K.

    1986-03-20

    A feature of the homolytic hydrophosphorylation of alkynes, as compared with alkenes, is more ready addition of phosphinous acids in presence of benzoyl peroxides. A difference was found in the hydrophosphorylation of acetylenes with dibutylphosphinous acid and with diarylphosphinous acids: the latter tend to form diaddition products.

  18. 21 CFR 177.2420 - Polyester resins, cross-linked.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ...: Total not to exceed 1.5 percent, except that methyl ethyl ketone peroxide may be used as the sole catalyst at levels not to exceed 2 percent. Azo-bis-isobutyronitrile Benzoyl peroxide tert-Butyl perbenzoate Chlorbenzoyl peroxide Cumene hydroperoxide Dibutyltin oxide (CAS Reg. No. 818-08-6) For use in...

  19. Room Temperature Curing Resin Systems for Graphite/Epoxy Composite Repair.

    DTIC Science & Technology

    1979-12-01

    peroxides , such as methyl ethyl ketone peroxide (MEKP), cumene hydroperoxide (CHP), and benzoyl peroxide (BPO), which are activated at room temperature...temperature curing adhesives. A typical system composed of Dow’s fe. .ane resin cured with methyl ethyl ketone peroxide had a glass transition

  20. Using GC-MS to Determine Relative Reactivity Ratios

    NASA Astrophysics Data System (ADS)

    Bishop, R. Daniel, Jr.

    1995-08-01

    An undergraduate organic chemistry microscale experiment involving the monochlorination of methylcyclohexane using sulfuryl chloride and benzoyl peroxide is described. Simple GC-MS analysis of the product mixture allows students to calculate relative reactivity ratios for free-radical chlorination of primary, secondary, and tertiary carbons in methylcyclohexane.

  1. 21 CFR 177.2420 - Polyester resins, cross-linked.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ...: Total not to exceed 1.5 percent, except that methyl ethyl ketone peroxide may be used as the sole catalyst at levels not to exceed 2 percent. Azo-bis-isobutyronitrile Benzoyl peroxide tert-Butyl perbenzoate Chlorbenzoyl peroxide Cumene hydroperoxide Dibutyltin oxide (CAS Reg. No. 818-08-6) For use in...

  2. Hydrogen-bonding patterns in two aroylthio­carbamates and two aroylimidothio­carbonates

    PubMed Central

    Insuasty, Henry; Castro, Edison; Sánchez, Edison; Cobo, Justo; Glidewell, Christopher

    2010-01-01

    In O-ethyl N-benzoyl­thio­carbamate, C10H11NO2S, the mol­ecules are linked into sheets by a combination of two-centre N—H⋯O and C—H⋯S hydrogen bonds and a three-centre C—H⋯(O,S) hydrogen bond. A combination of two-centre N—H⋯O and C—H⋯O hydrogen bonds links the mol­ecules of O-ethyl N-(4-methyl­benzoyl)thio­carbamate, C11H13NO2S, into chains of rings, which are linked into sheets by an aromatic π–π stacking inter­action. In O,S-diethyl N-(4-methyl­benzoyl)imidothio­carbonate, C13H17NO2S, pairs of mol­ecules are linked into centrosymmetric dimers by pairs of symmetry-related C—H⋯π(arene) hydrogen bonds, while the mol­ecules of O,S-diethyl N-(4-chloro­benzoyl)imidothio­carbonate, C12H14ClNO2S, are linked by a single C—H⋯O hydrogen bond into simple chains, pairs of which are linked by an aromatic π–π stacking inter­action to form a ladder-type structure. PMID:20203412

  3. N-Substituted pyrazole-3-carboxamides as inhibitors of human 15-lipoxygenase.

    PubMed

    Pelcman, Benjamin; Sanin, Andrei; Nilsson, Peter; Schaal, Wesley; Olofsson, Kristofer; Krog-Jensen, Christian; Forsell, Pontus; Hallberg, Anders; Larhed, Mats; Boesen, Thomas; Kromann, Hasse; Claesson, Hans-Erik

    2015-08-01

    High-throughput screening was used to find selective inhibitors of human 15-lipoxygenase-1 (15-LOX-1). One hit, a 1-benzoyl substituted pyrazole-3-carboxanilide (1a), was used as a starting point in a program to develop potent and selective 15-LOX-1 inhibitors.

  4. The bamA gene for anaerobic ring fission is widely distributed in the environment

    PubMed Central

    Porter, Abigail W.; Young, Lily Y.

    2013-01-01

    Benzoyl-CoA is the signature central metabolite associated with the anaerobic metabolism of a diverse range of compounds such as humic acid, lignin, amino acids, and industrial chemicals. Aromatic chemicals with different upstream degradation pathways all funnel into the downstream benzoyl-CoA pathway. Different genes encoding enzymes of the benzoyl-CoA pathway could be used as biomarkers for the anaerobic benzoyl-CoA pathway, however, the ring opening hydrolase, encoded by the bamA gene, is ideal because it is detected under a range of respiratory conditions, including under denitrifying, iron-reducing, sulfate-reducing, and fermentative conditions. This work evaluated DNA samples from six diverse environments for the presence of the bamA gene, and had positive results for every sample. Individual bamA gene clones from these sites were compared to published genome sequences. The clone sequences were distributed amongst the genome sequences, although there were clone sequences from two of the analyzed sites that formed a unique clade. Clone sequences were then grouped by site and analyzed with a functional operational taxonomic unit based clustering program to compare the bamA gene diversity of these sites to that of several locations reported in the literature. The results showed that the sequence diversity of the sites separated into two clusters, but there was no clear trend that could be related to the site characteristics. Interestingly, two pristine freshwater sites formed a subgroup within one of the larger clusters. Thus far the bamA gene has only been examined within the context of contaminated environments, however, this study demonstrates that the bamA gene is also detected in uncontaminated sites. The widespread presence of the bamA gene in diverse environments suggests that the anaerobic benzoyl-CoA pathway plays an important role in the global carbon cycle that has thus far been understudied. PMID:24133487

  5. Benzophenones of Garcinia pseudoguttifera (Clusiaceae).

    PubMed

    Ali, S; Goundar, R; Sotheeswaran, S; Beaulieu, C; Spino, C

    2000-01-01

    Four biogenetically related benzophenones have been isolated from the Fijian Garcinia pseudoguttifera. They are: 6-hydroxy-2,4-dimethoxy-3,5-bis(3-methyl-2-butenyl)benzophenone (myrtiaphenone-A); 2,2-dimethyl-8-benzoyl-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)benzopy ran (myrtiaphenone-B); 2,6-dihydroxy-4-methoxy-3,5-bis(3-methyl-2-butenyl)benzophenone (vismiaphenone-C) and a new benzophenone, 2,2-dimethyl-8-benzoyl-3,7-dihydroxy-5-methoxy- 6-(3-methyl-2-butenyl)-3,4-dihydrobenzopyran (pseudoguttiaphenone-A). Pseudoguttiaphenone-A could be biogenetically derived from vismiaphenone-C. The major component of G. pseudoguttifera was identified as eupha-8,24-dien-3 beta-ol.

  6. Synthesis and hypoglycemic activity of S-acyl derivatives of 3-mercaptopicolinic acid.

    PubMed

    Blank, B; DiTullio, N W; Deviney, L; Roberts, J T; Saunders, H L

    1977-04-01

    A series of S-alkanoyl and benzoyl derivatives of 3-mercaptopicolinic acid (3-MPA) was prepared and studied for hypoglycemic activity. Three alkanoyl derivatives (propionyl, pivaloyl, and 1-adamantanecarbonyl, 19-21) were prepared with increasing bulk around the thio ester bond. The benzoyl derivatives contained aromatic substituents chosen from a sigma-pi cluster chart so that the esters prepared had a wide range of electronic and solubility properties. In general, compounds with substituents which increased lipid solubility [p-chlorobenzoyl (4), p-trifluoromethylbenzoyl (6), and pivaloyl (20)] had the greatest potency at a dose of 300 mg/kg. Hydrolysis rates, measured at pH 6 and 8, indicated that in vivo breakdown to 3-MPA probably did not account for the observed hypoglycemic activity of the esters. 4, 6, and 20 were less potent than 3-MPA in comparative dose range studies.

  7. Improved resistance of chemically-modified nanocellulose against thermally-induced depolymerization.

    PubMed

    Agustin, Melissa B; Nakatsubo, Fumiaki; Yano, Hiroyuki

    2017-05-15

    The study demonstrated the improvement in the resistance of nanocellulose against thermally-induced depolymerization by esterification with benzoyl (BNZ) and pivaloyl (PIV). The change in the degree of polymerization (DP) and molecular weight distribution (MWD) after thermal treatment in nitrogen and in air was investigated using viscometry and gel permeation chromatography. BNZ and PIV nanocellulose esters without α-hydrogens gave higher DP and narrower MWD than pure bacterial cellulose; and the acetyl and myristoyl esters, which possess α-hydrogens. Results also showed that when depolymerization is suppressed, thermal discoloration is also reduced. Resistance against depolymerization inhibits the formation of reducing ends which can be active sites for thermal discoloration. Finally, the findings suggest that benzoylation and pivaloylation can be an excellent modification technique to improve the thermal stability of nanocellulose.

  8. Ortho effect in electron ionization mass spectrometry of N-acylanilines bearing a proximal halo substituent.

    PubMed

    Jariwala, Freneil B; Figus, Margaret; Attygalle, Athula B

    2008-08-01

    Electron ionization (EI) mass spectra are not very helpful for characterizing ortho, meta, and para isomers of underivatized haloanilines since their spectra are virtually identical. In contrast, when the amino group of chloro-, bromo-, or iodoanilines is transformed to an N-formyl, N-acetyl, or N-benzoyl derivative, the spectra of the derivatives reveal a highly dramatic loss of a halogen radical, instead of an HX elimination usually expected from an "ortho effect." For example, the spectra of N-formyl, N-acetyl, and N-benzoyl derivatives of ortho isomers of chloro-, bromo-, and iodoanilines show a very prominent peak at m/z 120, 134, and 196, respectively, for the loss of the corresponding halogen atom.

  9. Minor pregnanes from Caralluma adscendens var. gracilis and Caralluma pauciflora.

    PubMed

    Reddy, Kommidi Devendar; Rao, Belvotagi Venkatrao Adavi; Babu, Gummadi Sridhar; Kumar, Bobbala Ravi; Braca, Alessandra; Vassallo, Antonio; De Tommasi, Nunziatina; Rao, Ghanakota Venkateshwar; Rao, Achanta Venkata Narasimha Appa

    2011-10-01

    Phytochemical investigation of Caralluma adscendens var. gracilis and Caralluma pauciflora (Asclepiadaceae) whole plant extracts allowed to isolate one pregnane glycoside and two pregnanes characterized as 12β,20-O-dibenzoyl-5α,6-dihydrosarcostin β-oleandropyranosyl-(1→4)-β-cymaropyranosyl-(1→4)-β-digitoxypyranosyl-(1→4)-β-cymaropyranosyl-(1→4)-β-cymaropyranoside (1), 12β-O-benzoyl-3β,11α,14β,20R-pentahydroxy-pregn-5-ene (2), and 11α-O-benzoyl-3β,12β,14β,20R-pentahydroxy-pregn-5-ene (3), respectively. Their structural characterization was obtained on the basis of extensive NMR spectral studies. Three known pregnane glycosides along with lupeol and β-sitosterol were also isolated and characterized.

  10. Mechanistic investigations aided by isotopic labeling. 10. Investigations of novel furan-2,3-dione rearrangements by oxygen-17 labeling

    SciTech Connect

    Kollenz, G.; Sterk, H.; Hutter, G. )

    1991-01-04

    The oxa 1,3-diene moiety in 4-benzoyl-5-phenylfuran-2,3-dione (1) adds aryl isocyanides or heterocumulenes via formal (4 + 1) or (4 + 2) cycloaddition processes. The unstable primary adducts undergo novel furandione rearrangements to intermediates in which the two oxygen atoms of the lactone moiety in (1) are equivalent. This equivalence was confirmed by {sup 17}O-labeling experiments using {sup 17}O NMR spectroscopic and mass spectroscopic measurements. Comparison of the {sup 17}O chemical shifts in (1), labeled either at the benzoyl and ring oxygens (1a-{sup 17}O) or at both exocyclic ring-carbonyl oxygens (1b-{sup 17}O), with those in the products (2-4) confirmed the proposed pathways of these rearrangements. Reactions involving carbodiimides, isocyanates, and ketene imines were investigated.

  11. Second monoclinic form of (E)-3-(4-fluoro­phen­yl)-1-phenyl­prop-2-en-1-one

    PubMed Central

    Arias-Ruiz, Saira N.; Romero, Nancy; Lobato-García, Carlos E.; Gómez-Rivera, Abraham; Mendoza, Angel

    2013-01-01

    The unit-cell dimensions and space group of the second monoclinic polymorph of the title compound, C15H11FO, differ from those of the previously reported form [Jing (2009 ▶). Acta Cryst. E65, o2515]. The title compound shows an E conformation of the C=C bond with the 4-fluoro­phenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluoro­phenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C—H⋯O and C—H⋯F inter­actions form a cross-linked packing motif, building sheets parallel to (-102). PMID:24454121

  12. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)

    DOEpatents

    Samsel, E.G.

    1992-10-20

    A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-[alpha]-benzoylamino-4boronocinnamic acid, asymmetrically hydrogenating the z-[alpha]-benzoylamino-4-boronocinnamic acid in the presence of a catalyst of a cheltate complex of rhodium (I) with chiral bisphosphines to form L-(+)-N-benzoyl-4-boronophenylalanine, and thereafter acidifying the L-(+)-N-benzoyl-4-boronophenylalanine in an organic medium to produce L-BPA. 3 figs.

  13. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)

    DOEpatents

    Samsel, Edward G.

    1992-01-01

    A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-.alpha.-benzoylamino-4-boronocinnamic acid, asymmetrically hydrogenating the z-.alpha.-benzoylamino-4-boronocinnamic acid in the presence of a catalyst of a cheltate complex of rhodium (I) with chiral bisphosphines to form L-(+)-N-benzoyl-4-boronophenylalanine, and thereafter acidifying the L-(+)-N-benzoyl-4-boronophenylalanine in an organic medium to produce L-BPA.

  14. 2-Chloro-N-(3,5-dichloro­phenyl)­benzamide

    PubMed Central

    Gowda, B. Thimme; Foro, Sabine; Sowmya, B. P.; Fuess, Hartmut

    2008-01-01

    The amide group in the structure of the title compound (N35DCP2CBA), C13H8Cl3NO, is trans-planar, similar to that observed in N-(3-chloro­phen­yl)benzamide, N-(3,5-dichloro­phen­yl)benzamide, 2-chloro-N-phenyl­benzamide and other benzanilides. The C=O bond in N35DCP2CBA is anti to the ortho-chloro substituent in the benzoyl ring. The amide group makes dihedral angles of 63.1 (12) and 31.1 (17)°, respectively, with the benzoyl and aniline benzene rings, while the dihedral angle between the two benzene rings is 32.1 (2)°. The mol­ecules are linked into chains along the b axis by N—H⋯O hydrogen bonds. PMID:21202924

  15. N-(3-Methyl-benzo-yl)-2-nitro-benzene-sulfonamide.

    PubMed

    Suchetan, P A; Foro, Sabine; Gowda, B Thimme

    2012-02-01

    In the title compound, C(14)H(12)N(2)O(5)S, the conformation between the N-H group and the ortho-nitro group in the sulfonyl benzene ring is syn and that between the C=O and meta-methyl groups in the benzoyl ring is anti. The mol-ecule is twisted at the S-N bond with a torsion angle of 64.3 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 75.73 (7)° and that between the sulfonyl and benzoyl benzene rings is 89.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

  16. Phloroglucinol and Terpenoid Derivatives from Hypericum cistifolium and H. galioides (Hypericaceae)

    PubMed Central

    Crockett, Sara L.; Kunert, Olaf; Pferschy-Wenzig, Eva-Maria; Jacob, Melissa; Schuehly, Wolfgang; Bauer, Rudolf

    2016-01-01

    A new simple phloroglucinol derivative characterized as 1-(6-hydroxy-2,4-dimethoxyphenyl)-2-methyl-1-propanone (1) was isolated from Hypericum cistifolium (Hypericaceae) as a major constituent of the non-polar plant extract. Minor amounts of this new compound, in addition to two known structurally related phloroglucinol derivatives (2 and 3), and two new terpenoid derivatives characterized, respectively, as 2-benzoyl-3,3-dimethyl-4R,6S-bis-(3-methylbut-2-enyl)-cyclohexanone (4a) and 2-benzoyl-3,3-dimethyl-4S,6R-bis-(3-methylbut-2-enyl)-cyclohexanone (4b), were isolated from a related species, H. galioides Lam. The chemical structures were established using 2D-NMR spectroscopy and mass spectrometry. These compounds were evaluated in vitro for antimicrobial activity against a panel of pathogenic microorganisms and anti-inflammatory activity through inhibition of COX-1, COX-2, and 5-LOX catalyzed LTB4 formation. PMID:27458464

  17. Computational study of the synthesis of benzoin derivatives from benzil

    NASA Astrophysics Data System (ADS)

    Topal, Kevser Göçmen; Unaleroglu, Canan; Aviyente, Viktorya

    Benzil (1,2-diphenylethane-1,2-dione) undergoes cyanide catalyzed condensation with benzaldehyde to yield O-benzoylated benzoin (2-benzoyl-1,2-diphenylethanone). In this study, the experimentally suggested mechanism has been modeled with PM3 and verified with B3LYP. The effect of the substituent on the reaction yield has been rationalized by considering two benzil derivatives; 1,2-bis(2-chlorophenyl)ethane-1,2-dione and 1,2-bis(2-fluorophenyl)ethane-1,2-dione and three benzaldehyde derivatives; o-fluorobenzaldehyde, o-methylbenzaldehyde and 2-pyridinecarboxaldehyde. The effect of the solvent has been modeled by using the isodensity-surface polarizable continuum (IPCM) model. Reactivity descriptors have been used to justify the reactivity differences of the various substituents.

  18. Enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines to unsaturated nitriles catalyzed by NiII-Pigiphos.

    PubMed

    Milosevic, Sandra; Togni, Antonio

    2013-10-04

    The asymmetric 1,3-dipolar cycloaddition reaction of C,N-cyclic azomethine imines with small unsaturated nitriles using a dicationic Ni(II) complex containing the chiral triphosphine ligand bis{(R)-1-[(Sp)-2-(diphenylphosphino)ferrocenyl]ethyl}cyclohexylphosphine [(R,Sp)-Pigiphos] as a catalyst has been developed. A variety of new chiral cyanopyrazolidines were obtained regio- and diastereoselectively in good to excellent yields with moderate to excellent enantioselectivities. Thus, N-benzoylimino-3,4-dihydro-6-methylisoquinolinium betaine (1a) reacts at RT with acrylonitrile in the presence of 1-5 mol % catalyst to afford 3,4-trans-1-benzoyl-4-cyano-2,3-(tetrahydroisoquinoline)tetrahydropyrazole (2a) in up to 84% yield and 98% ee. The regio- and stereoselectivity were confirmed in the case of compound 2a and 3,4-trans-1-benzoyl-4-cyano-2,3-(6-bromotetrahydroisoquinoline)tetrahydropyrazole (2e) by X-ray crystallography.

  19. 1,2-diketones promoted degradation of poly(epsilon-caprolactone)

    SciTech Connect

    Danko, Martin; Borska, Katarina; Ragab, Sherif Shaban; Janigova, Ivica; Mosnacek, Jaroslav

    2012-07-11

    Photochemical reactions of Benzil and Camphorquinone were used for modification of poly({epsilon}-caprolactone) polymer films. Photochemistry of dopants was followed by infrared spectroscopy, changes on polymer chains of matrix were followed by gel permeation chromatography. Benzoyl peroxide was efficiently photochemically generated from benzyl in solid polymer matrix in the presence of air. Following decomposition of benzoyl peroxide led to degradation of matrix. Photochemical transformation of benzil in vacuum led to hydrogen abstraction from the polymer chains in higher extent, which resulted to chains recombination and formation of gel. Photochemical transformation of camphorquinone to corresponding camphoric peroxide was not observed. Only decrease of molecular weight of polymer matrix doped with camphorquinone was observed during the irradiation.

  20. Benzaldehyde dehydrogenase from chitosan-treated Sorbus aucuparia cell cultures.

    PubMed

    Gaid, Mariam M; Sircar, Debabrata; Beuerle, Till; Mitra, Adinpunya; Beerhues, Ludger

    2009-09-01

    Cell cultures of Sorbus aucuparia respond to the addition of chitosan with the accumulation of the biphenyl phytoalexin aucuparin. The carbon skeleton of this inducible defense compound is formed by biphenyl synthase (BIS) from benzoyl-CoA and three molecules of malonyl-CoA. The formation of benzoyl-CoA proceeds via benzaldehyde as an intermediate. Benzaldehyde dehydrogenase (BD), which converts benzaldehyde into benzoic acid, was detected in cell-free extracts from S. aucuparia cell cultures. BD and BIS were induced by chitosan treatment. The preferred substrate for BD was benzaldehyde (K(m)=49 microM). Cinnamaldehyde and various hydroxybenzaldehydes were relatively poor substrates. BD activity was strictly dependent on the presence of NAD(+) as a cofactor (K(m)=67 microM).