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Sample records for phenyl p-fluorophenyl thienyl-2

  1. 1-(2-Thienyl)-2-phenylethylamines as potential non-stimulant anorectics.

    PubMed

    Mrongovius, R I; Ghosh, P; Bolt, A G; Ternai, B

    1981-01-01

    A series of 1-(2-thienyl)-2-phenylethylamines was synthesized and tested for anorectic and motor activity effects in rats. Phenyl ring substituents included Cl, Br, F, CF3, CH3, OCH3, and NO2; amino group substituents included alkyl, benzyl and acetyl groups. About half of the compounds produced significant anorexia; only one of these active anorectics increased motor activity. The three most potent non-stimulant anorectics were: 1-(2-thienyl)-2-(4-chlorophenyl)ethylamine, its N-isopropyl analogue, and N-isopropyl-1-(2-thienyl)-2-(4-fluorophenyl)ethylamine.

  2. Clarithromycin Susceptibility Testing of Mycobacterium avium Complex Using 2,3-Diphenyl-5-thienyl-(2)-tetrazolium Chloride Microplate Assay with Middlebrook 7H9 Broth

    PubMed Central

    Park, Young Kil; Koh, Won-Jung; Kim, Shin Ok; Shin, Sonya; Kim, Bum Joon; Cho, Sang-Nae; Lee, Sun Min

    2009-01-01

    A series of 119 Mycobacterium avium complex isolates were subjected to clarithromycin susceptibility testing using microplates containing 2,3-diphenyl-5-thienyl-(2)-tetrazolium chloride (STC). Among 119 isolates, 114 (95.8%) were susceptible to clarithromycin and 5 were resistant according to the new and the standard method. STC counts the low cost and reduces the number of procedures needed for susceptibility testing. PMID:19543518

  3. The syntheses of 1-(2-thienyl)-2-(methylamino) propane (methiopropamine) and its 3-thienyl isomer for use as reference standards.

    PubMed

    Angelov, D; O'Brien, J; Kavanagh, P

    2013-03-01

    1-(2-Thienyl)-2-(methylamino)propane (methiopropamine, MPA), the thiophene analogue of methamphetamine, has recently appeared on a number of websites offering 'legal highs' for sale and has also been reported as a new psychoactive substance by the European Monitoring Centre for Drugs and Drugs Addiction (EMCDDA) Early Warning System. The drug is currently not controlled in the European Union (EU) but it would be expected that forensic laboratories will encounter it during routine analysis. As no reference standard was available, we have established a three-step protocol for its synthesis. We have also synthesized its 3-thienyl isomer and have established that this is separable from methiopropamine by gas chromatography using one of our routine protocols. The synthetic methodology presented here could be readily extended to the syntheses of analogous compounds.

  4. Interactions of diorganolead(IV) with 3-(2-thienyl)-2-sulfanylpropenoic acid and/or thiamine: chemical and in vitro and in vivo toxicological results.

    PubMed

    Casas, José S; Castaño, M Victoria; Sánchez, Agustín; Sordo, José; Torres, M Dolores; Couce, María D; Gato, Angeles; Alvarez-Lorenzo, Carmen; Camiña, M Félix; Castellano, Eduardo E

    2010-03-01

    The reactions of PbR(2)(OAc)(2) (R = Me, Ph) with 3-(2-thienyl)-2-sulfanylpropenoic acid (H(2)tspa) in methanol or ethanol afforded complexes [PbR(2)(tspa)] that electrospray ionization-mass spectrometry (ESI-MS) and IR data suggest are polymeric. X-ray studies showed that [PbPh(2)(tspa)(dmso)] x dmso, crystallized from a solution of [PbPh(2)(tspa)] in dmso, is dimeric, and that [HQ](2)[PbPh(2)(tspa)(2)] (Q = diisopropylamine), obtained after removal of [PbPh(2)(tspa)] from a reaction including Q, contains the monomeric anion [PbPh(2)(tspa)(2)](2-). In the solid state the lead atoms are O,S-chelated by the tspa(2-) ligands in all these products, and in the latter two have distorted octahedral coordination environments. NMR data suggest that tspa(2-) remains coordinated to PbR(2)(2+) in solution in dmso. Neither thiamine nor thiamine diphosphate reacted with PbMe(2)(NO(3))(2) in D(2)O. Prior addition of H(2)tspa protected LLC-PK1 renal proximal tubule cells against PbMe(2)(NO(3))(2); thiamine had no statistically significant effect by itself, but greatly potentiated the action of H(2)tspa. Administration of either H(2)tspa or thiamine to male albino Sprague-Dawley rats dosed 30 min previously with PbMe(2)(NO(3))(2) was associated with reduced inhibition of delta-ALAD by the organolead compound, and with lower lead levels in kidney and brain, but joint administration of both H(2)tspa and thiamine only lowered lead concentration in the kidney.

  5. 1-Phenyl­isatin

    PubMed Central

    Shukla, Deepak; Rajeswaran, Manju

    2011-01-01

    In the title compound, C14H9NO2, the phenyl ring makes a dihedral angle of 50.59 (5)° with the mean plane of the isatin fragment. In the crystal, mol­ecules are linked through weak inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits two slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.968 (3) Å, inter­planar distance = 3.484 (3) Å and slippage = 1.899 (3) Å], and between the phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.968 (3) Å, inter­planar distance = 3.638 (3) Å and slippage = 1.584 (3) Å]. PMID:22091062

  6. Phenylated Polyimides With Greater Solubility

    NASA Technical Reports Server (NTRS)

    Harris, Frank W.

    1991-01-01

    In experiments, 3,6-diphenylpyromellitic dianhydride monomer prepared and polymerized with several different diamines. Polyimides with pendent phenyl groups along polymer backbones considerably more soluble than PMDA-based materials. Increased solubility eases processing, providing increased potential use in variety of applications. Because most polymers soluble in organic solvents, usable in microelectronics applications. Excellent thermal stabilities and high transition temperatures make them ideally suited. Many polymers extremely rigid and useful as reinforcing polymers in molecular composites. More flexible compositions useful as matrix resins in carbon-reinforced composites.

  7. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  8. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  9. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  10. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  11. Testing Consent Order on Dilsodecyl Phenyl Phosphite

    EPA Pesticide Factsheets

    This rule announces that EPA has signed an enforceable Testing Consent Order with three manufacturers of dilsodecyl phenyl phosphite (PDDP CAS No, 25550-98-5), who have agreed to perform certain neurotoxicity tests PDDP.

  12. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.3063 Substituted phenyl azo substituted phenyl esters (generic name). Link to an amendment published at 79 FR 34637, June 18, 2014. (a)...

  13. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  14. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  15. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  16. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  17. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phenyl azo dye (generic). 721.5917... Substances § 721.5917 Phenyl azo dye (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a phenyl azo dye (PMN P-02-17) is subject...

  18. 40 CFR 721.536 - Halogenated phenyl alkane.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Halogenated phenyl alkane. 721.536... Substances § 721.536 Halogenated phenyl alkane. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as halogenated phenyl alkane (PMN P-89-867)...

  19. Ultraviolet photodissociation dynamics of the phenyl radical

    SciTech Connect

    Song Yu; Lucas, Michael; Alcaraz, Maria; Zhang Jingsong; Brazier, Christopher

    2012-01-28

    Ultraviolet (UV) photodissociation dynamics of jet-cooled phenyl radicals (C{sub 6}H{sub 5} and C{sub 6}D{sub 5}) are studied in the photolysis wavelength region of 215-268 nm using high-n Rydberg atom time-of-flight and resonance enhanced multiphoton ionization techniques. The phenyl radicals are produced from 193-nm photolysis of chlorobenzene and bromobenzene precursors. The H-atom photofragment yield spectra have a broad peak centered around 235 nm and are in good agreement with the UV absorption spectra of phenyl. The H + C{sub 6}H{sub 4} product translational energy distributions, P(E{sub T})'s, peak near {approx}7 kcal/mol, and the fraction of average translational energy in the total excess energy, , is in the range of 0.20-0.35 from 215 to 268 nm. The H-atom product angular distribution is isotropic. The dissociation rates are in the range of 10{sup 7}-10{sup 8} s{sup -1} with internal energy from 30 to 46 kcal/mol above the threshold of the lowest energy channel H +o-C{sub 6}H{sub 4} (ortho-benzyne), comparable with the rates from the Rice-Ramsperger-Kassel-Marcus theory. The results from the fully deuterated phenyl radical are identical. The dissociation mechanism is consistent with production of H +o-C{sub 6}H{sub 4}, as the main channel from unimolecular decomposition of the ground electronic state phenyl radical following internal conversion of the electronically excited state.

  20. Rotational spectra and conformational structures of 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone.

    PubMed

    Tubergen, M J; Lavrich, R J; Plusquellic, D F; Suenram, R D

    2006-12-14

    Microwave spectra have been recorded for 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone from 11 to 24 GHz using a Fourier-transform microwave spectrometer. Only one spectrum from a single conformational isomer was observed for each species. The rotational transitions in the spectrum of 1-phenyl-2-propanone were split into separate transitions arising from the A- and E-torsional levels of the methyl rotor. The fit of the E-state transitions to a "high-barrier" internal rotation Hamiltonian determines V3 = 238(1) cm-1 and rotor-axis angles of thetaa = 87.7(5) degrees, thetab = 50.0(5) degrees, and thetac = 40.0(5) degrees. Ab initio optimizations (MP2/6-31G**) and single-point calculations (MP2/6-311++G**) were used to model the structures of 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone. The lowest energy conformations of these species were found to be stabilized by weak OH-pi, NH-pi, and CH-pi hydrogen-bonding interactions. Moments of inertia, derived from the model structures, were used to assign the spectra to the lowest energy conformation of each species. A series of MP2/6-31G* partial optimizations along the internal rotation pathway were used to estimate the barrier to methyl rotation to be 355 cm-1 for 1-phenyl-2-propanone.

  1. 2-Amino-N′-phenyl­benzohydrazide

    PubMed Central

    Kesternich, Víctor; Gahona, Paulo; Pérez-Fehrmann, Marcia; Brito, Iván; López-Rodríguez, Matías

    2012-01-01

    In the title compound, C13H13N3O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains parallel to the c axis. Neighbouring chains are linked by weak N—H⋯N hydrogen bonds, forming R 4 4(20) rings, and resulting in the formation of a two-dimensional network lying parallel to (010). The packing also features π–π stacking inter­actions between phenyl rings [centroid–centroid distance = 3.803 (2) Å]. PMID:22719614

  2. S-Phenyl benzothio-ate.

    PubMed

    Belay, Yonas H; Kinfe, Henok H; Muller, Alfred

    2012-10-01

    In the title compound, C(13)H(10)OS, the phenyl rings are inclined to one another by 51.12 (8)°. There is a short C-H⋯S contact in the molecule.In the crystal, molecules are linked via C-H⋯O hydrogen bonds forming chains along the a axis. Molecules are also linked by C-H⋯π and weak π-π interactions [centroid-centroid distance = 3.9543 (10) Å].

  3. Phenyl valerate esterase activity of human butyrylcholinesterase.

    PubMed

    Mangas, Iris; Vilanova, Eugenio; Estévez, Jorge

    2017-03-15

    Phenyl valerate is used for detecting and measuring neuropathy target esterase (NTE) and has been used for discriminating esterases as potential target in hen model of organophosphorus delayed neuropathy. In previous studies we observed that phenyl valerate esterase (PVase) activity of an enzymatic fraction in chicken brain might be due to a butyrylcholinesterase protein (BuChE), and it was suggested that this enzymatic fraction could be related to the potentiation/promotion phenomenon of the organophosphate-induced delayed neuropathy (OPIDN). In this work, PVase activity of purified human butyrylcholinesterase (hBuChE) is demonstrated and confirms the novel observation that a relationship of BuChE with PVase activities is also relevant for humans, as is, therefore the potential role in toxicity for humans. The KM and catalytic constant (kcat) were estimated as 0.52/0.72 µM and 45,900/49,200 min(-1) respectively. Furthermore, this work studies the inhibition by preincubation of PVase and cholinesterase activities of hBuChE with irreversible inhibitors (mipafox, iso-OMPA or PMSF), showing that these inhibitors interact similarly in both activities with similar second-order inhibition constants. Acethylthiocholine and phenyl valerate partly inhibit PVase and cholinesterase activities, respectively. All these observations suggest that both activities occur in the same active center. The interaction with a reversible inhibitor (ethopropazine) showed that the cholinesterase activity was more sensitive than the PVase activity, showing that the sensitivity for this reversible inhibitor is affected by the nature of the substrate. The present work definitively establishes the capacity of BuChE to hydrolyze the carboxylester phenyl valerate using a purified enzyme (hBuChE). Therefore, BuChE should be considered in the research of organophosphorus targets of toxicity related with PVase proteins.

  4. Epoxy resin cure. [Phenyl glycidyl ether

    SciTech Connect

    Smith, R.E.; Woodburn, G.L.

    1986-07-01

    The reactions that occur between the model epoxy, phenyl glycidyl ether, and the cure agent dicyandiamide (DICY) have been investigated using nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), gel permeation chromatography (GPC), and high-performance liquid chromatography (HPLC) techniques. It is shown that the reaction at 130/sup 0/C requires 90 min for completion when catalyzed by boron trifluoride monoethyl amine (BF/sub 3/-MEA). At least three major products are formed. The identity of these products is based on previously published spectroscopic data. 3 refs., 5 figs.

  5. Chemistry of polycyclic aromatic hydrocarbons formation from phenyl radical pyrolysis and reaction of phenyl and acetylene.

    PubMed

    Comandini, A; Malewicki, T; Brezinsky, K

    2012-03-15

    An experimental investigation of phenyl radical pyrolysis and the phenyl radical + acetylene reaction has been performed to clarify the role of different reaction mechanisms involved in the formation and growth of polycyclic aromatic hydrocarbons (PAHs) serving as precursors for soot formation. Experiments were conducted using GC/GC-MS diagnostics coupled to the high-pressure single-pulse shock tube present at the University of Illinois at Chicago. For the first time, comprehensive speciation of the major stable products, including small hydrocarbons and large PAH intermediates, was obtained over a wide range of pressures (25-60 atm) and temperatures (900-1800 K) which encompass the typical conditions in modern combustion devices. The experimental results were used to validate a comprehensive chemical kinetic model which provides relevant information on the chemistry associated with the formation of PAH compounds. In particular, the modeling results indicate that the o-benzyne chemistry is a key factor in the formation of multi-ring intermediates in phenyl radical pyrolysis. On the other hand, the PAHs from the phenyl + acetylene reaction are formed mainly through recombination between single-ring aromatics and through the hydrogen abstraction/acetylene addition mechanism. Polymerization is the common dominant process at high temperature conditions.

  6. Synthesis of Phenyl-Adducted Cyclodextrin through the Click Reaction

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A new derivative of ß-cyclodextrin (CD) has been made incorporating the phenyl group through the use of click reaction. The resulting product exhibits a self-association phenomenon through the formation of inclusion compound between the phenyl group and CD. The product has been characterized by 1H...

  7. The effect of bromine scanning around the phenyl group of 4-phenyl­quinolone derivatives

    PubMed Central

    Steiger, Scott A.; Monacelli, Anthony J.; Li, Chun; Hunting, Janet L.; Natale, Nicholas R.

    2014-01-01

    Three quinolone compounds were synthesized and crystallized in an effort to study the structure–activity relationship of these calcium-channel antagonists. In all three quinolones, viz. ethyl 4-(4-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate, (I), ethyl 4-(3-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-car­box­yl­ate, (II), and ethyl 4-(2-bromo­phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate, (III), all C21H24BrNO3, common structural features such as a flat boat conformation of the 1,4-di­hydro­pyridine (1,4-DHP) ring, an envelope conformation of the fused cyclo­hexa­none ring and a bromo­phenyl ring at the pseudo-axial position and orthogonal to the 1,4-DHP ring are retained. However, due to the different packing inter­actions in each compound, halogen bonds are observed in (I) and (III). Compound (III) crystallizes with two molecules in the asymmetric unit. All of the prepared derivatives satisfy the basic structural requirements to possess moderate activity as calcium-channel antagonists. PMID:25093361

  8. Bis (4-(3,4-dimethylene-pyrrolidyl)-phenyl) methane

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M. (Inventor)

    1990-01-01

    The primary objective is to prepare high temperature polymeric materials, especially linear aromatic polyimides, which maintain their integrity and toughness during long exposure times at elevated temperatures. The attained benefits are obtained by first providing the bis (exocyclodiene) bis (4-(3,4-dimethylene-pyrrolidyl)-phenyl) methane, which is a novel material formed from the monomer N-phenyl-3,4-dimethylene-pyrrolidine. This compound undergoes Diels-Alder reaction with a bismaleimide, without the evolution of gaseous by-products, to form the aromatic polyimide bis (4-(3,4-dimethylene-pyrrolidyl)-phenyl) methane.

  9. Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids.

    PubMed

    Huang, Ling; Su, Tao; Shan, Wenjun; Luo, Zonghua; Sun, Yang; He, Feng; Li, Xingshu

    2012-05-01

    A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC(50) value of 0.017 μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD.

  10. Fragrance material review on ethyl phenyl carbinyl acetate.

    PubMed

    McGinty, D; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of ethyl phenyl carbinyl acetate when used as a fragrance ingredient is presented. Ethyl phenyl carbinyl acetate is a member of the fragrance structural group Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). The AAASAE fragrance ingredients are prepared by reacting an aryl alkyl alcohol with a simple carboxylic acid (a chain of 1-4 carbons) to generate formate, acetate, propionate, butyrate, isobutyrate and carbonate esters. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for ethyl phenyl carbinyl acetate were evaluated, then summarized, and includes: physical properties; acute toxicity; skin irritation; and skin sensitization data. A safety assessment of the entire AAASAE will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all AAASAE in fragrances.

  11. Bis(4-(3,4-dimethylenepyrrolidyl)-phenyl) methane

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M. (Inventor)

    1989-01-01

    It is the primary object of the present invention to prepare high temperature polymeric materials, especially linear aromatic polyimides, which maintain their integrity and toughness during long exposure times at elevated temperatures. According to the present invention, this object is achieved, and the attending benefits are obtained, by first providing the bis(exocyclodiene) bis(4-(3,4-dinethylene pyrrolidyl) phenyl) methane, which is formed from the monomer N-phenyl 3,4-dimethylene pyrrolidine. This bis-(exocyclodiene) undergoes Diels-Alder reaction with a bismaleimide without the evolution of gaseous by-products, to form the aromatic polyimide.

  12. 40 CFR 721.9825 - Phenyl substituted triazolinones.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... in combination with a chemical-resistant glove that has been demonstrated (EPA review not required... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9825 Phenyl substituted triazolinones. (a) Chemical substance and significant new...

  13. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  14. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  15. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL....-phenyl-, ethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester (PMN...

  16. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  17. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  18. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  19. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  20. 40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN...

  1. Chemically induced Parkinson's disease: intermediates in the oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine to the 1-methyl-4-phenyl-pyridinium ion

    SciTech Connect

    Chacon, J.N.; Chedekel, M.R.; Land, E.J.; Truscott, T.G.

    1987-04-29

    Various unstable intermediate oxidation states have been postulated in the metabolic activation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine to the 1-methyl-4-phenyl pyridinium ion. We now report the first direct observation of these free radical intermediates by pulse radiolysis and flash photolysis. Studies are described of various reactions of such species, in particular with dopamine whose autoxidation to dopamine quinone is reported to be potentiated by 1-methyl-4-phenyl-1,2,3, 6-tetrahydropyridine.

  2. Surfactant composition containing alkylated biphenylyl phenyl ether sulfonates

    SciTech Connect

    Hinkamp, P. E.

    1984-09-04

    The title compounds are of the formula (R)Y, (((R)X,(M(+)(-)O35-)A-Phenyl)-), (((R)Z, (M (+)(-)O35-)C-Phenyl)-O-)Benzene R is an alkyl radical of at least 6 carbon atoms and each R can be the same or different; M(+) is hydrogen, alkali metal ion, alkaline earth metal ion or ammonium ion radical and each M(+) can be the same or different; a, b and c are individually integers of 0 or 1 with the proviso that the ..sigma..(a+b+c) is equal to 2 or 3; and x, y and z are individually integers of 0-2 with the proviso that ..sigma..(x+y+z)greater than or equal to1. These compounds demonstrate good tolerance to multivalent cations, such as the cations of calcium and magnesium, good resistance to hydrolysis and are useful surfactants in enhanced oil recovery processes.

  3. Synthesis and Modification of Carboxylated Polyphenylenes and Phenylated Polyimides

    DTIC Science & Technology

    1976-03-01

    Aromatic ionomers , Polypyridine, Phenylated polyimides. Acetylene-terminated polyphenylenes, >Thermally-stable polymers. 20. AB8Jj«ACT (Continue on...barium salts to afford a series of aromatic ionomers ^ All but one of the potassium ionomers are soluble in dimethylsulfoxide andrcan be cast into...thin films that tough, flexible, water white, and transparent.Uiie magnesium and barium ionomers are insoluble in common organic solvents)>rhermo

  4. Oxygen Substituent Effects in the Pyrolysis of Phenethyl Phenyl Ethers

    SciTech Connect

    Britt, Phillip F; Kidder, Michelle; Buchanan III, A C

    2007-01-01

    The dominant structural linkage in the abundant renewable energy resource, lignin, is the arylglycerol-{beta}-aryl ether commonly referred to as the {beta}-O-4 linkage. The simplest representation of this linkage, unadorned by substituents, is phenethyl phenyl ether (PhCH{sub 2}CH{sub 2}OPh; PPE). Our prior detailed kinetic studies of the pyrolysis of PPE at 330-425 C showed that a free-radical chain mechanism is involved that cycles through radicals formed at both the {alpha}- and {beta}-carbons. The previously unrecognized competing path involving rearrangement of the {beta}-carbon radical by an O,C-phenyl shift accounts for ca. 25% of the products. In this paper, we explore the effect of aromatic hydroxy and methoxy substituents on both the rate and product selectivity for the pyrolysis of these more complex lignin model compounds. The pyrolysis reactions are conducted in biphenyl solvent at 345 C and low conversions to minimize secondary reactions. The pyrolysis rates were found to vary substantially as a function of the substitution pattern. The rearrangement path involving the {beta}-carbon radical and O,C-phenyl shift was found to remain important in all the molecules investigated, and the selectivity for this path also showed a dependence on the substitution pattern.

  5. Separation optimization for the recovery of phenyl ethyl alcohol.

    PubMed

    Priddy, S A; Hanley, T R; Effler, W T

    1999-01-01

    Phenyl ethyl alcohol is a compound that occurs naturally in flower petals and in many common beverages, such as beer. Desire for the floral, rose-like notes imparted by phenyl ethyl alcohol has created a unique niche for this chemical in flavor and fragrance industries. Phenyl ethyl alcohol can be produced by Saccharomyces cerevisiae via bioconversion. Often this method of production results in extremely low yields, thus placing a great deal of importance on recovery and purification of the valuable metabolite. To determine the best method for recovering the chemical, a primary recovery step and a secondary recovery step were developed. The primary recovery step consisted of comparing dead-end filtration with crossflow ultrafiltration. Crossflow ultrafiltration was ultimately selected to filter the fermentation broth because of its high flow rates and low affinity for the product. The secondary recovery step consisted of a comparison of liquid- liquid extraction and hydrophobic resin recovery. The hydrophobic resin was selected because of its higher rate of recovery and a higher purity than the liquid-liquid extraction, the current practice of Brown-Forman.

  6. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 1,4-Benzenediamine, Nâ²-(alkyl)-N- phenyl]-N-phenyl- (generic). 721.10349 Section 721.10349 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N-...

  7. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 1,4-Benzenediamine, Nâ²-(alkyl)-N- phenyl]-N-phenyl- (generic). 721.10349 Section 721.10349 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N-...

  8. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 1,4-Benzenediamine, Nâ²-(alkyl)-N- phenyl]-N-phenyl- (generic). 721.10349 Section 721.10349 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N-...

  9. Catalytic reaction of 3-phenyl-2-propyn-1-ol with alcohols

    SciTech Connect

    Grigoryan, S.G.; Avetisyan, K.G.; Matnishyan, A.A.

    1987-01-10

    The cyclic ketal 2,5-dimethyl-2,5-bis(3-phenyl-2-propynyloxy)-1,4-dioxane was obtained by the reaction of 3-phenyl-2-propyn-1=ol with propargyl alcohol in the presence of the HgO-BF/sub 3/ O(C/sub 2/H/sub 5/)/sub 2/ catalytic system. The transformation of 3-phenyl-2-propyn-1-ol and its ethers in methanol and ethanol by the action of the above-mentioned catalytic system leads to 1-phenyl-3-alkoxy-1-propanone, 1-phenyl-1,1,3-trialkoxypropane, and 1-phenyl-2-propen-1-one. The intermediate organomercury compound, which is the product from regioselective addition of mercuric oxide and the saturated alcohol at the triple bond, was isolated. Its protodemercuration led to the above-mentioned linear products. The formation of the cyclic ketal is presumably due to the preferred formation of mercury bis-hydroxypropargylide.

  10. Phase transformation of calcium phenyl phosphate in calcium hydroxyapatite

    SciTech Connect

    Tanaka, Hidekazu . E-mail: hidekazu@riko.shimane-u.ac.jp; Ibaraki, Koshiro; Uemura, Masao; Hino, Ryozi; Kandori, Kazuhiko; Ishikawa, Tatsuo

    2007-07-03

    Calcium phenyl phosphate (CaPP) was synthesized from a mixture of Ca(OH){sub 2} and phenyl phosphate (C{sub 6}H{sub 5}PO{sub 4}H{sub 2}) in an aqueous media. XRD pattern of CaPP exhibited five diffraction peaks at 2{theta} = 6.6, 13.3, 20.0, 26.8 and 33.7{sup o}. The d-spacing ratio of these peaks was ca. 1:1/2:1/3:1/4:1/5. The molar ratios of Ca/P and phenyl/P of CaPP were 1.0 and 0.92, respectively, and the chemical formula of the material was expressed as (C{sub 6}H{sub 5}PO{sub 4}){sub 0.92}(HPO{sub 4}){sub 0.08}Ca.1.3H{sub 2}O, similar to that of dicalcium phosphate dihydrate (CaHPO{sub 4}.2H{sub 2}O: DCPD). These results allowed us to infer that CaPP is composed of a multilayer alternating bilayer of phenyl groups of the phosphates and DCPD-like phase. The structure of the material was essentially not altered after aging at pH 9.0-11.0 and 85 deg. C in an aqueous media. While, after aging at pH {<=}8.0, the diffraction peaks of CaPP were suddenly weakened and disappeared at pH 7.0. Besides, new peaks due to calcium hydroxyapatite (Ca{sub 10}(PO{sub 4}){sub 6}(OH){sub 2}: Hap) appeared and their intensity was strengthened with decreasing the solution pH. TEM observation revealed that the Hap particles formed at pH 6.0 are fibrous with ca. 1.5 {mu}m in length and ca. 0.2 {mu}m in width. From these results, it is presumed that the layered CaPP was dissolved, hydrolyzed and reprecipitated to fibrous Hap particles at pH {<=}8.0 and 85 deg. C in aqueous media. This phase transformation of CaPP in Hap resembled to the formation mechanism of Hap in animal organism.

  11. Acute Oral Toxicity Potential of 4-Nitrophenyl Methkyl Phenyl Phosphinate.

    DTIC Science & Technology

    1982-09-01

    methyl phenyl phosphinate Chemical Abstract Service Registry No.: None Molecular structure: C Ii NO P 13 12 4 .0 0~ NO., CH3 o o...C 56.33 56.17 H 4.36 4.28 N 5.05 5.14 P 11.17 11.25 2. Chemical Name: Polysorbate 80 (Tween 80) Chemical Abstract Service Registry No.: 9005-65-6...administration particularly in chronic toxicity studies in experimental data. 3. Chemical Name: Citric Acid, monohydrate Chemical Abstract Service

  12. Thermolysis of surface-immobilized phenethyl phenyl ether

    SciTech Connect

    Britt, P.F.; Buchanan, A.C. III; Hitsman, V.M.

    1991-01-01

    Our research has focused on modeling the constraints on free-radical reactions that might be imposed in coal as a consequence of its cross-linked macromolecular structure by covalently bonding diphenylalkanes to an inert silica surface. A surface-immobilized phenethyl phenyl ether ({approx}PhCH{sub 2}CH{sub 2}POh, or {approx}PPE-3) has been prepared as a model for ether linkages in lignin by the condensation of p-HOPhCH{sub 2}CH{sub 2}OPh with the surface hydroxyls of a high purity fumed silica. Thermolysis of {approx}PPE-3 at saturation surface coverage at 375{degree}C produces {approx}PhCH = CH{sub 2} and PhOH as the major products which are consistent with the proposed free-radical chain mechanism for the decomposition of fluid-phase phenethyl phenyl ether. However, significant quantities of {approx}PhCH{sub 3} and PhCHO (ca. 18% of the products) are produced indicating the emergence of a new reaction pathway on the surface. The mechanism for the decomposition of {approx}PPE-3 will be discussed in light of this new information. 18 refs., 1 fig.

  13. Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.

    PubMed

    Lapin, I

    2001-01-01

    Phenibut (beta-phenyl-gamma-aminobutyric acid HCl) is a neuropsychotropic drug that was discovered and introduced into clinical practice in Russia in the 1960s. It has anxiolytic and nootropic (cognition enhancing) effects. It acts as a GABA-mimetic, primarily at GABA(B) and, to some extent, at GABA(A) receptors. It also stimulates dopamine receptors and antagonizes beta-phenethylamine (PEA), a putative endogenous anxiogenic. The psychopharmacological activity of phenibut is similar to that of baclofen, a p-Cl-derivative of phenibut. This article reviews the structure-activity relationship of phenibut and its derivatives. Emphasis is placed on the importance of the position of the phenyl ring, the role of the carboxyl group, and the activity of optical isomers. Comparison of phenibut with piracetam and diazepam reveals similarities and differences in their pharmacological and clinical effects. Phenibut is widely used in Russia to relieve tension, anxiety, and fear, to improve sleep in psychosomatic or neurotic patients; as well as a pre- or post-operative medication. It is also used in the therapy of disorders characterized by asthenia and depression, as well as in post-traumatic stress, stuttering and vestibular disorders.

  14. 6-Butyryl-5-hy-droxy-4-phenyl-seselin.

    PubMed

    Aree, Thammarat; Tip-Pyang, Santi; Sowanthip, Preecha

    2010-08-28

    IN THE TITLE COUMARIN COMPOUND (SYSTEMATIC NAME: 6-butyryl-5-hy-droxy-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b;3,4-b']dipyran-2-one), C(24)H(22)O(5), also known as mammea A/AC cyclo D, the chromene and pyran rings are almost coplanar with a maximum deviation from the mean plane of 0.295 (2) Å. The attached phenyl group is inclined at 53.49 (8)° with respect to the chromene ring. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are linked into sheets parallel to (101) by inter-molecular C-H⋯O hydrogen bonds. Adjacent sheets are sustained by inter-molecular C-H⋯π and π-π [centroid-centroid distance = 4.471 (2) Å] inter-actions.

  15. Organophosphazenes. 18. Friedel-Crafts Phenylation Reactions of Alkyl and Nimethylamino Fluorocyclotriphosphazenes.

    DTIC Science & Technology

    1984-11-15

    ag, o.. a RIM COMAS.,A, Organophosphazenes, 18 . Friedel-Crafts Technical Report Phenylation Reactions of Alkyl and Nimethylaming...Organophosphatenes. 18 . Frliedel-Crafts Phenylation Reactions of Alkyl and Dimethylauino Fluorocyclotriphoaphazenes Christopher Wf. Allen, Scott...intensities were .................. .... . - ..-...--. - . . * -..-....- °.- 6 corrected accordingly. The structure was solved by direct methods (MULTAN80) 18

  16. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  17. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  18. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  19. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  20. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  1. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  2. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  3. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  4. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new...

  5. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  6. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  7. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  8. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  9. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  10. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  11. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  12. 40 CFR 721.1555 - Substituted phenyl azo substituted benzenediazonium salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... benzenediazonium salt. 721.1555 Section 721.1555 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1555 Substituted phenyl azo substituted benzenediazonium salt. (a... generically as a substituted phenyl azo substituted benzenediazonium salt (PMN P-92-652) is subject...

  13. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  14. 40 CFR 721.9545 - Substituted phenyl azo substituted sulfocarbopolycle, sodium salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... sulfocarbopolycle, sodium salt. 721.9545 Section 721.9545 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.9545 Substituted phenyl azo substituted sulfocarbopolycle, sodium salt... identified generically as a substituted phenyl azo substituted sulfocarbopolycle, sodium salt (PMN...

  15. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is...

  16. Synthesis, antitubercular, antifungal and antibacterial activities of 6-substituted phenyl-2-(3'-substituted phenyl pyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one.

    PubMed

    Islam, Mojahidul; Siddiqui, Anees A; Rajesh, Ramadoss

    2008-01-01

    A series of 6-substituted phenyl-2-(3'-substituted phenyl pyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-ones has been synthesized. An appropriate aromatic hydrocarbon reacts with succinic anhydride in presence of AlCl3 to yield beta-aroyl propionic acid. The corresponding acid was cyclized with hydrazine hydrate to give 6-(substituted aryl)-2,3,4,5-tetrahydro-3-pyridazinone, which was heated on steam bath with phosphorus(V) oxychloride to yield 3-chloro 6-substituted phenyl pyridazine. This intermediate after reaction with hydrazine hydrate was converted into 3-hydrazino-6-substituted phenyl pyridazine. The resulting product was converted into 6-substituted phenyl-2-(3'-substituted phenyl pyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one by reacting with substituted aroyl propionic acid. Spectral data (IR, NMR, mass spectra) confirmed the structures of the synthesized compounds. The synthesized compounds were investigated for their in vitro antitubercular, antifungal and antibacterial activities. The results indicated that the synthesized compounds have mild to potent activities with reference to their appropriate reference standards.

  17. Enhanced biological activity of carotenoids stabilized by phenyl groups.

    PubMed

    You, Ji Suk; Jeon, Sunhwa; Byun, Youn Jung; Koo, Sangho; Choi, Shin Sik

    2015-06-15

    Carotenoids are lipid soluble food ingredients with multifunction including antioxidant and anticancer activities. However, carotenoids are destructively oxidized upon reaction with radicals resulting in toxic effects on biological systems. Two synthetic carotenoids (BAS and BTS) containing the aromatic phenyl groups with a para-substituent (OMe and Me, respectively) at C-13 and C-13' position were prepared in order to overcome a structural instability of carotenoid. Both BAS and BTS exerted stronger radical scavenging activity than β-carotene in DPPH and ABTS assays. In particular, BTS significantly reduced in vivo ROS (reactive oxygen species) levels and improved body growth and reproduction of Caenorhabditiselegans. BTS has a great potential for the advanced and modified carotenoid material with stability leading to enhanced bioavailability.

  18. Novel nonsecosteroidal VDR agonists with phenyl-pyrrolyl pentane skeleton.

    PubMed

    Shen, Wei; Xue, Jingwei; Zhao, Zekai; Zhang, Can

    2013-11-01

    In order to find the vitamin D receptor (VDR) ligand whose VDR agonistic activity is separated from the calcemic activity sufficiently, novel nonsecosteroidal analogs with phenyl-pyrrolyl pentane skeleton were synthesized and evaluated for the VDR binding affinity, antiproliferative activity in vitro and serum calcium raising ability in vivo (tacalcitol used as control). Among them, several compounds showed varying degrees of VDR agonistic and growth inhibition activities of the tested cell lines. The most effective compound 2g (EC₅₀: 1.06 nM) exhibited stronger VDR agonistic activity than tacalcitol (EC₅₀: 7.05 nM), inhibited the proliferations of HaCaT and MCF-7 cells with IC₅₀ of 2.06 μM and 0.307 μM (tacalcitol: 2.07 μM and 0.057 μM) and showed no significant effect on serum calcium.

  19. Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.

    PubMed

    Fobofou, Serge Alain Tanemossu; Harmon, Chelsea Rebecca; Lonfouo, Antoine Honoré Nkuete; Franke, Katrin; Wright, Stephen M; Wessjohann, Ludger A

    2016-04-01

    In search for new or chemo-taxonomically relevant bioactive compounds from chemically unexplored Hypericum species, four previously undescribed natural products, named peplidiforones A-D were isolated and characterized from Hypericum peplidifolium A. Rich., together with six known compounds. The structures of all compounds were elucidated by extensive 1D- and 2D-NMR experiments, high resolution mass spectrometric analyses (HR-MS), and by comparison with data reported in the literature. Seven of these compounds are phenyl polyketides while three are acylphloroglucinol type compounds. Peplidiforone C, which possesses an unusual carbon skeleton consisting of a furan ring substituted by a 2,2-dimethylbut-3-enoyl moiety, is the first example of a prenylated furan derivative isolated from the genus Hypericum. The cytotoxicity, antifungal, and anti-herpes simplex virus type 1 (HSV-1) activities of extracts and compounds are described.

  20. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  1. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  2. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  3. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  4. 40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section...

  5. 40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl)oxy]carbonyl] amino]phenyl]amino...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ....- carbonyl] amino]phenyl]amino]carbonyl]- .omega.-methoxy-(generic). 721.10409 Section 721.10409 Protection...(oxyalkylenediyl), .alpha.- carbonyl] amino]phenyl]amino]carbonyl]- .omega.-methoxy-(generic). (a) Chemical... as poly(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN...

  6. 40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino]phenyl]amino...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ....- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (generic). 721.10409 Section 721.10409 Protection...(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (generic). (a) Chemical... as poly(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN...

  7. Complete assignment of NMR data of 22 phenyl-1H-pyrazoles' derivatives.

    PubMed

    de Oliveira, Aline Lima; Alves de Oliveira, Carlos Henrique; Mairink, Laura Maia; Pazini, Francine; Menegatti, Ricardo; Lião, Luciano Morais

    2011-08-01

    Complete assignment of (1)H and (13)C NMR chemical shifts and J((1)H/(1)H and (1)H/(19)F) coupling constants for 22 1-phenyl-1H-pyrazoles' derivates were performed using the concerted application of (1)H 1D and (1)H, (13)C 2D gs-HSQC and gs-HMBC experiments. All 1-phenyl-1H-pyrazoles' derivatives were synthesized as described by Finar and co-workers. The formylated 1-phenyl-1H-pyrazoles' derivatives were performed under Duff's conditions.

  8. Design and synthesis of some new 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-ureas as potent anticonvulsant and antidepressant agents.

    PubMed

    Mishra, Chandra Bhushan; Kumari, Shikha; Tiwari, Manisha

    2016-05-01

    A series of 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-urea derivatives (29-42) were designed, synthesized and evaluated for their anticonvulsant activity by using maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure tests. The acute neurotoxicity was checked by rotarod assay. Most of the test compounds were found effective in both seizure tests. Compound 30 (1-{4-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-urea) exhibited marked anticonvulsant activity in MES as well as scPTZ tests. The phase II anticonvulsant quantification study of compound 30 indicates the ED50 value of 28.5 mg/kg against MES induced seizures. In addition, this compound also showed considerable protection against pilocarpine induced status epilepticus in rats. Seizures induced by 3-mercaptopropionic acid model and thiosemicarbazide were significantly attenuated by compound 30, which suggested its broad spectrum of anticonvulsant activity. Interestingly, compound 30 displayed better antidepressant activity than standard drug fluoxetine. Moreover, compound 30 appeared as a non-toxic chemical entity in sub-acute toxicity studies.

  9. Synthesis and luminescence properties of 2-(benzylcarbamoyl)phenyl derivatives and their europium complexes.

    PubMed

    Guo, Dongcai; He, Wei; Liu, Bang; Gou, Lining; Li, Ruixia

    2013-01-01

    Six novel 2-(benzylcarbamoyl)phenyl derivatives were synthesized and characterized by (1) H-NMR, mass spectrometry, infrared spectra and elemental analysis. Their europium complexes were prepared and characterized by elemental analysis, EDTA titrimetric analysis, IR and UV spectra as well as molar conductivity measurements. The luminescence properties of these complexes were investigated and results show that 2-(benzylcarbamoyl)phenyl derivatives possess high selectivity and good coordination with the europium ion. Complex Eu-2-(benzylcarbamoyl)phenyl-2-phenylacetate showed green luminescence that was emitted by the ligand of 2-(benzylcarbamoyl)phenyl-2-phenylacetate, while other complexes showed the characteristic red luminescence of europium ion and also possessed high luminescence intensity.

  10. Phenyl Acetate Preparation from Phenol and Acetic Acid: Reassessment of a Common Textbook Misconception.

    ERIC Educational Resources Information Center

    Hocking, M. B.

    1980-01-01

    Reassesses a common textbook misconception that "...phenols cannot be esterified directly." Results of experiments are discussed and data tables provided of an effective method for the direct preparation of phenyl acetate. (CS)

  11. Tetratopic phenyl compounds, related metal-organic framework materials and post-assembly elaboration

    DOEpatents

    Farha, Omar K.; Hupp, Joseph T.

    2012-09-11

    Disclosed are tetratopic carboxylic acid phenyl for use in metal-organic framework compounds. These compounds are useful in catalysis, gas storage, sensing, biological imaging, drug delivery and gas adsorption separation.

  12. Tetratopic phenyl compounds, related metal-organic framework materials and post-assembly elaboration

    DOEpatents

    Farha, Omar K; Hupp, Joseph T

    2013-06-25

    Disclosed are tetratopic carboxylic acid phenyl for use in metal-organic framework compounds. These compounds are useful in catalysis, gas storage, sensing, biological imaging, drug delivery and gas adsorption separation.

  13. Inhibition of carbonyl reductase activity in pig heart by alkyl phenyl ketones.

    PubMed

    Imamura, Yorishige; Narumi, Rika; Shimada, Hideaki

    2007-02-01

    The inhibitory effects of alkyl phenyl ketones on carbonyl reductase activity were examined in pig heart. In this study, carbonyl reductase activity was estimated as the ability to reduce 4-benzoylpyridine to S(-)-alpha-phenyl-4-pyridylmethanol in the cytosolic fraction from pig heart (pig heart cytosol). The order of their inhibitory potencies was hexanophenone > valerophenone > heptanophenone > butyrophenone > propiophenone. The inhibitory potencies of acetophenone and nonanophenone were much lower. A significant relationship was observed between Vmax/Km values for the reduction of alkyl phenyl ketones and their inhibitory potencies for carbonyl reductase activity in pig heart cytosol. Furthermore, hexanophenone was a competitive inhibitor for the enzyme activity. These results indicate that several alkyl phenyl ketones including hexanophenone inhibit carbonyl reductase activity in pig heart cytosol, by acting as substrate inhibitors.

  14. Photoluminescence of 1-phenyl,3-methyl pyrazoloquinoline derivatives

    NASA Astrophysics Data System (ADS)

    Koścień, E.; Gondek, E.; Jarosz, B.; Danel, A.; Nizioł, J.; Kityk, A. V.

    2009-04-01

    Paper presents the absorption and photoluminescence of 7-TFM, 6-F, 6-CN, 6-TBu and 6-COOEt derivatives of 1-phenyl-3-methyl-1 H-Pyrazolo[3,4- b]quinoline (MPPQ). The measured spectra are compared with the results of the quantum chemical calculations performed by means of the semi-empirical methods (AM1 or PM3) that have been applied either to the equilibrium molecular conformations in vacuo ( T=0 K) or combined with the MD simulations ( T=300 K). The photoluminescent spectra of MPPQ dyes are highly solvatochromic. The emission bands broaden and shift to the red with the increasing of solvent polarity, indicating thus a substantial dipole moment of the excited states. According to the quantum chemical analysis the reason for the strong solvatochromism of MPPQ dyes is related with intramolecular charge transfer (ICT) state. Due to the large dipole moment in the twisted geometry the ICT state is believed to become the lowest excited state in a strongly polar environment. This would explain a considerable solvatochromic shift in the highly polar solvents observed for all MPPQ dyes in the experiment. Such hypothesis is supported by the semi-empirical quantum chemical evaluations.

  15. 1-Phenyl-4-(triphenyl­phosphanyl­idene)pyrrolidine-2,3,5-trione

    PubMed Central

    Fan, Da-He

    2008-01-01

    In the title compound, C28H20NO3P, the five-membered maleimide ring is almost planar. The inter­planar angles between the maleimide ring and the three P-bound phenyl rings are 70.6 (2), 60.4 (2) and 54.68 (18)°, while the dihedral angle between the maleimide ring and the N-bound phenyl group is 55.43 (19)°. PMID:21201913

  16. Chemical modification of cellulose acetate by N-(phenyl amino) maleimides: characterization and properties.

    PubMed

    Abdel-Naby, Abir S; Al-Ghamdi, Azza A

    2014-07-01

    Cellulose acetate (CA) was modified using N-(phenyl amino) maleimides (R-APhM) where, RH or 4-NO2. The structure of the modified polymer was characterized by (13)C-NMR. The chemical modification is based on the reaction between the acetyl group of the glucopyranose ring in cellulose acetate and the proton of the amino group in N-(phenyl amino) maleimide molecule. The thermal gravimetry (TGA) was used to investigate the thermal stability of the modified polymeric samples. The modified cellulose acetate by 4-nitro (phenyl amino) maleimide (CA/4-NO2APhM) exhibits the highest thermal stability as compared to the N-(phenyl amino) maleimide (CA/APhM) and the unmodified CA. The crystallinity and morphology of the modified polymeric samples were investigated using X-ray diffraction (XRD) and emission scanning electron microscope (ESEM), respectively. The presence of N-(phenyl amino) maleimide moieties in the cellulose acetate matrix improved its mechanical property. Also, the organic nature of (R-APhM) moieties inside CA matrix reduced its wettability.

  17. The role of carbon-carbon phenyl migration in the pyrolysis mechanism of beta-O-4 lignin model compounds: phenethyl phenyl ether and alpha-hydroxy phenethyl phenyl ether

    SciTech Connect

    Beste, Ariana; Buchanan III, A C

    2012-01-01

    We investigate phenyl shift and subsequent beta-scission reactions for PhCHXCHOPh [X = H, OH], which are part of the pyrolysis mechanism of phenethyl phenyl ether (PPE) and alpha-hydroxy PPE. PPE and its derivatives are model compounds for the most common linkage in lignin, the beta-O-4 linkage. We use density functional theory to locate transition states and equilibrium structures, and kinetic Monte Carlo in combination with transition state theory for kinetic simulations. Oxygen-carbon and carbon-carbon phenyl shift reactions proceed through cyclic intermediates with similar barriers. But, while subsequent beta-scission of the oxygen-carbon shift products proceeds with virtually no barrier, the activation energy for beta-scission of the carbon-carbon shift products exceeds 15 kcal/mol. We found that about 15 % of beta-radical conversion can be attributed to carbon-carbon shift for PPE and alpha-hydroxy PPE at 618 K. Whereas the oxygen-carbon shift reaction has been established as an integral part of the pyrolysis mechanism of PPE and its derivatives, participation of the carbon-carbon shift reaction has not been shown previously.

  18. Synthesis, spectroscopy, and quantum-chemical calculations on 1-substituted phenyl-3,5-diphenylformazans.

    PubMed

    Tezcan, Habibe; Tokay, Nesrin

    2010-01-01

    In this study 1-substituted phenyl-3,5-diphenylformazans were synthesized from benzaldehyde-N-phenylhydrazone and appropriate phenyldiazonium salts having CH(3), Br, and Cl at the o-, m-, and p-positions of 1-phenyl ring. Their structures were determined by infrared and ultraviolet-visible spectra. Bathochromic effect in accordance with the electron-donating effect of CH(3), Br, and Cl group and its magnitude were dependent upon type and position of substituent on the ring. The ground-state geometries and absorption wavelengths for 1-phenyl substituted formazans were studied with density functional theory and time-dependent density functional theory. The calculations were carried out by using PBE1PBE functional with 6-311G(2d,2p) basis set for lambda(max) of the UV-vis spectra for the studied formazans. A good agreement was obtained between the experimental and computed values.

  19. Bifunctional phenyl monophosphonic/sulfonic acid ion exchange resin and process for using the same

    DOEpatents

    Alexandratos, Spiro; Shelley, Christopher A.; Horwitz, E. Philip; Chiarizia, Renato

    2001-01-01

    A cross-linked water-insoluble ion exchange resin comprised of polymerized monomers having a phenyl ring is disclosed. A contemplated resin contains (i) polymerized phenyl ring-containing monomers having a phosphonic acid ligand linked to the phenyl ring, (ii) about 2 to about 5 millimoles per gram (mmol/g) of phosphorus as phosphonic acid ligands, and (iii) a sufficient amount of a sulfonic acid ligand such that the ratio of mmol/g of phosphonic acid to mmol/g sulfonic acid is up to 3:1. A process for removing polyvalent metal cations from aqueous solution, and a process for removing iron(III) cations from acidic copper(II) cation-containing solutions that utilize the contemplated resin or other resins are disclosed.

  20. Bifunctional phenyl monophosphonic/sulfonic acid ion exchange resin and process for using the same

    DOEpatents

    Alexandratos, Spiro; Shelley, Christopher A.; Horwitz, E. Philip; Chiarizia, Renato; Gula, Michael J.; Xue, Sui; Harvey, James T.

    2002-01-01

    A cross-linked water-insoluble ion exchange resin comprised of polymerized monomers having a phenyl ring is disclosed. A contemplated resin contains (i) polymerized phenyl ring-containing monomers having a phosphonic acid ligand linked to the phenyl ring, (ii) about 2 to about 5 millimoles per gram (mmol/g) of phosphorus as phosphonic acid ligands, and (iii) a sufficient amount of a sulfonic acid ligand such that the ratio of mmol/g of phosphonic acid to mmol/g sulfonic acid is up to 3:1. A process for removing polyvalent metal cations from aqueous solution, and a process for removing iron(III) cations from acidic copper(II) cation-containing solutions that utilize the contemplated resin or other resins are disclosed.

  1. 1-Benzhydryl-4-(4-chloro­phenyl­sulfonyl)piperazine

    PubMed Central

    Girisha, H. R.; Naveen, S.; Vinaya, K.; Sridhar, M. A.; Shashidhara Prasad, J.; Rangappa, K. S.

    2008-01-01

    The title compound, C23H23ClN2O2S, was synthesized by the nucleophilic substitution of 1-benzhydrylpiperazine with 4-chloro­phenyl­sulfonyl chloride. The piperazine ring is in a chair conformation. The geometry around the S atom is that of a distorted tetra­hedron. There is a large range of bond angles around the piperazine N atoms. The dihedral angle between the least-squares plane (p1) defined by the four coplanar C atoms of the piperazine ring and the benzene ring is 81.6 (1)°. The dihedral angles between p1 and the phenyl rings are 76.2 (1) and 72.9 (2)°. The two phenyl rings make a dihedral angle of 65.9 (1)°. Intramolecular C—H⋯O hydrogen bonds are present. PMID:21201390

  2. Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles

    PubMed Central

    Kumar, Yogesh; Bahadur, Vijay; Singh, Anil Kumar; Parmar, Virinder Singh; Van der Eycken, Erik V

    2014-01-01

    Summary A microwave-assisted synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles from a phenylazide, propargyloxybenzaldehyde and a 1,2-diaminobenzene is proposed. PMID:24991296

  3. Spectral behavior study of 3-(4-dimethylamino-phenyl)-1-{6-[3-(4-dimethylamino-phenyl)-acryloyl]-pyridin-2-yl}-propanone

    NASA Astrophysics Data System (ADS)

    Gaber, M.; El-Sayed, Y. S.; Diab, H.

    2011-04-01

    The photophysical properties such as singlet absorption, molar absorptivity, fluorescence spectra, fluorescence quantum yield ( ϕf) and transition dipole moment ( μ12) of 3-(4-dimethylamino-phenyl)-1-{6-[3-(4-dimethylamino-phenyl)-acryloyl]-pyridin-2-yl}-propanone (DMAPAPP) have been studied in different media. DMAPAPP exhibits a large red-shift in both absorption and emission spectra as the solvent polarity increases, indicating a large change in dipole moment of molecule upon excitation. The fluorescence quantum yield depends on the nature of the solvent. The absorption and emission spectra of DMAPAPP in dioxane-water mixture are also studied. The effect of different type of surfactants to determine their critical micellar concentration (CMC) and the microemulsion effect on the electronic absorption and emission spectra of DMAPAPP are recorded. The effect of acidity on the electronic absorption and emission spectra of DMAPAPP is studied to determine the pKa and pKa* values.

  4. Targeting kinases with anilinopyrimidines: discovery of N-phenyl-N’-[4-(pyrimidin-4-ylamino)phenyl]urea derivatives as selective inhibitors of class III receptor tyrosine kinase subfamily

    PubMed Central

    Gandin, Valentina; Ferrarese, Alessandro; Dalla Via, Martina; Marzano, Cristina; Chilin, Adriana; Marzaro, Giovanni

    2015-01-01

    Kinase inhibitors are attractive drugs/drug candidates for the treatment of cancer. The most recent literature has highlighted the importance of multi target kinase inhibitors, although a correct balance between specificity and non-specificity is required. In this view, the discovery of multi-tyrosine kinase inhibitors with subfamily selectivity is a challenging goal. Herein we present the synthesis and the preliminary kinase profiling of a set of novel 4-anilinopyrimidines. Among the synthesized compounds, the N-phenyl-N’-[4-(pyrimidin-4-ylamino)phenyl]urea derivatives selectively targeted some members of class III receptor tyrosine kinase family. Starting from the structure of hit compound 19 we synthesized a further compound with an improved affinity toward the class III receptor tyrosine kinase members and endowed with a promising antitumor activity both in vitro and in vivo in a murine solid tumor model. Molecular modeling simulations were used in order to rationalize the behavior of the title compounds. PMID:26568452

  5. Benzyl 5-phenyl-pyrazolo-[5,1-a]isoquino-line-1-carboxyl-ate.

    PubMed

    Lu, Yu-Kun; Yao, Xiao; Luo, Li-Wen; Lü, Ren-Qing; Liu, Yun-Qi

    2011-12-01

    In the title compound, C(25)H(18)N(2)O(2), the pyrazolo-[5,1-a]iso-quin-oline ring system is approximately planar [maximum deviation = 0.027 (2) Å] and is oriented at dihedral angles of 57.22 (6) and 71.36 (7)° with respect to the two phenyl rings. The phenyl rings are twisted to each other by a dihedral angle of 66.33 (8)°. A weak intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, weak C-H⋯π inter-actions are present.

  6. Dimeth-yl(2-oxo-2-phenyl-eth-yl)sulfanium bromide.

    PubMed

    Cao, Zhiling; Liu, Weiwei; Yin, Fujun

    2010-11-17

    Single crystals of the title compound, C(10)H(13)OS(+)·Br(-), were obtained from ethyl acetate/ethyl ether after reaction of acetophenone with hydro-bromic acid and dimethyl-sulfoxide. The carbonyl group is almost coplanar with the neighbouring phenyl ring [O-C-C-C = 178.9 (2)°]. The sulfanium group shows a trigonal-pyramidal geometry at the S atom. The crystal structure is stabil-ized by C-H⋯Br hydrogen-bonding inter-actions. Weak π-π inter-actions link adjacent phenyl rings [centroid-centroid distance = 3.946 (2) Å].

  7. 2-(1,3-Benzothia-zol-2-ylsulfan-yl)-1-phenyl-ethanone.

    PubMed

    Loghmani-Khouzani, Hossein; Hajiheidari, Dariush; Robinson, Ward T; Abdul Rahman, Noorsaadah; Kia, Reza

    2009-09-12

    In the mol-ecule of the title compound, C(15)H(11)NOS(2), the 1,3-benzothia-zole ring is oriented at a dihedral angle of 6.61 (6)° with respect to the phenyl ring. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules in a herring-bone arrangement along the b axis and π-π contacts between the thia-zole and phenyl rings [centroid-centroid distance = 3.851 (1) Å] may further stabilize the structure.

  8. Efficacy of a self-etching dentin primer composed of TEGMA and phenyl-P.

    PubMed

    Yoshimoto, Shinichiro; Itoh, Kazuo; Manabe, Atsufumi; Inoue, Mitsuko; Hisamitsu, Hisashi; Sasa, Ryuuji

    2004-01-01

    The purpose of the present study was to evaluate the efficacy of an experimental self-etching dentin primer composed of TEGMA and phenyl-P using primary and young permanent teeth. The efficacy of the self-etching dentin primer was evaluated by measuring the wall-to-wall polymerization contraction gap width and the shear bond strength to the flat dentin surface. The contraction gap formation was prevented completely in the specimens primed with the 35 vol% TEGMA and 20% phenyl-P for 30 sec.

  9. 2,3-Dicyano-4-[(4-methyl­phenyl­sulfon­yl)­oxy]phenyl 4-methyl­benzene­sulfonate

    PubMed Central

    Deng, Yanhua; Ma, Changqin; Zhang, Xiaomei

    2011-01-01

    In the title compound, C22H16N2O6S2, the dihedral angle formed by the mean planes of the two benzene rings of the 4-methyl­phenyl­sulfonate groups is 21.9 (1)° and these rings form dihedral angles of 48.26 (9) and 52.73 (9)° with the central benzene ring. PMID:21754170

  10. Synthesis of 3-Methyl-4-(4-methylbenzoyl)-1-phenyl-pyrazol-5-One: How to Avoid O-Acylation

    ERIC Educational Resources Information Center

    Kurteva, Vanya B.; Petrova, Maria A.

    2015-01-01

    In this laboratory experiment, students synthesize 3-methyl-4-(4-methylbenzoyl)-1-phenyl-pyrazol-5-one by selective C-acylation of 3-methyl-1-phenyl-1H-pyrazol-5-one. Calcium hydroxide is used to push the tautomeric equilibrium toward the enol form, to protect the hydroxyl functionality as a complex, to trap the liberated hydrogen chloride, and to…

  11. Methyl N-phenyl carbamate synthesis from aniline and methyl formate: carbon recycling to chemical products.

    PubMed

    Yalfani, Mohammad S; Lolli, Giulio; Müller, Thomas E; Wolf, Aurel; Mleczko, Leslaw

    2015-02-01

    Methyl N-phenyl carbamate was synthesized from aniline by using methyl formate as a green and efficient carbonylating agent. High yields were obtained at milder reaction conditions compared to the conventional CO/CH3 OH route. Studies on the reaction sequence led to suggest an alternative and more efficient route to the carbamate via formanilide as intermediate.

  12. 1,1,2,2-Tetra­phenyl-1λ5-diphosphane 1-sulfide

    PubMed Central

    Aluri, Bhaskar R.; Peitz, Stephan; Wöhl, Anina; Peulecke, Normen; Müller, Bernd H.; Spannenberg, Anke; Rosenthal, Uwe

    2009-01-01

    In the title mol­ecule, C24H20P2S, the P—P bond length is 2.2263 (5) Å. The two phenyl rings attached to the three- and five-coordinated P atoms, respectively, form dihedral angles of 56.22 (5) and 71.74 (5)°. PMID:21581997

  13. 4-Benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine

    PubMed Central

    Ouzidan, Y.; Obbade, S.; Capet, F.; Essassi, El Mokhtar; Ng, Seik Weng

    2010-01-01

    The imidazopyridine fused ring in the title compound, C19H14BrN3, is almost coplanar with the phenyl ring at the 2-position of the five-membered ring [dihedral angle = 2.4 (1). The crystal structure features short Br⋯Br contacts [3.562 (1) Å]. PMID:21580750

  14. Emission-wavelength-dependent decay of the fluorescent probe N-phenyl-1-naphthylamine.

    PubMed

    Matayoshi, E D; Kleinfeld, A M

    1981-06-22

    We have measured the fluorescence decay of N-phenyl-1-naphthylamine using the phase-modulation method, in several solvent systems and egg phosphatidylcholine vesicles. The decay is monoexponential in pure solvents (both polar and non-polar) of low viscosity. In polar viscous solvents or in non-polar solvents containing an added polar solute, the decay is heterogeneous and emission wavelength dependent. In such cases, dielectric relaxation and/or excited-rate complexing give rise to a shift of the emission spectrum on the nanosecond time scale. Emission-wavelength-dependent decay was also observed when N-phenyl-1-naphthylamine was bound to egg phosphatidylcholine vesicles. From these results as well as the position of the emission spectral maximum, we conclude that N-phenyl-1-naphthylamine probes the ester-carbonyl region of the phospholipid acyl chains, where it undergoes an excited-state reaction. This result contradicts the often made assumption that N-phenyl-1-naphthylamine probes the deeper hydrocarbon region of the bilayer.

  15. 40 CFR 721.10572 - Benzamide, N-[[4- [(cyclopropylamino)carbonyl] phenyl]sulfonyl]-2-methoxy-.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...- phenyl]sulfonyl]-2- methoxy- (PMN P-08-680; CAS No. 221667-31-8) is subject to reporting under this..., tight-fitting half-face respirator equipped with N100 (if oil aerosols absent), R100, or P100 filters... aerosols absent), R100, or P100 filters. (C) NIOSH-certified powered air-purifying respirator equipped...

  16. 40 CFR 721.10572 - Benzamide, N - [ [ 4- [(cyclopropylamino) carbonyl]phenyl] sulfonyl] -2 -methoxy-.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., N - phenyl]sulfonyl ] - 2 - methoxy - (PMN P-08-680; CAS No. 221667-31-8) is subject to reporting... filters. (B) NIOSH-certified air-purifying, tight-fitting full-face respirator equipped with N100 (if oil aerosols absent), R100, or P100 filters. (C) NIOSH-certified powered air-purifying respirator equipped...

  17. Reaction of Phenyl Radical with O2: Thermodynamic Properties, Important Reaction Paths and Kinetics

    SciTech Connect

    Bozzelli, J; Sebbar, N; Pitz, W; Bockhorn, H

    2001-04-12

    The Phenyl + O{sub 2} association results in a chemically activated phenyl-peroxy radical which can dissociate to phenoxy radical + O, undergo intramolecular addition of the peroxy radical to several unsaturated carbon sites or react back to phenyl + O{sub 2}. The intramolecular addition channels further react through several paths to ring opening (unsaturated + carbonyl moieties) as well as cyclopentadieny radical + CO{sub 2}. Enthalpy ({Delta}H{sub f(298)}{sup o}), Entropy (S{sub 298}), and heat capacities Cp(T) for species in the decomposition of the ring are evaluated using density functional and ab initio calculations and by comparisons to vinyl + O{sub 2} data of Mebel et al, and phenyl + O{sub 2} data of Hadad et al. Isodesmic reaction analysis is used to estimate enthalpy values of the intermediates and well depths of the adducts. High Pressure limit kinetic parameters are obtained from the calculation results using canonical Transition State Theory. Quantum RRK analysis is utilized to obtain k(E) and modified strong collision or master equation analysis is used for evaluation of pressure fall-off in this complex bimolecular, chemical activation, reaction system. Uncertainty in key barriers is discussed, resulting variations in important reaction product ratios are illustrated, and changes in these branching ratios are evaluated with a detailed reaction mechanism.

  18. [Isolation and fermentation conditions of strains producing 1-phenyl-2-amino-ethanol alcohol dehydrogenase].

    PubMed

    Wang, J; Wang, J; Yang, L; Wu, J; Sun, W

    2001-10-01

    A Arachnia sp. P163 producing alcohol dehydrogenase which is able to reduce aminoacetophenone to R-1-phenyl-2-aminoethanol was obtained from soil and cultures. The maximum activity of enzyme was produced by the LB medium containing 1% sodium citrate and peptone, 0.1% phenylaminoethanol as inducer at 30 degrees C for 48 hs.

  19. 40 CFR 721.2122 - Substituted phenyl azo substituted sulfo carbopolycycle.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2122 Substituted phenyl azo substituted sulfo carbopolycycle. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical...

  20. 40 CFR 721.2122 - Substituted phenyl azo substituted sulfo carbopolycycle.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2122 Substituted phenyl azo substituted sulfo carbopolycycle. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical...

  1. 40 CFR 721.2122 - Substituted phenyl azo substituted sulfo carbopolycycle.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2122 Substituted phenyl azo substituted sulfo carbopolycycle. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical...

  2. 1-(2,6-Diisopropyl-phen-oxy)-4-phenyl-phthalazine.

    PubMed

    Tong, Bihai; Mei, Qunying

    2012-08-01

    In the title mol-ecule, C(26)H(26)N(2)O, the phenyl and phen-oxy rings form dihedral angles of 54.66 (7) and 84.83 (6)°, respectively, with the phthalazine mean plane. The crystal packing exhibits weak C-H⋯π inter-actions.

  3. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Copper complex of (substituted... Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt... substances identified generically as copper complex of (substituted sulfonaphthyl azo substituted...

  4. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Copper complex of (substituted... Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt... substances identified generically as copper complex of (substituted sulfonaphthyl azo substituted...

  5. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Copper complex of (substituted... Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt... substances identified generically as copper complex of (substituted sulfonaphthyl azo substituted...

  6. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Copper complex of (substituted... Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt... substances identified generically as copper complex of (substituted sulfonaphthyl azo substituted...

  7. A Quick and Simple Conversion of Carboxylic Acids into Their Anilides of Heating with Phenyl Isothiocyanate.

    ERIC Educational Resources Information Center

    Ram, Ram N.; And Others

    1983-01-01

    Converting carboxylic acids into their anilides, which usually involves preparation of acid chloride or mixed anhydride followed by treatment with aniline, is tedious and/or time-consuming. A quick and easier procedure, using phenyl isothiocyanate, is provided. Reactions involved and a summary table of results are included. (JN)

  8. Bioactive 1 4-Dihydroxy-5-phenyl-2-pyridinone alkaloids from Septoria pistaciarum

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids (1-4) were isolated from an EtOAc extract of a culture medium of Septoria pistaciarum. The structures of these compounds were determined by spectroscopic methods, and the absolute configuration of the major compound 1 by X-ray crystallographic a...

  9. Microwave-assisted synthesis, structural elucidation and biological assessment of 2-(2-acetamidophenyl)-2-oxo-N phenyl acetamide and N-(2-(2-oxo-2(phenylamino)acetyl)phenyl)propionamide derivatives

    NASA Astrophysics Data System (ADS)

    Ghazzali, Mohamed; El-Faham, Ayman; Abdel-Megeed, Ahmed; Al-Farhan, Khalid

    2012-04-01

    A facile solid-state synthesis of 2-(2-acetamidophenyl)-2-oxo-N phenyl acetamide and N-(2-(2-oxo-2(phenylamino)acetyl)phenyl)propionamide six derivatives has been achieved by microwave promoted condensation of N-acylisatin or N-propionylisatin with various aniline derivatives. The six products were characterized by IR and NMR (H1 and C13). Only two of them, The N-[2-(4-Bromo-phenylaminooxalyl)-phenyl]-propionamide and 2-(2-Acetylamino-phenyl)-2-oxo-N-p-tolyl-acetamide molecular structures were verified by X-ray single-crystal diffraction. The Br⋯Br intermolecular interaction in the crystal structure of N-[2-(4-Bromo-phenylaminooxalyl)-phenyl]-propionamide was evaluated by DFT/B3LYP calculation. The antimicrobial activity was evaluated against eight bacterial strains and two fungal species. The N-[2-(4-Bromo-phenylaminooxalyl)-phenyl]-propionamide and 2-(2-Acetylamino-phenyl)-2-oxo-N-p-tolyl-acetamide exhibit selective high inhibitory effects against Aspergillus niger and Staphylococcus aureus, respectively.

  10. Crossed beam reactions of the phenyl (C6H5; X(2)A1) and phenyl-d5 radical (C6D5; X(2)A1) with 1,2-butadiene (H2CCCHCH3; X(1)A').

    PubMed

    Yang, Tao; Parker, Dorian S N; Dangi, Beni B; Kaiser, Ralf I; Kislov, Vadim V; Mebel, Alexander M

    2014-06-26

    We explored the reactions on the phenyl (C6H5; X(2)A1) and phenyl-d5 (C6D5; X(2)A1) radical with 1,2-butadiene (C4H6; X(1)A') at a collision energy of about 52 ± 3 kJ mol(-1) in a crossed molecular beam apparatus. The reaction of phenyl with 1,2-butadiene is initiated by adding the phenyl radical with its radical center to the π electron density at the C1/C3 carbon atom of 1,2-butadiene. Later, the initial collision complexes isomerize via phenyl group migration from the C1/C3 carbon atoms to the C2 carbon atom of the allene moiety of 1,2-butadiene. The resulting intermediate undergoes unimolecular decomposition through hydrogen atom emission from the methyl group of the 1,2-butadiene moiety via a rather loose exit transition state leading to 2-phenyl-1,3-butadiene in an overall exoergic reaction (ΔRG = -72 ± 10 kJ mol(-1)). This finding reveals the strong collision-energy dependence of this system when the data are compared with those of the phenyl radical with 1,2-butadiene previously recorded at collision energies up to 160 kJ mol(-1), with the previous study exhibiting the thermodynamically less stable 1-phenyl-3-methylallene (ΔRG = -33 ± 10 kJ mol(-1)) and 1-phenyl-2-butyne (ΔRG = -24 ± 10 kJ mol(-1)) to be the dominant products.

  11. Phenyl amide linker improves the pharmacokinetics and pharmacodynamics of N-terminally mono-PEGylated human growth hormone.

    PubMed

    Wu, Ling; Ji, Shaoyang; Shen, Lijuan; Hu, Tao

    2014-09-02

    Human growth hormone (hGH) suffers from a short plasma half-life of ∼15 min, necessitating frequent injections to maintain its physiological effect. PEGylation, conjugation of polyethylene glycol (PEG), is an effective strategy to prolong the plasma half-life of hGH. However, PEGylation can significantly decrease the bioactivity of hGH. Thus, a new PEGylation approach is desired to improve the pharmacokinetics (PK) and pharmacodynamics (PD) of the PEGylated hGH. In the present study, two N-terminally mono-PEGylated hGHs were prepared using aldehyde chemistry. Phenyl amide and ethyl moieties were used as the linkers between PEG and hGH, respectively. The hydrodynamic volume, proteolytic sensitivity, and immunogenicity of the PEGylated hGH with phenyl amide linker (hGH-phenyl-PEG) were lower than those of the one with propyl linker (hGH-prop-PEG). In addition, hGH-phenyl-PEG showed a higher in vitro bioactivity and better PK and PD than hGH-prop-PEG. The better PK of hGH-phenyl-PEG was mainly due to its lower proteolytic sensitivity and low immunogenicity. The better PD of hGH-phenyl-PEG was mainly due to its higher in vitro bioactivity. Thus, the phenyl amide linker can improve the overall pharmacological profiles of the PEGylated hGH. Our study is expected to advance the development of long-acting protein biotherapeutics with high therapeutic efficacy.

  12. Methyl 2-[(3RS,4RS)-3-phenyl-4-(phenyl­sulfon­yl)isoxazolidin-2-yl]acetate

    PubMed Central

    Gültekin, Zeynep; Civan, Mehmet; Frey, Wolfgang; Hökelek, Tuncer

    2014-01-01

    In the title compound, C18H19NO5S, the five-membered isoxazolidine ring is in a half-chair conformation, and the phenyl rings are oriented at a dihedral angle of 66.53 (3)°. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional supra­molecular structure. A weak C—H⋯π inter­action is also observed between adjacent mol­ecules. PMID:24940296

  13. Fluorescent complexes of DNA with DAPI 4′,6-diamidine-2-phenyl indole.2HCl or DCI 4′,6-dicarboxyamide-2-phenyl indole

    PubMed Central

    Kapuściński, Jan; Skoczylas, Bogna

    1978-01-01

    4′,6-Dioarboxyamide-2-phenyl indole (DCI), a non-ionic structural analogue of 4′,6-diamidine-2-phenyl indole·2HCl (DAPI), was synthesized in order to verify the hypothesis of intercalation of both dyes into the DNA double helix. The influence of pH, viscosity, and different concentrations of SDS (sodium dodecylsulphate) or NaCl on the optical and fluorescent properties and the changes in thermal transition of both dye complexes with DNA confirm the affinity of the dyes to the double helix as well as their stabilizing influence on the secondary DNA structure. The results of binding studies, carried out by fluorescent methods have shown that the dyes are strongly bound to DNA, though the number of binding sites is small. According to the experimental data, the fluorescent properties of DAPI and DCI complexes with DNA are connected with the intercalating binding mechanism of these dyes. On the other hand, the eventual ionic or hydrogen bonds of dyes outside the DNA helix do not change noticeably their fluorescent properties. PMID:31603

  14. Removal of phenyl-urea herbicides in ultrapure water by ultrafiltration and nanofiltration processes.

    PubMed

    Benitez, F Javier; Acero, Juan L; Real, Francisco J; Garcia, Carolina

    2009-02-01

    Membrane filtration of four phenyl-urea herbicides (linuron, diuron, chlortoluron, and isoproturon) dissolved in ultrapure water was studied in a laboratory cross-flow device in batch concentration mode (with recycling of the retentate stream). Three UF (MWCO of 20 000, 5000 and 2000Da) and three NF (MWCO of 150-300Da) membranes were used. The influence of the main operating conditions (transmembrane pressure, tangential velocity, temperature, pH, and MWCO of the membranes) on the steady-state permeate fluxes and the retention factors of the phenyl-ureas was evaluated. The herbicide mass adsorbed onto the membranes was also determined, and the contribution of the fouling resistance to the total resistance to permeate flux was much lower than the inherent resistance of the clean membranes.

  15. Discovery of phenyl acetamides as potent and selective GPR119 agonists.

    PubMed

    Zhu, Cheng; Wang, Liping; Zhu, Yuping; Guo, Zack Zhiqiang; Liu, Ping; Hu, Zhiyong; Szewczyk, Jason W; Kang, Ling; Chicchi, Gary; Ehrhardt, Anka; Woods, Andrea; Seo, Toru; Woods, Morgan; van Heek, Margaret; Dingley, Karen H; Pang, Jianmei; Salituro, Gino M; Powell, Joyce; Terebetski, Jenna L; Hornak, Viktor; Campeau, Louis-Charles; Orr, Robert K; Ujjainwalla, Feroze; Miller, Michael; Stamford, Andrew; Wood, Harold B; Kowalski, Timothy; Nargund, Ravi P; Edmondson, Scott D

    2017-03-01

    The paper describes the SAR/SPR studies that led to the discovery of phenoxy cyclopropyl phenyl acetamide derivatives as potent and selective GPR119 agonists. Based on a cis cyclopropane scaffold discovered previously, phenyl acetamides such as compound 17 were found to have excellent GPR119 potency and improved physicochemical properties. Pharmacokinetic data of compound 17 in rat, dog and rhesus will be described. Compound 17 was suitable for QD dosing based on its predicted human half-life, and its projected human dose was much lower than that of the recently reported structurally-related benzyloxy compound 2. Compound 17 was selected as a tool compound candidate for NHP (Non-Human Primate) efficacy studies.

  16. Crystal structure of 1-bromo-2-(phenyl­selen­yl)benzene

    PubMed Central

    Charette, Bronte J.; Ritch, Jamie S.

    2015-01-01

    In the title compound, C12H9BrSe, the Se atom exhibits a bent geometry, with a C—Se—C bond angle of 99.19 (6)°. The ortho Se and Br atoms are slightly displaced from opposite faces of the mean plane of the benzene ring [by 0.129 (2) and 0.052 (2) Å, respectively]. The planes of the benzene and phenyl rings form a dihedral angle of 72.69 (5)°. In the crystal, π-stacking inter­actions between inversion-related phenyl rings are observed, with a centroid–centroid distance of 3.630 (1) Å. PMID:25844201

  17. Crystal structure of 1-bromo-2-(phenyl-selen-yl)benzene.

    PubMed

    Charette, Bronte J; Ritch, Jamie S

    2015-03-01

    In the title compound, C12H9BrSe, the Se atom exhibits a bent geometry, with a C-Se-C bond angle of 99.19 (6)°. The ortho Se and Br atoms are slightly displaced from opposite faces of the mean plane of the benzene ring [by 0.129 (2) and 0.052 (2) Å, respectively]. The planes of the benzene and phenyl rings form a dihedral angle of 72.69 (5)°. In the crystal, π-stacking inter-actions between inversion-related phenyl rings are observed, with a centroid-centroid distance of 3.630 (1) Å.

  18. Dimeth­yl(2-oxo-2-phenyl­eth­yl)sulfanium bromide

    PubMed Central

    Cao, Zhiling; Liu, Weiwei; Yin, Fujun

    2010-01-01

    Single crystals of the title compound, C10H13OS+·Br−, were obtained from ethyl acetate/ethyl ether after reaction of acetophenone with hydro­bromic acid and dimethyl­sulfoxide. The carbonyl group is almost coplanar with the neighbouring phenyl ring [O—C—C—C = 178.9 (2)°]. The sulfanium group shows a trigonal–pyramidal geometry at the S atom. The crystal structure is stabil­ized by C—H⋯Br hydrogen-bonding inter­actions. Weak π–π inter­actions link adjacent phenyl rings [centroid–centroid distance = 3.946 (2) Å]. PMID:21589491

  19. (S)-1-Ferrocenyl-3-hy­droxy-3-phenyl­propan-1-one

    PubMed Central

    Wang, Ping-An

    2011-01-01

    In the title compound, [Fe(C5H5)(C14H13O2)], the dihedral angle between the phenyl ring and the unsubstituted cyclo­petadienyl ring is 85.0 (2)°while that between the phenyl ring and the substituted cyclo­petadienyl ring is 83.6 (2)°. The dihedral angle between the two cyclo­penta-1,3-diene rings of the ferrocene unit is 2.2 (2)°. The mol­ecules are stabilized by inter­molecular O—H⋯O hydrogen-bonding inter­action within the crystal lattice. PMID:21522855

  20. Liquid Crystals Derived from 2-phenyl-isoindoles: Synthesis and Characterization

    NASA Technical Reports Server (NTRS)

    Jow, Kenny G.; Dingemans, Theo J.; Bushnell, Dennis M. (Technical Monitor)

    2001-01-01

    2-Phenyl-isoindole was investigated as the rigid core unit in a series of asymmetric mesogenic molecules. When the 2-phenyl-isoindole core was terminated with a hexyl tail, no mesophase formation could be observed. When 4-n-(tridecafluorohexyl) was used, however, we observed both monotropic and enantiotropic phase behavior. We found that most functionalities at the anhydride 5-position results in the formation of smectic A (SmA) phases in the temperature range of 70-180 C. Functionalities at the anhydride 4-position suppress mesophase formation. Large substituents (-Br, -NO2) and symmetric substitution patterns (5,6-dichloro, 4,7-dichloro and 4,5,6,7-tetrachloro) on the anhydride moiety increase the melting point and destabilize the mesophase. Temperature dependent X-ray diffraction experiments suggest an interdigitated SmA packing for this family of compounds.

  1. The structure and bonding properties of chosen phenyl ladder-like silsesquioxane clusters

    NASA Astrophysics Data System (ADS)

    Koleżyński, Andrzej; Jastrzębski, Witold; Szczypka, Wojciech; Kowalewska, Anna; Nowacka, Maria; Sitarz, Maciej

    2013-07-01

    The poly(phenyl silsesquioxanes) were synthesized at 30-36 °C via direct co-hydrolysis and condensation using sequential one batch, two-step reactions in the presence of potassium carbonate as the base catalyst and in the mixture THF/H2O. The structure and properties of the obtained materials were analyzed using NMR, TGA, SEC, XRD and FTIR methods. For chosen ladder-like phenyl silsesquioxane model clusters the DFT calculations by means of Gaussian09 program using B98 (DFT) method and a set 6-31G (d) of basis functions were carried out and respective infrared spectra were constructed and compared with the experimentally obtained ones. The results of topological analysis of total electron density obtained in SCF calculations (Quantum Theory of Atoms in Molecules approach) and structural analysis based on Bond Valence Method were used in detailed analysis of bonding properties in these clusters.

  2. Synthesis and biological relationships of 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents.

    PubMed

    Lai, Ya-Yun; Huang, Li-Jiau; Lee, Kuo-Hsiung; Xiao, Zhiyan; Bastow, Kenneth F; Yamori, Takao; Kuo, Sheng-Chu

    2005-01-03

    As part of a continuing search for potential anticancer drug candidates in the 2-phenyl-4-quinolone series, 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized and evaluated. Preliminary screening showed that carboxylic acid analogs containing a m-fluoro substituted 2-phenyl group displayed the highest in vitro anticancer activity. Activity decreased significantly if a chlorine or methoxy group replaced the fluorine atom. 3'-Fluoro-6-methoxy-2-phenyl-4-quinolone-3-carboxylic acid (68) had the highest in vitro cytotoxic activity among all tested carboxylic acid derivatives and their salts. The mechanism of action may be similar, but not identical, to that of tubulin binding drugs, such as navelbine and taxol. Compound 68 merits further investigation as a novel hydrophilic antimitotic agent.

  3. 2-Phenyl-2,3-dihydro-phenanthro[9,10-b][1,4]dioxine.

    PubMed

    Fun, Hoong-Kun; Quah, Ching Kheng; Wu, Dongdong; Zhang, Yan

    2011-02-05

    In the title compound, C(22)H(16)O(2), the phenanthrene ring system is essentially planar [maximum deviation = 0.058 (1) Å] and is inclined at an angle of 58.39 (6)° to the phenyl ring. The 1,4-dioxane ring is in a chair conformation. In the crystal, mol-ecules are stacked along the b axis, but no significant hydrogen bonds are observed.

  4. Phenyl Esters Are Potent Inhibitors of Caseinolytic Protease P and Reveal a Stereogenic Switch for Deoligomerization.

    PubMed

    Hackl, Mathias W; Lakemeyer, Markus; Dahmen, Maria; Glaser, Manuel; Pahl, Axel; Lorenz-Baath, Katrin; Menzel, Thomas; Sievers, Sonja; Böttcher, Thomas; Antes, Iris; Waldmann, Herbert; Sieber, Stephan A

    2015-07-08

    Caseinolytic protease P (ClpP) represents a central bacterial degradation machinery that is involved in cell homeostasis and pathogenicity. The functional role of ClpP has been studied by genetic knockouts and through the use of beta-lactones, which remain the only specific inhibitors of ClpP discovered to date. Beta-lactones have served as chemical tools to manipulate ClpP in several organisms; however, their potency, selectivity and stability is limited. Despite detailed structural insights into the composition and conformational flexibility of the ClpP active site, no rational efforts to design specific non-beta-lactone inhibitors have been reported to date. In this work, an unbiased screen of more than 137 000 compounds was used to identify five phenyl ester compounds as highly potent ClpP inhibitors that were selective for bacterial, but not human ClpP. The potency of phenyl esters largely exceeded that of beta-lactones in ClpP peptidase and protease inhibition assays and displayed unique target selectivity in living S. aureus cells. Analytical studies revealed that while phenyl esters are cleaved like native peptide substrates, they remain covalently trapped as acyl-enzyme intermediates in the active site. The synthesis of 36 derivatives and subsequent structure-activity relationship (SAR) studies provided insights into conserved structural elements that are important for inhibition potency and acylation reactivity. Moreover, the stereochemistry of a methyl-substituent at the alpha position to the ester, resembling amino acid side chains in peptide substrates, impacted ClpP complex stability, causing either dissociation into heptamers or retention of the tetradecameric state. Mechanistic insights into this intriguing stereo switch and the phenyl ester binding mode were obtained by molecular docking experiments.

  5. 3-Methyl­sulfanyl-5-phenyl-1,2,4-triazine

    PubMed Central

    Hamri, Salha; Hafid, Abderrafia; Khouili, Mostafa; El Ammari, Lahcen; Ketatni, El Mostafa

    2014-01-01

    In the mol­ecule of the title compound, C10H9N3S, the dihedral angle between the triazine and phenyl rings is 11.77 (7)°. In the crystal, mol­ecules are linked by π–π stacking inter­actions [centroid–centroid distances = 3.7359 (3) and 3.7944 (4) Å], forming layers parallel to the bc plane. PMID:24940289

  6. 3-Hydroxy-2-phenyl-4(1H)-quinolinones as promising biologically active compounds.

    PubMed

    Hradil, P; Hlavác, J; Soural, M; Hajdúch, M; Kolár, M; Vecerová, R

    2009-06-01

    2-Phenyl-3-hydroxy-4(1H)-quinolinones can be considered as aza-analogues of flavones, compounds which are known for the wide-range of their biological activity. These quinolinones were studied as inhibitors of topoisomerase, gyrase and IMPDH. They were tested for anticancer activity in-vitro and were also shown to possess immunosuppressive properties. This review is the first summarizing the synthesis and activity of the mentioned quinolinones.

  7. 2,2-Bis[(2-halo-4-aminophenoxy)phenyl]-hexafluoropropane

    NASA Technical Reports Server (NTRS)

    Jones, Robert J. (Inventor); Chang, Glenn E. C. (Inventor)

    1985-01-01

    There are provided the aromatic diamines 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane, where the attached ortho halogen is preferably chlorine, and 4,4'-bis(4-aminophenoxy)biphenyl, as novel monomers for polyimide polymerizations. The former, when reacted with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, provides a polyimide having exceptional high-temperature performance. The latter diamine is a low-cost monomer for polyimide production.

  8. 4-Hy-droxy-1-methyl-3-phenyl-quinolin-2(1H)-one.

    PubMed

    Kafka, Stanislav; Pevec, Andrej; Proisl, Karel; Kimmel, Roman; Košmrlj, Janez

    2013-02-01

    In the title compound, C(16)H(13)NO(2), the quinoline system is approximately planar with a maximum deviation from the least-squares plane of 0.059 (1) Å for the N atom. The phenyl ring is rotated by 62.16 (4)° with respect to the plane of the quinoline system. In the crystal, O-H⋯O hydrogen bonds link mol-ecules into infinite chains running along the b-axis direction.

  9. Substituted piperazines as nootropic agents: 2- or 3-phenyl derivatives structurally related to the cognition-enhancer DM235.

    PubMed

    Guandalini, Luca; Martino, Maria Vittoria; Di Cesare Mannelli, Lorenzo; Bartolucci, Gianluca; Melani, Fabrizio; Malik, Ruchi; Dei, Silvia; Floriddia, Elisa; Manetti, Dina; Orlandi, Francesca; Teodori, Elisabetta; Ghelardini, Carla; Romanelli, Maria Novella

    2015-04-15

    A series of 2-phenyl- or 3-phenyl piperazines, structurally related to DM235 and DM232, two potent nootropic agents, have been prepared and tested in the mouse passive-avoidance test, to assess their ability to revert scopolamine-induced amnesia. Although the newly synthesized molecules were less potent than the parent compounds, some useful information has been obtained from structure-activity relationships. A small but significant enantioselectivity has been found for the most potent compound 5a.

  10. Reaction of 1-chloro-1-methylcyclohexane with phenyl- and benzyl-trimethylsilanes in the presence of aluminum chloride

    SciTech Connect

    Bolestova, G.I.; Parnes, Z.N.; Vol'pin, M.E.

    1988-10-20

    In the reaction of 1-chloro-1-methylcyclohexane with phenyltrimethylsilane and benzyltrimethylsilane in the presence of aluminum chloride the chlorine atom is substituted by a phenyl or benzyl group with the formation of 1-methyl-1-phenyl- and 1-methyl-1-benzylcyclohexane, respectively. In the case of benzyltrimethylsilane the products from alkylation of the benzene ring of the benzyltrimethylsilane by the 1-methylcyclohexyl carbocation in the Friedel-Crafts reaction are formed in addition to 1-methyl-1-benzylcyclohexane.

  11. 4-(Diphenyl­amino)­benzaldehyde 4-phenyl­thio­semicarbazone

    PubMed Central

    Mendoza-Meroño, Rafael; Menéndez-Taboada, Laura; García-Granda, Santiago

    2012-01-01

    The title mol­ecule, C26H22N4S, is composed of three main parts, viz. a triphenyl­amine group is connected to a phenyl ring by a thio­semicarbazone moiety. The C= N double bond has an E conformation. The crystal packing is dominated by strong hydrogen bonds through the thio­semicarbazone moiety, with pairs of N—H⋯S hydrogen bonds linking the mol­ecules to form inversion dimers with an R 2 2(8) ring motif. An intra­molecular N—H⋯N hydrogen bond is also present, generating an S(5) ring motif. Although the structure contains four phenyl rings, π–π stacking inter­actions are not formed between them, probably due to the conformation adopted by the triphenyl­amine group. However, a weak π–π stacking inter­action is observed between the phenyl ring and the delocalized thio­semicarbazone moiety. PMID:22904859

  12. Structure-Dependent Photophysics of First-Generation; Phenyl-Cored Thiophene Dendrimers

    SciTech Connect

    Mitchell, W. J.; Ferguson, A. J.; Kose, M. E.; Rupert, B. L.; Ginley, D. S.; Rumbles, G.; Shaheen, S. E.; Kopidakis, N.

    2009-01-01

    We have prepared two series of first-generation thiophene-bridge dendrimers, with either three (3G1) or four (4G1) arms attached to a phenyl core, to elucidate their structure-property relationships. Optical properties were investigated with a combination of steady-state and time-resolved spectroscopic techniques. Steady-state spectroscopic data for the 3-arm dendrimers suggests that the exciton is delocalized over the {alpha}-conjugated thiophene segment and the phenyl core, but that the meta-linking of the dendrons prevents their electronic communication. In contrast, conjugation through the core to dendrons in the ortho and para positions is permitted in the 4-arm dendrimers, although the data suggest that the conjugation length does not extend over the full length of the {alpha}-conjugated sections of two coupled dendrons. This observation is due to steric interactions between neighboring arms, which forces the arms to twist and bend out of the plane of the phenyl core, and is particularly prevalent in disrupting the conjugation through the ortho positions. As expected, our results show that an increase in the bridge length results in an increase in the conjugation length for both dendrimers, and a subsequent red-shift of the absorption and emission. In addition, an increase in the dendron length results in an increase in the photoluminescence quantum yield and lifetime, suggesting that the ground and excited-state geometries are very similar and that the electronic transition is coupled to fewer vibrational modes.

  13. Optimization of lipase-catalyzed enantioselective production of 1-phenyl 1-propanol using response surface methodology.

    PubMed

    Soyer, Asli; Bayraktar, Emine; Mehmetoglu, Ulku

    2010-01-01

    Optically active 1-phenyl 1-propanol is used as a chiral building block and synthetic intermediate in the pharmaceutical industries. In this study, the enantioselective production of 1-phenyl 1-propanol was investigated systematically using response surface methodology (RSM). Before RSM was applied, the effects of the enzyme source, the type of acyl donor, and the type of solvent on the kinetic resolution of 1-phenyl 1-propanol were studied. The best results were obtained with Candida antartica lipase (commercially available as Novozym 435), vinyl laurate as the acyl donor, and isooctane as the solvent. In the RSM, substrate concentration, molar ratio of acyl donor to the substrate, amount of enzyme, temperature, and stirring rate were chosen as independent variables. The predicted optimum conditions for a higher enantiomeric excess (ee) were as follows: substrate concentration, 233 mM; molar ratio of acyl donor to substrate, 1.5; enzyme amount, 116 mg; temperature, 47 °C; and stirring rate, 161 rpm. A verification experiment conducted at these optimized conditions for maximum ee yielded 91% for 3 hr, which is higher than the predicted value of 83%. The effect of microwave on the ee was also investigated and ee reached 87% at only 5 min.

  14. Computational study of bond dissociation enthalpies for lignin model compounds. Substituent effects in phenethyl phenyl ethers.

    PubMed

    Beste, Ariana; Buchanan, A C

    2009-04-03

    Lignin is an abundant natural resource that is a potential source of valuable chemicals. Improved understanding of the pyrolysis of lignin occurs through the study of model compounds for which phenethyl phenyl ether (PhCH(2)CH(2)OPh, PPE) is the simplest example representing the dominant beta-O-4 ether linkage. The initial step in the thermal decomposition of PPE is the homolytic cleavage of the oxygen-carbon bond. The rate of this key step will depend on the bond dissociation enthalpy, which in turn will depend on the nature and location of relevant substituents. We used modern density functional methods to calculate the oxygen-carbon bond dissociation enthalpies for PPE and several oxygen-substituted derivatives. Since carbon-carbon bond cleavage in PPE could be a competitive initial reaction under high-temperature pyrolysis conditions, we also calculated substituent effects on these bond dissociation enthalpies. We found that the oxygen-carbon bond dissociation enthalpy is substantially lowered by oxygen substituents situated at the phenyl ring adjacent to the ether oxygen. On the other hand, the carbon-carbon bond dissociation enthalpy shows little variation with different substitution patterns on either phenyl ring.

  15. 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

  16. Investigation of platelet aggregation inhibitory activity by phenyl amides and esters of piperidinecarboxylic acids.

    PubMed

    de Candia, Modesto; Summo, Luciana; Carrieri, Antonio; Altomare, Cosimo; Nardecchia, Adele; Cellamare, Saverio; Carotti, Angelo

    2003-04-03

    A series of anilides and phenyl esters of piperidine-3-carboxylic acid (nipecotic acid) were synthesized and tested for the ability to inhibit aggregation of human platelet rich-plasma triggered by adenosine 5'-diphosphate (ADP) and adrenaline. As a rule, amides were about two times more active than the corresponding esters, and derivatives bearing substituents at the para position of the phenyl ring were significantly more active than the meta-substituted ones. Among the tested compounds, 4-hexyloxyanilide of nipecotic acid (18a) was found to be the most active one, its IC(50) value being close to that of the most active bis-3-carbamoylpiperidines reported in literature (ca. 40 micro M) and aspirin (ca. 60 microM) in ADP- and adrenaline-induced aggregation, respectively. Compared with the isomeric 4-hexyloxyanilides of piperidine-2-carboxylic (pipecolinic) and piperidine-4-carboxylic (isonipecotic) acids, compound 18a showed higher activity, and a Hansch-type quantitative structure-activity relationship (QSAR) study highlighted lipophilicity and increase in electron density of the phenyl ring as the properties which mainly increase the antiplatelet activity (r(2)=0.74, q(2)=0.64). The interaction of nipecotoyl anilides with phosphatidylinositol, a major component of the inner layer of the platelet membranes, was investigated by means of flexible docking calculation methods to give an account of a key event underlying their biological action.

  17. Controlled tautomeric switching in azonaphthols tuned by substituents on the phenyl ring.

    PubMed

    Antonov, Liudmil; Deneva, Vera; Simeonov, Svilen; Kurteva, Vanya; Crochet, Aurelien; Fromm, Katharina M; Shivachev, Boris; Nikolova, Rositsa; Savarese, Marika; Adamo, Carlo

    2015-02-23

    A series of new tautomeric azonaphthols are synthesized and the possibilities for molecular switching are investigated using molecular spectroscopy, X-ray analysis and density functional theory quantum chemical calculations. Two opposite effects that influence switching are studied: attaching a piperidine sidearm, and adding substituents to the phenyl ring. On the one hand, the attached piperidine moiety stabilizes the enol form leading to a controlled shift of the equilibrium upon protonation. On the other hand, the relative stability of the azonaphthol tautomers strongly depends on the effects of the substituents on the phenyl ring: electron donors tend to stabilize the enol tautomer, whereas electron acceptors lead to stabilization of the keto form. However, these effects do not shift fully the equilibrium towards either of the tautomers. Nevertheless, the effect of the substituents can be an additional tool to affect the switching between "on" and "off" states. Electron-withdrawing substituents stabilize the keto form and impede switching to the off state, whereas electron donors stabilize the enol form. The effect of the piperidine unit is dominant overall, and with strongly electron-withdrawing substituents at the phenyl ring, the enol form exists as a zwitterion.

  18. Synthesis and antiproliferative activity of 3-amino-N-phenyl-1H-indazole-1-carboxamides.

    PubMed

    Raffa, Demetrio; Maggio, Benedetta; Cascioferro, Stella; Raimondi, Maria Valeria; Schillaci, Domenico; Gallo, Giorgio; Daidone, Giuseppe; Plescia, Salvatore; Meneghetti, Fiorella; Bombieri, Gabriella; Di Cristina, Antonietta; Pipitone, Rosaria M; Grimaudo, Stefania; Tolomeo, Manlio

    2009-01-01

    A series of new 3-amino-N-phenyl-1H-indazole-1-carboxamides 10 have been prepared from commercially available phenyl isocyanate precursors 8 and 3-aminoindazole 9. Some of the synthesized compounds were evaluated for their in vitro antineoplastic activity against 60 human cell lines derived from seven clinically isolated cancer types (lung, colon, melanoma, renal, ovarian, brain, and leukemia) according to the NCI standard protocol. The test results indicated that 3-amino-1H-indazole-1-carboxamides 10 were endowed with an interesting antiproliferative activity. The most active compounds of this series, 10d,e, were able to inhibit cell growth of many neoplastic cell lines at concentrations lower than 1 microM (0.0153 microM in SR leukemia) causing a block in G0-G1 phase of cell cycle. Analysis of pRb expression showed that these two compounds increased the ratio between underphosphorylated pRb and total pRb. The X-ray structure of 10w, confirmed the 3-amino-N-phenyl-1H-indazole-1-carboxamide structure of compounds 10.

  19. 4,4-Dimethyl-2-[3-nitro-2-phenyl-1-(phenyl­sulfan­yl)prop­yl]-4,5-dihydro-1,3-oxazole

    PubMed Central

    Caracelli, Ignez; Zukerman-Schpector, Julio; Villar, José A. F. P.; Oliveira, Alfredo R. M.; Tiekink, Edward R. T.

    2012-01-01

    In the title compound, C20H22N2O3S, the oxazoline ring is planar (r.m.s. deviation = 0.045 Å) and forms dihedral angles of 47.24 (8) and 10.11 (8)° with the S- and C-bound phenyl rings, respectively. The nitro group lies to the same side of the mol­ecule as the oxazoline ring but is orientated so as not to inter­act with the ring. Linear supra­molecular chains along [010] are formed via C—H⋯O and C—H⋯S contacts. Chains are consolidated into a three-dimensional architecture by C—H⋯π and van der Waals inter­actions. PMID:22606161

  20. 1-(4-Chloro­phenyl)-2-[tris­(4-methyl­phenyl)-λ5-phosphanyl­idene]butane-1,3-dione

    PubMed Central

    Sabounchei, Seyyed Javad; Shahriary, Parisa; Hosseini Fashami, Faegheh; Morales-Morales, David; Hernandez-Ortega, Simon

    2013-01-01

    In the title ylide, C31H28ClO2P [common name α-acetyl-α-p-chloro­benzoyl­methyl­enetri(p-tol­yl)phospho­rane], the dihedral angle between the 4-chloro­phenyl ring and that of the ylide moiety is 66.15 (10)°. The geometry around the P atom is slightly distorted tetra­hedral [angle range = 105.22 (8)–115.52 (9)°] and the carbonyl O atoms are syn-oriented with respect to the P atom. The ylide group is close to planar [maximum deviation from the least-squares plane = 0.006 (2) Å] and the P—C, C—C and C=O bond lengths are consistent with electron delocalization involving the O atoms. PMID:23424468

  1. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C88...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  2. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C8...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  3. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C8...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  4. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C88...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  5. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzenamine, N-phenyl-, ar arâ²-(C9... Significant New Uses for Specific Chemical Substances § 721.10023 Benzenamine, N-phenyl-, ar ar′-(C9-rich C8...) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  6. Toward the Oxidation of the Phenyl Radical and Prevention of PAH Formation in Combustion Systems.

    PubMed

    Parker, Dorian S N; Kaiser, Ralf I; Troy, Tyler P; Kostko, Oleg; Ahmed, Musahid; Mebel, Alexander M

    2015-07-16

    The reaction of the phenyl radical (C6H5) with molecular oxygen (O2) plays a central role in the degradation of poly- and monocyclic aromatic radicals in combustion systems which would otherwise react with fuel components to form polycyclic aromatic hydrocarbons (PAHs) and eventually soot. Despite intense theoretical and experimental scrutiny over half a century, the overall reaction channels have not all been experimentally identified. Tunable vacuum ultraviolet photoionization in conjunction with a combustion simulating chemical reactor uniquely provides the complete isomer specific product spectrum and branching ratios of this prototype reaction. In the reaction of phenyl radicals and molecular oxygen at 873 K and 1003 K, ortho-benzoquinone (o-C6H4O2), the phenoxy radical (C6H5O), and cyclopentadienyl radical (C5H5) were identified as primary products formed through emission of atomic hydrogen, atomic oxygen and carbon dioxide. Furan (C4H4O), acrolein (C3H4O), and ketene (C2H2O) were also identified as primary products formed through ring opening and fragmentation of the 7-membered ring 2-oxepinoxy radical. Secondary reaction products para-benzoquinone (p-C6H4O2), phenol (C6H5OH), cyclopentadiene (C5H6), 2,4-cyclopentadienone (C5H4O), vinylacetylene (C4H4), and acetylene (C2H2) were also identified. The pyranyl radical (C5H5O) was not detected; however, electronic structure calculations show that it is formed and isomerizes to 2,4-cyclopentadienone through atomic hydrogen emission. In combustion systems, barrierless phenyl-type radical oxidation reactions could even degrade more complex aromatic radicals. An understanding of these elementary processes is expected to lead to a better understanding toward the elimination of carcinogenic, mutagenic, and environmentally hazardous byproducts of combustion systems such as PAHs.

  7. Synthesis and fuel cell characterization of blend membranes from phenyl phosphine oxide containing flourinated novel polymers

    NASA Astrophysics Data System (ADS)

    Gürtekin Seden, Merve; Baştürk, Emre; Inan, Tülay Y.; Kayaman Apohan, Nilhan; Güngör, Atilla

    2014-12-01

    Novel fluorinated poly(arylene ether)'s are synthesized from polycondensation of bis (p-hydroxy-tetrafluoro) phenyl) phenyl phosphine oxide (PFPPO-OH) with 4,4‧-dichlorodiphenyl sulfone (DCDPS) and 2,2-bis(4-hydroxyphenyl)propane (Bisfenol A) (Copolymer 1a) or 2,2-bis(4-hydroxyphenyl) hexafluoropropane (Bisphenol AF) (Copolymer 1b). The fluorinated copolymers have been blended with sulphonated poly(ether ether ketone)-SPEEK by solvent casting method. The water uptake and proton conductivity of the blend membranes decreases with the increase of copolymer content as expected, but proton conductivity values are still comparable to that of Nafion117® membrane. Addition of hydrophobic copolymer 1b to the SPEEK caused increase in water vapor transmission. Methanol permeability of the membranes is decreased to 8.2 × 10-8 cm2 s-1 and 1.3 × 10-9 cm2 s-1 by addition of Copolymer 1a and 1b, respectively and they are much lower than that of Nafion® 117 (1.21E-06 (cm2 s-1). The blend membranes endure up to 6.5 h before it starts to dissolve. Hydrogen and oxygen permeability of the blend membranes is one-hundredth of the Nafion®. Fluorinated polymer improved chemical, mechanical, and hydrolytic stability and also phenyl phosphine oxide structure in the ionomer increased the thermal stability, gas and methanol permeability and overcomed the drawbacks of the Nafion® type membranes.

  8. 17O NMR studies of ortho-substituent effects in substituted phenyl tosylates.

    PubMed

    Nummert, Vilve; Mäemets, Vahur; Piirsalu, Mare; Koppel, Ilmar A

    2012-10-01

    (17)O NMR spectra for 35 ortho-, para-, and meta-substituted phenyl tosylates (phenyl 4-methylbenzenesulfonates), 4-CH(3)-C(6)H(4) SO(2)OC(6)H(4)-X, at natural abundance in acetonitrile at 50 °C were recorded. The (17)O NMR chemical shifts, δ((17)O), of the sulfonyl (SO(2)) and the single-bonded phenoxy (OPh) oxygens for para and meta derivatives correlated well with dual substituent parameter treatment using the Taft inductive, σ(I), and resonance, σº(R), constants. The influence of ortho substituents on the sulfonyl oxygen and the single-bonded phenoxy oxygen chemical shifts, δ((17)O), was found to be nicely described by the Charton equation: δ((17)O)(ortho) = δ((17)O)(H) + ρ(I)σ(I) + ρ(R)σ°(R) + δE(s)(B) when the data treatment was performed separately for electron-donating +R substituents and electron-attracting -R substituents. Electron-attracting meta and para substituents in the phenyl moiety caused deshielding while the electron-donating meta, para and ortho +R substituents produce shielding effects on the sulfonyl (SO(2)) and single-bonded phenoxy (OPh) oxygens. The influence of ortho inductive and resonance effects in the case of +R substituents was found to be approximately twice higher than the corresponding influence from the para position. Due to the steric effect of ortho substituents a decrease in shielding of the oxygens at the sulfonyl group (δE(s)(B) > 0, E(s)(B) < 0) was detected.

  9. X-ray diffraction investigation of 1-phenyl-3-isopropyl-5-(benzothiazol-2-yl)formazan

    NASA Astrophysics Data System (ADS)

    Slepukhin, P. A.; Pervova, I. G.; Rezinskikh, Z. G.; Lipunova, G. N.; Gorbatenko, Yu. A.; Lipunov, I. N.

    2008-01-01

    The crystal structure of 1-phenyl-3-isopropyl-5-(benzothiazol-2-yl)formazan is investigated using X-ray diffraction. The compound crystallizes in the form of two crystallographically independent molecules ( A and B) in identical conformations that are stabilized by intermolecular hydrogen bonds. The intermolecular hydrogen bonds N-H…N (N…N, 2.892 and 2.939 Å) link molecules into AB dimers. Both molecules have a flattened structure, except for the isopropyl fragment. The bonds in the formazan chains are delocalized. Molecules A and B have close geometric characteristics.

  10. Selectivity of peptide bond dissociation on excitation of a core electron: Effects of a phenyl group

    NASA Astrophysics Data System (ADS)

    Tsai, Cheng-Cheng; Chen, Jien-Lian; Hu, Wei-Ping; Lin, Yi-Shiue; Lin, Huei-Ru; Lee, Tsai-Yun; Lee, Yuan T.; Ni, Chi-Kung; Liu, Chen-Lin

    2016-09-01

    The selective dissociation of a peptide bond upon excitation of a core electron in acetanilide and N-benzylacetamide was investigated. The total-ion-yield near-edge X-ray absorption fine structure spectra were recorded and compared with the predictions from time-dependent density functional theory. The branching ratios for the dissociation of a peptide bond are observed as 16-34% which is quite significant. This study explores the core-excitation, the X-ray photodissociation pathways, and the theoretical explanation of the NEXAFS spectra of organic molecules containing both a peptide bond and a phenyl group.

  11. 2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-3-yl)ethanone

    PubMed Central

    Ye, Fei; Fu, Ying; Zhao, Shuang

    2010-01-01

    In the title mol­ecule, C11H11Cl2NO2, the oxazolidine ring is in an envelope conformation with the O atom forming the flap; the other four essentially planar ring atoms (r.m.s. deviation = 0.012 Å) form a dihedral angle of 91.1 (3)° with the phenyl ring. In the crystal structure, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, forming one-dimensional chains. PMID:21579860

  12. Preconcentration of cadmium and zinc with 1-phenyl-2, 3-dimethlypyrazolone-5-thione

    SciTech Connect

    Bikkulova, A.T.

    1985-08-20

    This paper attempts to ascertain the possibility of use of 1-phenyl-2,3-dimethyl-pyrazolone-5-thione (thiopyrine) for cadmium and zinc concentration in waste waters of oil refineries for their subsequent determination. Cadmium and zinc complexing with thiopyrine in aqueous solutions was studied by the distribution method. Cadmium and zinc in waste waters were determined by a neutron activation technique. The elemental composition and certain properties of halide complexes of cadmium and zinc with thiopyrine are shown. The constants of chloroform extraction of iodide complexes of cadmium and zinc with thiopyrine are shown.

  13. Synthesis and spectral properties of near-infrared aminophenyl-, hydroxyphenyl-, and phenyl-substituted heptamethine cyanines.

    PubMed

    Lee, Hyeran; Mason, J Christian; Achilefu, Samuel

    2008-01-18

    Diverse meso-aminophenyl-, hydroxyphenyl-, and phenyl-substituted heptamethine cyanine dyes were prepared by a modified Suzuki--Miyaura method in good yields. In addition, direct Suzuki coupling of Vilsmeier--Haack reagent extends the procedure to the synthesis of otherwise difficult cyanine dyes containing multiple heteroatoms in the indolium ring. The new compounds possess excellent spectral properties and can be used to label bioactive molecules and nanoparticles. The one-pot synthesis procedure eliminates the cumbersome steps of protecting/deprotecting amino or hydroxy groups.

  14. Comparative XAFS studies of some Cobalt complexes of (3-N- phenyl -thiourea-pentanone-2)

    NASA Astrophysics Data System (ADS)

    soni, Namrata; Parsai, Neetu; Mishra, Ashutosh

    2016-10-01

    XAFS spectroscopy is a useful method for determining the local structure around a specific atom in disordered systems. XAFS study of some cobalt complexes of (3-N-phenyle- thiourea-pentanon-2) is carried out using the latest XAFS analysis software Demeter with Strawberry Perl. The same study is also carried out theoretically using Mathcad software. It is found that the thiourea has significant influence in the spectra and the results obtained experimentally and theoretically are in agreement. Fourier transform of the experimental and theoretically generated XAFS have been taken to obtain first shell radial distance. The values so obtained are in agreement with each other.

  15. Phenylated polyimides prepared from 3,6-diarylpyromellitic dianhydride and aromatic diamines

    NASA Technical Reports Server (NTRS)

    Harris, Frank W. (Inventor)

    1992-01-01

    A new class of soluble phenylated polyimides made from 3,6-diarypyromellitic dianhydride and process for the manufacture of the 3,6-diarypyromellitic dianhydride starting material. The polyimides obtained with said dianhydride are readily soluble in appropriate organic solvents and are distinguished by excellent thermal, electrical and/or mechanical properties making the polyimides ideally suited as coating materials for microelectronic apparatii, as membranes for selective molecular separation or permeation or selective gas separation or permeation, or as reinforcing fibers in molecular composites, or as high modulus, high tensile strength fibers.

  16. Acute Oral Toxicity (LD50) of 4-Nitrophenyl Monochloromethyl (Phenyl) Phosphinate (TA009) in Male Rats

    DTIC Science & Technology

    1984-10-01

    phosphinates hydrolyze readily in aqueous solutions, a vehicle which would minimize the rate of hydrolysis was required. A mixture of Tween 80 (Fisher...monochloroiethyl (phenyl) phosphinat_. formulated with Tween 80 , EtOH, and citrate buffer (LAIR SOP-OP-STX-45, Preparation of Compounds Unstable in Water...phosphinate. 16.0 ml Tween 80 8.0 ml (100 %) ethanol, 56.0 ml citrate buffer (50 mM) at a pH of 3.2. The vehicle was the same as above without phosphinate. pH

  17. Acute Oral Toxicity (LD50) of 4-Nitrophenyl Monochloromethyl (Phenyl) Phosphinate (TA009) in Female Rats

    DTIC Science & Technology

    1984-10-01

    chosen was a mixture of Tween 80 (Fisher Scientific Company, Fairlawn, NJ) ethanol and citrate buffer (pH 2.9). Additional information on the vehicle...phosphinate formulated with Tween 80 , EtOH, and citrate buffer (LAIR SOP-OP-STX-45, Preparation of Compounds Unstable in Water for SLRL Assay). A 2.0...percent phosphinate solution was prepared with 1.5 g 4- nitrophenyl monochloromethyl (phenyl) phosphinate. 15.0 ml Tween 80 7.5 ml (100 %) ethanol

  18. Discovery of a novel series of phenyl pyrazole inner salts based on fipronil as potential dual-target insecticides.

    PubMed

    Jiang, Dingxin; Zheng, Xiaohua; Shao, Guang; Ling, Zhang; Xu, Hanhong

    2014-04-23

    A series of novel phenyl pyrazole inner salt derivatives based on fipronil were designed and synthesized in the search for dual-target insecticides. These compounds were designed to target two families of nicotinic acetylcholine receptors and γ-aminobutyric acid receptors. The insecticidal activities of the new compounds against diamondback moth (Plutella xylostella) were evaluated. The results of bioassays indicated that most of the inner salts showed moderate to high activities, of which the phenyl pyrazole inner salts containing quinoline had excellent biological activity. Previous structure-activity relationship studies revealed that a suitable structure of the quaternary ammonium salts was critical for the bioactivity of phenyl pyrazole inner salts, which contribute to exposing the cationic nitrogen to bind to the receptor (for instance, nicotinic acetylcholine receptors) and possibly interact with the receptor via hydrogen bonding and cooperative π-π interaction. The present work demonstrates that the insecticidal potency of phenyl pyrazole inner salts holds promise for the development new dual-target phenyl pyrazole insecticides.

  19. Isolation and antifungal activity of 4-phenyl-3-butenoic acid from Streptomyces koyangensis strain VK-A60.

    PubMed

    Lee, Jee Yeon; Lee, Jung Yeop; Moon, Surk Sik; Hwang, Byung Kook

    2005-10-05

    An antifungal compound was isolated from the culture broth of Streptomyces koyangensis strain VK-A60 using various chromatographic procedures. On the basis of the high-resolution EI-mass and 1H and 13C NMR data, the compound was identified as 4-phenyl-3-butenoic acid. Colletotrichum orbiculare, Magnaporthe grisea, and Pythium ultimum were most sensitive to 4-phenyl-3-butenoic acid. Strong inhibitory effects of 4-phenyl-3-butenoic acid also were found against Pectobacterium carotovorum subsp. carotovorum and Ralstonia solanacearum. 4-Phenyl-3-butenoic acid effectively suppressed the development of M. grisea on rice leaves at the concentration of more than 10 microg/mL, and the protective activity was in general similar to that of the commercial fungicide tricyclazole. Treatment with 100 microg/mL of 4-phenyl-3-butenoic acid also effectively inhibited the anthracnose development on cucumber plants, although its in vivo efficacy was somewhat less effective than that of the commercial fungicide chlorothalonil.

  20. (η5-Penta­methyl­cyclo­penta­dien­yl)(η6-4-phenyl­butan-2-one)ruthenium(II) tetra­phenyl­borate

    PubMed Central

    Loughrey, Bradley T.; Williams, Michael L.; Healy, Peter C.

    2010-01-01

    The title compound, [Ru(C10H15)(C10H12O)][B(C6H5)4], crystallizes as discrete (η5-penta­methyl­cyclo­penta­dien­yl)Ru(η6-4-phenyl­butan-2-one)]+ cations and [BPh4]− anions. In the cation, the non-H atoms of the butan-2-one group are approximately planar (r.m.s. deviation = 0.056 Å) and lie nearly perpendicular to the plane of the phenyl ring with a dihedral angle between the two planes of 69.3 (1)°. No significant C—H⋯O inter­actions are observed between the methyl and phenyl H atoms and the carbonyl O atom. PMID:21589253

  1. Reaction of (chloro carbonyl) phenyl ketene with 5-amino pyrazolones: Synthesis, characterization and theoretical studies of 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives

    NASA Astrophysics Data System (ADS)

    Zahedifar, Mahboobeh; Razavi, Razieh; Sheibani, Hassan

    2016-12-01

    New 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives were synthesized from the reaction of (chlorocarbonyl)phenyl ketene and 5-amino pyrazolones in high to excellent yields and short reaction times. Structures of the new compounds were fully characterized by their spectral data IR, 1H NMR, and 13C NMR and by the theoretical results. Density Functional Theory (DFT) was used to optimize the structures, compute the energies and vibrational frequencies IR and 1H NMR shielding tensors of the desired products. The theoretical results excellent are compared with the experimental data.

  2. (3R,4S)-3-Methyl-4-phenyl-2-[(R)-1-phenyl­eth­yl]-3,4-di­hydro­isoquinolin-2-ium tetra­fluorido­borate

    PubMed Central

    Ben Ali, Karim; Retailleau, Pascal

    2014-01-01

    The title salt, C24H24N+·BF4 −, is one of two possible dias­tereoisomers having a different configuration of the asymmetric centre in the α-phenyl­ethyl substituent, whose absolute configuration was established to be R. The two phenyl substituents of the cation have a cofacial orientation, albeit with a long centroid–centroid separation of 4.129 (3) Å. The crystal structure exhibits numerous C—H⋯F contacts between counter-ions, with the tetra­fluorido­borate anion surrounded by five iminium cations. PMID:24764972

  3. 2-[(1R,3S)-6,7-Dimeth­oxy-1-phenyl-1,2,3,4-tetra­hydro­isoquinolin-3-yl]-4-phenyl-1,3-thia­zole

    PubMed Central

    Pawar, Sunayna; Katharigatta, Venugopala; Govender, Thavendran; Kruger, Hendrik G.; Maguire, Glenn E. M.

    2011-01-01

    In the title compound, C26H24N2O2S, the dihedral angle between the thia­zole ring and the adjacent phenyl ring is 3.02 (15)°. The N-containing six-membered ring of the tetra­hydro­isoquinoline unit adopts a half-chair conformation. The dihedral angle between the least-squares plane of the tetra­hydro­isoquinoline ring system and its nearest phenyl ring is 76.90 (13)°. No classical hydrogen bonds nor π–π inter­actions were found in the crystal structure. PMID:22065627

  4. Single-molecule phenyl-acetylene-macrocycle-based optoelectronic switch functioning as a quantum-interference-effect transistor.

    PubMed

    Hsu, Liang-Yan; Rabitz, Herschel

    2012-11-02

    This work proposes a new type of optoelectronic switch, the phenyl-acetylene-macrocycle-based single-molecule transistor, which utilizes photon-assisted tunneling and destructive quantum interference. The analysis uses single-particle Green's functions along with Floquet theory. Without the optical field, phenyl-acetylene-macrocycle exhibits a wide range of strong antiresonance between its frontier orbitals. The simulations show large on-off ratios (over 10(4)) and measurable currents (~10(-11) A) enabled by photon-assisted tunneling in a weak optical field (~2 × 10(5) V/cm) and at a small source-drain voltage (~0.05 V). Field amplitude power scaling laws and a range of field intensities are given for operating one- and two-photon assisted tunneling in phenyl-acetylene-macrocycle-based single-molecule transistors. This development opens up a new direction for creating molecular switches.

  5. 1-Ethyl-2-phenyl-3-[2-(tri-methyl-sil-yl)ethyn-yl]-1H-indole.

    PubMed

    Baglai, Iaroslav; Maraval, Valérie; Duhayon, Carine; Chauvin, Remi

    2013-06-01

    The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with tri-methyl-silyl-acetyl-ene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C-H⋯π inter-actions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the tri-methyl-silyl unit are equally disordered over two sets of sites.

  6. Preparation of nanosheet by exfoliation of layered iron phenyl phosphate under ultrasonic irradiation

    SciTech Connect

    Tanaka, Hidekazu Okumiya, Takeshi; Ueda, Shun-kichi; Taketani, Yukihiko; Murakami, Masahiko

    2009-02-04

    Synthetic layered iron phenyl phosphate (Fe(OH)(C{sub 6}H{sub 5}PO{sub 4}H){sub 1.6}(H{sub 2}PO{sub 4}){sub 0.4}.5.1H{sub 2}O: FePP), which is composed of a multilayer alternating bilayer of phenyl groups of the phosphates and amorphous iron phosphate phase, was exfoliated in ethanol under ultrasonic irradiation. The exfoliation of FePP was recognized at 10-10,000 ppm of FePP concentration. No reaggregation and reprecipitation of the nanosheets took place for at least 6 months of standing at room temperature. The UV-vis measurements indicated that the nanosheet dispersing solution possessed a UV absorption property which would be due to the charge transfer transition of Fe-O. The FePP nanosheet-doped silica gel with UV absorption property could be prepared by sol-gel process. The Beer's plot and EDX elemental mapping analysis for Fe and P revealed that the nanosheets are homogeneously dispersed in the silica gels.

  7. Bioconversion of 6-(N-methyl-N-phenyl)aminomethyl androstane steroids by Nocardioides simplex.

    PubMed

    Sukhodolskaya, Galina; Fokina, Victoria; Shutov, Andrei; Nikolayeva, Vera; Savinova, Tatiana; Grishin, Yuri; Kazantsev, Alexey; Lukashev, Nikolay; Donova, Marina

    2017-02-01

    The newly synthesized (α/β)-diastereomers of 6-(N-methyl-N-phenyl)aminomethylandrost-4-ene-3,17-dione (5) and 6-(N-methyl-N-phenyl)aminomethylandrost-4-en-17β-ol-3-one (6) were firstly investigated as substrates for the whole cells of Nocardioides simplex VKM Ac-2033D in comparison with their unsubstituted analogs, - androst-4-ene-3,17-dione (1) and androst-4-en-17β-ol-3-one (2). 1(2)-Dehydroderivatives were identified as the major bioconversion products from all the substrates tested. When using the mixtures of (α/β)-stereoisomers of 5 and 6 as the substrates, only β-stereoisomers of the corresponding 1,4-diene-steroids were formed. Along with 1(2)-dehydrogenation, N. simplex VKM Ac-2033D promoted oxidation of the hydroxyl group at C-17 position of 6: both 6(α) and 6(β) were transformed to the corresponding 17-keto derivatives. No steroid core destruction was observed during the conversion of the 6-substituted androstanes 5 and 6, while it was significant when 1 or 2 was used as the substrate. The results suggested high potentials of N. simplex VKM Ac-2033D for the generation of novel 1(2)-dehydroanalogs.

  8. [Synthesis and theoretical study on fluorescence property of 4- (2-hydroxybenzylideneamino) phenyl ethanone schiff base].

    PubMed

    Liang, Xiao-Rui; Wang, Gang; Jiang, Yan-Lan; Qu, Cheng-Li; Wang, Xiu-Juan; Zhao, Bo

    2013-12-01

    Using salicylaldehyde and 4-aminophenyl ethanone as raw material, a Schiff base derivative 4-(2-hydroxybenzylidene-amino) phenyl ethanone was synthesized by the solid phase reaction method at room temperature. The structure of the product was characterized by elemental analysis and 1 HNMR The UV spectra, fluorescence emission spectra and fluorescence quantum yield of the title Schiff base derivative were investigated. The results showed that this Schiff base displayed superior fluorescence property. The ground state configuration of the title Schiff base was optimized by density functional theory (DFT) method at the B3LYP/6-311G level. After vibrational analysis, there is no imaginary frequency, which indicates that the structure is stable. Then the ground state configuration was optimized to the excited state configuration by the method of single excited interactions CIS. Based on the optimized structure for the ground state and excited state time-dependent density functional theory (TD-DFT) calculations were carried out at the B3LYP/6-31G level to predict the absorption spectra and the fluorescence spectra. The results show that the computed spectra were comparable with the spectra from the experiments. The relationship between the molecular structure and the fluorescence property of 4-(2-hydroxybenzylideneamino) phenyl ethanone was also discussed. The results obtained may provide some theoretical guidance for the design of new fluorescence compounds.

  9. Fluoro-substituted tetraphenyl-phenyl grafted polysiloxanes as highly selective stationary phases for gas chromatography.

    PubMed

    Han, Xue; He, Xinxin; Wang, Huan; Wang, Bing; Wu, Bo

    2016-06-03

    In this work, two new types of polycyclic aromatic grafted polysiloxanes, namely, 3,4-bis(4-fluoro phenyl)-2,5-diphenyl polysiloxane (FPP) and 3,4-bis(3,4,5-trifluoro phenyl)-2,5-diphenyl polysiloxane (TFPP), were synthesized and statically coated onto capillary columns as stationary phases for gas chromatography (GC). Based on their McReynolds constants, both columns exhibited moderate polarity. The efficiencies of the FPP and TFPP columns were 3316 (k=3.96, naphthalene; 0.25mm inner diameter) and 3768 (k=4.14, naphthalene; 0.25mm inner diameter) plates/m, respectively. The thermostability of the polymers was tested by thermogravimetric analysis (TGA), and results revealed that both TFPP and FPP began to decompose slightly at 380°C. Separation of polyethylene pyrolysis products showed that the upper working temperature of the two columns can reach up to 360°C. Relying on their unique polarizable characteristics in combination with other types of interactions, such as H-bond acceptor, dipole-dipole, and dispersive interactions, the newly synthesized polarizable stationary phases offered unique selectivity for aromatic isomers and substituted benzenes. A slight separation difference between TPP and TFPP was observed. TFPP also exerted excellent selectivity for polycyclic aromatic hydrocarbons, fatty acid esters, and fatty alcohols. Overall, FPP and TFPP demonstrated considerable potential for further applications because of their unique structures and outstanding separation performance.

  10. Contrasting retrogressive rearrangement pathways during thermolysis of silica-immobilized benzyl phenyl ether

    SciTech Connect

    Buchanan, A.C. III; Britt, P.F.; Skeen, J.T.

    1997-03-01

    Many coal model compound studies have focused on the mechanisms of bond cleavage reactions, and the means to alter reaction conditions to promote such reactions. However, there has become increasing interest in elucidating mechanisms associated with retrogressive or retrograde reactions in coal processing, which involve the formation of refractory bonds. Retrograde reactions inhibit efficient thermochemical processing of coals into liquid fuels, which has been particularly well-documented for low rank coals where abundant oxygen-containing functional groups are thought to play a key role in the chemistry. Much less is known about retrogressive reactions for ether-containing model compounds. Radical recombination through ring coupling of phenoxy radicals in benzyl phenyl ether (BPE) is known to lead to more refractory diphenylmethane linkages to a limited extent. Since this chemistry may be attributed at least in part to cage recombination, it could be promoted in a diffusionally constrained environment such as in the coal macromolecule. Using silica-immobilization to simulate restricted diffusion in coal, the authors have found that retrogressive reactions can be promoted for certain hydrocarbon model compounds. The authors have now begun an examination of the thermolysis behavior of silica-immobilized benzyl phenyl ether at 275--325 C. The initial results indicate that two retrogressive reaction pathways, radical recombination and molecular rearrangement through Si-O-C linkage to the surface of PhOCH{center_dot}Ph, are promoted by restricted diffusion. Remarkably, the retrograde products typically account for 50 mol% of the thermolysis products.

  11. Kinetic resolution of racemic 1-phenyl 1-propanol by lipase catalyzed enantioselective esterification reaction.

    PubMed

    Karadeniz, Fatma; Bayraktar, Emine; Mehmetoglu, Ulkü

    2010-10-01

    In this study, resolution of (R,S)-1-phenyl 1-propanol by lipase-catalyzed enantioselective esterification was achieved. To investigate the effect of lipase type on enantiomeric excess, three different lipases were used. Novozym 435 exhibited the highest enantioselectivity for resolution of (R,S)-1-phenyl 1-propanol. The effects of carbon length of fatty acids from C12 to C16, which were used as acyl donor, organic solvents with Log P values from 0.5 to 4.5, acyl donor/alcohol molar ratio (1:1, 3:2, 2:1, 3:1), amount of added molecular sieves (0-133.2 kg/m(3)), and temperature (10-60° C) on the enantioselectivity were investigated. The best reaction conditions were comprised of using toluene (Log P= 2.5) as solvent, lauric acid (12C) as acyl donor, 133.2 kg/m(3) molecular sieves at 50° C and acyl donor/alcohol molar ratio as 1:1. Under these conditions, the enantiomeric excess of S enantiomer ee (S) was obtained as 95% for a reaction time of 2.5 hours.

  12. Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media

    PubMed Central

    Devendran, Saravanan; Yadav, Ganapati D.

    2014-01-01

    Kinetic resolution of 1-phenyl-2-propyn-1-ol, an important chiral synthon, was studied through trans-esterification with acyl acetate to investigate synergism between microwave irradiation and enzyme catalysis. Lipases from different microbial origins were employed for the kinetic resolution of (R/S)-1-phenyl-2-propyn-1-ol, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n-hexane as solvent. Vinyl acetate was the most effective among different acyl esters studied. The effect of various parameters was studied in a systematic manner. Definite synergism between microwave and enzyme was observed. The initial rate was improved around 1.28 times under microwave irradiation than conventional heating. Under optimum conditions, maximum conversion (48.78%) and high enantiomeric excess (93.25%) were obtained in 2 h. From modeling studies, it is concluded that the reaction follows the Ping-Pong bi-bi mechanism with dead end alcohol inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is green, clean, and easily scalable as compared to the chemical process. PMID:24707487

  13. Base-pairing selectivity of a ureido-linked phenyl-2'-deoxycytidine derivative.

    PubMed

    Nakano, Shu-ichi; Oka, Hirohito; Yamaguchi, Daisuke; Fujii, Masayuki; Sugimoto, Naoki

    2012-12-28

    Incorporation of modified nucleotides into nucleic acid strands often produces conformational constraints and steric hindrances that may change the property of base pairing. In this study, we investigated a 2'-deoxycytidine derivative that tethers a phenyl moiety to the exocyclic amino group of cytosine linked through a ureido group. This derivative compound is structurally similar to the carbamoylated DNA base lesions produced in cells. The thermodynamic and structural studies showed that the modified dC formed the base pair with dG in the complementary strand, but the base-pairing selectivity toward dG was decreased under poly(ethylene glycol)-mediated osmotic stress. The phenyl group and the ureido linker attached to dC provided selectivity for the formation of base pairing exclusively with dG in a wide range of pH conditions, whereas unmodified dC stabilized the pairings with dA or dC in acidic solutions. Moreover, this modified base could not form self-pairing through intermolecular hydrogen bonds. We suggest that formation of weak pairing and protonation of the cytosine base are hindered due to the base modification. These data provide insights into the pairing selectivity of carbamoylated cytosine lesions produced in cells, and suggest applications of the 2'-deoxycytidine derivatives in medical technologies, molecular biology experiments, and synthesis of a supramolecular network of DNA strands.

  14. Enhanced dispersion of multiwall carbon nanotubes in natural rubber latex nanocomposites by surfactants bearing phenyl groups.

    PubMed

    Mohamed, Azmi; Anas, Argo Khoirul; Bakar, Suriani Abu; Ardyani, Tretya; Zin, Wan Manshol W; Ibrahim, Sofian; Sagisaka, Masanobu; Brown, Paul; Eastoe, Julian

    2015-10-01

    Here is presented a systematic study of the dispersibility of multiwall carbon nanotubes (MWCNTs) in natural rubber latex (NR-latex) assisted by a series of single-, double-, and triple-sulfosuccinate anionic surfactants containing phenyl ring moieties. Optical polarising microscopy, field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), and Raman spectroscopy have been performed to obtain the dispersion-level profiles of the MWCNTs in the nanocomposites. Interestingly, a triple-chain, phenyl-containing surfactant, namely sodium 1,5-dioxo-1,5-bis(3-phenylpropoxy)-3-((3-phenylpropoxy)carbonyl) pentane-2-sulfonate (TCPh), has a greater capacity the stabilisation of MWCNTs than a commercially available single-chain sodium dodecylbenzenesulfonate (SDBS) surfactant. TCPh provides significant enhancements in the electrical conductivity of nanocomposites, up to ∼10(-2) S cm(-1), as measured by a four-point probe instrument. These results have allowed compilation of a road map for the design of surfactant architectures capable of providing the homogeneous dispersion of MWCNTs required for the next generation of polymer-carbon-nanotube materials, specifically those used in aerospace technology.

  15. The structure of titanium-rhodium heterobinuclear complexes with. mu. -phenyl ligands

    SciTech Connect

    Park, Joon Won; Henling, L.M.; Schaefer, W.P.; Grubbs, R.H. )

    1991-01-01

    The heteronuclear {mu}-methylene {mu}-phenyl complexes CP{sub 2}Ti({mu}-CH{sub 2})({mu}-p-(CH{sub 3}){sub 2}NC{sub 6}H{sub 4})Rh(1,5-COD) (3b) (1,5-COD = 1,5-cyclooctadiene) and Cp{sub 2}Ti({mu}-CH{sub 2})({mu}-o-MeOC{sub 6}H{sub 4})Rh(1,5-COD) (3c) were synthesized from Cp{sub 2}Ti({mu}-CH{sub 2})({mu}-Cl)Rh(1,5-COD) (1) and the appropriate aromatic lithium reagent. Thes tructure of 3b was determined by single-crystal X-ray crystallography. The two metal atoms are bridged by the {mu}-methylene carbon remaining from 1 and by ipso carbon of the p-(N,N-dimethylamino)phenyl group. Compound 3b crystallizes in the triclinic system, in space group P{bar 1} (No. 2), with a = 8.988 (1) {angstrom}, b = 10.169 (1) {angstrom}, c = 13.707 (2) {angstrom}, {alpha} = 102.85 (1){degree}, {beta} = 103.47 (1){degree}, {gamma} = 101.36 (1){degree}, V = 1,146.2 (2) {angstrom}{sup 3}, and Z = 2. The structure was solved and refined with a final R = 0.0370 by using 3,882 independent reflections. Complex 3c was shown to have a similar structure by spectroscopic comparison to 3b.

  16. α-Phenyl-N-cyclohexyl Nitrones: Preparation and Use as Spin-Traps.

    PubMed

    Durand, Grégory; Rosselin, Marie; Klein, Pierre-André; Zéamari, Kamal; Choteau, Fanny; Tuccio, Béatrice

    2017-01-06

    Two bifunctional α-phenyl-N-cyclohexyl nitrones were synthesized with the expectation that the cyclohexyl ring will impart lipophilicity to the molecule, high reactivity to the nitronyl group, and stability to the spin adducts formed. The synthesis of the acid nitrone 4 and its corresponding tert-butyl ester 3 was initiated by a Michael reaction to introduce the cyclohexyl ring. A Zn/AcOH-mediated reduction of the nitro functionality followed by condensation onto benzaldehyde generated the nitronyl function. In agreement with their high lipophilicity values, nitrone 3 was insoluble in water, while nitrone 4 exhibited a poor water solubility. It was determined that the presence of the cyclohexyl ring did not affect either the reduction or oxidation potentials of the nitronyl group in comparison to the classical α-phenyl-N-tert-butylnitrone (PBN). The spin trapping ability of 3 and 4 was investigated by EPR for oxygen- and carbon-centered radicals. In most cases, the nitrones gave rise to a standard six-line EPR spectrum whose values were in agreement with the literature, accompanied by a minor second species. In DMSO, the half-lives of nitrone 3 and 4-OOH adducts were double that of PBN, suggesting that the stabilization comes from the cyclohexyl ring and/or the electronic effect of the carboxylic acid.

  17. 6-Butyryl-5-hy­droxy-4-phenyl­seselin

    PubMed Central

    Aree, Thammarat; Tip-pyang, Santi; Sowanthip, Preecha

    2010-01-01

    In the title coumarin compound (systematic name: 6-butyryl-5-hy­droxy-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b;3,4-b′]dipyran-2-one), C24H22O5, also known as mammea A/AC cyclo D, the chromene and pyran rings are almost coplanar with a maximum deviation from the mean plane of 0.295 (2) Å. The attached phenyl group is inclined at 53.49 (8)° with respect to the chromene ring. The mol­ecular structure is stabilized by an intra­molecular O—H⋯O hydrogen bond. In the crystal, mol­ecules are linked into sheets parallel to (101) by inter­molecular C—H⋯O hydrogen bonds. Adjacent sheets are sustained by inter­molecular C—H⋯π and π–π [centroid–centroid distance = 4.471 (2) Å] inter­actions. PMID:21588783

  18. Covalent modification of calcium hydroxyapatite surface by grafting phenyl phosphonate moieties

    SciTech Connect

    Aissa, Abdallah; Debbabi, Mongi; Gruselle, Michel Thouvenot, Rene; Gredin, Patrick; Traksmaa, Rainer; Tonsuaadu, Kaia

    2007-08-15

    The reaction between phenyl phosphonic dichloride (C{sub 6}H{sub 5}P(O)Cl{sub 2}) and synthetic calcium hydroxy- and fluorapatite has been investigated. The presence of mono- or polymeric (C{sub 6}H{sub 5}PO) fragment bound to hydroxyapatite was evidenced by IR, and solid-state {sup 31}P NMR spectroscopy. X-ray powder analysis has shown that the apatitic structure remains unchanged during the reaction. In contrast, no reaction was found using fluorapatite. According to the results found for these two different apatites a mechanism was proposed for the formation of covalent P-O-P bonds as the result of a reaction between the C{sub 6}H{sub 5}P(O)Cl{sub 2} organic reagent and (HPO{sub 4}){sup -} and/or OH{sup -} ions of the hydroxyapatite. - Graphical abstract: Representation of the first step of the reaction between the phenyl phosphonic dichloride and the hydroxyl groups on the surface of the apatite, leading to covalent P-O-P bond with elimination of HCl.

  19. Hydrolytic metabolism of phenyl and benzyl salicylates, fragrances and flavoring agents in foods, by microsomes of rat and human tissues.

    PubMed

    Ozaki, Hitomi; Sugihara, Kazumi; Tamura, Yuki; Fujino, Chieri; Watanabe, Yoko; Uramaru, Naoto; Sone, Tomomichi; Ohta, Shigeru; Kitamura, Shigeyuki

    2015-12-01

    Salicylates are used as fragrance and flavor ingredients for foods, as UV absorbers and as medicines. Here, we examined the hydrolytic metabolism of phenyl and benzyl salicylates by various tissue microsomes and plasma of rats, and by human liver and small-intestinal microsomes. Both salicylates were readily hydrolyzed by tissue microsomes, predominantly in small intestine, followed by liver, although phenyl salicylate was much more rapidly hydrolyzed than benzyl salicylate. The liver and small-intestinal microsomal hydrolase activities were completely inhibited by bis(4-nitrophenyl)phosphate, and could be extracted with Triton X-100. Phenyl salicylate-hydrolyzing activity was co-eluted with carboxylesterase activity by anion exchange column chromatography of the Triton X-100 extracts of liver and small-intestinal microsomes. Expression of rat liver and small-intestinal isoforms of carboxylesterase, Ces1e and Ces2c (AB010632), in COS cells resulted in significant phenyl salicylate-hydrolyzing activities with the same specific activities as those of liver and small-intestinal microsomes, respectively. Human small-intestinal microsomes also exhibited higher hydrolyzing activity than liver microsomes towards these salicylates. Human CES1 and CES2 isozymes expressed in COS cells both readily hydrolyzed phenyl salicylate, but the activity of CES2 was higher than that of CES1. These results indicate that significant amounts of salicylic acid might be formed by microsomal hydrolysis of phenyl and benzyl salicylates in vivo. The possible pharmacological and toxicological effects of salicylic acid released from salicylates present in commercial products should be considered.

  20. 2,3,5-Triphenyl-2H-tetra­zol-3-ium tetra­phenyl­borate

    PubMed Central

    Fun, Hoong-Kun; Chia, Tze Shyang; Mostafa, Gamal A. E.; Hefnawy, Mohamed M.; Abdel-Aziz, Hatem A.

    2012-01-01

    In the title salt, C19H15N4 +·C24H20B−, the tetra­phenyl­borate anion is in a tetra­hedral geometry around the B atom [C—B—C angles of 107.10 (9)–111.79 (9)°]. In the cation, the tetra­zole ring makes dihedral angles of 3.04 (7), 51.75 (7) and 51.13 (7)° with the attached phenyl rings. In the crystal, C—H⋯π inter­actions link the cations and anions into ion pairs. PMID:22904995

  1. N,N'-Bis(3-phenyl-prop-2-en-1-yl-idene)-2,2'-disulfanediyldianiline.

    PubMed

    Raftery, James; Jhaumeer-Laulloo, Sabina; Bhowon, Minu G; Chikhooree, Kiran; Joule, John A

    2010-11-27

    In the title compound, C(30)H(24)N(2)S(2), the two phenyl rings attached to the S atoms are oriented nearly perpendicularly, making a dihedral angle of 86.14 (8)°. Each of the two ArCH=CHCH=N units is almost planar, having maximum deviations from the least-squares planes of 0.125 and 0.149 Å, and rotated around the C-N bonds relative to the adjacent phenyl ring by 110.26 and 30.30°.

  2. 2-Carbaborane-3-phenyl-1H-indoles--synthesis via McMurry reaction and cyclooxygenase (COX) inhibition activity.

    PubMed

    Laube, Markus; Neumann, Wilma; Scholz, Matthias; Lönnecke, Peter; Crews, Brenda; Marnett, Lawrence J; Pietzsch, Jens; Kniess, Torsten; Hey-Hawkins, Evamarie

    2013-02-01

    Cyclooxygenase-2 (COX-2) inhibitors have been the focus of medicinal chemistry efforts for years, and many compounds that exhibit high selectivity and affinity have been developed. As carbaboranes represent interesting pharmacophores as phenyl mimetics in drug development, this paper presents the synthesis of carbaboranyl derivatives of COX-2-selective 2,3-disubstituted indoles. Despite the lability of carbaboranes under reducing conditions, 2-carbaborane-3-phenyl-1H-indoles could be synthesized by McMurry cyclization of the corresponding amides. Whereas the meta-carbaboranyl-substituted derivatives lacked COX inhibitory activity, an ortho-carbaboranyl analogue was active, but showed a selectivity shift toward COX-1.

  3. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  4. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  5. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  6. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  7. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  8. 40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Carbon black, 4- substituted] phenyl- modified, sodium salts (generic). 721.10075 Section 721.10075 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  9. 40 CFR 721.5930 - Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic name). 721.5930 Section 721.5930 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL...

  10. 1-Phenyl-3-methyl-4-benzoylpyrazol-5-one as a group-extraction reagent for spectrophotometric determination of trace elements.

    PubMed

    Mirza, M Y; Nwabue, F I

    1981-01-01

    1-Phenyl-3-methyl-4-benzoylpyrazol-5-one has been examined as a regent for detection and solvent extraction of metal ions. The reagent seems to be promising as a group-extraction reagent for the spectrophotometric determination of copper, nickel, cobalt, manganese, zinc, chromium(VI) and molybdenum(VI).

  11. Spectrophotometric determination of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid in pure form and in pharmaceuticals.

    PubMed

    Bazel, Yaroslav; Hunka, Iryna; Kormosh, Zholt; Andruch, Vasil

    2009-12-01

    A new sensitive and selective spectrophotometric method has been developed for the determination of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid in pharmaceuticals in the presence of nicotinic acid. The method is based on the reaction of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid with 1,3,3-trimethyl-5-phenyl-2-[3-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-propenyl]-3H-indolium chloride (PIC) followed by the extraction of the formed ion associate into toluene and spectrophotometric detection at 581 nm. Appropriate experimental conditions were found to be pH 7.8-9.8 and 3.6x10(-4) mol L(-1) of PIC. The molar absorptivity is 5.0x10(-4) L mol(-1) cm(-1). The absorbance obeys Beer's law in the range 0.61-12.60 microg mL(-1) of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid, and the detection limit calculated from a blank test was 0.20 microg mL(-1).

  12. pi-Selective stationary phases: (II) Adsorption behavior of substituted aromatic compounds on n-alkyl-phenyl stationary phases

    SciTech Connect

    Gritti, Fabrice; Guiochon, Georges A; Mayfield, Kirsty; Dennis, Gary; Shalliker, R. Andrew

    2010-01-01

    The frontal analysis method was used to measure the adsorption isotherms of phenol, 4-chlorophenol, p-cresol, 4-methoxyphenol and caffeine on a series of columns packed with home-made alkyl-phenyl bonded silica particles. These ligands consist of a phenyl ring tethered to the silica support via a carbon chain of length ranging from 0 to 4 atoms. The adsorption isotherm models that fit best to the data account for solute-solute interactions that are likely caused by p-p interactions occurring between aromatic compounds and the phenyl group of the ligand. These interactions are the dominant factor responsible for the separation of low molecular weight aromatic compounds on these phenyl-type stationary phases. The saturation capacities depend on whether the spacer of the ligands have an even or an odd number of carbon atoms, with the even alkyl chain lengths having a greater saturation capacity than the odd alkyl chain lengths. The trends in the adsorption equilibrium constant are also significantly different for the even and the odd chain length ligands.

  13. An evaluation of 3,4-methylenedioxy phenyl replacements in the aminopiperidine chromone class of MCHr1 antagonists.

    PubMed

    Iyengar, Rajesh R; Lynch, John K; Mulhern, Mathew M; Judd, Andrew S; Freeman, Jennifer C; Gao, Ju; Souers, Andrew J; Zhao, Gang; Wodka, Dariusz; Doug Falls, H; Brodjian, Sevan; Dayton, Brian D; Reilly, Regina M; Swanson, Sue; Su, Zhi; Martin, Ruth L; Leitza, Sandra T; Houseman, Kathryn A; Diaz, Gilbert; Collins, Christine A; Sham, Hing L; Kym, Philip R

    2007-02-15

    The optimization of potent MCHr1 antagonist 1 with respect to improving its in vitro profile by replacement of the 3,4-methylenedioxy phenyl (piperonyl) moiety led to the discovery of 19, a compound that showed excellent MCHr1 binding and functional potencies in addition to possessing superior hERG separation, CYP3A4 profile, and receptor cross-reactivity profiles.

  14. Separation of hexabromocyclododecane diastereomers: Application of C18 and phenyl-hexyl ultra-performance liquid chromatography columns.

    PubMed

    Baek, Song-Yee; Lee, Sunyoung; Kim, Byungjoo

    2017-03-10

    This study was performed to establish the proper liquid chromatographic conditions for the separation of hexabromocyclododecane (HBCD) diastereomers. Column selectivity towards HBCD diastereomers was evaluated for C18 and phenyl-hexyl stationary phases. First, the baseline separation of the primary HBCDs (α-, β-, and γ-HBCD) was obtained using the ultra-performance liquid chromatography (UPLC) column with C18 stationary phase chosen in most previous studies for HBCD analysis; however, co-elution of δ- and ε-HBCD with the primary HBCD diastereomers was observed. To prevent the interference from δ- and ε-HBCD, we adopted a phenyl-hexyl UPLC column to resolve the HBCD diastereomers. The phenyl-hexyl UPLC column showed significantly different selectivity for the HBCD diastereomers compared with the C18 column, which allowed the clear isolation of δ-HBCD and ε-HBCD from the primary HBCD diastereomers. In addition, by checking the retention times of all HBCD diastereomers using both C18 and phenyl-hexyl columns, we confirmed the presence of δ-, ε-, η-, and θ-HBCDs in two technical HBCD mixtures.

  15. Synthesis and Luminescent Property of Poly(9-(3-vinyl-phenyl)-anthracene).

    PubMed

    Lee, Sunmi; Shin, Hwangyu; Park, Beom-Soo Michael; Lee, Jaehyun; Park, Jongwook

    2015-07-01

    Polymer light-emitting diodes (PLEDs) have attracted much attention from academia and industry field because of their various applications such as large area flat-panel displays and lightings. In this paper, we suggest new blue emitting polymer based on anthracene, Poly(9-(3-Vinyl-phenyl)-anthracene) (PVPA). From NMR data, vinyl group protons were disappeared and aromatic protons showed broad proton peaks because of polymer characteristics. PVPA had film property well and it exhibited vivid PL maximum values of 431, 455, 482 nm and broad PL spectrum. Three dopants for green, red, yellow were used to PVPA, all energy transfer was happened well. By using rubrene dopant of yellow emission, doped film provided white PL.

  16. Crystal structure of bromido-nitro-syl-bis(tri-phenyl-phosphane-κP)nickel(II).

    PubMed

    Hockley, Rose; Irshad, Hira; Sheriff, Tippu S; Motevalli, Majid; Marinakis, Sarantos

    2015-04-01

    The asymmetric unit of the title complex, [NiBr(NO){P(C6H5)3}2], comprises two independent mol-ecules each with a similar configuration. The Ni(II) cation is coordinated by one bromide anion, one nitrosyl anion and two tri-phenyl-phosphane mol-ecules in a distorted BrNP2 tetra-hedral coordination geometry. The coordination of the nitrosyl group is non-linear, the Ni-N-O angles being 150.2 (5) and 151.2 (5)° in the two independent mol-ecules. In the crystal, mol-ecules are linked by weak C-H⋯Br hydrogen bonds and weak C-H⋯π inter-actions into a three-dimensional supra-molecular architecture.

  17. Guanidinium phenyl­arsonate–guanidine–water (1/1/2)

    PubMed Central

    Smith, Graham; Wermuth, Urs D.

    2010-01-01

    In the structure of the title compound, CH6N3 +·C6H6AsO3 −·CH5N3·2H2O, the phenyl­arsonate anion participates in two R 2 2(8) cyclic hydrogen-bonding inter­actions, one with a guanidinium cation, the other with a guanidine mol­ecule. The anions are also bridged by the water mol­ecules, one of which completes a cyclic R 5 3(9) hydrogen-bonding association with the guanidinum cation, conjoint with one of the three R 2 2(8) associations about that ion, as well as forming an R 2 1(6) cyclic association with the guanidine mol­ecule. The result is a three-dimensional framework structure. PMID:21588228

  18. Selective behavioral alterations on addition of a 4'-phenyl group to cocaine.

    PubMed

    Seale, T W; Niekrasz, I; Chang, F; Singh, S; Basmadjian, G P

    1996-01-31

    We synthesized a cocaine analog in which a phenyl group was added at the para-position of the benzene ring of cocaine. This substitution caused a modest reduction (four-fold compared with cocaine) in binding potency for the primate (Papio) dopamine transporter as judged by displacement of [3H]WIN 35,428 binding from caudate/putamen membranes. Behavioral effects of this structural modification in the mouse were complex and selective, comprising absence of stimulation of locomotor activity, enhanced inhibition of locomotion and reduced lethal potency. Convulsant potency was unaltered. Substituents at the 4'-position of cocaine are important in its actions. Simple changes in the chemical structure of this drug may produce complex and selective changes in its neurochemical and behavioral actions.

  19. [The reaction of 3-(R-phenyl)-6-hydrazine pyridazines with substituted isatins (II)].

    PubMed

    Dorneanu, M; Stefănescu, E; Pavelescu, M; Hriscu, A; Alexandrescu, C D; Gherase, F

    1999-01-01

    This paper presents the synthesis of six hydrazones from isatin and 1-morpholinomethyl-isatin and also of their six cooper's complex salts. Their structure was confirmed by the results of the quantitative elemental analysis and by IR, UV-VIS spectral analysis. The biological tests point out that cooper's complex salt of 3-(3'-phenyl-pyridazinylhydrazono)-5-methyl-indoline-2-one (1:2) (VI a) has the smallest toxicity (DMT over 800 mg/kg.w. p.o.), a remarkable anti-inflammatory activity (inhibition 57.1%, IAR 1.1) and also a gastroprotector coefficient of 43.3%. In the mean time, the cooper's complex salt of 3-(3'-p-anisyl-pyridazinyl-hydrazono)-5-methyl-ind oline-2-one (1:2) (VI b) has a gastroprotector coefficient of 76.3% and a lower anti-inflammatory activity than the first derivative (inhibition 36.9%).

  20. Streptomyces koyangensis sp. nov., a novel actinomycete that produces 4-phenyl-3-butenoic acid.

    PubMed

    Lee, Jee Yeon; Lee, Jung Yeop; Jung, Ho Won; Hwang, Byung Kook

    2005-01-01

    A 4-phenyl-3-butenoic acid-producing actinomycete, designated strain VK-A60T, was isolated from a soil sample collected from Koyang, Korea. Morphological and chemical characteristics of the strain were consistent with those of the genus Streptomyces. The cell wall of the strain contains LL-diaminopimelic acid. The predominant fatty acids are anteiso-C(15 : 0), iso-C(16 : 0) and C(16 : 0). The strain formed a distinct monophyletic line within the 16S rRNA gene sequence phylogenetic tree. Analyses of its morphological, physiological and biochemical characteristics, together with random amplified polymorphic DNA and DNA-DNA relatedness data, confirmed that strain VK-A60T represents a novel Streptomyces taxon that is distinguishable from closely related reference strains. Strain VK-A60T (=KCCM 10555T=NBRC 100598T) is proposed as the type strain of a novel species, for which the name Streptomyces koyangensis sp. nov. is proposed.

  1. Living polymerization of (o-(trimethylsilyl)phenyl)acetylene using `small alkoxide` molybdenum(VI) initiators

    SciTech Connect

    Schrock, R.R.; Luo, S.; Zanetti, N.C.; Fox, H.H.

    1994-09-01

    (o-(Trimethylsily)phenyl)acetylene (o-TM-SPA) is polymerized in a living manner by the new `small alkoxide` initiators Mo(CHCMe{sub 2}Ph)(N-1-adamantyl) [OCH(CF{sub 3}){sub 2}]{sub 2}(2,4-lutidine) (1b) and Mo(CHCMe{sub 2}-Ph)(NAr{prime})(OC{sub 6}F{sub 5}){sub 2}(quinulidine) (2; Ar{prime} = 2,6-C{sub 6}H{sub 3}Me{sub 2}) to give low-polydispersity polyenes containing up to 100 equiv of o-TMSPA. The thermodynamically most stable form of poly(o-TMSPA) that contains <25 double bonds is air-sensitive and has a significantly red-shifted {lambda}{sub max}. 29 refs., 1 fig., 1 tab.

  2. 2-(1,3-Benzoxazol-2-ylsulfan-yl)-1-phenyl-ethanone.

    PubMed

    Loghmani-Khouzani, Hossein; Hajiheidari, Dariush; Robinson, Ward T; Abdul Rahman, Noorsaadah; Kia, Reza

    2009-08-29

    In the title compound, C(15)H(11)NO(2)S, a new thio-benzoxazole derivative, the dihedral angle between the benzoxazole ring and the phenyl ring is 9.91 (9)°. An inter-esting feature of the crystal structure is the short C⋯S [3.4858 (17) Å] contact, which is shorter than the sum of the van der Waals radii of these atoms. In the crystal structure, mol-ecules are linked together by zigzag inter-molecular C-H⋯N inter-actions into a column along the a axis. The crystal structure is further stabilized by inter-molecular π-π inter-actions [centroid-centroid = 3.8048 (10) Å].

  3. Solvent and structural effects on the UV absorption spectra of N-(substituted phenyl)-2-cyanoacetamides.

    PubMed

    Matijević, Borko M; Vaštag, Đenđi Đ; Perišić-Janjić, Nada U; Apostolov, Suzana Lj; Milčić, Miloš K; Živanović, Lidija; Marinković, Aleksandar D

    2014-01-03

    UV absorption spectra of N-(substituted phenyl)-2-cyanoacetamides have been recorded in the range 200-400 nm in the set of selected solvents. The solute-solvent interactions were analyzed on the basis of linear solvation energy relationships (LSER) concept proposed by Kamlet and Taft. The effects of substituents on the absorption spectra were interpreted by correlation of absorption frequencies with Hammett substituent constant, σ. It was found that substituents significantly change the extent of conjugation. Furthermore, the experimental findings were interpreted with the aid of ab initio B3LYP/6-311G(d,p) method. Electronic energies was calculated by the use of 6-311++G(3df,3pd) methods with standard polarized continuum model (PCM) for inclusion of the solvent effect.

  4. Glass transition of polystyrene (PS) studied by Raman spectroscopic investigation of its phenyl functional groups

    NASA Astrophysics Data System (ADS)

    Bertoldo Menezes, D.; Reyer, A.; Marletta, A.; Musso, M.

    2017-01-01

    In polymeric materials the glass transition (GT) is a well-known and very important relaxation process related to movements of functional groups in the polymeric chain. In this work, we show the potential of Raman spectroscopy for exploring the GT process in the polymer polystyrene. We collected Raman spectra during a step-by-step heating process of the sample, which allowed us to collect signatures of the GT process from peak parameters of specific vibrational modes, and to verify the GT temperature. Results of the latter were in accordance with published values obtained via other methods. We identified the aromatic ring vibrational modes of the phenyl functional groups to be those which, due to steric hindrance, suffer the largest influence during the GT process. This confirms that Raman spectroscopy can be used as a complementary technique to perform GT investigations in polymeric materials due to its sensitivity to small intermolecular changes affecting vibrational properties of relevant functional side groups.

  5. Non-toxic liquid scintillators with high light output based on phenyl-substituted siloxanes

    NASA Astrophysics Data System (ADS)

    Dalla Palma, M.; Carturan, S. M.; Degerlier, M.; Marchi, T.; Cinausero, M.; Gramegna, F.; Quaranta, A.

    2015-04-01

    The work describes the development of a new class of liquid scintillators based on polysiloxane liquid compounds. These materials are characterized by low toxicity, chemical inertness, very low volatility and low flammability, allowing their use without concerns even at high temperatures in vacuum. In this view different polysiloxane based liquids have been tested, with variable content and distribution of phenyl lateral substituents and added with suitable dyes, namely 2,5-diphenyloxazole (PPO) and Lumogen Violet (LV). Absorption and fluorescence spectroscopy have been used in order to study the emission feature of the various compounds and to investigate the spectral matching between siloxane solvents and dissolved primary dyes. Scintillation efficiency towards 60Co and 137Cs gamma rays, relative to commercial liquid scintillator (EJ-309), has been measured and the results have been related to the energy transfer and energy migration mechanism from monomer and excimer forming sites in liquid siloxanes.

  6. Theoretical study of the decomposition of ethyl and ethyl 3-phenyl glycidate.

    PubMed

    Josa, Daniela; Peña-Gallego, Angeles; Rodríguez-Otero, Jesús; Cabaleiro-Lago, Enrique M

    2013-01-01

    The mechanism of the decomposition of ethyl and ethyl 3-phenyl glycidate in gas phase was studied by density functional theory (DFT) and MP2 methods. A proposed mechanism for the reaction indicates that the ethyl side of the ester is eliminated as ethylene through a concerted six-membered cyclic transition state, and the unstable intermediate glycidic acid decarboxylates rapidly to give the corresponding aldehyde. Two possible pathways for glycidic acid decarboxylation were studied: one via a five-membered cyclic transition state, and the other via a four-membered cyclic transition state. The results of the calculations indicate that the decarboxylation reaction occurs via a mechanism with five-membered cyclic transition state.

  7. On the reactions of cyclohexyl phenyl sulfide with water by means of density functional theory

    NASA Astrophysics Data System (ADS)

    Lysogorskiy, Yu. V.; Aminova, R. M.; Tayurskii, D. A.

    2015-12-01

    The production of heavy oil is increasing in coming years due to short fall of conventional light crude. However, extremely high viscosity and abundant amount of heteroatoms (S, O and N) in the structure of heavy oil molecules are one of the main challenges in their exploitation, transportation and processing. Aquathermolysis are often proposed as a method to reduce the viscosity and improve the rheological properties of heavy oils. Aquathermolysis is a reaction of heated water with hydrocarbons molecules in the absence of oxygen. In the present work we have considered different reactions of cyclohexyl phenyl sulfide molecule with water as a very particular model for aquathermolysis process by means of density functional methods. Obtained tendencies in reaction pathways are coherent with previous experimental results. Thus, ab initio methods demonstrated applicability for comparative studies of chemical reaction pathways in aquathermolysis and could be used for the further screening of possible catalysts for this process.

  8. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). 721.10130 Section 721.10130 Protection of...-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). (a) Chemical substance and...-7,14-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (PMN P-07-140) is subject...

  9. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). 721.10130 Section 721.10130 Protection of...-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). (a) Chemical substance and...-7,14-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (PMN P-07-140) is subject...

  10. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). 721.10130 Section 721.10130 Protection of...-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). (a) Chemical substance and...-7,14-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (PMN P-07-140) is subject...

  11. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). 721.10130 Section 721.10130 Protection of...-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). (a) Chemical substance and...-7,14-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (PMN P-07-140) is subject...

  12. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). 721.10130 Section 721.10130 Protection of...-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (generic). (a) Chemical substance and...-7,14-dione, 5,12-dihydro-ar- substituted]phenyl]-, monosodium salt (PMN P-07-140) is subject...

  13. (S) 2-phenyl-2-(p-tolylsulfonylamino)acetic acid. Structure, acidity and its alkali carboxylates

    NASA Astrophysics Data System (ADS)

    Duarte-Hernández, Angélica M.; Contreras, Rosalinda; Suárez-Moreno, Galdina V.; Montes-Tolentino, Pedro; Ramos-García, Iris; González, Felipe J.; Flores-Parra, Angelina

    2015-03-01

    The structure and the preferred conformers of (S) 2-phenyl-2-(p-tolylsulfonylamino)acetic acid (1) are reported. Compound 1 is a derivative of the unnatural aminoacid the (S) phenyl glycine. The X-ray diffraction analyses of the complexes of 1 with water, methanol, pyridine and its own anion are discussed. In order to add information about the acidity of the COOH and NH protons in compound 1, its pKa in DMSO and those of N-benzyl-p-tolylsulfonamide and (S) N-methylbenzyl-p-tolylsulfonamide were determined by cyclic voltammetry. Data improved the scarce information about pKa in DMSO values of sulfonamides. The products of the reactions of compound 1 with one and two equivalents of LiOH, NaOH and KOH in methanol were analyzed. Crystals of the lithium (2) and sodium (3) carboxylates and the dipotassium sulfonylamide acetate (7) were obtained, they are coordination polymers. In compound 2, the lithium is bound to four oxygen atoms with short bond lengths. The coordination of the lithium atom to two carboxylates gives an infinite ribbon by formation of fused six membered rings. In the crystal of compound 3, two pentacoordinated sodium atoms are bridged by three oxygen atoms, one from a water molecule and two from DMSO. The short distance between the sodium atoms (3.123 Å), implies a metal-metal interaction. The sodium couples are linked by two carboxylate groups, forming a planar ribbon of fused twelve membered rings. A notable discovery was a water molecule quenched in the middle of the ring, with a tetra coordinated oxygen atom in a square planar geometry. In compound 7, the carboxylate and the amide are bound to heptacoordinated potassium atoms. The 2D polymer of 7 has a sandwich structure, with the carboxylate and potassium atoms in the inner layer covered by the aromatic rings.

  14. Kinetic analysis of the pyrolysis of phenethyl phenyl ether: computational prediction of ?/?-selectivities

    SciTech Connect

    Beste, Ariana; Buchanan III, A C; Britt, Phillip F; Hathorn, Bryan C; Harrison, Robert J

    2007-01-01

    We have developed a scheme to predict / -product selectivities in the pyrolysis of model compounds for the -ether linkage in lignin. The calculation of the individual / -selectivities for hydrogen abstraction by chain carrying benzyl and phenoxyl radicals profits from error cancellation in the computation of relative rate constants of similar reactions with common reactants. The Arrhenius pre-factors depend strongly on the description of the low-frequency modes for which anharmonic contributions are important. We use density functional theory in combination with transition state theory in this analysis. Diagonal anharmonic effects for individual low-frequency modes are included by employing a second-order Wigner-Kirkwood expansion in a semiclassical expression for the vibrational partition function. The composite / -product selectivity is obtained by applying quasi-steady-state kinetic analysis for the intermediate radicals. We calculate an overall / -selectivity for the pyrolysis of phenethyl phenyl ether as a composite of the / -selectivities in the hydrogen abstraction reactions by the phenoxyl and by the benzyl radical that is in excellent agreement with experiment. The difference between the individual selectivities for these radicals is explained by analyzing the electronic structure of the transition states. Spin delocalization of the single electron favors the -pathways. An opposing effect occurs for polarized transition states, such as the transition states for the hydrogen abstraction by the electrophilic phenoxyl radical, where the adjacent ether oxygen in phenethyl phenyl ether stabilizes the -transition states. These results also indicate that theory will be able to provide excellent predictions of / -product selectivities for more complicated lignin model compounds bearing multiple substituents.

  15. Enkephalin analogues with N-phenyl-N-(piperidin-2-ylmethyl) propionamide derivatives: Synthesis and biological evaluations

    PubMed Central

    Deekonda, Srinivas; Cole, Jacob; Sunna, Sydney; Rankin, David; Largent-Milnes, Tally M.; Davis, Peg; BassiriRad, Neemah M.; Lai, Josephine; Vanderah, Todd W.; Porecca, Frank; Hruby, Victor J.

    2016-01-01

    N-Phenyl-N-(piperidin-2-ylmethyl)propionamide based bivalent ligands are unexplored for the design of opioid based ligands. Two series of hybrid molecules bearing N-phenyl-N-(piperidin-2-ylmethyl)propionamide derived small molecules conjugated with an enkephalin analogues with and without a linker (β-alanine) were designed and synthesized. Both bivalent ligand series exhibited remarkable binding affinities from nanomolar to subnanomolar range at both μ and δ opioid receptors and displayed potent agonist activities as well. The replacement of Tyr with Dmt and introduction of a linker between the small molecule and enkephalin analogue resulted in highly potent ligands. Both series of ligands showed excellent binding affinities at both μ (0.6–0.9 nM) and δ (0.2–1.2 nM) opioid receptors respectively. Similarly, these bivalent ligands exhibited potent agonist activities in both MVD and GPI assays. Ligand 17 was evaluated for in vivo antinociceptive activity in non-injured rats following spinal administration. Ligand 17 was not significantly effective in alleviating acute pain. The most likely explanations for this low intrinsic efficacy in vivo despite high in vitro binding affinity, moderate in vitro activity are (i) low potency suggesting that higher doses are needed; (ii) differences in experimental design (i.e. non-neuronal, high receptor density for in vitro preparations versus CNS site of action in vitro); (iii) pharmacodynamics (i.e. engaging signalling pathways); (iv) pharmacokinetics (i.e. metabolic stability). In summary, our data suggest that further optimisation of this compound 17 is required to enhance intrinsic antinociceptive efficacy. PMID:26611918

  16. Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity.

    PubMed

    Maggio, Benedetta; Raimondi, Maria Valeria; Raffa, Demetrio; Plescia, Fabiana; Cascioferro, Stella; Plescia, Salvatore; Tolomeo, Manlio; Di Cristina, Antonietta; Pipitone, Rosaria Maria; Grimaudo, Stefania; Daidone, Giuseppe

    2011-01-01

    Several new N-phenyl-1H-indazole-1-carboxamides 1c-h and 4l,m were prepared by reacting phenyl isocyanate derivatives 3a,b with 3-amino-1H-indazole derivatives 2c,e,g or 1H-indazole 2l respectively. Chemical transformations of compounds 1a,b and 1g,h gave 3-acetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 5a,b, and 3,5-diamino-N-phenyl-1H-indazole-1-carboxamide derivatives 4i,j respectively. Finally, 3,5-diacetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 6a,b were prepared by acetylation of 4i,j. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell lines panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). Compound 1c, the most active of the series, was able to inhibit cell growth showing GI(50) values in the 0.041-33.6 μM range, mean GI(50) 1.90 μM, being very effective against colon and melanoma cell lines. Cell cycle analysis in K562 cells showed that 1c causes a marked increase of cells in G0-G1 phase. Moreover, it increases the ratio between hypophosphorylated pRb and total pRb.

  17. A VUV photoionization study of the multichannel reaction of phenyl radicals with 1,3-butadiene under combustion relevant conditions.

    PubMed

    Golan, Amir; Ahmed, Musahid; Mebel, Alexander M; Kaiser, Ralf I

    2013-01-07

    We studied the reaction of phenyl radicals (C(6)H(5)) with 1,3-butadiene (H(2)CCHCHCH(2)) exploiting a high temperature chemical reactor under combustion-like conditions (300 Torr, 873 K). The reaction products were probed in a supersonic beam by utilizing VUV radiation from the Advanced Light Source and by recording the experimental PIE curves at mass-to-charge ratios of m/z = 130 (C(10)H(10)(+)), 116 (C(9)H(8)(+)), and 104 (C(8)H(8)(+)). Our data suggest that the atomic hydrogen (H), methyl (CH(3)), and vinyl (C(2)H(3)) losses are open with estimated branching ratios of about 86 ± 4%, 8 ± 2%, and 6 ± 2%, respectively. The isomer distributions were probed further by fitting the experimentally recorded PIE curves with a linear combination of the PIE curves of individual C(10)H(10), C(9)H(8), and C(8)H(8) isomers. These fits indicate the formation of three C(10)H(10) isomers (trans-1,3-butadienylbenzene, 1,4-dihydronaphthalene, 1-methylindene), three C(9)H(8) isomers (indene, phenylallene, 1-phenyl-1-methylacetylene), and a C(8)H(8) isomer (styrene). A comparison with results from recent crossed molecular beam studies of the 1,3-butadiene-phenyl radical reaction and electronic structure calculations suggests that trans-1,3-butadienylbenzene (130 amu), 1,4-dihydronaphthalene (130 amu), and styrene (104 amu) are reaction products formed as a consequence of a bimolecular reaction between the phenyl radical and 1,3-butadiene. 1-Methylindene (130 amu), indene (116 amu), phenylallene (116 amu), and 1-phenyl-1-methylacetylene (116 amu) are synthesized upon reaction of the phenyl radical with three C(4)H(6) isomers: 1,2-butadiene (H(2)CCCH(CH(3))), 1-butyne (HCCC(2)H(5)), and 2-butyne (CH(3)CCCH(3)); these C(4)H(6) isomers can be formed from 1,3-butadiene via hydrogen atom assisted isomerization reactions or via thermal rearrangements of 1,3-butadiene involving hydrogen shifts in the high temperature chemical reactor.

  18. Twisting the Phenyls in Aryl Diphosphenes (Ar-P=P-Ar). Significant Impact upon Lowest Energy Excited States

    PubMed Central

    Peng, Huo-Lei; Payton, John L.; Protasiewicz, John D.

    2009-01-01

    Aryl diphosphenes (Ar-P=P-Ar) possess features that may make them useful in photonic devices, including the possibility for photochemical E-Z isomerization. Development of good models guided by computations is hampered by poor correspondence between predicted and experimental UV/vis absorption spectra. An hypothesis that the phenyl twist angle (i.e. PPCC torsion) accounts for this discrepancy is explored, with positive findings. DFT and TDDFT (B3LYP) were applied to the phenyl-P=P-phenyl (Ph-P=P-Ph) model compound over a range of phenyl twist angles, and to the Ph-P=P-Ph cores of two crystallographically characterized diphosphenes: bis-(2,4,6-tBu3C6H2)-diphosphene (Mes*-P=P-Mes*) and bis-(2,6-Mes2C6H3)-diphosphene (Dmp-P=P-Dmp). A shallow PES is observed: the full range of phenyl twist angles is accessible for under 5 kcal/mol. The Kohn-Sham orbitals (KS-MOs) exhibit stabilization and mixing of the two highest energy frontier orbitals – the n+ and π localized primarily on the – P=P– unit. A simple, single-configuration model based upon this symmetry-breaking is shown to be consistent with the major features of the measured UV/vis spectra of several diphosphenes. Detailed evaluation of singlet excitations, transition energies and oscillator strengths with TDDFT showed that the lowest energy transition (S1 ← S0) does not always correspond to the LUMO ← HOMO configuration. Coupling between the phenyl rings and central –P=P– destabilizes the π-π* dominated state. Hence, the S1 is always n+-π* in nature, even with a π-type HOMO. This coupling of the ring and –P=P– π systems engenders complexity in the UV/vis absorption region, and may be the origin of the variety of photobehaviours observed in diphosphenes. PMID:19496568

  19. Nanomolar and selective determination of epinephrine in the presence of norepinephrine using carbon paste electrode modified with carbon nanotubes and novel 2-(4-oxo-3-phenyl-3,4-dihydro-quinazolinyl)-N'-phenyl-hydrazinecarbothioamide.

    PubMed

    Beitollahi, Hadi; Karimi-Maleh, Hassan; Khabazzadeh, Hojatollah

    2008-12-15

    A novel modified carbon nanotube paste electrode of 2-(4-oxo-3-phenyl-3,4-dihydro-quinazolinyl)-N'-phenyl-hydrazinecarbothioamide (2PHC) was fabricated, and the electro-oxidation of epinephrine (EP), norepinephrine (NE), and their mixture has been studied using electrochemical methods. The modified electrode displayed strong catalytic function for the oxidation of EP and NE and resolved the overlap voltammetric response of EP and NE into two well-defined voltammetric peaks of about 240 mV with square wave voltammetry (SWV). A linear response in the range of (5 x 10(-8))-(5.5 x 10(-4)) M with a detection limit (S/N = 3) of 9.4 nM for EP was obtained.

  20. Facile, regioselective [4 + 2] cycloaddition involving 1-aryl-4-phenyl-1-azadienes and allenic esters: an efficient route to novel substituted 1-aryl-4-phenyl-1,4-dihydropyridines.

    PubMed

    Ishar, M P; Kumar, K; Kaur, S; Kumar, S; Girdhar, N K; Sachar, S; Marwaha, A; Kapoor, A

    2001-07-12

    [reaction: see text]1-Aryl-4-phenyl-1-azadienes undergo facile, regioselective [4 + 2] cycloaddition to the C2,C3 pi-bond of allenic esters in refluxing benzene, and the formed adducts undergo a 1,3-H shift to afford novel 2-alkyl-1-aryl-3-ethoxycarbonyl-4-phenyl-1,4-dihydropyridines (78-97%). However, when the reaction is carried at room temperature, besides the [4 + 2] addition, the [2 + 2] mode of addition involving C=N of azadiene and C3,C4 pi-bond of allenic esters also intervenes. The resulting N-aryl-2-ethoxy-carbonyl-methylidene-4-styrylazetidines (17-28%) undergo reorganization on silica gel to afford 2-cyclohexen-1-ones.

  1. Regioselective synthesis of novel 3-allyl-2-(substituted imino)-4-phenyl-3H-thiazole and 2,2‧-(1,3-phenylene)bis(3-substituted-2-imino-4-phenyl-3H-thiazole) derivatives as antibacterial agents

    NASA Astrophysics Data System (ADS)

    Abbasi Shiran, Jafar; Yahyazadeh, Asieh; Mamaghani, Manouchehr; Rassa, Mehdi

    2013-05-01

    Several novel 3-allyl-2-(substituted imino)-4-phenyl-3H-thiazole derivatives were synthesized by the reaction of allyl-thioureas and 2-bromoacetophenone. We also report the synthesis of bis-allyl-3H thiazoles using the reaction of various isothiocyanates and 1,3-phenylenediamine. The structures of all compounds were characterized by spectral and elemental analysis. Most of the synthesized compounds exhibited efficient antibacterial activities against Salmonella enterica, Micrococcus luteus, Bacillus subtilis and Pseudomonas aeruginosa.

  2. (1′S,2R,3R)-(−)-2-Hydr­oxy-3-morpholino-3-phenyl-N-(1′-phenyl­ethyl)propion­amide

    PubMed Central

    Mendoza, Angel; Aparicio, David M.; Terán, Joel L.; Gnecco, Dino; Juárez, Jorge R.

    2009-01-01

    In the title compound, C21H26N2O3, the morpholine ring has a chair conformation and the dihedral angle between the two phenyl rings is 59.0 (3)°. The crystal packing is stabilized by inter­molecular O—H⋯O hydrogen bonds, generating a ribbon structure along the a axis. An intra­molecular N—H⋯O contact is also present. PMID:21582476

  3. Crystal thickness dependence of the photoinduced crystal bending of 1-(5-methyl-2-(4-(p-vinylbenzoyloxymethyl)phenyl)-4-thiazolyl)-2-(5-methyl-2-phenyl-4-thiazolyl)perfluorocyclopentene.

    PubMed

    Kitagawa, Daichi; Kobatake, Seiya

    2014-05-01

    Rod-like crystals of 1-(5-methyl-2-(4-(p-vinylbenzoyloxymethyl)phenyl)-4-thiazolyl)-2-(5-methyl-2-phenyl-4-thiazolyl)perfluorocyclopentene with lengths of over 1 mm showed photoreversible bending over 100 cycles upon irradiation with alternating ultraviolet (UV) and visible light. The crystals bent toward the incident light due to a contraction of the crystal length and a gradient of the crystal thickness, which depend on the extent of photoisomerization. It was observed that the bending speed depends on the crystal thickness, and the curvature change on changing the crystal thickness agrees well with Timoshenko's bimetal model, as well as with the observation that crystals of 1,2-bis(2-methyl-5-(4-(1-naphthoyloxymethyl)phenyl)-3-thienyl)perfluorocyclopentene bend away from the incident light due to an expansion of the crystal length and a gradient of the crystal thickness, which depend on the extent of photoisomerization. It was revealed that Timoshenko's bimetal model can be applied to photoinduced crystal bending behaviors caused by both contraction and expansion. These findings are very useful for evaluating and designing photomechanical actuators.

  4. Synthesis and X-ray structural studies of Cd(II) and Ni(II) complexes of 5-(4-methoxy phenyl), 5-(2-pyridyl) and 5-(2-methoxy phenyl)-1,3,4-oxadiazole-2-thione

    NASA Astrophysics Data System (ADS)

    Bharty, M. K.; Bharti, A.; Dani, R. K.; Dulare, R.; Bharati, P.; Singh, N. K.

    2012-03-01

    Three new mixed ligand complexes [Cd(en)2(4-mpot)2] (1) [Ni(2-pytone)2(en)2] (2) and [Ni(2-mpot)2(en)2] (3) {4-mpot = 5-(4-methoxy-phenyl)-1,3,4-oxadiazole-2-thione, 2-pytone = 5-(2-pyridyl)-1,3,4-oxadiazole-2-thione, 2-mpot = 5-(2-methoxy-phenyl)-1,3,4-oxadiazole-2-thione} have been prepared containing en as co-ligand. Potassium N-(4-methoxy benzoyl)-hydrazinecarbodithioate cyclized to 5-(4-methoxy-phenyl)-1,3,4-oxadiazole-2-thiol on addition of tetrabutylammonium bromide which then reacted with Cd(OAc)2·2H2O and ethylenediamine to form complex 1, whereas potassium N-(2-methoxy benzoyl/pyridine-2-carbonyl)-hydrazinecarbodithioates (RCONHNHCSSK) underwent cyclization during complexation in the presence of en to give the complexes of the corresponding 5-aryl-1,3,4-oxadiazole-2-thiones. The complexes have been characterized by physicochemical techniques and single crystal X-ray structure determination. In the complexes the metal center has a six coordinate octahedral arrangement coordinated by 4N atoms of two en and two covalently bonded N atoms of the oxadiazole-2-thione anions. All the complexes contain extended hydrogen bonding providing supramolecular framework.

  5. Diphen­yl[(phenyl­sulfan­yl)meth­yl]-λ5-phosphane­thione

    PubMed Central

    Gessner, Viktoria H.

    2014-01-01

    The title compound, C19H17PS2, results from the direct deprotonation of di­phenyl­methyl­phosphine sulfide and subsequent reaction with diphenyl di­sulfide. The C—P and C—S bond lengths of 1.8242 (18) and 1.8009 (18) Å, respectively, of the central P—C—S linkage are comparable to those found in the sulfonyl analogue, but are considerably longer than those reported for the dimetallated sulfonyl compound. The dihedral angle between the benzene rings of the di­phenyl­methyl moiety is 69.46 (7)°. No distinct inter­molecular inter­actions are present in the crystal structure. PMID:24765055

  6. Benzyl 5-phenyl­pyrazolo­[5,1-a]isoquino­line-1-carboxyl­ate

    PubMed Central

    Lu, Yu-Kun; Yao, Xiao; Luo, Li-Wen; Lü, Ren-Qing; Liu, Yun-Qi

    2011-01-01

    In the title compound, C25H18N2O2, the pyrazolo­[5,1-a]iso­quin­oline ring system is approximately planar [maximum deviation = 0.027 (2) Å] and is oriented at dihedral angles of 57.22 (6) and 71.36 (7)° with respect to the two phenyl rings. The phenyl rings are twisted to each other by a dihedral angle of 66.33 (8)°. A weak intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, weak C—H⋯π inter­actions are present. PMID:22199960

  7. New Poly(amide-imide)/Nanocomposites Reinforced Silicate Nanoparticles Based on N-pyromellitimido-L-phenyl Alanine Containing Ether Moieties

    NASA Astrophysics Data System (ADS)

    Faghihi, Khalil; Shabanian, Meisam; Dadfar, Ehsan

    2012-02-01

    A series of Poly(amide-imide)/montmorillonite nanocomposites containing N-pyromellitimido-L-phenyl alanine moiety in the main chain were synthesized by a convenient solution intercalation technique. Poly(amide-imide) (PAI) 5 as a source of polymer matrix was synthesized by the direct polycondensation reaction of N-pyromellitimido-L-phenyl alanine 3 with 4,4'-diamino diphenyl ether 4 in the presence of triphenyl phosphite (TPP), CaCl2, pyridine and N-methyl-2-pyrrolidone (NMP). The resulting nanocomposite films were characterized by Fourier transform infrared spectra (FT-IR), X-ray diffraction (XRD), scanning electron microscopy (SEM) and thermogravimetric analysis (TGA). The results showed that organo-modified clay was dispersed homogeneously in PAI matrix. TGA indicated an enhancement of thermal stability of new nanocomposites compared with the pure polymer.

  8. 2-(4-Chloro­phen­yl)-4-phenyl-1,2-di­hydro­quinazoline

    PubMed Central

    Derabli, Chamseddine; Boulcina, Raouf; Bouacida, Sofiane; Merazig, Hocine; Debache, Abdelmadjid

    2013-01-01

    In the title compound, C20H15ClN2, the pyrimidine ring is in a flattened half-chair conformation. The phenyl and chloro-substituted benzene rings form dihedral angles of 84.97 (5) and 80.23 (4)°, respectively, with the benzene ring of the di­hydro­quinazoline group. The dihedral angle between the phenyl and chloro-substituted benzene rings is 61.71 (5)°. In the crystal, mol­ecules are arranged in inter­secting layers parallel to (101) and (-102), with N—H⋯N hydrogen bonds linking mol­ecules along [010]. In addition, a weak C—H⋯π inter­action is observed. PMID:24454093

  9. Crystal structure of 1-mesityl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium iodide

    PubMed Central

    Canseco-González, Daniel; García, Juventino J.; Flores-Alamo, Marcos

    2015-01-01

    In the cation of the title salt, C18H20N3 +·I−, the mesityl and phenyl rings are inclined to the central triazolium ring by 61.39 (16) and 30.99 (16)°, respectively, and to one another by 37.75 (15)°. In the crystal, mol­ecules are linked via C—H⋯I hydrogen bonds, forming slabs parallel to the ab plane. Within the slabs there are weak π–π inter­actions present involving the mesityl and phenyl rings [inter-centroid distances are 3.8663 (18) and 3.8141 (18) Å]. PMID:26870488

  10. Design, synthesis and pharmacophoric model building of new 3-alkoxymethyl/3-phenyl indole-2-carboxamides with potential antiproliferative activity.

    PubMed

    Abdelrahman, Mostafa H; Aboraia, Ahmed S; Youssif, Bahaa G M; Elsadek, Bakheet E M

    2016-12-26

    Novel 3-alkoxymethyl/3-phenyl indole-2-carboxamide derivatives were synthesized and evaluated for their anticancer activity. Most of the tested compounds showed moderate to excellent activity against the tested cell lines (MCF7 and HCT116). 3-Phenyl substitution on indole with p-piperidinyl phenethyl 24a and p-dimethylamino phenethyl 24c exhibited anticancer activity against MCF7 with IC50 of 0.13 and 0.14 μm, respectively. Further mechanistic study of the most active compounds through their action on cell cycle showed disturbance in cell cycle progression and cell cycle arrest. For future development of this series of compounds, pharmacophore study was conducted which indicated that the enhancement of the activity could be achieved through the addition of acceptor or donating groups to the already-present indole nucleus.

  11. Effects of paraoxon, p-nitrophenol, phenyl saligenin cyclic phosphate, and phenol on the rat interleukin 2 system.

    PubMed

    Pruett, S B; Chambers, J E

    1988-01-01

    Two organophosphorus compounds, paraoxon and phenyl saligenin cyclic phosphate, as well as p-nitrophenol and phenol which are structurally related to paraoxon, were tested for their effects on interleukin 2 (IL2) production and responsiveness by rat splenocytes in vitro. Three of the four compounds inhibited mitogen-induced lymphocyte proliferation as well as IL2 production and responsiveness. However, phenyl saligenin cyclic phosphate produced maximal inhibition at a much lower concentration (0.5 microM) than p-nitrophenol (200 microM) or paraoxon (200 microM). Phenol was not inhibitory at any concentration tested (up to 250 microM). Since the production of and response to IL2 are key events in immune responses, compounds which suppress these events can be identified as potential suppressors of host resistance to disease.

  12. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine inhibits proton motive force in energized liver mitochondria

    SciTech Connect

    Singh, Y.; Bhatnagar, R.; Sidhu, G.S.; Batra, J.K.; Krishna, G. )

    1989-05-15

    It is known that 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), which induces Parkinson's-like disease in primates and humans, depletes hepatocytes of ATP and subsequently causes cell death. Incubation of rat liver mitochondria with MPTP and 1-methyl-4-phenyl pyridinium ion (MPP+) significantly inhibited incorporation of {sup 32}Pi into ATP. MPTP and MPP+ inhibited the development of membrane potential and pH gradient in energized rat liver mitochondria, suggesting that reduction of the proton motive force may have reduced ATP synthesis. Since deprenyl, an inhibitor of monoamine oxidase, prevented the formation of MPP+ and inhibited the decrease in membrane potential caused by MPTP, but not that caused by MPP+, these effects of MPTP, as well as cell death, probably were mediated by MPP+. This mechanism may play a role in the specific loss of dopaminergic neurons resulting in MPTP-induced Parkinson's disease.

  13. 2-Carbaborane-3-phenyl-1H-indoles – Synthesis via McMurry Reaction and COX Inhibition Activity

    PubMed Central

    Neumann, Wilma; Scholz, Matthias; Lönnecke, Peter; Crews, Brenda; Marnett, Lawrence J.; Pietzsch, Jens; Kniess, Torsten

    2013-01-01

    Cyclooxygenase-2 (COX-2) inhibitors have been in the focus of medicinal chemistry for years and many compounds exhibiting high selectivity and affinity were developed. As carbaboranes represent interesting pharmacophores as phenyl mimetics in drug development, this paper presents the synthesis of carbaboranyl derivatives of COX-2-selective 2,3-disubstituted indoles. Despite the lability of carbaboranes under reducing conditions, 2-carbaborane-3-phenyl-1H-indoles could be synthesized by McMurry cyclization of the corresponding amides. While the meta-carbaboranyl-substituted derivatives (3a-c) lacked COX inhibition activity, the ortho-carbaboranyl analog (3d) was active but showed a selectivity shift towards COX-1. PMID:23303738

  14. Oxa-ene reaction of enols of amides with 4-phenyl-1,2,4-triazoline-3,5-dione.

    PubMed

    Basheer, Ahmad; Rappoport, Zvi

    2008-01-04

    The reaction of 16 enols of amides with 4-phenyl-1,2,4-triazoline-1,3-dione gave open chain adducts rather than the [2 + 2] cycloadducts with a hemiaminal moiety, both in solid state and in solution. This assignment is based on X-ray crystallography, (1)H and (13)C NMR data, and IR spectra. The suggested mechanism involves hydroxyl proton loss in a formal oxa-ene reaction. Mechanistic details and a possible alternative are discussed.

  15. 2-Phenyl-2,3-dihydro­phenanthro[9,10-b][1,4]dioxine

    PubMed Central

    Fun, Hoong-Kun; Quah, Ching Kheng; Wu, Dongdong; Zhang, Yan

    2011-01-01

    In the title compound, C22H16O2, the phenanthrene ring system is essentially planar [maximum deviation = 0.058 (1) Å] and is inclined at an angle of 58.39 (6)° to the phenyl ring. The 1,4-dioxane ring is in a chair conformation. In the crystal, mol­ecules are stacked along the b axis, but no significant hydrogen bonds are observed. PMID:21522334

  16. 2-[(E)-(2-Phenyl-2H-1,2,3-triazol-4-yl)methyl-eneamino]ethanol.

    PubMed

    Dang, Yan-Qiu; Tian, Lai-Jin

    2009-03-11

    In the title Schiff base compound, C(11)H(12)N(4)O, the mol-ecule adopts a trans configuration about the central C=N bond. The dihedral angle between the phenyl ring and the triazole ring is 14.3 (3)°. In the crystal structure, mol-ecules are linked into a one-dimensional supra-molecular chain by inter-molecular O-H⋯N hydrogen bonding between the hydroxyl group and the imino N atom.

  17. 3,3'-Di-n-propyl-1,1'-[p-phenyl-enebis(methyl-ene)]diimidazolium dibromide.

    PubMed

    Haque, Rosenani A; Nasri, S Fatimah; Hemamalini, Madhukar; Fun, Hoong-Kun

    2011-08-01

    The asymmetric unit of the title compound, C(20)H(28)N(4) (2+)·2Br(-), consists of half a 3,3'-di-n-propyl-1,1'-[p-phenyl-enenis(methyl-ene)]diimidazolium cation and a bromide anion. The cation is located on an inversion center and adopts an ⋯AAA⋯ trans conformation. In the crystal, the cation is linked to the anions via weak C-H⋯Br hydrogen bonds.

  18. High-temperature polyimides prepared from 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane

    NASA Technical Reports Server (NTRS)

    Jones, Robert J. (Inventor); Chang, Glenn E. C. (Inventor)

    1984-01-01

    There are provided the aromatic diamines 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane, where the attached ortho halogen is preferably chlorine, and 4,4'-bis(4-aminophenoxy)biphenyl, as novel monomers for polyimide polymerizations. The former, when reacted with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, provides a polyimide having exceptional high-temperature performance. The latter diamine is a low-cost monomer for polyimide production.

  19. Crystal structure of 1-acetyl-3-(4-methylphenyl)-5-phenyl-4,5-dihydro-1 H-pyrazole

    NASA Astrophysics Data System (ADS)

    Bülbül, H.; Tinmaz, F.; Dege, N.; Özer İlhan, İ.; Sarıpınar, E.

    2014-12-01

    In the title compound, C18H18N2O, the whole molecule is not planar but the phenyl ring systems are planar individually. The central pyrazole ring system is twisted with puckering parameters Q = 0.1610(18) Å and φ = 82.2(6)°. The crystallographic structure is stabilized by C-H⋯N type intramolecular hydrogen bond, generating ring motif R(5).

  20. BF3·Et2O Catalysed 4-Aryl-3-phenyl-benzopyrones, Pro-SERMs, and Their Characterization

    PubMed Central

    Srivastava, Ambika; Singh, Pooja; Kumar, Rajesh

    2015-01-01

    We have synthesized the novel 4-(4-hydroxy-benzyl)-3-phenyl-chromen-2-one which is a precursor of SERMs with a smaller number of steps and good yield. Two methodologies for the synthesis have been worked out. Anhydrous BF3·Et2O catalyzed reaction was found to be selective for product formation while anhydrous AlCl3, FeCl3, and SnCl4 catalyzed ones were nonselective. PMID:26421007

  1. The effect of phenyl mercury on reproductive performance in laying hens.

    PubMed

    Pribilincová, J; Marettová, E; Kosucký, J; Maretta, M

    1996-01-01

    The effect of phenyl mercury with and without selenium on the egg production of laying hens and on the fertility, hatchability and properties of eggs was studied. Mercury was administered via the feed at dosages of 5 ppm, 30 ppm, and 30 ppm Hg + 4 ppm Se, for 56 days. After two months, egg production decreased by 8.18% and 7.74% in hens fed 30 ppm Hg, and 30 ppm Hg + 4 ppm Se, respectively. Egg weight decreased in all experimental groups. In comparison to the controls, these results were highly significant (P < 0.01) in hens fed 30 ppm Hg and 30 ppm Hg + 4 ppm Se and significant (P < 0.05) between hens fed 5 ppm Hg and 30 ppm Hg. Fertility rate and hatchability were not affected. Mercury exposure did not affect egg shape, egg-white height, egg-shell hardness or yolk colour. Both egg-shell thickness and weight decreased in all experimental groups. In the group supplemented with selenium there was a nonsignificant improvement in egg production, hatchability and all qualitative properties of eggs in comparison with the group without selenium supplementation. Residual mercury levels in egg yolk greatly surpassed the level found in the egg white: the highest values were measured in the group fed 30 ppm Hg. The addition of selenium had a protective effect upon residual Hg deposits in the yolk, but not in the egg-white.

  2. Click functionalization of phenyl-capped bithiophene on azide-terminated self-assembled monolayers

    NASA Astrophysics Data System (ADS)

    Zheng, Yijun; Cui, Jiaxi; Ikeda, Taichi

    2015-11-01

    We immobilized tetra(ethylene glycol)-substituted phenyl-capped bithiophene with alkyne terminals (Ph2TPh-alkyne) on azide-terminated self-assembled monolayers (N3-SAMs) by Cu-catalyzed azide-alkyne cycloaddition reaction. Ph2TPh-functionalized SAMs on a gold substrate showed reversible electrochemical response. The surface densities of the azide groups in N3-SAMs and Ph2TPh units in Ph2TPh-functionalized SAMs were estimated to be 7.3 ± 0.3 × 10-10 mol cm-2 and 4.6 ± 0.3 × 10-10 mol cm-2, respectively, by quartz crystal microbalance (QCM). Most of Ph2TPh-alkynes are considered to be anchored on N3-SAMs via both terminal groups. Ph2TPh-functionalized SAMs exhibited reversible redox peaks in cyclic voltammetry (CV). In redox reaction, reversible capture and release of the counter anion could be monitored by electrochemical QCM (E-QCM).

  3. (η(6)-Benzene)-dichlorido(dicyclo-hexyl-phenyl-phosphane)ruthenium(II) benzene sesquisolvate.

    PubMed

    Muller, Alfred; Davis, Wade L

    2012-12-01

    The asymmetric unit of the title compound, [RuCl2(C6H6)(C18H27P)]·1.5C6H6, contains one mol-ecule of the Ru(II) complex and one and a half solvent molecules as one of these is located about a centre of inversion. The Ru(II) atom has a classical three-legged piano-stool environment being coordinated by an η(6)-benzene ligand [Ru-centroid = 1.6964 (6) Å], two chloride ligands with an average Ru-Cl bond length of 2.4138 (3) Å and a dicyclo-hexyl-phenyl-phosphane ligand [Ru-P = 2.3786 (3) Å]. The effective cone angle for the phosphane was calculated to be 158°. In the crystal, weak C-H⋯Cl hydrogen bonds link the Ru(II) complexes into centrosymmetric dimers. The crystal packing exhibits intra- and inter-molecular C-H⋯π inter-actions resulting in a zigzag pattern in the [101] direction.

  4. Electron Affinity of Phenyl-C61-Butyric Acid Methyl Ester (PCBM)

    SciTech Connect

    Larson, Bryon W.; Whitaker, James B.; Wang, Xue B.; Popov, Alexey A.; Rumbles, Garry; Kopidakis, Nikos; Strauss, Steven H.; Boltalina, Olga V.

    2013-07-25

    The gas-phase electron affinity (EA) of phenyl-C61-butyric acid methyl ester (PCBM), one of the best-performing electron acceptors in organic photovoltaic devices, is measured by lowtemperature photoelectron spectroscopy for the first time. The obtained value of 2.63(1) eV is only ca. 0.05 eV lower than that of C60 (2.68(1) eV), compared to a 0.09 V difference in their E1/2 values measured in this work by cyclic voltammetry. Literature E(LUMO) values for PCBM that are typically estimated from cyclic voltammetry, and commonly used as a quantitative measure of acceptor properties, are dispersed over a wide range between -4.3 and -3.62 eV; the reasons for such a huge discrepancy are analyzed here, and the protocol for reliable and consistent estimations of relative fullerene-based acceptor strength in solution is proposed.

  5. Nanofiltration processes applied to the removal of phenyl-ureas in natural waters.

    PubMed

    Benítez, F Javier; Acero, Juan L; Real, Francisco J; García, Carolina

    2009-06-15

    Four phenyl-urea herbicides (linuron, diuron, chlortoluron and isoproturon) dissolved in a commercial mineral water and in reservoir water were subjected to nanofiltration (NF) processes in cross-flow laboratory equipment with recycling of the retentate stream. Three NF membranes of different nature, with molecual weigth cut-off (MWCO) in the range 150-300 Da, were used. The hydraulic permeabilities of the membranes were determined from filtration experiments of ultra-pure (UP) water. In the NF of the synthetic waters, the permeate fluxes were evaluated, the influence of the main operating conditions (transmembrane pressure, temperature, and MWCO of the membranes) on the steady-state permeate fluxes was established, and the different resistances found in the system, which are responsible of the flux declines, were deduced. The retention coefficients for each herbicide were also evaluated and discussed in view of the nature and characteristics of herbicides and membranes. Finally, the herbicides mass adsorbed on the membranes were also determined and the contribution of the adsorption mechanism to the global retention is pointed out.

  6. Vibrational spectroscopic, structural and quantum chemical studies on N-phenyl-3-pyridinecarboxamide

    NASA Astrophysics Data System (ADS)

    Premkumar, S.; Rekha, T. N.; Asath, R. Mohamed; Jawahar, A.; Mathavan, T.; Benial, A. Milton Franklin

    2016-03-01

    Stable molecular structure of N-phenyl-3-pyridinecarboxmide (Nicotinanilide) was predicted through conformational analysis and the vibrational spectral analysis was carried out using experimental and theoretical methods. The calculated and experimentally observed vibrational frequencies of the molecule were assigned and compared. The observed red shift in Cdbnd O stretching vibrations confirms the mesomeric effects of the Cdbnd O functional group. The n→π* and π→π* electronic transitions of the molecule were predicted from the theoretically simulated ultraviolet-visible spectra and were validated experimentally. Natural bond orbital analysis was performed to investigate the intra-molecular stabilization interactions, which are responsible for the bioactivity and the nonlinear optical property of the molecule. Molecular reactivity and the possible reactive sites of the molecule were investigated based on the frontier molecular orbitals analysis and Fukui functions respectively. The total electron density mapped with the molecular electrostatic potential surface was plotted to confirm the possible reactive sites of the molecule. The title molecule is identified to be a potential candidate for pharmaceutical applications.

  7. Phenyl 3,5-di-tert-butyl-2-hy­droxy­benzoate

    PubMed Central

    Carreño, Alexander; Preite, Marcelo; Manriquez, Juan Manuel; Vega, Andrés; Chavez, Ivonne

    2010-01-01

    The title mol­ecule, C21H26O3, has a six-membered planar carbon ring as the central core, substituted at position 1 with phen­oxy­carbonyl, at position 2 with hy­droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol­ecules within the asymmetric unit. For both independent mol­ecules, the ester carboxyl­ate group is coplanar with the central core, as reflected by the small C—C—O—C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl­ate –CO2 fragment, as reflected by C—O—C—C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl­ate –CO2– group allows the formation of an intra­molecular hydrogen bond, with O⋯O distances of 2.563 (2) and 2.604 (2) Å. PMID:21589569

  8. Poly(phenyl sulfone) anion exchange membranes with pyridinium groups for vanadium redox flow battery applications

    NASA Astrophysics Data System (ADS)

    Zhang, Bengui; Zhang, Enlei; Wang, Guosheng; Yu, Ping; Zhao, Qiuxia; Yao, Fangbo

    2015-05-01

    To develop high performance and cost-effective membranes with low permeability of vanadium ions for vanadium redox flow battery (VRFB) application, poly(phenyl sulfone) anion exchange membranes with pyridinium groups (PyPPSU) are prepared and first investigated for VRFB application. PyPPSU membranes show much lower vanadium ions permeability (0.07 × 10-7-0.15 × 10-7 cm2 min-1) than that of Nafion 117 membrane (31.3 × 10-7 cm2 min-1). As a result, the self-discharge duration of the VRFB cell with PyPPSU membrane (418 h) is about four times longer than that of VRFB cell with Nafion 117 membrane (110 h). Furthermore, the VRFB cell with PyPPSU membrane exhibits higher battery efficiency (coulombic efficiency of 97.8% and energy efficiency of 80.2%) compare with that of VRFB cell with Nafion 117 membrane (coulombic efficiency of 96.1% and energy efficiency of 77.2%) at a high current density of 100 mA cm-2. In addition, PyPPSU membrane exhibits stable performance in 100-cycle test. The results indicate that PyPPSU membrane is high performance and low-cost alternative membrane for VRFB application.

  9. The Effect of Binding Groups on the Seebeck Coefficient of Phenyl Derivative Molecular Junctions

    NASA Astrophysics Data System (ADS)

    Chang, William; Mai, Chengkang; Kotiuga, Michele; Urban, Jeffrey; Neaton, Jeffrey; Bazan, Gui; Segalman, Rachel

    2013-03-01

    Thermoelectrics currently suffer from low efficiencies due to inverse coupling of the Seebeck coefficient and electrical conductivity, limiting the power factor. Decoupling of these two physical properties has previously been demonstrated in molecular junctions. Using an STM break junction measurement technique, we demonstrate the effect that the direct binding group Au-C has on the Seebeck coefficient. Phenyl derivative molecules with an Au-C direct binding group show a significantly lower Seebeck coefficient than molecules with an Au-S binding group. This lower Seebeck coefficient is explained by theoretical calculations as a broadening in the transmission function due to the direct bonding group. This demonstrates the importance of the metal-molecule interface and binding group selection in tuning the transmission function, and the resultant conductance and Seebeck coefficient. This result will lend further insight in rational design for molecules with higher power factors. We would like to acknowledge support from Office of Naval Research - ONR/AFOSR BAA 10-026

  10. Appetite-enhancing Effects of trans-Cinnamaldehyde, Benzylacetone and 1-Phenyl-2-butanone by Inhalation.

    PubMed

    Ogawa, Kakuyou; Ito, Michiho

    2016-01-01

    Fragrance in the air and odours of foods and drinks are reported to affect feeding behaviours of humans and other animals. Many previous studies focusing on the relationship between fragrance and appetite have described a reduction of food intake by fragrance administration to help prevent lifestyle diseases. Aromatic herbal medicines, such as cinnamon bark and fennel fruit, are considered to have appetite-enhancing effects and they are often blended in stomachics for relief of asitia and gastric distress in Japan. These fragrant herbal medicines contain many essential oils and their fragrances are hypothesised to be active substances. In this study, food intake and the expression of neuropeptide Y and proopiomelanocortin in the hypothalamus after inhalation of fragrant compounds or essential oils were investigated in mice. Food intake was increased 1.2-fold and the neuropeptide Y mRNA expression in the hypothalamus was increased significantly in mice that inhaled trans-cinnamaldehyde, benzylacetone or 1-phenyl-2-butanone, compared with the control group. These compounds might be effective for treating loss of appetite (anorexia) or eating disorders in elderly and infirm people via a non-invasive route of administration, namely, inhalation.

  11. Mechanisms of catalytic cleavage of benzyl phenyl ether in aqueous and apolar phases

    SciTech Connect

    He, Jiayue; Lu, Lu; Zhao, Chen; Mei, Donghai; Lercher, Johannes A.

    2014-03-01

    Catalytic pathways for the cleavage of ether bonds in benzyl phenyl ether (BPE) in liquid phase using Ni- and zeolite-based catalysts are explored. In the absence of catalysts, the C-O bond is selectively cleaved in water by hydrolysis, forming phenol and benzyl alcohol as intermediates, followed by alkylation. The hydronium ions catalyzing the reactions are provided by the dissociation of water at 523 K. Upon addition of HZSM-5, rates of hydrolysis and alkylation are markedly increased in relation to proton concentrations. In the presence of Ni/SiO2, the selective hydrogenolysis dominates for cleaving the Caliphatic-O bond. Catalyzed by the dual-functional Ni/HZSM-5, hydrogenolysis occurs as the major route rather than hydrolysis (minor route). In apolar undecane, the non-catalytic thermal pyrolysis route dominates. Hydrogenolysis of BPE appears to be the major reaction pathway in undecane in the presence of Ni/SiO2 or Ni/HZSM-5, almost completely suppressing radical reactions. Density functional theory (DFT) calculations strongly support the proposed C-O bond cleavage mechanisms on BPE in aqueous and apolar phases. These calculations show that BPE is initially protonated and subsequently hydrolyzed in the aqueous phase. Finally, DFT calculations suggest that the radical reactions in non-polar solvents lead to primary benzyl and phenoxy radicals in undecane, which leads to heavier condensation products as long as metals are absent for providing dissociated hydrogen.

  12. Self-assembled cation transporters made from lipophilic 8-phenyl-2'-deoxyguanosine derivatives.

    PubMed

    Martín-Hidalgo, Mariana; Camacho-Soto, Karla; Gubala, Vladimir; Rivera, José M

    2010-11-01

    We have previously reported that 8-phenyl-2'-deoxyguanosine derivatives (8PhGs) are able to extract metal cations from an aqueous phase into an organic phase. Herein we report on the ability of 8PhGs to transport metal cations across a bulk lipophilic liquid membrane. The experiments were performed using lithium, sodium, potassium, and strontium picrate salts with the parent lipophilic Gi, two isomeric 8PhG derivatives, cis-dicyclohexano-18-crown-6 (CD18C6) and [2•2•2] cryptand as reference compounds. The relative amounts of the picrate salts were measured by UV spectroscopy in both, the source phase and the receiving phase over a period of 24 h. The results show that the transport efficiency of the self-assembled ionophores formed by 8PhGs is either similar or superior to that of CD18C6, and in all but one case higher than the parent compound Gi. The varying efficiencies between the derivatives can be attributed to the stability (kinetic and thermodynamic) and the different molecularities of the supramolecules formed by these 8PhGs. The ease of the synthesis of 8PhGs, their anion independent assembly and the fact that the transport efficiency can be modulated as a function of the structure of the 8PhGs bode well for the use of such compounds in the development of novel antimicrobial agents and cation sensing devices.

  13. Mitochondria targeted peptides protect against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity.

    PubMed

    Yang, Lichuan; Zhao, Kesheng; Calingasan, Noel Y; Luo, Guoxiong; Szeto, Hazel H; Beal, M Flint

    2009-09-01

    A large body of evidence suggests that mitochondrial dysfunction and oxidative damage play a role in the pathogenesis of Parkinson's disease (PD). A number of antioxidants have been effective in animal models of PD. We have developed a family of mitochondria-targeted peptides that can protect against mitochondrial swelling and apoptosis (SS peptides). In this study, we examined the ability of two peptides, SS-31 and SS-20, to protect against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity in mice. SS-31 produced dose-dependent complete protection against loss of dopamine and its metabolites in striatum, as well as loss of tyrosine hydroxylase immunoreactive neurons in substantia nigra pars compacta. SS-20, which does not possess intrinsic ability in scavenging reactive oxygen species, also demonstrated significant neuroprotective effects on dopaminergic neurons of MPTP-treated mice. Both SS-31 and SS-20 were very potent (nM) in preventing MPP+ (1-methyl-4-phenylpyridinium)-induced cell death in cultured dopamine cells (SN4741). Studies with isolated mitochondria showed that both SS-31 and SS-20 prevented MPP+-induced inhibition of oxygen consumption and ATP production, and mitochondrial swelling. These findings provide strong evidence that these neuroprotective peptides, which target both mitochondrial dysfunction and oxidative damage, are a promising approach for the treatment of PD.

  14. Mitochondria Targeted Peptides Protect Against 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine Neurotoxicity

    PubMed Central

    Yang, Lichuan; Zhao, Kesheng; Calingasan, Noel Y.; Luo, Guoxiong; Szeto, Hazel H.

    2009-01-01

    Abstract A large body of evidence suggests that mitochondrial dysfunction and oxidative damage play a role in the pathogenesis of Parkinson's disease (PD). A number of antioxidants have been effective in animal models of PD. We have developed a family of mitochondria-targeted peptides that can protect against mitochondrial swelling and apoptosis (SS peptides). In this study, we examined the ability of two peptides, SS-31 and SS-20, to protect against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity in mice. SS-31 produced dose-dependent complete protection against loss of dopamine and its metabolites in striatum, as well as loss of tyrosine hydroxylase immunoreactive neurons in substantia nigra pars compacta. SS-20, which does not possess intrinsic ability in scavenging reactive oxygen species, also demonstrated significant neuroprotective effects on dopaminergic neurons of MPTP-treated mice. Both SS-31 and SS-20 were very potent (nM) in preventing MPP+ (1-methyl-4-phenylpyridinium)-induced cell death in cultured dopamine cells (SN4741). Studies with isolated mitochondria showed that both SS-31 and SS-20 prevented MPP+-induced inhibition of oxygen consumption and ATP production, and mitochondrial swelling. These findings provide strong evidence that these neuroprotective peptides, which target both mitochondrial dysfunction and oxidative damage, are a promising approach for the treatment of PD. Antioxid. Redox Signal. 11, 2095–2104. PMID:19203217

  15. Coordinate covalent C --> B bonding in phenylborates and latent formation of phenyl anions from phenylboronic Acid.

    PubMed

    Glaser, Rainer; Knotts, Nathan

    2006-02-02

    The results are reported of a theoretical study of the addition of small nucleophiles Nu(-) (HO(-), F(-)) to phenylboronic acid Ph-B(OH)(2) and of the stability of the resulting complexes [Ph-B(OH)(2)Nu](-) with regard to Ph-B heterolysis [Ph-B(OH)(2)Nu](-) --> Ph(-) + B(OH)(2)Nu as well as Nu(-)/Ph(-) substitution [Ph-B(OH)(2)Nu](-) + Nu(-) --> Ph(-) + [B(OH)(2)Nu(2)](-). These reactions are of fundamental importance for the Suzuki-Miyaura cross-coupling reaction and many other processes in chemistry and biology that involve phenylboronic acids. The species were characterized by potential energy surface analysis (B3LYP/6-31+G*), examined by electronic structure analysis (B3LYP/6-311++G**), and reaction energies (CCSD/6-311++G**) and solvation energies (PCM and IPCM, B3LYP/6-311++G*) were determined. It is shown that Ph-B bonding in [Ph-B(OH)(2)Nu](-) is coordinate covalent and rather weak (<50 kcal.mol(-1)). The coordinate covalent bonding is large enough to inhibit unimolecular dissociation and bimolecular nucleophile-assisted phenyl anion liberation is slowed greatly by the negative charge on the borate's periphery. The latter is the major reason for the extraordinary differences in the kinetic stabilities of diazonium ions and borates in nucleophilic substitution reactions despite their rather similar coordinate covalent bond strengths.

  16. Density Functional Study of 2-[(R-Phenyl)amine]-1,4-naphthalenediones.

    PubMed

    Gómez-Sandoval, Z; Calaminici, P; Köster, A M; Lotina-Hennsen, B; King-Díaz, B; Macías-Ruvalcaba, N; Aguilar-Martínez, M; Jiménez-Estrada, M

    2007-05-01

    The molecular and electronic structures of a series of 2-[(R-phenyl)amine]-1,4-naphthalenediones (R = m-Me, p-Me, m-Et, p-CF3, p-Hex, p-Et, m-F, m-Cl, p-OMe, p-COMe, p-Bu, m-COOH, p-Cl, p-COOH, p-Br, m-NO2, m-CN, and p-NO2) and their anions are investigated in the framework of density functional theory. The calculations are of all-electron type using a double zeta valence polarization basis set optimized for density functional theory methods. The theoretical study shows that all compounds are nonplanar. The nonplanarity can be rationalized in terms of occupied π orbitals. A linear correlation between the measured half-wave potentials and the calculated gas-phase electron affinities is found. It holds for local as well as generalized gradient corrected functionals. Structural parameters, harmonic vibrational frequencies, and adiabatic and vertical electron affinities as well as orbital and spin density plots of the studied compounds are presented.

  17. Synthesis and molecular modelling studies of phenyl linked oxadiazole-phenylhydrazone hybrids as potent antileishmanial agents.

    PubMed

    Taha, Muhammad; Ismail, Nor Hadiani; Imran, Syahrul; Anouar, El Hassane; Selvaraj, Manikandan; Jamil, Waqas; Ali, Muhammad; Kashif, Syed Muhammad; Rahim, Fazal; Khan, Khalid Mohammed; Adenan, Mohd Ilham

    2017-01-27

    Molecular hybridization yielded phenyl linked oxadiazole-benzohydrazones hybrids 6-35 and were evaluated for their antileishmanial potentials. Compound 10, a 3,4-dihydroxy analog with IC50 value of 0.95 ± 0.01 μM, was found to be the most potent antileishmanial agent (7 times more active) than the standard drug pentamidine (IC50 = 7.02 ± 0.09 μM). The current series 6-35 conceded in the identification of thirteen (13) potent antileishmanial compounds with the IC50 values ranging between 0.95 ± 0.01-78.6 ± 1.78 μM. Molecular docking analysis against pteridine reductase (PTR1) were also performed to probe the mode of action. Selectivity index showed that compounds with higher number of hydroxyl groups have low selectivity index. Theoretical stereochemical assignment was also done for certain derivatives by using density functional calculations.

  18. 11-Methyl-12a-phenyl-9a,12a-dihydrophenanthro[9',10:5,6][1,4]dioxino[2,3-d]thiazole.

    PubMed

    Usman, Anwar; Razak, Ibrahim Abdul; Fun, Hoong Kun; Chantrapromma, Suchada; Zhang, Yan; Xu, Jian Hua

    2002-09-01

    In the title compound, C(24)H(17)NO(2)S, the dioxine and thiazoline rings are distorted from planarity towards a half-chair and an envelope conformation, respectively. The configurations of the dioxine ring, the thiazoline ring and the attached phenyl ring are conditioned by the sp(3) state of the two bridgehead C atoms. The phenanthrene system is nearly coplanar with the dioxine ring, while the attached phenyl ring is orthogonal to the thiazoline ring.

  19. Investigation of the complexation between quinidine carbamate and the enantiomers of 3-chloro-1-phenyl-propanol by circular dichroism and UV spectroscopy

    SciTech Connect

    Guiochon, Georges A; Asnin, Leonid

    2006-04-01

    UV and circular dichroism spectroscopic measurements showed that the molecular interactions in hexane/ethyl-acetate solutions between dihydroquinidine tert-butylcarbamate, used as a model for the quinidine carbamate chiral selector (QD), and 3-chloro-1-phenyl-propanol are too weak to affect the corresponding spectra of these compounds. The weak interactions between QD and 3-chloro-1-phenyl-propanol are probably masked by the formation of self-associated dimeric structures in solution.

  20. 2-[4-Acetyl-5-(biphenyl-4-yl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]phenyl acetate

    PubMed Central

    Yehye, Wagee A.; Ariffin, Azhar; Rahman, Noorsaadah Abdul; Ng, Seik Weng

    2010-01-01

    In the title mol­ecule, C24H20N2O4, the five-membered oxadiazole ring is nearly planar (r.m.s. deviation = 0.053 Å) and the phenyl ring of the biphenyl unit attached to it forms a dihedral angle of 73.2 (1)°; the other phenyl ring is close to coplanar with the oxadiazole ring [dihedral angle = 6.2 (2)°]. PMID:21580697

  1. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  2. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  3. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  4. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  5. 40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-boxy-lic acid, ethyl es-ter, bis- amino]-alkyl-phenyl]-az-o] (ge-ner-ic name). (a) Chemical substance...-lic acid, ethyl ester, bis- -amino]-alkyl-phenyl]-azo] (PMN P-87-304) is subject to reporting under... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ni-tro-thio-phene-car-boxy-lic...

  6. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 3,3â²,5,5â²-Tetra-methyl-bi-phenyl-4,4â²-diol. 721.1800 Section 721.1800 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical...

  7. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 3,3â²,5,5â²-Tetra-methyl-bi-phenyl-4,4â²-diol. 721.1800 Section 721.1800 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical...

  8. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 3,3â²,5,5â²-Tetra-methyl-bi-phenyl-4,4â²-diol. 721.1800 Section 721.1800 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical...

  9. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false 3,3â²,5,5â²-Tetra-methyl-bi-phenyl-4,4â²-diol. 721.1800 Section 721.1800 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical...

  10. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 3,3â²,5,5â²-Tetra-methyl-bi-phenyl-4,4â²-diol. 721.1800 Section 721.1800 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical...

  11. Complexation of mercury(II) with 1-Phenyl-2,3-dimethylpyrazoline-5-thione in 0.1 mol/L HNO3 at 273-338 K

    NASA Astrophysics Data System (ADS)

    Beknazarova, N. S.; Shoalifov, Dzh. O.; Amindzhanov, A. A.; Safarmamadov, S. M.

    2016-12-01

    The complexation of mercury(II) with 1-phenyl-2,3-dimethylpyrazoline-5-thione is studied by means of potentiometry in 0.1 mol/L HNO3 at 273-338 K. The composition of the complexes is determined and their stepwise stability constants are calculated. A pattern is found in altering the stepwise stability constants as the temperature and number of attached 1-phenyl-2,3-dimethylpyrazoline-5-thione molecules rise.

  12. Design, solid-phase synthesis, and evaluation of a phenyl-piperazine-triazine scaffold as α-helix mimetics.

    PubMed

    Moon, Heejo; Lee, Woo Sirl; Oh, Misook; Lee, Huisun; Lee, Ji Hoon; Im, Wonpil; Lim, Hyun-Suk

    2014-12-08

    α-Helices play a critical role in mediating many protein-protein interactions (PPIs) as recognition motifs. Therefore, there is a considerable interest in developing small molecules that can mimic helical peptide segments to modulate α-helix-mediated PPIs. Due to the relatively low aqueous solubility and synthetic difficulty of most current α-helix mimetic small molecules, one important goal in this area is to develop small molecules with favorable physicochemical properties and ease of synthesis. Here we designed phenyl-piperazine-triazine-based α-helix mimetics that possess improved water solubility and excellent synthetic accessibility. We developed a facile solid-phase synthetic route that allows for rapid creation of a large, diverse combinatorial library of α-helix mimetics. Further, we identified a selective inhibitor of the Mcl-1/BH3 interaction by screening a focused library of phenyl-piperazine-triazines, demonstrating that the scaffold is able to serve as functional mimetics of α-helical peptides. We believe that our phenyl-piperazine-triazine-based α-helix mimetics, along with the facile and divergent solid-phase synthetic method, have great potential as powerful tools for discovering potent inhibitors of given α-helix-mediated PPIs.

  13. Zinc oxide nanocubes as a destructive nanoadsorbent for the neutralization chemistry of 2-chloroethyl phenyl sulfide: A sulfur mustard simulant.

    PubMed

    Kiani, Armin; Dastafkan, Kamran

    2016-09-15

    Zinc oxide nanocubes were surveyed for their destructive turn-over to decontaminate 2-chloro ethyl phenyl sulfide, a sulfur mustard simulant. Prior to the reaction, nanocubes were prepared through sol-gel method using monoethanolamine, diethylene glycol, and anhydrous citric acid as the stabilizing, cross linking/structure directing agents, respectively. The formation of nanoscale ZnO, the cubic morphology, crystalline structure, and chemical-adsorptive characteristics were certified by FESEM-EDS, TEM-SAED, XRD, FTIR, BET-BJH, H2-TPR, and ESR techniques. Adsorption and destruction reactions were tracked by GC-FID analysis in which the effects of polarity of the media, reaction time, and temperature on the destructive capability of the surface of nanocubes were investigated and discussed. Results demonstrated that maximum neutralization occurred in n-heptane solvent after 1/2h at 55°C. Kinetic study construed that the neutralization reaction followed the pseudo-second order model with a squared correlation coefficient and rate constant of 0.9904 and 0.00004gmg(-1)s(-1), respectively. Furthermore, GC-MS measurement confirmed the formation of 2-hydroxy ethyl phenyl sulfide (2-HEPS) and phenyl vinyl sulfide (PVS) as neutralization products that together with Bronsted and Lewis acid/base approaches exemplify the role of hydrolysis and elimination mechanisms on the surface of zinc oxide nanocubes.

  14. Synthesis and Anti-tumor Activities of Novel Phenyl Substituted Suberoylanilide Hydroxamic Acid Derivatives Against Human Cancer Cells.

    PubMed

    Xie, Rui; Shi, Jinghua; Qu, Yue; Tang, Pingwah; Wu, Xinying; Yang, Ming; Yuan, Qipeng

    2015-01-01

    A facile and atom-economical boric acid catalyzed direct amidation without any coupling agents for the preparation of Suberoylanilide Hydroxamic Acid (SAHA) and SAHA-based inhibitors targeting anti-proliferation of cancer cells is described. It is applicable to the preparation of SAHA-based inhibitors having an unprotected hydroxyl group in the phenyl ring without the need of the protection. The in-vitro assays data indicate that the nature and the position of the substituents (activating and/or deactivating) in the capping group (phenyl ring) of SAHA-based inhibitors synthesized in this study have a vital impact on the potency of anti-proliferative activity against cancer cells. With low toxicity toward the normal cells, a number of synthesized SAHA-based inhibitors with two substituents in the phenyl ring possess higher antiproliferative activity than SAHA and Cisplatin toward six studied cancer cell lines: A375 human skin cancer cells, A549 human lung cancer cells, MGC80-3 human gastric cancer cells, H460 human lung cancer cells, H1299 human lung cancer cells, and HepG2 human liver cancer cells. Cisplatin is a common chemotherapeutic drug with high cytotoxicity for a variety of cancer treatments. The inhibitors provided in this study might signify future therapeutic drugs for cancer treatment.

  15. The stability studies and in vitro hepatic microsomal metabolism of some alpha-phenyl-N-substituted nitrones in rats.

    PubMed

    Bulut, Gülen; Oktav, Mehmet; Ulgen, Mert

    2004-01-01

    Nitrones are a very important class of synthetic chemicals as synthetic intermediates, antioxidant agents, and metabolic oxidation products of secondary amines and imines used drug, food, cosmetic and printing industry. In the present study, the stability experiments and in vitro metabolism studies using rat microsomal preparations fortified with NADPH were carried out using three different alpha-phenyl-N-substituted nitrones ie alpha-phenyl-N-tert-butylnitrone (PTBN), alpha-(2,6-dichlorophenyl)-N-phenylnitrone (DCPPN) and alpha-phenyl-N-adamantanylnitrone (PADN). The separation of these compounds from the potential degradation, isomerization and metabolic products were performed using a reverse phase HPLC system with a diodearray uv detection. Following stability experiments at 37 degrees C using methanolic nitrone solutions, it was observed that PTBN produced trace amounts of benzaldehyde and the corresponding amide. DCPPN also produced trace amounts of amide. After 12 hours, the amount of the amide significantly increased. PADN produced trace amount of benzaldehyde but not any amide. The proposed compounds were incubated with rat microsomal preparations fortified with NADPH, extracted into dichloromethane (DCM) and finally evaporated under nitrogen in the dark conditions. PTBN was metabolized into corresponding amide whereas DCPPN and PADN did not. With all of the substrates, the corresponding aldehydes are observed with both test and control tubes using denaturated microsomes and without co-factors.

  16. Biotransformation of prochiral 2-phenyl-1,3-di(4-pyridyl)-2-propanol to a chiral N-oxide metabolite.

    PubMed

    Schwartz, M A; Williams, T H; Kolis, S J; Postma, E; Sasso, G J

    1978-01-01

    The prochiral compound, 2-phenyl-1,3-di(4-pyridyl)-2-propanol (PPP) labeled with 3H in the phenyl ring, was administered to rats, dogs, and a human subject. Paper chromatography of the urine indicated that a major metabolite common to all three species was excreted. This metabolite was isolated from the urine of chronically dosed dogs and was identified by mass, nuclear magnetic resonance (NMR), and infrared spectrometry as the N-oxide, 2-phenyl-1-(4-pyridyl)-3-(4-pyridyl-1-oxide)-2-propanol. In addition, polarimetry indicated that this metabolite was levorotatory. Examination of the enantiomeric purity of a crystallized sample of the metabolite by NMR spectroscopy of resolvable diastereomeric salts formed with lasalocid revealed the presence of only the levorotatory enantiomer. Accordingly, this metabolic N-oxide formation in the dog was at least stereoselective, and perhaps stereospecific. The N-oxidation of PPP was also demonstrated in vitro with 9000 g supernatant fraction of rat liver fortified with an NADPH generating system, and this reaction was inducible by phenobarbital, indicating that it is mediated by the cytochrome P-450 mixed-function oxidase system. This study, in addition to providing another example of the pyridyl N-oxidation pathway, illustrates the necessity of considering the stereochemical aspects of the metabolism of prochiral drugs.

  17. Synthesis of 2-phenyl-4,5-substituted oxazoles by copper-catalyzed intramolecular cyclization of functionalized enamides.

    PubMed

    Vijay Kumar, S; Saraiah, B; Misra, N C; Ila, H

    2012-12-07

    An efficient two-step synthesis of 2-phenyl-4,5-substituted oxazoles involving intramolecular copper-catalyzed cyclization of highly functionalized novel β-(methylthio)enamides as the key step has been reported. These enamides are obtained by nucleophilic ring-opening of newly synthesized 4-[(methylthio)hetero(aryl)methylene]-2-phenyl-5-oxazolone precursors by alkoxides, amines, amino acid esters and aryl/alkyl Grignard reagents, thus leading to the introduction of an ester, N-substituted carboxamide or acyl functionalities at 4-position of the product oxazoles. Synthesis of two naturally occurring 2,5-diaryloxazoles, i.e., texamine and uguenenazole, via two-step hydrolysis-decarboxylation of the corresponding 2,5-diaryloxazole-4-carboxylates has also been described. Similarly, three of the serine-derived oxazole-4-carboxamides were elaborated to novel trisubstituted 4,2'-bisoxazoles through DAST/DBU-mediated cyclodehydration-dehydrohalogenation sequence. The present protocol is complementary and an improvement to our previously reported silver carbonate-induced cyclization of β-bis(methylthio)enamides to 2-phenyl-5-(methylthio)-4-substituted oxazoles.

  18. Vibrational spectra and assignments of 3-phenylprop-2-en-1-ol (cinnamyl alcohol) and 3-phenyl-1-propanol

    NASA Astrophysics Data System (ADS)

    Badawi, Hassan M.; Förner, Wolfgang

    2011-09-01

    The complex conformational behavior of 3-phenylprop-2-en-1-ol (cinnamyl alcohol) and its saturated analogue 3-phenyl-1-propanol were investigated at the DFT-B3LYP/6-311G **, MP2 and MP4(SDQ) levels of theory. The unsaturated 3-phenylprop-2-en-1-ol was predicted to exist in Cg and Gg1 conformational mixture as a result of competitive conjugation and hyperconjugation interactions in the molecule. The saturated 3-phenyl-1-propanol was predicted to exist predominantly in a Ggg structure as a result of predominant steric hindrances in the alcohol. Only the one predominant form was identified in the infrared and Raman spectra of both alcohols. The excellent agreement between the calculated wavenumbers and the observed ones in the infrared and Raman spectra supports the conclusion that each of the two alcohols is present in one predominant form in the condensed phases. The vibrational frequencies of 3-phenylprop-2-en-1-ol and 3-phenyl-1-propanol in their lowest energy forms were computed at the B3LYP level and tentative vibrational assignments were provided on the basis of combined calculated and experimental data.

  19. Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents.

    PubMed

    Kim, Tae Woo; Yong, Yeonjoong; Shin, Soon Young; Jung, Hyeryoung; Park, Kwan Ha; Lee, Young Han; Lim, Yoongho; Jung, Kang-Yeoun

    2015-04-01

    Rapid and efficient synthesis of a phenyl-1H-1,2,3-triazole library enabled cost-effective biological testing of a range of novel non-steroidal anti-inflammatory drugs with potential for improved drug efficacy and toxicity profiles. Anti-inflammatory activities of the phenyl-1H-1,2,3-triazole analogs synthesized in this report were assessed using the xylene-induced ear edema model in mice. At least four analogs, 2a, 2b, 2c, and 4a, showed more potent effects than the reference anti-inflammatory drug diclofenac at the same dose of 25 mg/kg. To explore relationships between the structural properties of phenyl-1H-1,2,3-triazole analogs and their anti-inflammatory activities in xylene-induced ear edema, comparative molecular field analysis was performed, and pharmacophores showing good anti-inflammatory activities were identified based on an analysis of contour maps obtained from comparative molecular field analysis. The anti-inflammatory effect on the molecular level was tested by the expression of tumor necrosis factor-alpha induced COX-2 using Western blots. Because the addition of the analog 2c caused the expression change of TNF-α induced COX-2, the molecular binding mode between 2c and COX-2 was elucidated using in silico docking.

  20. Experimental and theoretical study on the reaction of N3-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride

    NASA Astrophysics Data System (ADS)

    Modzelewska-Banachiewicz, Bożena; Paprocka, Renata; Mazur, Liliana; Saczewski, Jarosław; Kutkowska, Jolanta; Stępień, Dorota K.; Cyrański, Michał

    2012-08-01

    Two new 1,2,4-triazole-containing alkenoic acid derivatives were obtained from the reaction of N-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride, depending on the reaction conditions. The structures of 2-((4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl)methyl)acrylic acid or (E)-2-methyl-3(4-phenyl-5-(pyridine-2-yl)-4H-1,2,4-triazol-3-yl)acrylic acid were confirmed by means of 1D and 2D NMR spectroscopic data as well as by single-crystal X-ray diffraction analysis. The experiential 1H and 13C chemical shifts were compared with those calculated with B3LYP, EDF1, and EDF2 density functional theories. The theoretical study of the observed terminal-to-internal alkene isomerization was performed with density functional (DFT) B3LYP/6-31+G∗ method using SM8 water and DMF solvation models. Antimicrobial activities of the newly prepared alkenoic acid derivatives were verified experimentally by a broth microdilution method.

  1. Dimethyl phenyl piperazine iodide (DMPP) induces glioma regression by inhibiting angiogenesis

    SciTech Connect

    He, Yan-qing; Li, Yan; Wang, Xiao-yu; He, Xiao-dong; Jun, Li; Chuai, Manli; Lee, Kenneth Ka Ho; Wang, Ju; Wang, Li-jing; Yang, Xuesong

    2014-01-15

    1,1-Dimethyl-4-phenyl piperazine iodide (DMPP) is a synthetic nicotinic acetylcholine receptor (nAChR) agonist that could reduce airway inflammation. In this study, we demonstrated that DMPP could dramatically inhibit glioma size maintained on the chick embryonic chorioallantoic membrane (CAM). We first performed MTT and BrdU incorporation experiments on U87 glioma cells in vitro to understand the mechanism involved. We established that DMPP did not significantly affect U87 cell proliferation and survival. We speculated that DMPP directly caused the tumor to regress by affecting the vasculature in and around the implanted tumor on our chick CAM model. Hence, we conducted detailed analysis of DMPP's inhibitory effects on angiogenesis. Three vasculogenesis and angiogenesis in vivo models were used in the study which included (1) early chick blood islands formation, (2) chick yolk-sac membrane (YSW) and (3) CAM models. The results revealed that DMPP directly suppressed all developmental stages involved in vasculogenesis and angiogenesis – possibly by acting through Ang-1 and HIF-2α signaling. In sum, our results show that DMPP could induce glioma regression grown on CAM by inhibiting vasculogenesis and angiogenesis. - Highlights: ●We demonstrated that DMPP inhibited the growth of glioma cells on chick CAM. ●DMPP did not significantly affect the proliferation and survival of U87 cells. ●We revealed that DMPP suppressed vasculogenesis and angiogenesis in chick embryo. ●Angiogenesis in chick CAM was inhibited by DMPP via most probably Ang-1 and HIF-2α. ●DMPP could be potentially developed as an anti-tumor drug in the future.

  2. Detection thresholds for phenyl ethyl alcohol using serial dilutions in different solvents.

    PubMed

    Tsukatani, Toshiaki; Miwa, Takaki; Furukawa, Mitsuru; Costanzo, Richard M

    2003-01-01

    Detection thresholds are typically obtained by presenting a subject with serial dilutions of an odorant. Many factors, including the solvent used to dilute the odorant, can influence the measurement of detection thresholds. Differences have been reported in detection thresholds for phenyl ethyl alcohol (PEA) when different solvents are used. In this study we used gas chromatography (GC) to investigate further the effect of solvent on odor detection thresholds. We used a single ascending method and serial dilutions of PEA in four different solvents--liquid paraffin (LP), mineral oil (MO), propylene glycol (PG) and dipropylene glycol (DPG)--to determine the PEA thresholds for 31 adult subjects. For each solvent, we prepared eight serial log base 10 step dilutions (1-8), with corresponding liquid PEA concentrations of 6.3 x 10(1)-6.3 x 10(-6) (% v/v). We found that the threshold concentrations for PEA in LP (step 6.5) and PEA in MO (step 5.5) were significantly lower (P < 0.05) than for PEA in PG (step 4.0) and DPG (step 4.0) We then used GC to measure both the liquid and gas PEA concentrations for the dilution steps prepared with LP and PG. Although there were large threshold differences in the liquid concentrations of PEA in LP and PG, the headspace gas concentrations of PEA were the same. These results demonstrate the importance of determining the gas concentration of odorant stimuli when performing odor threshold measurements, in particular when comparing odor detection thresholds obtained using different solvents.

  3. Interface and Pore Confinement Effects in the Pyrolysis of Phenethyl Phenyl Ether

    SciTech Connect

    Kidder, Michelle; Buchanan III, A C; Britt, Phillip F

    2009-01-01

    Lignin, a complex biopolymer found in vascular plants and as the byproduct of pulping, is anticipated to be one of the next generation s resources for fuel and chemical feedstocks. To reach the point where lignin can efficiently be utilized, the products from its pyrolysis must be controlled, thus key factors in understanding what will maximize product yields and promote product selectivity must be investigated. We approach this problem through a systematic investigation starting with the simplest model compound that represents the dominant aryl glycerol--aryl ether interunit linkage in lignin, phenethyl phenyl ether, PhCH2CH2OPh (PPE). The decomposition of PPE at 375 C in the gas and solution phases is now well understood, and occurs through a free-radical chain pathway involving competitive hydrogen abstraction at the  or carbon, which leads to different products and is described as the - product selectivity. This selectivity not only depends on relevant substituents, but it is also sensitive to interactions with metal oxide surfaces. Furthermore, covalent confinement in a nanoporous silica, hydrogen bonding interactions with the surface, and changes in the local environment with co-attached spacer molecules all can influence the product selectivity significantly. Here we will describe the impact of pore confinement and pore size, metal oxide surface acidity, hydrogen bonding of oxygen functional groups at the interface, and the influence of organic molecular structure at the interface on the pyrolysis product selectivity of this important lignin linkage.

  4. Spectroscopic characterization of structural isomers of naphthalene: 1-Phenyl-1-butyn-3-ene

    NASA Astrophysics Data System (ADS)

    Sebree, Joshua A.; Plusquellic, David F.; Zwier, Timothy S.

    2011-12-01

    Laser induced fluorescence (LIF), single vibronic level dispersed fluorescence (DFL) spectra, and high resolution rotationally resolved scans of the S 0-S 1 transition of the C 10H 8 isomer 1-phenyl-1-butyn-3-ene have been recorded under jet-cooled conditions. The S 0-S 1 origin of PAV at 34 922 cm -1 is very weak. A vibronic band located 464.0 above the origin, assigned as 30 10, dominates the LIF excitation spectrum, with intensity arising from vibronic coupling with the S 2 state. High resolution scans of the S 0-S 1 origin and 30 10 vibronic bands determine that the former is a 65:35 a: b hybrid band, while 30 10 is a pure a-type band, confirming the role for vibronic coupling and identifying the coupled state as the S 2 state. DFL spectra of all vibronic bands in the first 800 cm -1 of the spectrum were recorded. A near-complete assignment of the vibronic structure in both S 0 and S 1 states is obtained. Herzberg-Teller vibronic coupling is carried by two vibrations, ν28 and ν30, involving in-plane deformations of the vinylacetylene side chain, leading to Duschinsky mixing evident in the intensities of transitions in excitation and DFL spectra. Extensive Duschinsky mixing is also present among the lowest five out-of-plane vibrational modes, involving motion of the side chain. Comparison with the results of DFT B3LYP and TDDFT calculations with a 6-311+G(d,p) basis set confirm and strengthen the assignments.

  5. 2-Phenyl-APB-144-Induced Retinal Pigment Epithelium Degeneration and Its Underlying Mechanisms

    PubMed Central

    Kurashima, Hiroaki; Nakamura, Daisuke; Komatsu, Tomoko; Yasuda, Yuki; Habashita-Obata, Sayo; Ichikawa, Sanae; Katsuta, Osamu; Iwawaki, Takao; Kohno, Kenji

    2015-01-01

    Abstract Purpose: To investigate the efficacy of 2-phenyl-APB-144 (APB)-induced retinopathy in a rat model and its underlying mechanisms, with a particular focus on retinal pigment epithelium (RPE) degeneration. Methods: Electroretinograms (ERGs) were evaluated in APB-administered rats. In ARPE-19 cells, cathepsin, and autophagy marker LC3 were analyzed by western blotting or immunohistochemistry. Organelle pH alterations were detected by Acridine Orange Staining. Endoplasmic reticulum stress-dependent or -independent cell death signaling was analyzed by reporter gene assays of activating transcription factor 4 (ATF4), immunoglobulin heavy-chain binding protein (BiP), inositol-requiring enzyme 1α (IRE1α), quantitative reverse transcription-polymerase chain reaction of CHOP mRNA, and the effects of pharmacological eukaryotic initiation factor 2α (eIF2α) dephosphorylation inhibitor, Salubrinal. The pharmacological effects of Salubrinal were examined by fluorophotometry, electrophysiology, and histopathology. Results: APB-induced ERG amplitude reduction and fluorescein permeability enhancement into the vitreous body of rats were determined. In ARPE-19 cells, APB-induced organelle pH alterations, imbalances of procathepsin and cathepsin expression, the time-dependent accumulation of LC3-II, and the translational activation of ATF4 were determined. Salubrinal protected against APB-induced cell death and inhibited ATF4 downstream factor CHOP mRNA induction. In APB-induced rat retinopathy, systemic Salubrinal alleviated the enhanced fluorescein permeability into the vitreous body from the RPE, the reductions in ERG amplitudes, and RPE degeneration. Conclusions: Organelle pH alterations and autophagy impairments are involved in APB-induced RPE cell death. Inhibition of eIF2α dephosphorylation protected the RPE in vivo and in vitro. These findings suggested that APB-induced retinopathy is a valuable animal model for exploring the mechanism of RPE-driven retinopathy

  6. PAH formation under single collision conditions: reaction of phenyl radical and 1,3-butadiene to form 1,4-dihydronaphthalene.

    PubMed

    Kaiser, R I; Parker, D S N; Zhang, F; Landera, A; Kislov, V V; Mebel, A M

    2012-05-03

    The crossed beam reactions of the phenyl radical (C(6)H(5), X(2)A(1)) with 1,3-butadiene (C(4)H(6), X(1)A(g)) and D6-1,3-butadiene (C(4)D(6), X(1)A(g)) as well as of the D5-phenyl radical (C(6)D(5), X(2)A(1)) with 2,3-D2-1,3-butadiene and 1,1,4,4-D4-1,3-butadiene were carried out under single collision conditions at collision energies of about 55 kJ mol(-1). Experimentally, the bicyclic 1,4-dihydronaphthalene molecule was identified as a major product of this reaction (58 ± 15%) with the 1-phenyl-1,3-butadiene contributing 34 ± 10%. The reaction is initiated by a barrierless addition of the phenyl radical to the terminal carbon atom of the 1,3-butadiene (C1/C4) to form a bound intermediate; the latter underwent hydrogen elimination from the terminal CH(2) group of the 1,3-butadiene molecule leading to 1-phenyl-trans-1,3-butadiene through a submerged barrier. The dominant product, 1,4-dihydronaphthalene, is formed via an isomerization of the adduct by ring closure and emission of the hydrogen atom from the phenyl moiety at the bridging carbon atom through a tight exit transition state located about 31 kJ mol(-1) above the separated products. The hydrogen atom was found to leave the decomposing complex almost parallel to the total angular momentum vector and perpendicularly to the rotation plane of the decomposing intermediate. The defacto barrierless formation of the 1,4-dihydronaphthalene molecule involving a single collision between a phenyl radical and 1,3-butadiene represents an important step in the formation of polycyclic aromatic hydrocarbons (PAHs) and their partially hydrogenated counterparts in combustion and interstellar chemistry.

  7. HPLC determination of cyanuric acid in swimming pool waters using phenyl and confirmatory porous graphitic carbon columns.

    PubMed

    Cantú, R; Evans, O; Kawahara, F K; Wymer, L J; Dufour, A P

    2001-07-15

    The chlorinated salts of cyanuric acid have found an important role in recreational swimming pool waters across the United States. Upon application to pool water, they can (1) release disinfectant chlorine or (2) stabilize the free available chlorine by acting as chlorine reservoirs in the form of cyanuric acid, preventing the photolytic destruction of residual chlorine by sunlight. Recommended levels of the cyanuric acid stabilizer are in the 10-100 mg/L concentration range according to the National Swimming Pool Foundation (San Antonio, TX). Two isocratic HPLC methods with UV detection (213 nm) employing phenyl and porous graphitic carbon (PGC) columns and phosphate buffer eluents (pH 6.7 and pH 9.1, respectively) were developed to accurately measure cyanuric acid in swimming pools. The two methods allowed fast separation and detection of the stabilizer in 4 (phenyl) and 8 (PGC) min. Both methods offered practical sensitivities with method detection limits of 0.07 (phenyl) and 0.02 mg/L (PGC). Neither one of the two methods required the use of sample cleanup cartridges. They exhibit chromatograms with excellent baseline stability enabling low-level quantitation. Most important, the PGC column had a useful lifetime of five months and 500 sample analyses/column. Eleven pool water samples were fortified with 4.8-50.0 mg/L stabilizer, and the average recovery was 99.8%. Finally, statistical analysis on the relative precisions of the two methods indicated equivalence at the 0.05 critical level.

  8. Discovery of novel N,N-3-phenyl-3-benzylaminopropionanilides as potent inhibitors of cholesteryl ester transfer protein in vivo.

    PubMed

    Xie, Honglei; Li, Yiqun; Bai, Changlin; Wang, Ruifeng; Liu, Chunchi; Hao, Chenzhou; Lin, Bin; Cheng, Maosheng; Zhao, Dongmei

    2016-04-15

    Epidemiological studies have identified that the risk of cardiovascular events increases due to the decreased levels of high density lipoprotein-cholesterol and the elevated levels of low density lipoprotein-cholesterol. Herein, we report a novel series of N,N-3-phenyl-3-benzylaminopropionanilide derivatives, which were identified as potent cholesteryl ester transfer protein (CETP) inhibitor. The initial lead compound L10 (IC50 8.06 μM) was found by pharmacophore-based virtual screening (Dong-Mei Zhao et al., Chin. Chem. Lett.2014, 25, 299). After systematic structure variation and biological testing against CETP, two different series were identified as scaffolds for potent CETP inhibitors. One is N,N-3-phenyl-3-benzylaminopropanamide derivatives, which were investigated in our previous paper (Bioorg. Med. Chem.2015, doi: http://dx.doi.org/10.1016/j.bmc.2015.12.010). The most potent compound HL16 in that series has the IC50 of 0.69 μM. The other series is N,N-3-phenyl-3-benzylaminopropionanilide derivatives, which was investigated in current study. Further optimization of the structure-activity relationship (SAR) resulted in H16 (IC50 0.15 μM), which was discovered as a potent CETP inhibitor in vitro by BODIPY-CE fluorescence assay. In addition, the results of pharmacodynamics studies showed that H16 exhibited both favorable HDL-C enhancement and LDL-C reduction in vivo by hamster. It also has an excellent stability in rat liver microsomal.

  9. Synthesis and Evaluation of Fluorine-Substituted Phenyl Acetate Derivatives as Ultra-Short Recovery Sedative/Hypnotic Agents

    PubMed Central

    Zhang, Heng; Xu, Xiangqing; Chen, Yin; Qiu, Yinli; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen

    2014-01-01

    Background Soft drugs are molecules that are purposefully designed to be rapidly metabolized (metabolically labile). In anesthesia, the soft drug is useful because it enables precise titration to effect and rapid recovery, which might allow swift and clear-headed recovery of consciousness and early home readiness. Propofol may cause delayed awakening after prolonged infusion. Propanidid and AZD3043 have a different metabolic pathway compared to propofol, resulting in a short-acting clinical profile. Fluorine imparts a variety of properties to certain medicines, including an enhanced absorption rate and improved drug transport across the blood-brain barrier. We hypothesized that the introduction of fluorine to the frame structure of propanidid and AZD3043 would further accelerate the swift and clear-headed recovery of consciousness. To test this hypothesis, we developed a series of fluorine-containing phenyl acetate derivatives. Methodology/Principal Findings Fluorine-containing phenyl acetate derivatives were synthesized, and their hypnotic potencies and durations of LORR following bolus or infusion administration were determined in mice, rats and rabbits. The metabolic half-lives in the blood of various species were determined chromatographically. In vitro radioligand binding and γ-aminobutyric acidA (GABAA) receptor electrophysiology studies were performed. Among the 12 synthesized fluorine-containing phenyl acetate derivatives, compound 5j induced comparable duration of LORR with AZD3043, but more rapid recovery than AZD3043, propanidid and propofol. The time of compound 5j to return to walk and behavioral recovery are approximately reduced by more than 50% compared to AZD3043 in mice and rats and rabbits. The HD50 of compound 5j decreased with increasing animal size. Conclusions/Significance The rapid recovery might make compound 5j suitable for precise titration and allow swift and clear-headed recovery of consciousness and early home readiness. PMID:24796695

  10. trans-Diaqua­bis­(l-phenyl­alaninato-κ2 N,O)nickel(II)

    PubMed Central

    Ghorbanloo, Massomeh; Shahbakhsh, Nahid; Choquesillo-Lazarte, Duane

    2012-01-01

    In the title compound, [Ni(C9H10NO2)2(H2O)2], the coordination geometry around the NiII ion can be described as distorted octa­hedral, with two N atoms and two O atoms from phenyl­alaninate ligands in the basal plane and two aqua O atoms at the axial sites. The crystal packing is stabilized by inter­molecular O—H⋯O and N—H⋯O hydrogen bonds. PMID:22589818

  11. Conjugate addition of lithium N-phenyl-N-(α-methylbenzyl)amide: application to the asymmetric synthesis of (R)-(-)-angustureine.

    PubMed

    Bentley, Scott A; Davies, Stephen G; Lee, James A; Roberts, Paul M; Thomson, James E

    2011-05-20

    The conjugate addition of lithium (R)-N-phenyl-N-(α-methylbenzyl)amide to a range of α,β-unsaturated 4-methoxyphenyl esters proceeds with excellent levels of diastereoselectivity to give the corresponding β-amino esters in good yield and as single diastereoisomers (>99:1 dr). The synthetic utility of this methodology has been demonstrated via the short and concise asymmetric synthesis of the tetrahydroquinoline alkaloid (R)-(-)-angustureine in six steps and 32% overall yield from commercially available oct-2-enoic acid.

  12. 7-Phenyl-sulfonyl-2,3-dihydro-7H-1,4-benzodioxino[6,7-b]carbazole.

    PubMed

    Kanchanadevi, J; Dhayalan, V; Mohanakrishnan, A K; Anbalagan, G; Chakkaravarthi, G; Manivannan, V

    2010-11-20

    In the title compound, C(24)H(17)NO(4)S, the phenyl ring makes a dihedral angle of 88.12 (5)° with the carbazole unit. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal packing exhibits weak inter-molecular C-H⋯O and C-H⋯π inter-actions. Two C atoms of the 2,3-dihydro-1,4-dioxine fragment are disordered over two positions with site-occupancy factors of 0.718 (11) and 0.282 (11).

  13. 1-Formyl-3-phenyl-5-(4-isopropylphenyl)-2-pyrazoline: Synthesis, characterization, antimicrobial activity and DFT studies

    NASA Astrophysics Data System (ADS)

    Sid, Assia; Messai, Amel; Parlak, Cemal; Kazancı, Nadide; Luneau, Dominique; Keşan, Gürkan; Rhyman, Lydia; Alswaidan, Ibrahim A.; Ramasami, Ponnadurai

    2016-10-01

    The structure of 1-formyl-3-phenyl-5-(4-isopropylphenyl)-2-pyrazoline synthesized as single crystal was investigated by FTIR, NMR, XRD. Experimental data were complemented by quantum mechanical calculations. XRD data show that the compound crystallizes in the triclinic system (P-1) via trans isomer (a = 6.4267(4) Å, b = 10.9259(12) Å, c = 12.4628(9) Å and α = 102.894(8)°, β = 102.535(6)°, γ = 101.633(7)°). Anti-microbial screening results indicate that the compound shows promising activity. The theoretically predicted and experimentally obtained parameters reveal further insight into pyrazoline systems.

  14. Novel selectfluor and deoxo-fluor-mediated rearrangements. New 5(6)-methyl and phenyl methanopyrrolidine alcohols and fluorides.

    PubMed

    Krow, Grant R; Lin, Guoliang; Moore, Keith P; Thomas, Andrew M; DeBrosse, Charles; Ross, Charles W; Ramjit, Harri G

    2004-05-13

    Stereoselective syntheses of novel 5,6-difunctionalized-2-azabicyclo[2.1.1]hexanes containing 5-anti-fluoro or hydroxyl in one methano bridge and a variety of syn- or anti-chloro, fluoro, hydroxy, methyl, or phenyl substituents in the other methano bridge have been effected. Rearrangements of iodides to alcohols were initiated using Selectfluor. Rearrangement of alcohols to fluorides was initiated using Deoxo-Fluor. Ring opening of 2-azabicyclo[2.2.0]hex-5-ene exo-epoxide with organocopper reagents is regioselective at C(5).

  15. Sequences in the HSP90 promoter form G-quadruplex structures with selectivity for disubstituted phenyl bis-oxazole derivatives.

    PubMed

    Ohnmacht, Stephan A; Micco, Marialuisa; Petrucci, Vanessa; Todd, Alan K; Reszka, Anthony P; Gunaratnam, Mekala; Carvalho, Marta A; Zloh, Mire; Neidle, Stephen

    2012-09-15

    The HSP90 protein is an important target in cancer. We report here that stable quadruplex DNAs can be formed from a promoter sequence in the HSP90 gene, on the basis of melting, circular and NMR studies, and show that these can be selectively targeted by non-macrocyclic quadruplex-stabilizing phenyl bis-oxazole derivatives. These do not bind significantly to duplex DNA and show low stabilization of the human telomeric quadruplex. These results suggest an approach to targeting HSP90 at the DNA level.

  16. Effect of excitation conditions on photostability of 2-(4pyridyl)-5 phenyl)oxazole laser media

    NASA Astrophysics Data System (ADS)

    Kuznetsova, Rimma T.; Kopylova, Tat'yana N.; Degtjarenko, K. M.; Tel'minov, Evgenii N.; Samsonova, Lyibov G.; Sergeev, A. K.; Nesterenko, S. N.

    1995-08-01

    A method of photostability examination of dye active media is described. Quantum yield of phototransformation, relative yield of some final photoproducts, as well as laser lifetime of 2- (4pyridyl)-5 phenyl)oxazole (4PyPO) ethanol solutions were measured. These characteristics were studied as functions of dye concentration, excitation power, and pulse duration, as well as type of irradiation (by means of spontaneous or lasing). Transient T-T absorption spectra were monitored. Effects of different additions into solution of T-T absorption and photostability of the medium were investigated. Improvement in lifetime of 4PyPO active media is discussed.

  17. Feasibility of incorporating the nitrogen-loss inhibitors dicyandiamide, thiourea, phenyl phosphorodiamidate, and potassium ethyl xanthate into granular urea

    SciTech Connect

    Gautney, J.; Kim, Y.K.; Gagen, P.M.

    1983-01-01

    Laboratory tests were conducted to determine the feasibility of incorporating the nitrogen loss inhibitors dicyandiamide (DCD), thiourea (TU), phenyl phosphorodiamidate (PPDA), and potassium ethyl xanthate (PEX) into granular urea. Tests were made to determine the stabilities, solubilities, and dissolution rates of the inhibitors in urea melts and urea solutions; to determine the effect of inhibitor addition on the rate of weight loss and qualitative composition of volatiles evolving from urea melts; to determine the melting point diagrams for the urea inhibitor systems; and to determine the heat of fusion for the urea-inhibitor mixtures.

  18. Biocatalytic resolution of benzyl glycidyl ether and its derivates by Talaromyces flavus: effect of phenyl ring substituents on enantioselectivity.

    PubMed

    Wei, Chun; Chen, Yunyun; Shen, Honglei; Wang, Shan; Chen, Lin; Zhu, Qing

    2012-08-01

    Talaromyces flavus containing a constitutive epoxide hydrolase (EH) resolved racemic benzyl glycidyl ether and nine derivatives into their (R)-enantiomers. After optimization of the fermentation conditions, the specific EH activity and biomass concentration were improved from 13.5 U/g DCW and 14.8 g DCW/l to 26.2 U/g DCW and 31.3 g DCW/l, respectively, with final values for e.e. ( s ) of 96 % and E of 13 with (R)-benzyl glycidyl ether. Substituents on the phenyl ring, however, gave low enantioselectivities.

  19. Investigation of a Bicyclo[1.1.1]pentane as a Phenyl Replacement within an LpPLA2 Inhibitor.

    PubMed

    Measom, Nicholas D; Down, Kenneth D; Hirst, David J; Jamieson, Craig; Manas, Eric S; Patel, Vipulkumar K; Somers, Don O

    2017-01-12

    We describe the incorporation of a bicyclo[1.1.1]pentane moiety within two known LpPLA2 inhibitors to act as bioisosteric phenyl replacements. An efficient synthesis to the target compounds was enabled with a dichlorocarbene insertion into a bicyclo[1.1.0]butane system being the key transformation. Potency, physicochemical, and X-ray crystallographic data were obtained to compare the known inhibitors to their bioisosteric counterparts, which showed the isostere was well tolerated and positively impacted on the physicochemical profile.

  20. Aryl-phenyl scrambling in intermediate organopalladium complexes: a gas-phase study of the Mizoroki-Heck reaction.

    PubMed

    Fiebig, Lukas; Schlörer, Nils; Schmalz, Hans-Günther; Schäfer, Mathias

    2014-04-22

    The intramolecular aryl-phenyl scrambling reaction within palladium-DPPP-aryl complex (DPPP=1,3-bis(diphenylphosphino)propane) ions was analyzed by state-of-the-art tandem MS, including gas-phase ion/molecule reactions. The Mizoroki-Heck cross-coupling reaction was performed in the gas phase, and the intrinsic reactivity of important intermediates could be examined. Moreover, linear free-energy correlations were applied, and a mechanism for the scrambling reaction proceeding via phosphonium cations was assumed.

  1. Crystal structures of three carbazole derivatives: 12-ethyl-7-phenyl­sulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimeth­oxy-2-nitro­phen­yl)-4-hy­droxy-9-phenyl­sulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenyl­sulfonyl-7H-benzofuro[2,3-b]carbazole, (3)

    PubMed Central

    Gangadharan, Rajeswari; Narayanan, P.; Sethusankar, K.; Saravanan, Velu; Mohanakrishnan, Arasambattu K.

    2016-01-01

    The three title compounds, C26H19NO3S, (1), C27H20N2O8S, (2), and C30H19NO3S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzo­furan moiety fused to a carbazole unit. In (2), a di­meth­oxy­nitro­phenyl ring is attached to the carbazole moiety. In the three derivatives, a phenyl­sulfonyl group is attached to the N atom of the carbazole unit. Compound (1) crystallizes with two independent mol­ecules in the asymmetric unit (A and B). The carbazole skeleton in the three compounds is essentially planar. In compound (1), the benzene ring of the phenyl­sulfonyl moiety is almost orthogonal to the carbazole moiety, with dihedral angles of 85.42 (9) and 84.52 (9)° in mol­ecules A and B, respectively. The benzene ring of the phenyl­sulfonyl group in compounds (2) and (3) are inclined to the carbazole moiety, making dihedral angles of 70.73 (13) and 81.73 (12)°, respectively. The S atom has a distorted tetra­hedral configuration in all three compounds. In the crystals, C—H⋯O hydrogen bonds give rise to R 2 2(12) inversion dimers for compound (1), and to R 2 2(24) inversion dimers and R 4 4(40) ring motifs for compound (2). The crystal packing in (1) also features C—H⋯π and π–π inter­actions [shortest inter­centroid distance = 3.684 (1) Å], leading to supra­molecular three-dimensional aggregation. In the crystal of compound (2), the combination of the various C—H⋯O hydrogen bonds leads to the formation of a three-dimensional network. In the crystal of compound (3), mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains running parallel to the a axis, and the chains are linked by C—H⋯π inter­actions, forming corrugated sheets parallel to the ab plane. PMID:27980821

  2. Novel glutathione conjugates of phenyl isocyanate identified by ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance.

    PubMed

    Johansson Mali'n, Tove; Lindberg, Sandra; Åstot, Crister

    2014-01-01

    Phenyl isocyanate is a highly reactive compound that is used as a reagent in organic synthesis and in the production of polyurethanes. The potential for extensive occupational exposure to this compound makes it important to elucidate its reactivity towards different nucleophiles and potential targets in the body. In vitro reactions between glutathione and phenyl isocyanate were studied. Three adducts of glutathione with phenyl isocyanate were identified using ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance (NMR). Mass spectrometric data for these adducts have not previously been reported. Nucleophilic attack on phenyl isocyanate occurred via either the cysteinyl thiol group or the glutamic acid α-amino group of glutathione. In addition, a double adduct was formed by the reaction of both these moieties. NMR analysis confirmed the proposed structure of the double adduct, which has not previously been described. These results suggest that phenyl isocyanate may react with free cysteines, the α-amino group and also with lysine residues whose side chain contains a primary amine.

  3. Structure and properties of bis(1-phenyl-1h-tetrazole-5-thiolate)diiron tetranitrosyl

    NASA Astrophysics Data System (ADS)

    Sanina, N. A.; Kozub, G. I.; Kondrat'eva, T. A.; Shilov, G. V.; Korchagin, D. V.; Emel'yanova, N. S.; Poleshchuk, O. Kh.; Chernyak, A. V.; Kulikov, A. V.; Mushenok, F. B.; Ovanesyan, N. S.; Aldoshin, S. M.

    2013-06-01

    New tetranitrosyl binuclear iron complex [Fe2(SС7H5N4)2(NO)4] (I) has been synthesized by interaction of aqueous solutions of anionic salts [Fе(S2O3)2(NO)2]3- and [SС7H5N4]-. The latter one was synthesized by reduction of bis-(1-phenyl-1H-tetrazole-5-yl) disulfide with hydrazine hydrate in ethanol at T = 25 °C. Molecular and crystalline structure of I was determined by X-ray analysis; the complex has binuclear structure of "μ-SCN" type with ˜4.02 Å between the iron atoms. Shortened О⋯О contacts (2.81 Å) between the NO groups of similar type are observed. Parameters of Mössbauer spectrum for I are: isomer shift δFe = 0.311(1) mm/s, quadrupole splitting ΔEQ = 1.044(1) mm/s, line width Γ = 0.267(1) mm/s at 85 K. From SQUID magnetometry data, the temperature and field dependences of the magnetic moment of I are well described in the frame of a simple model of binuclear iron complex with magnetic centers S1 = S2 = ½. In solution, binuclear structure of the complex remains, though the NO groups are non-equivalent. For solutions of I five-line hyperfine structure of spectrum (HFS) is observed, g-factor = 2.03. For polycrystals of I, no HFS was observed due to averaged exchange interaction between the electron spins of adjacent complexes. In polycrystals of I, the number of spins per one binuclear complex is <2, this being the evidence of antiferromagnetic exchange interaction of unpaired electrons of two iron atoms. The average number of spins in crystals (0.65) and solutions (0.55) are close. The maximum amount of NO generated by I in 1% dimethylsulfoxide (DMSO) aqueous solution is ˜13.8 nM, it halves in 8 min after decomposition starts, and reaches ˜3.8 nM in anaerobic conditions at Т = 25 °С, pH 7.0. This is due, according to quantum-chemical calculations, to the presence of a more stable Fesbnd NO bond in I than in its isostructural analog - nitrosyl iron complex with 1-methyltetrazole-5-yl (II).

  4. TFP5 prevents 1-methyl-4-phenyl pyridine ion-induced neurotoxicity in mouse cortical neurons

    PubMed Central

    Zhang, Qi-Shan; Liao, Yuan-Gao; Ji, Zhong; Gu, Yong; Jiang, Hai-Shan; Xie, Zuo-Shan; Pan, Su-Yue; Hu, Ya-Fang

    2016-01-01

    The present study aimed to investigate the protective effect of a modified p5 peptide, TFP5, on 1-methyl-4-phenyl pyridine ion (MPP+)-induced neurotoxicity in cortical neurons and explore the therapeutic effect of TFP5 on Parkinson's disease (PD). MPP+ was applied to a primary culture of mouse cortical neurons to establish the cell model of PD. Neurons were divided into four groups: Control, model (MPP+), scrambled peptide (Scb) (Scb + MPP+) and TFP5 (TFP5 + MPP+) groups. Pretreatment with Scb or TFP5 was applied to the latter two groups, respectively, for 3 h, while phosphate-buffered saline was applied to the control and model groups. MPP+ was then applied to all groups, with the exception of the control group, and neurons were cultured for an additional 24 h. Neuron viability was evaluated using a Cell Counting kit-8 (CCK8) assay. To explore the mechanism underlying the protective effects of TFP5, the expression levels of p35, p25 and phosphorylated myocyte enhancer factor 2 (p-MEF2D) were determined by western blotting. Fluorescence microscopy showed that TFP5 was able to pass through cell membranes and distribute around the nucleus. CCK8 assay showed that neuronal apoptosis was dependent on MPP+ concentration and exposure time. Cell viability decreased significantly in the model group compared with the control group (55±7 vs. 100±0%; P<0.01), and increased significantly in the TFP5 group compared with the model group (98±2 vs. 55±5%; P<0.01) and Scb group (98±2 vs. 54±4%; P<0.01). Scb exhibited no protective effect. Western blotting results showed that MPP+ induced p25 and p-MEF2D expression, TFP5 and Scb did not affect MPP+-induced p25 expression, but TFP5 reduced MPP+-induced p-MEF2D expression. In summary, TFP5 protects against MPP+-induced neurotoxicity in mouse cortical neurons, possibly through inhibiting the MPP+-induced formation and elevated kinase activity of a cyclin-dependent kinase 5/p25 complex. PMID:27698762

  5. Crystal structure of {(E)-2-[(phenyl-imino)-meth-yl]phenolato-κ(2) N,O}bis-[2-(pyridin-2-yl)phenyl-κ(2) C (1),N]iridium(III) di-chloro-methane monosolvate.

    PubMed

    Goo, Moo-Sung; Park, Ki-Min; Kim, Hee-Joon

    2016-06-01

    In the title compound, [Ir(C11H8N)2(C13H10NO)]·CH2Cl2, the Ir(III) ion is six-coordinated by two C,N-bidentate 2-(pyridin-2-yl)phenyl ligands and one N,O-bidentate 2-[(phenyl-imino)-meth-yl]phenolate anion, giving rise to a distorted octa-hedral environment. The C,N-bidentate ligands, in which the C and N atoms are statistically disordered over two sites and therefore both pairs of C and N atoms are trans and cis relative to each other, are almost perpendicular to each other [the dihedral angle between the least-square planes is 87.00 (4)°]. An intra-molecular C-H⋯O hydrogen bond, as well as inter-molecular C-H⋯π inter-actions and π-π inter-actions, contribute to the stabilization of the mol-ecular and crystal structure.

  6. Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

    NASA Astrophysics Data System (ADS)

    Obasi, L. N.; Kaior, G. U.; Rhyman, L.; Alswaidan, Ibrahim A.; Fun, Hoong-Kun; Ramasami, P.

    2016-09-01

    The Schiff base, 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (TPMC/AAP) was synthesized by the condensation of 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and trans-para-methoxycinnamaldehyde (trans-3,4-methoxyphenyl-2-propenal) in dry methanol at 75 °C. The compound was characterized using elemental microanalysis, IR, NMR, UV spectroscopies and single-crystal X-ray crystallography. The X-ray structure determination shows that the Schiff base, (TPMC/AAP) is orthorhombic with the Pbca space group. The anti-microbial screening of the compound was carried out with Escherichia coli, Bacillus subtillis, Staphylococcus aureus, Pseudemonas aeruginosa, Candida albicans and Aspergillus niger using agar well diffusion method. The Schiff base possesses significant antimicrobial activity. The minimum inhibitory concentration (MIC) of the compound was also determined and the activity was compared with that of conventional drugs ciprofloxacin and ketoconazole. The compound (TPMC/AAP) showed varying activity against the cultured bacteria and fungi used. To complement the experimental data, density functional theory (DFT) was used to have deeper understanding into the molecular parameters and infrared spectra of the compound.

  7. 3-(1,3-Di­phenyl­propan-2-yl)-4-methyl-6-phenyl­isoxazolo[3,4-d]pyridazin-7(6H)-one

    PubMed Central

    Campana, Charles F.; Mirzaei, Joseph; Koerner, Chris; Gates, Christina; Natale, Nicholas R.

    2013-01-01

    In the title compound, C27H23N3O2, the geminal benzyl groups branching out from the methine adjacent to the isoxazole group are both syn-oriented to the methyl group of the pyridazinone moiety, as reflected by C—C distances of 3.812 (2) and 4.369 (2) Å between the methyl carbon and the nearest ring carbon of each benzyl group. This kind of conformation is retained in CDCl3 solution, as evidenced by distinct phenyl-shielding effects on the 1H NMR signals of the methyl H atoms. The isoxazolo[3,4-d]pyridazin ring system is virtually planar (r.m.s. deviation from planarity = 0.031 Å), but the N-bonded phenyl group is inclined to the former by an ring–ring angle of 55.05 (3)°. In the crystal, the T-shaped mol­ecules are arranged in an inter­locked fashion, forming rod-like assemblies along [10-1]. The mol­ecules are held together by unremarkable weak C—H⋯N, C—H⋯O and C—H⋯π inter­actions (C—O,N,C > 3.4 A), while significant π–π-stacking inter­actions are absent. PMID:24454112

  8. Important role of molecular packing and intermolecular interactions in two polymorphs of (Z)-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile. Preparation, structures, and optical properties

    NASA Astrophysics Data System (ADS)

    Percino, M. Judith; Cerón, Margarita; Ceballos, Paulina; Soriano-Moro, Guillermo; Castro, M. Eugenia; Chapela, Víctor M.; Bonilla-Cruz, José; Reyes-Reyes, Marisol; López-Sandoval, Román; Siegler, Maxime A.

    2014-12-01

    The novel compound Z-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile (PPyPAN) was synthesized from the condensation reaction between phenylacetonitrile and 4-(pyridin-2-yl)benzaldehyde. This compound crystallizes in two forms: polymorph I (triclinic, P - 1, Z‧ = 2) and polymorph II (orthorhombic, Pbc21, Z‧ = 2). The molecular structures and optical properties of the two polymorphs have been characterized via1H NMR, EI, FTIR, UV-Vis spectroscopy, DSC, single-crystal and XRPD. The molecular structure, packing properties, and intermolecular interactions were examined for both polymorphs of PPyPAN in order to interpret the emission properties. A subtle change in the molecular conformation (e.g., a rotation around single Csbnd C bonds) found for both polymorph plays an important role in their solid-state properties. The structure and optical properties of the new structures were well characterized and showed unique features for both polymorphic phases. For phase I, we observed an excitation spectrum with an λex at 325-346 nm, which is the maximum excitation or absorption wavelength for the lowest So → S1 transition, which is characteristic to the π-π* transition, and an emission spectrum with an λemmax at 454 nm. For phase II, the excitation spectrum showed an λexmax at 325 nm, whereas the λemmax showed a red-shift to 492 nm.

  9. Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione.

    PubMed

    Sahani, M K; Yadava, U; Pandey, O P; Sengupta, S K

    2014-05-05

    A new class of oxovanadium(IV) complexes with Schiff bases derived by the condensation of 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazoles and indoline-2,3-dione have been prepared in ethanol in the presence of sodium acetate. Micro-analytical data, magnetic susceptibility, UV-Vis, IR, EPR and XRD spectral techniques were used to confirm the structures. Electronic absorption spectra of the complexes suggest a square-pyramidal geometry. The oxovanadium(IV) complexes have monoclinic crystal system and particle sizes were found to be in the range 18.0 nm to 24.0 nm (nano-size). In vitro antifungal activity of synthesized compounds was determined against fungi Aspergillus niger, Colletotrichum falcatum and Colletotrichum pallescence and in vitro antibacterial activity was determined by screening the compounds against Gram-negative (Escherichia coli and Salmonella typhi) and Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacterial strains. The oxovanadium(IV) complexes have higher antimicrobial effect than free ligands.

  10. Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione

    NASA Astrophysics Data System (ADS)

    Sahani, M. K.; Yadava, U.; Pandey, O. P.; Sengupta, S. K.

    A new class of oxovanadium(IV) complexes with Schiff bases derived by the condensation of 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazoles and indoline-2,3-dione have been prepared in ethanol in the presence of sodium acetate. Micro-analytical data, magnetic susceptibility, UV-Vis, IR, EPR and XRD spectral techniques were used to confirm the structures. Electronic absorption spectra of the complexes suggest a square-pyramidal geometry. The oxovanadium(IV) complexes have monoclinic crystal system and particle sizes were found to be in the range 18.0 nm to 24.0 nm (nano-size). In vitro antifungal activity of synthesized compounds was determined against fungi Aspergillus niger, Colletotrichum falcatum and Colletotrichum pallescence and in vitro antibacterial activity was determined by screening the compounds against Gram-negative (Escherichia coli and Salmonella typhi) and Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacterial strains. The oxovanadium(IV) complexes have higher antimicrobial effect than free ligands.

  11. 1-Ethyl-2-phenyl-3-[2-(tri­methyl­sil­yl)ethyn­yl]-1H-indole

    PubMed Central

    Baglai, Iaroslav; Maraval, Valérie; Duhayon, Carine; Chauvin, Remi

    2013-01-01

    The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with tri­methyl­silyl­acetyl­ene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C—H⋯π inter­actions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the tri­methyl­silyl unit are equally disordered over two sets of sites. PMID:23795091

  12. (η6-Benzophenone)(η5-penta­methyl­cyclo­penta­dien­yl)ruthenium(II) tetra­phenyl­borate

    PubMed Central

    Loughrey, Bradley T.; Nadin, Kevin; Williams, Michael L.; Healy, Peter C.

    2009-01-01

    The structure of the title compound, [Ru(C10H15)(C13H10O)](C24H20B), consists of discrete [Cp*Ru(II)benzophenone] cations and tetra­phenyl­borate anions (Cp* = penta­methyl­cyclo­penta­dien­yl). Tethering the Cp*Ru group to one aryl ring of benzophenone results in average values of 1.42 (1) and 1.38 (1) Å for the C—C bond lengths in the Ru-tethered and untethered phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings of the benzophenone group is 50.5 (1)°. PMID:21578208

  13. 1,4-Dimethyl-3-phenyl-3H-pyrazolo[3,4-c]isoquinolin-5(4H)-one.

    PubMed

    Meneghetti, Fiorella; Bombieri, Gabriella; Maggio, Benedetta; Daidone, Giuseppe

    2008-04-16

    The title compound, C(18)H(15)N(3)O, is the product of the thermal decomposition of the diazo-nium salt derived from 2-amino-N-methyl-N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)benzamide. It is characterized by a trans orientation of the methyl groups with respect to the tricyclic ring system. The mol-ecule has a nearly planar phenyl-pyrazolo[3,4-c]isoquinolin-5-one system, the largest deviation from the mean plane being 0.066 (2) Å for the O atom. The dihedral angle between the phenyl substituent and the heterotricycle is 67 (1)°. The packing is stabilized by C-H⋯N hydrogen-bond inter-actions, with the formation of mol-ecular chains along the c axis.

  14. 3-(4-Chloro­phen­yl)-5-phenyl-4,5-di­hydro-1,3-oxazole

    PubMed Central

    Islor, Arun M.; Yaradoni, Rajiv; Garudachari, B.; Gerber, Thomas; Hosten, Eric; Betz, Richard

    2012-01-01

    In the title compound, C15H12ClNO, the isoxazoline ring adopts an envelope conformation with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16 (7)°. The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93 (7)°. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯π inter­actions connect the mol­ecules into layers perpendicular to the a axis. PMID:23284521

  15. Copper(II) and nickel(II) complexes of benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone: Synthesis, characterization and biological activity

    NASA Astrophysics Data System (ADS)

    Prathima, B.; Subba Rao, Y.; Adinarayana Reddy, S.; Reddy, Y. P.; Varada Reddy, A.

    2010-09-01

    Benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone ligand (L) has been synthesized from benzyloxybenzaldehyde and 4-phenyl-3-thiosemicarbazide. Complexes of this ligand with chlorides of Cu(II) and Ni(II) have been prepared. The structure of the ligand (L) is proposed based on elemental analysis, IR and 1H NMR spectra. Its complexes with Cu(II) and Ni(II) ions are characterized from the studies of electronic as well as EPR spectra. On the basis of electronic and EPR studies, rhombically distorted octahedral structure has been proposed for Cu(II) complex while the Ni(II) complex has been found to acquire an octahedral structure. The ligand and their metal complexes have been tested in vitro for their biological effects. Their antibacterial activities against Gram-negative bacteria ( Escherichia coli and Klebsiella pneumoniae) and Gram-positive bacteria ( Staphylococcus aureus and Bacillus subtilis) have been investigated. The prepared metal complexes exhibit higher antibacterial activities than the parent ligand. The in vitro antioxidant activity of free ligand and its metal(II) complexes have also been investigated and the results however reveal that the ligand exhibits greater antioxidant activity than its complexes.

  16. Crystal structure of 5-tert-but­yl-10,15,20-tri­phenyl­porphyrin

    PubMed Central

    Flanagan, Keith J.; Mothi, Ebrahim Mohamed; Kötzner, Lisa; Senge, Mathias O.

    2016-01-01

    In the title free base porphyrin, C42H34N4, the neighbouring N⋯N distances in the center of the ring vary from 2.818 (8) to 2.998 (8) Å and the phenyl rings are tilted from the 24-atom mean plane at angles varying between 62.42 (2)–71.63 (2)°. The NH groups are involved in intra­molecular bifurcated N—H⋯(N,N) hydrogen bonds. The Ca—Cm—Ca angles vary slightly for the phenyl rings, between 124.19 (18)–126.17 (18)°. The largest deviation from the mean plane of the 24-atom macrocycle is associated with the meso carbon at the substituted tert-butyl position, which is displaced from the mean plane by 0.44 (2) Å. The free base porphyrin is characterized by a significant degree of ruffled (B 1u) distortion with contributions from domed (A 2u) and wave [Eg(y) and Eg(x)] modes. In the crystal, mol­ecules are linked by a number of weak C—H⋯π inter­actions, forming a three-dimensional framework. The structure was refined as a two-component inversion twin. PMID:26958370

  17. Assessing Cholesterol Storage in Live Cells and C. elegans by Stimulated Raman Scattering Imaging of Phenyl-Diyne Cholesterol

    NASA Astrophysics Data System (ADS)

    Lee, Hyeon Jeong; Zhang, Wandi; Zhang, Delong; Yang, Yang; Liu, Bin; Barker, Eric L.; Buhman, Kimberly K.; Slipchenko, Lyudmila V.; Dai, Mingji; Cheng, Ji-Xin

    2015-01-01

    We report a cholesterol imaging method using rationally synthesized phenyl-diyne cholesterol (PhDY-Chol) and stimulated Raman scattering (SRS) microscope. The phenyl-diyne group is biologically inert and provides a Raman scattering cross section that is 88 times larger than the endogenous C = O stretching mode. SRS microscopy offers an imaging speed that is faster than spontaneous Raman microscopy by three orders of magnitude, and a detection sensitivity of 31 μM PhDY-Chol (~1,800 molecules in the excitation volume). Inside living CHO cells, PhDY-Chol mimics the behavior of cholesterol, including membrane incorporation and esterification. In a cellular model of Niemann-Pick type C disease, PhDY-Chol reflects the lysosomal accumulation of cholesterol, and shows relocation to lipid droplets after HPβCD treatment. In live C. elegans, PhDY-Chol mimics cholesterol uptake by intestinal cells and reflects cholesterol storage. Together, our work demonstrates an enabling platform for study of cholesterol storage and trafficking in living cells and vital organisms.

  18. Aminobenzoic acid diuretics. 7. 3-Substituted 4-phenyl-, 4-arylcarbonyl-, and 4-arylmethyl-5-sulfamoylbenzoic acids and related compounds.

    PubMed

    Nielsen, O B; Bruun, H; Bretting, C; Feit, P W

    1975-01-01

    Various 4-substituted 3-alkylamino-, 3-alkoxy-, 3-alkylthio-, and 3-alkyl-5-sulfamoylbenzoic acids related to known aminobenzoic acid diuretics were synthesized and screened for their diuretic properties in dogs. The tabulated results from a 3-hr test period revealed that generally the diuretic profile and potency could be retained when 3-alkoxy, 3-alkylthio, and 3-phenethyl were substituted for the 3-alkylamino moiety. The high potency of several 3-alkoxy-, 3-alkylthio-, and 3-phenethyl-4-benzoyl-5-sulfamoylbenzoic acids confirmed previous suggestions that the apparent diuretic effect of 4- and 5-alkylamino-6-carboxy-3-phenyl-1,2-benzisothiazole 1,1-dioxides originates from the corresponding 4-benzoyl-5-sulfamoylbenzoic acid derivatives due to an existing equilibrium in plasma. 4-Benzoyl-5-sulfamoyl-3-(3-thenyloxy) benzoic acid (118) is among the most potent benzoic acid diuretics hitherto synthesized and shows significant diuretic activity in dogs at 1 mug/kg. The results obtained with different 3-substituted 4-phenyl-5-sulfamoylbenzoic acids supported the earlier concept regarding the steric influence of the 4-substituent on the diuretic potency of sulfamoylbenzoic acid diuretics.

  19. Experimental and theoretical study of 2,5-diaryloxazoles whose aryl are para-substituted phenyl groups

    NASA Astrophysics Data System (ADS)

    Ionescu, Sorana; Popovici, Daniela; Balaban, Alexandru T.; Hillebrand, Mihaela

    2005-11-01

    Absorption and emission properties of some phenoxy derivatives of diphenyloxazole (PPO) are presented and discussed. The photophysical properties reflect a dependence on the substituted 2 or 5 position of the oxazole ring. The experimental data were correlated with molecular parameters such as molecular flexibility, electronic structure and the singlet-triplet gap. The substitution with heteroatomic-bridged phenyls maintains the same frontier orbitals ( m, m + 1) as in the parent compound, but introduces a new molecular orbital, m - 1, located on the terminal phenyl. The presence of the so-called band B in the absorption spectra of some diaryloxazoles was attributed to the m - 1 → m + 1 transition participating to the second excited state wave function. The other main component of this state, the m → m + 2 transition, was found to have a forbidden character, explaining the lack or the low intensity of band B. The decrease of the fluorescence quantum yield subsequent to substitution of PPO with phenoxy fragments was found to be due to the enhanced molecular flexibility comparing to PPO. The differences between the 2- or 5-substituted derivatives were rationalized in terms of a smaller S 1-T 2 gap for the former, thus increasing the rate of the overall nonradiative intersystem crossing processes.

  20. Synthesis and bioevaluation of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acids as potent xanthine oxidase inhibitors.

    PubMed

    Guan, Qi; Cheng, Zengjin; Ma, Xiaoxue; Wang, Lijie; Feng, Dongjie; Cui, Yuanhang; Bao, Kai; Wu, Lan; Zhang, Weige

    2014-10-06

    A series of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acid derivatives (8a-f, 9a-m) were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Structure-activity relationship analyses have also been presented. Most of the target compounds exhibited potency levels in the nanomolar range. Compound 9e emerged as the most potent xanthine oxidase inhibitor (IC50 = 5.5 nM) in comparison to febuxostat (IC50 = 18.6 nM). Steady-state kinetics measurements with the bovine milk enzyme indicated a mixed type inhibition with Ki and Ki' values of 0.9 and 2.3 nM, respectively. A molecular modeling study on compounds 9e was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acid scaffold.

  1. SKF-38393, a dopamine receptor agonist, attenuates 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity.

    PubMed

    Muralikrishnan, D; Ebadi, M

    2001-02-23

    Parkinson's disease (PD) is characterized by progressive degeneration of nigrostriatal dopaminergic neurons. Several factors such as inhibition of the mitochondrial respiration, generation of hydroxyl radicals and reduced free radical defense mechanisms causing oxidative stress, have been postulated to contribute to the degeneration of dopaminergic neurons. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) treated animals is a useful experimental model of PD, exhibiting most of the clinical features, as well as the main biochemical and pathologic symptoms of the disease. In the present study, we have examined a dopaminergic (D1) receptor agonist, SKF-38393 HCl (SKF) for its possible neuroprotective action against MPTP-induced insults on dopaminergic neurons. MPTP is converted by monoamine oxidase-B (MAO-B) to its neurotoxic metabolite 1-methyl-4-phenyl-pyridinium (MPP+), which is then taken up into the dopaminergic neurons. SKF-38393 had no effects either on total or monoamine oxidase B in the striatum. SKF-38393 blocked the MPTP-induced depletion of glutathione and attenuated MPTP-induced depletion of dopamine. Furthermore, it enhanced the activity of superoxide dismutase and hence mimicked the action of selegiline. The results of these studies are interpreted to suggest that SKF-38393 may prove a valuable drug in the treatment of Parkinson's disease.

  2. A new high phenyl lactic acid-yielding Lactobacillus plantarum IMAU10124 and a comparative analysis of lactate dehydrogenase gene.

    PubMed

    Zhang, Xiqing; Zhang, Shuli; Shi, Yan; Shen, Fadi; Wang, Haikuan

    2014-07-01

    Phenyl lactic acid (PLA) has been widely reported as a new natural antimicrobial compound. In this study, 120 Lactobacillus plantarum strains were demonstrated to produce PLA using high-performance liquid chromatography. Lactobacillus plantarum IMAU10124 was screened with a PLA yield of 0.229 g L(-1) . Compared with all previous reports, this is the highest PLA-producing lactic acid bacteria (LAB) when grown in MRS broth without any optimizing conditions. When 3.0 g L(-1) phenyl pyruvic acid (PPA) was added to the medium as substrate, PLA production reached 2.90 g L(-1) , with the highest 96.05% conversion rate. A lowest PLA-yielding L. plantarum IMAU40105 (0.043 g L(-1) ) was also screened. It was shown that the conversion from PPA to PLA by lactic dehydrogenase (LDH) is the key factor in the improvement of PLA production by LAB. Comparing the LDH gene of two strains, four amino acid mutation sites were found in this study in the LDH of L. plantarum IMAU10124.

  3. Copper(II) and nickel(II) complexes of benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone: Synthesis, characterization and biological activity.

    PubMed

    Prathima, B; Subba Rao, Y; Adinarayana Reddy, S; Reddy, Y P; Varada Reddy, A

    2010-09-15

    Benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone ligand (L) has been synthesized from benzyloxybenzaldehyde and 4-phenyl-3-thiosemicarbazide. Complexes of this ligand with chlorides of Cu(II) and Ni(II) have been prepared. The structure of the ligand (L) is proposed based on elemental analysis, IR and (1)H NMR spectra. Its complexes with Cu(II) and Ni(II) ions are characterized from the studies of electronic as well as EPR spectra. On the basis of electronic and EPR studies, rhombically distorted octahedral structure has been proposed for Cu(II) complex while the Ni(II) complex has been found to acquire an octahedral structure. The ligand and their metal complexes have been tested in vitro for their biological effects. Their antibacterial activities against Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) and Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) have been investigated. The prepared metal complexes exhibit higher antibacterial activities than the parent ligand. The in vitro antioxidant activity of free ligand and its metal(II) complexes have also been investigated and the results however reveal that the ligand exhibits greater antioxidant activity than its complexes.

  4. Interactions of the neurotoxic amine 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine with monoamine oxidases.

    PubMed

    Singer, T P; Salach, J I; Castagnoli, N; Trevor, A

    1986-05-01

    1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), a thermal breakdown product of a meperidine-like narcotic used by drug abusers as a heroin substitute, produces Parkinsonian symptoms in humans and primates. The nigrostriatal toxicity is not due to MPTP itself but to one or more oxidation products resulting from the action of monoamine oxidase (MAO) on this tertiary allylamine. Both MAO A and B catalyse the oxidation of MPTP to the 1-methyl-4-phenyl-2,3-dihydropyridinium species (MPDP+), which undergoes further oxidation to the fully aromatic 1-methyl-4-phenylpyridinium species (MPP+). These bio-oxidations are blocked by selective inhibitors of MAO A and B. Additionally, MPTP, MPDP+ and MPP+ are competitive inhibitors of MAO A and B. The A form of the enzyme is particularly sensitive to this type of reversible inhibition. Both MAO A and B also are irreversibly inactivated by MPTP and MPDP+, but not by MPP+. This inactivation obeys the characteristics of a mechanism-based or 'suicide' process. The inactivation, which is accompanied by the incorporation of radioactivity from methyl-labelled MPTP, is likely to result from covalent modification of the enzyme.

  5. Synthesis and COX-2 Inhibitory Activity of 4-[(E)-2-(4-Oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethenyl]benzene-1-sulfonamideand Its Analogs

    PubMed Central

    Hayun; Hudiyono, Sumi; Hanafi, Muhammad; Yanuar, Arry

    2012-01-01

    Some novel 3-phenyl-2-[(E)-2-phenylethenyl]-3,4-dihydroquinazolin-4-one derivatives possessing para-sulfonamides groups on the phenyl ring of the 2-phenylethenyl moiety have been synthesized and their COX-2 inhibitory activity evaluated. The stuctures of the synthesized compounds were confirmed on the basis of FT-IR, 1H-NMR, 13C-NMR and mass spectral data. The COX-2 inhibition screening assay revealed that 4-[(E)-2-{3-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl}ethenyl]benzene-1-sulfonamide had a maximum COX-2 inhibition (47.1%), at a concentration of 20 μM. PMID:24281337

  6. Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans.

    PubMed

    Wang, Shihua; Li, Pinhua; Yu, Lin; Wang, Lei

    2011-11-18

    Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.

  7. 2-(2-Fluoro­phen­yl)-3-methyl­sulfanyl-5-phenyl-1-benzo­furan

    PubMed Central

    Choi, Hong Dae; Seo, Pil Ja; Lee, Uk

    2013-01-01

    In the title compound, C21H15FOS, the dihedral angles between the mean plane [r.m.s. deviation = 0.041 (1) Å] of the benzo­furan fragment and the pendant 2-fluoro­phenyl and phenyl rings are 46.09 (3) and 24.34 (5)°, respectively. In the crystal, mol­ecules are linked by weak C—H⋯π inter­actions, forming a three-dimensional network. PMID:23723873

  8. Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-phenyl-3-substituted quinazolin-4(3H) ones.

    PubMed

    Alagarsamy, Veerachamy; Salomon, Viswas Raja; Vanikavitha, Gnanavel; Paluchamy, Veeran; Chandran, Muniyandi Ravi; Sujin, Augustin Arnald; Thangathiruppathy, Arunachalam; Amuthalakshmi, Sivaperuman; Revathi, Rajappan

    2002-11-01

    A series of novel 2-phenyl-3-substituted quinazolin-4(3H)-ones have been synthesized by treating methyl-N-(2-phenyl quinazolin-3-yl-4(3H)-one) dithiocarbamate with different amines, the starting material dithiocarbamate was synthesized from anthranilic acid. The title compounds were investigated for analgesic, anti-inflammatory and antibacterial activities. All the test compounds exhibited significant activity, the compounds A1, A2 and A3 shown more potent analgesic activity, and the compound A3 shown more potent anti-inflammatory activity than the reference standard diclofenac sodium.

  9. Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.

    PubMed

    Das, Bhaskar C; Mohapatra, Seetaram; Campbell, Philip D; Nayak, Sabita; Mahalingam, Sakkarapalayam M; Evans, Todd

    2010-05-01

    Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets.

  10. Thermal Studies of Zn(II), Cd(II) and Hg(II) Complexes of Some N-Alkyl-N-Phenyl-Dithiocarbamates

    PubMed Central

    Onwudiwe, Damian C.; Ajibade, Peter A.

    2012-01-01

    The thermal decomposition of Zn(II), Cd(II) and Hg(II) complexes of N-ethyl-N-phenyl and N-butyl-N-phenyl dithiocarbamates have been studied using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The products of the decomposition, at two different temperatures, were further characterized by scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDX). The results show that while the zinc and cadmium complexes undergo decomposition to form metal sulphides, and further undergo oxidation forming metal oxides as final products, the mercury complexes gave unstable volatiles as the final product. PMID:22949811

  11. 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as orphanin FQ receptor agonists.

    PubMed

    Wichmann, J; Adam, G; Röver, S; Cesura, A M; Dautzenberg, F M; Jenck, F

    1999-08-16

    A series of 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan+ ++-4-one derivatives 1 was studied with respect to the binding affinity for the orphanin FQ (OFQ) and opioid (mu, kappa, delta) receptors. The influence of stereochemistry as well as the substitution pattern of the phenyl-ring in position 1 on the affinity for the orphanin FQ receptor and selectivity to opioid (mu, kappa, delta) receptors is discussed. The most interesting compound 1c was tested for its anxiolytic-like properties in vivo.

  12. Intramolecular general acid catalysis of the hydrolysis of 2-(2'-imidazolium)phenyl phosphate, and bond length-reactivity correlations for reactions of phosphate monoester monoanions.

    PubMed

    Brandão, Tiago A S; Orth, Elisa S; Rocha, Willian R; Bortoluzzi, Adailton J; Bunton, Clifford A; Nome, Faruk

    2007-05-11

    Rate constants for the hydrolysis of 2-(2'-imidazolium)phenyl hydrogen phosphate (IMPP) in water at pH<6 indicate that activation by the imidazolium moiety disappears with the deprotonation of the phosphate group, and the reaction involves the hydrogen-bonding of the imidazolium NH with the aryl oxygen leaving group. The reaction should involve a near-planar conformation of the imidazolium and the phenyl groups in the activated complex, which favors proton-transfer. The crystal structure of IMPP was solved, and a bond length-reactivity correlation for reactions of phosphate monoester monoanions is described.

  13. Synthesis and biological evaluation of substituted 2-phenyl-2H-indazole-7-carboxamides as potent poly(ADP-ribose) polymerase (PARP) inhibitors.

    PubMed

    Scarpelli, Rita; Boueres, Julia K; Cerretani, Mauro; Ferrigno, Federica; Ontoria, Jesus M; Rowley, Michael; Schultz-Fademrecht, Carsten; Toniatti, Carlo; Jones, Philip

    2010-01-15

    A potent series of substituted 2-phenyl-2H-indazole-7-carboxamides were synthesized and evaluated as inhibitors of poly (ADP-ribose) polymerase (PARP). This extensive SAR exploration culminated with the identification of substituted 5-fluoro-2-phenyl-2H-indazole-7-carboxamide analog 48 which displayed excellent PARP enzyme inhibition with IC(50)=4nM, inhibited proliferation of cancer cell lines deficient in BRCA-1 with CC(50)=42nM and showed encouraging pharmacokinetic properties in rats compared to the lead 6.

  14. Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1H-phenalen-1-one: a functional group exclusion approach.

    PubMed

    Duque, Luisa; Zapata, Carolina; Rojano, Benjamín; Schneider, Bernd; Otálvaro, Felipe

    2013-07-19

    2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elata, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore the effect of each functional group. H-Atom transfer from the phenolic hydroxyl, a captodative effect from the hydroxy ketone, and the presumed involvement of the phenyl ring in the termination step of the radical reaction were disclosed as relevant features of this type of antioxidant.

  15. 2,5-disubstituted oxazole research: fluorescence quantum yields and laser conversion efficiencies of 2-(p-italic-biphenyl)-5-phenyl oxazole and its 5-p-italic-substituted derivatives

    SciTech Connect

    Yu Peifeng

    1986-03-01

    The fluorescence quantum yield and laser conversion efficiency of 2-(p-italic-biphenyl)-5-phenyl-oxazole and thirteen 5-substituted phenyl derivatives are measured. A brief discussion is also given on the relation between the subtituent effects and spectral properties of the compounds.

  16. Homo-C-nucleoside analogs III. Studies on the base-catalyzed dehydrative cyclization of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole.

    PubMed

    Sallam, Mohammed A E

    2010-10-13

    Treatment of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole with one molar equivalent of 2,4,6-triisopropylbenzenesulfonyl chloride (TIBSCl) in pyridine solution afforded the homo-C-nucleoside analog; 4-(2,5-anhydro-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole in 54% yield and 4-(α-d-arabinopyranosyl)-2-phenyl-2H1,2,3-triazole analog in 3% yield. The 4-(5-O-triisopropylbenzenesulfonyl)-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole analog was isolated as an intermediate and identified as its tetra-O-acetyl derivative. The 4-(5-chloro-5-deoxy-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole analog was isolated as a byproduct. The structure and anomeric configuration of the products were determined by acylation, NMR spectroscopy, and mass spectrometry.

  17. Optimization of Phenyl-Substituted Benzimidazole Carboxamide Poly(ADP-Ribose) Polymerase Inhibitors: Identification of (S)-2-(2-Fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (A-966492), a Highly Potent and Efficacious Inhibitor

    SciTech Connect

    Penning, Thomas D.; Zhu, Gui-Dong; Gong, Jianchun; Thomas, Sheela; Gandhi, Viraj B.; Liu, Xuesong; Shi, Yan; Klinghofer, Vered; Johnson, Eric F.; Park, Chang H.; Fry, Elizabeth H.; Donawho, Cherrie K.; Frost, David J.; Buchanan, Fritz G.; Bukofzer, Gail T.; Rodriguez, Luis E.; Bontcheva-Diaz, Velitchka; Bouska, Jennifer J.; Osterling, Donald J.; Olson, Amanda M.; Marsh, Kennan C.; Luo, Yan; Giranda, Vincent L.

    2010-06-21

    We have developed a series of phenylpyrrolidine- and phenylpiperidine-substituted benzimidazole carboxamide poly(ADP-ribose) polymerase (PARP) inhibitors with excellent PARP enzyme potency as well as single-digit nanomolar cellular potency. These efforts led to the identification of (S)-2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (22b, A-966492). Compound 22b displayed excellent potency against the PARP-1 enzyme with a K{sub i} of 1 nM and an EC{sub 50} of 1 nM in a whole cell assay. In addition, 22b is orally bioavailable across multiple species, crosses the blood-brain barrier, and appears to distribute into tumor tissue. It also demonstrated good in vivo efficacy in a B16F10 subcutaneous murine melanoma model in combination with temozolomide and in an MX-1 breast cancer xenograft model both as a single agent and in combination with carboplatin.

  18. Crystal structure of 1-phenyl­imido-1-{6-[1-(phenyl­imino)­eth­yl]pyridin-2-yl}ethan-1-yl-κ3 N,N′,N′′)iron(II)

    PubMed Central

    Lau, Ka-Cheong; Filatov, Alexander S.; Jordan, Richard F.

    2016-01-01

    The title iron complex, [Fe(C21H19N3)2], consists of an FeII atom chelated by two tridentate bis­(imino)­pyridine radical anions in a slightly distorted octa­hedral coordination environment. In the solid state, there are two independent half-mol­ecules in the asymmetric unit, and the complete mol­ecular structure is formed by applying twofold rotation symmetry with the twofold rotation axis passing through an Fe atom. In the crystal, the Fe-containing complexes are not involved in any particular direct inter­molecular inter­actions, with the shortest C—HAr contacts between neighboring phenyl groups being ca 3.2 Å. PMID:27840716

  19. Reactivity of N-Phenyl-1-Aza-2-Cyano-1,3-Butadienes in the Diels-Alder Reaction.

    PubMed

    Sisti, Nicholas J.; Motorina, Irina A.; Tran Huu Dau, Marie-Elise; Riche, Claude; Fowler, Frank W.; Grierson, David S.

    1996-05-31

    It is found that N-phenyl-2-cyano-1-azadiene 4, prepared via a two-step, one-pot, sequence from acrylanilide, undergoes efficient [4 + 2] cycloaddition with a complete range of electron rich, electron poor, and neutral dienophiles under remarkably mild thermal conditions (90-120 degrees C for 20-48 h). Regiospecific formation of the alpha-cycloadduct wherein the dienophile substituent is alpha to nitrogen is observed for vinyl ethers and styrene, whereas the Diels-Alder reactions with methyl acrylate and methyl vinyl ketone (MVK) produce alpha/beta mixtures in which the alpha-cycloadduct is the major regioisomer (approximately 4-5:1). An essentially identical reaction pattern was observed in the Diels-Alder reaction of N-(p-methoxyphenyl)-2-cyano-1-azadiene 18 and the 4-methyl-substituted azadiene 27. For compound 19 derived from cycloaddition of 18 with ethyl vinyl ether, facile conversion to the dihydropyridine 21 through loss of EtOH on brief acid treatment was also noted. The 2,4-cis-disubstitution pattern confirmed by X-ray diffraction for the major cycloadduct 29 isolated from the reaction of 27 with styrene provides evidence for the endo mode of cycloaddition in the Diels-Alder reaction of N-phenyl(aryl)-2-cyano-1-azadienes. Calculation of the frontier orbital energies and coefficients, as well as the transition state geometries for the [4 + 2] cycloaddition of N-phenyl-2-cyano-1-azadiene 4 with methyl vinyl ether, styrene, and MVK were carried out at the RHF AM1 level (MOPAC, Version 5.0). The FMO treatment indicates that the reaction of 4 with methyl vinyl ether occurs under LUMO(diene) control, whereas in contrast, the corresponding cycloaddition with MVK occurs preferably under HOMO(diene) control. A high degree of asynchronicity is observed in the calculated transition states for reaction of 4 with the three representative dienophiles. In all cases the transition states leading to the alpha-cycloadducts are lower in energy than those giving the beta

  20. The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker.

    PubMed

    Marvania, Bhavin; Kakadiya, Rajesh; Christian, Wilson; Chen, Tai-Lin; Wu, Ming-Hsi; Suman, Sharda; Tala, Kiran; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long

    2014-08-18

    We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revealed that the C2-methylquinoline derivatives (18a-o) were generally more cytotoxic than the C2-phenylquinoline conjugates (23a-d) in inhibiting the cell growth of various human tumor cell lines in vitro. However, the methylamino or aniline substituents at C4 of quinoline did not influence the cytotoxic effects. The title conjugates were capable of inducing DNA cross-linking and promoting cell-cycle arrest at the G2/M phase. This study demonstrates that phenyl N-mustard-4-anilinoquinoline conjugates are generally more potent than phenyl N-mustard-4-anilinoquinazoline conjugates against the cell growth of various tumor cell-lines.

  1. 40 CFR 721.10609 - Imidodicarbonic diamide, N,N′-dibutyl-N′,2-bis[4-[(4-isocyanatophenyl)methyl]phenyl]-.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Imidodicarbonic diamide, N,Nâ²-dibutyl... New Uses for Specific Chemical Substances § 721.10609 Imidodicarbonic diamide, N,N′-dibutyl-N′,2-bis... substance identified as imidodicarbonic diamide, N,N′-dibutyl-N′,2-bis phenyl]-(PMN P-11-548; CAS...

  2. Replacement of the Bryostatin A- and B-Pyran Rings With Phenyl Rings Leads to Loss of High Affinity Binding With PKC.

    PubMed

    Petersen, Mark E; Kedei, Noemi; Lewin, Nancy E; Blumberg, Peter M; Keck, Gary E

    2016-10-19

    We describe a convergent synthesis of a bryostatin analogue in which the natural A- and B-ring pyrans have been replaced by phenyl rings. The new analogue exhibited PMA like behavior in cell assays, but failed to maintain high affinity binding for PKC, despite retaining an unaltered C-ring 'binding domain'.

  3. Trapping of benzene oxide-oxepin and methyl-substituted derivatives with 4-phenyl- and 4-pentafluorophenyl-1,2,4-triazoline-3,5-dione.

    PubMed

    Henderson, Alistair P; Mutlu, Esra; Leclercq, Amélie; Bleasdale, Christine; Clegg, William; Henderson, Richard A; Golding, Bernard T

    2002-09-07

    4-Phenyl-1,2,4-triazoline-3,5-dione and its pentafluoro analogue are efficient reagents for trapping arene oxides, e.g. benzene oxide-oxepin, affording crystalline adducts that can be quantitatively analysed by HPLC and MS techniques.

  4. 6-Allyl-8-meth­oxy-3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine

    PubMed Central

    Zhu, Jing; Ren, Zhi-Dong; Liu, Yang; Zhao, Lei; Wu, Yong

    2011-01-01

    In the title compound, C18H19NO2, the allyl group is disordered over two sets of sites [occupancy ratio 0.662 (4):0.338 (4)]. The dihedral angle between the phenyl and benzene rings is 87.44 (10)°. The oxazinane ring adopts a sofa conformation. PMID:22091082

  5. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Glycols, polyethylene-, 3-sulfo-2... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4040 Glycols, polyethylene..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  6. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Glycols, polyethylene-, 3-sulfo-2... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4040 Glycols, polyethylene..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  7. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Glycols, polyethylene-, 3-sulfo-2... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4040 Glycols, polyethylene..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  8. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Glycols, polyethylene-, 3-sulfo-2... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4040 Glycols, polyethylene..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  9. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Glycols, polyethylene-, 3-sulfo-2... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.4040 Glycols, polyethylene..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  10. Fast Hetero-Diels-Alder Reactions Using 4-Phenyl-1,2,4-Triazoline-3,5-Dione (PTAD) as the Dienophile

    ERIC Educational Resources Information Center

    Celius, Tevye C.

    2010-01-01

    A hetero-Diels-Alder reaction that proceeds rapidly and only requires a simple filtration to purify the product is presented. The dienophile, 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), is prepared by the heterogeneous oxidation of 4-phenylurazole by the bromenium ion, Br[superscript +], generated in situ by the oxidation of potassium bromide by…

  11. Effect of phenyl group on the self assembly of N,N‧-bis-(2-phenylglycinyl)pyromellitic diimide with aromatic hydrocarbons

    NASA Astrophysics Data System (ADS)

    Barooah, Nilotpal; Baruah, Jubaraj B.

    2008-01-01

    The presence of the phenyl substituent in N, N'- bis-(2-phenylglycinyl)pyromellitic diimide ( L2) facilitate the aromatic C sbnd H⋯π interactions of the guests such as anthracene and perylene and play the crucial role in directing the hydrogen bonding motif involving the carboxylic acid groups of L2.

  12. Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5-(Phenyl) pyridine or pyrazine V-Shaped molecules as kinase inhibitors and cytotoxic agents.

    PubMed

    Kassis, Pamela; Brzeszcz, Joanna; Bénéteau, Valérie; Lozach, Olivier; Meijer, Laurent; Le Guével, Rémi; Guillouzo, Christiane; Lewiński, Krzysztof; Bourg, Stéphane; Colliandre, Lionel; Routier, Sylvain; Mérour, Jean-Yves

    2011-11-01

    We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were used to generate several substitutions of the pyridine and pyrazine rings. The synthesis included Stille or Suzuki type reactions, which were carried out on the 3,5-dibromopyridine, 2,4-dichloropyridine and 2,6-dichloro-1-4-pyrazine moieties. Cell effects of the V-shaped family were in the micromolar range. Kinase assays were conducted and showed that compound 11 inhibited CDK5 with an inhibitory concentration of 160 nM with a moderate selectivity over GSK3 compared to the reference C which exhibited a slightly lower activity on CDK5 (1.5 μM). Compound 11 was also found to be the most potent compound in the series and was identified as a new lead for DYRK1A inhibitor discovery (IC(50) = 60 nM). Docking studies were carried out in order to investigate the inhibition of DYRK1A.

  13. 40 CFR 721.8940 - Chromate(3-), bis[3-[[6-amino-1,4-dihydro-2-[[[4-[(2-hydroxy-1-naphthalenyl)azo] phenyl]sulfonyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...] amino]-4-(oxo-.kappa.O)-5- pyrimidinyl]azo-.kappaN1] -4-hydroxy-.kappa.O)-5-nitrobenzenesulfonato(3... Specific Chemical Substances § 721.8940 Chromate(3-), bis phenyl]sulfonyl] amino]-4-(oxo-.kappa.O)-5- pyrimidinyl]azo-.kappaN1] -4-hydroxy-.kappa.O)-5-nitrobenzenesulfonato(3-)]-, trisodium. (a)...

  14. 40 CFR 721.8940 - Chromate(3-), bis[3-[[6-amino-1,4-dihydro-2-[[[4-[(2-hydroxy-1-naphthalenyl)azo] phenyl]sulfonyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...] amino]-4-(oxo-.kappa.O)-5- pyrimidinyl]azo-.kappaN1] -4-hydroxy-.kappa.O)-5-nitrobenzenesulfonato(3... Specific Chemical Substances § 721.8940 Chromate(3-), bis phenyl]sulfonyl] amino]-4-(oxo-.kappa.O)-5- pyrimidinyl]azo-.kappaN1] -4-hydroxy-.kappa.O)-5-nitrobenzenesulfonato(3-)]-, trisodium. (a)...

  15. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  16. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  17. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  18. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  19. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  20. Synthesis and evaluation of 3-amino/guanidine substituted phenyl oxazoles as a novel class of LSD1 inhibitors with anti-proliferative properties.

    PubMed

    Dulla, Balakrishna; Kirla, Krishna Tulasi; Rathore, Vandana; Deora, Girdhar Singh; Kavela, Sridhar; Maddika, Subbareddy; Chatti, Kiranam; Reiser, Oliver; Iqbal, Javed; Pal, Manojit

    2013-05-21

    A series of functionalized phenyl oxazole derivatives was designed, synthesized and screened in vitro for their activities against LSD1 and for effects on viability of cervical and breast cancer cells, and in vivo for effects using zebrafish embryos. These compounds are likely to act via multiple epigenetic mechanisms specific to cancer cells including LSD1 inhibition.

  1. 21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 1 2013-04-01 2013-04-01 false 4- -2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN... exceed the minimum reasonably required to accomplish the intended coloring effect. (2) Authorization...

  2. 21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 1 2012-04-01 2012-04-01 false 4- -2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN... exceed the minimum reasonably required to accomplish the intended coloring effect. (2) Authorization...

  3. Infrared spectrum, structural and optical properties and molecular docking study of 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde

    NASA Astrophysics Data System (ADS)

    Mary, Y. Sheena; Panicker, C. Yohannan; Sapnakumari, M.; Narayana, B.; Sarojini, B. K.; Al-Saadi, Abdulaziz A.; Van Alsenoy, C.; War, Javeed Ahmad; Fun, H. K.

    2015-03-01

    The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde have been investigated experimentally and theoretically. The title compound was optimized using at HF and DFT levels of calculations. The B3LYP/6-311++G(d,p) (5D,7F) results and in agreement with experimental infrared bands. The normal modes are assigned using potential energy distribution. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using natural bonding orbital analysis. The frontier molecular orbital analysis is used to determine the charge transfer within the molecule. From molecular electrostatic potential map, it is evident that the negative electrostatic potential regions are mainly localized over the carbonyl group and mono substituted phenyl ring and are possible sites for electrophilic attack and, positive regions are localized around all para substituted phenyl and pyrazole ring, indicating possible sites for nucleophilic attack. First hyperpolarizability is calculated in order to find its role in nonlinear optics. The geometrical parameters are in agreement with experimental data. From the molecular docking studies, it is evident that the fluorine atom attached to phenyl ring and the carbonyl group attached to pyrazole ring are crucial for binding and the results draw us to the conclusion that the compound might exhibit phosphodiesterase inhibitory activity.

  4. Phenyl Benzo[b]phenothiazine as a Visible Light Photoredox Catalyst for Metal-Free Atom Transfer Radical Polymerization.

    PubMed

    Dadashi-Silab, Sajjad; Pan, Xiangcheng; Matyjaszewski, Krzysztof

    2016-12-23

    This paper reports use of phenyl benzo[b]phenothiazine (Ph-benzoPTZ) as a visible light-induced metal-free atom transfer radical polymerization (ATRP) photoredox catalyst. Well-controlled polymerizations of various methacrylate monomers were conducted under a 392 nm visible light LED using Ph-benzoPTZ to activate different alkyl halides. The use of the photocatalyst enabled temporal control over the growth of polymer chains during intermittent on/off periods. The polymerization was initiated and progressed only under stimulation by light and completely stopped in the absence of light. Block copolymers were synthesized to demonstrate high retention of chain end fidelity in the polymers and livingness of the process.

  5. 2-(4-Meth-oxy-phen-yl)-1-pentyl-4,5-di-phenyl-1H-imidazole.

    PubMed

    Simpson, Jim; Mohamed, Shaaban K; Marzouk, Adel A; Talybov, Avtandil H; Abdelhamid, Antar A

    2013-01-01

    The title compound, C27H28N2O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-meth-oxy substituent on the benzene ring. The two phenyl and meth-oxy-benzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the meth-oxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the meth-oxy C atom. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R2(2)(22) loops. These dimers are stacked along the a-axis direction.

  6. Derivative spectrophotometry in the determination of phenyl-beta-naphthylamine used as an antioxidant in rubber mixtures.

    PubMed

    Moldovan, Z; Alexandrescu, L

    2002-09-01

    A method for the determination of phenyl-beta-naphthylamine (PBN) in ternary mixtures by second-derivative spectrophotometry is described. The procedure works without any separation step of PBN from the other polymer additives. By applying the second-derivative spectrophotometry, Beer's law was valid over the range 0.25-10 micro g mL(-1). The proposed method has been applied to the determination PBN in synthetic ternary mixtures and rubber samples. A comparative study of the results obtained using the second and the third-derivative spectrophotometric methods is presented and evaluated. The derivative spectrophotometric method indicated that the amount of PBN found after extraction from the rubber samples was 0.97+/-0.02 g/100 g of sample.

  7. The synthesis and SAR of 2-arylsulfanyl-phenyl piperazinyl acetic acids as glyT-1 inhibitors.

    PubMed

    Smith, Garrick; Ruhland, Thomas; Mikkelsen, Gitte; Andersen, Kim; Christoffersen, Claus Tornby; Alifrangis, Lene Hjorth; Mørk, Arne; Wren, Stephen P; Harris, Neil; Wyman, Barry M; Brandt, Guillaume

    2004-08-02

    Elevation of glycine levels and activation of the NMDA receptor by inhibition of the glycine transporter 1 (GlyT-1) is a potential strategy for the treatment of schizophrenia. A novel series of GlyT-1 inhibitors have been identified containing the 2-arylsulfanyl-phenylpiperazine motif. The most prominent member of this series, (R)-4-[5-chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-2-methyl-piperazin-1-yl-acetic acid (31) is a potent glycine transporter-1 inhibitor (IC(50)=150 nM), which elevated glycine levels in rat ventral hippocampus as measured by microdialysis in vivo at doses of 1.2-4.6 mg/kg s.c.

  8. Electrochemical and Spectroscopic Behaviors of 1-(o-, m-, p- Cl, or Br) Substituted Phenyl-3, 5-diphenylformazans in Dimethyl Sulfoxide.

    PubMed

    Tezcan, Habibe; Ekmekci, Güler

    2010-03-01

    1-(o-, m-, p-Cl, -Br) substituted phenyl-3, 5-diphenylformazans were synthesized. Their structures were elucidated and spectral behaviours were investigated by elemental analysis, FT-IR, UV-vis spectral data. The electrochemical properties such as number of electrons transferred (n), diffusion coefficient (D) and heterogeneous rate constant (ks) were determined and possible mechanisms were proposed using platinum and ultramicro platinum electrodes, cyclic voltammetry, linear sweep voltammetry and chronoamperometry. The oxidations were carried out at different electrochemical steps that were dependent upon the structure of formazans. The relation between their absorption properties with electrochemical properties was investigated. A suitable correlation was obtained between the absorption λmax with electrochemical properties, and between the oxidation peak potentials Eox1 with ks values of formazans.

  9. Effective attenuation of atrazine-induced histopathological changes in testicular tissue by antioxidant N-phenyl-4-aryl-polyhydroquinolines.

    PubMed

    Chandak, Navneet; Bhardwaj, Jitender K; Zheleva-Dimitrova, Dimitrina; Kitanov, Gerassim; Sharma, Rajnesh K; Sharma, Pawan K; Saso, Luciano

    2015-01-01

    Some of the environmental toxicants acting as endocrine disruptors have been associated with health hazards in human and wildlife by modulating hormonal actions. Atrazine, a strong endocrine disruptor, induces detrimental effects on gonads in male and female, and causes impairment of fertility and developmental problems as well as sex alterations. Atrazine decreases the activities of antioxidant enzymes and thus responsible for oxidative stress. Natural antioxidants have shown ability to reduce/slow down the apoptotic effect of atrazine on testicular tissue. In the present study, some N-phenyl-4-aryl-polyhydroquinolines bearing phenolic or/and alkoxy group(s) (6a-6g) were synthesized and evaluated for antioxidant activity in four different assays. Three best compounds (6e-6g) were studied for their ameliorative effect on testicular tissue supplemented with atrazine in vitro.

  10. Design, synthesis and anticonvulsant evaluation of novel N-(4-substituted phenyl)-2-[4-(substituted) benzylidene]-hydrazinecarbothio amides.

    PubMed

    Tripathi, Laxmi; Kumar, Praveen; Singh, Ranjit; Stables, James P

    2012-01-01

    Thirty six new N-(4-substituted phenyl)-2-[4-(substituted) benzylidene]-hydrazinecarbothioamides were synthesized and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity was established in three seizure models i.e. MES, scMET and 6 Hz model. The most active compound was 2-[4-(4-chlorophenoxy)benzylidene]-N-(4-fluorophenyl)hydrazinecarbothioamide PC 31 which showed 100% protection at 0.5 h in the 6 Hz test. Compound 2-[4-(4-bromophenoxy) benzylidene]-N-(4-bromophenyl) hydrazinecarbothioamide PC 23 was found to be active in both the MES and 6 Hz test. A computational study was carried out from calculation of a pharmacophore pattern and the prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as glutamate, GABA (A) delta and GABA (A) alpha-1 receptors, in the Lamarckian genetic algorithm based on flexible docking studies.

  11. Structure-guided Discovery of Phenyl diketo-acids as Potent Inhibitors of M. tuberculosis Malate Synthase

    PubMed Central

    Krieger, Inna V.; Freundlich, Joel S.; Gawandi, Vijay B.; Roberts, Justin P.; Gawandi, Vidyadhar B.; Sun, Qingan; Owen, Joshua L.; Fraile, Maria T.; Huss, Sofia I.; Lavandera, Jose-Luis; Ioerger, Thomas R.; Sacchettini, James C.

    2012-01-01

    Summary The glyoxylate shunt plays an important role in fatty-acid metabolism, and has been shown to be critical to survival of several pathogens involved in chronic infections. For Mycobacterium tuberculosis (Mtb), a strain with a defective glyoxylate shunt was previously shown to be unable to establish infection in a mouse model. We report the development of novel phenyl-diketo acid (PDKA) inhibitors of malate synthase (GlcB), one of two glyoxylate shunt enzymes, using structure-based methods. PDKA inhibitors were active against Mtb grown on acetate, and over-expression of GlcB ameliorated this inhibition. Crystal structures of complexes of GlcB with PDKA inhibitors were used to guide optimization of potency. A selected PDKA compound demonstrated efficacy in a mouse model of tuberculosis. The discovery of these PDKA derivatives provides chemical validation of GlcB as an attractive target for tuberculosis therapeutics. PMID:23261599

  12. In vivo metabolism of N-phenyl-N'-(3,5-dimethylpyrazole-4-yl) thiourea in rats.

    PubMed

    Kaymakcioğlu, Bedia Koçyiğit; Rollas, Sevim; Kartal-Aricioğlu, Feyza

    2003-01-01

    Thiourea derivatives have been shown to posses several biological activities. Therefore a series of N-substituted -N'-(3,5-di/1,3,5trimethylpyrazole-4-yl)thioureas were synthesized and the antitubercular and anticonvulsant activities were studied. Among the new compounds, N-phenyl-N'-(3,5-dimethylpyrazole4-yl)thiourea (S) was demonstrated to have remarkable anticonvulsant activity. In this study, S was selected as a model compound and the in vivo metabolic pathway in rats was investigated. The substrate was given intraperitoneally (50 mg/kg) and blood samples were collected at 0, 1, 2, 4, 8, 12, 24 and 48 h. The substrate and its potential metabolites were separated using HPLC on reverse phase system. The substrate was detected at all times with small quantity of metabolites.

  13. Influence of chromophore dipole moments in parameters of organic light emitting devices based on phenyl and methyl modified pyrazoloquinoline.

    PubMed

    Gondek, E; Nizioł, J; Danel, A; Szlachcic, P; Pluciński, K; Sanetra, J; Kityk, I V

    2010-05-01

    Absorption, photo- and electroluminescence spectra of some trityl substituted 1H-pyrazolo[3,4-b]quinolines derivatives (methyl- and phenyl substituted) and fabrication of the single layered organic light emitting diodes are reported. The bulky trityl substituent was introduced to prevent aggregation and crystallization of the dopant in polymer matrix. Role of ground state dipole moments in the observed red Stokes shift, electroluminescent features and photocarrier transport is explored. The maximally achieved brightness about 50Cd/m(2) is observed in the spectral range extending from 443nm up to 462nm. The voltage threshold was varied from 7.8V up to 10V. The brightness-current dependences show an existence of at least two types of carrier injections.

  14. Supramolecular assemblies of phenyl-pyridyl-triazolopyridine and β-cyclodextrin as sensor of divalent cations in aqueous solution.

    PubMed

    Jullian, Carolina; Fernández-Sandoval, Samuel; Celis-Barros, Cristian; Abarca, Belén; Ballesteros, Rafael; Zapata-Torres, Gerald

    2015-05-05

    The chemosensor 3-phenyl-7-(pyrid-2-yl)-[1,2,3]triazolo[1,5-a]pyridine (PhPTP) used in combination with two different cyclodextrins, enable its solubilization and stabilization in aqueous solution. The behavior of the inclusion complex, and its binding ability in both cyclodextrins were investigated by means of absorption and fluorescence spectroscopy. The best results were obtained for PhPTP-DMβCD assembly, and its orientation in the DMβCD nano cavity was obtained by 2D-NMR. This inclusion geometry was confirmed by docking studies. The binary complex was proved as chemosensor upon the presence of different divalent cations in aqueous solutions. The PhPTP-DMβCD system, displays a high sensitivity for Fe(2+) by fluorescence quenching in neutral aqueous solution even in the presence of other metals showing high selectivity towards Fe(2+).

  15. Three-Dimensional Carbon Allotropes Comprising Phenyl Rings and Acetylenic Chains in sp+sp2 Hybrid Networks

    PubMed Central

    Wang, Jian-Tao; Chen, Changfeng; Li, Han-Dong; Mizuseki, Hiroshi; Kawazoe, Yoshiyuki

    2016-01-01

    We here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+sp2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells in the symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicate that phenylacetylene is metallic, while phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties. PMID:27087405

  16. Preparation of bis(4-(3,4 dimethylene pyrrolidyl) phenyl) methane as a high temperature reactive oligomer

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M.; Smith, Joseph G.; Yoshimatsu, Akira

    1987-01-01

    A major goal in the field of high temperature polymers was to prepare aromatic polyimides that can be easily fabricated with the required thermal and physical properties for aerospace applications. Recent research was directed to achieve polyimides that are: soluable in a common organic solvent; melt-processable; and thermally curable without the evolution of volatile by-products. A monomer, N-phenyl 3,4-dimethylene pyrrolidine, that can be modified to form a bis (exocyclodiene) I for the preparation of polyimides by the Diels-Alder process was developed. Preparation of high temperature polymeric materials by Diels-Alder polymerization that will maintain their integrity and toughness during long exposure time at elevated temperature is sought.

  17. Spectroscopic studies on 9H-carbazole-9-(4-phenyl) boronic acid pinacol ester by DFT method

    NASA Astrophysics Data System (ADS)

    Sas, E. B.; Kurt, M.; Can, M.; Horzum, N.; Atac, A.

    2016-08-01

    9H-Carbazole-9-(4-phenyl) boronic acid pinacol ester (9-CPBAPE) molecule was investigated by FT-IR, Raman, UV-vis, 1H and 13C NMR spectra. FT-IR, FT-Raman and dispersive Raman spectra were recorded in the solid phase. 1H, 13C NMR and UV-vis spectra were recorded in dimethyl sulfoxide (DMSO) solution. The results of theoretical calculations for the spectra of the title molecule were compared with the experimental spectra. The highest occupied molecular orbital (HOMO) the lowest unoccupied molecular orbital (LUMO) and molecular electrostatic potential (MEP) analyses were performed. The theoretical calculations for the molecular structure and spectroscopic studies were performed with DFT (B3LYP) and 6-311G (d,p) basis set calculations using the Gaussian 09 program. The total (TDOS), partial (PDOS) density of state and overlap population density of state (OPDOS) diagrams analyses were performed using GaussSum 2.2 program.

  18. (S,R,Rp)-N,N-Dimethyl-1-{2-[(1-phenyl-ethyl)amino-meth-yl]ferrocen-yl}ethanamine.

    PubMed

    Zheng, Xiu-Li; Liu, Jin-Ting

    2009-03-25

    The title chiral ferrocene compound, [Fe(C(5)H(5))(C(18)H(25)N(2))], contains one planar and two central chiral centers. It is of inter-est with respect to asymmetric catalysis. The absolute configuration of the planar chirality is Rp at the ferrocene group and those of the two C chiral centers are R at the CH carbon of the ethanamine unit and S at the CH carbon of the phenyl-ethyl-amino substituent. In the ferrocenyl unit, the cyclo-penta-dienyl (Cp) rings are planar, with maximum deviations of 0.002 (2) Å for the substituted and 0.008 (3) Å for the unsubstituted Cp ring. The dihedral angle between the ring planes is 2.12 (15)° and the rings are twisted slightly from an eclipsed conformation by 7.06-7.60°.

  19. Crystal structure of bromido­nitro­syl­bis(tri­phenyl­phosphane-κP)nickel(II)

    PubMed Central

    Hockley, Rose; Irshad, Hira; Sheriff, Tippu S.; Motevalli, Majid; Marinakis, Sarantos

    2015-01-01

    The asymmetric unit of the title complex, [NiBr(NO){P(C6H5)3}2], comprises two independent mol­ecules each with a similar configuration. The NiII cation is coordinated by one bromide anion, one nitrosyl anion and two tri­phenyl­phosphane mol­ecules in a distorted BrNP2 tetra­hedral coordination geometry. The coordination of the nitrosyl group is non-linear, the Ni—N—O angles being 150.2 (5) and 151.2 (5)° in the two independent mol­ecules. In the crystal, mol­ecules are linked by weak C—H⋯Br hydrogen bonds and weak C—H⋯π inter­actions into a three-dimensional supra­molecular architecture. PMID:26029415

  20. Three-dimensional carbon allotropes comprising phenyl rings and acetylenic chains in sp+sp2 hybrid networks

    DOE PAGES

    Wang, Jian -Tao; Chen, Changfeng; Li, Han -Dong; ...

    2016-04-18

    Here, we here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+sp2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells R-3m symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicate that phenylacetylene is metallic, whilemore » phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties.« less

  1. Synthesis, structural, theoretical studies and biological activities of 3-(arylamino)-2-phenyl-1H-inden-1-one derivative

    NASA Astrophysics Data System (ADS)

    El-Sheshtawy, Hamdy S.; Abou Baker, Ahmed M.

    2014-06-01

    Five derivatives of 2-phenyl-1H-indene-1-one have been prepared and fully characterized. Spectroscopic techniques such as FT-IR, 1H NMR, mass spectrometry, and elemental analysis were used to investigate the chemical structures and physical properties of the prepared compounds. The optimized structures and the distribution of the frontier molecular orbital were obtained using density functional theory (DFT) at B3LYP/6-311++G(d,p) level of theory. Additionally, the UV spectral properties of the indene compounds were corroborated by frontier orbital (HOMO and LUMO) calculations. Intramolecular charge transfer (ICT) peak has been observed in the UV spectra of the compounds and theoretically confirmed by the HOMO and LUMO analysis. The potential use of these compounds as antibacterial agents was investigated. The results show that indene-1-one derivatives have an antibacterial activity for both gram-negative (Pseudomonas aeruginosa) and gram-positive (Methicillin Resistant Staphylococcus aureus) bacteria.

  2. Design, synthesis and biological evaluation of novel benzimidazole-2-substituted phenyl or pyridine propyl ketene derivatives as antitumour agents.

    PubMed

    Wu, Lin-tao; Jiang, Zhi; Shen, Jia-jia; Yi, Hong; Zhan, Yue-chen; Sha, Ming-quan; Wang, Zhen; Xue, Si-tu; Li, Zhuo-rong

    2016-05-23

    A series of novel benzimidazole-2-subsituted phenyl or pyridine propyl ketene derivatives were designed and synthesized. The biological activities of these derivatives were then evaluated as potential antitumour agents. These compounds were assayed for growth-inhibitory activity against HCT116, MCF-7 and HepG2 cell lines in vitro. The IC50 values of compounds A1 and A7 against the cancer cells were 0.06-3.64 μM and 0.04-9.80 μM, respectively. Their antiproliferative activities were significantly better than that of 5-Fluorouracil (IC50: 56.96-174.50 μM) and were close to that of Paclitaxel (IC50: 0.026-1.53 μM). The activity of these derivatives was over 100 times more effective than other reported structures of chalcone analogues (licochalcone A). A preliminary mechanistic study suggested that these compounds inhibit p53-MDM2 binding. Compounds A1, A7 and A9 effectively inhibited tumour growth in BALB/c mice with colon carcinoma HCT116 cells. The group administered 200 mg/kg of compound A7 showed a 74.6% tumour growth inhibition with no signs of toxicity at high doses that was similar to the inhibition achieved with the 12.5 mg/kg irinotecan positive control (70.2%). Therefore, this class of benzimidazole-2-subsituted phenyl or pyridine propyl ketene derivatives represents a promising lead structure for the development of possible p53-MDM2 inhibitors as new antitumour agents.

  3. Mast Cells Release Chemokine CCL2 in Response to Parkinsonian Toxin 1-Methyl-4-Phenyl-Pyridinium (MPP(+)).

    PubMed

    Kempuraj, Duraisamy; Thangavel, Ramasamy; Fattal, Ranan; Pattani, Sagar; Yang, Evert; Zaheer, Smita; Santillan, Donna A; Santillan, Mark K; Zaheer, Asgar

    2016-05-01

    Microglial activation and release of inflammatory cytokines and chemokines are crucial events in neuroinflammation. Microglial cells interact and respond to other inflammatory cells such as T cells and mast cells as well as inflammatory mediators secreted from these cells. Recent studies have shown that neuroinflammation causes and accelerates neurodegenerative disease such as Parkinson's disease (PD) pathogenesis. 1-methyl-4-phenyl-pyridinium ion (MPP(+)), the active metabolite of neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydro pyridine activates glial cells and mediate neurodegeneration through release of inflammatory mediators. We have shown that glia maturation factor (GMF) activates glia and induces neuroinflammation and neurodegeneration and that MPP(+) activates mast cells and release proinflammatory cytokines and chemokines. The chemokine (C-C motif) ligand 2 (CCL2) levels have been shown to be elevated and play a role in PD pathogenesis. In the present study, we analyzed if MPP(+) activates mouse and human mast cells to release chemokine CCL2. Mouse bone marrow-derived mast cells (BMMCs) and human umbilical cord blood-derived cultured mast cells (hCBMCs) were incubated with MPP(+) (10 µM) for 24 h and CCL2 levels were measured in the supernatant media by ELISA. MPP(+)-significantly induced CCL2 release from BMMCs and hCBMCs. Additionally, GMF overexpression in BMMCs obtained from wild-type mice released significantly more CCL2, while BMMCs obtained from GMF-deficient mice showed less CCL2 release. Further, we show that MPP(+)-induced CCL2 release was greater in BMMCs-astrocyte co-culture conditions. Uncoupling protein 4 (UCP4) which is implicated in neurodegenerative diseases including PD was detected in BMMCs by immunocytochemistry. Our results suggest that mast cells may play role in PD pathogenesis.

  4. Computational and spectroscopic studies of the imidazole-fused phenanthroline derivatives containing phenyl, naphthyl, and anthryl groups

    NASA Astrophysics Data System (ADS)

    Wang, Jinglan; Xu, Shengxian; Zhao, Feng; Xia, Hongying; Wang, Yibo

    2016-03-01

    Three N,N-bidentate ligands, 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (1), 2-(2-naphyl)-1H-imidazo[4,5-f]phenanthroline (2), and 2-(2-anthryl)-1H-imidazo[4,5-f]phenanthroline (3) have been synthesized and characterized. Effects of aryl subsistiuents (phenyl, naphthyl, and anthryl) on the photophysical properties of these ligands in solution have been studied. Ligand 1 exhibit the main absorption band at 283 nm with the shoulder bands at 300-350 nm and these bands are assigned as the typical π→π*(imPhen) state (imPhen = 1H-imidazo[4,5-f][1,10]phenanthroline). A similar absorption spectrum was also observed in the case of 2, in which the charge transfer (CT) state should be considered. 3 shows the slightly different absorption properties compared to that of 1 and 2. The highest-lying absorption band at 257 nm is assigned as a mixed π→π*(imPhen)/π→π*(Anth) (Anth = anthracene) state. Additionally, the characteristic absorption band of anthryl group with three vibronic bands at 352, 367, and 386 nm also observed in the visible region range from 340 to 400 nm. 1 shows the typical ligand-centered 1π→π* emission, while 2 and 3 emit from the mixed 1π→π*/CT states. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) were employed to rationalize the photophysical properties of these ligands studied. The theoretical data confirm the assignment of the experimental absorption spectra and the nature of the emitting states.

  5. Syntheses of 5-phenyl-2-pyridinamine, a possibly carcinogenic pyrolysis product of phenylalanine, and some of its putative metabolites.

    PubMed

    Stavenuiter, J F; Verrips-Kroon, M; Bos, E J; Westra, J G

    1985-01-01

    5-Phenyl-2-pyridinamine (PPA) is a pyrolysis product of phenylalanine, the presence of which has been demonstrated in broiled sardines. Since PPA is mutagenic in the Ames test and is structurally related to the aminobiphenyls, it has to be considered as potentially carcinogenic. In this study procedures for the synthesis of PPA and its possible metabolites were developed to make them available for biological studies. PPA was synthesized in one step from 2,5-pyridinediamine. However, this method is only suitable for the preparation of small amounts. Larger quantities were synthesized starting from 5-nitro-2-pyridinamine in four steps. PPA was also prepared via a six-step synthesis, starting from 6-amino-3-pyridinecarboxamide. This route was also used for the synthesis of tritiated PPA [( 3H]PPA) and 2-nitro-5-phenylpyridine, the latter being the precursor of the two putative proximate carcinogenic metabolites, viz. the hydroxylamine and the hydroxamic acid of PPA. In the course of these multi-step syntheses a new method for the preparation of unsymmetrical biaryls was worked out. The following possible metabolites were also synthesized: N-(5-phenyl-2-pyridinyl)acetamide in the course of the synthesis of PPA starting from 5-nitro-2-pyridinamine, and both 5-(4-hydroxyphenyl)-2-pyridinamine (4'-OH-PPA) and N-[5-(4-hydroxyphenyl)-2-pyridinyl]acetamide starting from 5-(4-aminophenyl)-2-pyridinamine. After incubation of PPA in suspensions of freshly isolated hepatocytes from rats pretreated with polychlorinated biphenyls (Aroclor 1254) or PPA itself, the presence of 4'-OH-PPA was demonstrated.

  6. N-(4-Meth-oxy-phen-yl)-6-methyl-2-phenyl-5-{[4-(tri-fluoro-meth-yl)anilino]meth-yl}pyrimidin-4-amine.

    PubMed

    Cieplik, Jerzy; Pluta, Janusz; Bryndal, Iwona; Lis, Tadeusz

    2013-11-27

    The title compound, C26H23F3N4O, crystallizes with two symmetry-independent mol-ecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the meth-oxy-phenyl ring. The -CF3 group of mol-ecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853 (4). The dihedral angles between the pyrimidine ring and the attached phenyl, meth-oxy-phenyl and tri-fluoro-methyl-phenyl rings are 8.1 (2), 37.5 (2) and 70.7 (2)°, respectively, in mol-ecule A, and 9.3 (2), 5.3 (2) and 79.7 (2)° in mol-ecule B. An intra-molecular N-H⋯N hydrogen bond occurs in each mol-ecule. In the crystal, two crystallographically independent mol-ecules associate into a dimer via a pair of N-H⋯N hydrogen bonds, with a resulting R 2 (2)(12) ring motif and π-π stacking inter-actions [centroid-centroid distance = 3.517 (4) Å] between the pyrimidine rings. For the A mol-ecules, there are inter-molecular C-H⋯O hydrogen bonds between an aryl C atom of meth-oxy-phenyl ring and a meth-oxy O atom of an adjacent mol-ecule. A similar inter-action is lacking in the B mol-ecules.

  7. Crystal structure of a mixed-ligand dinuclear Ba-Zn complex with 2-meth-oxy-ethanol having tri-phenyl-acetate and chloride bridges.

    PubMed

    Utko, Józef; Sobocińska, Maria; Dobrzyńska, Danuta; Lis, Tadeusz

    2015-07-01

    The dinuclear barium-zinc complex, μ-chlorido-1:2κ(2) Cl:Cl-chlorido-2κCl-bis-(2-meth-oxy-ethanol-1κO)bis-(2-meth-oxy-ethanol-1κ(2) O,O')bis-(μ-tri-phenyl-acetato-1:2κ(2) O:O')bariumzinc, [BaZn(C20H15O2)2Cl2(C3H8O2)4], has been synthesized by the reaction of barium tri-phenyl-acetate, anhydrous zinc chloride and 2-meth-oxy-ethanol in the presence of toluene. The barium and zinc metal cations in the dinuclear complex are linked via one chloride anion and carboxyl-ate O atoms of the tri-phenyl-acetate ligands, giving a Ba⋯Zn separation of 3.9335 (11) Å. The irregular nine-coordinate BaO8Cl coordination centres comprise eight O-atom donors, six of them from 2-meth-oxy-ethanol ligands (four from two bidentate O,O'-chelate inter-actions and two from monodentate inter-actions), two from bridging tri-phenyl-acetate ligands and one from a bridging Cl donor. The distorted tetra-hedral coordination sphere of zinc comprises two O-atom donors from the tri-phenyl-acetate ligands and two Cl donors (one bridging and one terminal). In the crystal, O-H⋯Cl, O-H⋯O and C-H⋯Cl inter-molecular inter-actions form a layered structure, lying parallel to (001).

  8. Structural and photophysical properties of HPPCO (4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one) derivatives

    NASA Astrophysics Data System (ADS)

    Jeong, Yong-Kwang; Kim, Min-Ah; Lee, Hyo-Sung; Kim, Jong-Moon; Lee, Sung Woo; Kang, Jun-Gill

    2015-01-01

    Proton-substitution effects of 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one (HPPCO) on structural and photophysical properties were presented. HPPCO crystallized in the orthorhombic space group Pbca with an intermolecular hydrogen bonding between OH and oxygen atom of the carbonyl. The proton-substituted derivatives, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl acetate (OPPCA) and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl benzoate (OPPCB), crystallized in the monoclinic P21/c space group. For OPPCA and OPPCB, a weak interaction between carbonyl oxygen atom in the substituted group and carbon atom in the fused ring was responsible for three-dimensional arrangements. In addition, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl furan-2-carboxylate (OPPCF), and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl naphthoate (OPPCN) were also synthesized. HPPCO and the four derivatives excited by ultraviolet (UV) light produced blue emission. Proton substitution of the OH group significantly increased the radiative transitions and moderately decreased the non-radiative transitions. Consequently the luminescence quantum yields of the derivatives enhanced more than 4.6-fold, no matter what the groups were substituted. Structural and optical properties were further determined using density functional theory (DFT) and ZINDO calculations. The planar structure of the pyridocarbazole-fused ring resulted in π → π* electronic transitions within the main frame, with an additional transition from the n(O) of carbonyl to the π* of the main frame. The three excited states that arose from these transitions were responsible for the blue luminescence.

  9. Structural and photophysical properties of HPPCO (4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one) derivatives.

    PubMed

    Jeong, Yong-Kwang; Kim, Min-Ah; Lee, Hyo-Sung; Kim, Jong-Moon; Lee, Sung Woo; Kang, Jun-Gill

    2015-01-05

    Proton-substitution effects of 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one (HPPCO) on structural and photophysical properties were presented. HPPCO crystallized in the orthorhombic space group Pbca with an intermolecular hydrogen bonding between OH and oxygen atom of the carbonyl. The proton-substituted derivatives, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl acetate (OPPCA) and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl benzoate (OPPCB), crystallized in the monoclinic P2₁/c space group. For OPPCA and OPPCB, a weak interaction between carbonyl oxygen atom in the substituted group and carbon atom in the fused ring was responsible for three-dimensional arrangements. In addition, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl furan-2-carboxylate (OPPCF), and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl naphthoate (OPPCN) were also synthesized. HPPCO and the four derivatives excited by ultraviolet (UV) light produced blue emission. Proton substitution of the OH group significantly increased the radiative transitions and moderately decreased the non-radiative transitions. Consequently the luminescence quantum yields of the derivatives enhanced more than 4.6-fold, no matter what the groups were substituted. Structural and optical properties were further determined using density functional theory (DFT) and ZINDO calculations. The planar structure of the pyridocarbazole-fused ring resulted in π→π(*) electronic transitions within the main frame, with an additional transition from the n(O) of carbonyl to the π(*) of the main frame. The three excited states that arose from these transitions were responsible for the blue luminescence.

  10. Asymmetric tetranuclear nickel chains with unidirectionally ordered 2-(α-(5-phenyl)pyridylamino)-1,8-naphthyridine ligands.

    PubMed

    Tsou, Lien-Hung; Sigrist, Marc; Chiang, Ming-Hsi; Horng, Er-Chien; Chen, Chun-Hsien; Huang, Shou-Ling; Lee, Gene-Hsiang; Peng, Shie-Ming

    2016-11-01

    The new ligand, 2-(α-(5-phenyl)pyridylamino)-1,8-naphthyridine (Hphpyany), was synthesised by a palladium(0)-catalysed reaction of 2-chloro-1,8-naphthyridine with 2-amino-5-phenylpyridine in the presence of potassium tert-butoxide. Linear tetranickel metal complexes, [Ni4(phpyany)4Cl2](CF3SO3) 1, [Ni4(phpyany)4Cl2](BF4)22, [Ni4(phpyany)4(NCS)2](ClO4) 3 and [Ni4(phpyany)4(NCS)2](CF3SO3)24 were prepared and crystallographically characterised. Complexes 1-4 demonstrate that, for the first time, four asymmetric ligands align unidirectionally and thus configure (4,0)-form tetranickel strings, specifically, with the phenyl groups of the four phpyany(-) pointing to one side of the Ni4 chain and naphthyridyl to the other. The remarkably short Ni-Ni distances (ca. 2.33 Å) for 1 and 3 indicate partial metal-metal bonding, which can be viewed as both complexes containing one mixed-valence Ni2(3+) unit. The measurements of the magnetic susceptibility reveal that Ni4(7+) complexes 1 and 3 exhibit antiferromagnetic interactions (J = -42 cm(-1) for 1 and -46 cm(-1) for 3) between the terminal Ni(2+) ion and the Ni2(3+) unit, while Ni4(8+) complexes 2 and 4 exhibit antiferromagnetic interactions (J = -33 cm(-1) for 2 and -35 cm(-1) for 4) between the two terminal Ni(2+) ions. The results of the cyclic voltammetry indicate the presence of two reversible redox couples at E1/2((1)) = 0.12 V, E1/2((2)) = -0.65 V for 1, and at E1/2((1)) = 0.12 V, E1/2((2)) = -0.72 V for 3. The products of the first oxidation for 1 and 3 are the oxidised species 2 and 4, respectively. The values of single-molecule resistance (15.4 (±3.46) MΩ for 3 and 16.2 (±5.04) MΩ for 4) were determined by STM-based break-junction methods. The results represent the first conductance measurements of linear tetranickel chains.

  11. Crystal structure of (E)-N 1-[(anthracen-9-yl)methyl­idene]-N 4-phenyl­benzene-1,4-di­amine

    PubMed Central

    Ahmad, Musheer; Golenya, Irina A.

    2017-01-01

    The title compound, C27H20N2, a Schiff base synthesized via a condensation reaction between anthracene-9-carbaldehyde and N-phenyl-p-phenyl­enedi­amine, crystallizes with three independent mol­ecules in the asymmetric unit. The three mol­ecules have slightly varying overall conformations, all having trans conformations with respect to the C=N bond. In the crystal, the packing features N—H⋯N hydrogen bonds, which connect mol­ecules into chains extending along the c-axis direction, inter­linked by C—H⋯π inter­actions (minimum H⋯Cg = 2.65 Å) into sheets lying parallel to (001). PMID:28217328

  12. Synthesis of [3 alpha-3H]7-dehydrocholesterol via stable tritiated 4-phenyl-1,2,4-triazoline-3,5-dione derivative.

    PubMed

    Batta, A K; Salen, G; Tint, G S; Honda, A; Shefer, S

    1997-11-01

    Synthesis of [3 alpha-3H]7-dehydrocholesterol is described via protection of the 5,7-diene system in 7-dehydrocholesterol as the Diels-Alder adduct with 4-phenyl-1,2,4-triazoline-3,5-dione followed by oxidation of the hydroxyl group to give the 3-oxo adduct. Reduction of the keto adduct with [3H]sodium borohydride produced the adduct of [3 alpha-3H]7-dehydrocholesterol from which the radiolabeled sterol was obtained via treatment with lithium aluminum hydride. The advantage of the method is that highly labeled [3 alpha-3H]7-dehydrocholesterol can be prepared. Further, unlike 7-dehydrocholesterol, its adduct with 4-phenyl-1,2,4-triazoline-3,5-dione is stable and can be stored. This allows the preparation of small batches of [3 alpha-3H]7-dehydrocholesterol for immediate use in biological experiments, and losses due to decomposition of excess radiolabeled 7-dehydrocholesterol are minimized.

  13. Crystal structure of (E)-4-[N-(7-methyl-2-phenyl-imidazo[1,2-a]pyridin-3-yl)carboximido-yl]phenol.

    PubMed

    Elaatiaoui, Abdelmalik; Saddik, Rafik; Benchat, Noureddine; Saadi, Mohamed; El Ammari, Lahcen

    2015-10-01

    The mol-ecule of the title compound, C21H17N3O, is built up from fused five- and six-membered rings connected to a methyl group, a phenyl ring and an (imino-meth-yl)phenol group. The fused ring system is almost planar (r.m.s. deviation = 0.031 Å) and forms dihedral angles of 64.97 (7) and 18.52 (6)° with the phenyl ring and the (imino-meth-yl)phenol group, respectively. In the crystal, centrosymmetric mol-ecules are linked by pairs of C-H⋯π inter-actions into dimeric units, which are further connected by O-H⋯N hydrogen bonds to form layers parallel to (101).

  14. Crystal structure of (E)-4-[N-(7-methyl-2-phenyl­imidazo[1,2-a]pyridin-3-yl)carboximido­yl]phenol

    PubMed Central

    Elaatiaoui, Abdelmalik; Saddik, Rafik; Benchat, Noureddine; Saadi, Mohamed; El Ammari, Lahcen

    2015-01-01

    The mol­ecule of the title compound, C21H17N3O, is built up from fused five- and six-membered rings connected to a methyl group, a phenyl ring and an (imino­meth­yl)phenol group. The fused ring system is almost planar (r.m.s. deviation = 0.031 Å) and forms dihedral angles of 64.97 (7) and 18.52 (6)° with the phenyl ring and the (imino­meth­yl)phenol group, respectively. In the crystal, centrosymmetric mol­ecules are linked by pairs of C—H⋯π inter­actions into dimeric units, which are further connected by O–H⋯N hydrogen bonds to form layers parallel to (101). PMID:26594488

  15. Oxidation of phenyl propyne catalyzed by copper(II) complexes of a benzimidazolyl schiff base ligand: Effect of acid/base, oxidant, surfactant and morphology

    NASA Astrophysics Data System (ADS)

    Kumar, Ravinder; Mathur, Pavan

    2015-02-01

    Copper(II) complexes with a new N-Substituted benzimidazolyl schiff base ligand are used as catalyst for the oxidation of 1-phenyl propyne. The oxidation is carried out under mild conditions using stoichiometric amounts of oxidant and catalytic amounts of Cu(II) complex as catalyst. Effect of acid/base, oxidant, morphology and surfactant has been studied. Two major products of phenyl propyne oxidation are the α-diketonic product and a terminal aldehyde. Diketone is the major product under acidic conditions while aldehyde formation is highest under basic conditions. The maximum conversion is found with the NO3- bound complex. GC-MS is used to find the percentage yields of products. SEM and PXRD of the reused complexes as catalyst suggest that morphology affects the catalytic efficiency.

  16. Taurine fails to protect against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced striatal dopamine depletion in mice.

    PubMed

    Navneet, A K; Appukuttan, T A; Pandey, M; Mohanakumar, K P

    2008-08-01

    Taurine, a known antioxidant and neuroprotector has been investigated for its free radical scavenging action in vitro in isolated mitochondria, and tested whether it protects against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced dopaminergic neurodegeneration in mice. Taurine (0.1-10 mM) did not affect 1-methyl-4-phenyl pyridinium-induced hydroxyl radical production in isolated mitochondria. Systemic administration of taurine (250 mg/kg, i.p.) caused a small, but significant loss of dopamine levels in the striatum of mice. Taurine failed to reverse MPTP-induced striatal dopamine depletion, but caused significant increase in dopamine turnover in these animals. In the light of the present study it may be suggested that consumption of taurine may neither help in scavenging of neurotoxic hydroxyl radicals in the brain mitochondria, nor would it help in blocking the process of neurodegeneration.

  17. Crystal structure of 2-[2-(hy­droxy­imino)-1-phenyl­propyl­idene]-N-phen­ylhydrazinecarbo­thio­amide

    PubMed Central

    Anderson, Brian J.; Freedman, Michael B.; Millikan, Sean P.; Smolenski, Victoria A.; Jasinski, Jerry P.

    2015-01-01

    In the title compound, C16H16N4OS, an intra­molecular C—H⋯S hydrogen bond is observed. With the exception of the phenyl ring of the phenyl­propyl­idene unit, the remainder of the mol­ecule has an almost planar skeleton with an r.m.s. deviation of 0.121 (5) Å from the plane through the remaining 16 atoms. In the crystal O—H⋯N hydrogen bonds are observed between the terminal hy­droxy­imino groups, forming inverson dimers with R 2 2(6) graph-set motifs. Additional C—H⋯N contacts stack the dimers along [100]. While no π—π inter­actions are present, weak C—H⋯O and O—H⋯Cg inter­actions are also observed and help stabilize the crystal packing. PMID:26594484

  18. Crystal structure of (1-eth­oxy­ethyl­idene)di­methyl­aza­nium tetra­phenyl­borate

    PubMed Central

    Tiritiris, Ioannis; Saur, Stefan; Kantlehner, Willi

    2015-01-01

    In the cation of the title salt, C6H14NO+·C24H20B−, the C—N bond lengths are 1.297 (2), 1.464 (2) and 1.468 (2) Å, indicating double- and single-bond character, respectively. The C—O bond length of 1.309 (2) Å shows double-bond character, pointing towards charge delocalization within the NCO plane of the iminium ion. In the crystal, C—H⋯π inter­actions between the iminium H atoms and the phenyl C atoms of the anion are present. The phenyl rings form aromatic pockets, in which the iminium ions are embedded. PMID:26870564

  19. The fluorescence properties of the phenylated fullerenes C 70Ph 4, C 70Ph 6, C 70Ph 8, and C 70Ph 10 in room temperature solutions

    NASA Astrophysics Data System (ADS)

    Schwell, Martin; Gustavsson, Thomas; Marguet, Sylvie; Vaissière, Benoı̂t de La; Wachter, Norbert K.; Birkett, Paul R.; Mialocq, Jean-Claude; Leach, Sydney

    2001-12-01

    The emission and excitation spectra of four phenylated [70] fullerenes, C 70Ph 4, C 70Ph 6, C 70Ph 8, and C 70Ph 10 in cyclohexane and toluene solutions have been measured. The fluorescence spectra and related excited state properties are found to depend strongly on the number of attached phenyl groups, but with no systematic trends. Quantum yields and fluorescence lifetimes were measured for C 70Ph 6, C 70Ph 8, and C 70Ph 10, allowing the determination of S1 → S0 radiative transition rates kR. It is found that kR for C 70Ph 10 is about six times larger than for the other compounds. This is consistent with measured absorbtivities for these compounds. The particular character of C 70Ph 10 is also manifested by its higher intersystem crossing rate kISC.

  20. 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.

  1. Syntheses, structures and properties of two new coordination polymers based on D-camphoric acid and 2-phenyl-4,6-diamino-1,3,5-triazine

    NASA Astrophysics Data System (ADS)

    Lun, Huijie; Yang, Jinghe; Jin, Linyu; Cui, Sasa; Bai, Yanlong; Zhang, Xudong; Li, Yamin

    2015-05-01

    By hydrothermal method, two new coordination polymers [Co(ca)(phdat)]n (1), [Ni(ca)(phdat).0.125H2O]n (2) (H2ca=D-camphoric acid, phdat=2-phenyl-4,6-diamino-1,3,5-triazine) have been achieved and structurally characterized by IR, elemental analyses, X-ray single-crystal diffraction and TGA. The X-ray single-crystal diffraction reveals that compounds 1 and 2 are isostructural, both of which exhibit two-dimensional layered network built up from paddle-wheel Co2(CO2)4/Ni2(CO2)4 SBUs by ca2- ligand. In the existence of π…π stacking interactions between triazine rings and phenyl rings, the 3D networks are constructed with the hanging phdat filled between the neighboring layers. Furthermore, compounds 1-2 exhibit antiferromagnetic behavior and compound 2 displays a good activity for methanol oxidation.

  2. Design, synthesis and biological evaluation of novel hydroxy-phenyl-1H-benzimidazoles as radical scavengers and UV-protective agents.

    PubMed

    Bino, Alessia; Baldisserotto, Anna; Scalambra, Emanuela; Dissette, Valeria; Vedaldi, Daniela Ester; Salvador, Alessia; Durini, Elisa; Manfredini, Stefano; Vertuani, Silvia

    2017-12-01

    An ever-increasing incidence of skin neoplastic diseases is registered. Therefore, it is important to protect the skin from the UV radiation that reaches the epidermis and dermis but also to block ROS generated by them. Our attention was attracted in developing new compounds provided with both UV filtering and antioxidant capacities. To this end, 2-phenyl-1H-benzimidazole-5-sulfonic acid (PBSA), a known UV filter, was selected as lead compound for its lack of antioxidant activity, high water solubility and good safety profile. PBSA was sequentially modified introducing hydroxyls on the phenyl ring and also substituting the functional group in position 5 of the benzimidazole ring. At the end of the synthetic study, a new, very potent class of antioxidants has been obtained. Surprisingly some of the developed molecules, while devoid of significant UV-filtering activity was endowed with potent UV-filtering booster capability if associated with known commercial UVB and UVA filters.

  3. Discovery of 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives as non-peptidic selective SUMO-sentrin specific protease (SENP)1 inhibitors.

    PubMed

    Uno, Masaharu; Koma, Yosuke; Ban, Hyun Seung; Nakamura, Hiroyuki

    2012-08-15

    We developed 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivative 4 (GN6958) as a non-peptidic selective SUMO-sentrin specific protease (SENP)1 protease inhibitor based on the hypoxia inducible factor (HIF)-1α inhibitor 1 (GN6767). The direct interaction of compound 1 with SENP1 protein in cells was observed by the pull-down experiments using the biotin-tagged compound 2 coated on the streptavidin affinity column. Among the various 1-[4-(N-benzylamino)phenyl]-3-phenylurea derivatives tested, compounds 3 and 4 suppressed HIF-1α accumulation in a concentration-dependent manner without affecting the expression level of tubulin protein in HeLa cells. Both compounds inhibited SENP1 protease activity in a concentration-dependent manner, and compound 4 exhibited more potent inhibition than compound 3. Compound 4 exhibited selective inhibition against SENP1 protease activity without inhibiting other protease enzyme activities in vitro.

  4. Oxidation of phenyl propyne catalyzed by copper(II) complexes of a benzimidazolyl schiff base ligand: effect of acid/base, oxidant, surfactant and morphology.

    PubMed

    Kumar, Ravinder; Mathur, Pavan

    2015-02-05

    Copper(II) complexes with a new N-Substituted benzimidazolyl schiff base ligand are used as catalyst for the oxidation of 1-phenyl propyne. The oxidation is carried out under mild conditions using stoichiometric amounts of oxidant and catalytic amounts of Cu(II) complex as catalyst. Effect of acid/base, oxidant, morphology and surfactant has been studied. Two major products of phenyl propyne oxidation are the α-diketonic product and a terminal aldehyde. Diketone is the major product under acidic conditions while aldehyde formation is highest under basic conditions. The maximum conversion is found with the NO3(-) bound complex. GC-MS is used to find the percentage yields of products. SEM and PXRD of the reused complexes as catalyst suggest that morphology affects the catalytic efficiency.

  5. Crystal structure of 13-phenyl-2,3,4,13-tetra-hydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione.

    PubMed

    Lamera, Esma; Benzerka, Saida; Bouraiou, Abdelmalek; Bouacida, Sofiane; Merazig, Hocine; Chibani, Aissa; Le Borgne, Marc; Bouaziz, Zouhair

    2015-12-01

    The title compound, C21H16N2O3, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system (r.m.s. deviation = 0.018 Å). The phenyl ring is almost normal to the mean plane of the five-membered ring of the indazolone moiety, making a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety has an envelope conformation, with the central methyl-ene C atom as the flap. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming slabs parallel to the bc plane. The slabs are linked via C-H⋯π and π-π inter-actions [the shortest inter-centroid distance involving rings of pyrazolo-phthalazine moieties is 3.6430 (8) Å], forming a three-dimensional structure.

  6. Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-amino-phenyl-arsonate tetra-hydrate.

    PubMed

    Smith, Graham; Wermuth, Urs D

    2016-05-01

    In the structure of the brucinium salt of 4-amino-phenyl-arsonic acid (p-arsanilic acid), systematically 2,3-dimeth-oxy-10-oxostrychnidinium 4-amino-phenyl-ar-son-ate tetra-hydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water mol-ecules of solvation are accommodated between the layers and are linked to them through a primary cation N-H⋯O(anion) hydrogen bond, as well as through water O-H⋯O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure.

  7. Novel thiol-based histone deacetylase inhibitors bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold as surface recognition motif: Design, synthesis and SAR study.

    PubMed

    Wen, Jiachen; Niu, Qun; Liu, Jiang; Bao, Yu; Yang, Jinyu; Luan, Shenglin; Fan, Yinbo; Liu, Dan; Zhao, Linxiang

    2016-01-15

    A series of novel thiol-based histone deacetylase (HDAC) inhibitors bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold as surface recognition motif was designed, synthesized, and evaluated for their HDAC inhibition activity. Among them, 15j (IC50=0.08μM) was identified as a better inhibitor than Vorinostat (IC50=0.25μM) against total HDACs. In addition, Structure-activity relationships (SAR) analyses indicated that (i) compounds with different substituents on pyrazole N-1 position exhibited superior activities than those on pyrazole N-2 position, (ii) variation of functional groups on N-1'-alkyl chain terminus followed the trends of carboxyl group>hydroxyl group≫alkyl group, and (iii) methylation on pyrazole C-4 position diminished the HDAC inhibition activity. The SAR will guide us to further refine compounds bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold to achieve better HDAC inhibitors.

  8. Synthesis of 24-phenyl-24-oxo steroids derived from bile acids by palladium-catalyzed cross coupling with phenylboronic acid. NMR characterization and X-ray structures.

    PubMed

    Mayorquín-Torres, Martha C; Romero-Ávila, Margarita; Flores-Álamo, Marcos; Iglesias-Arteaga, Martin A

    2013-11-01

    Palladium-catalyzed cross coupling of phenyboronic acid with acetylated bile acids in which the carboxyl functions have been activated by formation of a mixed anhydride with pivalic anhydride afforded moderate to good yield of 24-phenyl-24-oxo-steroids. Unambiguous assignments of the NMR signals were made with the aid of combined 1D and 2D NMR techniques. X-ray diffraction studies confirmed the obtained structures.

  9. Ethyl 3-(6-phenyl-4λ4-1,2-dithiolo[1,5-b][1,2,4]dithia­zol-2-yl)propanoate

    PubMed Central

    Marković, Rade; Rašović, Aleksandar; Steel, Peter J.

    2008-01-01

    The title compound, C15H15NO2S3, exists in a bicyclic form, with resonance contributions from two monocyclic forms, each without a second S—S bond. The trithiapentalene heterocyclic ring system is planar, with a mean deviation of 0.014 (2) Å from the mean plane, and is inclined to the plane of the attached phenyl ring at an angle of 17.24 (7)°. PMID:21200742

  10. Excited-state behavior of N-phenyl-substituted trans-3-aminostilbenes: where the "m-amino effect" meets the "amino-conjugation effect".

    PubMed

    Yang, Jye-Shane; Liau, Kang-Ling; Tu, Chi-Wei; Hwang, Chung-Yu

    2005-07-28

    The electronic spectroscopy and photochemistry of the trans isomers of 3-(N-phenylamino)stilbene (m1c), 3-(N-methyl-N-phenylamino)stilbene (m1d), 3-(N,N-diphenylamino)stilbene (m1e), and 3-(N-(2,6-dimethylphenyl)amino)stilbene (m1f) and their double-bond constrained analogues m2a-m2c and m2e are reported. When compared with trans-3-aminostilbene (m1a), m1c-m1e display a red shift of the S0 --> S1 absorption and fluorescence spectra, lower oscillator strength and fluorescence rate constants, and more efficient S1 --> T1 intersystem crossing. Consequently, the N-phenyl derivatives m1c-m1e have lower fluorescence quantum yields and higher photoisomerization quantum yields. The corresponding N-phenyl substituent effect in m2a-m2e is similar in cyclohexane but smaller in acetonitrile. This is attributed to the weaker intramolecular charge transfer character for the S1 state of m2 so that the rates for intersystem crossing are less sensitive to solvent polarity. It is also concluded that N-phenyl substitutions do not change the triplet mechanism of photoisomerization for m1 in both nonpolar and polar solvents. Therefore, the "m-amino conjugation effect" reinforces the "m-amino effect" on fluorescence by further reducing its rate constants and highlights the N-phenyl-enhanced intersystem crossing from the "amino-conjugation effect" by making S1 --> T1 the predominant nonradiative decay pathway.

  11. Synthesis, spectroscopic investigations (X-ray, NMR and TD-DFT), antimicrobial activity and molecular docking of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone.

    PubMed

    Barakat, Assem; Ghabbour, Hazem A; Al-Majid, Abdullah Mohammed; Soliman, Saied M; Ali, M; Mabkhot, Yahia Nasser; Shaik, Mohammed Rafi; Fun, Hoong-Kun

    2015-07-21

    The synthesis of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone 1 is described. The molecular structure of the title compound 1 was confirmed by NMR, FT-IR, MS, CHN microanalysis, and X-ray crystallography. The molecular structure was also investigated by a set of computational studies and found to be in good agreement with the experimental data obtained from the various spectrophotometric techniques. The antimicrobial activity and molecular docking of the synthesized compound was investigated.

  12. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  13. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  14. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  15. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  16. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  17. 4-Hy­droxy-3-[(E)-3-phenyl­prop-2-eno­yl]-2H-chromen-2-one

    PubMed Central

    Ghouili, Afef; Ben Hassen, Rached

    2011-01-01

    In the title mol­ecule, C18H12O4, the phenyl ring is twisted by 23.2 (1)° from the mean plane of the chromene system. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into zigzag chains extending in the [010] direction. An intra­molecular O—H⋯O hydrogen bond is also present. PMID:22091215

  18. Combining click-multicomponent reaction: one-pot synthesis of triazolyl methoxy-phenyl indazolo[2,1-b]phthalazine-trione derivatives.

    PubMed

    Salehi, Peyman; MaGee, David I; Dabiri, Minoo; Torkian, Laleh; Donahue, Jordan

    2012-05-01

    [(1,2,3-Triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives were synthesized in a simple and efficient method from the one-pot four-component condensation reaction of phthalhydrazide, aromatic propargyloxy aldehydes, active methylene compounds (dimedone and 1,3-cyclohexanedione), and azides in the presence of Cu(OAc)(2)/sodium ascorbate and p-toluenesulfonic acid as catalysts in good to excellent yields.

  19. Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides.

    PubMed

    Daifuku, Stephanie L; Kneebone, Jared L; Snyder, Benjamin E R; Neidig, Michael L

    2015-09-09

    While previous studies have identified FeMes2(SciOPP) as the active catalyst species in iron-SciOPP catalyzed Kumada cross-coupling of mesitylmagnesium bromide and primary alkyl halides, the active catalyst species in cross-couplings with phenyl nucleophiles, where low valent iron species might be prevalent due to accessible reductive elimination pathways, remains undefined. In the present study, in situ Mössbauer and magnetic circular dichroism spectroscopic studies combined with inorganic syntheses and reaction studies are employed to evaluate the in situ formed iron species and identify the active catalytic species in iron-SciOPP catalyzed Suzuki-Miyaura and Kumada cross-couplings of phenyl nucleophiles and secondary alkyl halides. While reductive elimination to form Fe(η(6)-biphenyl)(SciOPP) occurs upon reaction of FeCl2(SciOPP) with phenyl nucleophiles, this iron(0) species is not found to be kinetically competent for catalysis. Importantly, mono- and bis-phenylated iron(II)-SciOPP species that form prior to reductive elimination are identified, where both species are found to be reactive toward electrophile at catalytically relevant rates. The higher selectivity toward the formation of cross-coupled product observed for the monophenylated species combined with the undertransmetalated nature of the in situ iron species in both Kumada and Suzuki-Miyaura reactions indicates that Fe(Ph)X(SciOPP) (X = Br, Cl) is the predominant reactive species in cross-coupling. Overall, these studies demonstrate that low-valent iron is not required for the generation of highly reactive species for effective aryl-alkyl cross-couplings.

  20. Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound

    NASA Astrophysics Data System (ADS)

    El-Gamel, Nadia E. A.; Farghaly, Thoraya A.

    2013-11-01

    Cu(II) (1), Ni(II) (2), Cr(III) (3) and Fe(III) (4) complexes with 3-acetyl-4-benzoyl-1-phenyl-1H-pyrazole (L1) were prepared and structurally characterized. Usual coordination of L1 was achieved through nitrogen of pyrazole moiety and carbonyl acetyl group. Electronic spectra of the complexes indicate that the geometry of the metal center was six coordinate octahedral. In vitro antimicrobial activity of the ligand and complex compounds was screened in terms of antibacterial effect on Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative) and antifungal effect on the fungi Aspergillus flavus and candida albicans using the modified Kirby-Bauer disc diffusion and minimum inhibitory concentrations (MIC) methods. Ni(II) complex (2) exhibited remarkable antifungal inhibition against Candida albicans equal to the standard antifungal agent. To continue our study some structural modifications are formed by adding 4-fluoro-benzoyl moiety to L1 in different forms to produce different ligands, 3-acetyl-4-(4-flourobenzoyl)-1-phenyl-1H-pyrazole (L2) and 3-[(3-acetyl-1-phenyl-1H-4-pyrazolyl)carbonyl]-1-phenyl-4-(4-flourobenzoyl)-1H-pyrazole (L3), Ni complexes (5 and 6) are prepared and comparable in vitro antimicrobial study is evaluated. In vitro cytotoxicity of the Ni(II) complex (2) is studied using MTT assay. The analysis of the cell test showed that (2) displayed quite small cytotoxic response at the higher concentration level which indeed would further enable us for more opportunities in therapeutic and biomedical challenges. Both of the capability as a potent in vitro antifungal agent and the cell test analysis show Ni(II) complex (2) as a promising material in the translation of observed in vitro biological phenomenon into clinical therapies settings.

  1. Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound.

    PubMed

    El-Gamel, Nadia E A; Farghaly, Thoraya A

    2013-11-01

    Cu(II) (1), Ni(II) (2), Cr(III) (3) and Fe(III) (4) complexes with 3-acetyl-4-benzoyl-1-phenyl-1H-pyrazole (L1) were prepared and structurally characterized. Usual coordination of L1 was achieved through nitrogen of pyrazole moiety and carbonyl acetyl group. Electronic spectra of the complexes indicate that the geometry of the metal center was six coordinate octahedral. In vitro antimicrobial activity of the ligand and complex compounds was screened in terms of antibacterial effect on Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative) and antifungal effect on the fungi Aspergillus flavus and candida albicans using the modified Kirby-Bauer disc diffusion and minimum inhibitory concentrations (MIC) methods. Ni(II) complex (2) exhibited remarkable antifungal inhibition against Candida albicans equal to the standard antifungal agent. To continue our study some structural modifications are formed by adding 4-fluoro-benzoyl moiety to L1 in different forms to produce different ligands, 3-acetyl-4-(4-flourobenzoyl)-1-phenyl-1H-pyrazole (L2) and 3-[(3-acetyl-1-phenyl-1H-4-pyrazolyl)carbonyl]-1-phenyl-4-(4-flourobenzoyl)-1H-pyrazole (L3), Ni complexes (5 and 6) are prepared and comparable in vitro antimicrobial study is evaluated. In vitro cytotoxicity of the Ni(II) complex (2) is studied using MTT assay. The analysis of the cell test showed that (2) displayed quite small cytotoxic response at the higher concentration level which indeed would further enable us for more opportunities in therapeutic and biomedical challenges. Both of the capability as a potent in vitro antifungal agent and the cell test analysis show Ni(II) complex (2) as a promising material in the translation of observed in vitro biological phenomenon into clinical therapies settings.

  2. Synthesis of protected (1-phenyl-1h-pyrrol-2-yl)-alkane-1-amines from phenylnitroso Diels-Alder adducts with 1,2-dihydropyridines.

    PubMed

    Berti, Francesco; Di Bussolo, Valeria; Pineschi, Mauro

    2013-07-19

    The reductive cleavage of nitrosobenzene-derived cycloadducts with appropriately protected 1,2-dihydropyridines allows a novel and simple obtainment of substituted N-[1-(1-phenyl-1H-pyrrol-2-yl)alkylamides. This synthesis can also be carried out in a very simple, mild, and practical one-pot procedure without isolation of the corresponding nitrosobenzene cycloadduct by means of catalytic amounts of CuCl.

  3. Synthesis and Characterization of Ferroelectric Liquid Crystalline Organosiloxanes Containing 4-(4-undecanyloxy bi-phenyl-1-carboxyloxy)phenyl (2S,3S)-2-chloro-3-methylvalerate and 4-(4-undecanyloxybenzoyloxy)biphenyl (2S,3S)-2-chloro-3-methylvalerate

    PubMed Central

    Lin, Chih-Hung

    2013-01-01

    A series of new organosiloxane ferroelectric liquid crystalline (FLC) materials have been synthesized, and their mesomorphic and physical properties have been characterized. Four new disiloxanes and trisiloxanes, containing biphenyl 4-hydroxybenzoate and phenyl 4-hydroxybiphenylcarboxylate as mesogenic units and eleven methylene unit as spacers and (2S,3S)-2-chloro-3-methylvalerate unit as chiral end groups. The molecule, using three phenyl ring as a mesogenic unit, formulates much wider liquid crystalline phase temperature ranges than that of a two phenyl ring unit. The phenyl arrangement differences of mesogenic unit result in the greater differences of the liquid crystal phase formation. The siloxane molecule induction is helpful to the more regular smectic phase formation and smectic phase stabilization, such as chiral SC (SC*) and SB phases. The siloxane molecule is helpful to reduce the phase transition temperature and broaden the liquid crystal temperature range of the SC* phase and, simultaneously, it will not induce chain crystallization phenomenon and dilute the Ps value. The synthesis and characterization of the new FLCs materials, which exhibit a room temperature SC* phase and higher spontaneous polarization are presented. PMID:24232576

  4. Murine Motor and Behavior Functional Evaluations for Acute 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine (MPTP) Intoxication

    PubMed Central

    Hutter-Saunders, Jessica A. L.; Mosley, R. Lee

    2011-01-01

    Acute intoxication with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) induces nigrostriatal neurodegeneration that reflects Parkinson’s disease (PD) pathobiology. The model is commonly used for rodent studies of PD pathogenesis and diagnostics and for developmental therapeutics. However, tests of motor function in MPTP-intoxicated mice have yielded mixed results. This unmet need reflects, in part, lesion severity, animal variability, and the overall test sensitivity and specificity. In attempts to standardize rodent motor function and behavioral tests, mice were trained on the rotarod or habituated in an open field test chamber, and baseline performance measurements were collected prior to MPTP intoxication. One week following MPTP intoxication, motor function and behavior were assessed and baseline measurements applied to post-MPTP measurements with normalization to PBS controls. Rotarod and open field tests assessed in this manner demonstrated significant differences between MPTP- and saline-treated mice, while tests of neuromuscular strength and endurance did not. We conclude that the rotarod and open field tests provide reliable measures of motor function for MPTP-intoxicated mice. PMID:21431472

  5. Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors.

    PubMed

    Ha, Young Mi; Park, Yun Jung; Lee, Ji Yeon; Park, Daeui; Choi, Yeon Ja; Lee, Eun Kyeong; Kim, Ji Min; Kim, Jin-Ah; Park, Ji Young; Lee, Hye Jin; Moon, Hyung Ryong; Chung, Hae Young

    2012-02-01

    Herein we describe the design, synthesis and biological activities of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors. The target compounds 2a-2j were designed and synthesized from the structural characteristics of N-phenylthiourea, tyrosinase inhibitor and tyrosine, and l-DOPA, the natural substrates of tyrosinase. Among them, (2R/S,4R)-2-(2,4-dimethoxyphenyl)thiazolidine-4-carboxylic acid (2g) caused the greatest inhibition 66.47% at 20 μM of l-DOPA oxidase activity of mushroom tyrosinase. Kinetic analysis of tyrosinase inhibition revealed that 2g is a competitive inhibitor. We predicted the tertiary structure of tyrosinase, and simulated the docking of mushroom tyrosinase with 2g. These results suggest that the binding affinity of 2g with tyrosinase is high. Also, 2g effectively inhibited tyrosinase activity and reduced melanin levels in B16 cells treated with α-MSH. These data strongly suggest that 2g can suppress the production of melanin via the inhibition of tyrosinase activity.

  6. Growth and characterization of benzaldehyde 4-nitro phenyl hydrazone (BPH) single crystal: A proficient second order nonlinear optical material

    NASA Astrophysics Data System (ADS)

    Saravanan, M.; Abraham Rajasekar, S.

    2016-04-01

    The crystals (benzaldehyde 4-nitro phenyl hydrazone (BPH)) appropriate for NLO appliance were grown by the slow cooling method. The solubility and metastable zone width measurement of BPH specimen was studied. The material crystallizes in the monoclinic crystal system with noncentrosymmetric space group of Cc. The optical precision in the whole visible region was found to be excellent for non-linear optical claim. Excellence of the grown crystal is ascertained by the HRXRD and etching studies. Laser Damage Threshold and Photoluminescence studies designate that the grown crystal contains less imperfection. The mechanical behaviour of BPH sample at different temperatures was investigated to determine the hardness stability of the grown specimen. The piezoelectric temperament and the relative Second Harmonic Generation (for diverse particle sizes) of the material were also studied. The dielectric studies were executed at varied temperatures and frequencies to investigate the electrical properties. Photoconductivity measurement enumerates consummate of inducing dipoles due to strong incident radiation and also divulge the nonlinear behaviour of the material. The third order nonlinear optical properties of BPH crystals were deliberate by Z-scan method.

  7. Spirulina maxima pretreatment partially protects against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity.

    PubMed

    Chamorro, Germán; Pérez-Albiter, Mónica; Serrano-García, Norma; Mares-Sámano, José J; Rojas, Patricia

    2006-01-01

    Spirulina is an alga that has a high nutritional value and some of its biological activities are attributed to the presence of antioxidants. Oxidative stress is involved in Parkinson's disease. This study aims at evaluating the neuroprotective role of Spirulina maxima (Sp.) against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity, used as a model of Parkinson's disease. Ninety-six male C-57 black mice were pretreated with Spirulina for 14 days (25, 50, 100, 150 or 200 mg/kg, oral), followed by three MPTP administrations (30 mg/kg, intraperitoneal, i.p.). Animals were given Sp. for 8 additional days. After the treatment, the striatal dopamine (DA) content was analysed by high performance liquid chromatography, and lipid peroxidation was studied as an index of oxidative stress. Sp. pretreatment at 150 mg/kg partially prevented (51%) the DA-depleting effect of MPTP and blocked oxidative stress. Spirulina partially prevents MPTP neurotoxicity and oxidative stress, suggesting it could be a possible alternative in experimental therapy.

  8. Conformational studies on the four stereoisomers of the novel anticholinergic 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide

    NASA Astrophysics Data System (ADS)

    Oyasu, Hitoshi; Nakanishi, Isao; Tanaka, Akito; Murano, Kenji; Matsuo, Masaaki

    1995-04-01

    To interpret differences in the anticholinergic activity among the four steroisomers of 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide ( 1-4), we performed conformational studies using the semiempirical molecular orbital method. The structures of the global minimum-energy conformations obtained for 1-4, however, could not explain the different activities, particularly in terms of distances between the essential pharmacophores. We thus implemented superimposition studies, using the energetically stable conformations of the most active stereoisomer, 1( 2S,4R), as a template. The energy penalties for a conformation change of the less active stereoisomers 2-4 from their global minimum-energy structure to a new conformation, fitting onto the global minimum-energy conformation of 1, appear to account for the differences in the pharmacological potency better than using the other conformations of 1 as a template. We thus presume that the global minimum-energy conformation of 1 is closely related to the bioactive conformation for these anticholinergics, and also that the pharmacological potency is linked to how readily these substances can change their conformations to fit the muscarinic receptor.

  9. Computational prediction of alpha/beta selectivities in the pyrolysis of oxygen-substituted phenethyl phenyl ethers.

    PubMed

    Beste, Ariana; Buchanan, A C; Harrison, Robert J

    2008-06-05

    Phenethyl phenyl ether (PPE; PhCH 2CH 2OPh) is the simplest model for the most common beta-O-4 linkage in lignin. Previously, we developed a computational scheme to calculate the alpha/beta product selectivity in the pyrolysis of PPE by systematically exploiting error cancellation in the computation of relative rate constants. The alpha/beta selectivity is defined as the selectivity between the competitive hydrogen abstraction reaction paths on the alpha- and beta-carbons of PPE. We use density functional theory and employ transition state theory where we include diagonal anharmonic correction in the vibrational partition functions for low frequency modes for which a semiclassical expression is used. In this work we investigate the effect of oxygen substituents (hydroxy, methoxy) in the para position on the phenethyl ring of PPE on the alpha/beta selectivities. The total alpha/beta selectivity increases when substituents are introduced and is larger for the methoxy than the hydroxy substituent. The strongest effect of the substituents is observed for the alpha-pathway of the hydrogen abstraction by the phenoxyl chain carrying radical for which the rate increases. For the beta pathway and the abstraction by the R-benzyl radical (R = OH,OCH 3) the rate decreases with the introduction of the substituents. These findings are compared with results from recent experimental studies.

  10. Palladium(II) complexes of OS donor N-(di(butyl/phenyl)carbamothioyl)benzamide and their antiamoebic activity.

    PubMed

    Maurya, Mannar R; Uprety, Bhawna; Avecilla, Fernando; Tariq, Saba; Azam, Amir

    2015-06-15

    Two promising palladium(II) compounds of general formula, cis-[Pd(L-O,S)2] [where HL-O,S = N-(di(butyl/phenyl)carbamothioyl)benzamide] as metal based antiamoebic drug candidates, have been synthesized. Both complexes are characterized in the solid state by FT-IR spectroscopy, TGA and single crystal X-ray study, as well as in solution by other spectroscopic techniques such as (1)H and (13)C NMR, and UV-visible. All these studies confirm the coordination of ligands through oxygen and sulphur atoms upon thioenolization induced delocalization. Complexes adopt cis-configuration in the solid state. Both the complexes and their respective ligands were screened in vitro for antiamoebic activity against HM1:1MSS strain of Entamoeba histolytica by microdilution method and cell viability in response to drugs was checked by using MTT assay. The IC50 values in the range 0.30-0.80 μM for ligands as well as complexes compared to 1.40 for metronidazole along with their similar inhibitory effect on cell viability of HEK293 cells like metronidazole make them promising future antiamoebic drugs.

  11. Interaction of SF6 and O2 plasma with porous poly phenyl methyl silsesquioxane low-κ films

    NASA Astrophysics Data System (ADS)

    Cherunilam, J. F.; Rajani, K. V.; Byrne, C.; Heise, A.; McNally, P. J.; Daniels, S.

    2015-04-01

    A reduction in the κ-value of dielectric materials is of great interest today as it leads to the reduction of resistance-capacitance delays and parasitic capacitances within integrated circuits, thereby improving device performance. We have recently reported our studies on the great potential of the Poly phenyl methyl silsesquioxane (PMSQ) low-κ films (κ = 2.7  ±  0.2) for interlayer dielectric applications. Here we report on the deposition and characterisation of porous PMSQ thin films using Heptakis (2,3,6-tri-O-methyl)-β-cyclodextrin as the porogen. A reduction in the κ-value of the films was achieved as a function of the increase in porogen loading in the film. The removal of the thermally liable porogen material from the hybrid films was studied using thermogravimetric analysis (TGA) and Fourier transform infrared spectroscopy (FTIR). The change in density as a function of the porosity was studied using x-ray reflectivity techniques. The interaction of the films with pure SF6 and O2 plasmas was studied and the surface modification that occurs in the films as a result of the interaction was studied using FTIR and x-ray photoelectron spectroscopy. A change in the κ-value of the films was observed after plasma treatment which is attributed to the chemical modification of the film surface due to plasma interaction.

  12. Optimized expression of (S)-carbonyl reductase in Pichia pastoris for efficient production of (S)-1-phenyl-1, 2-ethanediol.

    PubMed

    Zhang, Rongzhen; Xu, Yan; Xiao, Rong; Wang, Lei; Zhang, Botao

    2014-08-01

    The recombinant (S)-carbonyl reductase (SCR) in Escherichia coli catalyzed the reduction of 2-hydroxyacetophenone to (S)-1-phenyl-1,2-ethanediol (PED) with low efficiency. In this work, its 6× histidine fusion gene his6 -scr was cloned in Pichia pastoris under the control of the AOX1 methanol inducible promoter. The heterologous protein SCR was expressed through a Mut(s) phenotype. Under the optimal conditions: pH 7.0, initial OD600 2.5, methanol daily addition concentration 1.0% and induction duration 4-5 days, the recombinant protein SCR was produced at the highest level. The enzyme activity in the cell-free exacts of P. pastoris was 0.38, which was over twofold than that of the recombinant E. coli-SCR. The enzyme was purified to homogeneity with a specific activity of 3.41 U mg(-1) , and it catalyzed the biotransformation of (S)-PED with a high optical purity of 96.9% in a high yield of 89.7% at optimum pH of 7.0. The developed effective system of P. pastoris-SCR will facilitate the preparation of pure chiral alcohol in industry.

  13. DPPC/poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) chimeric nanostructures as potential drug nanocarriers

    NASA Astrophysics Data System (ADS)

    Pippa, Natassa; Kaditi, Eleni; Pispas, Stergios; Demetzos, Costas

    2013-06-01

    In this study, we report on the self assembly behavior and on stability studies of mixed (chimeric) nanosystems consisting of dipalmitoylphosphatidylcholine (DPPC) and poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) (MPOx) gradient copolymer in aqueous media and in fetal bovine serum (FBS). A gamut of light scattering techniques and fluorescence spectroscopy were used in order to extract information on the size and morphological characteristics of the nanoassemblies formed, as a function of gradient block copolymer content, as well as temperature. The hydrodynamic radii ( R h) of nanoassemblies decreased in the process of heating up to 50 °C, while the fractal dimension ( d f) values, also increased. Indomethacin was successfully incorporated into these chimeric nanocarriers. Drug release was depended on the components ratio. The present studies show that there are a number of parameters that can be used in order to alter the properties of chimeric nanosystems, and this is advantageous to the development of "smart" nanocarriers for drug delivery.

  14. Vibrational and electronic absorption spectral studies of 5-amino-1-(4-bromophenyl)-3-phenyl-1-H-pyrazole

    NASA Astrophysics Data System (ADS)

    Prasad, M. V. S.; Chaitanya, Kadali; Udaya Sri, N.; Veeraiah, V.

    2012-12-01

    The FT-IR and FT-Raman spectra of 5-amino-1-(4-bromophenyl)-3-phenyl-1-H-pyrazole have been measured in the regions 4000-400 cm-1 and 3500-100 cm-1, respectively. The equilibrium geometry, bonding features and harmonic vibrational frequencies have been carried out with the help of DFT method. The assignments of the vibrational spectra have been carried out with the normal coordinate analysis (NCA) following the scaled quantum mechanical force field methodology (SQMFF). The first-order hyperpolarizability (β0) and related properties (μ, α0, and Δα) of 5A4BP3PP are calculated by using HF/6-31G(d,p) method on the finite field approach. Stability of the molecule arising from hyperconjugative interactions, charge delocalization have been analyzed using natural bonding orbital (NBO) analysis. The results show that electron density (ED) in the σ* and π* antibonding orbitals and second order delocalization energies E(2) confirms the occurrence of the intramolecular charge transfer (ICT) within the molecule. UV-vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were performed by TDDFT using 6-31G(d,p). The HOMO-LUMO calculations indicating the charge transfer takes place within the molecule.

  15. Synthesis and biological evaluation of 6-fluoro-3-phenyl-7-piperazinyl quinolone derivatives as potential topoisomerase I inhibitors.

    PubMed

    Ge, Raoling; Zhao, Qian; Xie, Zhouling; Lu, Lu; Guo, Qinglong; Li, Zhiyu; Zhao, Li

    2016-10-21

    The design and synthesis of a new series of 6-fluoro-3-phenyl-7-piperazinyl quinolone derivatives, built on the structure of 1-ethyl-3-(6-nitrobenzoxazol-2-yl)-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4(1H)-quinolone, are described. These compounds provide new scaffold for the discovery of Topoisomerase I (Top I) inhibitors and target based assay showed that they can obviously inhibited Top I at 100 μM. The in vitro anti-proliferative activity of these new compounds was evaluated against A549, Hela, BGC-823, and HepG2 cell lines. Compounds 18a-g showed potent inhibitory activity against the growth of those cancer cell lines. The most positive compounds 18f and 18g demonstrated as potent as camptothecin in Top I inhibition assay and MTT assay. Compounds 18f and 18g led to an obvious increase in the percentage of S phase of the cells in 24 h. The in vivo data showed that 18f and 18g inhibited tumor growth with the inhibitory rate of 29.25% and 42.75% at 20 mg/kg, respectively. The data suggested the therapeutic potential for further development.

  16. Spectroscopic studies on binding of 1-phenyl-3-(coumarin-6-yl)sulfonylurea to bovine serum albumin.

    PubMed

    Liu, Xiao-Hui; Xi, Pin-Xian; Chen, Feng-Juan; Xu, Zhi-Hong; Zeng, Zheng-Zhi

    2008-08-21

    The interaction of 1-phenyl-3-(coumarin-6-yl)sulfonylurea (SU22) with bovine serum albumin (BSA) has been investigated by fluorescence quenching spectroscopy combined with UV-absorption, circular dichroism (CD), Fourier transform infrared (FT-IR) spectroscopy techniques under simulative physiological conditions for the first time. Fluorescence data and UV-absorption spectra revealed that the quenching mechanism of fluorescence of BSA by SU22 was a static quenching process and the number of binding sites was about 0.8858; the thermodynamic parameters (DeltaG=-29.23 kJ mol(-1), DeltaH=-47.48 kJ mol(-1), and DeltaS=-61.24 J mol(-1)K(-1)) explained that hydrogen bond and Van der Waals interaction were the main binding force stabilizing the complex. The binding average distance between SU22 and BSA was obtained (3.20 nm) on the basis of the Förster's theory. In addition, The CD spectra and FT-IR spectra have proved that BSA secondary structure changed in the presence of SU22 in aqueous solution.

  17. 3-Heterocycle-phenyl N-alkylcarbamates as FAAH inhibitors: design, synthesis and 3D-QSAR studies.

    PubMed

    Käsnänen, Heikki; Myllymäki, Mikko J; Minkkilä, Anna; Kataja, Antti O; Saario, Susanna M; Nevalainen, Tapio; Koskinen, Ari M P; Poso, Antti

    2010-02-01

    Carbamates are a well-established class of fatty acid amide hydrolase (FAAH) inhibitors. Here we describe the synthesis of meta-substituted phenolic N-alkyl/aryl carbamates and their in vitro FAAH inhibitory activities. The most potent compound, 3-(oxazol-2yl)phenyl cyclohexylcarbamate (2 a), inhibited FAAH with a sub-nanomolar IC(50) value (IC(50)=0.74 nM). Additionally, we developed and validated three-dimensional quantitative structure-activity relationships (QSAR) models of FAAH inhibition combining the newly disclosed carbamates with our previously published inhibitors to give a total set of 99 compounds. Prior to 3D-QSAR modeling, the degree of correlation between FAAH inhibition and in silico reactivity was also established. Both 3D-QSAR methods used, CoMSIA and GRID/GOLPE, produced statistically significant models with coefficient of correlation for external prediction (R(2) (PRED)) values of 0.732 and 0.760, respectively. These models could be of high value in further FAAH inhibitor design.

  18. Pharmacologic Evaluation of Antidepressant Activity and Synthesis of 2-Morpholino-5-phenyl-6H-1,3,4-thiadiazine Hydrobromide

    PubMed Central

    Sarapultsev, Alexey P.; Chupakhin, Oleg N.; Sarapultsev, Petr A.; Sidorova, Larisa P.; Tseitler, Tatiana A.

    2016-01-01

    Substituted thiadiazines exert a reliable therapeutic effect in treating stress, and a schematic description of their ability to influence all aspects of a stress response has been depicted. This study was conducted to pharmacologically evaluate compound L-17, a substituted thiadiazine, (2-morpholino-5-phenyl-6H-1,3,4-thiadiazine, hydrobromide) for possible anti-psychotic/antidepressant activity. Compound L-17 was synthesized by cyclocondensation of α-bromoacetophenone with the original morpholine-4-carbothionic acid hydrazide. Pharmacologic evaluations were conducted using methods described by E.F. Lavretskaya (1985), and in accordance with published guidelines for studying drugs for neuroleptic activity. Compound L-17 was evaluated for various possible mechanisms of action, including its effects on cholinergic system agonists/antagonists, dopaminergic neurotransmission, the adrenergic system, and 5-HT3 serotonin receptors. One or more of these mechanisms may be responsible for the beneficial effects shown by thiadiazine compounds in experiments conducted to evaluate their activity in models of acute stress and acute myocardial infarction. PMID:27213404

  19. Photocatalytic Conversion of CO2 to CO using Rhenium Bipyridine Platforms Containing Ancillary Phenyl or BODIPY Moieties

    SciTech Connect

    Andrade, Gabriel; Pistner, Allen; Yapp, Glenn P. A.; Lutterman, Daniel A; Rosenthal, Joel

    2013-01-01

    Harnessing of solar energy to drive the reduction of carbon dioxide to fuels requires the development of efficient catalysts that absorb sunlight. In this work, we detail the synthesis, electrochemistry and photophysical properties of a set of homologous fac-ReI(CO)3 complexes containing either an ancillary phenyl (8) or BODIPY (12) substituent. These studies demonstrate that both the electronic properties of the rhenium center and BODIPY chromophore are maintained for these systems. Photolysis studies demonstrate that both assemblies 8 and 12 are competent catalysts for the photochemical reduction of CO2 to CO in DMF using triethanolamine (TEOA) as a sacrificial reductant. Both these systems display TOFs for photocatalytic CO production upon irradiation with light ( ex 400 nm) of ~5 hr 1 with TON values of approximately 20. Although structural and photophysical measurements demonstrate that electronic coupling between the BODIPY and fac-ReI(CO)3 units is limited for complex 12, this work clearly shows that the photoactive BODIPY moiety is tolerated during catalysis and does not interfere with the observed photochemistry. When taken together, these results provide a clear roadmap for the development of advanced rhenium bipyridine complexes bearing ancillary BODIPY groups for the efficient photocatalytic reduction of CO2 using visible light.

  20. Natural bond orbital analysis, electronic structure and vibrational spectral analysis of N-(4-hydroxyl phenyl) acetamide: A density functional theory

    NASA Astrophysics Data System (ADS)

    Govindasamy, P.; Gunasekaran, S.; Ramkumaar, G. R.

    2014-09-01

    The Fourier transform infrared (FT-IR) and FT-Raman spectra of N-(4-hydroxy phenyl) acetamide (N4HPA) of painkiller agent were recorded in the region 4000-450 cm-1 and 4000-50 cm-1 respectively. Density functional theory (DFT) has been used to calculate the optimized geometrical parameter, atomic charges, and vibrational wavenumbers and intensity of the vibrational bands. The computed vibrational wave numbers were compared with the FT-IR and FT-Raman experimental data. The computational calculations at DFT/B3LYP level with 6-31G(d,p), 6-31++G(d,p), 6-311G(d,p) and 6-311++G(d,p) basis sets. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using Vibrational energy distribution analysis (VEDA 4) program. The oscillator’s strength calculated by TD-DFT and N4HPA is approach complement with the experimental findings. The NMR chemical shifts 13C and 1H were recorded and calculated using the gauge independent atomic orbital (GIAO) method. The molecular electrostatic potential (MESP) and electron density surfaces of the molecule were constructed. The Natural charges and intermolecular contacts have been interpreted using Natural Bond orbital (NBO) analysis the HOMO-LUMO energy gap has been calculated. The thermodynamic properties like entropy, heat capacity and zero vibrational energy have been calculated.

  1. Natural bond orbital analysis, electronic structure and vibrational spectral analysis of N-(4-hydroxyl phenyl) acetamide: a density functional theory.

    PubMed

    Govindasamy, P; Gunasekaran, S; Ramkumaar, G R

    2014-09-15

    The Fourier transform infrared (FT-IR) and FT-Raman spectra of N-(4-hydroxy phenyl) acetamide (N4HPA) of painkiller agent were recorded in the region 4000-450 cm(-1) and 4000-50 cm(-1) respectively. Density functional theory (DFT) has been used to calculate the optimized geometrical parameter, atomic charges, and vibrational wavenumbers and intensity of the vibrational bands. The computed vibrational wave numbers were compared with the FT-IR and FT-Raman experimental data. The computational calculations at DFT/B3LYP level with 6-31G(d,p), 6-31++G(d,p), 6-311G(d,p) and 6-311++G(d,p) basis sets. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using Vibrational energy distribution analysis (VEDA 4) program. The oscillator's strength calculated by TD-DFT and N4HPA is approach complement with the experimental findings. The NMR chemical shifts 13C and 1H were recorded and calculated using the gauge independent atomic orbital (GIAO) method. The molecular electrostatic potential (MESP) and electron density surfaces of the molecule were constructed. The Natural charges and intermolecular contacts have been interpreted using Natural Bond orbital (NBO) analysis the HOMO-LUMO energy gap has been calculated. The thermodynamic properties like entropy, heat capacity and zero vibrational energy have been calculated.

  2. Labile ruthenium(ii) complexes with extended phenyl-substituted terpyridyl ligands: synthesis, aquation and anticancer evaluation.

    PubMed

    Huang, Huaiyi; Zhang, Pingyu; Chen, Yu; Ji, Liangnian; Chao, Hui

    2015-09-21

    Ruthenium complexes have been considered as promising substitutes for cisplatin in cancer chemotherapy. However, novel ruthenium-based therapies are faced with some limitations, such as unimpressive cytotoxicity toward solid tumors. Herein, we designed and synthesized phenyl-substituted terpyridyl ruthenium(ii) complexes ([Ru(tpy)(bpy)Cl](+) (Ru1), [Ru(phtpy)(bpy)Cl](+) (Ru2) and [Ru(biphtpy)(bpy)Cl](+) (Ru3)) which exhibited distinctly different anticancer activity. Ru1-Ru3 all underwent moderate aquation in buffer solution and this process was significantly inhibited by high chloride concentration. Cancer cells were found to readily uptake the relatively hydrophobic Ru3, as quantified using inductively coupled plasma mass spectrometry (ICP-MS). Ru1 was found to be non-cytotoxic (IC50 > 100 μM) while Ru3 exhibited very promising cytotoxicity on both two-dimensional (2D) cancer cell monolayers and 3D MCTSs. An antiproliferative assay revealed that Ru3 significantly inhibited cellular DNA replication which ultimately induced apoptosis of cancer cells.

  3. Mutagenic and Cytotoxicity LQB 123 Profile: Safety and Tripanocidal Effect of a Phenyl-t-Butylnitrone Derivative.

    PubMed

    Cupello, Mauricio Peixoto; Saraiva, Francis Monique; Ippolito, Pedro; Fernandes, Andréia da Silva; Menna-Barreto, Rubem Figueiredo Sadoko; Costa, Debora de Sousa Dos Santos; Paula, Jessica Isis Oliveira; Costa, Paulo Roberto Ribeiro; Nogueira, Natália Pereira; Felzenswalb, Israel; Dias, Ayres Guimarães; Paes, Marcia Cristina

    2017-01-01

    The therapeutic options for Chagas disease are limited and its treatment presents a number of drawbacks including toxicity, drug resistance, and insufficient effectiveness against the chronic stage of the disease. Therefore, new therapeutical options are mandatory. In the present work, we evaluated the effect of a phenyl-tert-butylnitrone (PBN) derivate, LQB 123, against Trypanosoma cruzi forms. LQB 123 presented a trypanocidal effect against bloodstream trypomastigotes (IC50 = 259.4 ± 6.1 μM) and intracellular amastigotes infecting peritoneal macrophages (IC50 = 188.2 ± 47.5 μM), with no harmful effects upon the mammalian cells (CC50 values greater than 4 mM), resulting in a high selectivity index (CC50/IC50 > 20). Additionally, metacyclic trypomastigotes submitted to LQB 123 presented an IC50 of about 191.8 ± 10.5 μM and epimastigotes forms incubated with different concentrations of LQB 123 presented an inhibition of parasite growth with an IC50 of 255.1 ± 3.6 μM. Finally, we investigated the mutagenic potential of the nitrone by the Salmonella/microsome assay and observed no induction of mutagenicity even in concentrations as high as 33000 μM. Taken together, these results present a nonmutagenic compound, with trypanocidal activity against all relevant forms of T. cruzi, offering new insights into CD treatment suggesting additional in vivo tests.

  4. Mutagenic and Cytotoxicity LQB 123 Profile: Safety and Tripanocidal Effect of a Phenyl-t-Butylnitrone Derivative

    PubMed Central

    Cupello, Mauricio Peixoto; Saraiva, Francis Monique; Ippolito, Pedro; Fernandes, Andréia da Silva; Costa, Debora de Sousa dos Santos; Paula, Jessica Isis Oliveira; Costa, Paulo Roberto Ribeiro; Dias, Ayres Guimarães

    2017-01-01

    The therapeutic options for Chagas disease are limited and its treatment presents a number of drawbacks including toxicity, drug resistance, and insufficient effectiveness against the chronic stage of the disease. Therefore, new therapeutical options are mandatory. In the present work, we evaluated the effect of a phenyl-tert-butylnitrone (PBN) derivate, LQB 123, against Trypanosoma cruzi forms. LQB 123 presented a trypanocidal effect against bloodstream trypomastigotes (IC50 = 259.4 ± 6.1 μM) and intracellular amastigotes infecting peritoneal macrophages (IC50 = 188.2 ± 47.5 μM), with no harmful effects upon the mammalian cells (CC50 values greater than 4 mM), resulting in a high selectivity index (CC50/IC50 > 20). Additionally, metacyclic trypomastigotes submitted to LQB 123 presented an IC50 of about 191.8 ± 10.5 μM and epimastigotes forms incubated with different concentrations of LQB 123 presented an inhibition of parasite growth with an IC50 of 255.1 ± 3.6 μM. Finally, we investigated the mutagenic potential of the nitrone by the Salmonella/microsome assay and observed no induction of mutagenicity even in concentrations as high as 33000 μM. Taken together, these results present a nonmutagenic compound, with trypanocidal activity against all relevant forms of T. cruzi, offering new insights into CD treatment suggesting additional in vivo tests. PMID:28316976

  5. 3, 4-dihydroxyl-phenyl lactic acid restores NADH dehydrogenase 1 α subunit 10 to ameliorate cardiac reperfusion injury.

    PubMed

    Yang, Xiao-Yuan; He, Ke; Pan, Chun-Shui; Li, Quan; Liu, Yu-Ying; Yan, Li; Wei, Xiao-Hong; Hu, Bai-He; Chang, Xin; Mao, Xiao-Wei; Huang, Dan-Dan; Wang, Li-Jun; Hu, Shui-Wang; Jiang, Yong; Wang, Guo-Cheng; Fan, Jing-Yu; Fan, Tai-Ping; Han, Jing-Yan

    2015-06-01

    The present study aimed to detect the role of 3, 4-dihydroxyl-phenyl lactic acid (DLA) during ischemia/reperfusion (I/R) induced myocardial injury with emphasis on the underlying mechanism of DLA antioxidant. Male Spragu-Dawley (SD) rats were subjected to left descending artery occlusion followed by reperfusion. Treatment with DLA ameliorated myocardial structure and function disorder, blunted the impairment of Complex I activity and mitochondrial function after I/R. The results of 2-D fluorescence difference gel electrophoresis revealed that DLA prevented the decrease in NDUFA10 expression, one of the subunits of Complex I. To find the target of DLA, the binding affinity of Sirtuin 1 (SIRT1) to DLA and DLA derivatives with replaced two phenolic hydroxyls was detected using surface plasmon resonance and bilayer interferometry. The results showed that DLA could activate SIRT1 after I/R probably by binding to this protein, depending on phenolic hydroxyl. Moreover, the importance of SIRT1 to DLA effectiveness was confirmed through siRNA transfection in vitro. These results demonstrated that DLA was able to prevent I/R induced decrease in NDUFA10 expression, improve Complex I activity and mitochondrial function, eventually attenuate cardiac structure and function injury after I/R, which was possibly related to its ability of binding to and activating SIRT1.

  6. NBO, conformational, NLO, HOMO-LUMO, NMR and electronic spectral study on 1-phenyl-1-propanol by quantum computational methods

    NASA Astrophysics Data System (ADS)

    Xavier, S.; Periandy, S.; Ramalingam, S.

    2015-02-01

    In this study, FT-IR, FT-Raman, NMR and UV spectra of 1-phenyl-1-propanol, an intermediate of anti-depressant drug fluoxetine, has been investigated. The theoretical vibrational frequencies and optimized geometric parameters have been calculated by using HF and density functional theory with the hybrid methods B3LYP, B3PW91 and 6-311+G(d,p)/6-311++G(d,p) basis sets. The theoretical vibrational frequencies have been found in good agreement with the corresponding experimental data. 1H and 13C NMR spectra were recorded and chemical shifts of the molecule were compared to TMS by using the Gauge-Independent Atomic Orbital (GIAO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy, dipole moment and frontier molecular orbital energies are performed using HF and DFT methods. The thermodynamic properties (heat capacity, entropy and enthalpy) at different temperatures are also calculated. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. The local reactivity of the molecule has been studied using the Fukui function. NLO properties related to polarizability and hyperpolarizability are also discussed.

  7. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyride neurotoxicity is attenuated in mice overexpressing Bcl-2.

    PubMed

    Yang, L; Matthews, R T; Schulz, J B; Klockgether, T; Liao, A W; Martinou, J C; Penney, J B; Hyman, B T; Beal, M F

    1998-10-15

    The proto-oncogene Bcl-2 rescues cells from a wide variety of insults. Recent evidence suggests that Bcl-2 protects against free radicals and that it increases mitochondrial calcium-buffering capacity. The neurotoxicity of 1-methyl-4-phenyl-1,2,3, 6-tetrahydropyride (MPTP) is thought to involve both mitochondrial dysfunction and free radical generation. We therefore investigated MPTP neurotoxicity in both Bcl-2 overexpressing mice and littermate controls. MPTP-induced depletion of dopamine and loss of [3H]mazindol binding were significantly attenuated in Bcl-2 overexpressing mice. Protection was more profound with an acute dosing regimen than with daily MPTP administration over 5 d. 1-Methyl-4-phenylpyridinium (MPP+) levels after MPTP administration were similar in Bcl-2 overexpressing mice and littermates. Bcl-2 blocked MPP+-induced activation of caspases. MPTP-induced increases in free 3-nitrotyrosine levels were blocked in Bcl-2 overexpressing mice. These results indicate that Bcl-2 overexpression protects against MPTP neurotoxicity by mechanisms that may involve both antioxidant activity and inhibition of apoptotic pathways.

  8. A DFT study of the Al₂Cl₆-catalyzed Friedel-Crafts acylation of phenyl aromatic compounds.

    PubMed

    Melissen, Sigismund T A G; Tognetti, Vincent; Dupas, Georges; Jouanneau, Julien; Lê, Guillaume; Joubert, Laurent

    2013-11-01

    The reaction pathways of several Friedel-Crafts acylations involving phenyl aromatic compounds were studied using density functional theory. The reactions were related to the Friedel-Crafts polycondensation of polyaryletherketones. In particular, the acylation of benzene with benzoyl chloride to form benzophenone and variations on this reaction were investigated. The acylation of benzene by one molecule of terephthaloyl chloride or isophthaloyl chloride as well as acylations at the m-, o-, and p-positions of diphenyl ether with one molecule of benzoyl chloride were studied. Adding an additional acyl chloride group to the electrophile appeared to have little influence on the reaction pathway, although the activation energy for the C-C bond-forming steps that occurred when isophthaloyl choride was used was different to the activation energy observed when terephthaloyl chloride was used. Upon changing the nucleophile to diphenyl ether, the reactivity changed according to the trend predicted on based on the o-, p-directing effects of the ether group. The deprotonation step that restored aromaticity varied widely according to the reaction. The rate-determining step in all of the studied reactions was the formation of the acylium ion, followed in importance by either the formation of the Wheland intermediate or the abstraction of hydrogen, depending on the reactivity of the nucleophile.

  9. Electron angular distributions and attachment rates in o-Benzyne and Phenyl aromatic molecules: the effect of the permanent dipoles

    NASA Astrophysics Data System (ADS)

    Carelli, Fabio; Gianturco, Franco A.

    2013-12-01

    Free, gas-phase polycyclic aromatic hydrocarbons (PAHs) and related species are currently considered to play an important role in the interstellar/circumstellar medium as they are thought to significantly contribute to both Diffuse and Unidentified infrared interstellar bands. They are also considered fundamental blocks of the interstellar dust and several formation mechanisms were proposed with regard to their interstellar/circumstellar synthesis. In this paper we therefore present and discuss the results obtained from ab initio quantum scattering calculations of the response from neutral polar aromatic single-ring species to low-energies electron collisions. Our main purpose is here to provide new values for the rate constants for electron attachment to orthobenzyne and to phenyl molecules by discussing in detail the effects of the long-range dipole interaction in the framework of the Born perturbative approximation at the first order. We shall further discuss the specific behavior of the electrons' diffusion by such molecules, especially in the low-energy range of the scattered particles' energies as guided by their permanent dipole moments. We shall also provide accurate numerical fittings for both rates and give explicitly the fitting parameters for their possible use in evolutionary models.

  10. Phenyl Ether- and Aniline-Containing 2-Aminoquinolines as Potent and Selective Inhibitors of Neuronal Nitric Oxide Synthase.

    PubMed

    Cinelli, Maris A; Li, Huiying; Pensa, Anthony V; Kang, Soosung; Roman, Linda J; Martásek, Pavel; Poulos, Thomas L; Silverman, Richard B

    2015-11-12

    Excess nitric oxide (NO) produced by neuronal nitric oxide synthase (nNOS) is implicated in neurodegenerative disorders. As a result, inhibition of nNOS and reduction of NO levels is desirable therapeutically, but many nNOS inhibitors are poorly bioavailable. Promising members of our previously reported 2-aminoquinoline class of nNOS inhibitors, although orally bioavailable and brain-penetrant, suffer from unfavorable off-target binding to other CNS receptors, and they resemble known promiscuous binders. Rearranged phenyl ether- and aniline-linked 2-aminoquinoline derivatives were therefore designed to (a) disrupt the promiscuous binding pharmacophore and diminish off-target interactions and (b) preserve potency, isoform selectivity, and cell permeability. A series of these compounds was synthesized and tested against purified nNOS, endothelial NOS (eNOS), and inducible NOS (iNOS) enzymes. One compound, 20, displayed high potency, selectivity, and good human nNOS inhibition, and retained some permeability in a Caco-2 assay. Most promisingly, CNS receptor counterscreening revealed that this rearranged scaffold significantly reduces off-target binding.

  11. Quantum-chemical, NMR and X-ray diffraction studies on (+/-)-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane.

    PubMed

    Zapata-Torres, Gerald; Cassels, Bruce K; Parra-Mouchet, Julia; Mascarenhas, Yvonne P; Ellena, Javier; De Araujo, A S

    2008-06-01

    Time-averaged conformations of (+/-)-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane hydrochloride (MDMA, "ecstasy") in D(2)O, and of its free base and trifluoroacetate in CDCl(3), were deduced from their (1)H NMR spectra and used to calculate their conformer distribution. Their rotational potential energy surface (PES) was calculated at the RHF/6-31G(d,p), B3LYP/6-31G(d,p), B3LYP/cc-pVDZ and AM1 levels. Solvent effects were evaluated using the polarizable continuum model. The NMR and theoretical studies showed that, in the free base, the N-methyl group and the ring are preferentially trans. This preference is stronger in the salts and corresponds to the X-ray structure of the hydrochloride. However, the energy barriers separating these forms are very low. The X-ray diffraction crystal structures of the anhydrous salt and its monohydrate differed mainly in the trans or cis relationship of the N-methyl group to the alpha-methyl, although these two forms interconvert freely in solution.

  12. Methyl 3-[3',4'-(methylenedioxy)phenyl]-2-methyl glycidate: an ecstasy precursor seized in Sydney, Australia.

    PubMed

    Collins, Michael; Heagney, Aaron; Cordaro, Frank; Odgers, David; Tarrant, Gregory; Stewart, Samantha

    2007-07-01

    Five 44 gallon drums labeled as glycidyl methacrylate were seized by the Australian Customs Service and the Australian Federal Police at Port Botany, Sydney, Australia, in December 2004. Each drum contained a white, semisolid substance that was initially suspected to be 3,4-methylenedioxymethylamphetamine (MDMA). Gas chromatography-mass spectroscopy (GC/MS) analysis demonstrated that the material was neither glycidyl methacrylate nor MDMA. Because intelligence sources employed by federal agents indicated that this material was in some way connected to MDMA production, suspicion fell on the various MDMA precursor chemicals. Using a number of techniques including proton nuclear magnetic resonance spectroscopy ((1)H NMR), carbon nuclear magnetic resonance spectroscopy ((13)C NMR), GC/MS, infrared spectroscopy, and total synthesis, the unknown substance was eventually identified as methyl 3-[3',4'(methylenedioxy)phenyl]-2-methyl glycidate. The substance was also subjected to a published hydrolysis and decarboxylation procedure and gave a high yield of the MDMA precursor chemical, 3,4-methylenedioxyphenyl-2-propanone, thereby establishing this material as a "precursor to a precursor."

  13. Photo- and thermal-oxidation studies on methyl and phenyl linoleate: anti-oxidant behaviour and rates of reaction.

    PubMed

    Chacón, J N; Gaggini, P; Sinclair, R S; Smith, F J

    2000-09-01

    Photo-peroxidation of methyl and phenyl linoleate in methanol solutions at 25 degrees C, in the presence of methylene blue or 5,10,15,20-tetra(4-pyridyl)-porphyrin (TPP) as sensitisers of singlet oxygen, was found to proceed at more than 30 times the rate of the same polyunsaturated fatty acid (PUFA) ester species undergoing thermal-peroxidation in the bulk phase at 50 degrees C. The addition of anti-oxidants such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) quench the thermal-oxidation effectively but appear to only partially inhibit the photosensitized peroxidation reactions. The kinetics of the overall peroxidation reactions were followed by ultraviolet spectroscopy, measurements of hydroperoxide concentration and by high performance liquid chromatography (HPLC). The photo-peroxidation reaction proceeds more rapidly in chloroform solution as the lifetime of singlet oxygen is shown to be over ten times longer in chloroform than methanol. The initial fast reaction kinetics of the photo-peroxidation reactions were evaluated using a pulsed laser technique to show that singlet oxygen reacts competitively with both the anti-oxidants and the polyunsaturated fatty acid ester. Second order kinetic rate constants (in the range 10(5)-10(7) dm(3) mol(-1) s(-1)) were evaluated for the reactivity of singlet oxygen with a range of anti-oxidants and a singlet oxygen quencher, and the results used to explain the effect of anti-oxidants at different concentrations on the rate of the linoleate photo-peroxidation reaction.

  14. Measurement of Large Dipolar Couplings of a Liquid Crystal with Terminal Phenyl Rings and Estimation of the Order Parameters.

    PubMed

    Kumar, R V Sudheer; Ramanathan, Krishna V

    2015-07-20

    NMR spectroscopy is a powerful means of studying liquid-crystalline systems at atomic resolutions. Of the many parameters that can provide information on the dynamics and order of the systems, (1) H-(13) C dipolar couplings are an important means of obtaining such information. Depending on the details of the molecular structure and the magnitude of the order parameters, the dipolar couplings can vary over a wide range of values. Thus the method employed to estimate the dipolar couplings should be capable of estimating both large and small dipolar couplings at the same time. For this purpose, we consider here a two-dimensional NMR experiment that works similar to the insensitive nuclei enhanced by polarization transfer (INEPT) experiment in solution. With the incorporation of a modification proposed earlier for experiments with low radio frequency power, the scheme is observed to enable a wide range of dipolar couplings to be estimated at the same time. We utilized this approach to obtain dipolar couplings in a liquid crystal with phenyl rings attached to either end of the molecule, and estimated its local order parameters.

  15. Poly(vinyl chloride) blend with biodegradable cellulose acetate in presence of N-(phenyl amino) maleimides.

    PubMed

    Abdel-Naby, Abir S; Al-Ghamdi, Azza A

    2014-09-01

    Wider plastic applications of poly(vinyl chloride) (PVC) has raised serious problem to the environment. Since (PVC) waste products resist biodegradation and persist in the environment for longer time. The object of this study is to blend (PVC) with biodegradable cellulose acetate to thermally support the polymer during the molding process as well as to enhance the biodegradability of (PVC) waste products. Blending of poly(vinyl chloride) and cellulose acetate (CA) in presence of N-(phenyl amino) maleimides (R-PhAM) where (R=H, 4-NO2) led to improvement in the thermal stability of the blend film at high temperatures as shown from the high values of initial decomposition temperature (To) determined from their thermogravimetry (TG) curves. Also, blending (PVC) with (CA) led to improvement in the mechanical properties of the blend films as compared to (PVC). The crystalline regions of cellulose acetate enhanced the elasticity of the blend films as shown from their high Young's modulus values.

  16. 1-(5-Bromo-4-phenyl-1,3-thia­zol-2-yl)pyrrolidin-2-one

    PubMed Central

    Ghabbour, Hazem A.; Kadi, Adnan A.; El-Subbagh, Hussein I.; Chia, Tze Shyang; Fun, Hoong-Kun

    2012-01-01

    The asymmetric unit of the title compound, C13H11BrN2OS, consists of two crystallographically independent mol­ecules (A and B). In each mol­ecule, the pyrrolidine ring adopts an envelope conformation with a methyl­ene C atom as the flap atom. In mol­ecule A, the central thia­zole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in mol­ecule B. The pyrrolidine ring is slightly twisted from the thia­zole ring, with C—N—C—N torsion angles of 4.8 (3) and 3.0 (4)° in mol­ecules A and B, respectively. In the crystal, C—H⋯π and π–π [centroid-to-centroid distance = 3.7539 (14) Å] inter­actions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5). PMID:22719524

  17. Probing the intrapore surface of phenyl-substituted nanoscale mesoporous silica-piezoelectric sorption measurements in thin films.

    PubMed

    Darga, Alexander; Kecht, Johann; Bein, Thomas

    2007-12-18

    The incorporation of organic moieties into siliceous frameworks leads to a wide variety of adsorbate-adsorbent interactions including weak van-der-Waal attractions as well as strong interactions such as Coulomb forces. Depending on the desired properties of such substituted highly porous matrix materials, optimized synthesis routes can be established to enhance the desired internal pore surface-affinity toward certain volatile compounds. On the basis of a fundamental knowledge of the host-guest system, sorption-related applications may benefit from individually fine-tuned and modified sample materials. The sorption isotherms of vaporized toluene on nonmodified and phenyl-functionalized mesoporous silica samples were determined on an acoustic wave device at different temperatures. The mesoporous silica was modified by in situ co-condensation and postsynthesis grafting approaches, respectively. All samples were thoroughly characterized by nitrogen sorption, thermogravimetric analysis (TGA), scanning and transmission electron microscopy (SEM, TEM), solid-state nuclear magnetic resonance (29Si NMR), dynamic light scattering (DLS), Raman spectroscopy, and toluene adsorption on a quartz crystal microbalance (QCM). The different heats of adsorption of toluene on the various modified silica surfaces obtained by the sorption data make it possible to gain additional information about the degree and type of surface functionalization. It is thus demonstrated that QCM studies can be a powerful and convenient tool for efficient investigations of functionalized mesoporous silica particles that yield valuable quantitative information on molecule-surface interactions.

  18. Excited state proton transfer in di-(2-hydroxy-3-formyl-5-tert butyl phenyl) methane and solvent effect.

    PubMed

    Mukhopadhyay, M; Banerjee, D; Mukherjee, S

    2006-05-15

    The proton transfer reaction and the spectroscopic properties of di-(2-hydroxy-3-formyl-5-tert butyl phenyl) methane (HFPM) have been examined in different nonpolar and polar solvents at room temperature and 77 K, by means of absorption, emission and time resolved fluorescence spectroscopy. In the ground state, the primary closed form has been identified in all the nonpolar and polar solvents and the anion is detected only in presence of base in some of the polar solvents. After photoexcitation, the excited state intramolecular proton transfer (ESIPT) is indicated by a large Stokes shifted emission (approximately 10,600 cm-1) in all the nonpolar and polar solvents used, except in water and ethylene glycol (EG). The ESIPT band is likely to be originated from the enol tautomer of the HFPM. Two types of anion and H-bonded complex have been detected in the excited state. In water and EG, only anion and H-bonded complex have been detected in the excited state. At 77 K, HFPM shows phosphorescence in pure ethanol, and in n-hexane in presence of triethylamine. It has been suggested that the appearance of phosphorescence is due to the rotation of the formyl group. The measured nonradiative decay rates have always been found to dominate in the decay processes of the excited state of HFPM. Some semiempirical calculations have been undertaken to rationalize the experimental findings.

  19. Observation of transient alignment-inversion walls in nematics of phenyl benzoates in the presence of a magnetic field.

    PubMed

    Hinov, Hristo P; Vistin', Leonard K; Marinov, Yordan G

    2014-04-17

    Formation of new transient walls by a constant magnetic field at the Fréedericsz critical value has been observed. They are oriented along the initial alignment of the nematic phase of phenyl benzoates and appeared only in relatively thick samples with a thickness between 50 and 100 μm of the cells. The excellent planarity of the liquid crystal orientation is considered to be the most important condition for their presence These magnetic walls are transient as they disappear either after a few seconds for 100 μm thick nematic cells or after parts of a second for thinner (50 μm) nematic cells. Nonregular stable magnetic walls, incorporating disclinations with core, appear immediately after the relaxation of the transient walls, when the planarity of the nematic orientation is not perfect. In thinner nematic cells of 20 μm or less, a Fréedericksz transition has only been observed. The formation of transient magnetic walls can be described by a model taking into account alignment-inversion, twisted along Y regions. The transient walls accompanied by a system of Becke lines relax by going through three-dimensional twist-splay-bend deformations.

  20. Three coordination polymers constructed from 5-(4-(tetrazol-5-yl)phenyl)isophthalic acid: Synthesis, crystal structure and properties

    NASA Astrophysics Data System (ADS)

    Zhai, Dandan; Sun, Wujuan; Fan, Fei; Liao, Xuzhao; Chen, Sanping; Yang, Xuwu

    2017-04-01

    Three new coordination polymers, namely, {[Co2(TPA)(μ3-O)3]·0.5DMA}n (1), {[Co(H2TPA)(bibp)(H2O)3]·H2O}n (2) and {[Cd3(TPA)2(phen)4]·4H2O}n (3), (H3TPA = 5-(4-(tetrazol-5-yl)phenyl)isophthalic acid, bibp = 4,4'-bis(imidazolyl)biphenyl, phen = 1,10-phenanthroline and DMA = N,N-dimethylacetamide), have been synthesized under solvothermal conditions and structurally characterized by elemental analysis, IR spectroscopy, powder X-ray diffraction (PXRD) and single-crystal X-ray diffraction analysis. Polymer 1 exhibits a three-dimensional (3D) structure constructed from 5-connected secondary building units (SBUs) [Co3(μ3-O)] and 3-connected H3TPA ligands. Polymer 2 has a 1D zigzag polymer chain connected by H3TPA and bibp ligands. Polymer 3 features an unusual 3D framework with a (3,4,2)-connected {4; 6;8}{4; 62;83} topology. Moreover, the thermal stabilities of 1-3 and photoluminescence properties of 3 have been investigated. Magnetic susceptibility measurements indicate that polymers 1-2 display antiferromagnetic exchange properties.

  1. 3-(Adamantan-1-yl)-4-ethyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione

    PubMed Central

    El-Emam, Ali A.; Al-Abdullah, Ebtehal S.; Al-Tuwaijri, Hanaa M.; Said-Abdelbaky, Mohammed; García-Granda, Santiago

    2012-01-01

    The title compound, C25H35N5S, has an approximately C-shaped conformation. The dihedral angle between the triazole and phenyl planes is 79.5 (2)°. The crystal structure consists of infinite chains parallel to the b axis, constructed by C—H⋯S hydrogen bonds between translation-related mol­ecules. Adjacent chains are linked via weak C—H⋯C inter­actions between the adamantyl and phenyl groups. PMID:22904841

  2. Highly efficient bioreduction of 2-hydroxyacetophenone to (S)- and (R)-1-phenyl-1,2-ethanediol by two substrate tolerance carbonyl reductases with cofactor regeneration.

    PubMed

    Cui, Zhi-Mei; Zhang, Jian-Dong; Fan, Xiao-Jun; Zheng, Gao-Wei; Chang, Hong-Hong; Wei, Wen-Long

    2017-02-10

    Optically pure 1-phenyl-1,2-ethanediol is a very important chiral building block and intermediate in fine chemical and pharmaceutical industries. Reduction of 2-hydroxyacetophenone provides a straightforward approach to access these important compounds. In this study, two enantiocomplementary carbonyl reductases, BDHA (2,3-butanediol dehydrogenase from Bacillus subtilis) and GoSCR (polyol dehydrogenase from Gluconobacter oxydans) were discovered for the first time to convert 2-hydroxyacetophenone (2-HAP) to (R)-1-phenyl-1,2-ethanediol ((R)-PED) and (S)-1-phenyl-1,2-ethanediol ((S)-PED) with excellent stereochemical selectivity, respectively. The two enzymes were purified and characterized. In vitro bioreduction of 2-HAP catalyzed by BDHA and GoSCR coupled with glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration were demonstrated, affording both (R)-PED and (S)-PED in>99% ee and 99% conversion. Recombinant Escherichia coli whole cells co-expressing both GDH and BDHA or GoSCR genes were used to asymmetric reduction of 2-HAP to (R)-PED or (S)-PED. Under the optimized conditions, the bioreduction of 400mM (54g/L) substrate was proceeded smoothly without the external addition of cofactor, and the product (R)-PED and (S)-PED were obtained with 99% yield, >99% ee and 18.0g/L/h volumetric productivity. These results offer a practical biocatalytic method for the preparation of both (R)-PED and (S)-PED with high volumetric productivity.

  3. Novel near-IR absorbing phenyl-substituted phthalo- and naphthalocyanine complexes of lanthanide(III): synthesis and spectral and electrochemical properties.

    PubMed

    Dubinina, Tatiana V; Paramonova, Kseniya V; Trashin, Stanislav A; Borisova, Nataliya E; Tomilova, Larisa G; Zefirov, Nikolay S

    2014-02-21

    A series of novel phenyl-substituted planar and sandwich-type complexes of Eu, Er and Lu with phthalo and naphthalocyanine ligands was obtained. A successful synthesis of dinaphthalocyanines from the ligand is described. A selective synthetic approach to the phenyl-substituted triphthalocyanine complexes from the ligand and acetylacetonate salts of lanthanides was developed. Correlations between the ionic radii of the central metal and absorption maxima were obtained for sandwich-type complexes. It was found that intervalence (IV) bands for dinaphthalocyanine complexes were red-shifted about 200 nm in comparison with corresponding diphthalocyanines, reaching 1797 nm for the Eu complex. The electrochemical behaviour of planar and sandwich-type Lu complexes was investigated. For the first time a spectroelectrochemical study of multistep reduction and oxidation processes for a triple-decker complex was carried out using the example of the triphthalocyanine of Lu. The structures of the compounds obtained were determined by (1)H NMR and high resolution MALDI TOF/TOF. The first single-crystal structure for an aryl-substituted double-decker complex was described using the example of the diphthalocyanine of Lu, showing the presence of intramolecular π-π interactions between phenyl groups.

  4. QSPR models of n-octanol/water partition coefficients and aqueous solubility of halogenated methyl-phenyl ethers by DFT method.

    PubMed

    Zeng, Xiao-Lan; Wang, Hong-Jun; Wang, Yan

    2012-02-01

    The possible molecular geometries of 134 halogenated methyl-phenyl ethers were optimized at B3LYP/6-31G(*) level with Gaussian 98 program. The calculated structural parameters were taken as theoretical descriptors to establish two new novel QSPR models for predicting aqueous solubility (-lgS(w,l)) and n-octanol/water partition coefficient (lgK(ow)) of halogenated methyl-phenyl ethers. The two models achieved in this work both contain three variables: energy of the lowest unoccupied molecular orbital (E(LUMO)), most positive atomic partial charge in molecule (q(+)), and quadrupole moment (Q(yy) or Q(zz)), of which R values are 0.992 and 0.970 respectively, their standard errors of estimate in modeling (SD) are 0.132 and 0.178, respectively. The results of leave-one-out (LOO) cross-validation for training set and validation with external test sets both show that the models obtained exhibited optimum stability and good predictive power. We suggests that two QSPR models derived here can be used to predict S(w,l) and K(ow) accurately for non-tested halogenated methyl-phenyl ethers congeners.

  5. Synthesis, spectroscopic characterization and DFT calculations of monohydroxyalkylated derivatives of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione

    NASA Astrophysics Data System (ADS)

    Szyszkowska, Agnieszka; Hęclik, Karol; Trzybiński, Damian; Woźniak, Krzysztof; Klasek, Antonin; Zarzyka, Iwona

    2017-01-01

    Synthesis of new derivatives with an imidazo[1,5-c]quinazoline-3,5-dione ring has been presented. Two new alcohols with the imidazo[1,5-c]quinazoline-3,5-dione ring were obtained and characterized by spectral (1H, 13C NMR, IR and UV) and crystallography methods. A reaction chemoselectivity has been observed with a formation of monohydroxyalkyl derivatives of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione substituted at the 2. nitrogen atom. The absence of derivatives substituted at the 6. nitrogen atom was proven experimentally. The synthesis with chemoselectivity over 99% without control of the substituent effect happens very rarely. The HOMO-LUMO mappings are reported which reveals the different charge transfer possibilities within the molecule of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione in the region of the 2. and the 6. nitrogen atoms. Quantum-mechanical DFT calculations proved to be very useful to explain the reason of selectivity reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with oxiranes.

  6. Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships.

    PubMed

    Fortin, Sébastien; Wei, Lianhu; Moreau, Emmanuel; Lacroix, Jacques; Côté, Marie-France; Petitclerc, Eric; Kotra, Lakshmi P; Gaudreault, René C

    2011-11-01

    The importance of the bridge linking the two phenyl moieties of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) was assessed using a sulfonamide group, which is a bioisostere of sulfonate and ethenyl groups. Forty one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide (PIB-SA) derivatives were prepared and biologically evaluated. PIB-SAs exhibit antiproliferative activities at the nanomolar level against sixteen cancer cell lines, block the cell cycle progression in G(2)/M phase, leading to cytoskeleton disruption and anoikis. These results were subjected to CoMFA and CoMSIA analyses to establish quantitative structure-activity relationships. These results evidence that the sulfonate and sulfonamide moieties are reciprocal bioisosteres and that phenylimidazolidin-2-one could mimic the trimethoxyphenyl moiety found in the structure of numerous potent antimicrotubule agents. Finally, compounds 16 and 17 exhibited potent antitumor and antiangiogenic activities on HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membrane similar to CA-4 without significant toxicity for the chick embryos, making this class of compounds a promising class of anticancer agents.

  7. Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases.

    PubMed

    Singh, A K; Pandey, O P; Sengupta, S K

    2012-01-01

    New Zn(II) complexes have been synthesized by the reactions of zinc(II) acetate with Schiff bases derived from 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde, 2-hydroxyacetophenone or indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non-electrolytes. Elemental analyses suggest that the complexes have 1:1 stoichiometry of the type [ZnL(H(2)O)(2)], [ZnL'(OAc)(2)(H(2)O)(2)] (L=dianionic Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and 2-hydroxyacetophenone or indoline-2,3-dione; L'=neutral Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde) and they were characterized by FT-IR, (1)H NMR, (13)C NMR and FAB mass. All these Schiff bases and their complexes have also been screened for their antibacterial activities against Bacillus subtilis, Escherichia coli and antifungal activities against Colletotrichum falcatum, Aspergillus niger, Fusarium oxysporium and Carvularia pallescence by petriplates methods.

  8. Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases

    NASA Astrophysics Data System (ADS)

    Singh, A. K.; Pandey, O. P.; Sengupta, S. K.

    New Zn(II) complexes have been synthesized by the reactions of zinc(II) acetate with Schiff bases derived from 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde, 2-hydroxyacetophenone or indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non-electrolytes. Elemental analyses suggest that the complexes have 1:1 stoichiometry of the type [ZnL(H 2O) 2], [ZnL'(OAc) 2(H 2O) 2] (L = dianionic Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and 2-hydroxyacetophenone or indoline-2,3-dione; L' = neutral Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde) and they were characterized by FT-IR, 1H NMR, 13C NMR and FAB mass. All these Schiff bases and their complexes have also been screened for their antibacterial activities against Bacillus subtilis, Escherichia coli and antifungal activities against Colletotrichum falcatum, Aspergillus niger, Fusarium oxysporium and Carvularia pallescence by petriplates methods.

  9. Antimicrobial screening and one-pot synthesis of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives

    PubMed Central

    Goel, Neelima; Drabu, Sushma; Afzal, Obaid; Bawa, Sandhya

    2014-01-01

    Aim: Synthesis of series of 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a–4k) and their in vitro antifungal and antibacterial screening. Materials and Methods: A series of compounds (4a–4k) was synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent. The reaction was carried out in anhydrous methanol under neutral conditions at room temperature. The structures of synthesized compounds (4a–4k) were established on the basis of IR, 1H and 13C-NMR, and mass spectral data. Results: All 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a–4k) were tested in vitro for antifungal and antibacterial activities against different fungal and bacterial strains. Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains. Conclusion: In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7–58.9). PMID:25400408

  10. [N-Benzyl-N-(2-phenyl-eth-yl)di-thio-carbamato-κ(2)S,S']tri-phenyl-tin(IV) and [bis-(2-meth-oxy-eth-yl)di-thio-carbamato-κ(2)S,S']tri-phenyl-tin(IV): crystal structures and Hirshfeld surface analysis.

    PubMed

    Mohamad, Rapidah; Awang, Normah; Kamaludin, Nurul Farahana; Jotani, Mukesh M; Tiekink, Edward R T

    2016-10-01

    The crystal and mol-ecular structures of two tri-phenyl-tin di-thio-carbamates, [Sn(C6H5)3(C16H16NS2)], (I), and [Sn(C6H5)3(C7H14NO2S2)], (II), are described. In (I), the di-thio-carbamate ligand coordinates the Sn(IV) atom in an asymmetric manner, leading to a highly distorted trigonal-bipyramidal coordination geometry defined by a C3S2 donor set with the weakly bound S atom approximately trans to one of the ipso-C atoms. A similar structure is found in (II), but the di-thio-carbamate ligand coordinates in an even more asymmetric fashion. The packing in (I) features supra-molecular chains along the c axis sustained by C-H⋯π inter-actions; chains pack with no directional inter-actions between them. In (II), supra-molecular layers are formed, similarly sustained by C-H⋯π inter-actions; these stack along the b axis. An analysis of the Hirshfeld surfaces for (I) and (II) confirms the presence of the C-H⋯π inter-actions but also reveals the overall dominance of H⋯H contacts in the respective crystals.

  11. [N-Benzyl-N-(2-phenyl­eth­yl)di­thio­carbamato-κ2 S,S′]tri­phenyl­tin(IV) and [bis­(2-meth­oxy­eth­yl)di­thio­carbamato-κ2 S,S′]tri­phenyl­tin(IV): crystal structures and Hirshfeld surface analysis

    PubMed Central

    Mohamad, Rapidah; Awang, Normah; Kamaludin, Nurul Farahana; Jotani, Mukesh M.; Tiekink, Edward R. T.

    2016-01-01

    The crystal and mol­ecular structures of two tri­phenyl­tin di­thio­carbamates, [Sn(C6H5)3(C16H16NS2)], (I), and [Sn(C6H5)3(C7H14NO2S2)], (II), are described. In (I), the di­thio­carbamate ligand coordinates the SnIV atom in an asymmetric manner, leading to a highly distorted trigonal–bipyramidal coordination geometry defined by a C3S2 donor set with the weakly bound S atom approximately trans to one of the ipso-C atoms. A similar structure is found in (II), but the di­thio­carbamate ligand coordinates in an even more asymmetric fashion. The packing in (I) features supra­molecular chains along the c axis sustained by C—H⋯π inter­actions; chains pack with no directional inter­actions between them. In (II), supra­molecular layers are formed, similarly sustained by C—H⋯π inter­actions; these stack along the b axis. An analysis of the Hirshfeld surfaces for (I) and (II) confirms the presence of the C—H⋯π inter­actions but also reveals the overall dominance of H⋯H contacts in the respective crystals. PMID:27746946

  12. Polystyrene bound oxidovanadium(IV) and dioxidovanadium(V) complexes of histamine derived ligand for the oxidation of methyl phenyl sulfide, diphenyl sulfide and benzoin.

    PubMed

    Maurya, Mannar R; Arya, Aarti; Kumar, Amit; Pessoa, João Costa

    2009-03-28

    Ligand Hsal-his (I) derived from salicylaldehyde and histamine has been covalently bound to chloromethylated polystyrene cross-linked with 5% divinylbenzene. Upon treatment with [VO(acac)(2)] in DMF, the polystyrene-bound ligand (abbreviated as PS-Hsal-his, II) gave the stable polystyrene-bound oxidovanadium(iv) complex PS-[V(IV)O(sal-his)(acac)] , which upon oxidation yielded the dioxidovanadium(v) PS-[V(V)O(2)(sal-his)] complex. The corresponding non polymer-bound complexes [V(IV)O(sal-his)(acac)] and [V(V)O(2)(sal-his)] have also been obtained. These complexes have been characterised by IR, electronic, (51)V NMR and EPR spectral studies, and thermal as well as scanning electron micrograph studies. Complexes and have been used as a catalyst for the oxidation of methyl phenyl sulfide, diphenyl sulfide and benzoin with 30% H(2)O(2) as oxidant. Under the optimised reaction conditions, a maximum of 93.8% conversion of methyl phenyl sulfide with 63.7% selectivity towards methyl phenyl sulfoxide and 36.3% towards methyl phenyl sulfone has been achieved in 2 h with 2 . Under similar conditions, diphenyl sulfide gave 83.4% conversion where selectivity of reaction products varied in the order: diphenyl sulfoxide (71.8%) > diphenyl sulfone (28.2%). A maximum of 91.2% conversion of benzoin has been achieved within 6 h, and the selectivities of reaction products are: methylbenzoate (37.0%) > benzil (30.5%) > benzaldehyde-dimethylacetal (22.5%) > benzoic acid (8.1%). The PS-bound complex, 1 exhibits very comparable catalytic potential. These polymer-anchored heterogeneous catalysts do not leach during catalytic action, are recyclable and show higher catalytic activity and turnover frequency than the corresponding non polymer-bound complexes. EPR and (51)V NMR spectroscopy was used to characterise methanolic solutions of 3 and 4 and to identify species formed upon addition of H(2)O(2) and/or acid and/or methyl phenyl sulfide.

  13. Optical and THz reflectance investigations of organic solar cells

    NASA Astrophysics Data System (ADS)

    Sporea, Dan; Mihai, Laura; Sporea, Adelina; Galagan, Yulia

    2016-04-01

    Two Organic Photovoltaic devices having a photoactive layer containing Poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5- (4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) and [6,6]-phenyl C61-butyric acid methyl ester (PCBM, 99%), and the layer sequences - glass/ITO/ZnO/PAL/PEDOT:PSS/Ag/encapsulation were non-destructively investigated by diffuse optical spectral reflectance, THz spectroscopy and THz imaging. The proposed methods proved to be powerful tools to support quality assurance in organic solar cells development, facilitating both the localization of manufacturing defects and the device degradation, as they are combined with "classical" evaluation means.

  14. Air-stable platinum and palladium complexes featuring bis[2,4-bis(trifluoromethyl)phenyl]phosphinous acid ligands.

    PubMed

    Kurscheid, Boris; Neumann, Beate; Stammler, Hans-Georg; Hoge, Berthold

    2011-12-23

    Secondary phosphane oxides, R(2)P(O)H, are commonly used as preligands for transition-metal complexes of phosphinous acids, R(2)P-OH (R=alkyl, aryl), which are relevant as efficient catalysts in cross-coupling processes. In contrast to previous work by other groups, we are interested in the ligating properties of an electron-deficient phosphinous acid, (R(f))(2)P-OH, bearing the strongly electron-withdrawing and sterically demanding 2,4-bis(trifluoromethyl)phenyl group towards catalysis-relevant metals, such as palladium and platinum. The preligand bis[2,4-bis(trifluoromethyl)phenyl]phosphane oxide, (R(f))(2)P(O)H, reacts smoothly with solid platinum(II) dichloride yielding the trans-configured phosphinous acid platinum complex trans-[PtCl(2)({2,4-(CF(3))(2)C(6)H(3)}(2)POH)(2)]. The deprotonation of one phosphinous acid ligand with an appropriate base leads to the cis-configured monoanion complex cis-[PtCl(2)({2,4-(CF(3))(2)C(6)H(3)}(2)PO)(2)H](-), featuring the quasi-chelating phosphinous acid phosphinito unit, (R(f))(2)P-O-H···O=P(R(f))(2), which exhibits a strong hydrogen bridge substantiated by an O···O distance of 245.1(4) pm. The second deprotonation step is accompanied by a rearrangement to afford the trans-configured dianion trans-[PtCl(2)({2,4-(CF(3))(2)C(6)H(3)}(2)PO)(2)](2-). The reaction of (R(f))(2)P(O)H with solid palladium(II) dichloride initially yields a mononuclear palladium complex [PdCl(2)({2,4-(CF(3))(2)C(6)H(3)}(2)POH)(2)], which condenses under liberation of HCl to the neutral dinuclear palladium complex [Pd(2)(μ-Cl)(2){({2,4-(CF(3))(2)C(6)H(3)}(2)PO)(2)H}(2)]. The equilibrium between the mononuclear [PdCl(2)({2,4-(CF(3))(2)C(6)H(3)}(2)POH)(2)] and dinuclear [Pd(2)(μ-Cl)(2){({2,4-(CF(3))(2)C(6)H(3)}(2)PO)(2)H}(2)] palladium complexes is reversible and can be shifted in each direction by the addition of base or HCl, respectively. Treatment of palladium(II) hexafluoroacetylacetonate, [Pd(F(6)acac)(2)], with a slight excess of (R(f))(2)P

  15. Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives

    PubMed Central

    Kim, Do Hyun; Kim, Su Jeong; Ullah, Sultan; Yun, Hwi Young; Chun, Pusoon; Moon, Hyung Ryong

    2017-01-01

    The authors designed and synthesized 17 (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives to find a new chemical scaffold, showing excellent tyrosinase-inhibitory activity. Their tyrosinase-inhibitory activities were evaluated against mushroom tyrosinase at 50 μM, and five of the PDTM derivatives (PDTM3, PDTM7–PDTM9, and PDTM13) were found to inhibit mushroom tyrosinase more than kojic acid or arbutin, the positive controls. Of seventeen PDTMs, PDTM3 (half-maximal inhibitory concentration 13.94±1.76 μM), with a 2,4-dihydroxyphenyl moiety, exhibited greatest inhibitory effects (kojic acid half-maximal inhibitory concentration 18.86±2.14 μM). Interestingly, PDTM compounds with no hydroxyl group, PDTM7–PDTM9, also had stronger inhibitory activities than kojic acid. In silico studies of interactions between tyrosinase and the five PDTMs suggested their binding affinities were closely related to their tyrosinase-inhibitory activities. Cell-based experiments performed using B16F10 mouse-skin melanoma cells showed that PDTM3 effectively inhibited melanogenesis and cellular tyrosinase activity. A cell-viability study conducted using B16F10 cells indicated that the antimelanogenic effect of PDTM3 was not attributable to its cytotoxicity. Kinetic studies showed PDTM3 competitively inhibited tyrosinase, indicating binding to the tyrosinase-active site. We found that PDTM3 with a new chemical scaffold could be a promising candidate for skin-whitening agents, and that the 1,3-dithiolane ring could be used as a chemical scaffold for potent tyrosinase inhibition. PMID:28352157

  16. Negative polarity of phenyl-C{sub 61} butyric acid methyl ester adjacent to donor macromolecule domains

    SciTech Connect

    Alley, Olivia J.; Dawidczyk, Thomas J.; Hardigree, Josué F. Martínez; Katz, Howard E.; Wu, Meng-Yin; Johns, Gary L.; Markovic, Nina; Arnold, Michael S.

    2015-01-19

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (V{sub oc}) can also be dependent on the interfacial fields, in the event that they modulate the energy gap between donor HOMO and acceptor LUMO. A rise in the vacuum level of the acceptor will increase the gap and the V{sub oc}, which can be beneficial for device efficiency. Here, we measure the interfacial potential differences at donor-acceptor junctions using Scanning Kelvin Probe Microscopy, and quantify how much of the potential difference originates from physical contact between the donor and acceptor. We see a statistically significant and pervasive negative polarity on the phenyl-C{sub 61} butyric acid methyl ester (PCBM) side of PCBM/donor junctions, which should also be present at the complex interfaces in bulk heterojunctions. This potential difference may originate from molecular dipoles, interfacial interactions with donor materials, and/or equilibrium charge transfer due to the higher work function and electron affinity of PCBM. We show that the contact between PCBM and poly(3-hexylthiophene) doubles the interfacial potential difference, a statistically significant difference. Control experiments determined that this potential difference was not due to charges trapped in the underlying substrate. The direction of the observed potential difference would lead to increased V{sub oc}, but would also pose a barrier to electrons being injected into the PCBM and make recombination more favorable. Our method may allow unique information to be obtained in new donor-acceptor junctions.

  17. Apparent affinity of some 8-phenyl-substituted xanthines at adenosine receptors in guinea-pig aorta and atria.

    PubMed Central

    Collis, M. G.; Jacobson, K. A.; Tomkins, D. M.

    1987-01-01

    1 Some 8-phenyl-substituted, 1,3 dipropyl xanthines have previously been demonstrated to have a 20-400 fold greater affinity for A1 binding sites in rat CNS membranes than for A2 adenosine receptors in intact CNS cells from guinea-pigs. In the present study these compounds (1,3, dipropyl-8-phenylxanthine: DPPX; 1,3 dipropyl-8-(2 amino-4-chlorophenyl) xanthine: PACPX; 8-(4-(2-amino-ethyl)amino) carbonyl methyl oxyphenyl)-1,3-dipropylxanthine: XAC; and D-Lys-XAC) together with two that have not been reported to exhibit A1-receptor selectively (8-(p-sulphophenyl)theophylline: 8-PST; 8-(4-carboxy methyl oxyphenyl)-1,3-dipropylxanthine: XCC) have been evaluated as antagonists of the effects of 2-chloroadenosine in two isolated cardiovascular tissues. 2 The isolated tissues used were guinea-pig atria (bradycardic response) and aorta (relaxation), which are thought to possess A1 and A2 adenosine receptors, respectively. 3 All the xanthines antagonized responses evoked by 2-chloroadenosine in both tissues but did not affect responses evoked by acetylcholine (atria) or sodium nitrite (aorta). 4 The xanthines, 8-PST, XAC, D-Lys XAC, XCC and DPPX appeared to be competitive antagonists of the effects of 2-chloroadenosine, as Schild plot slopes did not differ significantly from unity. The 1,3-dipropyl substituted compounds had pA2 values from 6.5 to 7.4 and were more potent than the 1,3 dimethyl substituted 8-PST (pA2 4.9 to 5). 5 For individual xanthines, there was no difference between pA2 values obtained in the atria and in the aorta.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:3664093

  18. Photophysics and morphology of poly (3-dodecylthienylenevinylene)-[6,6]-phenyl-C{sub 61}-butyric acid methyl ester composite

    SciTech Connect

    Lafalce, E.; Toglia, P.; Jiang, X.; Zhang, C.

    2012-05-21

    A series of low band gap poly(3-dodecylthienylenevinylene) (PTV) with controlled morphological order have been synthesized and blended with the electron acceptor [6,6]-phenyl-C{sub 61}-butyric acid methyl ester (PCBM) for organic photovoltaic devices. Two polymers with the most and least side chain regioregularity were chosen in this work, namely the PTV010 and PTV55, respectively. Using photoluminescence, photo-induced absorption spectroscopy, and atomic force microscopy, we find no direct evidence of photoinduced charge transfer between the two constituents, independent of the bulk-heterojunction morphology of the film, although the possibility of formation of P{sup +}/C{sub 60}{sup -} charge transfer complex was not completely ruled out. The large exciton binding energy (E{sub b} = 0.6 eV) in PTV inhibits the photoinduced electron transfer from PTV to PCBM. In addition, excitons formed on polymer chains suffer ultrafast (

  19. Five new complexes based on 1-phenyl-1H-tetrazole-5-thiol: Synthesis, structural characterization and properties

    NASA Astrophysics Data System (ADS)

    Song, Jiang-Feng; Wang, Jun; Li, Si-Zhe; Li, Yang; Zhou, Rui-Sha

    2017-02-01

    Five new complexes based on 1-phenyl-1H-tetrazole-5-thiol (Hptt): 1,1‧-diphenyl-5,5‧- dithiodi-tetrazole (abbreviated as dptt) (1), {[Co2(OH)2(2,2‧-bipy)2(Hptt)2]·(ptt)2·(H2O)2}(2), [Cd2I2(2,2‧-bipy)2(ptt)2] (3), [Co(ptt)2]n (4) and [Cd(ptt)2]n (5), have been synthesized and fully characterized by elemental analyses, thermogravimetric analysis, powder X-ray diffraction, IR spectra and single-crystal X-ray diffraction. Structural analysis indicated that compound 1 is an organic matter generated from in situ oxidative coupling reaction of Hptt ligands under the help of Fe3+ ion. In compound 2, two Hptt ligands adopting μ2-κN, κS bridging mode and two μ2-OHbar bridge two Co(2,2‧-bipy) fragments into a[Co2(OH)2(2,2‧-bipy)2(Hptt)2]2+ core with short Co⋯Co distance (2.8185(10) Å). In compound 3, two Cd centers are joined into a dinuclear complex with short Cd⋯Cd distance (3.9282(14) Å) by two pttbar anions in μ2-κS, κS bridging mode. Compounds 4 and 5 are isostructural and both feature one-dimensional (1D) looped chain structures containing 8-membered [M2S2C2N2] rings (M = Co for 4, M = Cd for 5). Variable-temperature magnetic susceptibility measurement of compounds 2 and 4 reveal strong antiferromagnetic interactions between Co centers. The fluorescent properties of compounds 1, 3 and 5 are investigated in the solid state.

  20. Catalysis of the methoxyaminolysis of phenyl acetate by a preassociation mechanism with a solvent isotope effect maximum

    SciTech Connect

    Cox, M.M.; Jencks, W.P.

    1981-02-11

    General-acid catalysis of the reaction of methoxyamine with phenyl acetate by the proton, carboxylic acids, and ammonium ions follows a nonlinear Bronsted curve. This curve agrees with the expected enforced preassociation mechanism of catalysis. The stronger acids, including the proton, follow a Bronsted slope of ..cap alpha.. = 0.16 weaker acids react with partially rate-limiting proton transfer to the addition intermediate T/sup + -/, and the weakest acids follow a steeper Bronsted slope approaching ..cap alpha.. = 1.0. There is no decrease in the rate constant for catalysis by chloroacetic acid with increasing viscosity in water-glycerol mixtures; a decrease is observed for the reaction of methylamine with p-tolyl acetate catalyzed by acetate buffers, which is believed to proceed by a diffusion-controlled trapping mechanism. A sharp maximum in the solvent isotope effect at pK/sub HA/ = 6.8 confirms the kinetically significant proton-transfer step in the intermediate region near ..delta..pK = 0. The decrease with stronger acids represents a decrease in the isotope effect for this proton-transfer step, which is largely rate limiting for acids of pK/sub a/ = 4-7, but the decrease with weaker acids can be explained by the change to rate-limiting diffusional separation of T/sup +/ and A/sup -/. Two explanations are offered for the decreased isotope effect with increasing acid strength. (1) There is a sharp change to an asymmetric structure of the transition state for the very rapid proton-transfer step, as suggested by Melander and Westheimer. (2) There is a shift to a rate-limiting change in solvation that occurs immediately either before or after the proton-transfer step with stronger acids. It is possible to fit the observed Bronsted curve and isotope effect maximum with calculated rate constants that are based on a rate law and estimated rate constants for the steps of the latter mechanism.