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Sample records for 42-hydroxy phenyl quinoxaline

  1. 3-{2-[(3-Phenyl­quinoxalin-2-yl)­oxy]ethyl}-1,3-oxazolidin-2-one

    PubMed Central

    Daouda, Ballo; Brelot, Lydia; Doumbia, Mouhamadou Lamine; Essassi, El Mokhtar; Ng, Seik Weng

    2011-01-01

    The asymmetric unit of the title compound, C19H17N3O3, consists of two independent mol­ecules that are disposed about a pseudo-centre of inversion. The plane of the phenyl substituent is twisted by 38.1 (1)° [43.6 (1)° in the second mol­ecule] out of the plane of the quinoxaline ring system. The five-membered ring of the substituent at the 2-position adopts an envelope conformation; the 5-CH2 atom representing the flap lies out of the plane defined by the other four atoms [deviation 0.264 (7) Å in the first mol­ecule and 0.291 (6) Å in the second]. The dihedral angle between the five-membered ring and the 4-phenyl ring is 84.9 (1)° while that between the five-membered ring and the 5-phenyl ring is 65.6 (1)°. PMID:21754531

  2. (Phen­yl)(3-phenyl­sulfonyl-1,2-dihydro­pyrrolo­[1,2-a]quinoxalin-1-yl)methanone

    PubMed Central

    Dürüst, Yaşar; Sağırlı, Akın; Fronczek, Frank R.

    2011-01-01

    In the title mol­ecule, C24H18N2O3S, the 13-atom ring system comprising the quinoxaline and fused five-membered ring exhibits an r.m.s. deviation from coplanarity of 0.039 Å, with a maximum deviation of 0.0710 (10) Å for the PhCO-bearing C atom of the five-membered ring. The 10-membered C8N2 quinoxaline ring system has an r.m.s. deviation from coplanarity of 0.022 Å, with a maximum deviation of 0.0403 (9) Å for the C atom involved in the C=C bond in the five-membered ring. The three atoms of the five-membered ring fused to the quinoxaline ring system show deviations of up to 0.118 (2) Å for the PhCO-bearing C atom. C—N bond distances in the quinoxaline ring system of the title mol­ecule deviate from those in unsubstituted quinoxaline. In particular, the two C—N distances to the N atom involved in the five-membered ring are essentially equal, with values of 1.3786 (17) and 1.3773 (16) Å, unlike the difference of nearly 0.06 Å in quinoxaline. PMID:22219900

  3. Two Dimensional Aggregation Behaviors of Quinoxaline Dendrimers.

    PubMed

    Choi, Soyoung; Lee, Hoik; Kim, Hwan Kyu; Lee, Sang Uck; Sohn, Daewon

    2015-02-01

    This study focuses on the molecular behavior of two dendrimers containing a hydrophilic core group (carboxyl group) and hydrophobic branches (quinoxaline and methoxyphenyl groups), 2,3-bis(4-(2,3- bis(4-methoxyphenyl)quinoxalin-6-yloxy)phenyl)quinoxaline-6-carb-oxylic acid (G2) and 2,3-bis(4-(2,3-bis(4-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yloxy)phe-nyl)quinoxalin-6-y-oxy)phenyl) quin oxaline-6-carboxylic acid (G3) at the air-water interface. To understand the mechanism of the self-assembly of these molecules, we measured the surface pressure-area (III-A) isotherm and investigated the surface morphology of Langmuir-Blodgett films transferred onto hydrophilic silicon wafers using atomic force microscopy (AFM). Upon compression, G2 molecules stand up and steadily make close-packed monolayer whereas G3 molecules form circular domains and gradually make aggregates of domains. These results were confirmed by the X-ray Reflectivity (XRR) profiles of G2 and G3 monolayers transferred onto silicon substrates. PMID:26353682

  4. Visible-light-induced, copper(I)-catalysed C-N coupling between o-phenylenediamine and terminal alkynes: one-pot synthesis of 3-phenyl-2-hydroxy-quinoxalines.

    PubMed

    Sagadevan, Arunachalam; Ragupathi, Ayyakkannu; Hwang, Kuo Chu

    2013-12-01

    Visible-light-initiated aerobic direct C-N coupling between o-phenylenediamines and terminal acetylenes was performed using simple copper(I) chloride as a catalyst for the synthesis of quinoxaline derivatives. The current method works well for a wide range of electron rich as well as electron poor group-substituted o-phenylenediamines and phenylacetylenes. The key component in the reaction is the direct photo-excitation of in situ generated copper arylacetylide (λ(abs) = 420-480 nm). Moreover, as compared to the literature reports (thermal process), the current photochemical method is simple, mild, high yielding, and more viable towards the construction of biologically important quinoxaline derivatives from easily accessible raw materials, without the need of ligands and strong oxidants. PMID:24057350

  5. Quinoxalines Potential to Target Pathologies.

    PubMed

    Tristán-Manzano, María; Guirado, Antonio; Martínez-Esparza, María; Gálvez, Jesús; García-Peñarrubia, Pilar; Ruiz-Alcaraz, Antonio J

    2015-01-01

    The study of quinoxalines has increased immeasurably during the last two decades, due firstly to their relatively simple chemical synthesis, which has generated a vast variety of compounds with diverse structural modifications, and secondly, to the wide therapeutic potential and biological activities exhibited by this family of compounds. Quinoxalines constitute a rising biomedical class of low-molecular weight heterocyclic compounds with potential functions as antitumour, anti-inflammatory, antibacterial, antiviral, antifungal, antiparasitic and antidiabetic agents, as well as being of interest for the potential treatment of glaucoma, insomnia, cardiovascular and neurological diseases, among others. However, a deeper knowledge of the molecular targets of quinoxalines that fulfil a key role in certain pathologies is required for the development of new and more specific drugs through a rational design strategy to avoid undesirable side effects. In the present review, we summarize the most important molecular targets of the quinoxaline derivatives discovered to date, thus providing a first reference index for researchers to identify the potential targets of their quinoxalines derived collections, which could facilitate the development of new quinoxaline- based therapies. PMID:26264925

  6. First Evidence of Palytoxin and 42-Hydroxy-palytoxin in the Marine Cyanobacterium Trichodesmium

    PubMed Central

    Kerbrat, Anne Sophie; Amzil, Zouher; Pawlowiez, Ralph; Golubic, Stjepko; Sibat, Manoella; Darius, Helene Taiana; Chinain, Mireille; Laurent, Dominique

    2011-01-01

    Marine pelagic diazotrophic cyanobacteria of the genus Trichodesmium (Oscillatoriales) are widespread throughout the tropics and subtropics, and are particularly common in the waters of New Caledonia. Blooms of Trichodesmium are suspected to be a potential source of toxins in the ciguatera food chain and were previously reported to contain several types of paralyzing toxins. The toxicity of water-soluble extracts of Trichodesmium spp. were analyzed by mouse bioassay and Neuroblastoma assay and their toxic compounds characterized using liquid chromatography coupled with tandem mass spectrometry techniques. Here, we report the first identification of palytoxin and one of its derivatives, 42-hydroxy-palytoxin, in field samples of Trichodesmium collected in the New Caledonian lagoon. The possible role played by Trichodesmium blooms in the development of clupeotoxism, this human intoxication following the ingestion of plankton-eating fish and classically associated with Ostreopsis blooms, is also discussed. PMID:21731549

  7. Acute oral toxicity in mice of a new palytoxin analog: 42-hydroxy-palytoxin.

    PubMed

    Tubaro, A; Del Favero, G; Beltramo, D; Ardizzone, M; Forino, M; De Bortoli, M; Pelin, M; Poli, M; Bignami, G; Ciminiello, P; Sosa, S

    2011-04-01

    The acute oral toxicity of a new palytoxin congener, 42-hydroxy-palytoxin (42-OH-PLTX), was investigated in female CD-1 mice. The toxin (300-1697 μg/kg), administered by gavage, induced scratching, jumping, respiratory distress, cyanosis, paralysis and death of mice, with an LD₅₀ of 651 μg/kg (95% confidence limits: 384-1018 μg/kg) within 24 h. Hematoclinical analyses showed increased plasma levels of lactate dehydrogenase and aspartate-aminotransferase at doses of 600 μg/kg and above, as well as of alanine-aminotransferase, creatine phosphokinase and potassium ions at ≥ 848 μg/kg. Histology revealed inflammatory lesions in the non-glandular area of the stomach of mice that survived up to 24 h after gavage (424-1200 μg/kg). Although no histological alterations were seen in skeletal and cardiac muscles, changes in some plasma biomarkers (creatine phosphokinase, lactate dehydrogenase) suggested involvement of these tissues in 42-OH-PLTX oral toxicity, in agreement with epidemiological data on seafood poisonings ascribed to palytoxins. Complete recovery of the tissue and hematological changes was observed two weeks post-exposure. Furthermore, 42-OH-PLTX induced in vitro delayed erythrocyte hemolysis at concentrations similar to those of PLTX (EC₅₀ = 7.6 and 13.2 x 10⁻¹² M, respectively). This hemolysis could be completely neutralized by a monoclonal anti-PLTX antibody. The in vivo data, together with the in vitro data recorded for 42-OH-PLTX, seem to indicate Na+/K+-ATPase as one of the key cellular targets of this toxin. PMID:21333670

  8. 1-Benzyl-3-methyl­quinoxalin-2(1H)-one

    PubMed Central

    Ramli, Youssef; Moussaif, Ahmed; Zouihri, Hafid; Lazar, Saïd; Essassi, E. M.

    2010-01-01

    The asymmetric unit of the title compound, C16H14N2O, contains three independent mol­ecules. The dihedral angles between the quinoxaline and phenyl planes in the three mol­ecules are 82.58 (8), 85.66 (9) and 85.36 (9)°. The crystal packing is stabilized by C—H⋯O and C—H⋯N hydrogen bonds. PMID:21588252

  9. Unexpected imidazoquinoxalinone annulation products in the photoinitiated reaction of substituted-3-methyl-quinoxalin-2-ones with N-phenylglycine.

    PubMed

    De la Fuente, Julio R; Cañete, Álvaro; Jullian, Carolina; Saitz, Claudio; Aliaga, Christian

    2013-01-01

    Photoinduced electron transfer between N-phenylglycine (NPG) and electronically excited triplets of 7-substituted-3-methyl-quinoxalin-2-ones in acetonitrile generate the respective ion radical pair, where by decarboxylation the phenyl-amino-alkyl radical, PhNHCH2•, is generated. This radical reacts with the 3-methyl-quinoxalin-2-ones ground states, leading to the product 2. Other, unexpected, 7-substituted-1,2,3,3a-tetrahydro-3a-methyl-2-phenylimidazo[1,5-a]quinoxalin-4(5H)-ones, annulation products, 3a-f, were generated; likely by the addition of two PhNHCH2• radicals, to positions 3 and 4 of the quinoxalin-2-ones. The reaction mechanism includes a photoinduced one electron transfer initiation step, propagation steps involving radical intermediates and NPG with radical chain termination steps that lead to the respective products 2a-f and 3a-f and NPG by-products. The proposed mechanism accounts for the strong dependency found for the initial photoconsumption quantum yields on the electron-withdrawing power of the substituent. Therefore, photolysis of common reactants widely used such as NPG and substituted quinoxalin-2-ones may provide a simple synthetic way to the unusual, unreported tetrahydro-imidazoquinoxalinones 3a-f. PMID:24033113

  10. Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives.

    PubMed

    Ghorab, Mostafa M; Ragab, Fatma A; Heiba, Helmy I; El-Gazzar, Marwa G; El-Gazzar, Mostafa G

    2011-12-01

    Sulfonamides and quinoxaline derivatives possess many types of biological activities and have been recently reported to show substantial antitumor activity. This paper reports the synthesis of novel thioureido sulfaquinoxaline derivatives. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against a human liver cell line (HEPG2) and showed higher activity than the reference drug doxorubicin. 4-(3-(4-Ethylbenzoate) thioureido)-N-(quinoxalin-2-yl)benzenesulfonamide (9) (IC₅₀ = 15.6 μmol L⁻¹), N-(pyridin-2-yl)-4-(3-(4-(N-quinoxalin-2-yl-sulfamoyl)phenyl)thioureido)benzenesulfonamide (10) (IC₅₀ = 26.8 μmol L⁻¹) and N-(quinoxalin-2-yl)-4-(3-(4-(N-thiazol-2-ylsulfamoyl)phenyl)thioureido)benzenesulfonamide (11) (IC₅₀ = 24.4 μmol L⁻¹) were the most potent compared to doxorubicin (IC₅₀ = 71.8 μmol L⁻¹). The most potent compounds 9, 10 and 11 were evaluated as radiosensitizing agents by subjecting the compounds to γ-irradiation (8 kGy). PMID:22202200

  11. Synthesis and Structure–Activity Relationship Studies of 4-((2-Hydroxy-3-methoxybenzyl)amino)benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase

    PubMed Central

    Luci, Diane K.; Jameson, J. Brian; Yasgar, Adam; Diaz, Giovanni; Joshi, Netra; Kantz, Auric; Markham, Kate; Perry, Steve; Kuhn, Norine; Yeung, Jennifer; Kerns, Edward H.; Schultz, Lena; Holinstat, Michael; Nadler, Jerry L.; Taylor-Fishwick, David A.; Jadhav, Ajit; Simeonov, Anton; Holman, Theodore R.; Maloney, David J.

    2014-01-01

    Human lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic responses such as platelet aggregation, inflammation, and cell proliferation. Our group has taken a particular interest in platelet-type 12-(S)-LOX (12-LOX) because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide-based scaffold. Top compounds, exemplified by 35 and 36, display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable ADME properties. In addition, both compounds inhibit PAR-4 induced aggregation and calcium mobilization in human platelets and reduce 12-HETE in β-cells. PMID:24393039

  12. Chemistry and toxicology of quinoxaline, organotin, organofluorine, and formamidine acaricides.

    PubMed Central

    Knowles, C O

    1976-01-01

    Quinoxaline, organotin, organofluorine, and formamidine compounds are among the newer pesticide chemicals used for acarine control. Included in these four classes are some of the most selective synthetic organic toxicants currently in the acaricide/insecticide arsenal. Oxythioquinox, Plictran (tricyclohexylhydroxytin), Nissol [2-fluoro-N-methyl-N-(1-naphthyl)acetamide], and chlordimeform are examples of quinoxaline, organotin, organofluorine, and formamidine acaricides, respectively. The chemistry and toxicology of these and related compounds are discussed. PMID:789072

  13. BF3-promoted electrochemical properties of quinoxaline in propylene carbonate

    DOE PAGESBeta

    Carino, Emily V.; Diesendruck, Charles E.; Moore, Jeffrey S.; Curtiss, Larry A.; Assary, Rajeev S.; Brushett, Fikile R.

    2015-02-04

    Electrochemical and density functional studies demonstrate that coordination of electrolyte constituents to quinoxalines modulates their electrochemical properties. Quinoxalines are shown to be electrochemically inactive in most electrolytes in propylene carbonate, yet the predicted reduction potential is shown to match computational estimates in acetonitrile. We find that in the presence of LiBF4 and trace water, an adduct is formed between quinoxaline and the Lewis acid BF3, which then displays electrochemical activity at 1–1.5 V higher than prior observations of quinoxaline electrochemistry in non-aqueous media. Direct synthesis and testing of a bis-BF3 quinoxaline complex further validates the assignment of the electrochemically activemore » species, presenting up to a ~26-fold improvement in charging capacity, demonstrating the advantages of this adduct over unmodified quinoxaline in LiBF4-based electrolyte. The use of Lewis acids to effectively “turn on” the electrochemical activity of organic molecules may lead to the development of new active material classes for energy storage applications.« less

  14. Evaluation of the mutagenicity of simple substituted quinoxalines in Salmonella typhimurium.

    PubMed

    Conti, Luigi; Crebelli, Riccardo

    2016-01-01

    Limited information is available on the genotoxicity of simple quinoxalines, distinct from the food related carcinogenic derivatives bearing an aromatic amino group. Isolated positive results, with no apparent structure-activity relationships, were reported in earlier studies on alkyl substituted quinoxalines, raising a safety concern in some regulatory authorities in view of the potential human exposure related to their use as food flavors. In order to elucidate the genotoxic hazard posed by simple quinoxalines, in this work a random set of mono- and bi-substituted methyl, chloro- and hydroxyl- quinoxalines have been tested in an OECD-compliant bacterial reversion test (TG 471). The results obtained do not highlight any genotoxic potential in the set of quinoxalines examined, and suggest that this may be a common trait for other simple substituted quinoxalines. Earlier published positive findings were not confirmed in this work, which call for a cautious approach in the use of literature data for regulatory purpose. PMID:26365056

  15. Quinoxaline polymers and copolymers derived from 1, 4-BIS(1'-napthalenyloxayl) benzene

    NASA Technical Reports Server (NTRS)

    Port, W. S.; Loszewski, R. C.

    1974-01-01

    A route for the synthesis of a new monomer, 1,4-bis(1'-naphthalenyl)-oxayl benzene, was devised, and six polymers and copolymers were prepared from this monomer, 1,4-bis(phenyloaxaly)benzene, 3,3'-diaminobenzidine and 3,3',4,4'-tetraaminobenzophenone. Thermogravimetric analysis showed that decomposition of these quinoxaline polymers and copolymers sets in at about 500 C but does not become significant in an inert atmosphere below 600 C. Oxidation becomes significant at about 550 C and the phenylquinoxaline homopolymer is somewhat more oxidation resistant than is the 1-naphthalenylquinoxaline homopolymer. Stress-relaxation measurements showed that, with two exceptions, the homopolymers and copolymers exhibited two second-order transition temperatures, one at about 204.4 C (400 F) and the other at about 315.6 C (600 F). No gross differences in the high temperature plasticity was observed between the naphthalenyl- and the phenyl-quinoaxaline homopolymers. Work was begun on a method for cross-linking polyquinoxalines. A new monomer, p-(methyloxaly)benzil, was synthesized, and model reaction studies showed that cross-linking of 2-methylquinoxaline polymers by a Michael condensation with dimaleimides will probably occur.

  16. Synthesis of quinoxaline azido and amino reverse ribofuranoside and their O-regioisomers.

    PubMed

    Ali, Ibrahim A I

    2014-01-01

    A series of quinoxaline azido reverse nucleosides 3a-c and their O-regioisomers 4a-c was prepared by reaction of quinoxaline 1a-c with 3-azido-3-deoxy-1,2-O-isopropylidene-5-p-toluenesulfonyl-D-ribofuranose (2) in the presence of sodium hydride. Structure modification of these interesting structures includes reduction and the subsequent acetylation reactions to give quinoxaline amino and acetyl amino reverse nucleosides and their O-regioisomers. PMID:24689845

  17. New Conjugates of Quinoxaline as Potent Antitubercular and Antibacterial Agents

    PubMed Central

    Kuppusamy, Rajendran; Killi, Sunil Kumar; Reddy, Y. Padmanabha

    2016-01-01

    Considering quinoxaline as a privileged structure for the design of potent intercalating agents, some new sugar conjugates of quinoxaline were synthesized and characterized by IR, 1HNMR, 13C NMR, and mass spectral data. In vitro testing for antitubercular and antimicrobial activities was performed against Mycobacterium tuberculosis H37Rv and some pathogenic bacteria. Results revealed that conjugate containing ribose moiety demonstrated the most promising activity against Mycobacteria and bacteria with minimum inhibitory concentrations (MIC) of 0.65 and 2.07 μM, respectively. Other conjugates from xylose, glucose, and mannose were moderately active whilst disaccharides conjugates were found to be less active. In silico docking analysis of prototype compound revealed that ATP site of DNA gyrase B subunit could be a possible site for inhibitory action of these synthesized compounds. PMID:27051530

  18. 2,3-Dimethyl-6-nitro­quinoxaline

    PubMed Central

    Ghalib, Raza Murad; Hashim, Rokiah; Mehdi, Sayed Hasan; Goh, Jia Hao; Fun, Hoong-Kun

    2010-01-01

    The asymmetric unit of the title quinoxaline compound, C10H9N3O2, contains two crystallographically independent mol­ecules (A and B). The quinoxaline ring systems are essentially planar, with maximum deviations of 0.006 (1) and 0.017 (1) Å, respectively, for mol­ecules A and B. In mol­ecule A, the dihedral angle formed between the quinoxaline ring system and nitro group is 10.94 (3)° [6.31 (13)° for mol­ecule B]. In the crystal, mol­ecules are linked into chains propagating along [001]: one forms zigzag chains linked by C—H⋯O hydrogen bonds, whilst the other forms ladder-like chains by way of C—H⋯N and C—H⋯O hydrogen bonds. The packing is further consolidated by weak π–π inter­actions [range of centroid–centroid distances = 3.5895 (7)–3.6324 (7) Å]. PMID:21588035

  19. Asymmetric hydrogenation of 2- and 2,3-substituted quinoxalines with chiral cationic ruthenium diamine catalysts.

    PubMed

    Qin, Jie; Chen, Fei; Ding, Ziyuan; He, Yan-Mei; Xu, Lijin; Fan, Qing-Hua

    2011-12-16

    The enantioselective hydrogenation of 2-alkyl- and 2-aryl-subsituted quinoxalines and 2,3-disubstituted quinoxalines was developed by using the cationic Ru(η(6)-cymene)(monosulfonylated diamine)(BArF) system in high yields with up to 99% ee. The counteranion was found to be critically important for the high enantioselectivity and/or diastereoselectivity. PMID:22098608

  20. Radical Chemistry and Cytotoxicity of Bioreductive 3-Substituted Quinoxaline Di-N-Oxides.

    PubMed

    Anderson, Robert F; Yadav, Pooja; Shinde, Sujata S; Hong, Cho R; Pullen, Susan M; Reynisson, Jóhannes; Wilson, William R; Hay, Michael P

    2016-08-15

    The radical chemistry and cytotoxicity of a series of quinoxaline di-N-oxide (QDO) compounds has been investigated to explore the mechanism of action of this class of bioreductive drugs. A series of water-soluble 3-trifluoromethyl (4-10), 3-phenyl (11-19), and 3-methyl (20-21) substituted QDO compounds were designed to span a range of electron affinities consistent with bioreduction. The stoichiometry of loss of QDOs by steady-state radiolysis of anaerobic aqueous formate buffer indicated that one-electron reduction of QDOs generates radicals able to initiate chain reactions by oxidation of formate. The 3-trifluoromethyl analogues exhibited long chain reactions consistent with the release of the HO(•), as identified in EPR spin trapping experiments. Several carbon-centered radical intermediates, produced by anaerobic incubation of the QDO compounds with N-terminal truncated cytochrome P450 reductase (POR), were characterized using N-tert-butyl-α-phenylnitrone (PBN) and 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide (DEPMPO) spin traps and were observed by EPR. Experimental data were well simulated for the production of strongly oxidizing radicals, capable of H atom abstraction from methyl groups. The kinetics of formation and decay of the radicals produced following one-electron reduction of the parent compounds, both in oxic and anoxic solutions, were determined using pulse radiolysis. Back oxidation of the initially formed radical anions by molecular oxygen did not compete effectively with the breakdown of the radical anions to form oxidizing radicals. The QDO compounds displayed low hypoxic selectivity when tested against oxic and hypoxic cancer cell lines in vitro. The results from this study form a kinetic description and explanation of the low hypoxia-selective cytotoxicity of QDOs against cancer cells compared to the related benzotriazine 1,4-dioxide (BTO) class of compounds. PMID:27380897

  1. 3-Methyl-1-(prop-2-en-1-yl)quinoxalin-2(1H)-one

    PubMed Central

    Ramli, Youssef; Slimani, Rachid; Zouihri, Hafid; Lazar, Saïd; Essassi, E. M.

    2010-01-01

    In the mol­ecule of the title compound, C12H12N2O, the quinoxaline ring is planar with an r.m.s. deviation of 0.007 (15) Å. The dihedral angle between the quinoxaline and propenyl planes is 82.1 (2)°. The crystal packing is stabilized by offset π–π stacking between the quinoxaline rings [centroid–centroid distance = 3.8832 (9) Å]. PMID:21587981

  2. Phenanthro[4,5-fgh]quinoxaline-Fused Subphthalocyanines: Synthesis, Structure, and Spectroscopic Characterization.

    PubMed

    Pan, Houhe; Liu, Wenbo; Wang, Chiming; Wang, Kang; Jiang, Jianzhuang

    2016-07-01

    A series of four phenanthro[4,5-fgh]quinoxaline-fused subphthalocyanine derivatives 0-3 containing zero, one, two, and three phenanthro[4,5-fgh]quinoxaline moieties, respectively, were isolated from the mixed cyclotrimerization reaction of 2,9-di-tert-butylphenanthro[4,5-fgh]quinoxaline-5,6-dicarbonitrile with 4,5-bis(2,6-diisopropylphenoxy)phthalonitrile and characterized by a series of spectroscopic methods including MALDI-TOF mass, (1) H NMR, electronic absorption, magnetic circular dichroism (MCD), and fluorescence spectroscopy. The molecular structures for the compounds 0 and 2 were clearly revealed on the basis of single-crystal X-ray diffraction analysis. Their electrochemical properties were also studied by cyclic voltammetry. In particular, theoretical calculations in combination with the electronic absorption and electrochemical analyses revealed the significant influence of the fused-phenanthro[4,5-fgh]quinoxaline units on the electronic structures. PMID:27123546

  3. Photochemical reactions of biologically important quinoxaline n-oxides

    SciTech Connect

    Dvoryantseva, G.G.; Tetenchuk, K.P.; Pol'shakov, V.I.; Elina, A.S.

    1987-02-01

    The authors study the photochemical reactions of quinoxidine, dioxidine, and a number of related derivatives of quinoxaline 1,4-di-N-oxides containing methyl, halomethyl, and carboxamide groups in the pyrazine ring. Thin-layer chromatography, UV spectrophotometry, and NMR/sup 1/H and /sup 13/C spectroscopy were used as the main methods for monitoring the photolysis process and establishing the structure of the products formed. The investigation established that two types of photochemical reactions are observed in the series of compounds discussed: photoisomerization with migration of a substitutent to the nitrogen atom of the heterocycle, and photorearrangement with elimination of a substituent and the formation of the corresponding lactams.

  4. One-Pot Regiospecific Synthesis of Quinoxalines via a CH2-Extrusion Reaction.

    PubMed

    Shen, Jinhai; Wang, Xiangdong; Lin, Xing; Yang, Zhenhui; Cheng, Guolin; Cui, Xiuling

    2016-03-18

    A convenient "one-pot" regiospecific synthesis of substituted quinoxalines from o-phenylenediamines and ynones under metal-free conditions has been developed. An intermolecular Michael addition reaction, a dehydration condensation, and a base-promoted C-α-CH2-extrusion were involved in this procedure, which features high regioselectivity, efficiency, and environmental friendliness. Various quinoxalines were provided in up to 95% yield for 33 examples. PMID:26925522

  5. Synthesis, ligand-receptor modeling studies and pharmacological evaluation of novel 4-modified-2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives as potent and selective human A3 adenosine receptor antagonists.

    PubMed

    Colotta, Vittoria; Catarzi, Daniela; Varano, Flavia; Lenzi, Ombretta; Filacchioni, Guido; Martini, Claudia; Trincavelli, Letizia; Ciampi, Osele; Traini, Chiara; Pugliese, Anna Maria; Pedata, Felicita; Morizzo, Erika; Moro, Stefano

    2008-06-01

    The study of some 4-substituted-2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives, designed as hA(3) adenosine receptor antagonists, is reported. The new compounds bear on the four-position different acylamino, sulfonylamino, benzylureido and benzyloxy moieties, which have also been combined with a para-methoxy group on the 2-phenyl ring or with a nitro residue at the six-position. Many derivatives show high hA(3) adenosine receptor affinities and selectivities both versus hA(1) and hA(2A) receptors. The observed structure-affinity relationships of this class of antagonists have been exhaustively rationalized using the recently published ligand-based homology modeling (LBHM) approach. The selected 4-bismethanesulfonylamino-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (13), which shows high hA(3) affinity (K(i)=5.5nM) and selectivity versus hA(1), hA(2A) (both selectivity ratios>1800) and hA(2B) (cAMP assay, IC(50)>10,000nM) receptors, was tested in an in vitro rat model of cerebral ischemia, proving to be effective in preventing the failure of synaptic activity, induced by oxygen and glucose deprivation in the hippocampus, and in delaying the occurrence of anoxic depolarization. PMID:18468446

  6. BF3-promoted electrochemical properties of quinoxaline in propylene carbonate

    SciTech Connect

    Carino, Emily V.; Diesendruck, Charles E.; Moore, Jeffrey S.; Curtiss, Larry A.; Assary, Rajeev S.; Brushett, Fikile R.

    2015-02-04

    Electrochemical and density functional studies demonstrate that coordination of electrolyte constituents to quinoxalines modulates their electrochemical properties. Quinoxalines are shown to be electrochemically inactive in most electrolytes in propylene carbonate, yet the predicted reduction potential is shown to match computational estimates in acetonitrile. We find that in the presence of LiBF4 and trace water, an adduct is formed between quinoxaline and the Lewis acid BF3, which then displays electrochemical activity at 1–1.5 V higher than prior observations of quinoxaline electrochemistry in non-aqueous media. Direct synthesis and testing of a bis-BF3 quinoxaline complex further validates the assignment of the electrochemically active species, presenting up to a ~26-fold improvement in charging capacity, demonstrating the advantages of this adduct over unmodified quinoxaline in LiBF4-based electrolyte. The use of Lewis acids to effectively “turn on” the electrochemical activity of organic molecules may lead to the development of new active material classes for energy storage applications.

  7. Photo-degradation in air of the active layer components in a thiophene-quinoxaline copolymer:fullerene solar cell.

    PubMed

    Hansson, Rickard; Lindqvist, Camilla; Ericsson, Leif K E; Opitz, Andreas; Wang, Ergang; Moons, Ellen

    2016-04-28

    We have studied the photo-degradation in air of a blend of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) and poly[2,3-bis-(3-octyloxyphenyl)quinoxaline-5,8-diyl-alt-thiophene-2,5-diyl] (TQ1), and how the photo-degradation affects the solar cell performance. Using near-edge X-ray absorption fine structure (NEXAFS) spectroscopy, changes to the electronic structure of TQ1 and PCBM caused by illumination in ambient air are investigated and compared between the pristine materials and the blend. The NEXAFS spectra show that the unoccupied molecular orbitals of TQ1 are not significantly changed by the exposure of pristine TQ1 to light in air, whereas those of PCBM are severely affected as a result of photo-induced degradation of PCBM. Furthermore, the photo-degradation of PCBM is accelerated by blending it with TQ1. While the NEXAFS spectrum of TQ1 remains unchanged upon illumination in air, its valence band spectrum shows that the occupied molecular orbitals are weakly affected. Yet, UV-Vis absorption spectra demonstrate photo-bleaching of TQ1, which is attenuated in the presence of PCBM in blend films. Illumination of the active layer of TQ1:PCBM solar cells prior to cathode deposition causes severe losses in electrical performance. PMID:27051887

  8. Vertical and lateral morphology effects on solar cell performance for a thiophene–quinoxaline copolymer:PC 70BM blend

    DOE PAGESBeta

    Hansson, Rickard; Ericsson, Leif K. E.; Holmes, Natalie P.; Rysz, Jakub; Opitz, Andreas; Campoy-Quiles, Mariano; Wang, Ergang; Barr, Matthew G.; Kilcoyne, A. L. David; Zhou, Xiaojing; et al

    2015-02-13

    The distribution of electron donor and acceptor in the active layer is known to strongly influence the electrical performance of polymer solar cells for most of the high performance polymer:fullerene systems. The formulation of the solution from which the active layer is spincoated plays an important role in the quest for morphology control. We have studied how the choice of solvent and the use of small amounts of a low vapour pressure additive in the coating solution influence the film morphology and the solar cell performance for blends of poly[2,3-bis-(3-octyloxyphenyl)quinoxaline-5,8-diyl-alt-thiophene-2,5-diyl] (TQ1) and [6,6]-phenyl C71-butyric acid methyl ester (PC70BM). We havemore » investigated the lateral morphology using atomic force microscopy (AFM) and scanning transmission X-ray microscopy (STXM), the vertical morphology using dynamic secondary ion mass spectrometry (d-SIMS) and variable-angle spectroscopic ellipsometry (VASE), and the surface composition using near-edge X-ray absorption fine structure (NEXAFS). The lateral phase-separated domains observed in films spincoated from single solvents, increase in size with increasing solvent vapour pressure and decreasing PC70BM solubility, but are not observed when 1-chloronaphthalene (CN) is added. A strongly TQ1-enriched surface layer is formed in all TQ1:PC70BM blend films and rationalized by surface energy differences. The photocurrent and power conversion efficiency strongly increased upon the addition of CN, while the leakage current decreased by one to two orders of magnitude. The higher photocurrent correlates with the finer lateral structure and stronger TQ1-enrichment at the interface with the electron-collecting electrode. This indicates that the charge transport and collection are not hindered by this polymer-enriched surface layer. Neither the open-circuit voltage nor the series resistance of the devices are sensitive to the differences in morphology.« less

  9. Iodinated (Perfluoro)alkyl Quinoxalines by Atom Transfer Radical Addition Using ortho-Diisocyanoarenes as Radical Acceptors.

    PubMed

    Leifert, Dirk; Studer, Armido

    2016-09-12

    A simple method for the preparation of functionalized quinoxalines is reported. Starting from readily accessible ortho-diisocyanoarenes and (perfluoro)alkyl iodides, the quinoxaline core is constructed during (perfluoro)alkylation by atom transfer radical addition (ATRA), resulting in 2-iodo-3-(perfluoro)alkylquinoxalines. The radical cascades are readily initiated either with visible light or by using α,α'-azobisisobutyronitrile (AIBN). The heteroarene products are obtained in high yields (up to 94 %), and the method can be readily scaled up. Useful follow-up chemistry documents the value of the novel radical quinoxaline synthesis. PMID:27510610

  10. 4-amido-2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-ones as new potent and selective human A3 adenosine receptor antagonists. synthesis, pharmacological evaluation, and ligand-receptor modeling studies.

    PubMed

    Lenzi, Ombretta; Colotta, Vittoria; Catarzi, Daniela; Varano, Flavia; Filacchioni, Guido; Martini, Claudia; Trincavelli, Letizia; Ciampi, Osele; Varani, Katia; Marighetti, Federico; Morizzo, Erika; Moro, Stefano

    2006-06-29

    A structural investigation on some 4-amido-2-phenyl-1,2-dihydro-1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives, designed as human A3 adenosine receptor (hA3 AR) antagonists, is described. In the new derivatives, some acyl residues with different steric bulk were introduced on the 4-amino group, and their combination with the 4-methoxy group on the 2-phenyl moiety, and/or the 6-nitro/6-amino substituent on the fused benzo ring, was also evaluated. Most of the new derivatives were potent and selective hA3 AR antagonists. SAR analysis showed that hindering and lipophilic acyl moieties not only are well tolerated but even ameliorate the hA3 affinity. Interestingly, the 4-methoxy substituent on the appended 2-phenyl moiety, as well as the 6-amino group, always exerted a positive effect, shifting the affinity toward the hA3 receptor subtype. In contrast, the 6-nitro substituent exerted a variable effect. An intensive molecular modeling investigation was performed to rationalize the experimental SAR findings. PMID:16789747

  11. Design, synthesis and anti-HIV activity of novel quinoxaline derivatives.

    PubMed

    Patel, Saloni B; Patel, Bhumika D; Pannecouque, Christophe; Bhatt, Hardik G

    2016-07-19

    In order to design novel anti-HIV agents, pharmacophore modelling, virtual screening, 3D-QSAR and molecular docking studies were performed. Pharmacophore model was generated using 17 structurally diverse molecules using DISCOtech followed by refinement with GASP module of Sybyl X. The best model containing four features; two donor sites, one acceptor atom and one hydrophobic region; was used as a query for virtual screening in NCI database and 6 compounds with Qfit value ≥98 were retrieved. The quinoxaline ring which is the bio-isostere of pteridine ring, retrieved as a hit in virtual screening, was selected as a core moiety. 3D-QSAR was carried on thirty five 5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide derivatives. Contour map analysis of best CoMFA and CoMSIA model suggested incorporation of hydrophobic, bulky and electronegative groups to increase potency of the designed compounds. 50 quinoxaline derivatives with different substitutions were designed on basis of both ligand based drug design approaches and were mapped on the best pharmacophore model. From this, best 32 quinoxaline derivatives were docked onto the active site of integrase enzyme and in-silico ADMET properties were also predicted. From this data, synthesis of top 7 quinoxaline derivatives was carried out and were characterized using Mass, (1)H-NMR and (13)C-NMR spectroscopy. Purity of compounds were checked using HPLC. These derivatives were evaluated for anti-HIV activity on III-B strain of HIV-1 and cytotoxicity studies were performed on VERO cell line. Two quinoxaline derivatives (7d and 7e) showed good results, which can be further explored to develop novel anti-HIV agents. PMID:27105027

  12. Relationship between electronic properties and drug activity of seven quinoxaline compounds: A DFT study

    NASA Astrophysics Data System (ADS)

    Behzadi, Hadi; Roonasi, Payman; Assle taghipour, Khatoon; van der Spoel, David; Manzetti, Sergio

    2015-07-01

    The quantum chemical calculations at the DFT/B3LYP level of theory were carried out on seven quinoxaline compounds, which have been synthesized as anti-Mycobacterium tuberculosis agents. Three conformers were optimized for each compound and the lowest energy structure was found and used in further calculations. The electronic properties including EHOMO, ELUMO and related parameters as well as electron density around oxygen and nitrogen atoms were calculated for each compound. The relationship between the calculated electronic parameters and biological activity of the studied compounds were investigated. Six similar quinoxaline derivatives with possible more drug activity were suggested based on the calculated electronic descriptors. A mechanism was proposed and discussed based on the calculated electronic parameters and bond dissociation energies.

  13. New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones

    PubMed Central

    Georgescu, Emilian; Nicolescu, Alina; Georgescu, Florentina; Teodorescu, Florina; Marinescu, Daniela; Macsim, Ana-Maria

    2014-01-01

    Summary The one-pot three-component reactions of 1-substituted benzimidazoles with ethyl bromoacetate and electron-deficient alkynes, in 1,2-epoxybutane, gave a variety of pyrrolo[1,2-a]quinoxalin-4-ones and pyrrolo[1,2-a]benzimidazoles. The influence of experimental conditions on the course of reaction was investigated. A novel synthetic pathway starting from benzimidazoles unsubstituted at the five membered ring, alkyl bromoacetates and non-symmetrical electron-deficient alkynes in the molar ratio of 1:2:1, in 1,2-epoxybutane at reflux temperature, led directly to pyrrolo[1,2-a]quinoxalin-4-ones in fair yield by an one-pot three-component reaction. PMID:25383108

  14. Direct phosphonation of quinoxalin-2(1H)-ones under transition-metal-free conditions.

    PubMed

    Gao, Ming; Li, Yi; Xie, Lijuan; Chauvin, Remi; Cui, Xiuling

    2016-02-01

    A direct C-H bond phosphonation of quinoxalin-2(1H)-ones with H-phosphonates, H-phosphinates or H-phosphine oxides has been developed. A wide variety of heteroaryl phosphonates were obtained in up to 92% yield for 20 examples under transition-metal-free conditions. This protocol tolerates a broad scope of substrates and features practicality, high efficiency, environmental friendliness and atom economy. PMID:26779573

  15. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted phenyl azo substituted... Significant New Uses for Specific Chemical Substances § 721.3063 Substituted phenyl azo substituted phenyl... chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  16. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted phenyl azo substituted... Significant New Uses for Specific Chemical Substances § 721.3063 Substituted phenyl azo substituted phenyl... as substituted phenyl azo substituted phenyl esters (PMNs P-95-655, P-95-782 and P-95-871)...

  17. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted phenyl azo substituted... Significant New Uses for Specific Chemical Substances § 721.3063 Substituted phenyl azo substituted phenyl... chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs...

  18. Advances in the synthesis of imidazo[1,5-a]- and imidazo[1,2-a]quinoxalines

    NASA Astrophysics Data System (ADS)

    Mamedov, V. A.; Kalinin, A. A.

    2014-09-01

    This review is intended to generalize and systematize available information on the synthesis of imidazo[1,5-a]- and imidazo[1,2-a]quinoxalines. Relevant studies published in the last 10-15 years, as well as earlier studies less familiar to the broad chemical community, are surveyed. Major methods of formation of the imidazoquinoxaline system from substituted quinoxalines and imidazoles according to the type of bond being formed are presented. Special focus is placed on the radically new methods that enable the synthesis of various derivatives of these heterocyclic systems from available and inexpensive reagents. The mechanisms of formation of these compounds are discussed. Information on the biological activity of imidazo[1,5-a]- and imidazo[1,2-a]quinoxalines and examples of pharmaceuticals based on them are reported. The bibliography includes 179 references.

  19. Crystal structure of 1,3-bis-(2,3-di-methyl-quinoxalin-6-yl)benzene.

    PubMed

    Diesendruck, Charles E; Rubin, Gabrielle; Bertke, Jeffery A; Gray, Danielle L; Moore, Jeffrey S

    2015-12-01

    The title compound, C26H22N4 (I), was synthesized by C-H iridium-catalyzed borylation followed by Suzuki coupling. The mol-ecular structure of (I) consists of a central benzene ring with 3-di-methyl-quinoxalin-6-yl groups at the 1 and 3 positions. These 2,3-di-methyl-quinoxalin-6-yl groups twist significantly out of the plane of the benzene ring. There are inter-molecular π-π inter-actions which result in a two-dimensional extended structure. The layers extend parallel to the ab plane and stack along the c axis. PMID:26870397

  20. 4-Chlorotetrazolo[1,5-a]quinoxaline inhibits activation of Syk kinase to suppress mast cells in vitro and mast cell-mediated passive cutaneous anaphylaxis in mice

    SciTech Connect

    Park, Kui Lea; Ko, Na Young; Lee, Jun Ho; Kim, Do Kyun; Kim, Hyuk Soon; Kim, A-Ram; Her, Erk; Kim, Bokyung; Kim, Hyung Sik; Moon, Eun-Yi; Kim, Young Mi; Kim, Hang-Rae; Choi, Wahn Soo

    2011-12-15

    4-Chlorotetrazolo[1,5-a]quinoxaline is a quinoxaline derivative. We aimed to study the effects of 4-chlorotetrazolo[1,5-a]quinoxaline on activation of mast cells in vitro and in mice. 4-Chlorotetrazolo[1,5-a]quinoxaline reversibly inhibited degranulation of mast cells in a dose-dependent manner, and also suppressed the expression and secretion of TNF-{alpha} and IL-4 in mast cells. Mechanistically, 4-chlorotetrazolo[1,5-a]quinoxaline inhibited activating phosphorylation of Syk and LAT, which are crucial for early Fc{epsilon}RI-mediated signaling events, as well as Akt and MAP kinases, which play essential roles in the production of various pro-inflammatory cytokines in mast cells. Notably, although 4-chlorotetrazolo[1,5-a]quinoxaline inhibited the activation of Fyn and Syk, minimal inhibition was observed in mast cells in the case of Lyn. Furthermore, consistent with its in vitro activity, 4-chlorotetrazolo[1,5-a]quinoxaline significantly suppressed mast cell-mediated passive cutaneous anaphylaxis in mice. In summary, the results from this study demonstrate that 4-chlorotetrazolo[1,5-a]quinoxaline shows an inhibitory effect on mast cells in vitro and in vivo, and that this is mediated by inhibiting the activation of Syk in mast cells. Therefore, 4-chlorotetrazolo[1,5-a]quinoxaline could be useful in the treatment of mast cell-mediated allergic diseases. -- Highlights: Black-Right-Pointing-Pointer 4-chlorotetrazolo[1,5-a]quinoxaline is a quinoxaline derivative. Black-Right-Pointing-Pointer The effect of 4-chlorotetrazolo[1,5-a]quinoxaline on mast cells was investigated. Black-Right-Pointing-Pointer 4-chlorotetrazolo[1,5-a]quinoxaline reversibly inhibited Syk activation. Black-Right-Pointing-Pointer 4-chlorotetrazolo[1,5-a]quinoxaline could be useful for IgE-mediated allergy.

  1. Mode of Action of Quindoxin and Substituted Quinoxaline-di-N-Oxides on Escherichia coli

    PubMed Central

    Suter, W.; Rosselet, A.; Knüsel, F.

    1978-01-01

    The effect of quindoxin on the synthesis of deoxyribonucleic acid (DNA), ribonucleic acid, and protein in Escherichia coli KL 399 was examined under aerobic and anaerobic conditions. In the absence of oxygen the synthesis of DNA was completely inhibited by 10 ppm of quindoxin, whereas the syntheses of ribonucleic acid and protein were not affected. Quinoxalin-di-N-oxides (QdNO) induce degradation of DNA in both proliferating and non-proliferating cells. polA, recA, recB, recC, exrA, and uvrA mutants were more susceptible than the corresponding repair-proficient strains. All strains were more resistant in the presence of oxygen. Quindoxin was reduced to quinoxalin-N-oxide by intact E. coli cells or by a cell-free E. coli extract. Electron spin resonance measurements demonstrated the generation of free radicals during the reduction of quindoxin. Oxygen or deficiency of energy sources impaired the antibiotic activity and the reduction of QdNO. The QdNO reductase activity was demonstrated to be lower in QdNO-resistant mutants than in the susceptible parent strain. Based on these results it is concluded that an intermediate of reduction, probably a free radical, is responsible for the lethal effect of quindoxin. With three independent techniques no evidence has been found for binding of quindoxin to DNA. Images PMID:352264

  2. in Silico investigation of the structural requirements for the AMPA receptor antagonism by quinoxaline derivatives

    PubMed Central

    Azam, Faizul; Abugrain, Ismaiel Mohamed; Sanalla, Mohamed Hussin; Elnaas, Radwan Fatahalla; Rajab, Ibrahim Abdassalam Ibn

    2013-01-01

    Glutamate receptors have been implicated in various neurological disorders and their antagonism offers a suitable approach for the treatment of such disorders. The field of drug design and discovery aims to find best medicines to prevent, treat and cure diseases quickly and efficiently. In this regard, computational tools have helped medicinal chemists modify and optimize molecules to potent drug candidates with better pharmacokinetic profiles, and guiding biologists and pharmacologists to explore new disease genes as well as novel drug targets. In the present study, to understand the structural requirements for AMPA receptor antagonism, molecular docking study was performed on 41 structurally diverse antagonists based on quinoxaline nucleus. Lamarckian genetic algorithm methodology was employed for docking simulations using AutoDock 4.2 program. The results obtained signify that the molecular docking approach is reliable and produces a good correlation coefficient (r2 = 0.6) between experimental and docking predicted AMPA receptor antagonistic activity. The aromatic moiety of quinoxaline core has been proved to be vital for hydrophobic contacts exhibiting - interactions in docked conformations. However, polar moieties such as carboxylic group and 1,2,4-triazole moieties were noted to be sites for hydrophilic interactions in terms of hydrogen bonding with the receptor. These analyses can be exploited to design and develop novel AMPA receptor antagonists for the treatment of different neurological disorders. PMID:24250113

  3. Quinoxaline derivatives as corrosion inhibitors for mild steel in hydrochloric acid medium: Electrochemical and quantum chemical studies

    NASA Astrophysics Data System (ADS)

    Olasunkanmi, Lukman O.; Kabanda, Mwadham M.; Ebenso, Eno E.

    2016-02-01

    The corrosion inhibition potential of four quinoxaline derivatives namely, 1-[3-(4-methylphenyl)-5-(quinoxalin-6-yl)-4,5-dihydropyrazol-1-yl]butan-1-one (Me-4-PQPB), 1-(3-(4-methoxyphenyl)-5-(quinoxalin-6-yl)-4,5-dihydropyrazol-1-yl)butan-1-one (Mt-4-PQPB), 1-[3-(3-methoxyphenyl)-5-(quinoxalin-6-yl)-4,5-dihydropyrazol-1-yl]butan-1-one (Mt-3-PQPB) and 1-[3-(2H-1,3-benzodioxol-5-yl)-5-(quinoxalin-6-yl)-4,5-dihydropyrazol-1-yl]butan-1-one (Oxo-1,3-PQPB) was studied for mild steel corrosion in 1 M HCl solution using electrochemical, spectroscopic techniques and quantum chemical calculations. The results of both potentiodynamic polarization and electrochemical impedance spectroscopic studies revealed that the compounds are mixed-type inhibitors and the order of corrosion inhibition efficiency at 100 ppm is Me-4-PQPB>Mt-3-PQPB>Oxo-1,3-PQPB>Mt-4-PQPB. Fourier transform infrared (FTIR) and ultraviolet-visible (UV-vis) spectroscopic analyses confirmed the presence of chemical interactions between the inhibitors and mild steel surface. The adsorption of the inhibitor molecules on mild steel surface was found to be both physisorption and chemisorption but predominantly chemisorption. The experimental data obey Langmuir adsorption isotherm. Scanning electron microscopy studies revealed the formation of protective films of the inhibitors on mild steel surface. Quantum chemical parameters obtained from density functional theory (DFT) calculations support experimental results.

  4. Radiation-induced reduction of quinoxalin-2-one derivatives in aqueous solutions

    NASA Astrophysics Data System (ADS)

    Skotnicki, Konrad; De la Fuente, Julio R.; Cañete, Alvaro; Bobrowski, Krzysztof

    2016-07-01

    Quinoxaline-2-one derivatives have been proposed as potential drugs in treatments of various diseases since some of them showed a variety of pharmacological properties. The kinetics and spectral characteristics of the transients formed in the reactions of hydrated electrons (eaq-) with quinoxalin-2-(1H)-one (Q) and its methyl derivative, 3-methyl quinoxalin-2-(1H)-one (3-MeQ) were studied by pulse radiolysis in aqueous solutions at pH ranging from 5 to 14. The transient absorption spectra recorded in the reactions of (eaq-) with Q and 3-MeQ at pH 7 consisted of a broad, almost flat band in the range 390-450 nm and were assigned to the respective protonated radical anions (QH•/3-MeQH•) at N4 atom in a pyrazin-2-one ring. On the other hand, the transient absorption spectra recorded in the reactions of (eaq-) with Q and 3-MeQ at pH 13 are characterized by a broad band with a much better pronounced maximum at λmax=390 nm and higher intensity (in comparison to that at pH 7) and were assigned to the respective radical anions (Q•-/3-MeQ•-). Both forms are involved in the prototropic equilibrium with the pKa located at pH≥13.5. The rate constants of the reactions of (eaq-) with Q and 3-MeQ were found to be at pH 7 (2.6±0.1)×1010 M-1 s-1 and (2.1±0.1)×1010 M-1 s-1 and at pH 13 (1.6±0.1)×1010 M-1 s-1 and (1.3±0.1)×1010 M-1 s-1, respectively. Semi-empirical quantum mechanical calculations reproduce fairly well the spectral features of the experimental absorption spectra and show that protonated radical anions at nitrogen atom (N4) in both molecules are the most stable hydrogenated radicals.

  5. Fourier transform microwave and millimeter wave spectroscopy of quinazoline, quinoxaline, and phthalazine.

    PubMed

    McNaughton, Don; Godfrey, Peter D; Jahn, Michaela K; Dewald, David A; Grabow, Jens-Uwe

    2011-04-21

    The pure rotational spectra of the bicyclic aromatic nitrogen heterocycle molecules, quinazoline, quinoxaline, and phthalazine, have been recorded and assigned in the region 13-87 GHz. An analysis, guided by ab initio molecular orbital predictions, of frequency-scanned Stark modulated, jet-cooled millimeter wave absorption spectra (48-87 GHz) yielded a preliminary set of rotational and centrifugal distortion constants. Subsequent spectral analysis at higher resolution was carried out with Fourier transform microwave (FT-MW) spectroscopy (13-18 GHz) of a supersonic rotationally cold molecular beam. The high spectral resolution of the FT-MW instrument provided an improved set of rotational and centrifugal distortion constants together with nitrogen quadrupole coupling constants for all three species. Density functional theory calculations at the B3LYP∕6-311+G∗∗ level of theory closely predict rotational constants and are useful in predicting quadrupole coupling constants and dipole moments for such species. PMID:21513385

  6. Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress.

    PubMed

    Loughran, H Marie; Han, Ziying; Wrobel, Jay E; Decker, Sarah E; Ruthel, Gordon; Freedman, Bruce D; Harty, Ronald N; Reitz, Allen B

    2016-08-01

    We prepared a series of quinoxalin-2-mercapto-acetyl-urea analogs and evaluated them for their ability to inhibit viral egress in our Marburg and Ebola VP40 VLP budding assays in HEK293T cells. We also evaluated selected compounds in our bimolecular complementation assay (BiMC) to detect and visualize a Marburg mVP40-Nedd4 interaction in live mammalian cells. Antiviral activity was assessed for selected compounds using a live recombinant vesicular stomatitis virus (VSV) (M40 virus) that expresses the EBOV VP40 PPxY L-domain. Finally selected compounds were evaluated in several ADME assays to have an early assessment of their drug properties. Our compounds had low nM potency in these assays (e.g., compounds 21, 24, 26, 39), and had good human liver microsome stability, as well as little or no inhibition of P450 3A4. PMID:27377328

  7. In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis.

    PubMed

    Kaplum, Vanessa; Cogo, Juliana; Sangi, Diego Pereira; Ueda-Nakamura, Tânia; Corrêa, Arlene Gonçalves; Nakamura, Celso Vataru

    2016-06-01

    Leishmaniasis is endemic in 98 countries and territories worldwide. The therapies available for leishmaniasis have serious side effects, thus prompting the search for new therapies. The present study investigated the antileishmanial activities of 2,3-diarylsubstituted quinoxaline derivatives against Leishmania amazonensis The antiproliferative activities of 6,7-dichloro-2,3-diphenylquinoxaline (LSPN329) and 2,3-di-(4-methoxyphenyl)-quinoxaline (LSPN331) against promastigotes and intracellular amastigotes were assessed, and the cytotoxicities of LSPN329 and LSPN331 were determined. Morphological and ultrastructural alterations were examined by electron microscopy, and biochemical alterations, reflected by the mitochondrial membrane potential (ΔΨm), mitochondrial superoxide anion (O2·(-)) concentration, the intracellular ATP concentration, cell volume, the level of phosphatidylserine exposure on the cell membrane, cell membrane integrity, and lipid inclusions, were evaluated. In vivo antileishmanial activity was evaluated in a murine cutaneous leishmaniasis model. Compounds LSPN329 and LSPN331 showed significant selectivity for promastigotes and intracellular amastigotes and low cytotoxicity. In promastigotes, ultrastructural alterations were observed, including an increase in lipid inclusions, concentric membranes, and intense mitochondrial swelling, which were associated with hyperpolarization of ΔΨm, an increase in the O2·(-) concentration, decreased intracellular ATP levels, and a decrease in cell volume. Phosphatidylserine exposure and DNA fragmentation were not observed. The cellular membrane remained intact after treatment. Thus, the multifactorial response that was responsible for the cellular collapse of promastigotes was based on intense mitochondrial alterations. BALB/c mice treated with LSPN329 or LSPN331 showed a significant decrease in lesion thickness in the infected footpad. Therefore, the antileishmanial activity and mitochondrial mechanism of

  8. Discovery of indeno[1,2-b]quinoxaline derivatives as potential anticancer agents.

    PubMed

    Tseng, Chih-Hua; Chen, You-Ren; Tzeng, Cherng-Chyi; Liu, Wangta; Chou, Chon-Kit; Chiu, Chien-Chih; Chen, Yeh-Long

    2016-01-27

    We have synthesized certain indeno[1,2-b]quinoxaline derivatives for antiproliferative evaluation. Among them, 11-{[3-(dimethylamino)propoxy]imino}-N-[3-(dimethylamino) propyl]-11H-indeno[1,2-b]quinoxaline-6-carboxamide (10a) was active against the growth of MDA-MB231, PC-3, and Huh-7 with IC50 values of 0.87 (selectivity index, SI = 36.22), 0.82 (SI = 38.43), and 0.64 μM (SI = 49.23) respectively. Compound 10a was inactive against the growth of normal human fetal lung fibroblast cell line (MRC-5) with an IC50 value of 31.51 μM. Its analogs, 10b and 10c, were also active against the growth of MB231, PC-3, and Huh-7 with IC50 values of <1.0 μM in each case. Our results have also indicated compounds 10a-10c exhibited comparable inhibitory activities against topo I and topo II with the positive compound 2 at a concentration of 10 μM. Mechanism studies indicated that compound 10a induced cell cycle arrest at S phase via activation of caspase-3, -7 and an increase in the protein expression of Bad and Bax but a decrease in expression of Bcl-2 and PARP, which consequently cause cell death. In addition, compound 10a attenuated the levels of phosphorylated Src, Akt-1, and Akt-2 protein levels but did not affect the total protein expression of Akt. We have also implanted human hepatocellular carcinoma cells into the yolk sac of zebrafish larvae and incubated larvae with various concentrations of 10a. Our results of the zebrafish xenograft assay confirmed the anti-tumor effect of 10ain vivo. PMID:26686931

  9. 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...

  10. 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...

  11. 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.

  12. Activity of a novel quinoxaline derivative against human immunodeficiency virus type 1 reverse transcriptase and viral replication.

    PubMed Central

    Kleim, J P; Bender, R; Billhardt, U M; Meichsner, C; Riess, G; Rösner, M; Winkler, I; Paessens, A

    1993-01-01

    S-2720 [6-chloro-3,3-dimethyl-4-(isopropenyloxycarbonyl)-3,4- dihydroquinoxalin-2(1H)-thione], a quinoxaline derivative, was found to be a very potent inhibitor of both human immunodeficiency virus type 1 reverse transcriptase (HIV-1 RT) activity and HIV-1 replication in tissue culture. Like other nonnucleoside RT inhibitors, S-2720 does not affect the HIV-2 RT. A S-2720-resistant virus was selected and shown to possess a mutation within the RT-coding region that has not previously been described. Notably, this mutation gives rise to a dramatic decrease in enzyme activity. S-2720, therefore, belongs to a new class of RT inhibitors that bind differently to the RT than other known nonnucleoside RT inhibitors. As no toxic effects were observed with S-2720 in mice, these quinoxaline derivatives deserve further evaluation to prove their potency as possible therapeutic agents for HIV-1 infection. PMID:7692812

  13. A simple strategy to the side chain functionalization on the quinoxaline unit for efficient polymer solar cells.

    PubMed

    Yuan, Jun; Qiu, Lixia; Zhang, Zhiguo; Li, Yongfang; He, Yuehui; Jiang, Lihui; Zou, Yingping

    2016-05-25

    A new tetrafluoridequinoxaline electron accepting block from a quinoxaline core, which is substituted with a fluorine atom onto its backbone and side chains, was designed. A new copolymer (PBDTT-ffQx) was synthesized from tetrafluoridequinoxaline and benzodithiophene. The copolymer was characterized in detail. The photovoltaic properties were well investigated. A high PCE of 8.6% based on the single junction device was obtained. PMID:27025274

  14. Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: mechanisms correlated to charge distributions

    PubMed Central

    Zhang, Yiliang; Sheets, Matthew R.; Raja, Erum K.; Boblak, Kenneth N.

    2011-01-01

    The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl-substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges. PMID:21548654

  15. Conjugated poly(fluorene-quinoxaline) for fluorescence imaging and chemical detection of nerve agents with its paper-based strip.

    PubMed

    Jo, Seonyoung; Kim, Daigeun; Son, Sang-Ho; Kim, Yongkyun; Lee, Taek Seung

    2014-01-22

    Conjugated polymer of poly(fluorene-co-quinoxaline) was synthesized via Suzuki coupling polymerization. The emission color of the polymer can be tuned depending on the concentration of the polymer in solution. A low-energy bandgap is observed both in the concentrated solution and in the solid state, caused by aggregation of the polymer chains, resulting in long wavelength emission from the quinoxaline moiety, while short wavelength emission can be seen in diluted, well-dissolved solution. The presence of quinoxaline units enables us to demonstrate fluorescence switching and imaging. Paper-based strips containing the polymer are prepared via simple immersion of filter paper in the polymer solution for practical use in the detection of nerve agents. The emission of the paper-based strip is quenched upon exposure to diethyl chlorophosphate (DCP), a nerve agent simulant, and the initial emission intensity can be almost restored by treatment with aqueous sodium hydroxide solution, making a possible reversible paper-based sensor. PMID:24372409

  16. Trimerization of Phenyl Cyanate Ester

    NASA Astrophysics Data System (ADS)

    Pallaka, Madhusudhan Reddy; Simon, Sindee L.

    2015-03-01

    The kinetics of phenyl cyanate ester trimerization is studied in the bulk using differential scanning calorimetry. Dynamic experiments for different heating rates are analyzed for the activation energy using the model-free Kissinger-Akahira-Sunose(KAS) isoconversion method. The activation energy and other kinetic parameters are also obtained by fitting the dynamic data to a first order autocatalytic reaction model, which well describes the experimental data. The activation energy obtained from the KAS isoconversion method (70.1 kJ/mol) is in good agreement with that obtained from the kinetic model (73.2 kJ/mol) and is much lower than the more bulky cyanate esters studied in our laboratory, which have activation energies of approximately 95 kJ/mol. In addition, the rate constant for the phenyl cyanate ester is one to two orders higher than the bulkier cyanate esters in the temperature range of 200 to 300°C. Further elucidation of the dynamic experiments revealed a strong dependence of the reaction kinetics on the sample weight. Future work aims to understand this finding.

  17. Vertical and lateral morphology effects on solar cell performance for a thiophene–quinoxaline copolymer:PC 70BM blend

    SciTech Connect

    Hansson, Rickard; Ericsson, Leif K. E.; Holmes, Natalie P.; Rysz, Jakub; Opitz, Andreas; Campoy-Quiles, Mariano; Wang, Ergang; Barr, Matthew G.; Kilcoyne, A. L. David; Zhou, Xiaojing; Dastoor, Paul; Moons, Ellen

    2015-02-13

    The distribution of electron donor and acceptor in the active layer is known to strongly influence the electrical performance of polymer solar cells for most of the high performance polymer:fullerene systems. The formulation of the solution from which the active layer is spincoated plays an important role in the quest for morphology control. We have studied how the choice of solvent and the use of small amounts of a low vapour pressure additive in the coating solution influence the film morphology and the solar cell performance for blends of poly[2,3-bis-(3-octyloxyphenyl)quinoxaline-5,8-diyl-alt-thiophene-2,5-diyl] (TQ1) and [6,6]-phenyl C71-butyric acid methyl ester (PC70BM). We have investigated the lateral morphology using atomic force microscopy (AFM) and scanning transmission X-ray microscopy (STXM), the vertical morphology using dynamic secondary ion mass spectrometry (d-SIMS) and variable-angle spectroscopic ellipsometry (VASE), and the surface composition using near-edge X-ray absorption fine structure (NEXAFS). The lateral phase-separated domains observed in films spincoated from single solvents, increase in size with increasing solvent vapour pressure and decreasing PC70BM solubility, but are not observed when 1-chloronaphthalene (CN) is added. A strongly TQ1-enriched surface layer is formed in all TQ1:PC70BM blend films and rationalized by surface energy differences. The photocurrent and power conversion efficiency strongly increased upon the addition of CN, while the leakage current decreased by one to two orders of magnitude. The higher photocurrent correlates with the finer lateral structure and stronger TQ1-enrichment at the interface with the electron-collecting electrode. This indicates that the charge transport and collection are not hindered by this polymer-enriched surface layer. Neither the open-circuit voltage nor the series resistance of the devices are sensitive to the differences in morphology.

  18. Further investigations into the genotoxicity of quinoxaline-di-N-oxides and their primary metabolites.

    PubMed

    Liu, Qianying; Zhang, Jianwu; Luo, Xun; Ihsan, Awais; Liu, Xianglian; Dai, Menghong; Cheng, Guyue; Hao, Haihong; Wang, Xu; Yuan, Zonghui

    2016-07-01

    Quinoxaline-di-N-oxides (QdNOs) are potential antibacterial agents with a wide range of biological properties. Quinocetone (QCT), carbadox (CBX), olaquindox (OLA), mequindox (MEQ) and cyadox (CYA) are classical QdNOs. Though the genotoxicity of parent drugs has been evaluated, the genotoxicity of their primary N → O reduced metabolites remains unclear. In the present study, a battery of four different short-term tests, mouse lymphoma assay (MLA), Ames test, chromosomal aberration assay in vitro and bone marrow erythrocyte micronucleus assay in vivo was carried out to investigate the genotoxicity of the six primary N → O reduced metabolites. Additionally, the genotoxicity of five parent drugs was evaluated by the MLA. Strong genotoxicity of N1-MEQ, B-MEQ and B-CBX was found in three of the assays but not in the Ames assay, and the rank order was N1-MEQ>B-MEQ>B-CBX that is consistent with prototype QdNOs. Negative results for the five QdNOs were noted in the MLA. We present for the first time a comparison of the genotoxicity of primary N → O reduced metabolites, and evaluate the ability of five QdNOs to cause mutations in the MLA. The present study demonstrates that metabolites are involved in genetic toxicity mediated by QdNOs, and improve the prudent use of QdNOs for public health. PMID:27170491

  19. Potent and selective inhibition of polycythemia by the quinoxaline JAK2 inhibitor NVP-BSK805.

    PubMed

    Baffert, Fabienne; Régnier, Catherine H; De Pover, Alain; Pissot-Soldermann, Carole; Tavares, Gisele A; Blasco, Francesca; Brueggen, Josef; Chène, Patrick; Drueckes, Peter; Erdmann, Dirk; Furet, Pascal; Gerspacher, Marc; Lang, Marc; Ledieu, David; Nolan, Lynda; Ruetz, Stephan; Trappe, Joerg; Vangrevelinghe, Eric; Wartmann, Markus; Wyder, Lorenza; Hofmann, Francesco; Radimerski, Thomas

    2010-07-01

    The recent discovery of an acquired activating point mutation in JAK2, substituting valine at amino acid position 617 for phenylalanine, has greatly improved our understanding of the molecular mechanism underlying chronic myeloproliferative neoplasms. Strikingly, the JAK2(V617F) mutation is found in nearly all patients suffering from polycythemia vera and in roughly every second patient suffering from essential thrombocythemia and primary myelofibrosis. Thus, JAK2 represents a promising target for the treatment of myeloproliferative neoplasms and considerable efforts are ongoing to discover and develop inhibitors of the kinase. Here, we report potent inhibition of JAK2(V617F) and JAK2 wild-type enzymes by a novel substituted quinoxaline, NVP-BSK805, which acts in an ATP-competitive manner. Within the JAK family, NVP-BSK805 displays more than 20-fold selectivity towards JAK2 in vitro, as well as excellent selectivity in broader kinase profiling. The compound blunts constitutive STAT5 phosphorylation in JAK2(V617F)-bearing cells, with concomitant suppression of cell proliferation and induction of apoptosis. In vivo, NVP-BSK805 exhibited good oral bioavailability and a long half-life. The inhibitor was efficacious in suppressing leukemic cell spreading and splenomegaly in a Ba/F3 JAK2(V617F) cell-driven mouse mechanistic model. Furthermore, NVP-BSK805 potently suppressed recombinant human erythropoietin-induced polycythemia and extramedullary erythropoiesis in mice and rats. PMID:20587663

  20. Spectroscopic properties and the catalytic activity of new organo-lead supramolecular coordination polymer containing quinoxaline

    NASA Astrophysics Data System (ADS)

    Etaiw, Safaa El-din H.; Abdou, Safaa N.

    2015-01-01

    The 3D-supramolecular coordination polymer (SCP) 3∞[ Cu2(CN)3(Me3Pb)(qox)], 1, as the first example of the CuCN SCP containing the (Me3Pb) fragment, was explored to investigate its catalytic and photo-catalytic activities. The structure of 1 contains two chemically identical but crystallographically different [Cu2(CN)3ṡMe3Pbṡqox]2 units with four Cu(I) sites assuming distorted TP-3 geometry. Two non-linear chains of equal abundance are formed producing corrugated parallel chains which are connected laterally by quinoxaline creating 2D-layers which are arranged parallel in an (AB⋯AB⋯AB)n fashion forming 3D-network. IR, mass, electronic absorption and fluorescence spectra are also investigated. The SCP 1 is diamagnetic and exhibits good catalytic and photo-catalytic activities for the degradation of methylene blue (MB). The reaction is first order with respect to MB dye. The irradiation of the reaction with UV-light enhanced the rate of MB mineralization. The efficiency of recycled the 1 and the mechanism of degradation of MB dye were investigated.

  1. Spectroscopic properties and the catalytic activity of new organo-lead supramolecular coordination polymer containing quinoxaline.

    PubMed

    Etaiw, Safaa El-din H; Abdou, Safaa N

    2015-01-25

    The 3D-supramolecular coordination polymer (SCP) (3)∞[ Cu2(CN)3(Me3Pb)(qox)], 1, as the first example of the CuCN SCP containing the (Me3Pb) fragment, was explored to investigate its catalytic and photo-catalytic activities. The structure of 1 contains two chemically identical but crystallographically different [Cu2(CN)3⋅Me3Pb⋅qox]2 units with four Cu(I) sites assuming distorted TP-3 geometry. Two non-linear chains of equal abundance are formed producing corrugated parallel chains which are connected laterally by quinoxaline creating 2D-layers which are arranged parallel in an (AB⋯AB⋯AB)n fashion forming 3D-network. IR, mass, electronic absorption and fluorescence spectra are also investigated. The SCP 1 is diamagnetic and exhibits good catalytic and photo-catalytic activities for the degradation of methylene blue (MB). The reaction is first order with respect to MB dye. The irradiation of the reaction with UV-light enhanced the rate of MB mineralization. The efficiency of recycled the 1 and the mechanism of degradation of MB dye were investigated. PMID:25124847

  2. Quinoxaline 1,4-di-N-Oxides: Biological Activities and Mechanisms of Actions

    PubMed Central

    Cheng, Guyue; Sa, Wei; Cao, Chen; Guo, Liangliang; Hao, Haihong; Liu, Zhenli; Wang, Xu; Yuan, Zonghui

    2016-01-01

    Quinoxaline 1,4-di-N-oxides (QdNOs) have manifold biological properties, including antimicrobial, antitumoral, antitrypanosomal and antiinflammatory/antioxidant activities. These diverse activities endow them broad applications and prospects in human and veterinary medicines. As QdNOs arouse widespread interest, the evaluation of their medicinal chemistry is still in progress. In the meantime, adverse effects have been reported in some of the QdNO derivatives. For example, genotoxicity and bacterial resistance have been found in QdNO antibacterial growth promoters, conferring urgent need for discovery of new QdNO drugs. However, the modes of actions of QdNOs are not fully understood, hindering the development and innovation of these promising compounds. Here, QdNOs are categorized based on the activities and usages, among which the antimicrobial activities are consist of antibacterial, antimycobacterial and anticandida activities, and the antiprotozoal activities include antitrypanosomal, antimalarial, antitrichomonas, and antiamoebic activities. The structure-activity relationship and the mode of actions of each type of activity of QdNOs are summarized, and the toxicity and the underlying mechanisms are also discussed, providing insight for the future research and development of these fascinating compounds. PMID:27047380

  3. 3-[2-(3-Methyl­quinoxalin-2-yl­oxy)eth­yl]-1,3-oxazolidin-2-one

    PubMed Central

    Ahoya, Caleb Anothane; Bouhfid, Rachid; Daouda, Ballo; Essassi, El Mokhtar; El Ammari, Lahcen

    2010-01-01

    Two isomers were isolated during the reaction between 3-methyl­quinoxalin-2-one and bis­(2-chloro­ethyl)amine hydro­chloride. The crystal structure of one isomer has already been reported [Caleb, Bouhfid, Essassi & El Ammari (2009). Acta Cryst. E65, o2024–o2025], while that of the second isomer is the subject of this work. The title compound, C14H15N3O3, has a new structure containing oxazolidine and quinoxaline rings linked by an eth­oxy group. The main difference between the two isomers is the position of the oxazolidine group with respect to the quinoxaline system. The dihedral angle between the fused planar rings and the oxazolidin-2-one ring is 41.63 (8)° in the title mol­ecule. PMID:21579110

  4. Highly efficient synthesis of quinoxaline derivatives from 1,2-benzenediamine and [Formula: see text]-aminoxylated 1,3-dicarbonyl compounds.

    PubMed

    Yan, Jianwei; Xu, Yanhong; Zhuang, Fangfang; Tian, Jie; Zhang, Guisheng

    2016-05-01

    Simple and efficient synthetic procedures for the preparation of quinoxaline, pyrazine, pyridopyrazine, and benzoxazin-2-one derivatives were developed. The one-pot cascade process involves the acidic elimination of [Formula: see text]-aminoxylated dicarbonyl compounds to generate 1,2,3-tricarbonyl compounds and subsequent condensation with 1,4-N,N or -N,O dinucleophiles to afford quinoxaline, pyrazine, pyridopyrazine, and benzoxazin-2-one scaffolds. All the proposed processes do not need extra catalysts, dry solvents, or harsh reaction conditions. PMID:26797715

  5. In vitro and in vivo anti-glioma activity of a chalcone-quinoxaline hybrid.

    PubMed

    Loch-Neckel, Gecioni; Bicca, Maíra Assunção; Leal, Paulo César; Mascarello, Alessandra; Siqueira, Jarbas Mota; Calixto, João B

    2015-01-27

    Chalcones are important compounds that exhibit multiple biological activities, including anti-inflammatory, antimitotic and antibacterial properties. In the present study, we have analyzed the potential anti-cancer activity of a chalcone named N9 (a hybrid chalcone-quinoxaline compound) using in vitro and in vivo experimental glioma models. Here, we report N9-induced inhibition of cell proliferation and also N9-induced cell death in a concentration-dependent manner in U87-MG glioma cells. These effects of N9 appear to be associated with its ability to inhibit the expression of cell cycle-associated proteins, and also the augmentation in the expression of the p21 (p21/Cip1) protein, a cyclin-dependent kinase inhibitor. Additionally, N9 also potentiates the production of the pro-apoptotic markers Bax and p53 via inhibition of MDM2. Moreover, our results show that N9 also significantly enhanced apoptosis of U87-MG cells with disruption of mitochondrial membrane potential, generation of ROS and caspase-9 activation. In vivo experiments carried out in a murine xenograft model of U87-MG revealed that N9 produced a significant reduction of tumors volume when compared to vehicle treated mice. Collectively, data demonstrate that N9 possess in vitro and in vivo anti-cancer activity, an effect that seems to involve the induction of p53 and p21 proteins, as well as, the activation of mitochondrial apoptosis pathway associated with the inhibition of protein MDM2. Overall, this study suggests N9 is affecting a variety of intracellular pathways related to tumor apoptosis. Perhaps N9 or derivate molecules could represent new potential drugs for cancer therapeutics. PMID:25461314

  6. One-Pot Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines and Isoquinolino[3,4-b]quinoxalines via Tandem Cyclization Strategies.

    PubMed

    Bagdasarian, Alex L; Nguyen, Huy H; Palazzo, Teresa A; Fettinger, James C; Haddadin, Makhluf J; Kurth, Mark J

    2016-05-01

    Two operationally simple one-pot protocols have been developed for the synthesis of amino-functionalized benzo[4,5]imidazo[2,1-a]isoquinolines and isoquinolino[3,4-b]quinoxalines. Optimization data and substrate scope for these atom-economical transformations, which engage commercially available o-phenylenediamines and o-cyanobenzaldehydes, are discussed. PMID:27030441

  7. Ferrocene-quinoxaline Y-shaped chromophores as fascinating second-order NLO building blocks for long lasting highly active SHG polymeric films.

    PubMed

    Senthilkumar, Kabali; Thirumoorthy, Krishnan; Dragonetti, Claudia; Marinotto, Daniele; Righetto, Stefania; Colombo, Alessia; Haukka, Matti; Palanisami, Nallasamy

    2016-07-26

    The first example of a Y-shaped ferrocene quinoxaline derivative with a surprisingly high and stable second harmonic generation (SHG) response in composite polymeric films is reported. The interesting quadratic hyperpolarizability values of different substituted Y-shaped chromophores are also investigated in solution by the EFISH technique. PMID:27402322

  8. Coordinated assembly of a new 3D mesoporous Fe₃O₄@Cu₂O-graphene oxide framework as a highly efficient and reusable catalyst for the synthesis of quinoxalines.

    PubMed

    Wang, Zhiyi; Hu, Guowen; Liu, Jian; Liu, Weisheng; Zhang, Haoli; Wang, Baodui

    2015-03-25

    A new three-dimensional (3D) mesoporous hybrid framework was synthesized by coordinated layer-by-layer assembly between nanosheets of reduced graphene oxide and Fe3O4@Cu2O. This 3D mesoporous framework shows an excellent catalytic performance with a remarkable activity, selectivity (>99%), and strong durability in the synthesis of quinoxalines. PMID:25712163

  9. A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate.

    PubMed

    Piltan, Mohammad; Moradi, Loghman; Abasi, Golaleh; Zarei, Seyed Amir

    2013-01-01

    The catalyst-free multicomponent reaction of 1,2-diaminobenzene, dialkyl acetylenedicarboxylates, and ethyl bromopyruvate forms pyrrolo[1,2-a]quinoxaline derivatives in good yields. Ethylenediamine also reacts under similar conditions to produce new pyrrolo[1,2-a]pyrazine derivatives. PMID:23616791

  10. Synthesis and characterization of different zinc(II) oxide nano-structures from two new zinc(II)-Quinoxaline coordination polymers

    NASA Astrophysics Data System (ADS)

    Molaei, Fatemeh; Bigdeli, Fahime; Morsali, Ali; Joo, Sang Woo; Bruno, Giuseppe; Rudbari, Hadi Amiri

    2015-09-01

    Two new zinc(II) coordination polymers, [Zn(Quinoxaline)(NO3)2(H2O)2]nṡQuinoxaline·H2O (1) and [Zn(Quinoxaline)2(Br)2]n (2), Quinoxaline = Benzopyrazine, have been synthesized and characterized by IR spectroscopy. Compounds 1 and 2 were structurally characterized by single crystal X-ray diffraction and are one-dimensional coordination polymers with coordination environment of octahedral and tetrahedral respectively. Nanostructures of zinc(II) oxide were obtained by thermolyses of compound 1 in oleic acid, calcination of compound 1 at 500 °C under air atmosphere and sol-gel processes. Also, nanopowders of zinc(II) oxide were obtained by calcination of compound 2 at 450 and 550 °C. The nanomaterials were characterized by scanning electron microscopy and X-ray powder diffraction (XRD). The thermal stability of compounds 1 and 2 both their bulk were studied by thermo-gravimetric (TGA) and differential thermal analyses (DTA). This study demonstrates the coordination polymers may be suitable precursors for the preparation of nanoscale materials.

  11. 40 CFR 721.3430 - 4-Bromophenyl phenyl ether.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 4-Bromophenyl phenyl ether. 721.3430... Substances § 721.3430 4-Bromophenyl phenyl ether. (a) Chemical substance and significant new use subject to reporting. (1) The chemical substance 4-bromophenyl phenyl ether (CAS No. 101-55-3) is subject to...

  12. 40 CFR 721.3430 - 4-Bromophenyl phenyl ether.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false 4-Bromophenyl phenyl ether. 721.3430... Substances § 721.3430 4-Bromophenyl phenyl ether. (a) Chemical substance and significant new use subject to reporting. (1) The chemical substance 4-bromophenyl phenyl ether (CAS No. 101-55-3) is subject to...

  13. 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...

  14. 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...

  15. 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...

  16. 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...

  17. 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...

  18. 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.

  19. Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides.

    PubMed

    Aichhorn, Stefan; Himmelsbach, Markus; Schöfberger, Wolfgang

    2015-09-28

    Pyrazino compounds such as quinoxalines are 1,4-diazines with widespread occurrence in nature. Quinolin-8-amines are isomerically related and valuable scaffolds in organic synthesis. Herein, we present intramolecular main group metal Lewis acid catalyzed formal hydroamination as well as hydroarylation methodology using mono-propargylated aromatic ortho-diamines. The annulations can be conducted utilizing equal aerobic conditions with either stannic chloride or indium(iii) chloride and represent primary examples for main group metal catalyzed 6-exo-dig and 6-endo-dig, respectively, cyclizations in such settings. Both types of reactions can also be utilized in a one-pot manner starting from ortho-nitro N-propargyl anilines using stoichiometric amounts SnCl2·2H2O or In powder. Mechanistic considerations are presented regarding the substituent-depending regioselectivity. PMID:26280508

  20. High-performance fluorescence sensing of lanthanum ions (La(3+)) by a polydentate pyridyl-based quinoxaline derivative.

    PubMed

    Zhao, Qiang; Liu, Xiu-Ming; Li, Huan-Rong; Zhang, Ying-Hui; Bu, Xian-He

    2016-06-28

    A polydentate pyridyl derivative, 2,3,6,7,10,11-hexa(2-pyridyl)-dipyrazino [2,3-f:2',3'-h]quinoxaline (HPDQ), exhibits a high-performance fluorescence response to La(3+) with an ∼65 nm redshifted emission wavelength and 38 fold enhanced intensity, in contrast to its weakened emission for other lanthanide ions. The final La(3+) coordination complex in solution has a stoichiometric ratio of 1 : 3 of ligand-to-metal, as testified by the Job's plot and single crystal structure analyses. The red shift of the luminescence emission as well as UV-vis absorption was rationalized in terms of the change of the electron structure as indicated by nuclear magnetic titration, electrochemical experiment and density functional theoretical calculation, while the significant enhancement of emission was attributed to the enhanced π conjugated extent of HPDQ caused by La(3+) coordination. PMID:27297084

  1. Discovery and Optimization of Macrocyclic Quinoxaline-pyrrolo-dihydropiperidinones as Potent Pim-1/2 Kinase Inhibitors.

    PubMed

    Cee, Victor J; Chavez, Frank; Herberich, Bradley; Lanman, Brian A; Pettus, Liping H; Reed, Anthony B; Wu, Bin; Wurz, Ryan P; Andrews, Kristin L; Chen, Jie; Hickman, Dean; Laszlo, Jimmy; Lee, Matthew R; Guerrero, Nadia; Mattson, Bethany K; Nguyen, Yen; Mohr, Christopher; Rex, Karen; Sastri, Christine E; Wang, Paul; Wu, Qiong; Wu, Tian; Xu, Yang; Zhou, Yihong; Winston, Jeffrey T; Lipford, J Russell; Tasker, Andrew S; Wang, Hui-Ling

    2016-04-14

    The identification of Pim-1/2 kinase overexpression in B-cell malignancies suggests that Pim kinase inhibitors will have utility in the treatment of lymphoma, leukemia, and multiple myeloma. Starting from a moderately potent quinoxaline-dihydropyrrolopiperidinone lead, we recognized the potential for macrocyclization and developed a series of 13-membered macrocycles. The structure-activity relationships of the macrocyclic linker were systematically explored, leading to the identification of 9c as a potent, subnanomolar inhibitor of Pim-1 and -2. This molecule also potently inhibited Pim kinase activity in KMS-12-BM, a multiple myeloma cell line with relatively high endogenous levels of Pim-1/2, both in vitro (pBAD IC50 = 25 nM) and in vivo (pBAD EC50 = 30 nM, unbound), and a 100 mg/kg daily dose was found to completely arrest the growth of KMS-12-BM xenografts in mice. PMID:27096050

  2. Design, synthesis, and biological evaluation of 3-vinyl-quinoxalin-2(1H)-one derivatives as novel antitumor inhibitors of FGFR1.

    PubMed

    Liu, Zhiguo; Yu, Shufang; Chen, Di; Shen, Guoliang; Wang, Yu; Hou, Leping; Lin, Dan; Zhang, Jinsan; Ye, Faqing

    2016-01-01

    FGFR1 is well known as a molecular target in anticancer drug design. TKI258 plays an important role in RTK inhibitors. Utilizing TKI258 as a lead compound that contains a quinazolinone nucleus, we synthesized four series of 3-vinyl-quinoxalin-2(1H)-one derivatives, a total of 27 compounds. We further evaluated these compounds for FGFR1 inhibition ability as well as cytotoxicity against four cancer cell lines (H460, B16-F10, Hela229, and Hct116) in vitro. Some compounds displayed good-to-excellent potency against the four tested cancer cell lines compared with TKI258. Structure-activity relationship analyses indicated that small substituents at the side chain of the 3-vinyl-quinoxalin-2(1H)-one were more effective than large substituents. Lastly, we used molecular docking to obtain further insight into the interactions between the compounds and FGFR1. PMID:27217720

  3. Synthesis, 3D-QSAR analysis and biological evaluation of quinoxaline 1,4-di-N-oxide derivatives as antituberculosis agents.

    PubMed

    Pan, Yuanhu; Li, Panpan; Xie, Shuyu; Tao, Yanfei; Chen, Dongmei; Dai, Menghong; Hao, Haihong; Huang, Lingli; Wang, Yulian; Wang, Liye; Liu, Zhenli; Yuan, Zonghui

    2016-08-15

    A series of quinoxaline 1,4-di-N-oxide derivatives variously substituted at C-2 position were synthesized and evaluated for in vitro antimycobacterial activity. Seventeen compounds exhibited potential activity (MIC ⩽6.25μg/mL) against Mycobacterium tuberculosis (H37Rv), in particular the compounds 3d and 3j having an MIC value of 0.39μg/mL. None of the compounds exhibited cytotoxicity when using an MTT assay in VERO cells. To further investigate the structure-activity relationship, CoMFA (q(2)=0.507, r(2)=0.923) and CoMSIA (q(2)=0.665, r(2)=0.977) models were performed on the basis of antimycobacterial activity data. The 3D-QSAR study of these compounds can provide useful information for further rational design of novel quinoxaline 1,4-di-N-oxides for treatment of tuberculosis. PMID:27426298

  4. Design, synthesis, and biological evaluation of 3-vinyl-quinoxalin-2(1H)-one derivatives as novel antitumor inhibitors of FGFR1

    PubMed Central

    Liu, Zhiguo; Yu, Shufang; Chen, Di; Shen, Guoliang; Wang, Yu; Hou, Leping; Lin, Dan; Zhang, Jinsan; Ye, Faqing

    2016-01-01

    FGFR1 is well known as a molecular target in anticancer drug design. TKI258 plays an important role in RTK inhibitors. Utilizing TKI258 as a lead compound that contains a quinazolinone nucleus, we synthesized four series of 3-vinyl-quinoxalin-2(1H)-one derivatives, a total of 27 compounds. We further evaluated these compounds for FGFR1 inhibition ability as well as cytotoxicity against four cancer cell lines (H460, B16-F10, Hela229, and Hct116) in vitro. Some compounds displayed good-to-excellent potency against the four tested cancer cell lines compared with TKI258. Structure–activity relationship analyses indicated that small substituents at the side chain of the 3-vinyl-quinoxalin-2(1H)-one were more effective than large substituents. Lastly, we used molecular docking to obtain further insight into the interactions between the compounds and FGFR1. PMID:27217720

  5. Crystal structure of 1,3-bis­(2,3-di­methyl­quinoxalin-6-yl)benzene

    PubMed Central

    Diesendruck, Charles E.; Rubin, Gabrielle; Bertke, Jeffery A.; Gray, Danielle L.; Moore, Jeffrey S.

    2015-01-01

    The title compound, C26H22N4 (I), was synthesized by C—H iridium-catalyzed borylation followed by Suzuki coupling. The mol­ecular structure of (I) consists of a central benzene ring with 3-di­methyl­quinoxalin-6-yl groups at the 1 and 3 positions. These 2,3-di­methyl­quinoxalin-6-yl groups twist significantly out of the plane of the benzene ring. There are inter­molecular π–π inter­actions which result in a two-dimensional extended structure. The layers extend parallel to the ab plane and stack along the c axis. PMID:26870397

  6. Single-layer electroluminescent devices based on fluorene-1H-pyrazolo[3,4-b]quinoxaline co-polymers

    NASA Astrophysics Data System (ADS)

    Pokladko-Kowar, Monika; Danel, Andrzej; Chacaga, Łukasz

    2013-11-01

    A fluorene based copolymer was synthesized for electroluminescent application. To the main chain of polymer the nitrogen heterocyclic, 1H-pyrazolo[3,4-b]quinoxaline, unit was introduced. The incorporation of this derivative tuned the emission from the blue to yellow-green one. A simple, single layered device was fabricated with the configuration ITO/PEDOT/co-poly-FLU-PQX/Ca/Mg.

  7. Cytochrome P450-Mediated Metabolism and DNA Binding of 2-Amino-1,7-dimethylimidazo[4,5-g]quinoxaline and its Carcinogenic Isomer 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline in Mice

    PubMed Central

    Turesky, Robert J.; Bessette, Erin E.; Dunbar, Deborah; Liberman, Rosa G.; Skipper, Paul L.

    2012-01-01

    2-Amino-1,7-dimethylimidazo[4,5-g]quinoxaline (MeIgQx) is a recently discovered heterocyclic aromatic amine (HAA) that is formed during the cooking of meats. MeIgQx is an isomer of 2-amino-3,8-dimethylmidazo[4,5-f]quinoxaline (MeIQx), a rodent carcinogen and possible human carcinogen that also occurs in cooked meats. MeIgQx is a bacterial mutagen but knowledge about its metabolism and carcinogenic potential is lacking. Metabolism studies on MeIgQx and MeIQx were conducted with human and mouse liver microsomes, and recombinant human P450s. DNA binding studies were also investigated in mice to ascertain the genotoxic potential of MeIgQx in comparison to MeIQx. Both HAAs underwent comparable rates of N-oxidation to form genotoxic N-hydroxylated metabolites with mouse liver microsomes (0.2 - 0.3 nmol/min/mg protein). The rate of N-oxidation of MeIQx was 4-fold greater than the rate of N-oxidation of MeIgQx with human liver microsomes (1.7 vs 0.4 nmol/min/mg protein). The rate of N-oxidation, by recombinant human P450 1A2, was comparable for both substrates (6 pmol/min/pmol P450 1A2). MeIgQx also underwent N-oxidation by human P450s 1A1 and 1B1 at appreciable rates, whereas MeIQx was poorly metabolized by these P450s. The potential of MeIgQx and MeIQx to form DNA adducts was assessed in female C57BL/6 mice given [14C]-MeIgQx (10 μCi, 9.68 mg/kg body wt) or [14C]-MeIQx (10 μCi, 2.13 mg/kg body wt). DNA adduct formation in liver, pancreas and colorectum was measured by accelerator mass spectrometry at 4, 24 or 48 h post-treatment. Variable levels of adducts were detected in all organs. The adduct levels were similar for both HAAs, when adjusted for dose, and ranged from 1 to 600 adducts per 107 nucleotides per mg/kg dose. Thus, MeIgQx undergoes metabolic activation and binds to DNA at levels that are comparable to MeIQx. Given the high amounts of MeIgQx formed in cooked meats, further investigations are warranted to assess the carcinogenic potential of this HAA. PMID

  8. 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. PMID:22339468

  9. New Phenyl Propanoids from Cryptocarya bracteolata.

    PubMed

    Saidi, Nurdin; Morita, Hiroshi; Litaudon, Marc; Nafiah, Mohd Azlan; Awang, Khalijah; Mustanir

    2016-06-01

    Two new phenyl propanoids were extracted from the bark of Cryptocarya bracteolate Gamb., ethyl 3-(2'-hydroxy-3',4',5'-trimethoxyphenyl) propanoate (1) and ethyl 3-(2'-glucosyl-3',4',5'-trimethoxyphenyl)propanoate (2), together with seven known alkaloids, (+)-lirioferine (3), (+)-bracteoline (4), (+)-reticuline (5), (+)-reticulineN-oxide (6), (-)-norargemonine (7), (+)-bisnorargemonine (8) and atherolin (9). The structures of compounds were established through several spectroscopic methods; 1D and 2D-NMR, UV, IR and MS. PMID:27534124

  10. Synthesis, characterization, electrochemical and biological studies on some metal(II) Schiff base complexes containing quinoxaline moiety

    NASA Astrophysics Data System (ADS)

    Justin Dhanaraj, Chellaian; Johnson, Jijo

    2014-01-01

    Novel Co(II), Ni(II), Cu(II) and Zn(II) complexes of Schiff base derived from quinoxaline-2,3-(1,4H)-dione and 4-aminoantipyrine (QDAAP) were synthesized. The ligand and its complexes were characterized by elemental analyses, molar conductance, magnetic susceptibility measurements, FTIR, UV-Vis., mass and 1H NMR spectral studies. The X band ESR spectrum of the Cu(II) complex at 300 and 77 K were also recorded. Thermal studies of the ligand and its complexes show the presence of coordinated water in the Ni(II) and Zn(II) complexes. The coordination behavior of QDAAP is also discussed. All the complexes are mono nuclear and tetrahedral geometry was found for Co(II) complex. For the Ni(II) and Zn(II) complexes, octahedral geometry was assigned and for the Cu(II) complex, square planar geometry has been suggested. The grain size of the complexes was estimated using powder XRD. The surface morphology of the compounds was studied using SEM analysis. Electrochemical behavior of the synthesized complexes in DMF at room temperature was investigated by cyclic voltammetry. The in vitro biological screening of QDAAP and its metal complexes were tested against bacterial species Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. The fungal species include Aspergillus niger, Aspergillus flavus and Candida albicans. The DNA cleavage activity of QDAAP and its complexes were also discussed.

  11. Spectral characterization, electrochemical and anticancer studies on some metal(II) complexes containing tridentate quinoxaline Schiff base

    NASA Astrophysics Data System (ADS)

    Chellaian, Justin Dhanaraj; Johnson, Jijo

    2014-06-01

    Co(II), Ni(II), Cu(II) and Zn(II) complexes of a tridentate ONO donor Schiff base ligand derived from 3-(2-aminoethylamino)quinoxalin-2(1H)-one were synthesized. The ligand and its metal complexes were characterized using elemental analysis, molar conductance, IR, 1H NMR, mass, magnetic susceptibility, electronic spectra and ESR spectral studies. Electrochemical behavior of the synthesized compounds was studied using cyclic voltammetry. The grain size of the synthesized compounds was determined by powder XRD. The Schiff base and its complexes have been screened for their antimicrobial activities against the bacterial species E. coli, K. pneumoniae, P. aeruginosa and S. aureus; fungal species include, A. niger, and C. albicans by disc diffusion method. The results show that the complexes have higher activity than the free ligand. The interaction of the complexes with calf thymus DNA (CT DNA) has been investigated by electronic absorption method. Furthermore, the DNA cleavage activity of the complexes was studied using agarose gel electrophoresis. In vitro anticancer studies of the ligand and its complexes using MTT assay was also done.

  12. Assembly of Cu/Ag-quinoxaline-polyoxotungstate hybrids: Influence of Keggin and Wells-Dawson polyanions on the structure

    NASA Astrophysics Data System (ADS)

    Chi, Ying-Nan; Cui, Feng-Yun; Lin, Zheng-Guo; Xu, Yan; Ma, Xiao-Yu; Shen, Pan-Pan; Huang, Kun-Lin; Hu, Chang-Wen

    2013-03-01

    In order to investigate the influence of Keggin and Wells-Dawson polyoxometalates on the resultant structure, four new organic-inorganic hybrid compounds [Cu4(qx)5(SiW12O40)] (1), [Cu6(qx)6(P2W18O62)(H2O)1.5]·4.5H2O (2), [Ag4(qx)4(SiW12O40)(H2O)]·H2O (3), [Ag6(qx)6(P2W18O62)]·8H2O (4) (qx=quinoxaline) were synthesized and structurally characterized by single-crystal X-ray diffraction. In 1, the 2D layers are linked by the SiW12O404- (SiW12) anions to construct a 3D framework. When the Wells-Dawson type P2W18O626- (P2W18) is used, 2 is prepared, in which the 1D helical chains are connected by P2W18 to form a 3D network. In 3, two kinds of 1D metal-organic chains are connected by SiW12 clusters to construct a 3D framework. In 4, there are also two kinds of 1D chains one kind of 1D chain combines with P2W18 by the AgO weak interaction and the other kind is just metal-organic chain. In addition, the electrochemistry properties of compounds 1-4 have been studied.

  13. Systematic and Molecular Basis of the Antibacterial Action of Quinoxaline 1,4-Di-N-Oxides against Escherichia coli

    PubMed Central

    Cheng, Guyue; Li, Bei; Wang, Chenxi; Zhang, Hongfei; Liang, Guixia; Weng, Zhifei; Hao, Haihong; Wang, Xu; Liu, Zhenli; Dai, Menghong; Wang, Yulian; Yuan, Zonghui

    2015-01-01

    Quinoxaline 1,4-di-N-oxides (QdNOs) are widely known as potent antibacterial agents, but their antibacterial mechanisms are incompletely understood. In this study, the transcriptomic and proteomic profiles of Escherichia coli exposed to QdNOs were integratively investigated, and the results demonstrated that QdNOs mainly induced an SOS response and oxidative stress. Moreover, genes and proteins involved in the bacterial metabolism, cellular structure maintenance, resistance and virulence were also found to be changed, conferring bacterial survival strategies. Biochemical assays showed that reactive oxygen species were induced in the QdNO-treated bacteria and that free radical scavengers attenuated the antibacterial action of QdNOs and DNA damage, suggesting an oxidative-DNA-damage action of QdNOs. The QdNO radical intermediates, likely carbon-centered and aryl-type radicals, as identified by electron paramagnetic resonance, were the major radicals induced by QdNOs, and xanthine oxidase was one of the QdNO-activating enzymes. This study provides new insights into the action of QdNOs in a systematic manner and increases the current knowledge of bacterial physiology under antibiotic stresses, which may be of great value in the development of new antibiotic-potentiating strategies. PMID:26296207

  14. N,N′-Bis(pyridin-2-yl)benzene-1,4-diamine–quinoxaline (2/1)

    PubMed Central

    Wicher, Barbara; Gdaniec, Maria

    2011-01-01

    The asymmetric unit of the title compound, 2C16H14N4·C8H6N2, consits of one mol­ecule of N,N′-bis­(pyridin-2-yl)benzene-1,4-diamine (PDAB) and one half-mol­ecule of quinoxaline (QX) that is located around an inversion centre and disordered over two overlapping positions. The PDAB mol­ecule adopts a non-planar conformation with an E configuration at the two partially double exo C N bonds of the 2-pyridyl­amine units. In the crystal, these self-complementary units are N—H⋯N hydrogen bonded via a cyclic R 2 2(8) motif, creating tapes of PDAB mol­ecules extending along [010]. Inversion-related tapes are arranged into pairs through π–π stacking inter­actions between the benzene rings [centroid–centroid distance = 3.818 (1) Å] and the two symmetry-independent pyridine groups [centroid–centroid distance = 3.760 (1) Å]. The QX mol­ecules are enclosed in a cavity formed between six PDAB tapes. PMID:22199763

  15. 40 CFR 721.8780 - Substituted pyridine azo substituted phenyl.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Substituted pyridine azo substituted... Specific Chemical Substances § 721.8780 Substituted pyridine azo substituted phenyl. (a) Chemical substance... substituted pyridine azo substituted phenyl (PMNs P-96-767 and P-96-773) are subject to reporting under...

  16. 40 CFR 721.8780 - Substituted pyridine azo substituted phenyl.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted pyridine azo substituted... Specific Chemical Substances § 721.8780 Substituted pyridine azo substituted phenyl. (a) Chemical substance... substituted pyridine azo substituted phenyl (PMNs P-96-767 and P-96-773) are subject to reporting under...

  17. 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...

  18. 40 CFR 721.536 - Halogenated phenyl alkane.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical 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. 27 CFR 21.121 - Phenyl mercuric benzoate.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2014-04-01 2014-04-01 false Phenyl mercuric benzoate. 21.121 Section 21.121 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY ALCOHOL FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants § 21.121 Phenyl mercuric benzoate....

  20. 27 CFR 21.121 - Phenyl mercuric benzoate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2011-04-01 2011-04-01 false Phenyl mercuric benzoate. 21.121 Section 21.121 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants § 21.121 Phenyl mercuric benzoate....

  1. 40 CFR 721.8780 - Substituted pyridine azo substituted phenyl.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted pyridine azo substituted... Specific Chemical Substances § 721.8780 Substituted pyridine azo substituted phenyl. (a) Chemical substance... substituted pyridine azo substituted phenyl (PMNs P-96-767 and P-96-773) are subject to reporting under...

  2. 40 CFR 721.8780 - Substituted pyridine azo substituted phenyl.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted pyridine azo substituted... Specific Chemical Substances § 721.8780 Substituted pyridine azo substituted phenyl. (a) Chemical substance... substituted pyridine azo substituted phenyl (PMNs P-96-767 and P-96-773) are subject to reporting under...

  3. 40 CFR 721.8780 - Substituted pyridine azo substituted phenyl.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted pyridine azo substituted... Specific Chemical Substances § 721.8780 Substituted pyridine azo substituted phenyl. (a) Chemical substance... substituted pyridine azo substituted phenyl (PMNs P-96-767 and P-96-773) are subject to reporting under...

  4. Binding mode of an α-amino acid-linked quinoxaline-2,3-dione analogue at glutamate receptor subtype GluK1.

    PubMed

    Demmer, Charles S; Møller, Charlotte; Brown, Patricia M G E; Han, Liwei; Pickering, Darryl S; Nielsen, Birgitte; Bowie, Derek; Frydenvang, Karla; Kastrup, Jette S; Bunch, Lennart

    2015-06-17

    Two α-amino acid-functionalized quinoxalines, 1a (CNG-10301) and 1b (CNG-10300), of a quinoxaline moiety coupled to an amino acid moiety were designed, synthesized, and characterized pharmacologically. While 1a displayed low affinity at native AMPA, KA, and NMDA receptors, and at homomeric GluK1,3 receptors, the affinity for GluK2 was in the midmicromolar range (Ki = 136 μM), 1b displayed low to midmicromolar range binding affinity at all the iGluRs (Ki = 9-126 μM). In functional experiments (outside-out patches excised from transfected HEK293T cells), 100 μM 1a partially blocked GluK1 (33% peak response), while GluK2 was unaffected (96% peak response). Furthermore, 1a was shown not to be an agonist at GluK1 and GluK2 at 100 μM. On the other hand, 100 μM 1b fully antagonized GluK1 (8% peak response) but only partially blocked GluK2 (33% peak response). An X-ray structure at 2.3 Å resolution of 1b in the GluK1-LBD (ligand-binding domain) disclosed an unexpected binding mode compared to the predictions made during the design phase; the quinoxaline moiety remains to act as an amino acid bioisostere, but the amino acid moiety is oriented into a new area within the GluK1 receptor. The structure of the GluK1-LBD with 1b showed a large variation in domain openings of the three molecules from 25° to 49°, demonstrating that the GluK1-LBD is capable of undergoing major domain movements. PMID:25856736

  5. New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents.

    PubMed

    Torres, Enrique; Moreno, Elsa; Ancizu, Saioa; Barea, Carlos; Galiano, Silvia; Aldana, Ignacio; Monge, Antonio; Pérez-Silanes, Silvia

    2011-06-15

    The increase in the prevalence of drug-resistant tuberculosis cases demonstrates the need of discovering new and promising compounds with antimycobacterial activity. As a continuation of our research and with the aim of identifying new antitubercular drugs candidates, a new series of quinoxaline 1,4-di-N-oxide derivatives containing isoniazid was synthesized and evaluated for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Moreover, various drug-like properties of new compounds were predicted. Taking into account the biological results and the promising drug-likeness profile of these compounds, make them valid leads for further experimental research. PMID:21570839

  6. Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions.

    PubMed

    Nagarajaiah, Honnappa; Mishra, Abhaya Kumar; Moorthy, Jarugu Narasimha

    2016-04-26

    α-Chloroketones - obtained by the atom-economical chlorination of ketones with trichloroisocyanuric acid (TCCA) in the presence of p-TSA under ball-milling conditions - were set up for a sequential base-mediated condensation reaction with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde to afford 2-aminothiazoles, 2-hydrazinylthiazoles, quinoxalines and benzoylbenzofurans, respectively, in respectable yields. The viability of one-pot sequential acid- and base-mediated reactions in the solid state under ball-milling conditions is thus demonstrated. PMID:27072599

  7. Hypervalent iodine(iii)-promoted N-incorporation into N-aryl vinylogous carbamates to quinoxaline diesters: access to 1,4,5,8-tetraazaphenanthrene.

    PubMed

    Sagar, A; Vidaycharan, Shinde; Shinde, Anand H; Sharada, Duddu S

    2016-04-26

    A novel oxidative N-incorporation strategy for synthesis of quinoxaline diesters under metal-free conditions is described for the first time. The mild reaction conditions allow for this transformation via the formation of two C(sp(2))-N bonds utilizing cheaply available NaN3 as the N-atom source. N-Aryl vinylogous carbamates in this study undergo azidation at enamino C(sp(2))-H selectively. The robustness of this strategy is further demonstrated by the synthesis of a valuable 1,4,5,8-tetraazaphenanthrene derivative using a mild and convenient approach. PMID:27050385

  8. A Ferrocene-Quinoxaline Derivative as a Highly Selective Probe for Colorimetric and Redox Sensing of Toxic Mercury(II) Cations

    PubMed Central

    Zapata, Fabiola; Caballero, Antonio; Molina, Pedro; Tarraga, Alberto

    2010-01-01

    A new chemosensor molecule 3 based on a ferrocene-quinoxaline dyad recognizes mercury (II) cations in acetonitrile solution. Upon recognition, an anodic shift of the ferrocene/ferrocenium oxidation peaks and a progressive red-shift (Δλ = 140 nm) of the low-energy band, are observed in its absorption spectrum. This change in the absorption spectrum is accompanied by a colour change from orange to deep green, which can be used for a “naked-eye” detection of this metal cation. PMID:22163528

  9. Studies on some metal complexes of quinoxaline based unsymmetric ligand: Synthesis, spectral characterization, in vitro biological and molecular modeling studies.

    PubMed

    Dhanaraj, Chellaian Justin; Johnson, Jijo

    2016-08-01

    Mononuclear Co(II), Ni(II), Cu(II) and Zn(II) complexes of an unsymmetric Schiff base ligand, 3-(-(3-(-3,5-dichloro-2-hydroxybenzylideneamino)propylimino)methyl)quinoxalin-2(1H) -one (L) were synthesized and characterized by various analytical and spectral techniques. The molar conductance values of metal complexes indicate non-electrolytic behavior of the metal complexes. The Schiff base act as tetra dentate ONNO donor ligand in Co(II), Ni(II), Zn(II) complexes and tridentate NNO donor in Cu(II) complex. Thermal stabilities of the newly synthesized compounds were determined by thermal analysis. Crystallinity, average grain size and unit cell parameters were determined from powder X-ray diffraction study. Electrochemical behaviors of the compounds were examined by cyclic voltammetry technique. The Schiff base and its complexes have been screened for their in vitro antimicrobial activities against some bacterial and fungal strains by disc diffusion method. The interaction of the compounds with calf thymus DNA (CT DNA) has been investigated by electronic absorption spectral titration and viscosity measurement (hydrodynamic) methods. Furthermore, the pUC18 DNA cleavage activities of the complexes have been explored. The compounds were also subjected to in vitro antioxidant, anticancer activity screening, druglikeness and bioactivity predictions using Molinspiration software. Molecular docking studies of the present compounds were carried out against B-DNA dodecamer d(CGCGAATTCGCG)2 and vascular endothelial growth factor receptor (VEGFR-2) kinase. Quantum chemical calculations were done with DFT method to determine the optimum geometry of the ligand and its metal complexes. From the quantum chemical parameters, the reactivity parameters of the compounds were established. PMID:27236046

  10. Assessing the reactivity of sodium alkyl-magnesiates towards quinoxaline: single electron transfer (SET) vs. nucleophilic alkylation processes.

    PubMed

    Livingstone, Zoe; Hernán-Gómez, Alberto; Baillie, Sharon E; Armstrong, David R; Carrella, Luca M; Clegg, William; Harrington, Ross W; Kennedy, Alan R; Rentschler, Eva; Hevia, Eva

    2016-04-14

    By exploring the reactivity of sodium butyl-magnesiate (1) supported by the bulky chelating silyl(bisamido) ligand {Ph2Si(NAr*)2}(2-) (Ar* = 2,6-iPr2-C6H3) towards Quinoxaline (Qx), the ability of this bimetallic system to effectively promote SET processes has been disclosed. Thus 1 executes the single-electron reduction of Qx affording complex (2) whose structure in the solid state contains two quinaxolyl radical anions Qx˙ stabilised within a dimeric magnesiate framework. Combining multinuclear NMR and EPR measurements with DFT calculations, new insights into the constitution of 2 in solution and its magnetic behaviour have been gained. Further evidence on the SET reactivity of 1 was found when it was reacted with nitroxyl radical TEMPO which furnished contacted ion pair sodium magnesiate [(Ph2Si(NAr*)2)Mg(TEMPO(-))Na(THF)3] (4) where both metals are connected by an alkoxide bridge, resulting from reduction of TEMPO. The role that the different ligands present in 1 can play in these new SET reactions has also been assessed. Using an amination approach, the Bu group in 1 can be replaced by the more basic amide TMP allowing the isolation of (3) which was characterised by multinuclear NMR and X-ray crystallography. (1)H NMR monitoring of the reaction of 3 with Qx showed its conversion to 2, leaving the hydrogen atoms of the heterocycle untouched. Contrastingly, using sodium homoalkyl magnesiate [NaMg(CH2SiMe3)3] (5) led to the chemoselective C2 alkylation of this heterocycle, suggesting that the presence of the steric stabiliser {Ph2Si(NAr*)2}(2-) on the mixed-metal reagent is required in order to facilitate the Qx reduction. PMID:26617325

  11. Essential oil phenyl propanoids. Useful as .OH scavengers?

    PubMed

    Taira, J; Ikemoto, T; Yoneya, T; Hagi, A; Murakami, A; Makino, K

    1992-01-01

    In order to search for radical scavengers which could be used as raw materials for cosmetics, phenyl propanoids (eugenol, isoeugenol, dehydrodieugenol, dehydrodieugenol B and coniferyl aldehyde) were examined for their hydroxyl radical (.OH) scavenging ability. A Fenton system was used to produce .OH. In order to see scavenging by these phenyl propanoids, competition reactions between a spin trap, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO), and these phenyl propanoids for .OH were studied. The relative yield of the spin adduct of .OH (DMPO-OH) was measured by electron spin resonance spectroscopy. The approximate rate constants of the reactions between these phenyl propanoids and .OH estimated by measuring the reduced height of the ESR signals of DMPO-OH were found to be at least in the order of 10(9) M-1 s-1 (diffusion-controlled). Also, using the TBA tests, the reactions between .OH and several compounds reactive with .OH were investigated in the presence of the phenyl propanoids and it was found that the phenyl propanoids compete with such reactive compounds for .OH. These results indicate that these phenyl propanoids can be used as antioxidants for skin damage perhaps caused by .OH generated by UV-light. PMID:1318253

  12. 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate

    PubMed Central

    Fun, Hoong-Kun; Kia, Reza; Raithby, Paul R.

    2008-01-01

    The title compound, C27H18N4O·2CH4O, is a unsymmetrically substituted quinoxaline. An intra­molecular O—H⋯N hydrogen bond involving the hydr­oxy and imino groups generates an S(6) ring motif. Inter­molecular C—H⋯O and N—H⋯O hydrogen bonds form an R 2 1(7) ring motif involving a methanol O atom and two H atoms of the imidazole and benzene rings, respectively. The latter links neighbouring mol­ecules into one-dimensional extended chains along the a axis. The two benzene rings are inclined towards each other, as indicated by the dihedral angle of 52.13 (10)°. The phenol ring is almost coplanar with the basic quinoxaline unit, making a dihedral angle of 2.43 (6)°. The short distances between the centroids of the five- and six-membered rings prove the existence of π–π inter­actions [centroid–centroid distances = 3.5234 (9)–3.7885 (10) Å]. The crystal structure is stabilized by intra­molecular O—H⋯N, inter­molecular O—H⋯O, N—H⋯O and C—H⋯O (× 2) hydrogen bonds and weak inter­molecular C—H⋯π and π–π inter­actions. PMID:21201724

  13. Iron-Catalyzed Intramolecular C(sp(2))-N Cyclization of 1-(N-Arylpyrrol-2-yl)ethanone O-Acetyl Oximes toward Pyrrolo[1,2-a]quinoxaline Derivatives.

    PubMed

    Zhang, Zhiguo; Li, Junlong; Zhang, Guisheng; Ma, Nana; Liu, Qingfeng; Liu, Tongxin

    2015-07-01

    An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N-O bond cleavage and intramolecular directed C-H arylation reactions in acetic acid. PMID:26057737

  14. Synthesis of 1,3,4-thiadiazole, 1,3,4-thiadiazine, 1,3,6-thiadiazepane and quinoxaline derivatives from symmetrical dithiobiureas and thioureidoethylthiourea derivatives.

    PubMed

    Hassan, Alaa A; Mourad, Aboul-Fetouh; El-Shaieb, Kamal M; Abou-Zied, Ashraf H

    2005-01-01

    Reactions of N,N;-disubstituted hydrazinecarbothioamides 8a-c and substituted thioureidoethylthioureas 9a-c with 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil, 10a) and 2,3,5,6-tetrabromo-1,4-benzoquinone (bromanil, 10b) to form N,N;-disubstituted [1,3,4]thiadiazole-2,5-diamines 11a-c, 6,7-dichloro-3-substituted amino-1H-benzo[1,3,4]- thiadiazine-5,8-diones 12a-c, 2,3,7,8-tetrahalothianthrene-1,4,6,9-tetraones 13a,b, 5,6,8- trihalo-7-oxo-3,7-dihydro-2H-quinoxaline-1-carbothioic acid substituted amides 14a-c, 15a-c and 7-substituted imino-[1,3,6]thiadiazepane-3-thiones 16a-c are reported. Rationales for the observed conversions are presented. PMID:18007352

  15. Organic Photosensitizers Incorporating Rigidified Dithieno[3,2-f:2',3'-h]quinoxaline Segment Tethered with Thiophene Substitutes for Dye-Sensitized Solar Cells.

    PubMed

    Ni, Jen-Shyang; Chiu, Tang-Yao; Kao, Wei-Siang; Chou, Hao-Ju; Su, Chao-Chin; Lin, Jiann T

    2016-09-01

    Metal-free D-π-RS-π-A type sensitizers, consisting of triphenylamine as the electron donor, 2,3-bis(3-(2-ethylhexyl)-5-methylthiophen-2-yl)dithieno[3,2-f:2',3'-h]quinoxaline (DTQT) as the rigidified conjugation spacer (RS), thiophene as the π-spacer, and 2-cyanoacrylic acid as the acceptor/anchor, have broad absorption spectra ranging from 350 to 550 nm and a high molar extinction coefficient up to >46 200 M(-1) cm(-1). Under simulated AM 1.5 G illumination, the dye-sensitized solar cells (DSSCs) fabricated from the dyes exhibited light-to-electricity conversions in the range of 6.78% to 8.27%. The best efficiency is slightly higher than that of N719-based standard DSSC (7.92%). The efficiency can be further boosted to 8.51% by optimizing the concentration of LiI electrolyte. PMID:27523392

  16. Dipolar Dyes with a Pyrrolo[2,3-b]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging.

    PubMed

    Łukasiewicz, Łukasz G; Deperasińska, Irena; Poronik, Yevgen M; Jun, Yong Woong; Banasiewicz, Marzena; Kozankiewicz, Bolesław; Ahn, Kyo Han; Gryko, Daniel T

    2016-06-01

    Two strongly polarized dipolar chromophores possessing a cyclic tertiary amino group at one terminus of the molecule and a CN group at the opposite terminus were designed and synthesized. Their rigid skeleton contains the rarely studied pyrrolo[2,3-b]quinoxaline ring system. The photophysical properties of these regioisomeric dyes were different owing to differing π conjugation between the CN group and the electron-donor moiety. These dipolar molecules showed very intense emission, strong solvatofluorochromism, and sufficient two-photon brightness for bioimaging. One of these regioisomeric dyes, namely, 11-carbonitrile-2,3,4,5,6,7-hexahydro-1H-3a,8,13,13b-tetraazabenzo[b]cyclohepta[1,2,3-jk]fluorene, was successfully utilized in two-photon imaging of mouse organ tissues and showed distinct tissue morphology with high resolution. PMID:27027726

  17. Syntheses, structural, theoretical studies and thermal behaviors of two luminous copper(I) halide complexes of dipyrido[3,2-f:2,3-h]-quinoxaline

    NASA Astrophysics Data System (ADS)

    Chen, Aihua; Meng, Suci; Zhang, Jinfang; Zhang, Chi

    2013-10-01

    Two new copper(I) complexes containing PPh3 and Dpq, [Cu(Dpq)(PPh3)X] (X = I (1); Br (2)), {PPh3 = triphenylphosphine, Dpq = dipyrido[3,2-f:2,3-h]-quinoxaline} have been synthesized and characterized by elemental analysis, IR spectroscopy, X-ray single crystal analysis, fluorescent analysis, thermal gravimetric analysis and DFT calculations. Single crystal X-ray diffraction analysis reveals that complexes 1 and 2 are mononuclear with similar structures and display a favorable pairwise π-π stacking. Density functional theory and time-dependent density functional theory calculations at the B3LYP/LanL2DZf+6-31G∗ level were performed on both complexes to rationalize their experimental absorption spectra. In addition, 1 and 2 exhibit intense luminescence in ethanol solution at room temperature.

  18. Phenyl radical thermolysis and rate constants for phenyl + O{sub 2}

    SciTech Connect

    Kumaran, S.S.; Michael, J.V.

    1997-08-01

    The thermal decomposition of C{sub 6}H{sub 5}I has been used to prepare in-situ known initial concentrations of phenyl radicals at high temperatures. These can be degraded by direct decomposition at T > 1350 K giving H + C{sub 6}H{sub 4}. Using H-atom ARAS, rate constants for C{sub 6}H{sub 5} dissociation have been measured. Using the same ARAS technique, constants for C{sub 6}H{sub 5} dissociation have been measured. Using the same ARAS technique, the H- and O-atoms formed from the reaction, C{sub 6}H{sub 5} + O{sub 2}, have both been measured. The rate constant results are discussed along with lower T measurements in terms of RRKM calculations using published ab initio electronic structure determinations of transition states.

  19. Revisiting the photodissociation dynamics of the phenyl radical

    SciTech Connect

    Cole-Filipiak, Neil C.; Shapero, Mark; Negru, Bogdan; Neumark, Daniel M.

    2014-09-14

    We have reinvestigated the photodissociation dynamics of the phenyl radical at 248 nm and 193 nm via photofragment translational spectroscopy under a variety of experimental conditions aimed at reducing the nascent internal energy of the phenyl radical and eliminating signal from contaminants. Under these optimized conditions, slower translational energy (P(E{sub T})) distributions for H-atom loss were seen at both wavelengths than in previously reported work. At 193 nm, the branching ratio for C{sub 2}H{sub 2} loss vs. H-atom loss was found to be 0.2 ± 0.1, a significantly lower value than was obtained previously in our laboratory. The new branching ratio agrees with calculated Rice-Ramsperger-Kassel-Marcus rate constants, suggesting that the photodissociation of the phenyl radical at 193 nm can be treated using statistical models. The effects of experimental conditions on the P(E{sub T}) distributions and product branching ratios are discussed.

  20. A study on the spectroscopy and photophysics of N-phenyl pyrrole and N-phenyl pyrazole

    NASA Astrophysics Data System (ADS)

    Sarkar, Aindrila; Chakravorti, Sankar

    1995-03-01

    Comprehensive spectroscopic and photophysical studies of N-phenyl pyrrole (PPr) and N-phenyl pyrazole (PPz) in different solvents show that a new emission band appears due to aggregation of PPr in water. The presence of β-cyclodextrin (β-CD) in aqueous solution of PPr causes deaggregation but the twisted intramolecular charge transfer emission ceases due to the cavity effect. In PPz, aggregation and TICT emission are absent. Protonation in PPz is restricted to a single site only at very high acid concentration. Both the molecules are planar in the ground state.

  1. 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...

  2. 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...

  3. 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...

  4. 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...

  5. Chemistry of the pyrazolidines. 26. Alkylation of 4-benzyliden-1-phenyl-3,5-dioxopyrazolidines

    SciTech Connect

    Moldarev, B.L.; Aronzon, M.E.; Adanin, V.M.; Zyakun, A.M.

    1986-08-01

    The reaction of 4-benzyliden-1-phenyl-3,5-dioxopyrazolidines with alkyl halides in the presence of sodium alkoxide gave 1-phenyl-2-alkyl-4-benzyliden- and 1-phenyl-2,4-dialkyl-4-(..cap alpha..-alkoxybenzyl)-3,4-dioxopyrazolines. The structures of these compounds were confirmed by UV, IR, and PMR spectroscopy, and by mass-spectrometry.

  6. 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...

  7. Amine-phenyl multi-component gradient stationary phases.

    PubMed

    Dewoolkar, Veeren C; Kannan, Balamurali; Ashraf, Kayesh M; Higgins, Daniel A; Collinson, Maryanne M

    2015-09-01

    Continuous multi-component gradients in amine and phenyl groups were fabricated using controlled rate infusion (CRI). Solutions prepared from either 3-aminopropyltriethoxysilane (APTEOS) or phenyltrimethoxysilane (PTMOS) were infused, in a sequential fashion, at a controlled rate into an empty graduated cylinder housing a vertically aligned thin layer chromatography (TLC) plate. The hydrolyzed precursors reacted with an abundance of silanol (SiOH) groups on the TLC plates, covalently attaching the functionalized silane to its surface. The extent of modification by phenyl and amine was determined by the kinetics of each reaction and the exposure time at each point along the TLC plate. The local concentrations of phenyl and amine were measured using diffuse reflectance spectroscopy and X-ray photoelectron spectroscopy, respectively. The profile of the multi-component gradients strongly depended on the order of infusion, the direction of the gradient and the presence of available surface silanol groups. A slightly higher amount of phenyl can be deposited on the TLC plate by first modifying its surface with amine groups as they serve as a catalyst, enhancing condensation. Separation of water- and fat-soluble vitamins and the control of retention factors were demonstrated on the multi-component gradient TLC plates. Uniformly modified and single-component TLC plates gave different separations compared to the multi-component gradient plates. The retention factors of the individual vitamins depended on the order of surface modification, the spotting end, and whether the multi-component gradients align or oppose each other. PMID:26255112

  8. Copper-catalyzed domino synthesis of 2-imino-1H-imidazol-5(2H)-ones and quinoxalines involving C-C bond cleavage with a 1,3-dicarbonyl unit as a leaving group.

    PubMed

    Yang, Yan; Ni, Fan; Shu, Wen-Ming; Wu, An-Xin

    2014-09-01

    Although 2-imino-1H-imidazol-5(2H)-ones have important biological activities in metabolism, their synthesis has rarely been investigated. Quinoxalines as "privileged scaffolds" in medicinal chemistry have been extensively investigated, but the development of novel and efficient synthetic methods remains very attractive. Herein, we have developed two copper-catalyzed domino reactions for the synthesis of 2-imino-1H-imidazol-5(2H)-ones and quinoxalines involving CC bond-cleavage with a 1,3-dicarbonyl unit as a leaving group. The domino sequence for the synthesis of 2-imino-1H-imidazol-5(2H)-ones includes aza-Michael addition, intramolecular cyclization, CC bond-cleavage, 1,2-rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza-Michael addition, intramolecular cyclization, elimination reaction, and CC bond-cleavage reaction. The two domino reactions have significant advantages including high efficiency, mild reaction conditions, and high tolerance of various functional groups. PMID:25079446

  9. Synthesis and evaluation of the cytotoxic activity of novel ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzyl-phenylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives in myeloid and lymphoid leukemia cell lines.

    PubMed

    Desplat, Vanessa; Vincenzi, Marian; Lucas, Romain; Moreau, Stéphane; Savrimoutou, Solène; Pinaud, Noël; Lesbordes, Jordi; Peyrilles, Elodie; Marchivie, Mathieu; Routier, Sylvain; Sonnet, Pascal; Rossi, Filomena; Ronga, Luisa; Guillon, Jean

    2016-05-01

    Leukemia is the most common blood cancer, and its development starts at diverse points, leading to distinct subtypes that respond differently to therapy. This heterogeneity is rarely taken into account in therapies, so it is still essential to look for new specific drugs for leukemia subtypes or even for therapy-resistant cases. Among heterocyclic compounds that attracted a lot of attention because of its wide spread biological activities, the pyrrolo[1,2-a]quinoxaline heterocyclic framework has been identified as interesting scaffolds for antiproliferative activity against various human cancer cell lines. In the present study, novel ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzyl-phenylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives 1a-l have been designed and synthesized. Their cytotoxicities were evaluated against five different leukemia cell lines, including Jurkat and U266 (lymphoid cell lines), and K562, U937, HL60 (myeloid cell lines), as well as normal human peripheral blood mononuclear cells (PBMNCs). Then, apoptosis study was performed with the more interesting compounds. The new pyrrolo[1,2-a]quinoxaline series showed promising cytotoxic potential against all leukemia cell lines tested, and some compounds showed better results than the reference compound A6730. Some compounds, such as 1a, 1e, 1g and 1h are promising because of their high activity against leukemia and their low activity against normal hematopoietic cells. Structure-activity relationships of these new synthetic compounds 1a-l are here also discussed. PMID:26945110

  10. 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.

  11. Disposition of the Dietary Mutagen 2-Amino-3,8-dimethylimidazo[4,5- f ]quinoxaline in Healthy and Pancreatic Cancer Compromised Humans

    DOE PAGESBeta

    Malfatti, Michael A.; Kuhn, Edward A.; Turteltaub, Kenneth W.; Vickers, Selwyn M.; Jensen, Eric H.; Strayer, Lori; Anderson, Kristin E.

    2016-02-26

    Pancreatic cancer is the fourth leading cause of cancer death in the U.S. Once diagnosed, prognosis is poor with a 5-year survival rate of less than 5%. Exposure to carcinogenic heterocyclic amines (HCAs) derived from cooked meat has been shown to be positively associated with pancreatic cancer risk. To evaluate the processes that determines the carcinogenic potential of HCAs for human pancreas, 14-carbon labeled 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), a putative human carcinogenic HCA found in well-done cooked meat, was administered at a dietary relevant dose to human volunteers diagnosed with pancreatic cancer undergoing partial pancreatectomy and healthy control volunteers. After 14C-MeIQx exposure,more » blood and urine was collected for pharmacokinetic and metabolite analysis. MeIQx-DNA adducts levels were quantified by accelerator mass spectrometry from pancreatic tissue excised during surgery from the cancer patient group. Pharmacokinetic analysis of plasma revealed a rapid distribution of MeIQx with a plasma elimination half-life of approximately 3.5 hr in 50% of the cancer patients and all of the control volunteers. In 2 of the 4 cancer patients very low levels of MeIQx were detected in plasma and urine suggesting low absorption from the gut into the plasma. Urinary metabolite analysis revealed five MeIQx metabolites with 2-amino-3-methylimidazo[4,5-f]quinoxaline-8-carboxylic acid being the most abundant accounting for 25%–50% of the recovered 14-carbon/ml urine. We found there was no discernable difference in metabolite levels between the cancer patient volunteers and the control group. MeIQx-DNA adduct analysis of pancreas and duodenum tissue revealed adduct levels indistinguishable from background levels. Lastly, although other meat-derived HCA mutagens have been shown to bind DNA in pancreatic tissue, indicating that exposure to HCAs from cooked meat cannot be discounted as a risk factor for pancreatic cancer, the results from this

  12. New osmium cluster compounds containing the heterocyclic ligand 2,3-bis-(diphenylphosphino)quinoxaline (dppq): Ligand isomerization and crystal structures of dppq, the isomeric clusters Os3(CO)10(dppq), and HOs3(CO)9[ -2,3-PhP(h1-C6H4)(Ph2P)quinoxaline

    SciTech Connect

    Hunt, Sean W; Yang, Li; Wang, Xiaoping; Richmond, Michael G.

    2011-01-01

    Treatment of the labile cluster 1,2-Os{sub 3}(CO){sub 10}(MeCN){sub 2} (1) with the diphosphine ligand 2,3-bis(diphenylphosphino)quinoxaline (dppq) at room temperature affords 1,2-Os{sub 3}(CO){sub 10}(dppq) (2b) as the kinetic product of ligand substitution in 84% yield. 2b isomerizes to the thermodynamically more stable dppq-chelated cluster 1,1-Os{sub 3}(CO){sub 10}(dppq) (2c) as the sole observable product under CO at temperatures below 358 K. The kinetics for the conversion of 2b {yields} 2c have been investigated by NMR spectroscopy in CDCl{sub 3} over the temperature range 323-353 K, and the reaction was found to exhibit a rate law that is first order in 2b. The calculated activation parameters [{Delta}H{sup {ne}} = 25.4(4) kcal/mol; {Delta}S{sup {ne}} = -3(1) eu] support an intramolecular isomerization scenario, one that involves the migration of phosphine and CO groups about the cluster polyhedron. The disposition of the dppq ligand in the isomeric Os{sub 3}(CO){sub 10}(dppq) clusters has been established by X-ray crystallography and {sup 31}P NMR spectroscopy. Photolysis of 2c at 366 nm leads to CO loss and ortho metalation of one of the aryl groups on the Ph{sub 2}P moiety to furnish the hydride cluster HOs{sub 3}(CO){sub 9}[{mu}-PhP({eta}{sup 1}-C{sub 6}H{sub 4})(Ph{sub 2}P)quinoxaline] (3). The isomerization behavior exhibited by 2b follows that of related diphosphine-substituted Os{sub 3} clusters prepared by us.

  13. Direct synthesis and characterization of phenyl-functionalized SBA-15

    NASA Astrophysics Data System (ADS)

    Wang, Xue-mei; Du, Xin-zhen; Li, Chun-lan; Cao, Xu

    2008-04-01

    Phenyl-functionalized SBA-15 materials (Ph-SBA-15) were directly synthesized by using tri-block copolymer Pluronic P123 as templating agent under acidic conditions. The samples were characterized by Fourier transform infrared (FT-IR) spectra, X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), thermogravimetry analysis (TGA) and N 2 adsorption-desorption. The results show that the phenyl groups are covalently attached to the pore wall of SBA-15 after modification. The functionalized materials still preserve a desirable two-dimensional P6 mm hexagonal structure and have large specific surface area and pore volume although the molar ratio of phenyltrimethoxysilane in total silica precursors is as high as 23.0%.

  14. Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles.

    PubMed

    Siddall, Thomas L; Ouse, David G; Benko, Zoltan L; Garvin, Gail M; Jackson, Johnny L; McQuiston, Jeffrey M; Ricks, Michael J; Thibault, Thomas D; Turner, James A; Vanheertum, John C; Weimer, Monte R

    2002-12-01

    A novel series of substituted 3-phenyl benzoylpyrazoles were prepared and tested as potential grass herbicides. The targeted materials were prepared by three newly developed synthetic routes, which allowed a comprehensive study of the SAR (structure-activity relationships) of this series. The best combination of grass weed activity (Avena fatua L, Setaria viridis (L) Beauv and Alopecurus myosuroides Huds) and wheat selectivity was obtained with an alkoxy group in the 4-position of the phenyl ring. Activity was further enhanced by the presence of tert-butyl on the pyrazole and a methyl group at the C-2 position of the benzoyl moiety. The alkoxy-substituted 3-phenylbenzoylpyrazoles are a novel class of herbicides with potential utility for control of important grass weeds in cereals. PMID:12476990

  15. Electrochemical reduction of phenyl(9-m-carboranyl)iodonium tetrafluoroborate

    SciTech Connect

    Groshin, V.V.; Butin, K.P.; Shcherbina, T.M.; Tolstnaya, T.P.

    1985-08-20

    This paper shows that the controlled-potential electrolysis (-0.4 V, s.c.e.) of phenyl(9-m-carboranyl)iodonium tetrafluoroborate (I) on a mercury cathode in a 0.05 M solution of Bu/sub 4/NBF/sup -//sub 4/ in DMF proceeds regiospecifically with breakage exclusively of the C-I bond in the cation of (I) to give 70% benzene (as indicated in gas-liquid chromatography) and 73% 9-iodo-m-carborane with a current yield of about 80%. These results support a previous hypothesis that all the reactions of phenyl(B-carboranyl)iodonium salts with nucleophiles, which accompany breakage of the C-I bond, proceed by the transfer of one electron from the nucleophile to the iodonium cation.

  16. 2-Phenyl­biguanidinium hydrogen succinate methanol monosolvate

    PubMed Central

    Matulková, Irena; Císařová, Ivana; Němec, Ivan

    2010-01-01

    In the crystal of the title compound, C8H12N5 +·C4H5O4 −·CH3OH, the hydrogen succinate anions form infinite [010] chains via short, almost symmetrical, O⋯H⋯O hydrogen bonds. The 2-phenyl­biguanidium cations inter­connect these chains into layers lying parallel to the bc plane by way of N—H⋯O links. These planes only weakly inter­act in the direction of the a axis via C—H⋯π contacts between offset phenyl rings, leaving as much as 17% of the unit-cell volume accessible for the solvent. However, the methanol solvent mol­ecules could not be resolved due to extensive disorder and their assumed presence was removed from the overall scattering by the PLATON SQUEEZE procedure. PMID:21589482

  17. Multiresidue HPLC methods for phenyl urea herbicides in water.

    PubMed

    Ruberu, S R; Draper, W M; Perera, S K

    2000-09-01

    High-performance liquid chromatography (HPLC) methods for the determination of phenyl urea herbicides in water are described. The target compounds include chlortoluron, diuron, fluometuron, isoproturon, linuron, metobromuron, metoxuron, monuron, neburon, and siduron. Water was subjected to solid phase extraction (SPE) using either automated SPE with 47 mm C(18) Empore disks or on-line precolumn concentration. Herbicides were separated on a C(18) reversed phase column with an acetonitile-water gradient and were detected with either a diode array detector (DAD) or a postcolumn photolysis and derivatization (PPD) detector system. Photolysis converted the phenyl ureas to monoalkylamines that were derivatized to fluorescent isoindoles by reaction with o-phthalaldehyde and 2-mercaptoethanol. The DAD monitoring at 245 nm was linear over three decades with instrument detection limits of approximately 0.01 mg/L. SPE efficiency was between 48 and 70% in laboratory reagent water, but use of the internal standard quantitation method improved accuracy. High total dissolved solids and total organic carbon values in surface water improved recoveries relative to laboratory reagent water for all of the phenyl ureas. In Colorado River water spiked at 1 or 50 microg/L, mean recoveries ranged from 74 to 104%. Method detection limits (MDLs) ranged from 4 to 40 ng/L (parts per trillion) with the DAD instrument. PPD detection was highly specific but resulted in a slight loss in chromatographic efficiency and average MDLs approximately 5 times higher using a single set of detection conditions. The study indicates that methods based on SPE followed by HPLC with diode array or PPD detection have practical utility for trace analysis of phenyl ureas in drinking water or surface waters. PMID:10995323

  18. Roles of ROS mediated oxidative stress and DNA damage in 3-methyl-2-quinoxalin benzenevinylketo-1, 4-dioxide-induced immunotoxicity of Sprague-Dawley rats.

    PubMed

    Gao, Hui; Wang, Di; Zhang, Shun; Xu, Mengjing; Yang, Wei; Yan, Peipei; Liu, Yang; Luo, Xiao; Wu, Hailei; Yao, Ping; Yan, Hong; Liu, Liegang

    2015-11-01

    3-methyl-2-quinoxalin benzenevinylketo-1, 4-dioxide (Quinocetone, QCT) has been broadly used to treat dysentery and promote animal growth in food producing animals. However, its potential toxicity could not been neglected as parts of safety assessment according to the acceptable guidelines for QCT administration. In this study, the immunotoxicity of QCT was investigated in male Sprague-Dawley (SD) rats following a 28-day oral exposure at doses of 0, 50, 800, and 2400 mg/kg/day. The food consumption, body weight gain and relative spleen weight were significantly decreased by QCT in a dose-dependent manner. Treatment of rats with QCT also notably suppressed the T-cell proliferation and natural killer (NK) cell activity, accompanied by intracellular reactive oxygen species (ROS) accumulation, antioxidant system inhibition and DNA damage enhancement. Thus, the primary finding of this study is that QCT exposure (2400 mg/kg/day) could cause immunotoxicity in SD rats due to ROS mediated oxidative stress and DNA damage. PMID:26361855

  19. Monoclonal antibody production and indirect competitive enzyme-linked immunosorbent assay development of 3-methyl-quinoxaline-2-carboxylic acid based on novel haptens.

    PubMed

    Li, Guopeng; Zhao, Liang; Zhou, Feng; Li, Jiaying; Xing, Yuan; Wang, Tiangang; Zhou, Xilong; Ji, Baoping; Ren, Wanpeng

    2016-10-15

    Two novel immunizing haptens of 3-methyl-quinoxaline-2-carboxylic acid (MQCA) were synthesized and conjugated with cationized bovine serum albumin. Female BALB/c mice were immunized with above conjugates, splenocytes were fused with Sp2/0 cells to produce monoclonal antibody. Compared with previous studies, antibodies raised in this work showed higher sensitivity. Meantime, a novel heterologous coating hapten was also prepared. The indirect competitive enzyme-linked immunosorbent assay (icELISA) based on the optimum condition showed an IC50 of 3.1μg/kg (ppb), and the linear range of 0.46-10.5ppb for MQCA. The limit of detect (LOD) of MQCA in swine muscle, swine liver and chicken was 0.32, 0.54, and 0.28ppb, respectively. The LOD of this assay can satisfy the minimum required performance levels (4ppb) for MQCA. These results indicated that the proposed ELISA, with high sensitivity and specificity, as well as good reproducibility and accuracy, is suitable for determination of MQCA residues in food samples. PMID:27173564

  20. Saturable absorption and two-photon absorption of 1,2,5-thiadiazolo[3,4-g]quinoxaline based derivatives with near-infrared fluorescence

    NASA Astrophysics Data System (ADS)

    Du, Yabing; Lin, Xiaodong; Jia, Tingjian; Dong, Jun

    2015-03-01

    Organic molecules with near-infrared (NIR) fluorescence are extremely interesting for the applications in nonlinear optical devices and bioimaging. However, such kind of materials have been relatively rarely studied. In this work, the nonlinear optical properties of 1,2,5-thiadiazolo[3,4-g]quinoxaline based derivatives with NIR fluorescence emission have been investigated for the first time. Under the excitation of femtosecond pulses at 532 nm, the chromophore with dithienyl as donor (TQ2) presents saturable absorption (SA) behavior, while no SA has been observed in the derivative with biphenyl (TQ1) as donor. Moreover, TQ2 exhibits much larger two-photon absorption (TPA) cross-sections with strong NIR fluorescence in the second biological window. The larger nonlinear optical properties of TQ2 is due to the introduction of stronger electron-donating group (dithienyl) and the resultant enhanced intramolecular charge transfer properties. At the end, TPA based optical limiting behaviors of the molecules are demonstrated in THF solutions, thanks to their large solubility and strong TPA.

  1. Proton triggered emission and selective sensing of picric acid by the fluorescent aggregates of 6,7-dimethyl-2,3-bis-(2-pyridyl)-quinoxaline.

    PubMed

    Mazumdar, Prativa; Maity, Samir; Shyamal, Milan; Das, Debasish; Sahoo, Gobinda Prasad; Misra, Ajay

    2016-03-14

    A heteroatom containing organic fluorophore 6,7-dimethyl-2,3-bis-(2-pyridyl)-quinoxaline (BPQ) is weakly emissive in solution but its emission properties are highly enhanced in the aggregated state due to the restriction of intramolecular rotation (RIR) and large amplitude vibrational modes, demonstrating the phenomenon, aggregation induced emission enhancement (AIEE). It has strong proton capture capability, allowing reversible fluorescence switching in basic and acidic medium and the emission color changes from blue to green in the aggregated state through protonation. It has been explained as a competition between intramolecular charge transfers (ICTs) and the AIEE phenomena at a lower pH range (pH ∼1-4). Such behavior enables it as a fluorescent pH sensor for detection in acidic and basic medium. Morphologies of the particles are characterized using optical and field emission scanning electron microscopic (FESEM) studies. The turn off fluorescence properties of aggregated BPQ have been utilized for the selective detection of picric acid and the fluorescence quenching is explained due to ground state complexation with a strong quenching constant, 7.81 × 10(4) M(-1). PMID:26608816

  2. Speciation of selenium in environmental samples by solid-phase spectrophotometry using 2,3-dichloro-6-(2,7-dihydroxy-naphthylazo)quinoxaline.

    PubMed

    Amin, Alaa S

    2014-01-01

    Solid-phase spectrophotometry was applied to determination of trace amounts of selenium (Se) in water, soil, plant materials, human hair, and a cosmetic preparation (lipstick). Se(IV) was sorbed in a dextran type lipophilic gel as a complex with 2,3-dichloro-6-(2,7-dihydroxy-naphthylazo)quinoxaline (DCDHNAQ), whereas Se(VI) was determined after boiling in HCI for 10 min to convert Se(VI) to Se(IV). Resin phase absorbances at 588 and 800 nm were measured directly, which allowed the determination of Se in the range of 0.2-3.3 microg/L with an RSD of 1.22%. The influences of analytical parameters including pH of the aqueous solution, amounts of DCDHNAQ, and sample volume were investigated. The molar absorptivities were found to be 1.09 x 10(6), 4.60 x 10(6), and 1.23 x 10(7) L/mol cm for 100, 500, and 1000 mL, respectively. The LOD and LOQ of the 500 mL sample method were 110 and 360 ng/L, respectively, when using 50 mg dextran type lipophilic gel. For a 1000 mL sample, the LOD and LOQ were 60 and 200 ng/L, respectively, using 50 mg of the exchanger. Increasing the sample volume enhanced the sensitivity. No considerable interferences were observed from other investigated anions and cations on the Se determination. PMID:24830171

  3. Fragrance material review on 2-phenyl-2-propanol.

    PubMed

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-phenyl-2-propanol when used as a fragrance ingredient is presented. 2-Phenyl-2-propanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a tertiary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. 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 2-phenyl-2-propanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, skin sensitization, and toxicokinetics data. A safety assessment of the entire Aryl Alkyl Alcohols 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 Aryl Alkyl Alcohols in fragrances. PMID:22033099

  4. Fragrance material review on 1-phenyl-3-methyl-3-pentanol.

    PubMed

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 1-phenyl-3-methyl-3-pentanol when used as a fragrance ingredient is presented. 1-Phenyl-3-methyl-3-pentanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a tertiary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-Alkyl-C-(R1)(R2)OH group. 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 1-phenyl-3-methyl-3-pentanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, and genotoxicity data. A safety assessment of the entire Aryl Alkyl Alcohols 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 Aryl Alkyl Alcohols in fragrances. PMID:22033089

  5. Fragrance material review on 2-methyl-4-phenyl-2-butanol.

    PubMed

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butanol when used as a fragrance ingredient is presented. 2-methyl-4-phenyl-2-butanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a tertiary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. 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 2-methyl-4-phenyl-2-butanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, and skin sensitization data. A safety assessment of the entire Aryl Alkyl Alcohols 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 Aryl Alkyl Alcohols in fragrances. assessment of aryl alkyl alcohols when used as fragrance ingredients. PMID:22036982

  6. 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. PMID:22433983

  7. Synthesis of 2-(methylsulfonyl)-5-(4-(methylsulfonyl) phenyl)-4-phenyl-1H-[5-(14) C]imidazole, a selective COX-2 inhibitor, via asymmetrical benzoins.

    PubMed

    Shirvani, Gholamhossein; Shockravi, Abbas; Amini, Mohsen; Saemian, Nader

    2016-04-01

    4,5-Diarylimidazoles labeled with carbon-14 in the 5-position of the imidazole ring were prepared as a part of three-step sequence from 2-hydroxy-1-(4-(methylthio)phenyl)-2-phenyl[1-(14) C]ethanone as a key synthetic intermediate which has been synthesized from potassium [(14) C]cyanide. PMID:26916231

  8. 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-...

  9. 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-...

  10. 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-...

  11. 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.

  12. Enzymatic synthesis of S-phenyl-L-cysteine from keratin hydrolysis industries wastewater with tryptophan synthase.

    PubMed

    Xu, Lisheng; Wang, Zhiyuan; Mao, Pingting; Liu, Junzhong; Zhang, Hongjuan; Liu, Qian; Jiao, Qing-Cai

    2013-04-01

    An economical method for production of S-phenyl-L-cysteine from keratin acid hydrolysis wastewater (KHW) containing L-serine was developed by recombinant tryptophan synthase. This study provides us with an alternative KHW utilization strategy to synthesize S-phenyl-L-cysteine. Tryptophan synthase could efficiently convert L-serine contained in KHW to S-phenyl-L-cysteine at pH 9.0, 40°C and Trion X-100 of 0.02%. In a scale up study, L-serine conversion rate reach 97.1% with a final S-phenyl-L-cysteine concentration of 38.6 g l(-1). PMID:23478091

  13. Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

    PubMed Central

    2014-01-01

    A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration. PMID:25147607

  14. The critical role of oxidative stress in the toxicity and metabolism of quinoxaline 1,4-di-N-oxides in vitro and in vivo.

    PubMed

    Wang, Xu; Martínez, María-Aránzazu; Cheng, Guyue; Liu, Zhaoying; Huang, Lingli; Dai, Menghong; Chen, Dongmei; Martínez-Larrañaga, María-Rosa; Anadón, Arturo; Yuan, Zonghui

    2016-05-01

    Quinoxaline 1,4-dioxide derivatives (QdNOs) have been widely used as growth promoters and antibacterial agents. Carbadox (CBX), olaquindox (OLA), quinocetone (QCT), cyadox (CYA) and mequindox (MEQ) are the classical members of QdNOs. Some members of QdNOs are known to cause a variety of toxic effects. To date, however, almost no review has addressed the toxicity and metabolism of QdNOs in relation to oxidative stress. This review focused on the research progress associated with oxidative stress as a plausible mechanism for QdNO-induced toxicity and metabolism. The present review documented that the studies were performed over the past 10 years to interpret the generation of reactive oxygen species (ROS) and oxidative stress as the results of QdNO treatment and have correlated them with various types of QdNO toxicity, suggesting that oxidative stress plays critical roles in their toxicities. The major metabolic pathways of QdNOs are N→O group reduction and hydroxylation. Xanthine oxidoreductase (XOR), aldehyde oxidase (SsAOX1), carbonyl reductase (CBR1) and cytochrome P450 (CYP) enzymes were involved in the QdNOs metabolism. Further understanding the role of oxidative stress in QdNOs-induced toxicity will throw new light onto the use of antioxidants and scavengers of ROS as well as onto the blind spots of metabolism and the metabolizing enzymes of QdNOs. The present review might contribute to revealing the QdNOs toxicity, protecting against oxidative damage and helping to improve the rational use of concurrent drugs, while developing novel QdNO compounds with more efficient potentials and less toxic effects. PMID:27285897

  15. 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.

  16. N,N′-(Oxydi-p-phenyl­ene)diphthalimide

    PubMed Central

    Li, Yi-Tao; Wang, Zhiguo

    2008-01-01

    The title compound, C28H16N2O5, is a bis-imide derivative in which two phthalimide units are linked by an oxydi-p-phenyl­ene bridge. The dihedral angle between the planes of the two central benzene rings is 86.1 (4)°. The isoindole groups make dihedral angles of 46.0 (14) and 77.5 (13)° with the attached benzene rings. Inter­molecular C—H⋯O hydrogen bonds contribute to the stability of the structure. PMID:21200954

  17. 4-Phenyl­diazenyl-2-[(R)-(1-phenyl­ethyl)imino­meth­yl]phenol

    PubMed Central

    Aritake, Yoshikazu; Watanabe, Yoshimasa; Akitsu, Takashiro

    2010-01-01

    The title chiral photochromic Schiff base compound, C21H19N3O, was synthesized from (R)-1-phenyl­ethyl­amine and the salicylaldehyde of an azobenzene derivative. The mol­ecule corresponds to the phenol–imine tautomer, the C=N and N—C bond distances being 1.279 (3) and 1.477 (3) Å, respectively. An intra­molecular O—H⋯N hydrogen bond occurs. The diazenyl group adopts a trans form with an N=N distance of 1.243 (3) Å. PMID:21580594

  18. 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. PMID:11830761

  19. 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.

  20. Influence of the ester chain length on the mesogenic behavior and optical anisotropy of 4-[[4-(butoxy)phenyl]diazenyl]phenyl alkanoates

    NASA Astrophysics Data System (ADS)

    Niezgoda, Izabela; Szypszak, Ewelina; Dardas, Dorota; Galewski, Zbigniew

    2016-04-01

    In this manuscript, we report synthesis and physico-chemical characterization of 4-[[4-(butoxy)phenyl]diazenyl]phenyl alkanoates homologous series. For the first time, nineteen derivatives are described here. The enantiotropic nematic phase is typically observed among all members of this series. However, in the case of 4-[[4-(butoxy)phenyl]diazenyl]phenyl stearate, the nematic phase shows a monotropic character. In addition to liquid-crystalline polymorphism, a second crystalline form was observed in some homologs. Furthermore, using a photoelastic modulator, the optical anisotropy in the nematic phase was determined in the first nine compounds of this series. Temperature dependence of optical anisotropy at significantly lower values of reduced temperature is relatively weak. In contrast, optical anisotropy shows a strong temperature effect near isotropization. Moreover, the influence of the ester chain elongation on liquid crystalline and optical properties was established.

  1. 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...

  2. 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...

  3. 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...

  4. 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...

  5. 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...

  6. 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...

  7. Ideal gas thermodynamic properties for the phenyl, phenoxy, and o-biphenyl radicals

    NASA Technical Reports Server (NTRS)

    Burcat, A.; Zeleznik, F. J.; Mcbride, B. J.

    1985-01-01

    Ideal gas thermodynamic properties of the phenyl and o-biphenyl radicals, their deuterated analogs and the phenoxy radical were calculated to 5000 K using estimated vibrational frequencies and structures. The ideal gas thermodynamic properties of benzene, biphenyl, their deuterated analogs and phenyl were also calculated.

  8. Asymmetric ligand-exchange reaction of biphenol derivatives and chiral bis(oxazolinyl)phenyl-rhodium complex.

    PubMed

    Inoue, Hiroko; Ito, Jun-ichi; Kikuchi, Makoto; Nishiyama, Hisao

    2008-09-01

    Chiral bis(oxazolinyl)phenyl-rhodium acetate complex can enantioselectively capture 1,1'-binaphthol derivatives by ligand-exchange reaction. The structure of the bis(oxazolinyl)phenyl-rhodium biphenol and binaphthol complexes were confirmed by X-ray analysis. PMID:18496824

  9. Crystal structure of an RNA duplex containing phenyl-ribonucleotides, hydrophobic isosteres of the natural pyrimidines.

    PubMed Central

    Minasov, G; Matulic-Adamic, J; Wilds, C J; Haeberli, P; Usman, N; Beigelman, L; Egli, M

    2000-01-01

    Chemically modified nucleotide analogs have gained widespread popularity for probing structure-function relationships. Among the modifications that were incorporated into RNAs for assessing the role of individual functional groups, the phenyl nucleotide has displayed surprising effects both in the contexts of the hammerhead ribozyme and pre-mRNA splicing. To examine the conformational properties of this hydrophobic base analog, we determined the crystal structure of an RNA double helix with incorporated phenyl ribonucleotides at 1.97 A resolution. In the structure, phenyl residues are engaged in self-pairing and their arrangements suggest energetically favorable stacking interactions with 3'-adjacent guanines. The presence of the phenyl rings in the center of the duplex results in only moderate changes of the helical geometry. This finding is in line with those of earlier experiments that showed the phenyl analog to be a remarkably good mimetic of natural base function. Because the stacking interactions displayed by phenyl residues appear to be similar to those for natural bases, reduced conformational restriction due to the lack of hydrogen bonds with phenyl as well as alterations in its solvent structure may be the main causes of the activity changes with phenyl-modified RNAs. PMID:11105752

  10. 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...

  11. 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...

  12. 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...

  13. Evaluation of phenyl carbonates as electrolyte additives in lithium-ion batteries

    NASA Astrophysics Data System (ADS)

    Petibon, R.; Rotermund, L. M.; Dahn, J. R.

    2015-08-01

    The impact of the electrolyte additives methyl phenyl carbonate, ethyl phenyl carbonate, and diphenyl carbonate was evaluated in Li[Ni0.33Mn0.33Co0.33]O2/graphite pouch cells with or without 2% vinylene carbonate. Experiments included high precision coulometry, automated storage, electrochemical impedance spectroscopy on symmetric cells and gas chromatography coupled with mass spectrometry. Gas chromatography/mass spectrometry analysis, electrochemical studies during the first charge and impedance spectroscopy on symmetric cells indicated that phenyl carbonates act as solid electrolyte interphase modifiers rather than formers. High precision coulometry showed that cells containing 1-4 wt% methyl phenyl carbonate, ethyl phenyl carbonate or diphenyl carbonate had similar coulombic efficiencies and charge-endpoint capacity slippage as cells filled with 2 wt% vinylene carbonate. Impedance spectroscopy showed that cells containing phenyl carbonates have substantially lower impedance than cells filled with 2 wt% vinylene carbonate and produced minimal volumes of gas during cell use. Results presented in the report show that phenyl carbonates are competitive additives for 4.2 V class cells and should lead to good cycle life, low polarization and low gas evolution during normal use. Phenyl carbonates can also be used as gas-producing safety agents (to trip pressure activated disconnects) in combination with vinylene carbonate in cylindrical or prismatic cells without adverse effects.

  14. 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...

  15. 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...

  16. 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...

  17. 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...

  18. 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...

  19. 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...

  20. 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...

  1. 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...

  2. 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...

  3. 40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Carbon black, 4- substituted] phenyl... Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl...) The chemical substance identified generically as carbon black, 4- substituted] phenyl-modified,...

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Carbon black, 4- substituted] phenyl... Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl...) The chemical substance identified generically as carbon black, 4- substituted] phenyl-modified,...

  5. 40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Carbon black, 4- substituted] phenyl... Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl...) The chemical substance identified generically as carbon black, 4- substituted] phenyl-modified,...

  6. 40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Carbon black, 4- substituted] phenyl... Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl...) The chemical substance identified generically as carbon black, 4- substituted] phenyl-modified,...

  7. 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... Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl...) The chemical substance identified generically as carbon black, 4- substituted] phenyl-modified,...

  8. 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...

  9. 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...

  10. 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...

  11. 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...

  12. 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...

  13. O-Propyl N-phenyl­thio­carbamate

    PubMed Central

    Sudkaow, Panyapon; Yeo, Chien Ing; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    Two independent mol­ecules comprise the asymmetric unit in the title thio­carbamide derivative, C10H13NOS. These differ in the relative orientations of terminal ethyl groups [C—C—C—O torsion angles = −66.95 (13) and 55.92 (13)°, respectively]. The phenyl ring is twisted out of the plane of the central residue [Cq—N—Cph—Cph = −146.20 (12) and −144.15 (12)°, respectively; q = quaternary and ph = phen­yl]. The independent mol­ecules are linked into a dimeric aggregate by N—H⋯S hydrogen bonds and an eight-membered thio­amide {⋯H—N—C=S}2 synthon. PMID:22719552

  14. Aging studies on thin tetra-phenyl butadiene films

    NASA Astrophysics Data System (ADS)

    Acciarri, R.; Canci, N.; Cavanna, F.; Segreto, E.; Szelc, A. M.

    2013-10-01

    Tetra-Phenyl Butadiene (TPB) is the most commonly used compound to wave-shift the 128 nm scintillation light of liquid Argon down to the visible spectrum. We present a study on the loss of conversion efficiency of thin TPB films evaporated on reflective foils when exposed to light and atmosphere. The efficiency of the films is measured and monitored with a dedicated set-up that uses gaseous Argon excited by alpha particles to produce 128 nm photons and working at room temperature. In particular we performed a two years long exposure of the samples to lab diffuse light and atmosphere. We also performed more controlled aging tests to investigate the effect of storing samples in a inert atmosphere.

  15. Reaction of dichlorocarbene with 2-phenyl-1,3-oxathiolane

    SciTech Connect

    Nazarov, D.V.; Safiev, O.G.; Zorin, V.V.; Rakhmankulov, D.L.

    1987-10-20

    It was established that the reaction of 2-phenyl-1,3-oxathiolane (I) with dichlorocarbene, generated from chloroform in 50% aqueous solution of sodium hydroxide with the use of triethylbenzylammonium chloride as phase-transfer catalyst, leads to the formation of dichloromethyl thiobenzoate (II) and ethylene with yields of 24 and 38% respectively and 60% conversion in the substrate (I). The reaction was conducted at 35-40/sup 0/C for 24 h with the following amounts of the reagents; 0.5 mole of the substrate (I); 5 moles of chloroform; 600 mol of 50% aqueous sodium hydroxide solution; 1 g of triethylbenzylammonium chloride. Compound (II) was isolated by column liquid chromatography on aluminum oxide (40-250 ..mu..) with a 1:5 mixture of diethyl ether and hexane as eluant. The product was identified by means of the IR, PMR, and /sup 13/C NMR spectra.

  16. Discovery of 4-phenyl-2-phenylaminopyridine based TNIK inhibitors.

    PubMed

    Ho, Koc-Kan; Parnell, K Mark; Yuan, Yi; Xu, Yong; Kultgen, Steven G; Hamblin, Steven; Hendrickson, Thomas F; Luo, Bai; Foulks, Jason M; McCullar, Michael V; Kanner, Steven B

    2013-01-15

    A series of compounds based on a 4-phenyl-2-phenylaminopyridine scaffold that are potent and selective inhibitors of Traf2- and Nck-interacting kinase (TNIK) activity are described. These compounds were used as tools to test the importance of TNIK kinase activity in signaling and proliferation in Wnt-activated colorectal cancer cells. The results indicate that pharmacological inhibition of TNIK kinase activity has minimal effects on either Wnt/TCF4/β-catenin-driven transcription or viability. The findings suggest that the kinase activity of TNIK may be less important to Wnt signaling than other aspects of TNIK function, such as its putative role in stabilizing the TCF4/β-catenin transcriptional complex. PMID:23232060

  17. 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. PMID:26891908

  18. Synthesis, Fourier transform infrared and Raman spectra, assignments and analysis of N-(phenyl)- and N-(chloro substituted phenyl)-2,2-dichloroacetamides.

    PubMed

    Arjunan, V; Mohan, S; Subramanian, S; Thimme Gowda, B

    2004-04-01

    N-(phenyl)-2,2-dichloroacetamide (NPA) and N-(chloro substituted phenyl)-2,2-dichloroacetamides of the configuration XyC6H(5-y)-NHCO-CHCl2 (where, X = Cl and y = 1, 2 and 3) were synthesised and the Fourier transform infrared (FTIR) and Fourier transform Raman (FT-Raman) spectra of the compounds were recorded and analysed. The FTIR spectra of all the compounds were recorded in a Bruker IFS 66V spectrometer in the range of 4000-400 cm(-1) and the FT-Raman spectra were also recorded in the same instrument in the region 3500-100 cm(-1). The variation of an amide bond (-NHCO-) parameters with the substitution of the chlorine atom in the phenyl group and the mixing of different normal modes are discussed with the help of potential energy distribution (PED) calculated through normal co-ordinate analysis. PMID:15084334

  19. Synthesis of 1-phenyl-2-(phenylcarbamoyl)pyrazolidines as potential anticonvulsant agents.

    PubMed

    Kornet, M J; Garrett, R J

    1979-03-01

    Twelve 1-phenyl-2-(phenylcarbamoyl)pyrazolidines were synthesized from 1-arylpyrazolidines and aryl isocyanates. These adducts showed little anticonvulsant activity in the maximal electroshock seizure and pentylenetetrazol seizure assays. PMID:423135

  20. Ultrafast Dynamics of Polythiophene with Phenyl Vinylene Branches Studied by Femtosecond Fluorescence Spectroscopy in Solution

    NASA Astrophysics Data System (ADS)

    Chu, Sai-Sai; Gao, Chao; Wang, Shu-Feng; Gong, Qi-Huang

    2011-11-01

    Two polythiophene based polymers, poly[(3-[2-[4-(2-ethyl-hexyloxy)-phenyl]-vinyl]-thiophene)-co-thiophene] (PT1) and poly(3-[2-[4-(2-ethyl-hexyloxy)-phenyl]-vinyl]-thiophene) (PT2), are synthesized and investigated by static, picosecond fluorescence spectroscopies and the femtosecond up-conversion technique in solution. Compared with pristine poly(3-hexylthiophene) (P3HT), PT1 and PT2, in which the main chains are decorated with phenyl vinylene present a ‘camel back’ structure in the absorption spectra. Phenyl vinylene side chains induce a new process of charge transfer, chain twisting motion and defect-induced fluorescence quenching at time scales of 1 ps, 10 ps and 150 ps, respectively.

  1. 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)

  2. 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.

  3. 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.

  4. Experimental and theoretical investigation of the self-reaction of phenyl radicals.

    SciTech Connect

    Tranter, R. S.; Klippenstein, S. J.; Harding, L. B.; Giri, B. R.; Yang, X.; Kiefer, J. H.; Chemical Sciences and Engineering Division; Univ. of Illinois at Chicago

    2010-08-19

    A combination of experiment and theory is applied to the self-reaction kinetics of phenyl radicals. The dissociation of phenyl iodide is observed with both time-of-flight mass spectrometry, TOF-MS, and laser schlieren, LS, diagnostics coupled to a diaphragmless shock tube for temperatures ranging from 1276 to 1853 K. The LS experiments were performed at pressures of 22 {+-} 2, 54 {+-} 7, and 122 {+-} 6 Torr, and the TOF-MS experiments were performed at pressures in the range 500-700 Torr. These observations are sensitive to both the dissociation of phenyl iodide and to the subsequent self-reaction of the phenyl radicals. The experimental observations indicate that both these reactions are more complicated than previously assumed. The phenyl iodide dissociation yields {approx}6% C{sub 6}H{sub 4} + HI in addition to the major and commonly assumed C{sub 6}H{sub 5} + I channel. The self-reaction of phenyl radicals does not proceed solely by recombination, but also through disproportionation to benzene + o-/m-/p-benzynes, with comparable rate coefficients for both. The various channels in the self-reaction of phenyl radicals are studied with ab initio transition state theory based master equation calculations. These calculations elucidate the complex nature of the C{sub 6}H{sub 5} self-reaction and are consistent with the experimental observations. The theoretical predictions are used as a guide in the development of a model for the phenyl iodide pyrolysis that accurately reproduces the observed laser schlieren profiles over the full range of the observations.

  5. Phenyl shifts in substituted arenes via ipso arenium ions.

    PubMed

    Ajaz, Aida; McLaughlin, Erin C; Skraba, Sarah L; Thamatam, Rajesh; Johnson, Richard P

    2012-11-01

    The isomerization of substituted arenes through ipso arenium ions is an important and general molecular rearrangement that leads to interconversions of constitutional isomers. We show here that the superacid trifluoromethanesulfonic acid (TfOH), ca. 1 M in dichloroethane (DCE), provides reliable catalytic reaction conditions for these rearrangements, easily applied at ambient temperature, reflux (84 °C), or in a microwave reactor for higher temperatures. Interconversion of terphenyl isomers in TfOH/DCE at 84 °C gives an ortho/meta/para equilibrium ratio of 0:65:35, nearly identical to values reported earlier by Olah with catalysis by AlCl(3). For the three triphenylbenzenes, TfOH-catalyzed equilibration strongly (>95%) favors the 1,3,5-triphenyl isomer. Equilibration of the three possible tetraphenylbenzenes gives a 61:39 mixture of the 1,2,3,5- and 1,2,4,5-substituted isomers. Under the reaction conditions explored, none of these structures undergoes significant Scholl cyclization. DFT calculations with inclusion of solvation support a mechanistic scheme in which all of the phenyl migrations occur among a series of ipso arenium ions. In every case studied, the preferred isomers at equilibrium are those that yield highly stable cations by the most exothermic, hence least reversible 1,2-H shift. PMID:23061916

  6. O-Phenyl Carbamate and Phenyl Urea Thiiranes as Selective Matrix Metalloproteinase-2 Inhibitors that Cross the Blood-Brain Barrier

    PubMed Central

    Gooyit, Major; Song, Wei; Mahasenan, Kiran V.; Lichtenwalter, Katerina; Suckow, Mark A.; Schroeder, Valerie A.; Wolter, William R.; Mobashery, Shahriar; Chang, Mayland

    2013-01-01

    Brain metastasis occurs in 20% to 40% of cancer patients. Treatment is mostly palliative and the inability of most drugs to penetrate the brain presents one of the greatest challenges in the development of therapeutics for brain metastasis. Matrix metalloproteinase-2 (MMP-2) plays important roles in invasion and vascularization of the central nervous system and represents a potential target for treatment of brain metastasis. Carbonate, O-phenyl carbamate, urea, and N-phenyl carbamate derivatives of SB-3CT, a selective and potent gelatinase inhibitor were synthesized and evaluated. The O-phenyl carbamate and urea variants were selective and potent inhibitors of MMP-2. Carbamate 5b was metabolized to the potent gelatinase inhibitor 2, which was present at therapeutic concentrations in the brain. In contrast, phenyl urea 6b crossed the blood-brain barrier, however higher doses would result in therapeutic brain concentrations. Carbamate 5b and urea 6b show potential for intervention of MMP-2-dependent diseases, such as brain metastasis. PMID:24028490

  7. O-phenyl carbamate and phenyl urea thiiranes as selective matrix metalloproteinase-2 inhibitors that cross the blood-brain barrier.

    PubMed

    Gooyit, Major; Song, Wei; Mahasenan, Kiran V; Lichtenwalter, Katerina; Suckow, Mark A; Schroeder, Valerie A; Wolter, William R; Mobashery, Shahriar; Chang, Mayland

    2013-10-24

    Brain metastasis occurs in 20-40% of cancer patients. Treatment is mostly palliative, and the inability of most drugs to penetrate the brain presents one of the greatest challenges in the development of therapeutics for brain metastasis. Matrix metalloproteinase-2 (MMP-2) plays important roles in invasion and vascularization of the central nervous system and represents a potential target for treatment of brain metastasis. Carbonate, O-phenyl carbamate, urea, and N-phenyl carbamate derivatives of SB-3CT, a selective and potent gelatinase inhibitor, were synthesized and evaluated. The O-phenyl carbamate and urea variants were selective and potent inhibitors of MMP-2. Carbamate 5b was metabolized to the potent gelatinase inhibitor 2, which was present at therapeutic concentrations in the brain. In contrast, phenyl urea 6b crossed the blood-brain barrier, however, higher doses would result in therapeutic brain concentrations. Carbamate 5b and urea 6b show potential for intervention of MMP-2-dependent diseases such as brain metastasis. PMID:24028490

  8. Crystal structure of 1′,1′′-dimethyl-4′-(4-cholorophen­yl)di­spiro­[11H-indeno[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one

    PubMed Central

    Nagalakshmi, R.A.; Suresh, J.; Malathi, K.; Kumar, R. Ranjith; Lakshman, P. L. Nilantha

    2015-01-01

    In the title compound, C30H27ClN4O, the central pyrrolidine ring adopts an envelope conformation with the methyl­ene C atom being the flap. The quinoxaline and indane rings are each essentially planar, with r.m.s. deviations of 0.027 (1) and 0.0417 (1) Å, respectively. The pyrrolidine ring forms dihedral angles of 88.25 (1) and 83.76 (1)° with the quinoxaline and indane rings, respectively. A weak intra­molecular C—H⋯N inter­action is observed. In the crystal, C—H⋯π inter­actions lead to supra­molecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type Cl⋯Cl [3.6538 (16) Å]. PMID:25878875

  9. 3-Acetyl-1-(3-methyl­phen­yl)-5-phenyl-1H-pyrazole-4-carbonitrile

    PubMed Central

    Abdel-Aziz, Hatem A.; Al-Obaid, Abdul-Rahman M.; Ghabbour, Hazem A.; Hemamalini, Madhukar; Fun, Hoong-Kun

    2012-01-01

    In the title compound, C19H15N3O, the central pyrazole ring makes dihedral angles of 35.52 (12) and 62.21 (11)° with the attached phenyl and methyl-substituted phenyl rings, respectively. The corresponding angle between the phenyl and methyl-substituted phenyl rings is 62.90 (11)°. In the crystal, mol­ecules are connected by weak C—H⋯O hydrogen bonds, forming supra­molecular chains propagating along the a-axis direction. PMID:22347089

  10. Role of carbon-carbon phenyl migration in the pyrolysis mechanism of β-O-4 lignin model compounds: phenethyl phenyl ether and α-hydroxy phenethyl phenyl ether.

    PubMed

    Beste, Ariana; Buchanan, A C

    2012-12-20

    We investigate phenyl shift and subsequent β-scission reactions for PhCHXCH·OPh [X = H, OH], which are part of the pyrolysis mechanism of phenethyl phenyl ether (PPE) and α-hydroxy PPE. PPE and its derivatives are model compounds for the most common linkage in lignin, the β-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. However, while subsequent β-scission of the oxygen-carbon shift products proceeds with virtually no barrier, the activation energy for β-scission of the carbon-carbon shift products exceeds 15 kcal/mol. We found that about 15% of β-radical conversion can be attributed to carbon-carbon shift for PPE and α-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. PMID:23194314

  11. 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.

  12. 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. PMID:19910246

  13. Optical Poling of Phenyl-Silica Hybrid Thin Films Doped with Azo-Dye Chromophore

    NASA Astrophysics Data System (ADS)

    Kitaoka, Kenji; Matsuoka, Nobuaki; Si, Jinhai; Mitsuyu, Tsuneo; Hirao, Kazuyuki

    1999-09-01

    Azo-dye doped phenly group substituted silica films were prepared by a sol-gel method from a solution of triethoxyphenlysilane (TEPh), tetraethoxysilane (TEOS) and 4-[N-ethyl-N-(2-hydroxyethyl)]amino-4‧-nitro-azobenzene (DR1). The films were optically poled by the coherent superposition of 1064 nm and 532 nm beams from a Q-switched Nd:YAG laser. Second-order susceptibility χeff of a DR1 doped phenyl group substituted film induced by the optical poling was approximately four times as large as that of the phenyl-free film. The phenyl group in the silica matrix was found to be effective for increasing the second-order nonlinearity and increasing the thermal stability.

  14. Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors.

    PubMed

    Hameed, Abdul; Khan, Khalid Mohammed; Zehra, Syeda Tazeen; Ahmed, Ramasa; Shafiq, Zahid; Bakht, Syeda Mahwish; Yaqub, Muhammad; Hussain, Mazhar; de la Vega de León, Antonio; Furtmann, Norbert; Bajorath, Jürgen; Shad, Hazoor Ahmad; Tahir, Muhammad Nawaz; Iqbal, Jamshed

    2015-08-01

    Urease is an important enzyme which breaks urea into ammonia and carbon dioxide during metabolic processes. However, an elevated activity of urease causes various complications of clinical importance. The inhibition of urease activity with small molecules as inhibitors is an effective strategy for therapeutic intervention. Herein, we have synthesized a series of 19 benzofurane linked N-phenyl semithiocarbazones (3a-3s). All the compounds were screened for enzyme inhibitor activity against Jack bean urease. The synthesized N-phenyl thiosemicarbazones had varying activity levels with IC50 values between 0.077 ± 0.001 and 24.04 ± 0.14 μM compared to standard inhibitor, thiourea (IC50 = 21 ± 0.11 μM). The activities of these compounds may be due to their close resemblance of thiourea. A docking study with Jack bean urease (PDB ID: 4H9M) revealed possible binding modes of N-phenyl thiosemicarbazones. PMID:26119990

  15. 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.

  16. 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.

  17. Influence of the substituents on the electronic and electrochemical properties of a new square-planar nickel-bis(quinoxaline-6,7-dithiolate) system: synthesis, spectroscopy, electrochemistry, crystallography, and theoretical investigation.

    PubMed

    Bolligarla, Ramababu; Reddy, Samala Nagaprasad; Durgaprasad, Gummadi; Sreenivasulu, Vudagandla; Das, Samar K

    2013-01-01

    We describe the synthesis, crystal structures, electronic absorption spectra, and electrochemistry of a series of square-planar nickel-bis(quinoxaline-6,7-dithiolate) complexes with the general formula [Bu(4)N](2)[Ni(X(2)6,7-qdt)(2)], where X = H (1a), Ph (2a), Cl (3), and Me (4). The solution and solid-state electronic absorption spectral behavior and electrochemical properties of these compounds are strongly dependent on the electron donating/accepting nature of the substituent X, attached to the quinoxaline-6,7-dithiolate ring in the system [Bu(4)N](2)[Ni(X(2)6,7-qdt)(2)]. Particularly, the charge transfer (CT) transition bands observed in the visible region are greatly affected by the electronic nature of the substituent. A possible explanation for this influence of the substituents on electronic absorption and electrochemistry is described based on highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) gaps, which is further supported by ground-state electronic structure calculations. In addition to this, the observed CT bands in all the complexes are sensitive to the solvent polarity. Interestingly, compounds 1a, 2a, 3, and 4 undergo reversible oxidation at very low oxidation potentials appearing at E(1/2) = +0.12 V, 0.033 V, 0.18 V, and 0.044 V vs Ag/AgCl, respectively, in MeOH solutions, corresponding to the respective couples [Ni(X(2)6,7-qdt)(2)](-)/[Ni(X(2)6,7-qdt)(2)](2-). Compounds 1a, 3, and 4 have been characterized unambiguously by single crystal X-ray structural analysis; compound 2a could not be characterized by single crystal X-ray structure determination because of the poor quality of the concerned crystals. Thus, we have synthesized the tetraphenyl phosphonium salt of the complex anion of 2a, [PPh(4)](2)[Ni(Ph(2)6,7-qdt)(2)]·3DMF (2b) for its structural characterization. PMID:23214512

  18. Controlled switching of single-molecule junctions by mechanical motion of a phenyl ring.

    PubMed

    Kitaguchi, Yuya; Habuka, Satoru; Okuyama, Hiroshi; Hatta, Shinichiro; Aruga, Tetsuya; Frederiksen, Thomas; Paulsson, Magnus; Ueba, Hiromu

    2015-01-01

    Mechanical methods for single-molecule control have potential for wide application in nanodevices and machines. Here we demonstrate the operation of a single-molecule switch made functional by the motion of a phenyl ring, analogous to the lever in a conventional toggle switch. The switch can be actuated by dual triggers, either by a voltage pulse or by displacement of the electrode, and electronic manipulation of the ring by chemical substitution enables rational control of the on-state conductance. Owing to its simple mechanics, structural robustness, and chemical accessibility, we propose that phenyl rings are promising components in mechanical molecular devices. PMID:26665080

  19. 3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile

    PubMed Central

    Abdel-Aziz, Hatem A.; Ghabbour, Hazem A.; Chantrapromma, Suchada; Fun, Hoong-Kun

    2012-01-01

    In the title pyrazole derivative, C19H15N3O, the central pyrazole ring makes dihedral angles of 42.71 (9) and 61.34 (9)°, respectively, with the phenyl and p-tolyl rings. The dihedral angle between the phenyl and p-tolyl rings is 58.22 (9)°. The 3-acetyl-1H-pyrazole-4-carbonitrile unit is essentially planar, with an r.m.s. deviation of 0.0295 (1) Å for the ten non-H atoms. PMID:22606111

  20. Reaction dynamics of phenyl radicals in extreme environments: a crossed molecular beam study.

    PubMed

    Gu, Xibin; Kaiser, Ralf I

    2009-02-17

    Polycyclic aromatic hydrocarbons (PAHs)organic compounds that consist of fused benzene ringsand their hydrogen-deficient precursors have attracted extensive interest from combustion scientists, organic chemists, astronomers, and planetary scientists. On Earth, PAHs are toxic combustion products and a source of air pollution. In the interstellar medium, research suggests that PAHs play a role in unidentified infrared emission bands, diffuse interstellar bands, and the synthesis of precursor molecules to life. To build clean combustion devices and to understand the astrochemical evolution of the interstellar medium, it will be critical to understand the elementary reaction mechanisms under single collision conditions by which these molecules form in the gas phase. Until recently, this work had been hampered by the difficulty in preparing a large concentration of phenyl radicals, but the phenyl radical represents one of the most important radical species to trigger PAH formation in high-temperature environments. However, we have developed a method for producing these radical species and have undertaken a systematic experimental investigation. In this Account, we report on the chemical dynamics of the phenyl radical (C(6)H(5)) reactions with the unsaturated hydrocarbons acetylene (C(2)H(2)), ethylene (C(2)H(4)), methylacetylene (CH(3)CCH), allene (H(2)CCCH(2)), propylene (CH(3)CHCH(2)), and benzene (C(6)H(6)) utilizing the crossed molecular beams approach. For nonsymmetric reactants such as methylacetylene and propylene, steric effects and the larger cones of acceptance drive the addition of the phenyl radical to the nonsubstituted carbon atom of the hydrocarbon reactant. Reaction intermediates decomposed via atomic hydrogen loss pathways. In the phenyl-propylene system, the longer lifetime of the reaction intermediate yielded a more efficient energy randomization compared with the phenyl-methylacetylene system. Therefore, two reaction channels were open: hydrogen

  1. Controlled switching of single-molecule junctions by mechanical motion of a phenyl ring

    PubMed Central

    Kitaguchi, Yuya; Habuka, Satoru; Hatta, Shinichiro; Aruga, Tetsuya; Paulsson, Magnus; Ueba, Hiromu

    2015-01-01

    Summary Mechanical methods for single-molecule control have potential for wide application in nanodevices and machines. Here we demonstrate the operation of a single-molecule switch made functional by the motion of a phenyl ring, analogous to the lever in a conventional toggle switch. The switch can be actuated by dual triggers, either by a voltage pulse or by displacement of the electrode, and electronic manipulation of the ring by chemical substitution enables rational control of the on-state conductance. Owing to its simple mechanics, structural robustness, and chemical accessibility, we propose that phenyl rings are promising components in mechanical molecular devices. PMID:26665080

  2. Micro- or nanorod and nanosphere structures derived from a series of phenyl-porphyrins.

    PubMed

    Reddy, M Harsha Vardhan; Al-Shammari, Rusul M; Al-Attar, Nebras; Kennedy, Eamonn; Rogers, Luke; Lopez, Sergio; Senge, Mathias O; Keyes, Tia E; Rice, James H

    2014-03-01

    We examine here a series of meso-phenyl porphyrin micro- and nanostructures. Optical absorption and emission spectroscopy imaging and atomic force microscopy are used to investigate the effect of peripheral groups in nano- and microstructures of 5,10,15,20-tetraphenylporphyrin (H2TPP) compared to three other phenylporphyrins, i.e. 5,10,15-triphenylporphyrin (H2-Tri-PP), 5,10-diphenylporphyrin (H25,10-BPP) and 5,15-diphenylporphyrin (H25,15-BPP) molecules. We show that nanospheres and nanorods are formed, the occurrence and properties of which are influenced by the number and position of the phenyl substituents. PMID:24458009

  3. 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

  4. 40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl)oxy]carbonyl] amino]phenyl]amino...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Poly(oxyalkylenediyl), .alpha...(oxyalkylenediyl), .alpha.- carbonyl] amino]phenyl]amino]carbonyl]- .omega.-methoxy-(generic). (a) Chemical... as poly(oxyalkylenediyl), .alpha.- carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Poly(oxyalkylenediyl), .alpha...(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. 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…

  7. 40 CFR 721.5930 - Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic name). 721.5930 Section 721... Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic... identified generically as phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo...

  8. 40 CFR 721.5930 - Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic name). 721.5930 Section 721... Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic... identified generically as phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo...

  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

    ...)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic name). 721.5930 Section 721... Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic... identified generically as phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo...

  10. 40 CFR 721.5930 - Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic name). 721.5930 Section 721... Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic... identified generically as phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo...

  11. 40 CFR 721.5930 - Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic name). 721.5930 Section 721... Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt (generic... identified generically as phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo...

  12. Photochemical synthesis and anticancer activity of barbituric acid, thiobarbituric acid, thiosemicarbazide, and isoniazid linked to 2-phenyl indole derivatives.

    PubMed

    Laxmi, S Vijaya; Rajitha, G; Rajitha, B; Rao, Asha Jyothi

    2016-04-01

    2-Phenyl-1H-indole-3-carbaldehyde-based barbituric acid, thiobarbituric acid, thiosemicarbazide, isoniazid, and malononitrile derivatives were synthesized under photochemical conditions. The antitumor activities of the synthesized compounds were evaluated on three different human cancer cell lines representing prostate cancer cell line DU145, Dwivedi (DWD) cancer cell lines, and breast cancer cell line MCF7. All the screened compounds possessed moderate anticancer activity, and out of all the screened compounds, 5-{1[2-(4-chloro-phenyl)2-oxo-ethyl]-2-phenyl-1H-indole-3-ylmethylene}-2-thioxo-dihydro-pyrimidine-4,6-dione (2b) and 5-{1[2-(4-methoxy-phenyl)2-oxo-ethyl]-2-phenyl-1H-indole-3-ylmethylene}-2-thioxo-dihydro-pyrimidine-4,6-dione (2d) exhibited marked antitumor activity against used cell lines. Additionally, barbituric acid derivatives were selective to inhibit cell line DWD and breast cancer cell lines. PMID:27118996

  13. Exerting control over the helical chirality in the main chain of sergeants-and-soldiers-type poly(quinoxaline-2,3-diyl)s by changing from random to block copolymerization protocols.

    PubMed

    Nagata, Yuuya; Nishikawa, Tsuyoshi; Suginome, Michinori

    2015-04-01

    Chiral random poly(quinoxaline-2,3-diyl) polymers of the sergeants-and-soldiers-type (sergeant units bearing (S)-3-octyloxymethyl groups) adopt an M- or P-helical conformation in the presence of achiral units bearing propoxymethyl or butoxy groups (soldier units), respectively. Unusual bidirectional induction of the helical sense can be observed for a copolymer with butoxy soldier units upon changing the mole fraction of the sergeant units. In the presence of 16-20% of sergeant units, the selective induction of a P-helix was observed, while the selective induction of an M-helix was observed for a mole fraction of sergeant units of more than 60%. This phenomenon could be successfully employed to control the helical chirality of copolymers by applying either random or block copolymerization protocols. Random or block copolymerization of sergeant and soldier monomers in a 18:82 ratio resulted in the formation of 250mers with almost absolute P- or M-helical conformation, respectively (>99% ee). Incorporation of a small amount of coordination sites into the random and block copolymers resulted in chiral macromolecular ligands, which allowed the enantioselective synthesis of both enantiomers in the Pd-catalyzed asymmetric hydrosilylation of β-methylstyrene. PMID:25793617

  14. 40 CFR 721.10080 - Carbon black, 4-[(17-substituted-3,6,9,12,15-pentaazaheptadec-1-yl) substituted] phenyl-modified...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Carbon black, 4- phenyl-modified... Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a... generically as carbon black, 4- phenyl-modified, hydrochlorides (PMN P-06-8) is subject to reporting...

  15. 40 CFR 721.10080 - Carbon black, 4-[(17-substituted-3,6,9,12,15-pentaazaheptadec-1-yl) substituted] phenyl-modified...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Carbon black, 4- phenyl-modified... Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a... generically as carbon black, 4- phenyl-modified, hydrochlorides (PMN P-06-8) is subject to reporting...

  16. 40 CFR 721.10080 - Carbon black, 4-[(17-substituted-3,6,9,12,15-pentaazaheptadec-1-yl) substituted] phenyl-modified...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Carbon black, 4- phenyl-modified... Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a... generically as carbon black, 4- phenyl-modified, hydrochlorides (PMN P-06-8) is subject to reporting...

  17. 40 CFR 721.10080 - Carbon black, 4-[(17-substituted-3,6,9,12,15-pentaazaheptadec-1-yl) substituted] phenyl-modified...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Carbon black, 4- phenyl-modified... Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a... generically as carbon black, 4- phenyl-modified, hydrochlorides (PMN P-06-8) is subject to reporting...

  18. 40 CFR 721.10080 - Carbon black, 4-[(17-substituted-3,6,9,12,15-pentaazaheptadec-1-yl) substituted] phenyl-modified...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Carbon black, 4- phenyl-modified... Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a... generically as carbon black, 4- phenyl-modified, hydrochlorides (PMN P-06-8) is subject to reporting...

  19. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid,...

  20. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid,...

  1. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid,...

  2. 40 CFR 721.1620 - Benzenesulfonamide, alkylphenyl substituted phenyl substituted carbonyl- (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... phenyl substituted carbonyl- (PMN P-00-368) is subject to reporting under this section for the... in § 721.125(a), (b), (c), (d), (f), (g), (h), and (k) are applicable to manufacturers, importers... ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF...

  3. 40 CFR 721.1620 - Benzenesulfonamide, alkylphenyl substituted phenyl substituted carbonyl- (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... phenyl substituted carbonyl- (PMN P-00-368) is subject to reporting under this section for the... in § 721.125(a), (b), (c), (d), (f), (g), (h), and (k) are applicable to manufacturers, importers... ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF...

  4. 40 CFR 721.1620 - Benzenesulfonamide, alkylphenyl substituted phenyl substituted carbonyl- (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... phenyl substituted carbonyl- (PMN P-00-368) is subject to reporting under this section for the... in § 721.125(a), (b), (c), (d), (f), (g), (h), and (k) are applicable to manufacturers, importers... ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF...

  5. 40 CFR 721.1620 - Benzenesulfonamide, alkylphenyl substituted phenyl substituted carbonyl- (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... phenyl substituted carbonyl- (PMN P-00-368) is subject to reporting under this section for the... in § 721.125(a), (b), (c), (d), (f), (g), (h), and (k) are applicable to manufacturers, importers... ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF...

  6. 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.

  7. Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies.

    PubMed

    Veselinović, Jovana B; Veselinović, Aleksandar M; Vitnik, Željko J; Vitnik, Vesna D; Nikolić, Goran M

    2014-05-01

    A study on the structure-activity relationship of three hydroxy 4-phenyl coumarins, carried out by employing a series of different chemical cell-free tests is presented. Different assays involving one redox reaction with the oxidant (DPPH, ABTS, FRAP and CUPRAC) were employed. Further, the measurement of inhibition of oxidative degradation, such as lipid peroxidation, was used to define compound antioxidant activity. Our results confirm the good antioxidant activity of the 7,8-dihydroxy-4-phenyl coumarin and moderate antioxidant activity of 5,7-dihydroxy-4-phenyl coumarin. In this work, quantum chemical calculations based on density functional theory have been employed at B3LYP/6-311++G(d,p) level of theory to study the influence of number and position of hydroxyl groups in coumarin molecules on antioxidant activity. Calculated values for HOMO and LUMO energies, energy gap, stabilization energies and spin density distribution confirmed experimental results and were used for SAR definition. For determination of reaction mechanism in gas phase and selected solvents bond dissociation enthalpy, adiabatic ionization potential, proton dissociation enthalpy, proton affinity, electron transfer enthalpy and gas phase acidity have been calculated. Hydrogen Atom Transfer mechanism in vacuum and Single-Electron Transfer followed by the Proton Transfer mechanism in other studied systems are most probable free radical scavenging pathways. On the basis of these findings, these hydroxy 4-phenyl coumarins may be considered as potential therapeutic candidates for pathological conditions characterized by free radical overproduction. PMID:24602768

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Copper complex of (substituted... Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt... significant new uses subject to reporting. (1) The chemical substances identified generically as...

  10. 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...

  11. 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...

  12. 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...

  13. 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...

  14. 1-(2,6-Diisopropyl­phen­oxy)-4-phenyl­phthalazine

    PubMed Central

    Tong, Bihai; Mei, Qunying

    2012-01-01

    In the title mol­ecule, C26H26N2O, the phenyl and phen­oxy 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 inter­actions. PMID:22905005

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

    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 § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical...

  16. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical...

  17. 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. PMID:25504838

  18. Monitoring Amyelois transitella Males and Females with Phenyl Propionate Traps in Almonds and Pistachios

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Attractants that lure both sexes and both mated and unmated females have been used to monitor the effect of mating disruption on the mating status and relative abundance of lepidopteran females. For the navel orangeworm, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), phenyl propionate attra...

  19. 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)

  20. Effect of substituents at phenyl group of 7,7'-dioxo-9,9'-epoxylignane on antifungal activity.

    PubMed

    Nishiwaki, Hisashi; Ouchi, Maya; Matsugi, Junko; Akiyama, Koichi; Sugahara, Takuya; Kishida, Taro; Yamauchi, Satoshi

    2012-11-01

    Using 21 newly synthesized 7,7'-dioxo-9,9'-epoxylignane derivatives having a modified 7-phenyl group, we examined the relationship between their structure and antifungal activity against plant pathogens such as Bipolaris oryzae to determine the effects of various substituents on the antifungal activity. Compared with the lead compound having a 4-OH-3-CH(3)O-phenyl moiety, several analogs showed higher antifungal activity against B. oryzae, including the compound having an unsubstituted phenyl group and those having either of the following phenyl substituents: 2-OH, 4-CH(3)O, 4-C(2)H(5)O, 4-n-C(3)H(7)O, 4-n-C(4)H(9)O, 4-CF(3)O, 4-C(2)H(5), or 4-Cl. On the other hand, the activity of compounds having a branched substituent, such as 4-i-C(3)H(7)O or 4-i-C(3)H(7), on the 7-phenyl group or a multi-substituted phenyl group was equipotent or inferior to that of the lead compound. These results as well as correlations between the antifungal activity of the test compounds and the physicochemical parameters of the varied substituents suggest that the position of substitution on the 7-phenyl group and the incorporation of substituents with optimal physicochemical properties are important for exerting the antifungal activity. PMID:23017887

  1. Stereoisomers of 42-hydroxy palytoxin from Hawaiian Palythoa toxica and P. tuberculosa: stereostructure elucidation, detection, and biological activities.

    PubMed

    Ciminiello, Patrizia; Dell'Aversano, Carmela; Dello Iacovo, Emma; Forino, Martino; Tartaglione, Luciana; Pelin, Marco; Sosa, Silvio; Tubaro, Aurelia; Chaloin, O; Poli, Mark; Bignami, Gary

    2014-02-28

    Palytoxin ranks among the most potent marine biotoxins. Its lethality was well known to native Hawaiians that used to smear a "moss" containing the toxin on their spears to cause instant death to their victims. Human intoxications due to exposure to palytoxin and to its many congeners have been reported worldwide. Currently, palytoxins constitute the main threat to public health across the Mediterranean Sea. In the present work we report on the isolation and stereostructural determination of a new palytoxin analogue from a Hawaiian Palythoa tuberculosa sample. This new toxin is a stereoisomer of 42-hydroxypalytoxin isolated from Palythoa toxica. The whole absolute configuration of this latter toxin is also reported in the paper. Interestingly, the two 42-hydroxypalytoxins do not share the same biological activity. The stereoisomer from P. tuberculosa showed cytotoxicity toward skin HaCaT keratinocytes approximately 1 order of magnitude lower than that of 42-hydroxypalytoxin from P. toxica and about 2 orders of magnitude lower than that of palytoxin itself. This finding holds the prospect of interesting structure-activity relationship evaluations in the future. PMID:24512352

  2. Crystal structure of racemic cis-2-amino-1,2-di­phenyl­ethanol (ADE)

    PubMed Central

    Fujii, Isao

    2015-01-01

    In the title racemic compound, C14H15NO, the hy­droxy and amino groups form a bent tweezer-like motif towards the phenyl groups. In the crystal, enanti­omers aggregate with each other and are linked by O—H⋯N hydrogen bonds, forming chiral 21-helical columnar structures from C(5) chains along the b-axis direction. Left- and right-handed 21 helices are formed from (1S,2R)-2-amino-1,2-di­phenyl­ethanol and (1R,2S)-2-amino-1,2-di­phenyl­ethanol, respectively. PMID:26870424

  3. (2S,4aR,3S,8aR,9R,10R)-1,4-Diallyl-2,3-diphenyl­perhydro­quinoxaline

    PubMed Central

    Chen, Fang; Ye, Heng-Yun

    2008-01-01

    In the title compound, C26H32N2, the cyclo­hexane and piperazine rings each adopt a chair conformation. Both phenyl rings and the two propen-3-yl residues are in equatorial positions. There are no C—H⋯N hydrogen bonds nor π–π inter­actions between the aromatic rings. The absolute configuration was assigned with reference to the starting material. PMID:21202389

  4. Long-term exposure of HIV type 1-infected cell cultures to combinations of the novel quinoxaline GW420867X with lamivudine, abacavir, and a variety of nonnucleoside reverse transcriptase inhibitors.

    PubMed

    Balzarini, J; De Clercq, E; Carbonez, A; Burt, V; Kleim, J P

    2000-04-10

    The novel quinoxaline GW420867X has been combined with a variety of nucleoside reverse transcriptase inhibitors (NRTIs) and nonnucleoside reverse transcriptase inhibitors (NNRTIs) in HIV-1(IIIB)-infected CEM cell cultures. Whereas the antiviral efficacy of combinations of GW420867X with the NRTIs lamivudine (3TC) and abacavir (ABC) proved additive when administered to HIV-1-infected cells in a short-term (4-day) infection experiment, combination of GW420867X with the NRTIs 3TC and ABC resulted in a marked delay of virus breakthrough compared with the single drugs alone in a long-term (2-month) infection experiment. Delay of virus breakthrough was less pronounced for combinations of GW420867X with the NNRTIs. Combination of GW420867X with the NRTIs and NNRTIs resulted in additive inhibitory effects on recombinant HIV-1 reverse transcriptase as evident from isobolograms. Lamivudine plus GW420867X selected for the 3TC-specific M184I mutation and a number of NNRTI-characteristic mutations (i.e., V106A, V108I, and Y188H). Abacavir plus GW420867X selected only for NNRTI-specific mutations (i.e., K101E, K103R, V106A, and Y181C), including the novel L100V mutation. Combination of GW420867X with five different NNRTIs selected solely for NNRTI-specific mutations, and also for the L100V mutation in the combined presence of efavirenz, nevirapine, or emivirine, respectively. Five single-, two double-, and two triple-mutated HIV-1 strains that emerged from this study were evaluated for their sensitivity/resistance to AZT, lamivudine, and seven different NNRTIs. In all cases, efavirenz, GW420867X, and UC-781 retained pronounced antiviral potency. Our data suggest that combinations of GW420867X with 3TC, ABC, and NNRTIs (e.g., efavirenz) would be worth pursuing as therapeutic modalities against HIV-1 infections. PMID:10777142

  5. High risk of adrenal toxicity of N1-desoxy quinoxaline 1,4-dioxide derivatives and the protection of oligomeric proanthocyanidins (OPC) in the inhibition of the expression of aldosterone synthetase in H295R cells.

    PubMed

    Wang, Xu; Yang, Chunhui; Ihsan, Awais; Luo, Xun; Guo, Pu; Cheng, Guyue; Dai, Menghong; Chen, Dongmei; Liu, Zhenli; Yuan, Zonghui

    2016-02-01

    Quinoxaline 1,4-dioxide derivatives (QdNOs) with a wide range of biological activities are used in animal husbandry worldwide. It was found that QdNOs significantly inhibited the gene expression of CYP11B1 and CYP11B2, the key aldosterone synthases, and thus reduced aldosterone levels. However, whether the metabolites of QdNOs have potential adrenal toxicity and the role of oxidative stress in the adrenal toxicity of QdNOs remains unclear. The relatively new QdNOs, cyadox (CYA), mequindox (MEQ), quinocetone (QCT) and their metabolites, were selected for elucidation of their toxic mechanisms in H295R cells. Interestingly, the results showed that the main toxic metabolites of QCT, MEQ, and CYA were their N1-desoxy metabolites, which were more harmful than other metabolites and evoked dose and time-dependent cell damage on adrenal cells and inhibited aldosterone production. Gene and protein expression of CYP11B1 and CYP11B2 and mRNA expression of transcription factors, such as NURR1, NGFIB, CREB, SF-1, and ATF-1, were down regulated by N1-desoxy QdNOs. The natural inhibitors of oxidant stress, oligomeric proanthocyanidins (OPC), could upregulate the expression of diverse transcription factors, including CYP11B1 and CYP11B2, and elevated aldosterone levels to reduce adrenal toxicity. This study demonstrated for the first time that N1-desoxy QdNOs have the potential to be the major toxic metabolites in adrenal toxicity, which may shed new light on the adrenal toxicity of these fascinating compounds and help to provide a basic foundation for the formulation of safety controls for animal products and the design of new QdNOs with less harmful effects. PMID:26802905

  6. Non-N-methyl-D-aspartate (NMDA) receptor antagonist 1,2,3, 4-tetrahydro-6-nitro-2,3-dioxo-benzo(f)quinoxaline-7-sulphonamide (NBQX) decreases functional disorders in cytotoxic brain oedema.

    PubMed

    Häntzschel, A; Andreas, K

    2000-01-01

    N-methyl-D-aspartate (NMDA) and non-NMDA receptors were found to be involved in development of functional disorders caused by hexachlorophene. In order to specify the role of glutamate receptors we studied the protective effects of the selective antagonist of the kainate/(+/-)-alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptor/channel 1,2,3,4-tetrahydro-6-nitro-2, 3-dioxo-benzo[f]quinoxaline-7-sulphonamide disodium (NBQX) and of the non-competitive NMDA receptor antagonist ifenprodil tartrate on coordinative motor behaviour of adult male Wistar rats as assessed in a simple 'ladder-test'. Neurotoxic injury of the cerebrum after hexachlorophene administration and putative amelioration after treatment with test substances was demonstrated histologically. Hexachlorophene-induced motor disturbance remitted spontaneously when stopping the noxis, but remittance occurred significantly earlier when NBQX [0.45 and 0.6 mg/kg intraperitoneal (i.p.)] was applied as well. Ifenprodil (0.15 to 1.2 mg/kg) did not improve the motor function. Vacuolation of white matter of the whole cerebrum was observed after 3 weeks of treatment with hexachlorophene. These morphological alterations caused by hexachlorophene treatment [central nervous system (CNS) vacuolation] spontaneously revert only after 5-6 weeks. The 5-day duration with test substances was too short for remission of vacuolation which thus may not apply to the situation after treatment with glutamate antagonists, despite improvement of motor function. The results suggest that kainate/AMPA receptor channels are at least partially involved in the mechanism of brain damage induced by hexachlorophene, however, the polyamine binding site of the NMDA receptor evidently is not involved. PMID:10663390

  7. Phenyl-Modified Carbon Nitride Quantum Dots with Distinct Photoluminescence Behavior.

    PubMed

    Cui, Qianling; Xu, Jingsan; Wang, Xiaoyu; Li, Lidong; Antonietti, Markus; Shalom, Menny

    2016-03-01

    A novel type of quantum dot (Ph-CN) is manufactured from graphitic carbon nitride by "lining" the carbon nitride structure with phenyl groups through supramolecular preorganization. This approach requires no chemical etching or hydrothermal treatments like other competing nanoparticle syntheses and is easy and safe to use. The Ph-CN nanoparticles exhibit bright, tunable fluorescence, with a high quantum yield of 48.4 % in aqueous colloidal suspensions. Interestingly, the observed Stokes shift of approximately 200 nm is higher than the maximum values reported for carbon nitride based fluorophores. The high quantum yield and the large Stokes shift are related to the structural surface organization of the phenyl groups, which affects the π-electron delocalization in the conjugated carbon nitride networks and induces colloidal stability. The remarkable performance of the Ph-CN nanoparticles in imaging is demonstrated by a simple incubation study with HeLa cells. PMID:26880237

  8. Formation of polycyclic aromatic hydrocarbons from bimolecular reactions of phenyl radicals at high temperatures.

    PubMed

    Constantinidis, P; Schmitt, H-C; Fischer, I; Yan, B; Rijs, A M

    2015-11-21

    The self-reaction of the phenyl radical is one of the key reactions in combustion chemistry. Here we study this reaction in a high-temperature flow reactor by IR/UV ion dip spectroscopy, using free electron laser radiation as mid-infrared source. We identified several major reaction products based on their infrared spectra, among them indene, 1,2-dihydronaphthalene, naphthalene, biphenyl and para-terphenyl. Due to the structural sensitivity of the method, the reaction products were identified isomer-selectively. The work shows that the formation of indene and naphthalene, which was previously considered to be evidence for the HACA (hydrogen abstraction C2H2 addition) mechanism in the formation of polycyclic aromatic hydrocarbons and soot can also be understood in a phenyl addition model. PMID:26457393

  9. Synthesis, characterization and fluorescence studies of novel bi-phenyl based acrylate and methacrylate

    NASA Astrophysics Data System (ADS)

    Baskar, R.; Subramanian, K.

    2011-09-01

    4-[(1 E)-3-(biphenyl-4-yl)buta-1,3-dien-1-yl]phenyl prop-2-enoate ( ACH) and 4-[(1 E)-3-(biphenyl-4-yl)buta-1,3-dien-1-yl]phenyl 2-methylprop-2-enoate ( MCH) was synthesized from biphenyl in three steps and their structures were confirmed by elemental analysis, IR, NMR ( 1H, 13C, DEPT135, 1H- 1H COSY, 1H- 13C HSQC and 1H- 13C HMBC) spectroscopic techniques. In this present study, various physicochemical characteristics we demonstrate solubility, color, absorbance and fluorescence property of novel biphenyl based acrylate and methacrylate measured in different solvents like benzene, dichloromethane, tetrahydrofuran, acetonitrile, dimethylsulfoxide and ethanol.

  10. 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.

  11. Perfluorophenyl-phenyl interactions in the crystallization and topochemical polymerization of triacetylene monomers.

    PubMed

    Xu, Rui; Schweizer, W Bernd; Frauenrath, Holger

    2009-09-14

    A series of symmetrically and unsymmetrically substituted octa-2,4,6-triyne-1,8-diol derivatives with benzoyl, 4-dodecyloxybenzoyl, as well as perfluorobenzoyl substituents were prepared and investigated with respect to their crystal structures and topochemical polymerizability. Single-crystal structures for several of these triacetylene monomers have been obtained and proved that the perfluorophenyl-phenyl interactions played a decisive role in the molecular packing. As a consequence of the geometric requirements imposed by the perfluorophenyl-phenyl interactions, packing parameters appropriate for a topochemical triacetylene polymerization in the sense of either a 1,6- or a 1,4-polyaddition along different crystallographic axes were observed in two cases, and UV irradiation led to successful polymerization. Raman as well as solid-state (13)C NMR spectra of the obtained polymers revealed that the polymerization had predominantly proceeded in the form of a 1,4-polyaddition. PMID:19637260

  12. Chemistry of enol ethers. LXXVII. Synthesis of acetals of phenyl-substituted glutaconaldehydes

    SciTech Connect

    Makin, S.M.; Kruglikova, R.I.; Lonina, N.N.

    1987-10-10

    The condensation of the acetals of acetophenone and acetaldehyde with enol ethers, as a result of which 2- and 3-phenyl-1,1,3-trialkoxybutanes were obtained, was studied. The acid hydrolysis of the products leads to the formation of 2- and 3-phenylbutenals, from which 2- and 3-phenyl-1-trimethylsilyloxy-1,3-butadienes were obtained by the action of trimethylchlorosilane and triethylamine. The reaction of the silyloxydienes with ethyl orthoformate in the presence of zinc chloride as catalyst gave the monoacetals of ..cap alpha..- and ..beta..-phenylglutaconaldehydes, which were converted into the corresponding bisacetals by the further action of the orthoformate. The /sup 1/H NMR spectra of 50% solutions of the substances being analyzed in deuterochloroform or deuteroacetone were recorded on Bruker WH-90 and Bruker WM-250 instruments at 90 and 250 MHz respectively.

  13. 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. PMID:18947854

  14. Amidation inhibitors 4-phenyl-3-butenoic acid and 5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid methyl ester are novel HDAC inhibitors with anti-tumorigenic properties.

    PubMed

    Ali, Amna; Burns, Timothy J; Lucrezi, Jacob D; May, Sheldon W; Green, George R; Matesic, Diane F

    2015-08-01

    4-Phenyl-3-butenoic acid (PBA) is an inhibitor of peptidylglycine alpha-amidating monooxygenase with anti-inflammatory properties that has been shown to inhibit the growth of ras-mutated epithelial and human lung carcinoma cells. In this report, we show that PBA also increases the acetylation levels of selected histone subtypes in a dose and time dependent manner, an effect that is attributable to the inhibition of histone deacetylase (HDAC) enzymes. Comparison studies with the known HDAC inhibitor suberoylanilide hydroxamic acid (SAHA) using high resolution two-dimensional polyacrylamide gels and Western analysis provide evidence that PBA acts as an HDAC inhibitor within cells. PBA and a more potent amidation inhibitor, 5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid methyl ester (AOPHA-Me), inhibit HDAC enzymes in vitro at micromolar concentrations, with IC50 values approximately 30 fold lower for AOPHA-Me than PBA for selected HDAC isoforms. Overall, these results indicate that PBA and AOPHA-Me are novel anti-tumorigenic HDAC inhibitors. PMID:26065689

  15. Third order nonlinear optical studies of 1-(4-chloro phenyl)-3-(4-dimethylamino phenyl) prop-2-en-1-one

    NASA Astrophysics Data System (ADS)

    Janardhana, K.; Ravindrachary, V.; Rajesh Kumar, P. C.; Yogisha; Ismayil

    2013-04-01

    A chalcone, 1-(4-chloro phenyl)-3-(4-dimethylamino phenyl) prop-2-en-1-one, abbreviated as CDAC was synthesized by the Claisen-Schmidt condensation method and single crystals were grown by the slow evaporation technique at ambient temperature. The structural confirmation was done using 1H-NMR, FT-IR, powder XRD and single crystal XRD studies. The crystal crystallizes in the monoclinic space group P21/c with a=33.082(3) Å, b=14.4722(13) Å, c=6.0799(5) Å, α=90°, β=92.030(4)°, γ=90° and Z=8. The high temperature DSC shows a phase transition at temperature 141.53 °C that corresponds to the melting point of the crystal. This is confirmed in DTA study which shows an endothermic dip corresponding to this melting point. The optical studies were made with UV-visible and Z-scan techniques. The nonlinear absorption and nonlinear refraction coefficients of the sample were obtained by performing the Z-scan experimental measurements. The real and imaginary parts of third-order bulk susceptibility χ(3) were evaluated. The coefficient of nonlinear refraction (γ) of the compound is found to be negative as revealed by the signature of closed aperture data.

  16. Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone.

    PubMed

    Nambo, Masakazu; Crudden, Cathleen M

    2014-01-13

    Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals. PMID:24307286

  17. Designing Higher Surface Area Metal-Organic Frameworks: Are Triple Bonds Better than Phenyls?

    SciTech Connect

    Farha, O. K.; Wilmer, C. E.; Eryazici, I.; Hauser, B. G.; Parilla, P. A.; Oneill, K.; Sarjeant, A. A.; Nguyen, S. T.; Snurr, R. Q.; Hupp, J. T.

    2012-06-20

    We have synthesized, characterized, and computationally validated the high Brunauer-Emmett-Teller surface area and hydrogen uptake of a new, noncatenating metal-organic framework (MOF) material, NU-111. Our results imply that replacing the phenyl spacers of organic linkers with triple-bond spacers is an effective strategy for boosting molecule-accessible gravimetric surface areas of MOFs and related high-porosity materials.

  18. 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.

  19. Phenyl 3-meth­oxy-4-phen­oxy­benzoate

    PubMed Central

    Zhou, Jing; Zheng, Shuai; Chen, Gang; Wang, Wenjing; Du, Zhenting

    2011-01-01

    In the title mol­ecule, C20H16O4, the two outermost phenyl rings form dihedral angles of 79.80 (7) and 69.35 (7)° with the central benzene ring. In the crystal structure, weak inter­molecular C—H⋯O inter­actions link the mol­ecules into ribbons propagating along [10]. PMID:22058990

  20. 1-Phenyl-3-methyl-4-benzoyl-pyrazolone-5. A promising extractant for plutonium

    SciTech Connect

    Manchanda, V.K.; Mohapatra, P.K. )

    1994-05-01

    Pyrazolones and isoxazolones have been found to be promising extractants for metal ions, particularly from strong acidic media and in the presence of complexing anions. Extraction constants (log k[sub ex]) in toluene medium at 25[degree]C for PuX[sub 4] species, where X = 1-phenyl-3-methyl-4-acetyl-pyrazolone-5 (HPMAP), 1-phenyl-3-methyl-4-benzoyl-pyrazolone-5 (HPMBP), or 1-phenyl-3-methyl-4-(3:5-dinitro-benzoyl)pyrazolone-5 (HPMDP), are determined as 11.35 [+-] 0.04, 12.89 [+-] 0.03, and 12.73 [+-] 0.02, respectively. These values are comparable to the corresponding value for 3-phenyl-4-benzoyl-5-isoxazolone (HPBI) and several order of magnitude larger than that for 2-thenoyltrifluoroacetone (HTTA). A systematic study is carried out to investigate the extraction behavior of these [beta]-diketones toward plutonium present in the analytical waste solution obtained during the determination of uranium in a (U, Pu) fuel sample by the Davies Gray method. Whereas 0.3 M HPMBP extracts > 85% of the plutonium present in a single step, maximum extraction observed with other reagents is [much lt] 0.1% HTTA, 0.3% HPMAP, and 2.5% HPBI. The extraction of plutonium increases with different diluents in the order n-dodecane < n-hexane < CHCl[sub 3] < CCl[sub 4] < toluene. Extracted plutonium is quantitatively stripped with either 10 M HNO[sub 3] or 1:1 HCl + 0.1 M hydroquinone. 19 refs., 5 figs., 8 tabs.

  1. Cholest-5-en-3β-yl N-phenyl­carbamate

    PubMed Central

    Graia, Mohsen; Raza Murad, Ghalib; Krimi Ammar, Mehrzia; Mehdi, Sayed Hasan; Hashim, Rokiah

    2009-01-01

    In the title compound, C34H51NO2, the dihedral angle between the planes of the phenyl ring and the carbonyl group is 9.30 (2)°. No significant inter­molecular inter­actions are observed in the crystal structure. The C5H11 fragment is disordered over two positions with site occupancies of 0.611 (6) and 0.389 (6). PMID:21578937

  2. [Pharmacological characteristics of a new phenyl analog of piracetam--4-phenylpiracetam].

    PubMed

    Bobkov, Iu G; Morozov, I S; Glozman, O M; Nerobkova, L N; Zhmurenko, L A

    1983-04-01

    The central neurotropic effects of 4-phenylpyracetam, a new phenyl analog of pyracetam, were studied and compared with the effects of pyracetam, morpholene and 4-phenylpyrrolidone. 4-Phenylpyracetam was found to activate the operant behavior more powerfully, to remove psychodepressant effects of diazepam, to inhibit post-rotational nystagmus, and to prevent the development of retrograde amnesia. Unlike pyracetam, 4-phenylpyracetam exhibits a specific anticonvulsant action. When given in high doses, the compound under study produces psychodepressant effects. PMID:6403074

  3. 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.

  4. 5-(4-Methyl­phen­yl)-3-phenyl­cyclo­hex-2-en-1-one

    PubMed Central

    Mohamed, Shaaban K.; Akkurt, Mehmet; Abdelhamid, Antar A; Singh, Kuldip; Allah, Omyma A. A. Abd

    2012-01-01

    In the title compound, C19H18O, the cyclo­hexene ring has an envelope conformation with the methine C atom on the flap. The phenyl and methyl­phenyl rings form a dihedral angle of 85.93 (11)°. The crystal packing is consolidated by van der Waals forces and weak C—H⋯π inter­actions. PMID:22798829

  5. Linear free energy relationship rate constants and basicities of N-substituted phenyl glycines in positronium-glycine complex formation

    NASA Astrophysics Data System (ADS)

    Chen, Rongti; Liang, Jiachang; Du, Youming; Cao, Chun; Yin, Dinzhen; Wang, Shuying; Zhang, Tianbao

    1987-06-01

    Complex formation between positronium and glycine derivatives in solution is discussed and the complex reaction rate constants obtained by means of a positron annihilation lifetime spectrometer with BaF 2 detectors. Rate constants mainly depend on the conjugation effect at the benzene ring and the induction effect of the substituents at the phenyl. There is a linear free energy relationship between rate constants and basicities of N-substituted phenyl glycines in orthopositronium-glycine complex formation.

  6. 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. PMID:21108142

  7. Computational Study of Bond Dissociation Enthalpies for Lignin Model Compounds. Substituent Effects in Phenethyl Phenyl Ethers

    SciTech Connect

    Beste, Ariana; Buchanan III, A C

    2009-01-01

    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 (PhCH2CH2OPh, PPE) is the simplest example representing the dominant -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.

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

    PubMed

    Beste, Ariana; Buchanan, A C

    2009-04-01

    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. PMID:19260664

  9. Aminolysis of phenyl N-phenylcarbamate via an isocyanate intermediate: theory and experiment.

    PubMed

    Ilieva, Sonia; Nalbantova, Didi; Hadjieva, Boriana; Galabov, Boris

    2013-07-01

    A comprehensive examination of the mechanism of the uncatalyzed and base-catalyzed aminolysis of phenyl N-phenylcarbamate by theoretical quantum mechanical methods at M06-2X/6-311+G(2d,2p) and B3LYP-D3/6-31G(d,p) levels, combined with an IR spectroscopic study of the reaction, was carried out. Three alternative reaction channels were theoretically characterized: concerted, stepwise via a tetrahedral intermediate, and stepwise involving an isocyanate intermediate. In contrast to dominating views, the theoretical results revealed that the reaction pathway through the isocyanate intermediate (E1cB) is energetically favored. These conclusions were supported by an IR spectroscopic investigation of the interactions of phenyl N-phenylcarbamate with several amines possessing varying basicities and nucleophilicities: n-butylamine, diethylamine, triethylamine, N-methylpyrrolidine, and trimethylamine. The reactivity of substituted phenyl N-phenylcarbamates in the aminolysis reaction was rationalized using theoretical and experimental reactivity indexes: electrostatic potential at nuclei (EPN), Hirshfeld and NBO atomic charges, and Hammett constants. The obtained quantitative relationships between these property descriptors and experimental kinetic constants reported in the literature emphasize the usefulness of theoretical parameters (EPN, atomic charges) in characterizing chemical reactivity. PMID:23734590

  10. 2-[3-(4-Bromo­phenyl)-5-(4-fluoro­phenyl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

    PubMed Central

    Abdel-Wahab, Bakr F.; Mohamed, Hanan A.; Ng, Seik Weng; Tiekink, Edward R. T.

    2013-01-01

    In the title compound, C24H17BrFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluoro­benzene ring substituents [dihedral angle = 77.9 (3)°] being very approximately coplanar [dihedral angle with the 2-thienyl ring = 19.4 (3)° and with the bromo­benzene ring = 20.3 (3)°; dihedral angle between the 2-thienyl and attached phenyl ring = 11.0 (4)°], so that the mol­ecule has a T-shape. In the crystal, supra­molecular chains along the b-axis direction are sustained by C—H⋯S and C—Br⋯π inter­actions. PMID:23723887

  11. Phenyl ring dynamics of the insulin fragment Gly-Phe-Phe(B23 B25) by solid state deuterium NMR

    NASA Astrophysics Data System (ADS)

    Naito, A.; Iizuka, T.; Tuzi, S.; Price, W. S.; Hayamizu, K.; Saitô, H.

    1995-08-01

    The phenyl ring dynamics of the insulin fragment Gly-Phe-Phe(B23-B25) were investigated using solid state deuterium NMR spectroscopy. It was found that the phenyl rings of the two phenylalanine residues Phe 2 and Phe 3 were rigid even up to 100°C both for the Gly-[ring- d5]Phe-Phe and the Gly-The-[ring- d5]Phe in the hydrated crystals. When the temperature was raised to 120°C, the hydrated water evaporated from the crystal, resulting in the onset of the flipping motion of the phenyl rings. Spectral simulation of the deuterium NMR spectra was performed to better characterize the motion of the phenyl rings in the peptides. It was found that the phenyl ring motion of the fragments is consistent with a 180° flip about the C βC γ bonds. The phenyl ring of Ph 2 of Gly-[ d5]Phe-Phe was more mobile than that of Phe 3 of Gly-Phe-[ d5]Phe when the tripeptide crystal was in the dehydrated state. The Phe-Phe residues in the tripeptide were quite rigid when the hydrophobic interaction around the Phe-Phe moiety was strong.

  12. Quantification of the carcinogens 2-amino-3,8-dimethyl- and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in food using a combined assay based on gas chromatography-negative ion mass spectrometry.

    PubMed

    Murray, S; Lynch, A M; Knize, M G; Gooderham, M J

    1993-07-01

    A gas chromatographic-mass spectrometric assay has been developed for the measurement of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (DiMeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in food. Stable isotope-labelled analogues of MeIQx and PhIP are used as internal standards and the synthesis of deuterated PhIP is described. The mass spectrometer is operated in the electron-capture negative ion chemical ionisation mode and the amines are chromatographed as their di-3,5-bistrifluoromethylbenzyl derivatives. All three compounds can be measured in a single chromatographic run and detection limits of 0.05, 0.1 and 0.2 ng/g for MeIQx, DiMeIQx and PhIP, respectively, in food are obtained. Various home-cooked and commercially prepared foodstuffs were analysed with this assay and several were found to contain measurable amounts of one or more of the three amines. These results are presented and discussed. PMID:8376502

  13. Tetra-kis(μ-3,4-dimeth-oxy-phenyl-acetato)-bis-[(3,4-dimeth-oxy-phenyl-acetato)(1,10-phenanthroline)holmium(III)].

    PubMed

    Zhao, Guo-Liang; Liu, Jia-Lu; Liu, Jian-Feng

    2010-01-01

    In the centrosymmetric title compound, [Ho(2)(C(10)H(11)O(4))(6)(C(12)H(8)N(2))(2)], the Ho(III) atom is nine-coordinated by seven O atoms from the 3,4-dimeth-oxy-phenyl-acetate (L) anions and two N atoms from a 1,10-phenanthroline (phen) mol-ecule. The L ligands are coordinated to the Ho(III) ions in three modes: chelating, bridging and bridging-tridentate. Intra-molecular C-H⋯O inter-actions occur. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions and weak aromatic π-π inter-actions between phen mol-ecules and the aromatic rings of the L ligands [centroid-centroid distance = 3.821 (2) Å]. PMID:21587417

  14. Crystal structures of (E)-3-(furan-2-yl)-2-phenyl-N-tosyl-acryl-amide and (E)-3-phenyl-2-(m-tol-yl)-N-tosyl-acryl-amide.

    PubMed

    Cheng, Dong; Meng, Xiangzhen; Sheng, Zeyuan; Wang, Shuangming; Duan, Yuanyuan; Li, Ziqian

    2016-06-01

    In the title N-tosyl-acryl-amide compounds, C20H17NO4S, (I), and C23H21NO3S, (II), the conformation about the C=C bond is E. The acryl-amide groups, [-NH-C(=O)-C=C-], are almost planar, with the N-C-C=C torsion angle being -170.18 (14)° in (I) and -168.01 (17)° in (II). In (I), the furan, phenyl and 4-methyl-benzene rings are inclined to the acryl-amide mean plane by 26.47 (11), 69.01 (8) and 82.49 (9)°, respectively. In (II), the phenyl, 3-methyl-benzene and 4-methyl-benzene rings are inclined to the acryl-amide mean plane by 11.61 (10), 78.44 (10) and 78.24 (10)°, respectively. There is an intra-molecular C-H⋯π inter-action present in compound (II). In the crystals of both compounds, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. In (I), the dimers are reinforced by C-H⋯O hydrogen bonds and linked by C-H⋯π inter-actions, forming chains along [011]. In the crystal of (II), the dimers are linked via C-H⋯O hydrogen bonds, forming chains along [100]. The chains are further linked by C-H⋯π inter-actions, forming layers parallel to (010). PMID:27308045

  15. 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

    ...-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium salt. 721.4040 Section 721.4040 Protection of...-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium salt. (a) Chemical..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  16. 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

    ...-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium salt. 721.4040 Section 721.4040 Protection of...-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium salt. (a) Chemical..., polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetramethyl butyl)phenyl ether, sodium salt (P-90-1565)...

  17. 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. PMID:25354358

  18. Identification of halogen atoms in scanning tunneling microscopy images of substituted phenyl octadecyl ethers.

    PubMed

    Lee, H S; Iyengar, S; Musselman, I H

    2001-11-15

    A homologous series of para-substituted phenyl octadecyl ethers (X-POEs, where X = H, Cl, Br, I) was prepared using the Williamson ether synthesis and characterized by 1H NMR and GC/MS. Scanning tunneling microscopy images acquired from these ethers revealed a bias-dependent contrast corresponding to electron density contours of various X-POE molecular orbitals. Images reflecting the electron density contour of the highest occupied molecular orbital exhibited four bright spots--one for the halogen atom, two representing the pair of lobes of the phenyl ring, and one for the oxygen/alpha-carbon atoms. For each X-POE, the intensities (Zmax) of the spots for the halogen atom and the lobe of the phenyl ring closest to the halogen were measured and their ratio was calculated (Cl-POE 0.49 +/- 0.06; Br-POE 0.59 +/- 0.06; I-POE 0.75 +/- 0.07). Analysis of variance at the 95% confidence level revealed that the intensity ratios were consistent from molecule to molecule, image to image, and day to day. According to the Student t-test, the average Zmax ratios for Cl-POE, Br-POE, and I-POE are different at the 95% confidence level. In addition, they follow a trend that corresponds favorably with that of the atomic radii of the halogens. The probability of classifying a single X-POE molecule as Cl-POE, Br-POE, or I-POE is variable and depends on the magnitude of the Zmax ratio. PMID:11816584

  19. 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.

  20. A theoretical study of the relaxation of a phenyl group chemisorbed to an RDX freestanding thin film.

    PubMed

    Pereverzev, Andrey; Sewell, Thomas D

    2016-08-01

    Energy relaxation from an excited phenyl group chemisorbed to the surface of a crystalline thin film of α-1,3,5-trinitro-1,3,5-triazacyclohexane (α-RDX) at 298 K and 1 atm is simulated using molecular dynamics. Two schemes are used to excite the phenyl group. In the first scheme, the excitation energy is added instantaneously as kinetic energy by rescaling momenta of the 11 atoms in the phenyl group. In the second scheme, the phenyl group is equilibrated at a higher temperature in the presence of static RDX geometries representative of the 298 K thin film. An analytical model based on ballistic phonon transport that requires only the harmonic part of the total Hamiltonian and includes no adjustable parameters is shown to predict, essentially quantitatively, the short-time dynamics of the kinetic energy relaxation (∼200 fs). The dynamics of the phenyl group for times longer than about 6 ps follows exponential decay and agrees qualitatively with the dynamics described by a master equation. Long-time heat propagation within the bulk of the crystal film is consistent with the heat equation. PMID:27497561

  1. A theoretical study of the relaxation of a phenyl group chemisorbed to an RDX freestanding thin film

    NASA Astrophysics Data System (ADS)

    Pereverzev, Andrey; Sewell, Thomas D.

    2016-08-01

    Energy relaxation from an excited phenyl group chemisorbed to the surface of a crystalline thin film of α-1,3,5-trinitro-1,3,5-triazacyclohexane (α-RDX) at 298 K and 1 atm is simulated using molecular dynamics. Two schemes are used to excite the phenyl group. In the first scheme, the excitation energy is added instantaneously as kinetic energy by rescaling momenta of the 11 atoms in the phenyl group. In the second scheme, the phenyl group is equilibrated at a higher temperature in the presence of static RDX geometries representative of the 298 K thin film. An analytical model based on ballistic phonon transport that requires only the harmonic part of the total Hamiltonian and includes no adjustable parameters is shown to predict, essentially quantitatively, the short-time dynamics of the kinetic energy relaxation (˜200 fs). The dynamics of the phenyl group for times longer than about 6 ps follows exponential decay and agrees qualitatively with the dynamics described by a master equation. Long-time heat propagation within the bulk of the crystal film is consistent with the heat equation.

  2. 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.

  3. A new phenyl glycoside from the aerial parts of Equisetum hyemale.

    PubMed

    Jin, Mei; Zhang, Changhao; Zheng, Tie; Yao, Dalei; Shen, Le; Luo, Jie; Jiang, Zhe; Ma, Juan; Jin, Xue-Jun; Cui, Jiongmo; Lee, Jung Joon; Li, Gao

    2014-01-01

    A new phenyl glycoside, 2-(sophorosyl)-1-(4-hydroxyphenyl)ethanone (9), was isolated from the ethanolic extract of the aerial parts of Equisetum hyemale L., together with eight known compounds (1-8). The structures of these compounds were elucidated using a combination of spectroscopic analyses and chemical method. Of these nine compounds, 4 and 7 showed hepatoprotective effects towards tacrine-induced cytotoxicity in Hep 3B cells with EC50 values of 42.7 ± 1.5 and 132.6 ± 2.8 μM, respectively. PMID:25117054

  4. Flavonoids, cinnamic acid and phenyl propanoid from aerial parts of Scrophularia striata.

    PubMed

    Monsef-Esfahani, Hamid R; Hajiaghaee, Reza; Shahverdi, Ahmad R; Khorramizadeh, Mohammad R; Amini, Mohsen

    2010-03-01

    No phytochemical investigation regarding Scrophularia striata Boiss. (Scrophulariaceae) has been performed, although several reports about other Scrophularia species have been published. The inhibitory effects of aerial parts of S. striata on matrix metalloproteinase expression elaborate a new approach to treat variety of malignant and inflammatory disorders. Five known compounds, including cinnamic acid, three flavonoids (quercetine, isorhamnetin-3-O-rutinoside and nepitrin) and one phenyl propanoid glycoside (acteoside 1) were isolated from S. striata Boiss. by chromatographic techniques and the structures of compounds were characterized by spectroscopic methods. This is the first report regarding the isolation of these compounds from S. striata. PMID:20645822

  5. Synthesis and Luminescent Properties of Poly(9-(3-vinyl-phenyl)-phenanthrene).

    PubMed

    Yang, Garam; Lee, Hayoon; Lee, Suji; Jung, Hyocheol; Shin, Hwangyu; Lee, Jaehyun; Park, Jongwook

    2016-02-01

    Recently, interest of polymer light-emitting diode (PLED) fabricated from conjugated polymer has augmented because PLED has advantage property that is well-suited to flexible lighting and solution processed device. In this presentation, we suggest a new polymer host based on phenanthrene, poly(9-(3-Vinyl-phenyl)-phenanthrene) (PVPP). It can be easily synthesized through simple synthetic methods which are Suzuki and Wittig reactions. PVPP film can be obtained from spin coating with solution used by common solvent. It exhibited PL maximum value of 381 nm and broad PL spectrum. Energy transfer smoothly occurred when the three dopants for green, red and yellow were used in PVPP. PMID:27433663

  6. Design, Synthesis and Bioactivity of N-Glycosyl-N′-(5-substituted phenyl-2-furoyl) Hydrazide Derivatives

    PubMed Central

    Cui, Zining; Su, Hang; Jiang, Jiazhen; Yang, Xinling; Nishida, Yoshihiro

    2014-01-01

    Condensation products of 5-substituted phenyl-2-furoyl hydrazide with different monosaccharides d-glucose, d-galactose,d-mannose, d-fucose and d-arabinose were prepared. The anomerization and cyclic-acyclic isomers were investigated by 1H NMR spectroscopy. The results showed that, except for the d-glucose derivatives, which were in the presence of β-anomeric forms, all derivatives were in an acyclic Schiff base form. Their antifungal and antitumor activities were studied. The bioassay results indicated that some title compounds showed superior effects over the commercial positive controls. PMID:24756095

  7. S-Phenyl 4-meth­oxy­benzothio­ate

    PubMed Central

    El-Azab, Adel S.; Abdel-Aziz, Alaa A.-M.; El-Subbagh, Hussein I.; Chantrapromma, Suchada; Fun, Hoong-Kun

    2012-01-01

    In the mol­ecule of the title thio­ester, C14H12O2S, the dihedral angle between the phenyl and benzene rings is 71.8 (3)°. The meth­oxy group is essentially coplanar with the benezene ring to which it is bonded, with an r.m.s. deviation of 0.0065 (5) Å for the non-H atoms involved. In the crystal, weak C—H⋯π inter­actions are present. PMID:22589939

  8. 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.

  9. 2-Methyl-1-phenyl­sulfonyl-1H-indole-3-carbaldehyde

    PubMed Central

    Ramathilagam, C.; Saravanan, V.; Mohanakrishnan, A. K.; Umarani, P. R.; Manivannan, V.

    2011-01-01

    In the title compound, C16H13NO3S, the sulfonyl-bound phenyl ring forms a dihedral angle of 84.17 (6)° with the indole ring system. An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure exhibits weak inter­molecular C—H⋯O hydrogen bonds and π–π inter­actions between the five- and six-membered rings of the indole group [centroid–centroid distance = 3.6871 (9) Å]. PMID:22058759

  10. Coalescence of 3-phenyl-propynenitrile on Cu(111) into interlocking pinwheel chains.

    PubMed

    Luo, Miaomiao; Lu, Wenhao; Kim, Daeho; Chu, Eric; Wyrick, Jon; Holzke, Connor; Salib, Daniel; Cohen, Kamelia D; Cheng, Zhihai; Sun, Dezheng; Zhu, Yeming; Einstein, T L; Bartels, Ludwig

    2011-10-01

    3-phenyl-propynenitrile (PPN) adsorbs on Cu(111) in a hexagonal network of molecular trimers formed through intermolecular interaction of the cyano group of one molecule with the aromatic ring of its neighbor. Heptamers of trimers coalesce into interlocking pinwheel-shaped structures that, by percolating across islands of the original trimer coverage, create the appearance of gear chains. Density functional theory aids in identifying substrate stress associated with the chemisorption of PPN's acetylene group as the cause of this transition. PMID:21992333

  11. Negative ion mass spectra and structure of 4-substituted 1-phenyl-3-methyl-5-pyrazolones

    SciTech Connect

    Ermakov, A.I.; Sorokin, A.A.; Voronin, V.G.

    1986-06-01

    This is the first study of the electron capture dissociative resonance (ECDR) mass spectra of 4-substituted 1-phenyl-3-methyl-5-pyrazolones. The major features of the fragmentation of these compounds under ECDR conditions were found relative to their substituent properties. After loss of the methyl group from the nitrogen atom, the pyrazolone ring isomerizes to a pyrazole ring with localization of the negative charge on the oxygen atom of the carbonyl group. The intensity of the (M - CH/sub 3/) - fragment depends on the substituent properties.

  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. 9-Meth­oxy-5-phenyl­sulfonyl-5H-benzo[b]carbazole

    PubMed Central

    Chakkaravarthi, G.; Dhayalan, V.; Mohanakrishnan, A. K.; Manivannan, V.

    2008-01-01

    In the title compound, C23H17NO3S, the mean plane of the benzo[b]carbazole ring system makes a dihedral angle of 77.17 (4)° with the phenyl ring. The S atom is in a distorted tetra­hedral configuration. There are three intra­molecular C—H⋯O inter­actions forming five- and six-membered rings with graph-set motifs S(5) and S(6), respectively. PMID:21201699

  14. Bioactive 1,4-Dihydroxy-5-phenyl-2-pyridinone Alkaloids from Septoria pistaciarum

    PubMed Central

    Kumarihamy, Mallika; Fronczek, Frank R.; Ferreira, Daneel; Jacob, Melissa; Khan, Shabana I.; Nanayakkara, N.P. Dhammika

    2010-01-01

    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 analysis. Compound 1 exhibited moderate in vitro antiplasmodial (antimalarial) activity against chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum and cytotoxic activity to Vero cells. Compound 2 was moderately active against both methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus. PMID:20550123

  15. Crystal structure of 2-oxo-N′-phenyl-2H-chromene-3-carbohydrazide

    PubMed Central

    Mague, Joel T.; Mohamed, Shaaban K.; Akkurt, Mehmet; Younes, Sabry H. H.; Albayati, Mustafa R.

    2015-01-01

    In the title compound, C16H12N2O3, the 2H-chromene moiety is essentially planar, with an r.m.s. deviation of the nine constituent atoms from the mean plane of 0.0093 Å, and makes a dihedral angle of 76.84 (3)° with the pendant phenyl ring. An intra­molecular N—H⋯O hydrogen bond helps to determine the conformation of the side chain. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link the mol­ecules, forming [100] chains. PMID:26870466

  16. Sterically controlled azomethine ylide cycloaddition polymerization of phenyl-C61-butyric acid methyl ester.

    PubMed

    Stephen, Meera; Ramanitra, Hasina H; Santos Silva, Hugo; Dowland, Simon; Bégué, Didier; Genevičius, Kristijonas; Arlauskas, Kęstutis; Juška, Gytis; Morse, Graham E; Distler, Andreas; Hiorns, Roger C

    2016-05-01

    Phenyl-C61-butyric acid methyl ester (PCBM) is polymerized simply using a one-pot reaction to yield soluble, high molecular weight polymers. The sterically controlled azomethine ylide cycloaddition polymerization (SACAP) is demonstrated to be highly adaptable and yields polymers with probable Mn≈ 24 600 g mol(-1) and Mw≈ 73 800 g mol(-1). Products are metal-free and of possible benefit to organic and hybrid photovoltaics and electronics as they form thin films from solution and have raised LUMOs. The promising electronic properties of this new polymer are discussed. PMID:27066898

  17. Bis(trimethyl-phenyl-ammonium) tetra-bromidobis(4-chloro-phen-yl)stannate(IV).

    PubMed

    Lo, Kong Mun; Ng, Seik Weng

    2009-01-01

    The Sn(IV) atom in the title salt, [N(CH(3))(3)(C(6)H(5))](2)[SnBr(4)(C(6)H(4)Cl)(2)], exists in a distorted all-trans SnC(2)Br(4) octa-hedral geometry. The Sn(IV) atom lies on a center of inversion. Weak inter-molecular C-H⋯Br hydrogen bonding is observed between trimethyl-phenyl-ammonium cations and the Sn complex anion in the crystal structure. PMID:21578684

  18. 3,4-Di­methyl­phenyl quinoline-2-carboxyl­ate

    PubMed Central

    Fazal, E.; Kaur, Manpreet; Sudha, B. S.; Nagarajan, S.; Jasinski, Jerry P.

    2013-01-01

    In the title compound, C18H15NO2, the dihedral angle between the mean planes of the quinoline ring system and the phenyl ring is 48.1 (5)°. The mean plane of the carboxyl­ate group is twisted from the mean planes of the latter by 19.8 (8) and 64.9 (5)°, respectively. The crystal packing features weak C—H⋯O inter­actions, which form chains along [010]. PMID:24454268

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

    SciTech Connect

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

    2008-01-15

    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 A) 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.

  20. 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.

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

    PubMed

    Hsu, Liang-Yan; Rabitz, Herschel

    2012-11-01

    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. PMID:23215309

  2. The pure rotational spectrum of a Claisen rearrangement precursor Allyl Phenyl Ether using CP-FTMW spectroscopy

    NASA Astrophysics Data System (ADS)

    Grubbs, G. S.; Frank, Derek S.; Obenchain, Daniel A.; Cooke, S. A.; Novick, Stewart E.

    2016-06-01

    The pure rotational spectrum of a Claisen rearrangement precursor, Allyl Phenyl Ether (APE), has been measured on a chirped pulse Fourier transform microwave (CP-FTMW) spectrometer in the 8-14 GHz region. Rotational and centrifugal distortion constants for multiple conformations have been determined and are reported for the first time. This is the first study of a phenyl-containing ether where multiple conformers were experimentally observed all within their ground vibrational states. Quantum chemical calculations have been performed to isolate low energy geometries of APE and are implemented to aid in spectral assignment. Other structural parameters such as planar moments and inertial defects for the Allyl Phenyl Ether conformers are presented and compared to similar molecules.

  3. 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. PMID:26321725

  4. 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

    2016-06-01

    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. PMID:27139216

  5. Light induced controlled release of fragrances by Norrish type II photofragmentation of alkyl phenyl ketones.

    PubMed

    Levrand, Barbara; Herrmann, Andreas

    2002-11-01

    The use of alkyl phenyl ketones as delivery systems for the controlled release of fragrances was investigated by photoirradiation of undegassed solutions with a xenon lamp as well as natural sunlight. A large variety of precursor compounds was prepared efficiently in a few reaction steps from commercially available starting materials. The Norrish type II photofragmentation was found to be the predominant reaction pathway to yield the desired perfumery alkenes and acetophenones in polar and apolar solution. Systematic GC-MS analysis of the irradiated solutions allowed identification of a series of side products that are due to the presence of oxygen. A detailed analysis of the product distribution after irradiation was carried out for a series of 4-alkoxy-1-phenylbutanone derivatives. Besides the expected acetophenones, vinyl ethers and phenylcyclobutanols, the formation of alkyl formates, alcohols and 4-oxo-4-phenylbutanoates was observed. The product distribution as influenced by solvent polarity, precursor concentration and substituent effects was investigated. The utility of alkyl phenyl ketones as precursors for the light induced controlled release of fragrances under natural daylight conditions was also demonstrated. PMID:12659532

  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. 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one

    PubMed Central

    Caracelli, Ignez; Olivato, Paulo R.; Cerqueira Jr, Carlos R.; Santos, Jean M. M.; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    The piperidone ring in the title compound, C18H19NOS2, is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methyl­ene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of the S-bound phenyl rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is splayed [dihedral angles = 75.97 (6) and 44.21 (7)°, respectively]. The most prominent feature of the crystal packing is the formation of helical supra­molecular chains along the b axis sustained by C—H⋯O inter­actions. The chains are consolidated into a three-dimensional architecture via C—H⋯π inter­actions whereby one S-bound phenyl ring accepts two C—H⋯π contacts. PMID:22719569

  8. Microwave assisted enzymatic kinetic resolution of (±)-1-phenyl-2-propyn-1-ol in nonaqueous media.

    PubMed

    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

  9. Preparation and characterization of phenyl-, benzyl-, and phenethyl-substituted polysilsesquioxanes

    SciTech Connect

    Schneider, D.A.; Loy, D.A.; Baugher, B.M.; Wheeler, D.R.; Assink, R.A.; Alam, T.M.; Saunders, R.

    1998-09-01

    Polysilsesquioxanes are a class of siloxane polymers commonly prepared by the hydrolysis and condensation of trialkoxysilanes or trichlorosilanes. From a trifunctional monomer one would expect the organically-modified polymers to be highly crosslinked and insoluble resins. However, while some silsesquioxane monomers with R = H, CH{sub 3}, or vinyl do form crosslinked polymers capable of forming gels, the majority react to form soluble oligosilsesquioxanes, including discrete polyhedral oligomers, and polymers. Because of their solubility, ladder structures have been proposed. However, viscosity studies by Frye indicate that the polyphenylsilsesquioxane is more likely best represented by a polymer rich in both cyclic structures and branches, but without any regular stereochemistry. In this study, the authors have examined the hydrolysis and condensation polymerizations of phenyltrialkoxysilane, benzyltrialkoxysilane, and 2-phenethyltrialkoxysilane monomers under both acidic and basic conditions. The resulting phenyl, benzyl and phenethyl-substituted polysilsesquioxanes were characterized by {sup 1}H, {sup 13}C, {sup 29}Si NMR, gel permeation chromatography, and differential scanning calorimetry. The effects of the organic substituent (phenyl, benzyl, phenethyl), alkoxide group (OMe, OEt), catalyst (HCl, NaOH), monomer concentration, and polymer processing on polymer molecular weight and glass transition temperature were determined.

  10. 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

  11. 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.

  12. 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. PMID:26070188

  13. Pyrolysis of silica-immobilized benzyl phenyl ether: Competing radical rearrangement pathways under restricted diffusion

    SciTech Connect

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

    1998-12-25

    Pyrolysis studies of silica-immobilized benzyl phenyl ether ({approx}PhOCH{sub 2}Ph or {approx}BPE), a model for related ether structures in fuel resources, have been conducted at 275--325 C to examine the impact of restricted mass transport on the pyrolysis mechanism compared with previous studies in fluid phases. Significant rearrangement chemistry is observed for {approx}BPE occurring through two competitive free-radical pathways that are both promoted by the diffusional constraints. One path involves recombination of incipient benzyl and surface-bound phenoxy radicals to form benzylphenol isomers, 10. The second, previously unreported rearrangement path for {approx}BPE involves a 1,2-phenyl shift in an intermediate radical, {approx}PhOCH{center_dot}Ph, leading to formation of benzhydrol (8) and benzophenone (9) as principal products. The rearrangement products 8--10 typically account for ca. 50% of the pyrolysis products. However, the path selectivity is a sensitive function of {approx}BPE surface coverage and the presence of spacer molecules that either facilitate or hinder hydrogen atom transfer steps on the surface.

  14. Evaluation of smoking on olfactory thresholds of phenyl ethyl alcohol and n-butanol.

    PubMed

    Hayes, J E; Jinks, A L

    2012-09-10

    The effect of smoking on the sense of smell remains inconclusive. Previous research suggests that this is due to idiosyncratic acuity dependent on the odorants used in testing. Specifically, it appears that smokers have reduced olfactory acuity to odorants found within cigarettes compared with odorants not within cigarettes. Given that some of these odorants are used in tomography and magnetic resonance imaging, an in-depth understanding of this phenomenon in smoking individuals is crucial. This study assesses the variation of olfactory thresholds in smokers based on selective impairment to two odors commonly used in olfactory testing - n-butanol and phenyl ethyl alcohol (PEA). We presented to 46 participants an 18 step, forced choice, three choice ascending staircase method sniff bottle threshold test using n-butanol and PEA. PEA is present in cigarettes while n-butanol is not. Therefore n-butanol is used as a covariate to control for variance explained by any general olfactory dysfunction. Using this method, we can focus solely on selective impairment. We discovered that n-butanol threshold scores were significantly different between smokers and nonsmokers. In addition, after using n-butanol as covariate, phenyl ethyl alcohol scores remained significantly different between groups. This data suggests that there is an extended impairment to odors within tobacco and this may explain a cause of the inconclusiveness of past research. PMID:22776624

  15. Communication through the phenyl ring: internal rotation and nuclear quadrupole splitting in p-halotoluenes

    NASA Astrophysics Data System (ADS)

    Shubert, V. Alvin; Schmitz, David; Schnell, Melanie

    2013-08-01

    The rotational spectra of three p-halotoluenes (chloro-, bromo- and iodo-) are reported in the frequency range 2-8.5 GHz, obtained with broadband Fourier-transform microwave spectroscopy. The recorded spectra are highly complicated due to low-barrier V 6 internal rotation of the methyl group as well as strong nuclear quadrupole coupling of the halogen atoms. However, these additional effects allow us, in a comparative manner, to study potential crosstalk of the two substituents via the phenyl ring. The rotational constants and other molecular parameters are reported and compared with quantum chemical calculations. The V 6 internal rotation barrier of the methyl group was found to be 145 GHz for both p-chlorotoluene species. We found that the magnitudes of the quadrupole coupling constants are increased in the halotoluenes compared to the halobenzenes. This increase is due to the +I inductive effect of the methyl group that injects additional electron density into the phenyl π-cloud, thus giving more electron density for the halogen atom to extract. This additional extraction makes the halogen-carbon bond more ionic than in the halobenzenes.

  16. UV Absorption and Luminescence Spectra of [2.2]Paracyclophane Phenyl Derivatives

    NASA Astrophysics Data System (ADS)

    Nurmukhametov, R. N.; Shapovalov, A. V.; Antonov, D. Yu.

    2016-03-01

    UV absorption, fluorescence emission and excitation, and fluorescence excitation synchronous scanning spectra at 298 K and fluorescence and phosphorescence spectra at 77 K were measured for solutions of 4-phenyl- ( I) and 4,12-( II), 4,15- ( III), and 4,16-diphenyl derivatives ( IV) of [2.2]paracyclophane. Analysis of absorption spectra shows that they are determined by two types of chromophores (biphenyl and paracyclophane). It was shown that their weak long wavelength band (310-340 nm) and fluorescence band are governed by the same electron transition from the ground to an excimer-like excited state, as in the case of the unsubstituted macrocycle. Phenyl substitution shows only a weak influence on the energy of this transition. Strong absorption bands of I- IV at 230-310 nm originate from electronic transitions of biphenyl groups in these molecules. The strong bands of isomeric II- IV (with two biphenyl chromophores) differ significantly. It was supposed that this phenomenon was caused by different resonance interaction between electron oscillators (transitions) of the two biphenyl chromophores leading to different splitting of their excited states.

  17. 3-(Di­phenyl­amino)­isobenzo­furan-1(3H)-one

    PubMed Central

    Moreno-Fuquen, Rodolfo; Castillo, Juan C.; Abonia, Rodrigo; Ellena, Javier; Tenorio, Juan C.

    2014-01-01

    In the title isobenzo­furan­one derivative, C20H15NO2, the planar fused-ring system (r.m.s. deviation for the 10 fitted atoms = 0.031 Å) forms dihedral angles of 63.58 (6) and 63.17 (8)° with the N-bound phenyl rings; the dihedral angle between the planes of these phenyl rings is 85.92 (7)°. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions, involving both O atoms, forming helical supra­molecular chains along [001]. PMID:24826181

  18. 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...-), bis phenyl] sulfonyl]amino]-4-(oxo-.kappa.O)-5-pyrimidinyl]azo-.kappaN1]...

  19. 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...-), bis phenyl] sulfonyl]amino]-4-(oxo-.kappa.O)-5-pyrimidinyl]azo-.kappaN1]...

  20. 40 CFR 721.8950 - Chromate(3-), bis[3-[[6-amino-1,4-dihydro-2-[[[4-[(2-hydroxy-1-naphthalenyl)azo] phenyl]sulfonyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Chromate(3-), bis phenyl]sulfonyl... Significant New Uses for Specific Chemical Substances § 721.8950 Chromate(3-), bis phenyl]sulfonyl]amino]-4... substance identified as chromate(3-), bis...

  1. 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, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Chromate(3-), bis phenyl]sulfonyl... Specific Chemical Substances § 721.8940 Chromate(3-), bis phenyl]sulfonyl] amino]-4-(oxo-.kappa.O)-5... substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  2. 40 CFR 721.2095 - Chromate(3-), bis 2-[[substituted-3-[(5-sulfo-1-naphthalenyl)azo] phenyl]azo]substituted...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Chromate(3-), bis 2- phenyl]azo... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2095 Chromate(3-), bis 2- phenyl]azo... reporting. (1) The chemical substance identified generically as chromate(3-), bis 2-...

  3. 40 CFR 721.2095 - Chromate(3-), bis 2-[[substituted-3-[(5-sulfo-1-naphthalenyl)azo] phenyl]azo]substituted...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Chromate(3-), bis 2- phenyl]azo... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2095 Chromate(3-), bis 2- phenyl]azo... reporting. (1) The chemical substance identified generically as chromate(3-), bis 2-...

  4. 40 CFR 721.2095 - Chromate(3-), bis 2-[[substituted-3-[(5-sulfo-1-naphthalenyl)azo] phenyl]azo]substituted...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Chromate(3-), bis 2- phenyl]azo... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2095 Chromate(3-), bis 2- phenyl]azo... reporting. (1) The chemical substance identified generically as chromate(3-), bis 2-...

  5. 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, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Chromate(3-), bis phenyl]sulfonyl... Specific Chemical Substances § 721.8940 Chromate(3-), bis phenyl]sulfonyl] amino]-4-(oxo-.kappa.O)-5... substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  6. 40 CFR 721.2095 - Chromate(3-), bis 2-[[substituted-3-[(5-sulfo-1-naphthalenyl)azo] phenyl]azo]substituted...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Chromate(3-), bis 2- phenyl]azo... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2095 Chromate(3-), bis 2- phenyl]azo... reporting. (1) The chemical substance identified generically as chromate(3-), bis 2-...

  7. 40 CFR 721.8950 - Chromate(3-), bis[3-[[6-amino-1,4-dihydro-2-[[[4-[(2-hydroxy-1-naphthalenyl)azo] phenyl]sulfonyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Chromate(3-), bis phenyl]sulfonyl... Significant New Uses for Specific Chemical Substances § 721.8950 Chromate(3-), bis phenyl]sulfonyl]amino]-4... substance identified as chromate(3-), bis...

  8. 40 CFR 721.8950 - Chromate(3-), bis[3-[[6-amino-1,4-dihydro-2-[[[4-[(2-hydroxy-1-naphthalenyl)azo] phenyl]sulfonyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Chromate(3-), bis phenyl]sulfonyl... Significant New Uses for Specific Chemical Substances § 721.8950 Chromate(3-), bis phenyl]sulfonyl]amino]-4... substance identified as chromate(3-), bis...

  9. 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, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Chromate(3-), bis phenyl]sulfonyl... Specific Chemical Substances § 721.8940 Chromate(3-), bis phenyl]sulfonyl] amino]-4-(oxo-.kappa.O)-5... substance and significant new uses subject to reporting. (1) The chemical substance identified as...

  10. 40 CFR 721.2095 - Chromate(3-), bis 2-[[substituted-3-[(5-sulfo-1-naphthalenyl)azo] phenyl]azo]substituted...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Chromate(3-), bis 2- phenyl]azo... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2095 Chromate(3-), bis 2- phenyl]azo... reporting. (1) The chemical substance identified generically as chromate(3-), bis 2-...

  11. Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines.

    PubMed

    Kadayat, Tara Man; Song, Chanju; Shin, Somin; Magar, Til Bahadur Thapa; Bist, Ganesh; Shrestha, Aarajana; Thapa, Pritam; Na, Younghwa; Kwon, Youngjoo; Lee, Eung-Seok

    2015-07-01

    A series of novel twenty-eight rigid 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines were synthesized and evaluated for their topoisomerase inhibitory activity as well as their cytotoxicity against several human cancer cell lines. Generally, hydroxylated compounds (16-18, 22-25, and 29-31) containing furyl or thienyl moiety at 4-position of central pyridine exhibited strong topoisomerase I and II inhibitory activity compared to positive control, camptothecin and etoposide, respectively, in low micromolar range. Structure-activity relationship study revealed that indenopyridine compounds with hydroxyl group at 2-phenyl ring in combination with furyl or thienyl moiety at 4-position are important for topoisomerase inhibition. Compounds (22-25) which contain hydroxyl group at meta position of the 2-phenyl ring at 2-position and furanyl or thienyl substitution at 4-position of indenopyridine, showed concrete correlations between topo I and II inhibitory activity, and cytotoxicity against evaluated human cancer cell lines. PMID:26022080

  12. Rotating phenyl rings as a guest-dependent switch in two-dimensional metal-organic frameworks.

    PubMed

    Murdock, Christopher R; McNutt, Nicholas W; Keffer, David J; Jenkins, David M

    2014-01-15

    A semirigid bis(1,2,4-triazole) ligand binds in a syn conformation between copper(I) chains to form a series of two-dimensional metal-organic frameworks that display a topology of fused one-dimensional metal-organic nanotubes. These anisotropic frameworks undergo two different transformations in the solid state as a function of solvation. The 2D sheet layers can expand or contract, or, more remarkably, the phenyl rings can rotate between two distinct positions. Rotation of the phenyl rings allows for the adjustment of the tube size, depending on the guest molecules present. This "gate" effect along the 1D tubes has been characterized through single-crystal X-ray diffraction. The transformations can also be followed by powder X-ray diffraction (PXRD) and solid-state (13)C cross-polarization magic-angle-spinning (CP-MAS) NMR. Whereas PXRD cannot differentiate between transformations, solid-state (13)C CP-MAS NMR can be employed to directly monitor phenyl rotation as a function of solvation, suggesting that this spectroscopic method is a powerful approach for monitoring breathing in this novel class of frameworks. Finally, simulations show that rotation of the phenyl ring from a parallel orientation to a perpendicular orientation occurs at the cost of framework-framework energy and that this energetic cost is offset by stronger framework-solvent interactions. PMID:24351165

  13. NMR study about solubilization of phenyl alkyl alcohol in sodium dodecyl sulfate micelle and in BRIJ 35 micelle

    SciTech Connect

    Miyagishi, S.; Nishida, M.

    1980-11-01

    This work examines the NMR spectra of surfactant solutions solubilizing phenyl alkyl alcohols and the effect of holmium ion on them. More detailed information was obtained about the solubilization site. In addition, it was found that the solubilization in BRIJ 35 micelle was different from that in sodium dodecyl sulfate micelle. 16 references.

  14. 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.

  15. Synthesis of methylamino-2-phenyl-2-butyl-3,4,5-trimethoxybenzoate, the main bioactive metabolite of trimebutine maleate.

    PubMed

    Martin, A; Figadère, B; Saivin, S; Houin, G; Chomard, J M; Cahiez, G

    2000-06-01

    The first synthesis of the methylamino-2-phenyl-2-butyl-3,4,5-trimethoxybenzoate (desmethyltrimebutine) I is described. This compound is the main bioactive metabolite of trimebutine II (Debridat, CAS 39133-31-8), an antispasmodic widely used for intestinal diseases since 1969. It was used for pharmacokinetic and bioequivalence studies. PMID:10918948

  16. The Synthesis of 1-Phenyl-1,2,3,4-tetrahydroisoquinolines: An Undergraduate Organic Laboratory Experiment and Class Project.

    ERIC Educational Resources Information Center

    Letcher, R. M.; Sammes, M. P.

    1985-01-01

    Describes an undergraduate organic chemistry experiment (requiring three/four 3-hour laboratory sessions) involving a four-stage synthesis of 1-phenyl-1,2,3,4-tetrahydroisoquinolines via the Pictet-Spengler route. In addition, the experiment allows students to study the spectra and properties of aklaloid-like materials while completing several…

  17. Vibrational and quantum chemical investigation of cyclization of thiosemicarbazide group in 1-benzoyl-4-phenyl-3-thiosemicarbazide

    NASA Astrophysics Data System (ADS)

    Gautam, Priyanka; Prakash, Om; Dani, R. K.; Singh, N. K.; Singh, Ranjan K.

    2014-11-01

    1-Benzoyl-4-phenyl-3-thiosemicarbazide (H3bpt) was treated with acid - base in one sequence and base - acid in other sequence, both of which lead to ring formation of thiosemicarbazide group, giving N-phenyl-5-phenyl-1,3,4-thiadiazol-2-amine (Hppta) in the first case and 4,5-diphenyl-2,4-dihydro-1,2,4-triazole-3-thione (Hdptt) in the second case. The primary (H3bpt) as well as the resulting compounds (Hppta & Hdptt) has been characterized by elemental analyses, NMR, FTIR and Raman spectroscopic techniques. The quantum chemical calculations of the compounds are performed using DFT/B3LYP/6311G(d,p) method for geometry optimizations and also for prediction of the molecular properties. The cyclization is confirmed by disappearance of many bands belonging to the open chain subgroups of H3bpt such as; Nsbnd H stretching, Nsbnd H bending, Csbnd N stretching, Nsbnd H puckering, Cdbnd O stretching etc. The ring formation of 1-benzoyl-4-phenyl-3-thiosemicarbazide (H3bpt) has been further confirmed by the appearance of many bands belonging to the closed ring of thiosemicarbazide in the resulting compounds Hppta and Hdptt.

  18. Investigation on the ZBG-functionality of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase inhibitors.

    PubMed

    Musso, Loana; Cincinelli, Raffaella; Zuco, Valentina; Zunino, Franco; Nurisso, Alessandra; Cuendet, Muriel; Giannini, Giuseppe; Vesci, Loredana; Pisano, Claudio; Dallavalle, Sabrina

    2015-10-15

    A series of alternative Zn-binding groups were explored in the design of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds were less effective than the parent hydroxamic acid. However, the profile of activity shown by the analog bearing a hydroxyurea head group, makes this derivative promising for further investigation. PMID:26376355

  19. 40 CFR 180.221 - O-Ethyl S-phenyl ethylphos-phonodithioate; tolerances for residues.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 25 2012-07-01 2012-07-01 false O-Ethyl S-phenyl ethylphos-phonodithioate; tolerances for residues. 180.221 Section 180.221 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD Specific Tolerances § 180.221...

  20. Synthesis and characterization of Fe (III) complex of an azo dye derived from (2-amino-5-chlorophenyl) phenyl methanone

    NASA Astrophysics Data System (ADS)

    Mini, S.; Meena, S. S.; Bhatt, Pramod; Sadasivan, V.; Vidya, V. G.

    2013-06-01

    The synthesis of Fe (III) complex with an azo dye derived from (2-Amino-5-Chlorophenyl) phenyl methanone is presented. The newly prepared ligand and complex are characterized by elemental analysis, IR, UV-Visible and Mössbauer spectral studies, Molar conductance, and magnetic susceptibility measurements. The thermal stability of the complex is determined from the thermo gravimetric analysis.

  1. 1-(4-Methyl­phen­yl)-2-(phenyl­sulfon­yl)ethanone

    PubMed Central

    Abdel-Aziz, Hatem A.; Al-Rashood, Khalid A.; Ghabbour, Hazem A.; Fun, Hoong-Kun; Chia, Tze Shyang

    2012-01-01

    In the title compound, C15H14O3S, the benzene and phenyl rings make a dihedral angle of 33.56 (16)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into a layer parallel to the ab plane. PMID:22589904

  2. [Effect of phenyl derivative of gamma-aminobutyric acid phenybut on autorhythmic contractile activity of the portal vein].

    PubMed

    Ogluzdina, M V; Barabanova, V V; Berestovitskaia, V M; Usik, N V

    1998-01-01

    The phenyl derivative of the GABA phenybute exerts a direct regulating effect upon phasic and tonic components of the v.cava autorhythmical contractile activity in Wistar rats in media with an altered calcium contents, whereas no such effect occurred in hyper-potassium solution or against the background of verapamil blockade of the potential-dependent calcium channels. PMID:9612864

  3. Visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids to coumarin derivatives under metal-free conditions.

    PubMed

    Yang, Wenchao; Yang, Shuai; Li, Pinhua; Wang, Lei

    2015-05-01

    A visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids has been developed. The arylsulfonylation of alkynes was performed at room temperature under metal-free conditions to generate coumarin derivatives with wide functional group tolerance, good yields and high regioselectivity. PMID:25838160

  4. Coal liquefaction model studies: free radical chain decomposition of diphenylpropane, dibenzyl ether, and phenyl ether via. beta. -scission reactions

    SciTech Connect

    Gillert, K.E.; Gojewski, J.J.

    1982-12-03

    The thermal decompositions to 1,3-diphenylpropane (1), dibenzyl ether (2), and phenethyl phenyl ether (3) have been found to proceed by free radical chain processes. 1 gave toluene and styrene with a reaction order of 1.55, E/sub A/ = 51.4 kcal/mol, and log A = 12.5. The reaction could be initiated by benzyl phenyl ether but not by 1,2-diphenylethane. 2 gave toluene and benzaldehyde with a reaction order of 1.43,E/sub A/ = 48 kcal/mol, and log A = 12.6. The reaction could be initiated with benzyl phenyl ether. 3 gave phenol and styrene with a reaction order of 1.21, E/sub A/ = 50.3 kcal/mol, and log A =12.3. The reaction could be initiated by benzyl phenyl ether. All of the data are consistent with free radical processes with the reaction order determined by the termination reaction. No evidence for concerted reactions has been found.

  5. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false N- diallylamino-4- substituted phenyl] acetamide (generic name). 721.267 Section 721.267 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  6. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false N- diallylamino-4- substituted phenyl] acetamide (generic name). 721.267 Section 721.267 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  7. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false N- diallylamino-4- substituted phenyl] acetamide (generic name). 721.267 Section 721.267 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  8. Research in acetylene containing monomers

    NASA Technical Reports Server (NTRS)

    Ogliaruso, M. A.

    1976-01-01

    The preparation of precursor bisbenzils with pendant acetylene linkages for use in the synthesis of new aromatic poly (phenyl quinoxalines) was investigated. Attempts to condense para, para prime-dibromo benzil and potassium acetylide in liquid ammonia and in toluene, to prepare 4-phenyl acetyl phenyl ether, 4-(paraacetylphenyl) acetyl phenyl ether, 4-phenyl acetyl-4 primeacetyl phenyl acetyl phenyl ether, the reaction of 4-phenyl acetyl phenyl ether with Villsmeier reagent to prepare 4-(beta-chloro cinnamaldehyde) phenyl ether, the reaction of 4-(para-acetyl phenyl) acetyl phenyl ether with Villsmeier reagent, and the oxidation of bibenzil to prepare benzil are described. The reactions of phenyl acetylene with oxidizing agent, of phenyl acetylene with bromine, of 1,1,2,2-tetrabromo ethyl benzene with zinc and with oxidizing agent are described.

  9. 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.

  10. Coordination compound films of 1-phenyl-5-mercaptotetrazole on copper surface

    NASA Astrophysics Data System (ADS)

    Ye, X. R.; Xin, X. Q.; Zhu, J. J.; Xue, Z. L.

    1998-09-01

    The chemical nature of the coordination compound film formed by reacting PMTA (1-phenyl-5-mercaptotetrazole) with a copper surface has been studied by accelerated corrosion tests, linear sweep voltammetry (LSV), cyclic voltammetry (CV), Fourier-transform infrared spectroscopy (FT-IR), X-ray photoelectron spectroscopy (XPS) and Auger electron spectroscopy (AES). These studies show that, in retarding the corrosion of copper substrate, the film is superior to those formed by TTA (tetrazole), BTA (benzotriazole), HBTA (hydroxybenzotriazole), MBT (2-mercaptobenzothiazole), MBI (2-mercaptobenzo-imidazole), 2-AP (2-aminopyrimidine), IBM (imidazole) and chromates. The surface film has been characterized and found to be a polymeric complex of Cu-PMTA. The mechanism for film formation and relationships between this novel film structure and the observed inhibition behavior are discussed.

  11. 1,3,5-Tris(N-phenyl­benzimidazol-2-yl)benzene methanol solvate

    PubMed Central

    Song, Wei-Feng; Wu, Ying; Fan, Yan; Wang, Yue; Liu, Yu

    2009-01-01

    The main mol­ecule of the title compound, C45H30N6·CH3OH, has a non-planar core: the dihedral angles between the benzimidazole rings and the central benzene ring are 20.19 (10), 34.57 (8), and 44.59 (8)°, while the dihedral angles between the peripheral phenyl rings and the attached benzimidazole rings are 84.57 (7), 62.71 (6) and 51.73 (6)°. The tri-substituted benzene mol­ecule is connected to the methanol solvent mol­ecule through an O—H⋯N hydrogen bond, forming a 1:1 solvate. In the crystal structure, no significant π–π inter­actions are present, and the mol­ecules are associated through weak C—H⋯N and C—H⋯O(methanol) contacts. PMID:21577916

  12. 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.

  13. Crystal structures and transistor properties of phenyl-substituted tetrathiafulvalene derivatives.

    PubMed

    Noda, B; Wada, H; Shibata, K; Yoshino, T; Katsuhara, M; Aoyagi, I; Mori, T; Taguchi, T; Kambayashi, T; Ishikawa, K; Takezoe, H

    2007-10-24

    The crystal structures, thin-film properties, and field-effect transistor (FET) characteristics of tetrathiafulvalene (TTF) derivatives with two phenyl groups are systematically investigated. The highest mobility, 0.11 cm(2) V(-1) s(-1), is observed in biphenyl-substituted TTF (1). The correlation between the crystal structures and the FET properties demonstrates that good transistor properties are associated with two-dimensional intermolecular interaction, which is achieved when the molecules are standing nearly perpendicular to the substrate. Since these TTF derivatives are strong electron donors, the use of a metallic charge-transfer salt (TTF)(TCNQ) as the source and drain electrodes has resulted in a considerable reduction of the off current (TCNQ: tetracyanoquinodimethane). PMID:21730442

  14. 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. PMID:26029415

  15. Impact of restricted mass transport on the free-radical decomposition of phenethyl phenyl ether

    SciTech Connect

    Britt, P.F.; Buchanan, A.C. III

    1996-10-01

    In the thermal decomposition of complex macromolecules, reactive intermediates, such as free-radicals, may experience limited diffusional mobility or remain bound to the residual macromolecular framework. To explore the consequences of restricted diffusional and conformational mobility on free-radical reactions, the thermolysis of organic compounds covalently anchored to an inert silica surface through a Si-O-C{sub aryl} have been investigated. In the thermolysis of surface-immobilized phenethyl phenyl ether ({approximately}PPE) at 375{degrees}C, two sets of products, phenol plus surface-immobilized styrene and benzaldehyde plus surface-immobilized toluene, are produced in a 5:1 ratio by a free-radical chain pathway. The impact of a second, co-attached spacer molecule, such as naphthalene or diphenylmethane, on the rate and product selectivity will be presented and the mechanistic implications of restricted diffusional and conformational mobility on the free-radical reaction will be discussed.

  16. N-Phenyl-2-(propan-2-yl­idene)­hydrazine­carboxamide

    PubMed Central

    Attia, Mohamed I.; Ghabbour, Hazem A.; El-Azzouny, Aida A.; Quah, Ching Kheng; Fun, Hoong-Kun

    2012-01-01

    In the title compound, C10H13N3O, the hydrazinecarboxamide N—N—C(=O)—N unit is nearly planar [maximum deviation = 0.018 (2) Å] and is inclined at a dihedral angle of 8.45 (10)° with respect to the plane of the phenyl ring. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond which generates an S(6) ring motif. In the crystal, mol­ecules are linked into an inversion dimer by pairs of N—H⋯O and C—H⋯O hydrogen bonds. PMID:22412570

  17. 6,7-Dimeth­oxy-2,4-di­phenyl­quinoline

    PubMed Central

    Prabhuswamy, M.; Madan Kumar, S.; Swaroop, T. R.; Rangappa, K. S.; Lokanath, N. K.

    2014-01-01

    In the title structure of the title compound, C23H19NO2, two conformationally similar mol­ecules (A and B) comprise the asymmetric unit. The dihedral angle between phenyl rings bridged by the quinoline moiety are 76.25 (8)° in mol­ecule A and 70.39 (9)° in mol­ecule B. In the crystal, the independent mol­ecules are connected by C—H⋯O hydrogen bonds and the resulting dimeric aggregates are linked by π–π [inter-centroid distance = 3.7370 (8) Å] and C—H⋯π inter­actions, forming a three-dimensional architecture. PMID:24764883

  18. Crystal structure of benzyl­tri­phenyl­phospho­nium chloride monohydrate

    PubMed Central

    Ahmad, Jimmy; Abdul Halim, Siti Nadiah; How, Fiona N.-F.

    2015-01-01

    The title compound, Ph3(PhCH2)P+·Cl−·H2O, was obtained unintentionally as the product of an attempted synthesis of a silver di­thio­carbamate complex using benzyl­tri­phenyl­phospho­nium as the counter-ion. The asymmetric unit consists of a phospho­nium cation and a chloride anion, and a water mol­ecule of crystallization. In the crystal, the chloride ion is linked to the water mol­ecule by an O—H⋯Cl hydrogen bond. The three units are further linked via C—H⋯Cl and C—H⋯O hydrogen bonds and C—H⋯ π inter­actions, forming a three-dimensional structure. PMID:26090195

  19. 2-Hydroxy­imino-1-phenyl­ethanone thio­semicarbazone monohydrate

    PubMed Central

    Sarıkavaklı, Nursabah; Babahan, İknur; Şahin, Ertan; Hökelek, Tuncer

    2008-01-01

    In the title thio­semicarbazone derivative, C9H10N4OS·H2O, intra­molecular N—H⋯N hydrogen bonds result in the formation of two nearly coplanar five- and six-membered rings, which are also almost coplanar with the adjacent phenyl ring. The oxime group has an E configuration and is involved in inter­molecular O—H⋯O hydrogen bonding as a donor. In the crystal structure, intra­molecular O—H⋯S and N—H⋯N and inter­molecular O—H⋯O and N—H⋯S hydrogen bonds generate edge-fused R 2 2(8) and R 4 1(11) ring motifs. The hydrogen-bonded motifs are linked to each other to form a three-dimensional supra­molecular network. PMID:21201956

  20. New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius.

    PubMed

    Bai, Zhi-Qiang; Lin, Xiuping; Wang, Yizhu; Wang, Junfeng; Zhou, Xuefeng; Yang, Bin; Liu, Juan; Yang, Xianwen; Wang, Yi; Liu, Yonghong

    2014-06-01

    Two new aromatic butyrolactones, flavipesins A (1) and B (2), two new natural products (3 and 4), and a known phenyl dioxolanone (5) were isolated from marine-derived endophytic fungus Aspergillus flavipes. The structures of compounds 1-5 were elucidated by 1D- and 2D-NMR and MS analysis, the absolute configurations were assigned by optical rotation and CD data, and the stereochemistry of 1 was determined by X-ray crystallography analysis. 1 demonstrated lower MIC values against Staphylococcus aureus (8.0 μg/mL) and Bacillus subtillis (0.25 μg/mL). 1 also showed the unique antibiofilm activity of penetration through the biofilm matrix and kills live bacteria inside mature S. aureus biofilm. PMID:24704337

  1. Cyclo­hexane-1,3-diyl bis­(N-phenyl­carbamate)

    PubMed Central

    Ghalib, Raza Murad; Sulaiman, Othman; Mehdi, Sayed Hasan; Goh, Jia Hao; Fun, Hoong-Kun

    2010-01-01

    The asymmetric unit of the title compound, C20H22N2O4, comprises two crystallographically independent mol­ecules (A and B) with slightly different geometries. The dihedral angle between the two terminal phenyl rings is 61.7 (1)° in mol­ecule A and 29.6 (1)° in B. The cyclo­hexane rings adopt chair conformations. In the crystal packing, inter­molecular N—H⋯O hydrogen bonds inter­connect adjacent mol­ecules into a ladder-like structure along the c axis incorporating R 2 2(20) ring motifs. The crystal packing is further stabilized by weak inter­molecular C—H⋯π inter­actions. PMID:21588737

  2. Hypophagic and hypolocomotive effects of metachloro phenyl piperazine in rats treated with theophylline and caffeine.

    PubMed

    Alam, Nausheen; Haleem, Darakshan Jabeen; Najam, Rahila; Haider, Syeda; Ahmed, Shahida Perveen

    2011-07-01

    Long term intake of coffee is known to produce anxiety and suppression of appetite. 5- hydroxytryptamine (5-HT) acting via 5-HT-2C receptors elicits anorexia and anxiety. The present study is design to monitor metachloro phenyl piperazine (m-CPP) at a dose of 3mg/ml/kg, induces hypophagia and hypolocomotion in rats taking a solution of caffeine (a component of coffee and tea) or theophylline (a component of tea) as a sole source of water. We found that hypophagic and hypolocomotive effects of m-CPP were attenuated in theophylline but not in caffeine treated animals suggesting that long term intake of theophylline may attenuate anorexiogenic and anxiogenic effects of 5-HT. A possible role of 5-HT-2C receptors in the modulation of anxiety and appetite in people drinking coffee or tea discussed. PMID:21715256

  3. (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.

  4. Phenyl substituted indenylphosphine ruthenium complexes as catalysts for dehydrogenation of alcohols.

    PubMed

    Yuan, Jia; Sun, Yue; Yu, Guang-Ao; Zhao, Cui; She, Neng-Fang; Mao, Shu-Lan; Huang, Peng-Shou; Han, Zhi-Jun; Yin, Jun; Liu, Sheng-Hua

    2012-09-14

    Thermal treatment of (1H-inden-3-yl)dicyclohexylphosphinium tetrafluoroborate (1) and (3-mesityl-1H-inden-3-yl)dicyclohexylphosphinium tetrafluoroborate (3) with tBuONa followed by [(η(6)-cymene)RuCl(2))](2) in methanol gave the adduct {(η(6)-cymene)RuCl(2)[(1H-inden-3-yl)PCy(2)]} (6) and {(η(6)-cymene)RuCl(2)[(3-mesityl-1H-inden-3-yl)PCy(2)]} (7), respectively. Thermal treatment of (2-phenyl-1H-inden-3-yl)dicyclohexylphosphinium tetrafluoroborate (4) with tBuONa followed by [(η(6)-cymene)RuCl(2))](2) or RuCl(3)·3H(2)O in methanol gave {Ru[κ(P):(η(6)-2-phenyl-1H-inden-3-yl)PCy(2)]Cl(2)} (8). Whereas (2-mesityl-1H-inden-3-yl)dicyclohexylphosphine (5) reacted with [(η(6)-cymene)RuCl(2))](2) (in toluene) or RuCl(3)·3H(2)O (in ethanol) to afford {Ru[κ(P):(η(6)-2-mesityl-1H-inden-3-yl)PCy(2)]Cl(2)} (9). The molecular structures of complexes 6, 8 and 9 have been determined by single-crystal X-ray diffraction analysis. In addition, complexes 8 and 9 have been found to catalyze the acceptorless dehydrogenation of alcohols in toluene. 9 displayed high activity and different substrates, including cyclic and linear alcohols, were efficiently oxidized to ketones by using 2.0 mol% of catalyst. PMID:22806176

  5. Substituent effects on the reaction rates of hydrogen abstraction in the pyrolysis of phenethyl phenyl ethers

    SciTech Connect

    Beste, Ariana; Buchanan III, A C

    2010-01-01

    We report reaction profiles and forward rate constants for hydrogen abstraction reactions occurring in the pyrolysis of methoxy-substituted derivatives of phenethyl phenyl ether (PhCH{sub 2}CH{sub 2}OPh, PPE), where the substituents are located on the aryl ether ring (PhCH{sub 2}CH{sub 2}OPh-X). We use density functional theory in combination with transition-state theory, and anharmonic corrections are included within the independent mode approximation. PPE is the simplest model of the abundant {beta}-O-4 linkage in lignin. The mechanism of PPE pyrolysis and overall product selectivities have been studied experimentally by one of us, which was followed by computational analysis of key individual hydrogen-transfer reaction steps. In the previous work, we have been able to use a simplified kinetic model based on quasi-steady-state conditions to reproduce experimental {alpha}/{beta} selectivities for PPE and PPEs with substituents on the phenethyl ring (X-PhCH{sub 2}CH{sub 2}OPh). This model is not applicable to PPE derivatives where methoxy substituents are located on the phenyl ring adjacent to the ether oxygen because of the strongly endothermic character of the hydrogen abstraction by substituted phenoxy radicals as well as the decreased kinetic chain lengths resulting from enhanced rates of the initial C?O homolysis step. Substituents decelerate the hydrogen abstraction by the phenoxy radical, while the influence on the benzyl abstraction is less homogeneous. The calculations provide insight into the contributions of steric and polar effects in these important hydrogen-transfer steps. We emphasize the importance of an exhaustive conformational space search to calculate rate constants and product selectivities. The computed rate constants will be used in future work to numerically simulate the pyrolysis mechanism, pending the calculation of the rate constants of all participating reactions.

  6. Control of intramolecular π-π stacking interaction in cationic iridium complexes via fluorination of pendant phenyl rings.

    PubMed

    He, Lei; Ma, Dongxin; Duan, Lian; Wei, Yongge; Qiao, Juan; Zhang, Deqiang; Dong, Guifang; Wang, Liduo; Qiu, Yong

    2012-04-16

    Intramolecular π-π stacking interaction in one kind of phosphorescent cationic iridium complexes has been controlled through fluorination of the pendant phenyl rings on the ancillary ligands. Two blue-green-emitting cationic iridium complexes, [Ir(ppy)(2)(F2phpzpy)]PF(6) (2) and [Ir(ppy)(2)(F5phpzpy)]PF(6) (3), with the pendant phenyl rings on the ancillary ligands substituted with two and five fluorine atoms, respectively, have been synthesized and compared to the parent complex, [Ir(ppy)(2)(phpzpy)]PF(6) (1). Here Hppy is 2-phenylpyridine, F2phpzpy is 2-(1-(3,5-difluorophenyl)-1H-pyrazol-3-yl)pyridine, F5phpzpy is 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)-pyridine, and phpzpy is 2-(1-phenyl-1H-pyrazol-3-yl)pyridine. Single crystal structures reveal that the pendant phenyl rings on the ancillary ligands stack to the phenyl rings of the ppy ligands, with dihedral angles of 21°, 18°, and 5.0° between least-squares planes for complexes 1, 2, and 3, respectively, and centroid-centroid distances of 3.75, 3.65, and 3.52 Å for complexes 1, 2, and 3, respectively, indicating progressively reinforced intramolecular π-π stacking interactions from complexes 1 to 2 and 3. Compared to complex 1, complex 3 with a significantly reinforced intramolecular face-to-face π-π stacking interaction exhibits a significantly enhanced (by 1 order of magnitude) photoluminescent efficiency in solution. Theoretical calculations reveal that in complex 3 it is unfavorable in energy for the pentafluorophenyl ring to swing by a large degree and the intramolecular π-π stacking interaction remains on the lowest triplet state. PMID:22462475

  7. CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines.

    PubMed

    Bharate, Jaideep B; Abbat, Sheenu; Bharatam, Prasad V; Vishwakarma, Ram A; Bharate, Sandip B

    2015-07-28

    Copper bromide catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes directly led to the formation of 3-formyl-2-phenyl-imidazo[1,2-a]pyridines. The quantum chemical calculations were performed to trace the reaction mechanism and get insights into the possible reaction pathway. 2-Aminopyridines on coupling with cinnamaldehyde generate (E)-3-phenyl-3-(pyridin-2-ylamino)acrylaldehyde IV as a key intermediate, which undergoes C-N bond formation reaction to produce 3-formyl-2-phenyl-imidazo[1,2-a]pyridines. PMID:26103156

  8. Investigations on the synthesis and pharmacological properties of amides of 7-methyl-3-phenyl-1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propyl]-2,4- dioxo-1,2,3,4-tetrahydropyrido[2,3-d]-pyrimidine-5-carboxylic acid.

    PubMed

    Sladowska, H; Sieklucka-Dziuba, M; Rajtar, G; Sadowski, M; Kleinrok, Z

    1999-01-01

    Synthesis of amides of 7-methyl-3-phenyl-2,4-dioxo-1,2,3,4- tetrahydropyrido[2,3-d]pyrimidine-5-carboxylic acid (6-10) and their 1-[2-hydroxy-3(4-phenyl-1-piperazinyl)propyl] derivatives (11-15) are described. Some of them displayed strong analgesic activity. PMID:10668178

  9. 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

  10. The influence of the aromatic aglycon of galactoclusters on the binding of LecA: a case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons.

    PubMed

    Casoni, Francesca; Dupin, Lucie; Vergoten, Gérard; Meyer, Albert; Ligeour, Caroline; Géhin, Thomas; Vidal, Olivier; Souteyrand, Eliane; Vasseur, Jean-Jacques; Chevolot, Yann; Morvan, François

    2014-12-01

    A library of 24 new mannose-centered tetragalactoclusters with four different linkers (di- and triethyleneglycol with phosphodiester or phosphorothioate linkages) and six different aromatic aglycons (O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl) was synthesized. Their interactions with LecA were evaluated on a DNA Directed Immobilization (DDI) based glycocluster array allowing the determination of their IC50 against lactose and the evaluation of their dissociation constant (Kd). Finally, the docking simulations confirm the experimental results and demonstrated that the better affinity of O-biphenyl- and O-naphthyl-galactoside is due to a double interaction between the aromatic ring and the histidine 50 and proline 51 of LecA. PMID:25295668

  11. 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.

  12. Iridium(III) complexes with phenyl-tetrazoles as cyclometalating ligands.

    PubMed

    Monti, Filippo; Baschieri, Andrea; Gualandi, Isacco; Serrano-Pérez, Juan J; Junquera-Hernández, José M; Tonelli, Domenica; Mazzanti, Andrea; Muzzioli, Sara; Stagni, Stefano; Roldan-Carmona, Cristina; Pertegás, Antonio; Bolink, Henk J; Ortí, Enrique; Sambri, Letizia; Armaroli, Nicola

    2014-07-21

    Ir(III) cationic complexes with cyclometalating tetrazolate ligands were prepared for the first time, following a two-step strategy based on (i) a silver-assisted cyclometalation reaction of a tetrazole derivative with IrCl3 affording a bis-cyclometalated solvato-complex P ([Ir(ptrz)2(CH3CN)2](+), Hptrz = 2-methyl-5-phenyl-2H-tetrazole); (ii) a substitution reaction with five neutral ancillary ligands to get [Ir(ptrz)2L](+), with L = 2,2'-bypiridine (1), 4,4'-di-tert-butyl-2,2'-bipyridine (2), 1,10-phenanthroline (3), and 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine (4), and [Ir(ptrz)2L2](+), with L = tert-butyl isocyanide (5). X-ray crystal structures of P, 2, and 3 were solved. Electrochemical and photophysical studies, along with density functional theory calculations, allowed a comprehensive rationalization of the electronic properties of 1-5. In acetonitrile at 298 K, complexes equipped with bipyridine or phenanthroline ancillary ligands (1-3) exhibit intense and structureless emission bands centered at around 540 nm, with metal-to-ligand and ligand-to-ligand charge transfer (MLCT/LLCT) character; their photoluminescence quantum yields (PLQYs) are in the range of 55-70%. By contrast, the luminescence band of 5 is weak, structured, and blue-shifted and is attributed to a ligand-centered (LC) triplet state of the tetrazolate cyclometalated ligand. The PLQY of 4 is extremely low (<0.1%) since its lowest level is a nonemissive triplet metal-centered ((3)MC) state. In rigid matrix at 77 K, all of the complexes exhibit intense luminescence. Ligands 1-3 are also strong emitters in solid matrices at room temperature (1% poly(methyl methacrylate) matrix and neat films), with PLQYs in the range of 27-70%. Good quality films of 2 could be obtained to make light-emitting electrochemical cells that emit bright green light and exhibit a maximum luminance of 310 cd m(-2). Tetrazolate cyclometalated ligands push the emission of Ir(III) complexes to the blue, when compared to

  13. Benzo[d]imidazole Transient Receptor Potential Vanilloid 1 Antagonists for the Treatment of Pain: Discovery of trans-2-(2-{2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-phenyl)-propan-2-ol (Mavatrep).

    PubMed

    Parsons, William H; Calvo, Raul R; Cheung, Wing; Lee, Yu-Kai; Patel, Sharmila; Liu, Jian; Youngman, Mark A; Dax, Scott L; Stone, Dennis; Qin, Ning; Hutchinson, Tasha; Lubin, Mary Lou; Zhang, Sui-Po; Finley, Michael; Liu, Yi; Brandt, Michael R; Flores, Christopher M; Player, Mark R

    2015-05-14

    Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a benzo[d]imidazole platform that evolved from a biaryl amide lead. This design composes three sections: a 2-substituted 5-phenyl headgroup attached to the benzo[d]imidazole platform, which is tethered at the two position to a phenyl tail group. Optimization of this design led to the identification of 4 (mavatrep), comprising a trifluoromethyl-phenyl-vinyl tail. In a TRPV1 functional assay, using cells expressing recombinant human TRPV1 channels, 4 antagonized capsaicin-induced Ca(2+) influx, with an IC50 value of 4.6 nM. In the complete Freund's adjuvant- and carrageenan-induced thermal hypersensitivity models, 4 exhibited full efficacy, with ED80 values of 7.8 and 0.5 mg/kg, respectively, corresponding to plasma levels of 270.8 and 9.2 ng/mL, respectively. On the basis of its superior pharmacologic and safety profile, 4 (mavatrep) was selected for clinical development for the treatment of pain. PMID:25850459

  14. The Role of CH···O Coulombic Interactions in Determining Rotameric Conformations of Phenyl Substituted 1,3-Dioxanes and Tetrahydropyrans.

    PubMed

    Wiberg, Kenneth B; Lambert, Kyle M; Bailey, William F

    2015-08-21

    The rotameric conformations of the phenyl ring in both the axial and the equatorial conformers of phenyl substituted 1,3-dioxanes and tetrahydropyrans are compared with those of the corresponding phenylcyclohexanes at the MP2/6-311+G* level. The compounds with an axial phenyl commonly adopt a conformation in which the plane of the aromatic ring is perpendicular to the benzylic C-H bond. However, axial 5-phenyl-1,3-dioxane adopts a "parallel" conformation that allows an ortho hydrogen to be proximate to the two ring oxygens, leading to attractive CH···O interactions. Stabilizing Coulombic interactions of this sort are found with many of the oxygen-containing six-membered rings that were investigated. PMID:26182246

  15. N-(2,3-Dimethyl­phen­yl)-4-methyl-N-(4-methyl­phenyl­sulfon­yl)benzene­sulfonamide

    PubMed Central

    Mughal, Shumaila Younas; Khan, Islam Ullah; Harrison, William T. A.; Khan, Muneeb Hayat; Tahir, Muhammad Nawaz

    2012-01-01

    In the title compound, C22H23NO4S2, the dihedral angles between the dimethyl­phenyl ring and the two methyl­phenyl rings are 41.19 (15) and 20.50 (17)°; the dihedral angle between the methyl­phenyl rings is 48.11 (14)°. The C—N—S—C torsion angles are −87.6 (2) and 77.43 (18)°. The only possible directional inter­actions in the crystal are very weak C—H⋯π inter­actions and very weak π–π stacking between parallel methyl­phenyl rings [centroid-to-centroid separation = 4.010 (2) Å and slippage = 1.987 Å]. PMID:23125784

  16. Hematoxylin substitutes: fluorone black and methyl fluorone black (9-phenyl- and 9-methyl-2,3,7-trihydroxy-6-fluorone) as metachrome iron alum mordant dyes.

    PubMed

    Lillie, R D; Pizzolato, P; Donaldson, P T

    1975-03-01

    The phenyl and methyl trihydroxyfluorones, hitherto used histologically only in the rather difficult and unreliable Turchini technics for discriminating deoxyribonucleic from ribonucleic acid, find a new use as iron mordant metachrome dyes which act as nuclear stains. Nuclear staining is unaffected by acid extraction of nucleic acids, as with hematoxylin lakes. The two dyes, named by Liebermann and Lindenbaum 9-phenyl-2, 3, 7-trihydroxy-6-fluorone, have also acquired (illustrating with the phenyl homolog) longer chemical names of the form 2,6,7-trihydroxy-9-phenylisoxanthene-3-one (Eastman). Aldrich and Pfalz-Bauer adhere to the Liebermann-Lindenbaum nomenclature. The trivial name fluorone black is proposed for the phenyl homolog and methyl fluorone black for the methyl homolog. The iron lake of fluorone black appears to be a useful substitute for iron hematoxylin, methyl flurone black less useful. Neither dye has the diverse capability of hematoxylin. PMID:49945

  17. 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

  18. 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.

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

    PubMed

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

    2015-12-01

    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, mol-ecules are linked via C-H⋯I hydrogen bonds, forming slabs parallel to the ab plane. Within the slabs there are weak π-π inter-actions present involving the mesityl and phenyl rings [inter-centroid distances are 3.8663 (18) and 3.8141 (18) Å]. PMID:26870488

  20. 1-(4-Fluoro­phen­yl)-2-(phenyl­sulfon­yl)ethanone

    PubMed Central

    Abdel-Aziz, Hatem A.; Ghabbour, Hazem A.; Chantrapromma, Suchada; Fun, Hoong-Kun

    2012-01-01

    In the title compound, C14H11FO3S, the unit comprising the ethanone and 4-fluoro­phenyl groups is essentially planar, with an r.m.s. deviation of 0.0084 (2) Å for the ten non-H atoms, and it makes a dihedral angle of 37.31 (10)° with the phenyl ring. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R 2 2(16) graph-set motifs. The dimers are stacked along the b axis through further C—H⋯O hydrogen bonds. PMID:22719455

  1. 3-Methyl-4,5-di­hydro­oxazolium tetra­phenyl­borate

    PubMed Central

    Tiritiris, Ioannis; Saur, Stefan; Kantlehner, Willi

    2014-01-01

    In the cation of the title salt, C4H8NO+·C24H20B−, the C—N bond lengths are 1.272 (2), 1.4557 (19) and 1.4638 (19) Å, indicating double- and single-bond character, respectively. The C—O bond length of 1.3098 (19) Å shows that double-bond character and charge delocalization occurs within the NCO plane of the cation. In the crystal, a C—H⋯π inter­action is present between the methyl­ene H atom of the cation and one phenyl ring of the tetra­phenyl­borate ion. The latter forms an aromatic pocket in which the cation is embedded. PMID:24765023

  2. 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.

  3. 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

  4. Novel H2 activation by a tris[3,5-bis(trifluoromethyl)phenyl]borane frustrated Lewis pair.

    PubMed

    Herrington, Thomas J; Thom, Alex J W; White, Andrew J P; Ashley, Andrew E

    2012-08-14

    Tris[3,5-bis(trifluoromethyl)phenyl]borane (1, BArF(18)), has been synthesised on a practical scale for the first time. According to the Gutmann-Beckett method it is a more powerful Lewis acid than B(C(6)F(5))(3). It forms a 'frustrated Lewis pair' with 2,2,6,6-tetramethylpiperidine which cleaves H(2) to form a salt containing the novel anion [μ-H(BArF(18))(2)](-). PMID:22532230

  5. Pulse radiolysis study of reactions OH ., H . and e -aq with spin trap C-phenyl- N-tertiary-butylnitrone

    NASA Astrophysics Data System (ADS)

    Zubarev, V. E.; Mehnert, R.; Brede, O.

    The primary products of water radiolysis OH ., H . and e -aq react with C-phenyl- N-tert-butyl-nitrone(PBN) but not in a simple spin trapping manner. OH . adds mainly to the aromatic ring yielding cyclohexadienyl type radicals, whereas e -aq in pure water forms the PBN anion via the proposed intermediate O .- and alcohol radicals and an imine in the presence of alcohols.

  6. 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.

  7. Crystal structure of (Z)-1-phenyl-3-styryl­undeca-2-en-4,10-diyn-1-ol

    PubMed Central

    Ganguly, Rakesh; Sally; Chan, Philip Wai Hong

    2015-01-01

    The mol­ecule of the title compound, C25H24O, obtained by acid-catalysed 1,3-migration of an alcohol group, is T-shaped. The planes of the two phenyl rings are inclined to one another by 81.9 (2)°. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains along [001]. PMID:25705512

  8. Crystal structure and photochromism of 1-phenyl-3-methyl-4-benzyl-5-one-pyrazole S-methyl thiosemicarbazone

    NASA Astrophysics Data System (ADS)

    Liu, Lang; Jia, Dian-zeng; Ji, Ya-li; Yu, Kai-bei

    2003-07-01

    A new organic photochromic compound containing pyrazolone-ring photochromic functional unit: 1-phenyl-3-methyl-4-benzyl-5-one pyrazole S-methyl thiosemicarbazone (PMBP-smtsc) was synthesized. The photochromic properties and photochemical kinetics of PMBP-smtsc have been studied by UV reflectance spectra under irradiation of 365 nm light. The crystal structure analyses of photocolored product show the photochromism is due to the photoisomerization from enol form to keto form through an intermolecular proton transfer.

  9. Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

    PubMed Central

    Ayoup, Mohammed Salah; Cordes, David B; Slawin, Alexandra M Z

    2015-01-01

    Summary Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds. PMID:26877788

  10. New N-phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATPase inhibitors of DNA gyrase.

    PubMed

    Zidar, Nace; Tomašič, Tihomir; Macut, Helena; Sirc, Anja; Brvar, Matjaž; Montalvão, Sofia; Tammela, Päivi; Ilaš, Janez; Kikelj, Danijel

    2016-07-19

    Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 μM against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds - especially by varying their size, the position and orientation of key functional groups, and their acid-base properties. The structure-activity relationship (SAR) was examined and the results were rationalised with molecular docking. PMID:27100032

  11. Influence of the solvent on the interaction of phenyl isocyanate with proton donors, catalyzed by copper(II) acetylacetonate

    SciTech Connect

    Bakalo, L.A.; Rakhlevskii, L.V.

    1987-09-01

    The influence of the medium on the noncatalytic and copper(II)-acetylacetonate-catalyzed interaction of phenyl isocyanate with n-butanol under conditions of an excess of isocyanate was investigated. It was shown that the product of superequimolar conversion of isocyanate is n-butyl-..cap alpha.., ..gamma..-diphenylallophanate. The kinetic and thermodynamic peculiarities of the process of formation of urethane and allophanate in various solvents are discussed.

  12. Coal liquefaction model studies: free radical chain decomposition of diphenylpropane, dibenzyl ether, and phenyl ether via. beta. -scission reactions

    SciTech Connect

    Gilbert, K.E.; Gajewski, J.J.

    1982-01-01

    The thermal decompositions of 1,3-diphenylpropane (1), dibenzyl ether (2), and phenethyl phenyl ether (3) have been found to proceed by free radical chain processes. 1 gave toluene and styrene with a reaction order of 1.55, E/sub A/ = 51.4 kcal/mol, and log A = 12.5. The reaction could be initiated by benzyl phenyl ether but not by 1,2-diphenylethane. 2 gave toluene and benzaldehyde with a reaction order of 1.43, E/sub A/ = 48 kcal/mol, and log A = 12.6. The reaction could be initiated with benzyl phenyl ether. 3 gave phenol and styrene with a reaction order of 1.21, E/sub A/ = 50.3 kcal/mol, and log A = 12.3. The reaction could be initiated by benzyl phenyl ether. All of the data are consistent with free radical chain processes with the reaction order determined by the termination reaction. No evidence for concerted reactions has been found. The thermal chemistry of three-atom links is best described by free radical chain processes. The products are consistent with a free radical chain process involving a ..beta..-scission reaction, and the reaction orders range between first and three-halves order depending upon the nature of the chain termination reaction. Activation parameters are readily estimated from thermochemical kinetic data on the individual reactions with log A approx. = 12 and E/sub A/approx. = 50 kcal/mol. Unlike the one- and two-atom linkages, reactions of the three-atom linkages are promoted by free radical initiators. The potential for inhibition of free radical chains also exists and is currently being studied. 4 tables.

  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

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721... 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, 2012 CFR

    2012-07-01

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721... 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, 2010 CFR

    2010-07-01

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721... 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, 2013 CFR

    2013-07-01

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721... 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. 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

    ...-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl) phosphate. 721... 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...

  18. 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...

  19. 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...

  20. 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...

  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, 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...

  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, 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...

  3. 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.

  4. N,N′-[(2E,3E)-Butane-2,3-diylidene]bis[4-fluoro-2-(1-phenyl­eth­yl)aniline

    PubMed Central

    Wei, Juanjuan; She, Houde; Shi, Lijun; Lei, Ziqiang

    2014-01-01

    The title mol­ecule, C32H30F2N2, a product of the condensation reaction of butane-2,3-dione and 4-fluoro-2-(1-phenyl­eth­yl)aniline, is located about an inversion centre. In the asymmetric unit, the dihedral angle between the planes of the benzene and phenyl rings is 84.27 (5)°. Neither hydrogen bonding nor aromatic stacking is observed in the crystal structure. PMID:24764988

  5. 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.

  6. 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.

  7. DFT Study on the Mechanisms of Stereoselective C(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile

    NASA Astrophysics Data System (ADS)

    Wei, Donghui; Tang, Mingsheng

    2009-09-01

    Recently, the first examples of direct vinylation of 1-substituted imidazoles at the 2-position of the imidazole nucleus have been described (J. Org. Chem. 2008, 73, 9155-9157). 1-Substituted imidazoles are C(2)-vinylated with 3-phenyl-2-propynenitrile at room temperature without catalyst and solvent to afford 3-(1-organyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitriles, mainly (ca. 95%) as (Z)-isomers, in 56-88% yield. Nevertheless, the stereoselectivity of vinylation, which has been elusive over the past decades, is still a big problem to explain. In this paper, the reaction mechanisms of stereoselective C(2)-vinylation of 1-methylimidazole with 3-phenyl-2-propynenitrile have been investigated using density functional theory (DFT). The geometries of the reactants, transition states, intermediates, and products were optimized at the B3LYP/6-31G(d,p) level. The calculated results reveal that the reaction contains three processes: formation of zwitterion, proton transfer, and ring rearrangement. Four possible reaction channels are shown, including two (E)-isomer channels and two (Z)-isomer channels. One of the (Z)-isomer channels has the lowest energy barrier among all the four channels, with the highest energy barrier for 83.62 kJ/mol, so it occurs more often than the others at room temperature, which is in good agreement with experiment. Further calculations of solvation effects show that the title reaction can be carried out more smoothly in the gas phase.

  8. Synthesis and Biological Evaluation of Novel N-phenyl-5-carboxamidyl Isoxazoles as Potential Chemotherapeutic Agents for Colon Cancer.

    PubMed

    Shaw, Jiajiu; Chen, Ben; Bourgault, Jean P; Jiang, Hao; Kumar, Narendra; Mishra, Jayshree; Valeriote, Frederick A; Media, Joe; Bobbitt, Kevin; Pietraszkiewicz, Halina; Edelstein, Matthew; Andreana, Peter R

    2012-01-01

    A new series of isoxazole derivatives, N-phenyl-5-carboxamidyl isoxazoles, was investigated for their anticancer activity with solid tumor selectivity. Six N-phenyl-5-carboxamidylisoxazoles were chemically synthesized and evaluated by the in vitro disk-diffusion assay and IC50 cytotoxicity determination. The results showed that one of the derivatives, compound 3, N-(4-chlorophenyl)-5-carboxamidyl isoxazole, was the most active against colon 38 and CT-26 mouse colon tumor cells with an IC50 of 2.5 μg/mL for both cell lines. Western blot analysis showed that compound 3 significantly down-regulated the expression of phosphorylated STAT3 in both human and mouse colon cancer cells indicating that the mechanism of action for compound 3 may involve the inhibition of JAK3/STAT3 signaling pathways. Flow cytometric analysis with Annexin V staining showed that the death induced by compound 3 is mediated through cell necrosis and not apoptotic pathway. In summary, our results show that compound 3 is a new N-phenyl-5-carboxamidyl isoxazole with potential anticancer activity. Compound 3 inhibits the phosphorylation of STAT3, a novel target for chemotherapeutic drugs, and is worthy of further investigation as a potential chemotherapeutic agent for treating colon cancer. PMID:25285182

  9. Crystal structure of (2S/2R,3S/3R)-3-hydroxy-2-phenyl-chroman-4-one.

    PubMed

    Belguedj, Roumaissa; Bouacida, Sofiane; Merazig, Hocine; Chibani, Aissa; Bouraiou, Abdelmalek

    2015-02-01

    In the title mol-ecule, C15H12O3, the C atoms bearing the hy-droxy group and the phenyl ring are disordered over two sets of sites with refined occupancies of 0.573 (7) and 0.427 (7). There is also disorder of the phenyl ring but the hy-droxy group was refined as ordered. The dihedral angles between the benzene ring of the chromane ring system and the phenyl ring are 89.7 (2)° for the major component of disorder and 72.1 (3)° for the minor component. Both disorder components of the the di-hydro-pyran ring are in a half-chair conformation. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(10) graph-set motif. Weak C-H⋯π inter-actions link these dimers into ladders along [001]. PMID:25878868

  10. 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. PMID:27309947

  11. Stability and isomerization reactions of phenyl cation C6H5+ isomers

    NASA Astrophysics Data System (ADS)

    Shi, Dandan; Yang, Xue; Zhang, Xiaomei; Shan, Shimin; Xu, Haifeng; Yan, Bing

    2016-03-01

    As a key polyatomic molecular cation that plays a pivotal role in growth of the polycyclic aromatic hydrocarbons, phenyl cation C6H5+ exhibits various isomers and isomerization reactions. Investigation on the structure and stability of the isomers as well as the isomerization is important for better understanding the chemical reactions involving C6H5+ cations. In this work, we have performed a theoretical study on the stability and isomerization reactions of C6H5+ isomers at density functional theory B3LYP/6-311G (d, p) level. We have obtained a total of 60 isomers of C6H5+ cations, most of which are reported for the first time. The geometries, vibrational frequencies, thermodynamic properties and stability of 28 out of 60 isomers have been summarized in detail. Different ring-to-ring and ring-to-chain isomerization pathways, which are connected via 28 transition states, have been investigated using the intrinsic reaction coordinate method. The results show that the isomerization reactions occur via hydrogen migration followed by bond-breaking and reconstruction.

  12. Use of novel phenyl-hexyl core-shell particles in nano-LC.

    PubMed

    Fanali, Salvatore; Rocchi, Silvia; Chankvetadze, Bezhan

    2013-06-01

    This paper reports the use of novel phenyl-hexyl core-shell particles packed into fused silica capillaries in nano-LC. Capillary columns of different id of 25, 50, 75, 100, and 150 μm were packed employing the slurry packing method. The columns were used for the separation of a model mixture containing five aromatic hydrocarbons. Benzene, toluene, ethylbenzene, n-propylbenzene, and n-butylbenzene were separated utilizing an isocratic elution mode. Mixtures of water/ACN at different ratio were studied to find optimal experimental conditions for baseline separation of all sample components. As expected with this novel stationary phase, an RP chromatographic mechanism was observed. A mixture of water/ACN, 30:70, v/v allowed the complete resolution of the studied analytes. Efficiency increased by decreasing the capillary id recording the highest number of plates per meter with capillaries of 25 μm id. The decrease of the column id also resulted in a flatter dependence of the plate numbers on the linear flow rate of the mobile phase allowing the increase of the flow rate of the mobile phase without significant decrease of efficiency. PMID:23423853

  13. Magneto-optical spectroscopic studies of solid and solution-phase tetra-phenyl porphyrin

    NASA Astrophysics Data System (ADS)

    Wahlen-Strothman, Jacob; Pan, Zhen Wen; Manning, Lane; Furis, Madalina; Chu, Kelvin

    2011-03-01

    Tetraphenylporphyrin (TPP) is a synthetic heterocyclic compound that serves as a model system for heme proteins and cytochromes. TPP can accomodate a metal ion in the center; D-shell ion porphyrin complexes with a crystalline solid phase are of interest for magnetic studies because of the possibility of macroscopic long range magnetic order of the ion spins. We have investigated the 5K magnetic properties of poly-crystalline thin films of the heme protoporphyrin IX analogue tetra-phenyl porphyrin, complexed with Zn and Mn, deposited through a capillary pen technique that produces 100um to 1 mm sized grains. Our novel experimental setup measures the UV/VIS, linear dichroism and magnetic circular dichorism simultaneously, incorporates a photoelastic modulator and a microscopy superconducting magnet for high-field (5T) measurements. We present solution and crystalline data on metal-complexed TPP; data are analyzed in terms of A and B-type MCD using a perimeter model. We find good agreement with previous solution data, and novel crystalline phase spectra that are correlated to the long range ordering. This work supported by NSF DMR-0821268, DUE-0942562 and EPS-0701410.

  14. 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.

  15. Entry of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine into the rat brain

    SciTech Connect

    Riachi, N.J.; LaManna, J.C.; Harik, S.I.

    1989-06-01

    We studied blood-to-brain entry of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 1-methyl-4-phenylpyridinium (MPP+) and butanol in anesthetized rats using the indicator-fractionation method with right atrial bolus injection. Minimal amounts of MPP+, which has low octanol/water partition coefficient, crossed the blood-brain barrier. MPTP and butanol, both of which have high octanol/water partition coefficients, were almost completely extracted by all regions of the brain on the first pass. The main difference between the MPTP and butanol tracers is that butanol rapidly left the brain with an exponential rate constant of 1.24 min-1, whereas MPTP was avidly retained by the brain with a washout rate constant of 0.10 min-1 (mean values for the four brain regions that we studied). Early retention of MPTP by the brain was not due to its rapid metabolism by monoamine oxidase because pargyline pretreatment did not affect this rate constant. However, 30 min after (/sup 3/H)MPTP injection, brain retention of the 3H tracer was reduced significantly by pargyline treatment, and the ratio of brain MPTP/MPP+ was increased markedly.

  16. Hartree-Fock and Density Functional Theory analysis of N-phenyl-1,2-naphthylamine.

    PubMed

    Sengül, Meryem Şenay; Cınaklı, Salih; Böyükata, Mustafa

    2013-10-01

    The energetic properties of N-phenyl-1,2-naphthylamine have been determined using a series of theoretical calculations and their geometries have been optimized using Hartree-Fock (HF) and Density Functional Theory (DFT). The structures have been examined to predict lower-lying energy structure of the title molecule within the considered potential conformations. Structural parameters and energetics, such as total energies with Zero-Point energy corrections, highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies, have been analyzed and compared between the structural isomers. 1-NPN is the most commonly used molecule for many purposes, mainly as the fluorescent probe in binding assays. When compared the two structures, we showed that 2-NPN isomers are energetically more stable than 1-NPN isomers. It is possible that 2-NPN may be favored in many applications with respect to 1-NPN, and thus its function may be understood in the light of its molecular and structural properties. PMID:23786979

  17. Hartree-Fock and Density Functional Theory analysis of N-phenyl-1,2-naphthylamine

    NASA Astrophysics Data System (ADS)

    Şengül, Meryem Şenay; Cınaklı, Salih; Böyükata, Mustafa

    2013-10-01

    The energetic properties of N-phenyl-1,2-naphthylamine have been determined using a series of theoretical calculations and their geometries have been optimized using Hartree-Fock (HF) and Density Functional Theory (DFT). The structures have been examined to predict lower-lying energy structure of the title molecule within the considered potential conformations. Structural parameters and energetics, such as total energies with Zero-Point energy corrections, highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies, have been analyzed and compared between the structural isomers. 1-NPN is the most commonly used molecule for many purposes, mainly as the fluorescent probe in binding assays. When compared the two structures, we showed that 2-NPN isomers are energetically more stable than 1-NPN isomers. It is possible that 2-NPN may be favored in many applications with respect to 1-NPN, and thus its function may be understood in the light of its molecular and structural properties.

  18. Effects of the Hydroxyl Group on Phenyl Based Ligand/ERRγ Protein Binding

    PubMed Central

    2015-01-01

    Bisphenol-A (4,4′-dihydroxy-2,2-diphenylpropane, BPA, or BPA-A) and its derivatives, when exposed to humans, may affect functions of multiple organs by specific binding to the human estrogen-related receptor γ (ERRγ). We carried out atomistic molecular dynamics (MD) simulations of three ligand compounds including BPA-A, 4-α-cumylphenol (BPA-C), and 2,2-diphenylpropane (BPA-D) binding to the ligand binding domain (LBD) of a human ERRγ to study the structures and energies associated with the binding. We used the implicit Molecular Mechanics/Poisson–Boltzmann Surface Area (MM/PBSA) method to estimate the free energies of binding for the phenyl based compound/ERRγ systems. The addition of hydroxyl groups to the aromatic ring had only a minor effect on binding structures and a significant effect on ligand/protein binding energy in an aqueous solution. Free binding energies of BPA-D to the ERRγ were found to be considerably less than those of BPA-A and BPA-C to the ERRγ. These results are well correlated with those from experiments where no binding affinities were determined in the BPA-D/ERRγ complex. No conformational change was observed for the helix 12 (H-12) of ERRγ upon binding of these compounds preserving an active transcriptional conformation state. PMID:25098505

  19. Validation and scale-up of plasmid DNA purification by phenyl-boronic acid chromatography.

    PubMed

    Gomes, A Gabriela; Azevedo, Ana M; Aires-Barros, M Raquel; Prazeres, D Miguel F

    2012-11-01

    This study addresses the feasibility of scaling-up the removal of host cell impurities from plasmid DNA (pDNA)-containing Escherichia coli lysates by phenyl-boronic (PB) acid chromatography using columns packed with 7.6 and 15.2 cm(3) of controlled porous glass beads (CPG) derivatized with PB ligands. Equilibration was performed with water at 10 cm(3) /min and no conditioning of the lysate feed was required. At a ratio of lysate feed to adsorbent volume of 1.3, 93-96% of pDNA was recovered in the flow through while 66-71% of impurities remained bound (~2.5-fold purification). The entire sequence of loading, washing, elution, and re-equilibration was completed in 20 min. Run-to-run consistency was observed in terms of chromatogram features and performance (yield, purification factor, agarose electrophoresis) across the different amounts of adsorbent (0.75-15.2 cm(3) ) by performing successive injections of lysates prepared independently and containing 3.7 or 6.1 kbp plasmids. The column productivity at large scale was 4 dm(3) of alkaline lysate per hour per dm(3) of PB-CPG resin. The method is rapid, reproducible, simple, and straightforward to scale-up. Furthermore, it is capable of handling heavily contaminated samples, constituting a good alternative to purification techniques such as isopropanol precipitation, aqueous two-phase systems, and tangential flow filtration. PMID:23175141

  20. Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives.

    PubMed

    Wang, Xiaoqin; Xie, Xiaoyang; Cai, Yuanhong; Yang, Xiaolan; Li, Jiayu; Li, Yinghan; Chen, Wenna; He, Minghua

    2016-01-01

    A series of new 2-phenyl-quinoline-4-carboxylic acid derivatives was synthesized starting from aniline, 2-nitrobenzaldehyde, pyruvic acid followed by Doebner reaction, amidation, reduction, acylation and amination. All of the newly-synthesized compounds were characterized by ¹H-NMR, (13)C-NMR and HRMS. The antibacterial activities of these compounds against Gram-negative (Escherichia coli, Pseudomonas aeruginosa) and Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis), as well as one strain of methicillin-resistant Staphylococcus aureus (MRSA) bacteria were evaluated by the agar diffusion method (zone of inhibition) and a broth dilution method (minimum inhibitory concentration (MIC)), and their structure-activity relationships were obtained and discussed. The results revealed that some compounds displayed good antibacterial activity against Staphylococcus aureus, and Compounds 5a₄ and 5a₇ showed the best inhibition with an MIC value of 64 μg/mL against Staphylococcus aureus and with an MIC value of 128 μg/mL against Escherichia coli, respectively. The results of the MTT assay illustrated the low cytotoxicity of Compound 5a₄. PMID:26978336

  1. Thermolysis of phenethyl phenyl ether: A model of ether linkages in low rank coal

    SciTech Connect

    Britt, P.F.; Buchanan, A.C. III; Malcolm, E.A.

    1994-09-01

    Currently, an area of interest and frustration for coal chemists has been the direct liquefaction of low rank coal. Although low rank coals are more reactive than bituminous coals, they are more difficult to liquefy and offer lower liquefaction yields under conditions optimized for bituminous coals. Solomon, Serio, and co-workers have shown that: in the pyrolysis and liquefaction of low rank coals, a low temperature cross-linking reaction associated with oxygen functional groups occurs before tar evolution. A variety of pretreatments (demineralization, alkylation, and ion-exchange) have been shown to reduce these retrogressive reactions and increase tar yields, but the actual chemical reactions responsible for these processes have not been defined. In order to gain insight into the thermochemical reactions leading to cross-linking in low rank coal, we have undertaken a study of the pyrolysis of oxygen containing coal model compounds. Solid state NMR studies suggest that the alkyl aryl ether linkage may be present in modest amounts in low rank coal. Therefore, in this paper, we will investigate the thermolysis of phenethyl phenyl ether (PPE) as a model of 0-aryl ether linkages found in low rank coal, lignites, and lignin, an evolutionary precursor of coal. Our results have uncovered a new reaction channel that can account for 25% of the products formed. The impact of reaction conditions, including restricted mass transport, on this new reaction pathway and the role of oxygen functional groups in cross-linking reactions will be investigated.

  2. Mode-specific intermolecular vibrational energy transfer. I. Phenyl selenocyanate and deuterated chloroform mixture

    NASA Astrophysics Data System (ADS)

    Bian, Hongtao; Li, Jiebo; Wen, Xiewen; Zheng, Junrong

    2010-05-01

    Vibrational energy transfer from the first excited state (2252 cm-1) of the C-D stretch of deuterated chloroform (DCCl3) to the 0-1 transition (2155 cm-1) of the CN stretch of phenyl selenocyanate (C6H5SeCN) in their 1:1 liquid mixture was observed with a pump/probe two-color two dimensional infrared spectroscopic technique. The mode-specific energy transfer can occur mainly because of the long vibrational lifetime of the CN stretch first excited state (˜300 ps) and the relatively strong hydrogen-bond between the C-D and CN (calculated H-bond formation energy in gas phase ˜-5.4 kcal/mol). The mode-specific energy transfer is relatively low efficient (only ˜2%), which is mainly because of the relatively short vibrational lifetime (˜9 ps) of the C-D stretch first excited state and the big donor/acceptor energy mismatch (97 cm-1) and the slow transfer kinetics (1/kCD→CN=330 ps).

  3. 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.

  4. 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. PMID:26756819

  5. 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).

  6. Potential Activity of 3-(2-Chlorophenyl)-1-phenyl-propenonein Accelerating Wound Healing in Rats

    PubMed Central

    Dhiyaaldeen, Summaya M.; Alshawsh, Mohammed A.; Salama, Suzy M.; Alwajeeh, Nahla S. I.

    2014-01-01

    Wound healing involves inflammation followed by granular tissue development and scar formation. In this study, synthetic chalcone 3-(2-Chlorophenyl)-1-phenyl-propenone (CPPP) was investigated for a potential role in enhancing wound healing and closure. Twenty-four male rats were divided randomly into 4 groups: carboxymethyl cellulose (CMC) (0.2 mL), Intrasite gel, and CPPP (25 or 50 mg/mL). Gross morphology, wounds treatment with the CPPP, and Intrasite gel accelerate the rate of wound healing compared to CMC group. Ten days after surgery, the animals were sacrificed. Histological assessment revealed that the wounds treated with CPPP showed that wound closure site contained little amount of scar and the granulation tissue contained more collagen and less inflammatory cells than wound treated with CMC. This finding was confirmed with Masson's trichrome staining. The antioxidant defence enzymes catalase (CAT) and superoxide dismutase (SOD) were significantly increased in the wound homogenates treated with CPPP (P < 0.05) compared to CMC treated group. However, in the CPPP treatment group, lipid peroxidation (MDA) was significantly decreased (P < 0.05), suggesting that the CPPP also has an important role in protection against lipid peroxidation-induced skin injury after ten days of treatment with CPPP, which is similar to the values of cytokines TGF-β and TNF-α in tissue homogenate. Finally the administration of CPPP at a dosage of 25 and 50 mg/kg was suitable for the stimulation of wound healing. PMID:24587992

  7. Antipoliovirus activity and mechanism of action of 3-methylthio-5-phenyl-4-isothiazolecarbonitrile.

    PubMed

    Garozzo, A; Stivala, A; Tempera, G; Castro, A

    2010-12-01

    Our previous studies described the synthesis and the antiviral activity of 3,4,5-trisubstituted isothiazole derivatives that were found to be particularly effective against enteroviruses. Compound 3-methylthio-5-phenyl-4-isothiazolecarbonitrile (IS-2) exhibited an interesting anti-poliovirus activity with a high selectivity index. In the present study we investigated the mechanism of action of this compound. Studies on the time of IS-2 addition to poliovirus type 1 infected cells suggested that the compound may inhibit some early process of viral replication. In order to determine its mechanism of action, we evaluated the rate of attachment and internalization of purified [³H]uridine-labeled poliovirus to HEp-2 cells in the presence or absence of IS-2. No effect on poliovirus adsorption and internalization to host cells was detected. We also investigated the influence of the compound on virus uncoating using labeled poliovirus and measuring the radioactivity of oligoribonucleotides formed from viral RNA susceptible to ribonuclease. These experiments demonstrated that poliovirus uncoating is influenced by IS-2 action. PMID:20955736

  8. Negative polarity of phenyl-C61 butyric acid methyl ester adjacent to donor macromolecule domains

    NASA Astrophysics Data System (ADS)

    Alley, Olivia J.; Wu, Meng-Yin; Johns, Gary L.; Dawidczyk, Thomas J.; Hardigree, Josué F. Martínez; Markovic, Nina; Arnold, Michael S.; Katz, Howard E.

    2015-01-01

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (Voc) 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 Voc, 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-C61 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 Voc, 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.

  9. Thermal and spectroscopic studies of scandium complex of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone

    NASA Astrophysics Data System (ADS)

    Akama, Yoshifumi; Sawada, Tadanobu; Ueda, Toyotoshi

    2005-08-01

    The scandium complexes of Sc(PMBP)3·H2O (non-crystal) and Sc(PMBP)3 (crystal) with 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) were prepared and characterized by thermal analysis, IR, NMR and MS spectroscopies. The crystal structure of the complex, obtained by X-ray analysis, indicates that PMBP is a bidentate ligand in the complex and that the Sc atom is six-coordinate and is in a meridional octahedral environment. The order of the ring current effect on the pyrazolone ring is Sc(PMBP)3 >PMBP(enol)> PMBP(keto). The metal to ligand stoichiometry was found to be 1:3. The crystalline complex melts at 209 °C, followed by degradation at about 310 °C, with the beginning of decomposition. The enthalpy of melting was found to be 61 kJ/mol. On the other hand, the non-crystalline complex was found to change into a crystalline complex at 176 °C with an exothermic reaction before melting at 217 °C. The IR band observed at approximately, 450 cm-1 is possibly due to the stretching of the Sc-O bond.

  10. 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.

  11. 1-Phenyl-3-(2-thiazolyl)-2-thiourea inhibits melanogenesis via a dual-action mechanism.

    PubMed

    Kim, Yong Hyun; Park, Jong Il; Myung, Cheol Hwan; Lee, Ji Eun; Bang, Seunghyun; Chang, Sung Eun; Hwang, Jae Sung

    2016-09-01

    1-Phenyl-3-(2-thiazolyl)-2-thiourea (PTTU) is a well-characterized dopamine β-hydroxylase inhibitor that prevents 6-hydroxydopamine-induced degenerative neuronal disease. However, the effect of PTTU on melanogenesis has not been reported. In this study, we examined the effect of PTTU on melanogenesis and studied its mechanism of action. We found that PTTU decreased melanin biosynthesis in a dose-dependent manner in normal human epidermal melanocytes (NHEMs). PTTU also inhibited tyrosinase catalytic activity in NHEMs. Moreover, PTTU treatment led to reduced protein levels of tyrosinase in NHEMs, while the protein levels of tyrosinase-related protein-1, tyrosinase-related protein-2, and microphthalmia-associated transcription factor were not affected. However, PTTU treatment did not affect the mRNA expression of tyrosinase. We found that PTTU-accelerated tyrosinase degradation via the ubiquitin-dependent proteasome pathway. In summary, we found that PTTU decreased melanin biosynthesis by decreasing the enzymatic activity and stability of tyrosinase. Our results indicate that PTTU could be used as a depigmentation agent for hyperpigmentation disorder. PMID:27278925

  12. Structural motifs of 2-(2-fluoro-phenyl)-ethylamine conformers.

    PubMed

    Mayorkas, Nitzan; Sachs, Hanan; Schütz, Markus; Ishiuchi, Shun-ichi; Fujii, Masaaki; Dopfer, Otto; Bar, Ilana

    2016-01-14

    Vibronic and vibrational spectra of 2-(2-fluoro-phenyl)-ethylamine (2-FPEA) conformers were measured in a molecular beam by resonant two-photon ionization (R2PI), ultraviolet-ultraviolet hole burning (UV-UV HB) spectroscopy, and ionization-loss stimulated Raman spectroscopy (ILSRS). The measured ILSR spectral signatures in the survey spectra of the amino group region and in the broad spectral range revealed the presence of five different conformers, which were confirmed by the HB spectra. The determination of the structures of the conformers of 2-FPEA was assisted by quantum chemical calculations of the torsional potential energy surface and of the scaled harmonic Raman spectra. Comparison of the measured ILSR spectra with the calculated Raman spectra allowed us to identify one gauche structure with the ethylamino side chain folded toward the fluorine atom, two gauche structures with the ethylamino side chain folded to the opposite side and two anti conformers with extended tails. The effect of fluorination on the spectra and on the stability and structures of these species is discussed. PMID:26660487

  13. (R)-1-Phenyl­ethyl­ammonium trifluoro­acetate

    PubMed Central

    Hernández Linares, María-Guadalupe; Guerrero Luna, Gabriel; Bernès, Sylvain

    2010-01-01

    In the crystal structure of the title salt, C8H12N+·C2F3O2 −, all of the ammonium H atoms serve as donors for hydrogen bonds to carboxyl­ate O atoms, forming an R 4 3(10) ring motif based on two cations and two anions. Since both cations and anions act as inter-ion bridging groups, R(10) rings aggregate in a one-dimensional supra­molecular network by sharing the strongest N—H⋯O bond. Edge-sharing motifs lie on the twofold screw axis parallel to [010], and anti­parallel packing of these 21-column structural units results in the crystal structure. This arrangement is one of the most commonly occurring in conglomerates of chiral 1-phenyl­ethyl­amine with achiral monocarboxylic acids, confirming that these ionic salts are particularly robust supra­molecular heterosynthons useful in crystal engineering. PMID:21579169

  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. Sortase inhibitor phenyl vinyl sulfone inhibits Renibacterium salmoninarum adherence and invasion of host cells.

    PubMed

    Sudheesh, Ponnerassery S; Crane, Samuel; Cain, Kenneth D; Strom, Mark S

    2007-12-13

    Renibacterium salmoninarum, the causative agent of bacterial kidney disease in salmonid fishes, is a Gram-positive diplococcobacillus belonging to the family Micrococcaceae. Analysis of the genome sequence of the bacterium demonstrated the presence of a sortase homolog (srtD), a gene specifying an enzyme found in Gram-positive bacteria and required for covalent anchoring of cell surface proteins. Interference of sortase activity is being examined as a target for therapeutic prevention of infection by several pathogenic Gram-positive bacterial species. In silico analysis identified 8 open reading frames containing sortase recognition motifs, suggesting these proteins are translocated to the bacterial cell wall. The sortase and potential sortase substrate genes are transcribed in R. salmoninarum, suggesting they encode functional proteins. Treatment of R. salmoninarum with phenyl vinyl sulfone (PVS) significantly reduced bacterial adherence to Chinook salmon fibronectin. In addition, the ability of the PVS-treated bacteria to adhere to Chinook salmon embryo cells (CHSE-214) in vitro was dramatically reduced compared to that of untreated bacteria. More importantly, PVS-treated bacteria were unable to invade and replicate within CHSE-214 cells (demonstrated by an intracellular growth assay and by light microscopy). When treated with PVS, R. salmoninarum was not cytopathic to CHSE-214 cells, whereas untreated bacteria produced cytopathology within a few days. These findings clearly show that PVS, a small molecule drug and a known sortase inhibitor, can interfere with the ability of R. salmoninarum to adhere and colonize fish cells, with a corresponding decrease in virulence. PMID:18286808

  16. 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.

  17. 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. PMID:19054613

  18. (4-Chloro-acetanilido-κ(2)N,O)bis-[2-(pyridin-2-yl)phenyl-κ(2)C(1),N]iridium(III).

    PubMed

    Sun, Lijun; Zhang, Songlin; Song, Qijun

    2013-02-01

    In the neutral mononuclear iridium(III) title compound, [Ir(C(8)H(7)ClNO)(C(11)H(8)N)(2)], the Ir(III) atom adopts an octa-hedral geometry, and is coordinated by two 2-phenyl-pyridyl ligands and one anionic 4-chloro-acetanilide ligand. The 2-phenyl-pyridyl ligands are arranged in a cis-C,C' and cis-N,N' fashion. Each 2-phenyl-pyridyl ligand forms a five-membered ring with the Ir(III) atom. The 2-phenyl-pyridyl planes are perpendicular to each other [dihedral angle = 89.9 (1)°]. The Ir-C and Ir-N bond lengths are comparable to those reported for related iridium(III) 2-phenyl-pyridyl complexes. The remaining two coordination sites are occupied by the amidate N and O atoms, which form a four-membered ring with the iridium atom (Ir-N-C-O). The amidate plane is nearly perpendicular to both 2-phenyl-pyridyl ligands [dihedral angles = 87.8 (2) and 88.3 (2)°]. PMID:23424440

  19. The C-F...F-C short contacts in the metal complexes of fluoro-phenyl-acrylic acids

    SciTech Connect

    Liu Guilei; Liu CaiMing; Li Hui

    2011-03-15

    Four new complexes of fluoro-phenyl-acrylic acids (E)-3-(3-fluoro-phenyl)-acrylic acid (L1) [Mn{sub 3}(L1){sub 6}(L2){sub 2}].H{sub 2}O.CH{sub 3}CN (1), [Zn{sub 2}(L1){sub 4}(L3)]{sub n} (2), [Mn(L1){sub 2}(H{sub 2}O){sub 2}]{sub n} (3) and [Co(L1){sub 2}(H{sub 2}O){sub 2}]{sub n} (4) (L2=1,10-phenanthroline, L3=4,4'-bipy) have been synthesized based on the molecular design and research of halogen-halogen interactions (especially fluoro-fluoro contact). The structure analyses reveal that complex 1 is a trinuclear complex, which is blocked by L2. Complex 2 is a 1D chain bridged through L3. Complexes 3 and 4 exhibit 2D grid like metal-organic framework structures through carboxylato bridge ligand. Variable-temperature magnetic measurements showed an antiferromagnetic interaction between Mn(II) ions and between Co(II) ions in complexes 3 and 4, respectively. A short C-F...F-C contact with a distance of 2.953 A was found between the trinuclear coordination compound 1. -- Graphical Abstract: The short distance between F...F (2.953 A) was found in the complex of [Mn{sub 3}(L1){sub 6}(L2){sub 2}].H{sub 2}O.CH{sub 3}CN (L1=(E)-3-(3-fluoro-phenyl)-acrylic acid, L2=1,-10-phenanthroline). Display Omitted Research highlights: > Four new complexes of fluoro-phenyl-acrylic acids (E)-3-(3-fluoro-phenyl)-acrylic acid (L1) [Mn{sub 3}(L1){sub 6}(L2){sub 2}].H{sub 2}O.CH{sub 3}CN (1), [Zn{sub 2}(L1){sub 4}(L3)]{sub n} (2), [Mn(L1){sub 2}(H{sub 2}O){sub 2}]{sub n} (3) and [Co(L1){sub 2}(H{sub 2}O){sub 2}]{sub n} (4) (L2=1,10-phenanthroline, L3=4,4'-bipy) have been synthesized based on the molecular design and research of halogen-halogen interactions (especially fluoro-fluoro contact). > A short C-F...F-C contact with a distance of 2.953 A was found between the trinuclear coordination compound 1. > Variable-temperature magnetic measurements showed an antiferromagnetic interaction between Mn(II) ions and between Co(II) ions in complexes 3 and 4, respectively.

  20. 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.

  1. Mechanism and specificity of a symmetrical benzimidazole-phenyl-carboxamide helicase inhibitor

    PubMed Central

    Belon, Craig A.; High, Yoji D.; Lin, Tse-I; Pauwels, Frederik; Frick, David N.

    2010-01-01

    This study examines the effects of 1-N,4-N-bis[4-(1H-benzimidazol-2-yl)phenyl]benzene-1,4-dicarboxamide ((BIP)2B) on the NS3 helicase encoded by the hepatitis C virus (HCV). Molecular beacon-based helicase assays were used to show that (BIP)2B inhibits the ability of HCV helicase to separate a variety of RNA and DNA duplexes with half maximal inhibitory concentrations ranging from 0.7 to 5 μM, depending on the nature of the substrate. In single turnover assays, (BIP)2B only inhibited unwinding reactions when it was pre-incubated with the helicase-nucleic acid complex. (BIP)2B quenched NS3 intrinsic protein fluorescence with an apparent dissociation constant of 5 μM, and in the presence of (BIP)2B, HCV helicase did not appear to interact with a fluorescent DNA oligonucleotide. In assays monitoring HCV helicase-catalyzed ATP hydrolysis, (BIP)2B only inhibited helicase-catalyzed ATP hydrolysis in the presence of intermediate concentrations of RNA, suggesting RNA and (BIP)2B compete for the same binding site. HCV helicases isolated from various HCV genotypes were similarly sensitive to (BIP)2B, with half maximal inhibitory concentrations ranging from 0.7 to 2.4 μM. (BIP)2B also inhibited ATP hydrolysis catalyzed by related helicases from Dengue virus, Japanese encephalitis virus and humans. (BIP)2B appeared to bind the HCV and human proteins with similar affinity (Ki = 7 and 8 μM respectively), but it bound the flavivirus proteins up to 270 times more tightly. Results are discussed in light of a molecular model of a (BIP)2B-HCV helicase complex, which is unable to bind nucleic acid, thus preventing the enzyme from separating double stranded nucleic acid. PMID:20108979

  2. 1-phenyl-2-decanoylamino-3-morpholino-1-propanol chemosensitizes neuroblastoma cells for taxol and vincristine.

    PubMed

    Sietsma, H; Veldman, R J; Kolk, D; Ausema, B; Nijhof, W; Kamps, W; Vellenga, E; Kok, J W

    2000-03-01

    In this study, we show that an inhibitor of glycosphin-golipid biosynthesis, D,L-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP), increases the chemosensitivity of neuroblastoma tumor cells for Taxol and vincristine. At noneffective low doses of Taxol or vincristine, the addition of a noneffective dose of PDMP resulted in 70% cytotoxicity, indicating synergy. Such an effect was not observed for etoposide (VP16). PDMP caused an early (6 h) increase in ceramide (Cer) levels, but the excess Cer was metabolically removed in the long-term (96 h). However, upon incubation with PDMP in combination with Taxol, but not with etoposide, Cer levels remained elevated at 96 h. These results suggest that neuroblastoma cells are normally able to metabolically remove excess Cer, but lose this capacity upon exposure to microtubule modulating anticancer agents (Taxol or vincristine). In addition, PDMP treatment resulted in a decreased efflux of [14C]Taxol and [3H]vincristine from neuroblastoma cells, similar to treatment with PSC833 or MK571, suggesting an effect of PDMP on the transporter proteins P-glycoprotein and/or multidrug resistance protein. PDMP did not further reduce [14C]Taxol or [3H]vincristine efflux in PSC833-treated cells, although it did further diminish cell survival under these conditions. We conclude that a combined administration of nontoxic concentrations of PDMP and either Taxol or vincristine results in highly sensitized neuroblastoma cells. This appears to involve a sustained elevation of Cer levels, possibly in concert with increased drug accumulation. PMID:10741719

  3. Electrospray liquid chromatography quadrupole ion trap mass spectrometry determination of phenyl urea herbicides in water.

    PubMed

    Draper, W M

    2001-06-01

    Phenyl urea herbicides were determined in water by electrospray quadrupole ion trap liquid chromatography-mass spectrometry (ES-QIT-LC-MS). Over a wide concentration range [M - H](-) and MH(+) ions were prominent in ES spectra. At high concentrations dimer and trimer ions appeared, and sodium, potassium, and ammonium adducts also were observed. In the case of isopturon, source collision-induced dissociation (CID) fragmentation with low offset voltages increased the ion current associated with MH(+) and diminished dimer and trimer ion abundance. In the mass analyzer CID involved common pathways, for example, daughter ions of [M - H](-) resulted from loss of R(2)NH in N',N'-dialkyl ureas or loss of C(3)H(5)NO(2) (87 amu) in N'-methoxy ureas. A 2 mm (i.d.) x 15 cm C(18) reversed phase column was used for LC-MS with a linear methanol/water gradient and 0.5 mL/min flow rate. Between 1 and 100 pg/microg/L the response was highly linear with instrument detection limits ranging from <10 to 50 pg injected. Whereas the positive ES signal intensity was greater for each of the compounds except fluometuron, negative ion monitoring gave the highest signal-to-noise ratio. Analysis of spiked Colorado River water, a source high in total dissolved solids and total organic carbon, demonstrated that ES-QIT-LC-MS was routinely capable of quantitative analysis at low nanogram per liter concentrations in conjunction with a published C(18) SPE method. Under these conditions experimental method detection limits were between 8.0 and 36 ng/L, and accuracy for measurements in the 20-50 parts per trillion range was from 77 to 96%. Recoveries were slightly lower in surface water (e.g., 39-76%), possibly due to suppression of ionization. PMID:11409961

  4. 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.

  5. 1H and 13C NMR spectra, structure and physicochemical features of phenyl acridine-9-carboxylates and 10-methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulphonates--alkyl substituted in the phenyl fragment.

    PubMed

    Krzymiński, K; Malecha, P; Zadykowicz, B; Wróblewska, A; Błażejowski, J

    2011-01-01

    The 1H and 13C NMR spectra of twelve phenyl acridine-9-carboxylates--alkyl-substituted in the phenyl fragment--and their 10-methyl-9-(phenoxycarbonyl)acridinium salts dissolved in CD3CN, CD3OD, CDCl3 and DMSO-d6 were recorded in order to examine the influence of the structure of these compounds and the properties of the solvents on chemical shifts and 1H-(1)H coupling constants. Experimental data were compared with 1H and 13C chemical shifts predicted at the GIAO/DFT level of theory for DFT(B3LYP)/6-31G** optimised geometries of molecules, as well as with values of 1H chemical shifts and 1H-(1)H coupling constants, estimated using ACD/HNMR database software to ensure that the assignment was correct. To investigate the relations between chemical shifts and selected structural or physicochemical characteristics of the target compounds, the values of several of these parameters were determined at the DFT or HF levels of theory. The HOMO and LUMO energies obtained at the HF level yielded the ionisation potentials and electron affinities of molecules. The DFT method provided atomic partial charges, dipole moments, LCAO coefficients of pz LUMO of selected C atoms, and angles reflecting characteristic structural features of the compounds. It was found that the experimentally determined 1H and 13C chemical shifts of certain atoms relate to the predicted dipole moments, the angles between the acridine and phenyl moieties, and the LCAO coefficients of the pz LUMO of the C atoms believed to participate in the initial step of the oxidation of the target compounds. The spectral and physicochemical characteristics of the target compounds were investigated in the context of their chemiluminogenic ability. PMID:21134782

  6. Synthesis and biological evaluation of novel 9-heteroaryl substituted 7-chloro-4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates (TQX) as (R,S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptor antagonists.

    PubMed

    Catarzi, Daniela; Colotta, Vittoria; Varano, Flavia; Filacchioni, Guido; Gratteri, Paola; Sgrignani, Jacopo; Galli, Alessandro; Costagli, Chiara

    2008-08-01

    In this paper, we report a study on some new 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylate derivatives (TQXs), bearing a nitrogen-containing heterocycle at position-9, and designed as (R,S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptor antagonists. These compounds ensue from the structural modification of previously reported 8-heteroaryl-TQXs which were endowed with high affinity and selectivity for the AMPA receptor. All the newly synthesized compounds were biologically evaluated for their binding at the AMPA receptor. Gly/N-methyl-D-aspartic acid (NMDA) and kainic acid (KA) high-affinity binding assays were performed to assess the selectivity of the reported derivatives toward the AMPA receptor. This study produced some new TQXs which are less potent than the reference compounds, and endowed with a mixed AMPA and Gly/NMDA receptor binding affinity. To rationalize the experimental findings, a molecular modeling study was performed by docking some TQX derivatives to the AMPA receptor model. PMID:18670107

  7. 3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione

    PubMed Central

    Al-Abdullah, Ebtehal S.; Asiri, Hanadi H.; El-Emam, Ali; Ng, Seik Weng

    2012-01-01

    The title mol­ecule, C29H35N5S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring (r.m.s. deviation = 0.001 Å) whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring [dihedral angle = 88.9 (1)°]. The substituents on the piperazine ring occupy equatorial sites. In the crystal, the adamantyl cage is disordered over two sets of sites with a major component of 67.8 (5)%. Weak inter­molecular C—H⋯S hydrogen bonding is present in the crystal. PMID:22346974

  8. (1R,3R,3aS,8aR)-4-Oxo-3-phenyl-1-[(1R)-1-phenyl­eth­yl]deca­hydro­cyclo­hepta­[b]pyrrol-1-ium bromide

    PubMed Central

    Rybakov, Victor B.; Belov, Dmitry S.; Lukyanenko, Evgeny R.; Kurkin, Alexander V.; Yurovskaya, Marina A.

    2012-01-01

    The title chiral compound, C23H28NO+·Br−, was obtained from an optically active amino­ethanol precursor. The pyrrolidine heterocycle has an envelope conformation, with the C atom α-positioned with respect to the keto group deviating by 0.570 (6) Å from the mean plane of other atoms. The trans-fused seven-membered ring adopts a pseudo-chair conformation. The two phenyl rings form a dihedral angle of 85.1 (2)°. The cationic center and the bromide anion are connected through an N—H⋯Br hydrogen bond. PMID:22798884

  9. 40 CFR 721.5288 - Chromate(2-), [3-hydroxy-4-[(2-hydroxy-1-naphthenyl)azo]-7-nitro-1-substituted][N-[7-hydroxy-8...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Chromate(2-), -7-nitro-1-substituted... Significant New Uses for Specific Chemical Substances § 721.5288 Chromate(2-), -7-nitro-1-substituted] -1... chemical substance identified generically as chromate(2-), -7- nitro-1-substituted] -1-substituted]-,...

  10. 40 CFR 721.5288 - Chromate(2-), [3-hydroxy-4-[(2-hydroxy-1-naphthenyl)azo]-7-nitro-1-substituted][N-[7-hydroxy-8...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Chromate(2-), -7-nitro-1-substituted... Significant New Uses for Specific Chemical Substances § 721.5288 Chromate(2-), -7-nitro-1-substituted] -1... chemical substance identified generically as chromate(2-), -7- nitro-1-substituted] -1-substituted]-,...

  11. 40 CFR 721.5288 - Chromate(2-), [3-hydroxy-4-[(2-hydroxy-1-naphthenyl)azo]-7-nitro-1-substituted][N-[7-hydroxy-8...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Chromate(2-), -7-nitro-1-substituted... Significant New Uses for Specific Chemical Substances § 721.5288 Chromate(2-), -7-nitro-1-substituted] -1... chemical substance identified generically as chromate(2-), -7- nitro-1-substituted] -1-substituted]-,...

  12. 40 CFR 721.5288 - Chromate(2-), [3-hydroxy-4-[(2-hydroxy-1-naphthenyl)azo]-7-nitro-1-substituted][N-[7-hydroxy-8...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Chromate(2-), -7-nitro-1-substituted... Significant New Uses for Specific Chemical Substances § 721.5288 Chromate(2-), -7-nitro-1-substituted] -1... chemical substance identified generically as chromate(2-), -7- nitro-1-substituted] -1-substituted]-,...

  13. 40 CFR 721.5288 - Chromate(2-), [3-hydroxy-4-[(2-hydroxy-1-naphthenyl)azo]-7-nitro-1-substituted][N-[7-hydroxy-8...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Chromate(2-), -7-nitro-1-substituted... Significant New Uses for Specific Chemical Substances § 721.5288 Chromate(2-), -7-nitro-1-substituted] -1... chemical substance identified generically as chromate(2-), -7- nitro-1-substituted] -1-substituted]-,...

  14. Pulse radiolysis study on free radical scavenger edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one). 2: A comparative study on edaravone derivatives.

    PubMed

    Hata, Kuniki; Lin, Mingzhang; Katsumura, Yosuke; Muroya, Yusa; Fu, Haiying; Yamashita, Shinichi; Nakagawa, Hidehiko

    2011-01-01

    A comparative study using the pulse radiolysis technique was carried out to investigate transient absorption spectra and rate constants for the reactions of (•)OH and N(3)(•) with edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) and its four analogue compounds, 1,3-dimethyl-2-pyrazolin-5-one, 3-methyl-1-(pyridin-2-yl)-2-pyrazolin-5-one, 1-phenyl-3-trifluoromethyl-2-pyrazolin-5-one and 1-(4-chlorophenyl)-3-methyl-2-pyrazolin-5-one. The results showed that, unlike reaction mechanisms previously proposed, the phenyl group of edaravone played an important role in the reaction with (•)OH and OH adducts to the phenyl group were formed. Quantum chemical calculations also strongly supported this attribution and suggested that the most favorable site for attacks by (•)OH is the ortho position of the phenyl group. Moreover, the rate constants for the reactions of edaravone and its analogues towards (•)OH and N(3)(•) were about 8.0 × 10(9), and 4.0 × 10(9) dm(3) mol(-1) s(-1), respectively. Edaravone displayed higher reactivity compared to the others, in contrast to a previous report in which 3-methyl-1-(pyridin-2-yl)-2-pyrazolin-5-one showed the highest reactivity towards (•)OH. PMID:21139328

  15. Phenyl Substituted 4-Hydroxypyridazin-3(2H)-ones and 5-Hydroxypyrimidin-4(3H)-ones: Inhibitors of Influenza A Endonuclease

    PubMed Central

    2015-01-01

    Seasonal and pandemic influenza outbreaks remain a major human health problem. Inhibition of the endonuclease activity of influenza RNA-dependent RNA polymerase is attractive for the development of new agents for the treatment of influenza infection. Our earlier studies identified a series of 5- and 6-phenyl substituted 3-hydroxypyridin-2(1H)-ones that were effective inhibitors of influenza endonuclease. These agents identified as bimetal chelating ligands binding to the active site of the enzyme. In the present study, several aza analogues of these phenyl substituted 3-hydroxypyridin-2(1H)-one compounds were synthesized and evaluated for their ability to inhibit the endonuclease activity. In contrast to the 4-aza analogue of 6-(4-fluorophenyl)-3-hydroxypyridin-2(1H)-one, the 5-aza analogue (5-hydroxy-2-(4-fluorophenyl)pyrimidin-4(3H)-one) did exhibit significant activity as an endonuclease inhibitor. The 6-aza analogue of 5-(4-fluorophenyl)-3-hydroxypyridin-2(1H)-one (6-(4-fluorophenyl)-4-hydroxypyridazin-3(2H)-one) also retained modest activity as an inhibitor. Several varied 6-phenyl-4-hydroxypyridazin-3(2H)-ones and 2-phenyl-5-hydroxypyrimidin-4(3H)-ones were synthesized and evaluated as endonuclease inhibitors. The SAR observed for these aza analogues are consistent with those previously observed with various phenyl substituted 3-hydroxypyridin-2(1H)-ones. PMID:25225968

  16. 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. PMID:24446265

  17. Design, Synthesis, and Biological Evaluation of New 2-Phenyl-4H-chromen-4-one Derivatives as Selective Cyclooxygenase-2 Inhibitors.

    PubMed

    Zarghi, Afshin; Kakhki, Samaneh

    2015-01-01

    In order to develop new selective COX-2 inhibitors, a new series of 2-phenyl-4H-chromen-4-one derivatives possessing a methylsulfonyl pharmacophore group at the para position of the C-4 phenyl ring were designed, synthesized, and evaluated for cyclooxygenase-2 inhibitory activity. In vitro COX-1/COX-2 isozyme inhibition structure-activity studies identified 3-(benzyloxy)-2-[4-(methylsulfonyl)phenyl]-4H-chromen-4-one (5d) as a potent COX-2 inhibitor (IC50 = 0.07 μM) with a high COX-2 selectivity index (SI = 287.1) comparable to the reference drug celecoxib (COX-2 IC50 = 0.06 μM; COX-2 SI = 405). A molecular modeling study where 3-(benzyloxy)-2-[4-(methylsulfonyl)phenyl]-4H-chromen-4-one (5d) was docked into the active site of COX-2 showed that the p-MeSO2 substituent on the C-4 phenyl ring was well-oriented in the vicinity of the COX-2 secondary pocket (Arg(513), Val(523), and His(90)) and the carbonyl group of the chromene ring could interact with Ser(530). The structure-activity data acquired indicated that the nature and size of the substituent on the C-3 chromene scaffold are important for COX-2 inhibitory activity. Our results also indicated that the chromene moiety constitutes a suitable template to design new COX-2 inhibitors. PMID:26839798

  18. In-gel staining of proteins in native poly acryl amide gel electrophoresis using tetrakis(4-sulfonato phenyl)porphyrin.

    PubMed

    Divakar, Kalivarathan; Sujatha, Vijayan; Barath, Sridhar; Srinath, Krishnamurthy; Gautam, Pennathur

    2011-01-01

    Protein identification in polyacrylamide gel electrophoresis (PAGE) requires post-electrophoretic steps like fixing, staining and destaining of the gel, which are time-consuming and cumbersome. We have developed a method for direct visualization of protein bands in PAGE using tetrakis(4-sulfonato phenyl)porphyrin (TPPS) as a dye without the need for any post electrophoretic steps, where separation and recovery of enzymes become much easier for further analysis. Activity staining was done to prove that the biochemical activity of the enzymes was preserved after electrophoresis. PMID:21233569

  19. (E)-2,2-Dimethyl-5-(3-phenyl-allyl-idene)-1,3-dioxane-4,6-dione.

    PubMed

    Zeng, Wu-Lan

    2010-01-01

    The title compound, C(15)H(14)O(4), was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and (Z)-3-phenyl-acryl-aldehyde in ethanol. The dioxane ring is in a sofa conformation with the C atom bonded to the two methyl groups forming the flap. With the exception of the flap atom and the methyl group C atoms, all other non-H atoms are essentially planar, with an r.m.s. deviation of 0.067 (1) Å. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds. PMID:21589113

  20. Conformation and coordination of 1-phenyl-3-methyl-4-benzal-5-pyrazolone thiosemicarbazone: A density functional study

    NASA Astrophysics Data System (ADS)

    Wu, Dongling; Jia, Dianzeng; Liu, Lang; Liu, Anjie

    Density functional theory method has been employed to study the molecular properties of four tautomers and their deprotonated species of 1-phenyl-3-methyl-4-benzal-5-pyrazolone thiosemicarbazone. The solvent effect has been investigated by applying the polarizable continuum model of the self-consistent reaction field theory. The condensed Fukui functions have been calculated to assess the relative reactivity of different sites in the ligands. Molecular electrostatic potential is obtained as an additional molecular descriptor for revealing the regions of the molecular species to which an electrophile would initially be attracted.

  1. Crystal structure of 2-amino-4-phenyl-4H-benzo[h]chromene-3-carbo­nitrile

    PubMed Central

    Mohamed, Shaaban K.; Horton, Peter N.; Akkurt, Mehmet; Younes, Sabry H. H.; Albayati, Mustafa R.

    2015-01-01

    In the title compound, C20H14N2O, the plane of the phenyl ring is almost normal to that of the naphthalene ring system, forming a dihedral angle of 83.15 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, mol­ecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(12) ring motif. The dimers are connected by C—H⋯π inter­actions, forming supra­molecular chains along [010]. PMID:26279939

  2. Crystal structure of 2-[4-(methyl­sulfan­yl)quinazolin-2-yl]-1-phenyl­ethanol

    PubMed Central

    El-Hiti, Gamal A.; Smith, Keith; Hegazy, Amany S.; Ajarim, Mansour D.; Kariuki, Benson M.

    2014-01-01

    In the mol­ecule of the title compound, C17H16N2OS, the almost planar methyl­sulfanylquinazoline group [the methyl C atom deviates by 0.032 (2) Å from the plane through the ring system] forms an inter­planar angle of 76.26 (4)° with the plane of the phenyl group. An intra­molecular O—H⋯N hydrogen bond is present between the quinazoline and hy­droxy groups. In the crystal, mol­ecules are stacked along the b-axis direction. PMID:25484694

  3. Cathodic delaminations of poly(phenyl ether ether ketone) (PEEK) coatings overlaid on zinc phosphate-deposited steels

    SciTech Connect

    Sugama, T.; Carciello, N.R. . Dept. of Applied Science)

    1993-12-10

    The melt-crystallized poly(phenyl) ether ether ketone (PEEK) polymer was overlaid on crystalline zinc phosphate (Zn [center dot] Ph) conversion coating-deposited and nondeposited cold-rolled steels at 400 C in air or in N[sub 2] environments. The ability of these coatings systems to protect the steel against corrosion was evaluated from the rate of cathodic delamination of the coating layer from the steel. Because the cathodic reaction, H[sub 2]O + 1/20[sub 2] + 2e[sup [minus

  4. X-ray diffraction and spectral studies of 1-phenyl-3-methyl-4-(2',4'-dimethylphenylazo)-pyrazolone-5

    SciTech Connect

    Kuz'mina, L.G.; Grigor'eva, L.P.; Struchkov, Yu.T.; Ezhkova, Z.I.; Zaitsev, B.E.; Zaitseva, V.A.; Pron'kin, P.P.

    1985-12-01

    The molecular and crystal structures of 1-phenyl-3-methyl-4-(2',4'-dimethyl-phenylazo)pyrazolone-5 were determined. In the crystal the molecule exists as the hydrazone tautomer. The pyrazole ring is planar, and the substituents are practically coplanar with it. The molecule contains an intramolecular NH...O hydrogen bond that closes a practically planar six-membered ring (N...O, 2.77 (I), H...O 2.14 A, angle at H(N/sub (4)/) hydrogen 131/sup 0/). The x-ray diffraction data agree with the spectral data and with the CNO calculation.

  5. Gas and hydrocarbon vapor permeation in poly(1-trimethylsilyl-1-propyne)/poly(1-phenyl-1-propyne) blends

    SciTech Connect

    Morisato, A.; Shen, H.C.; Toy, L.G.

    1996-12-31

    Permeation properties of phase-separated blends prepared from glassy poly(1-trimethylsilyl-1-propyne) (PTMSP) and poly(1-phenyl-1-propyne) (PPP) were determined as a function of blend composition with pure hydrogen, nitrogen, oxygen, carbon dioxide, and butane. Blend permeabilities decrease significantly with increasing PPP concentration and suggest the occurrence of a phase inversion at low PPP content (5 to 20 wt%). Based on TEM analysis high-aspect-ratio (extended) PPP ellipsoidal dispersions are found in a PTMSP matrix, indicating that the phase inversion is closely related to dispersed-phase connectivity in the blends.

  6. Extraction of actinides and fission products by octyl(phenyl)-N,N-diisobutylcarbamoylmethyl-phosphine oxide from nitric acid media.

    PubMed

    Mathur, J N; Murali, M S; Natarajan, P R; Badheka, L P; Banerji, A

    1992-05-01

    Extraction of promethium(III), uranium(VI), plutonium(IV), americium(III), zirconium(IV), ruthenium(III), iron(III) and palladium(II) has been carried out with a mixture of octyl(phenyl)-N,N-diisobutylcarbamoylmethylphosphine oxide (CMPO) and tributyl phosphate (TBP) in dodecane. The effects of nitric acid, TBP and CMPO concentrations on the extraction of these metal ions have been studied. The nature of the species of the above metal ions extracted into the organic phase has been suggested. PMID:18965406

  7. 3,4,6-Trimethyl-1-phenyl-1H-pyrazolo­[3,4-b]pyridine

    PubMed Central

    Hamri, Salha; Hafid, Abderrafia; Zouihri, Hafid; Lazar, Saïd; Khouili, Mostafa

    2010-01-01

    In the title compound, C15H15N3, the 1H-pyrazolo­[3,4-b]pyridine system and the phenyl ring are each individually planar, with r.m.s. deviations of 0.017 (2) and 0.011 (2) Å, respectively; the dihedral angle between the two aromatic systems is 9.33 (10)°. The crystal packing is stabilized by offset π–π stacking between parallel pyrazolo­[3,4-b]pyridine ring systems [face-to-face distance = 3.449 (6) Å]. PMID:21588287

  8. Synthesis, characterization, thermal properties and antiproliferative potential of copper(ii) 4'-phenyl-terpyridine compounds.

    PubMed

    Ma, Zhen; Zhang, Bian; Guedes da Silva, M Fátima C; Silva, Joana; Mendo, Ana Soraia; Baptista, Pedro Viana; Fernandes, Alexandra R; Pombeiro, Armando J L

    2016-03-15

    Reactions between 4'-phenyl-terpyridine (L) and several Cu(ii) salts (p-toluenesulfonate, benzoate and o-, m- or p-hydroxybenzoate) led to the formation of [Cu(p-SO3C6H4CH3)L(H2O)2](p-SO3C6H4CH3) (), [Cu(OCOPh)2L] (), [Cu(o-OCOC6H4OH)2L] (), [Cu(m-OCOC6H4OH)2L]·MeOH (·MeOH) and [Cu(p-OCOC6H4OH)2L]·2H2O (·2H2O), which were characterized by elemental and TG-DTA analyses, ESI-MS, IR spectroscopy and single crystal X-ray diffraction, as well as by conductivimetry. In all structures the Cu atoms present N3O3 octahedral coordination geometries, which, in , are highly distorted as a result of the chelating-bidentate mode of one of the carboxylate ligands. Intermolecular ππ stacking interactions could also be found in (in the 3.569-3.651 Å range and involving solely the pyridyl rings). Medium-strong hydrogen bond interactions lead to infinite 1D chains (in and ) and to an infinite 2D network (in ). Compounds and show high in vitro cytotoxicity towards HCT116 colorectal carcinoma and HepG2 hepatocellular carcinoma cell lines. The antiproliferative potential of compound is due to an increase of the apoptotic process that was confirmed by Hoechst staining, flow cytometry and RT-qPCR. All compounds able to non-covalently intercalate the DNA helix and induce in vitro pDNA double-strand breaks in the absence of H2O2. Concerning compound , the hydroxyl radical and singlet oxygen do not appear to be involved in the pDNA cleavage process and the fact that this cleavage also occurs in the absence of molecular oxygen points to a hydrolytic mechanism of cleavage. PMID:26905013

  9. 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).

  10. Preparation and properties of (R)-(-)-1-azabicyclo(2. 2. 2)oct-3-yl- (R)-(+)-alpha-hydroxy-alpha-(4-( sup 125 I)iodophenyl)-alpha-phenyl acetate and (R)-(-)-1-azabicyclo(2. 2. 2)oct-3-yl-(S)-(-)-alpha-hydroxy-alpha- (4-( sup 125 I)iodophenyl)-alpha-phenyl acetate as potential radiopharmaceuticals

    SciTech Connect

    Cohen, V.I.; Rzeszotarski, W.J.; Gibson, R.E.; Fan, L.H.; Reba, R.C. )

    1989-10-01

    rac-4-Nitrobenzilic acid was synthesized and resolved with quinidine and quinine to give the corresponding (R)- and (S)-salts. The resolved diastereomeric salts were converted to (R)- and (S)-4-nitrobenzilic acids and subsequent esterification gave their corresponding ethyl esters. Transesterification with (R)-(-)-3-quinuclidinol afforded (R)-(-)-1-azabicyclo(2.2.2)oct-3-yl-(R)-(+)-alpha-hydroxy-alpha- (4-nitrophenyl)-alpha-phenyl acetate and (R)-(-)-1-azabicyclo(2.2.2)oct-3-yl-(S)-(-)-alpha-hydroxy- alpha-(4-nitrophenyl)-alpha-phenyl acetate. After hydrogenation, the (R,R)- and (R,S)-amines were converted to the respective triazene derivatives. The triazene derivatives reacted with sodium ({sup 125}I)iodide to give (R)-(-)-1-azabicyclo(2.2.2)oct-3-yl-(R)-(+)- alpha-hydroxy-alpha-(4-({sup 125}I)iodophenyl)-alpha-phenyl acetate and (R)-(-)-1-azabicyclo(2.2.2)oct-3-yl-(S)-(-)-alpha-hydroxy- alpha-(4-(125I)iodophenyl)-alpha-phenyl acetate. The evaluation of their affinities to muscarinic acetylcholine receptors (MAcChR) shows that (R)-(-)-1-azabicyclo(2.2.2)oct-3-yl-(S)-(-)-alpha-hydroxy-alpha-(4- ({sup 125}I)iodophenyl)-alpha-phenyl acetate exhibits an affinity for the MAcChR from corpus striatum that is approximately threefold lower than that of (R)-(-)-1-azabicyclo(2.2.2)oct-3-yl-(R)-(+)-alpha-hydroxy-alpha-(4- ({sup 125}I)iodophenyl)-alpha-phenyl acetate.

  11. 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

    2014-05-01

    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. PMID:24548812

  12. 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. PMID:27308054

  13. 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.

  14. 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.

  15. Synthesis, structural characterization, in-vitro antibiogram assay and efficient catalytic activities of transition metal(II) chelates incorporating (E)-(2-((2-hydroxybenzylidene)amino)phenyl)(phenyl)methanone ligand

    NASA Astrophysics Data System (ADS)

    Muniyandi, Vellaichamy; Pravin, Narayanaperumal; Mitu, Liviu; Raman, Natarajan

    2015-04-01

    A new tridentate ligand, (E)-(2-((2-hydroxybenzylidene)amino)phenyl)(phenyl)methanone and its four metal(II) chelates have been designed and synthesized. They were structurally characterized by elemental analysis, FT IR, UV-vis, 1H NMR, 13C NMR, mass spectra, EPR, magnetic moment and conductivity measurements. Elemental analysis and molar conductance values reveal that all the chelates are 1:1 stoichiometry of the type [MLCl] having non-electrolytic nature. The metal chelates adopt square planar geometrical arrangements around the metal ions. The DNA-binding properties of these chelates have been investigated by electronic absorption, cyclic voltammetry, differential pulse voltammogram and viscosity measurements. The data indicate that these complexes bind to DNA via an intercalation mode. The oxidative cleavage of the metal complexes with pBR322 DNA has also been investigated by gel electrophoresis. Moreover, the antimicrobial bustle shows that all metal chelates have superior activity than the free ligand. The oxidation of toluene to benzaldehyde is effectively catalyzed by the synthesized chelates.

  16. O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl-oxazolidin-3-yl]propan-2-yl} carbonodi-thio-ate.

    PubMed

    García-Merinos, J Pablo; López-Ruiz, Heraclio; López, Yliana; Rojas-Lima, Susana

    2014-05-01

    In the title compound, C15H17NO4S2, synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro-propano-yl)-4-phenyl-oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C-C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°. In the chain the methine H atom is involved in a C-H⋯S and a C-H⋯O intra-molecular inter-action. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming chains along [001]. The S configuration at the C atom to which the xanthate group is attached was determined by comparison to the known R configuration of the C atom to which the phenyl group is attached. PMID:24860384

  17. Monitoring the Reaction Products of Perfluoropropionic Acid and Allyl Phenyl Ether Using Chirped-Pulse Fourier Transform Microwave Cp-Ftmw Spectroscopy

    NASA Astrophysics Data System (ADS)

    Frank, Derek S.; Obenchain, Daniel A.; Lin, Wei; Novick, Stewart E.; Cooke, S. A.; Grubbs, G. S., II

    2014-06-01

    The pure rotational spectra of the reaction mixture of perfluoropropionic acid, CF3CF2COOH, and allyl phenyl ether, C6H5OCH2CH=CH2, have been studied by a pulsed nozzle, chirped-pulse Fourier transform microwave spectrometer in the frequency range of 8-14 GHz. Transitions corresponding to multiple species, two of which being starting materials allyl phenyl ether and perfluoropropionic acid, have been observed and analyzed. Determination of the reaction products was carried out by matching observed rotational constants with ab initio quantum chemical calculations of predicted products and will be discussed. Rotational constants, centrifugal distortion constants and the assignment of allyl phenyl ether and reaction products spectra will all be discussed.

  18. Second-order nonlinearity and optical image storage in phenyl-silica hybrid films doped with azo-dye chromophore using optical poling technique

    NASA Astrophysics Data System (ADS)

    Matsuoka, Nobuaki; Kitaoka, Kenji; Si, Jinhai; Fujita, Koji; Hirao, Kazuyuki

    2000-11-01

    4-[ N-ethyl- N-(2-hydroxyethyl)]amino-4 '-nitro-azobenzene (DR1)-doped phenyl group substituted silica films were prepared by a sol-gel method. The films were optically poled by the coherent superposition of 1064 and 532 nm beams from a Q-switched Nd:YAG laser. To discuss the effects of the modifier group, interaction between DR1 molecules and the matrix was investigated. The delocalization of π electrons occurred between DR1 molecules and the phenyl-silica hybrid matrix, and that consequently the polarized DR1 molecules could be stabilized. By use of the optimized optical poling technique, optical storage was successfully demonstrated for a phenyl-silica hybrid film doped with DR1.

  19. 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

  20. Binding-induced fluorescence of serotonin transporter ligands: A spectroscopic and structural study of 4-(4-(dimethylamino)phenyl)-1-methylpyridinium (APP(+)) and APP(+) analogues.

    PubMed

    Wilson, James N; Ladefoged, Lucy Kate; Babinchak, W Michael; Schiøtt, Birgit

    2014-04-16

    The binding-induced fluorescence of 4-(4-(dimethylamino)-phenyl)-1-methylpyridinium (APP(+)) and two new serotonin transporter (SERT)-binding fluorescent analogues, 1-butyl-4-[4-(1-dimethylamino)phenyl]-pyridinium bromide (BPP(+)) and 1-methyl-4-[4-(1-piperidinyl)phenyl]-pyridinium (PPP(+)), has been investigated. Optical spectroscopy reveals that these probes are highly sensitive to their chemical microenvironment, responding to variations in polarity with changes in transition energies and responding to changes in viscosity or rotational freedom with emission enhancements. Molecular docking calculations reveal that the probes are able to access the nonpolar and conformationally restrictive binding pocket of SERT. As a result, the probes exhibit previously not identified binding-induced turn-on emission that is spectroscopically distinct from dyes that have accumulated intracellularly. Thus, binding and transport dynamics of SERT ligands can be resolved both spatially and spectroscopically. PMID:24460204