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Sample records for phenyl p-fluorophenyl thienyl-2

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

    PubMed

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

    2013-03-01

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

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

    PubMed

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

    2010-03-01

    The reactions of PbR(2)(OAc)(2) (R = Me, Ph) with 3-(2-thienyl)-2-sulfanylpropenoic acid (H(2)tspa) in methanol or ethanol afforded complexes [PbR(2)(tspa)] that electrospray ionization-mass spectrometry (ESI-MS) and IR data suggest are polymeric. X-ray studies showed that [PbPh(2)(tspa)(dmso)] x dmso, crystallized from a solution of [PbPh(2)(tspa)] in dmso, is dimeric, and that [HQ](2)[PbPh(2)(tspa)(2)] (Q = diisopropylamine), obtained after removal of [PbPh(2)(tspa)] from a reaction including Q, contains the monomeric anion [PbPh(2)(tspa)(2)](2-). In the solid state the lead atoms are O,S-chelated by the tspa(2-) ligands in all these products, and in the latter two have distorted octahedral coordination environments. NMR data suggest that tspa(2-) remains coordinated to PbR(2)(2+) in solution in dmso. Neither thiamine nor thiamine diphosphate reacted with PbMe(2)(NO(3))(2) in D(2)O. Prior addition of H(2)tspa protected LLC-PK1 renal proximal tubule cells against PbMe(2)(NO(3))(2); thiamine had no statistically significant effect by itself, but greatly potentiated the action of H(2)tspa. Administration of either H(2)tspa or thiamine to male albino Sprague-Dawley rats dosed 30 min previously with PbMe(2)(NO(3))(2) was associated with reduced inhibition of delta-ALAD by the organolead compound, and with lower lead levels in kidney and brain, but joint administration of both H(2)tspa and thiamine only lowered lead concentration in the kidney. PMID:20088549

  3. Composite Semiconductor Material of Carbon Nanotubes and Poly[5,5'-bis(3-dodecyl-2-thienyl)-2,2'-bithiophene] for High-Performance Organic Thin-Film Transistors

    NASA Astrophysics Data System (ADS)

    Derry, Cameron; Wu, Yiliang; Zhu, Shiping; Deen, Jamal

    2013-12-01

    A nonpercolating network of non-covalently functionalized single-walled carbon nanotubes was embedded within air-stable poly[5,5'-bis(3-dodecyl-2-thienyl)-2,2'-bithiophene] (PQT-12) thin films for the purpose of enhancing the field-effect mobility in thin-film transistors. The host polymer was used to stabilize the nanotubes in suspension through π-orbital overlap caused by simple application of ultrasonication. The stable nanotube suspension was cast into two different device architectures, both of which exhibited excellent on/off ratios ranging from 105 to 106 and dramatically improved mobilities compared with pristine PQT-12 semiconductor. A single-layer film with nanotubes embedded throughout was easy to fabricate and had mobility up to 0.34 cm2/Vs, an enhancement of over 3× compared with PQT-12. Placing the nanotubes closer to the dielectric surface in a dual-layer approach resulted in a mobility improvement of up to six times (0.58 cm2/Vs). The effects of the nanotube content on the polymer interaction within the suspension, film morphology, and electrical properties were investigated as well.

  4. The phenyl + phenyl reaction as pathway to benzynes: An experimental and theoretical study

    NASA Astrophysics Data System (ADS)

    Dürrstein, Steffen H.; Olzmann, Matthias; Aguilera-Iparraguirre, Jorge; Barthel, Robert; Klopper, Wim

    2011-09-01

    Theoretical and experimental results shed light on the phenyl + phenyl reaction. Benzyne formation in the phenyl + phenyl reaction is important. Rate for benzyne formation is one order of magnitude below recombination rate. Coupled-cluster barrier heights differ significantly from CASPT2 results. Satisfactory agreement between B3LYP and coupled-cluster results.

  5. 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.

  6. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). Link to an amendment published at 79 FR 34637, June 18, 2014. (a) Chemical... as substituted phenyl azo substituted phenyl esters (PMNs P-95-655, P-95-782 and P-95-871)...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

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

    Code of Federal Regulations, 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...

  11. Ultraviolet photodissociation dynamics of the phenyl radical

    NASA Astrophysics Data System (ADS)

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

    2012-01-01

    Ultraviolet (UV) photodissociation dynamics of jet-cooled phenyl radicals (C6H5 and C6D5) 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 + C6H4 product translational energy distributions, P(ET)'s, peak near ˜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 107-108 s-1 with internal energy from 30 to 46 kcal/mol above the threshold of the lowest energy channel H + o-C6H4 (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-C6H4, as the main channel from unimolecular decomposition of the ground electronic state phenyl radical following internal conversion of the electronically excited state.

  12. 40 CFR 721.6490 - Alkyl phenyl polyetheramines.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl phenyl polyetheramines. 721.6490... Substances § 721.6490 Alkyl phenyl polyetheramines. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as alkyl phenyl...

  13. 40 CFR 721.6490 - Alkyl phenyl polyetheramines.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl phenyl polyetheramines. 721.6490... Substances § 721.6490 Alkyl phenyl polyetheramines. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as alkyl phenyl...

  14. 40 CFR 721.6490 - Alkyl phenyl polyetheramines.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkyl phenyl polyetheramines. 721.6490... Substances § 721.6490 Alkyl phenyl polyetheramines. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as alkyl phenyl...

  15. 40 CFR 721.6490 - Alkyl phenyl polyetheramines.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl phenyl polyetheramines. 721.6490... Substances § 721.6490 Alkyl phenyl polyetheramines. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as alkyl phenyl...

  16. 40 CFR 721.6490 - Alkyl phenyl polyetheramines.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl phenyl polyetheramines. 721.6490... Substances § 721.6490 Alkyl phenyl polyetheramines. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as alkyl phenyl...

  17. 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...

  18. 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...

  19. Ultraviolet photodissociation dynamics of the phenyl radical

    SciTech Connect

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

    2012-01-28

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

  20. Resonance Raman enhancement of phenyl ring vibrational modes in phenyl iron complex of myoglobin.

    PubMed

    Liu, H H; Lin, S H; Yu, N T

    1990-04-01

    Resonance Raman spectra are reported for the organometallic phenyl-FeIII complexes of horse heart myoglobin. We observed the resonance enhancement of the ring vibrational modes of the bound phenyl group. They were identified at 642, 996, 1,009, and 1,048 cm-1, which shift to 619, 961, 972, and 1,030 cm-1, respectively, upon phenyl 13C substitution. The lines at 642 and 996 cm-1 are assigned, respectively, as in-plane phenyl ring deformation mode (derived from benzene vibration No. 6a at 606 cm-1) and out-of-plane CH deformation (derived from benzene vibration No. 5 at 995 cm-1). The frequencies of the ring "breathing" modes at 1,009 and 1,048 cm-1 are higher than the corresponding ones in phenylalanine (at 1,004 and 1,033 cm-1) and benzene (at 992 and 1,010 cm-1), indicating that the ring C--C bonds are strengthened (or shortened) when coordinated to the heme iron. The excitation profiles of these phenyl ring modes and a porphyrin ring vibrational mode at 674 cm-1 exhibit peaks near its Soret absorption maximum at 431 nm. This appears to indicate that these phenyl ring modes may be enhanced via resonance with the Soret pi-pi transition. The FeIII--C bond stretching vibration has not been detected with excitation wavelengths in the 406.7-457.9-nm region.

  1. 4-Bromo-N-phenyl­benzamidoxime

    PubMed Central

    Cibian, Mihaela; Ferreira, Janaina G.; Hanan, Garry S.

    2009-01-01

    The title compound, C13H11BrN2O, a hydroxy­amidine derivative (an amidoxime), was obtained by addition of the corresponding imidoyl chloride to hydroxy­lamine. The benzene and phenyl rings are twisted from the mean plane of the hydroxy­amidine group by 34.4 (1) and 59.2 (1)°, respectively. In the crystal structure, inter­molecular O—H⋯N hydrogen bonds link pairs of mol­ecules, forming centrosymmetric dimers. PMID:21578411

  2. 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

  3. 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...

  4. 40 CFR 721.536 - Halogenated phenyl alkane.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Halogenated phenyl alkane. 721.536 Section 721.536 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.536 Halogenated phenyl alkane....

  5. 40 CFR 721.536 - Halogenated phenyl alkane.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 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)...

  6. 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)...

  7. First cascade Mitsunobu reactions for the synthesis of 2-benzoxazole-N-phenyl and 2-benzimidazole-N-phenyl derivatives.

    PubMed

    Yan, Yu; Zhong, Qifei; Zhao, Nan; Liu, Gang

    2012-02-01

    An efficient method has been developed via cascade Mitsunobu reactions to synthesize 2-benzoxazole-N-phenyl and 2-benzimidazole-N-phenyl derivatives, which are common structural motifs in medicinal chemistry. This method also provides a new application of the Mitsunobu reaction.

  8. The fluorescence behaviour of methyl and phenyl salicylate

    NASA Astrophysics Data System (ADS)

    Ford, D.; Thistlethwaite, P. J.; Woolfe, G. J.

    1980-01-01

    Fluorcsccnce lifetimes tor the 450 nm emission of methyl and phenyl salicylate in various solvents have been measured. Qucnching studics on the 340 nm fluorescence of these molecules point to the existence of three distinct ground state conformers.

  9. 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.

  10. 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.

  11. Reaction of dichlorocarbene with 4-phenyl-1,3-dioxane

    SciTech Connect

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

    1988-02-20

    The authors have established for the first time that the reaction of 4-phenyl-1,3-dioxane with the dichlorocarbene generated from chloroform by the action of a 50% aqueous solution of sodium hydroxide in the presence of triethylbenzylammonium chloride as phase-transfer catalysis leads to the formation of 4-phenyl-4-dichloromethyl-1,3-dioxane with a yield of 70% on the transformed reagent with 35% conversion with respect to the substrate. The product was isolated by column liquid chromatography. It was identified by means of the PMR and /sup 13/C NMR spectra and by the data from elemental analysis.

  12. Fragrance material review on 3-phenyl-1-propanol.

    PubMed

    Bhatia, S P; Wellington, G A; Cocchiara, J; Lalko, J; Letizia, C S; Api, A M

    2011-12-01

    A toxicologic and dermatologic review of 3-phenyl-1-propanol when used as a fragrance ingredient is presented. 3-Phenyl-1-propanol is a member of the fragrance structural group cinnamyl phenylpropyl compounds. The common characteristic structural element of cinnamyl phenylpropyl materials is an aryl substituted primary alcohol/aldehyde/ester. They are simple aromatic compounds with saturated propyl or unsaturated propenyl side chains containing a primary oxygenated functional group which has little toxic potential. 3-Phenyl-1-propyl derivatives participate in the same beta-oxidation pathways as do their parent cinnamic acid derivatives. 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 3-phenyl-1-propanol was evaluated then summarized and includes physical properties, acute toxicity, skin irritation, skin sensitization, in vitro skin absorption and mutagenicity. A safety assessment of all cinnamyl phenylpropyl compounds will be published simultaneously with this document; please refer to Belsito et al. (2011) for an overall assessment of the safe use of this material and all cinnamyl phenylpropyl materials in fragrances (Belsito, D., Bickers, D., Bruze, M., Dagli, M.L., Fryer, A., Greim, H., Miyachi, Y., Saurat, J.H., Sipes, I.G., 2011. A toxicologic and dermatologic assessment of cinnamyl phenylpropyl compounds when used as fragrance ingredients.).

  13. 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

  14. 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...

  15. 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...

  16. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  17. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  18. 40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  19. 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...

  20. 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...

  1. 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...

  2. 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... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N- phenyl]-N... substance identified generically as 1,4-benzenediamine, N′-(alkyl)-N- phenyl]-N-phenyl- (PMN P-06-731)...

  3. 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... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N- phenyl]-N... substance identified generically as 1,4-benzenediamine, N′-(alkyl)-N- phenyl]-N-phenyl- (PMN P-06-731)...

  4. 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... Significant New Uses for Specific Chemical Substances § 721.10349 1,4-Benzenediamine, N′-(alkyl)-N- phenyl]-N... substance identified generically as 1,4-benzenediamine, N′-(alkyl)-N- phenyl]-N-phenyl- (PMN P-06-731)...

  5. 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.

  6. 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.

  7. 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.

  8. 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.

  9. Fragrance material review on 4-phenyl-3-buten-2-ol.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of 4-phenyl-3-buten-2-ol when used as a fragrance ingredient is presented. 4-Phenyl-3-buten-2-ol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a secondary 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 4-phenyl-3-buten-2-ol were evaluated then summarized and includes physical properties, 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.

  10. Fragrance material review on ethyl phenyl carbinyl acetate.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of ethyl phenyl carbinyl acetate when used as a fragrance ingredient is presented. Ethyl phenyl carbinyl acetate is a member of the fragrance structural group Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). The AAASAE fragrance ingredients are prepared by reacting an aryl alkyl alcohol with a simple carboxylic acid (a chain of 1-4 carbons) to generate formate, acetate, propionate, butyrate, isobutyrate and carbonate esters. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for ethyl phenyl carbinyl acetate were evaluated, then summarized, and includes: physical properties; acute toxicity; skin irritation; and skin sensitization data. A safety assessment of the entire AAASAE will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all AAASAE in fragrances. PMID:22433983

  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. 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

  13. 1-Methyl-3-phenyl­sulfonyl-2-piperidone

    PubMed Central

    Zukerman-Schpector, Julio; Olivato, Paulo R.; Cerqueira Jr, Carlos R.; Vinhato, Elisângela; Tiekink, Edward R. T.

    2008-01-01

    The piperidone ring in the title compound, C12H15NO3S, has a slightly distorted half-chair conformation with the methyl, carbonyl and phenyl­sulfonyl ring substituents occupying equatorial, equatorial and axial positions, respectively. Mol­ecules are connected into centrosymmetric dimers via C—H⋯O inter­actions and these associate into layers via C—H⋯O—S contacts. Further C—H⋯O inter­actions involving both the carbonyl and sulfonyl O atoms consolidate the crystal packing by providing connections between the layers. PMID:21202324

  14. 5-Iodo-3-phenyl-2,1-benzoxazole.

    PubMed

    Teslenko, Yuriy; Matiychuk, Vasyl S; Kinzhybalo, Vasyl; Lis, Tadeusz; Obushak, Mykola D

    2013-04-01

    The title compound, C13H8INO, was prepared by a condensation reaction of 4-nitro-benzene with phenyl-acetonitrile in NaOH-ethanol solution. There are two independent mol-ecules in the asymmetric unit, in which the dihedral angles between the benzene ring and the benzoisoxazole unit are 4.2 (3) and 4.1 (3)°. The crystal packing is governed by C-H⋯N, C-I⋯π and C-I⋯O inter-actions.

  15. Phenyl acetate derivatives, fluorine-substituted on the phenyl group, as rapid recovery hypnotic agents with reflex depression.

    PubMed

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

    2015-01-01

    We report the synthesis of novel, potentially hypnotic fluorine-substituted phenyl acetate derivatives. We describe the structure-activity relationship that led us to the promising derivative: ethyl 2-(4-(2-(diethylamino)-2-oxoethoxy)-5-ethoxy-2-fluorophenyl) acetate (55). The unique pharmacological features of compound 55 are its relatively high affinity for the GABAA receptor, together with a unique affinity for the NMDA receptor, different to propanidid and AZD3043. In animal models, compound 55 showed stronger hypnotic potency and longer duration of LORR than propanidid and AZD3043, but also maintained a rapid recovery time to walking and behavioral recovery. In particular, compound 55 displayed reflex depression during infusion.

  16. Photodissociation dynamics of the phenyl radical via photofragment translational spectroscopy

    NASA Astrophysics Data System (ADS)

    Negru, Bogdan; Goncher, Scott J.; Brunsvold, Amy L.; Just, Gabriel M. P.; Park, Dayoung; Neumark, Daniel M.

    2010-08-01

    Photofragment translational spectroscopy was used to study the photodissociation dynamics of the phenyl radical C6H5 at 248 and 193 nm. At 248 nm, the only dissociation products observed were from H atom loss, attributed primarily to H+o-C6H4 (ortho-benzyne). The observed translational energy distribution was consistent with statistical decay on the ground state surface. At 193 nm, dissociation to H+C6H4 and C4H3+C2H2 was observed. The C6H4 fragment can be either o-C6H4 or l-C6H4 resulting from decyclization of the phenyl ring. The C4H3+C2H2 products dominate over the two H loss channels. Attempts to reproduce the observed branching ratio by assuming ground state dynamics were unsuccessful. However, these calculations assumed that the C4H3 fragment was n-C4H3, and better agreement would be expected if the lower energy i-C4H3+C2H2 channel were included.

  17. Photodissociation dynamics of the phenyl radical via photofragment translational spectroscopy

    SciTech Connect

    Negru, Bogdan; Goncher, Scott J.; Brunsvold, Amy L.; Just, Gabriel M. P.; Park, Dayoung; Neumark, Daniel M.

    2010-08-21

    Photofragment translational spectroscopy was used to study the photodissociation dynamics of the phenyl radical C{sub 6}H{sub 5} at 248 and 193 nm. At 248 nm, the only dissociation products observed were from H atom loss, attributed primarily to H+o-C{sub 6}H{sub 4} (ortho-benzyne). The observed translational energy distribution was consistent with statistical decay on the ground state surface. At 193 nm, dissociation to H+C{sub 6}H{sub 4} and C{sub 4}H{sub 3}+C{sub 2}H{sub 2} was observed. The C{sub 6}H{sub 4} fragment can be either o-C{sub 6}H{sub 4} or l-C{sub 6}H{sub 4} resulting from decyclization of the phenyl ring. The C{sub 4}H{sub 3}+C{sub 2}H{sub 2} products dominate over the two H loss channels. Attempts to reproduce the observed branching ratio by assuming ground state dynamics were unsuccessful. However, these calculations assumed that the C{sub 4}H{sub 3} fragment was n-C{sub 4}H{sub 3}, and better agreement would be expected if the lower energy i-C{sub 4}H{sub 3}+C{sub 2}H{sub 2} channel were included.

  18. Photodissociation Dynamics of the Phenyl Radical via Photofragment Translational Spectroscopy

    NASA Astrophysics Data System (ADS)

    Negru, Bogdan; Goncher, Scott J.; Brunsvold, Amy L.; Neumark, Daniel M.

    2010-06-01

    Photofragment translational spectroscopy was used to study the photodissociation dynamics of the phenyl radical at 193 and 248 nm. Time of flight data collected for the C_6H_4, C_4H_3, and C_2H_2 photofragments show the presence of two decomposition channels. The only C_6H_5 decomposition channel observed at 248 nm corresponds to C-H bond fission from the cyclic radical producing ortho-benzyne. The translational energy distribution peaks at 0 kcal/mol and is consistent with no exit barrier for the H loss process. At 193 nm photodissociation, however, H loss was observed to be the minor channel, while the major decomposition pathway corresponds with decyclization of the C_6H_5 radical and subsequent fragmentation to n-C_4H_3 and C_2H_2. These two momentum matched photofragments have a translational energy distribution that peaks around 9 kcal/mol, indicative of a process that proceeds through a tighter transition state. Previous theoretical work on the unimolecular decomposition of the phenyl radical predicts a second H loss process that occurs after C_6H_5 decyclization resulting in the linear C_6H_4 photofragment. This channel cannot be unambiguously discerned from the C_6H_4^+ time of flight data, but is believed to take place since decyclization is observed. L. K. Madden, L. V. Moskaleva, S. Kristyan, and M. C. Lin J. Phys. Chem. A 1997, 101, 6790.

  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. Reactivities of Substituted α-Phenyl-N-tert-butyl Nitrones

    PubMed Central

    2015-01-01

    In this work, a series of α-phenyl-N-tert-butyl nitrones bearing one, two, or three substituents on the tert-butyl group was synthesized. Cyclic voltammetry (CV) was used to investigate their electrochemical properties and showed a more pronounced substituent effect for oxidation than for reduction. Rate constants of superoxide radical (O2•–) reactions with nitrones were determined using a UV–vis stopped-flow method, and phenyl radical (Ph•) trapping rate constants were measured by EPR spectroscopy. The effect of N-tert-butyl substitution on the charge density and electron density localization of the nitronyl carbon as well as on the free energies of nitrone reactivity with O2•– and HO2• were computationally rationalized at the PCM/B3LYP/6-31+G**//B3LYP/6-31G* level of theory. Theoretical and experimental data showed that the rates of the reaction correlate with the nitronyl carbon charge density, suggesting a nucleophilic nature of O2•– and Ph• addition to the nitronyl carbon atom. Finally, the substituent effect was investigated in cell cultures exposed to hydrogen peroxide and a correlation between the cell viability and the oxidation potential of the nitrones was observed. Through a combination of computational methodologies and experimental methods, new insights into the reactivity of free radicals with nitrone derivatives have been proposed. PMID:24968285

  1. Different photochemical events of a genetically encoded phenyl azide define and modulate GFP fluorescence.

    PubMed

    Reddington, Samuel C; Rizkallah, Pierre J; Watson, Peter D; Pearson, Rachel; Tippmann, Eric M; Jones, D Dafydd

    2013-06-01

    Expanding the genetic code opens new avenues to modulate protein function in real time. By genetically incorporating photoreactive phenyl azide, the fluorescent properties of green fluorescent protein (GFP) can be modulated by light. Depending on the residue in GFP programmed to incorporate the phenyl azide, different effects on function and photochemical pathways are observed.

  2. 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...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

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

    Code of Federal Regulations, 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...

  5. 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...

  6. 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.

  7. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt (generic). 721.2577 Section 721.2577... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2577 Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

  8. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine salt (generic). 721.2577 Section 721.2577... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2577 Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

  9. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

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

  10. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  12. 40 CFR 721.9545 - 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...

  13. 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...

  14. 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...

  15. 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...

  16. 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...

  17. 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...

  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, 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...

  20. 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...

  1. Phenyl galactopyranosides - 13C CPMAS NMR and conformational analysis using genetic algorithm

    NASA Astrophysics Data System (ADS)

    Wałejko, Piotr; Paradowska, Katarzyna; Bukowicki, Jarosław; Witkowski, Stanisław; Wawer, Iwona

    2015-08-01

    Structural analyses of four compounds (phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (1), phenyl β-D-galactopyranoside (2), phenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (3) and phenyl α-D-galactopyranoside (4)) have been performed using solid-state 13C MAS NMR spectroscopy and theoretical methods. Conformational analysis involved grid search and genetic algorithm (GAAGS). Low-energy conformers found by GAAGS were further optimized by DFT and chemical shifts were calculated using GIAO/DFT approach. 13C CPMAS NMR chemical shift of carbon C2 is indicative of the glycoside torsional angle. Separated or merged resonances of C2 and C6 suggest free rotation of phenyl ring in the solid phase.

  2. Radical arylation of phenols, phenyl ethers, and furans.

    PubMed

    Wetzel, Alexander; Pratsch, Gerald; Kolb, Roman; Heinrich, Markus R

    2010-02-22

    Radical arylations of para-substituted phenols and phenyl ethers proceeded with good regioselectivity at the ortho position with respect to the hydroxy or alkoxy group. The reactions were conducted with arenediazonium salts as the aryl radical source, titanium(III) chloride as the reductant, and diluted hydrochloric acid as the solvent. Substituted biaryls were obtained from hydroxy- and alkoxy-substituted benzylamines, phenethylamines, and aromatic amino acids. The methodology described offers a fast, efficient, and cost-effective new access to diversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxy groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a beta-secretase inhibitor and the synthesis of a calcium-channel modulator. PMID:20066707

  3. 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

  4. 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... phenyl) azo, sodium salt (PMN P-95-274) is subject to reporting under this section for the......

  5. 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...

  6. 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...

  7. 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...

  8. 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...

  9. 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...

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

    ERIC Educational Resources Information Center

    Hocking, M. B.

    1980-01-01

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

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

    DOEpatents

    Farha, Omar K; Hupp, Joseph T

    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.

  12. 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.

  13. (E)-2-Cyano-3-(substituted phenyl)acrylamide analogs as potent inhibitors of tyrosinase: A linear β-phenyl-α,β-unsaturated carbonyl scaffold.

    PubMed

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

    2015-12-15

    In this study, we synthesized (E)-2-cyano-3-(substituted phenyl)acrylamide (CPA) derivatives which possess a linear β-phenyl-α,β-unsaturated carbonyl scaffold and examined their inhibitory activities against tyrosinase. CPA analogs exerted inhibitory activity against mushroom tyrosinase. Results from the docking simulation indicated that CPA2 could bind directly to the active site of mushroom tyrosinase and the binding affinity of CPA2 for tyrosinase might be higher than that of kojic acid, a well-known potent tyrosinase inhibitor. In B16F10 cells, CPA2 significantly suppressed tyrosinase activity and melanogenesis in a dose-dependent manner. At the concentration of 25μM, CPA2 exhibited tyrosinase inhibitory activity comparable to that of kojic acid with no cytotoxic effect. Results from the present study suggest that CPA2 bearing a linear β-phenyl-α,β-unsaturated carbonyl scaffold may be the potential candidate for treatment of diseases associated with hyperpigmentation and that a linear β-phenyl-α,β-unsaturated carbonyl scaffold might be closely related to potent tyrosinase inhibition.

  14. 3-(4-Fluoro­phenyl­sulfin­yl)-2,4,6-trimethyl-1-benzofuran

    PubMed Central

    Choi, Hong Dae; Seo, Pil Ja; Son, Byeng Wha; Lee, Uk

    2010-01-01

    In the title compound, C17H15FO2S, the O atom and the 4-fluoro­phenyl group of the 4-fluoro­phenyl­sulfinyl substituent lie on opposite sides of the plane of the benzofuran; the 4-fluoro­phenyl ring is almost perpendicular to this plane, making a dihedral angle of 88.99 (4)°. The crystal structure exhibits inter­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions between the methyl H atom and the 4-fluoro­phenyl ring. PMID:21580351

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

    PubMed

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

    2014-07-01

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

  16. 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.

  17. 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.

  18. 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.

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

    DOEpatents

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

  20. Facile access to highly fluorescent nanofibers and microcrystals via reprecipitation of 2-phenyl-benzoxazole derivatives.

    PubMed

    Ghodbane, Abdelhamid; D'Altério, Sébastien; Saffon, Nathalie; McClenaghan, Nathan D; Scarpantonio, Luca; Jolinat, Pascale; Fery-Forgues, Suzanne

    2012-01-10

    2-Phenyl-benzoxazole and five derivatives bearing an alkyl or alkoxy substituent on the phenyl ring were used to prepare aqueous suspensions of particles via a solvent-exchange method. In these conditions, the methyl and methoxy derivatives spontaneously gave nanofibers, while the other compounds led to microcrystals. This shows that minor chemical changes are enough to direct the formation of a given type of particle. From a spectroscopic viewpoint, all compounds strongly emit blue light in the solid state, with spectra much broader than those registered in n-heptane and ethanol solutions. The photoluminescence quantum yields reached 38% and were slightly affected in aqueous suspension by the polarity of the environment. The molecular arrangement, deduced from X-ray analysis for the methyl and methoxy derivatives, was used to explain the fluorescence properties in the solid state. This work shows that 2-phenyl-benzoxazole derivatives are interesting candidates for applications as fluorescent nanomaterials, including in aqueous and biological media.

  1. 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

  2. Reactivity of substituted charged phenyl radicals toward components of nucleic acids.

    PubMed

    Ramírez-Arizmendi, Luis E; Heidbrink, Jenny L; Guler, Leonard P; Kenttämaa, Hilkka I

    2003-02-26

    Reactions of differently substituted phenyl radicals with components of nucleic acids have been investigated in the gas phase. A positively charged group located meta with respect to the radical site was employed to allow manipulation of the radicals in a Fourier-transform ion cyclotron resonance mass spectrometer. All of these electrophilic radicals react with sugars via exclusive hydrogen atom abstraction, with adenine and uracil almost exclusively via addition (likely at the C8 and C5 carbons, respectively), and with the nucleoside thymidine by hydrogen atom abstraction and addition at C5 in the base moiety (followed by elimination of (*)CH(3)). These findings parallel the reactivity of the phenyl radical with components of nucleic acids in solution, except that the selectivity for addition is different. Like HO(*), the electrophilic charged phenyl radicals appear to favor addition to the C5-end of the C5-C6 double bond of thymine and thymidine, whereas the phenyl radical preferentially adds to C6. The charged phenyl radicals do not predominantly add to thymine, as the neutral phenyl radical and HO(*), but mainly react by hydrogen atom abstraction from the methyl group (some addition to C5 in the base followed by loss of (*)CH(3) also occurs). Adenine appears to be the preferred target among the nucleobases, while uracil is the least favored. A systematic increase in the electrophilicity of the radicals by modification of the radicals' structures was found to facilitate all reactions, but the addition even more than hydrogen atom abstraction. Therefore, the least reactive radicals are most selective toward hydrogen atom abstraction, while the most reactive radicals also efficiently add to the base. Traditional enthalpy arguments do not rationalize the rate variations. Instead, the rates reflect the radicals' electron affinities used as a measure for their ability to polarize the transition state of each reaction.

  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. 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

  5. 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

  6. 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

  7. Enhanced charge transfer by phenyl groups at a rubrene/C60 interface

    NASA Astrophysics Data System (ADS)

    Mou, Weiwei; Ohmura, Satoshi; Hattori, Shinnosuke; Nomura, Ken-ichi; Shimojo, Fuyuki; Nakano, Aiichiro

    2012-05-01

    Exciton dynamics at an interface between an electron donor, rubrene, and a C60 acceptor is studied by nonadiabatic quantum molecular dynamics simulation. Simulation results reveal an essential role of the phenyl groups in rubrene in increasing the charge-transfer rate by an order-of-magnitude. The atomistic mechanism of the enhanced charge transfer is found to be the amplification of aromatic breathing modes by the phenyl groups, which causes large fluctuations of electronic excitation energies. These findings provide insight into molecular structure design for efficient solar cells, while explaining recent experimental observations.

  8. Enhanced charge transfer by phenyl groups at a rubrene/C60 interface.

    PubMed

    Mou, Weiwei; Ohmura, Satoshi; Hattori, Shinnosuke; Nomura, Ken-ichi; Shimojo, Fuyuki; Nakano, Aiichiro

    2012-05-14

    Exciton dynamics at an interface between an electron donor, rubrene, and a C(60) acceptor is studied by nonadiabatic quantum molecular dynamics simulation. Simulation results reveal an essential role of the phenyl groups in rubrene in increasing the charge-transfer rate by an order-of-magnitude. The atomistic mechanism of the enhanced charge transfer is found to be the amplification of aromatic breathing modes by the phenyl groups, which causes large fluctuations of electronic excitation energies. These findings provide insight into molecular structure design for efficient solar cells, while explaining recent experimental observations. PMID:22583307

  9. Enhanced charge transfer by phenyl groups at a rubrene/C{sub 60} interface

    SciTech Connect

    Mou Weiwei; Hattori, Shinnosuke; Nomura, Ken-ichi; Nakano, Aiichiro; Ohmura, Satoshi; Shimojo, Fuyuki

    2012-05-14

    Exciton dynamics at an interface between an electron donor, rubrene, and a C{sub 60} acceptor is studied by nonadiabatic quantum molecular dynamics simulation. Simulation results reveal an essential role of the phenyl groups in rubrene in increasing the charge-transfer rate by an order-of-magnitude. The atomistic mechanism of the enhanced charge transfer is found to be the amplification of aromatic breathing modes by the phenyl groups, which causes large fluctuations of electronic excitation energies. These findings provide insight into molecular structure design for efficient solar cells, while explaining recent experimental observations.

  10. Five nitro-phenyl compounds from the South China Sea mangrove fungus.

    PubMed

    Shao, Chang-Lun; Guo, Zhi-Yong; Xia, Xue-Kui; Liu, Yan; Huang, Zhong-Jing; She, Zhi-Gang; Lin, Yong-Cheng; Zhou, Shi-Ning

    2007-01-01

    A novel nitro-phenyl glucoside (1) was isolated from mangrove endophytic fungus (fungus B60), collected from the Shenzhen mangrove Acanthus ilicifolius linn. Four related nitro-phenyl compounds (2-5) were also obtained, which were isolated for the first time as natural products. Their structures were established on the basis of NMR spectroscopic, mass spectrometric data and some chemical transformations. In the preliminary bioassay, compound 1 had a slight inhibitory effect on alpha-glucosidase with an IC(50) of 160.3 microM.

  11. Thermal and photochemical solvolysis of (E)- and (Z)-2-phenyl-1-propenyl(phenyl)iodonium tetrafluoroborate: benzenium and primary vinylic cation intermediates.

    PubMed

    Gronheid, R; Lodder, G; Ochiai, M; Sueda, T; Okuyama, T

    2001-09-12

    The thermal and photochemical solvolysis of the two stereoisomeric 2-phenyl-1-propenyl(phenyl)iodonium tetrafluoroborates has been investigated in alcoholic solvents of varying nucleophilicity. The product profiles and rates of product formation in the thermal reaction are all compatible with a mechanism involving cleavage of the vinylic C-I bond assisted by the group in the trans position (methyl or phenyl), always leading to rearranged products. Depending on the nucleophilicity of the solvent, the primarily formed cations may or may not further rearrange to more stable isomers. The less reactive Z compound also yields some unrearranged vinyl ether product in the more nucleophilic solvents via an in-plane S(N)2 mechanism. The mechanism of the photolysis involves direct, unassisted cleavage of the vinylic, and aromatic, C-I bond in an S(N)1 mechanism. This produces a primary vinyl cation, which is partially trapped prior to rearrangement in methanol. The unrearranged vinyl ethers are mainly formed with retention of configuration via a lambda3-iodonium/solvent complex in an S(N)i mechanism. Thermal and photochemical solvolyses of iodonium salts are complementary techniques for the generation of different cation intermediates from the same substrate.

  12. 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...

  13. 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...

  14. 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…

  15. 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... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5930 Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt...

  16. 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... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5930 Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt...

  17. 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... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5930 Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium salt...

  18. Synthesis and biological evaluation of 1-phenyl-1,2,3,4-dihydroisoquinoline compounds as tubulin polymerization inhibitors.

    PubMed

    Zheng, Can-Hui; Chen, Jun; Liu, Jia; Zhou, Xiao-Tian; Liu, Na; Shi, Duo; Huang, Jing-Jing; Lv, Jia-Guo; Zhu, Ju; Zhou, You-Jun

    2012-06-01

    A series of 1-phenyl-3,4-dihydroisoquinoline derivatives and several 1-phenyl-1,2,3,4-tetrahydroisoquinoline, 1-phenyl-isoquinoline analogues were synthesized, and their cytotoxicity and tubulin polymerization inhibitory activity were evaluated. The 1-phenyl-3,4-dihydroisoquinoline compounds were found to be potential tubulin polymerization inhibitors. Compound 5n, bearing a 3'-OH and 4'-OCH(3) substituted 1-phenyl B-ring, was shown to confer optimal bioactivity. The single-crystal structure of 5n was further determined by X-ray diffraction, and the binding mode of 5n to tubulin was obtained by molecular docking, which can explain the structure-activity relationships. The studies presented here provide a new structural type for the development of novel antitumor agents.

  19. Synthesis and dopamine D2-like receptor binding affinity of substituted 5-phenyl-pyrrole-3-carboxamides.

    PubMed

    Pinna, G A; Curzu, M M; Sechi, M; Chelucci, G; Maciocco, E

    1999-08-30

    A series of 5-p-substituted phenyl-pyrrole-3-carboxamide derivatives was designed as hybrid analogs of the dopamine D2-like 5-phenyl-pyrrole and heterocyclic carboxamide antipsychotics. The title compounds were synthesized and evaluated for dopamine D2-like receptor by means of [3H]YM-09151-2 receptor binding assay. The compound bearing a 1-ethyl-2-methyl-pyrrolidine moiety as the basic part of 5-phenyl-pyrrole-3-carboxamide derivative 1a together with its 2-chloro analog 1f were found to possess affinity in the low micromolar range. Substituted phenyl-pyrrolecarboxamides containing groups such as F, Cl, NO2, CH3, at the 4-position of the phenyl ring, gave ligands with lower D2-like affinity.

  20. Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate.

    PubMed

    Nambo, Masakazu; Ariki, Zachary T; Canseco-Gonzalez, Daniel; Beattie, D Dawson; Crudden, Cathleen M

    2016-05-20

    A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.

  1. Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate.

    PubMed

    Nambo, Masakazu; Ariki, Zachary T; Canseco-Gonzalez, Daniel; Beattie, D Dawson; Crudden, Cathleen M

    2016-05-20

    A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated. PMID:27124389

  2. 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)

  3. Inhibition effects of benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on the activity of mushroom tyrosinase.

    PubMed

    Liu, Xuan; Jia, Yu-long; Chen, Jing-wei; Liang, Ge; Guo, Hua-yun; Hu, Yong-hua; Shi, Yan; Zhou, Han-Tao; Chen, Qing-Xi

    2015-03-01

    Tyrosinase (EC 1.14.18.1) is the key enzyme of melanin synthesis and fruit-vegetable browning. The inhibition of benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on mushroom tyrosinase was first investigated. The results shown that these three compounds could effectively inhibit the enzyme activity sharply and the inhibitory effects were determined to be reversible. Their inhibitor concentrations leading to 50% activity lost values were determined to be 1.5, 2.8, and 1.1 mM for monophenolase and 2.0, 0.6, and 0.8 mM for diphenolase, respectively. For the monophenolase activity, all of these three compounds were mixed-type inhibitors, however, only 4-phenyl-2-butanol obviously lengthened the lag time. For the diphenolase activity, benzylideneacetone and benzylacetone were mixed-type inhibitors, while 4-phenyl-2-butanol was a noncompetitive type inhibitor. In conclusion, these compounds exhibited potent antityrosinase activities. This research would provide scientific evidence for the use of benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol as antityrosinase agents.

  4. Efficient synthesis of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate: a versatile precursor to o-benzyne.

    PubMed

    Bronner, Sarah M; Garg, Neil K

    2009-11-20

    An efficient procedure for the gram-scale preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a versatile precursor to o-benzyne, is presented. The three-step sequence utilizes phenol as the starting material, requires only one chromatographic purification, and ultimately delivers the desired silyltriflate in 66% overall yield.

  5. 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.

  6. 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.

  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. 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...

  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, 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...

  11. 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.

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

    NASA Astrophysics Data System (ADS)

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

    2012-04-01

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

  13. Spectroscopic identification of surface phenyl thiolate and benzyne on Mo(110)

    SciTech Connect

    Roberts, J.T.; Friend, C.M.

    1988-06-01

    Chemisorbed phenyl thiolate (C/sub 6/H/sub 5/S) and surface benzyne (C/sub 6/H/sub 4/) formed during the temperature programmed reaction of benzenethiol on Mo(110) have been characterized using x-ray photoelectron and high resolution electron energy loss spectroscopies. Electron energy loss spectroscopy demonstrates that at all exposures the S--H bond of benzenethiol breaks upon adsorption at 120 K, while x-ray photoelectron spectroscopy confirms that the C--S bond is intact. The intermediate formed upon adsorption is assigned as a chemisorbed phenyl thiolate. At high exposures, approximately 40% of the phenyl thiolate reacts by way of hydrogenolysis at 350 K to form gaseous benzene and atomic sulfur, while 60% undergoes dehydrogenation at approx. =370 K to form surface benzyne and atomic sulfur. Electron energy loss spectroscopy reveals that surface benzyne is aromatic in nature, and x-ray photoelectron spectroscopy confirms that the C--S bond is no longer intact. Surface benzyne is unusually stable on the sulfided Mo(110), decomposing at 680 K to gaseous dihydrogen and atomic carbon, with an activation energy of 42 kcal/mol in the limit of high coverage. At low coverages, the phenyl thiolate decomposes on Mo(110) to surface carbon, surface sulfur, and gaseous dihydrogen, with decomposition complete below 600 K. At low coverages, no formation of gaseous benzene or surface benzyne occurs. The coverage dependence of the reaction kinetics of the phenyl thiolate on Mo(110) are attributed, in part, to a change in the structure of the adsorbed thiolate at high coverages.

  14. GluK1 antagonists from 6-(tetrazolyl)phenyl decahydroisoquinoline derivatives: in vitro profile and in vivo analgesic efficacy.

    PubMed

    Martinez-Perez, Jose A; Iyengar, Smriti; Shannon, Harlan E; Bleakman, David; Alt, Andrew; Clawson, David K; Arnold, Brian M; Bell, Michael G; Bleisch, Thomas J; Castaño, Ana M; Del Prado, Miriam; Dominguez, Esteban; Escribano, Ana M; Filla, Sandra A; Ho, Ken H; Hudziak, Kevin J; Jones, Carrie K; Mateo, Ana; Mathes, Brian M; Mattiuz, Edward L; Ogden, Ann Marie L; Simmons, Rosa Maria A; Stack, Douglas R; Stratford, Robert E; Winter, Mark A; Wu, Zhipei; Ornstein, Paul L

    2013-12-01

    We have explored the decahydroisoquinoline scaffold, bearing a phenyl tetrazole, as GluK1 antagonists with potential as oral analgesics. We have established the optimal linker atom between decahydroisoquinoline and phenyl rings and demonstrated an improvement of both the affinity for the GluK1 receptor and the selectivity against the related GluA2 receptor with proper phenyl substitution. In this Letter, we also disclose in vivo data that led to the discovery of LY545694·HCl, a compound with oral efficacy in two persistent pain models.

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

    PubMed Central

    Kapuściński, Jan; Skoczylas, Bogna

    1978-01-01

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

  16. Discovery of 5-benzyl-3-phenyl-4,5-dihydroisoxazoles and 5-benzyl-3-phenyl-1,4,2-dioxazoles as potent firefly luciferase inhibitors.

    PubMed

    Poutiainen, Pekka K; Palvimo, Jorma J; Hinkkanen, Ari E; Valkonen, Arto; Väisänen, Topi K; Laatikainen, Reino; Pulkkinen, Juha T

    2013-02-14

    Luciferase reporter assays are commonly used in high-throughput screening methods. Here, we report new firefly luciferase (FLuc) inhibitors based on 5-benzyl-3-phenyl-4,5-dihydroisoxazoles and 5-benzyl-3-phenyl-1,4,2-dioxazoles, which showed up as "false positives" in a luciferase reporter gene-based assay for nuclear receptor antagonists. The inhibition was shown to be noncompetitive for both natural enzyme substrates (d-luciferin and ATP) and selective to FLuc and proven to arise from a direct interaction between the enzyme and the inhibitor. Of the 63 evaluated compounds, 28 showed significantly better inhibition potency than the well-known inhibitor resveratrol (IC(50) = 59 nM), with five compounds having distinctly subnanomolar IC(50) values. The most efficient compounds inhibited the luminescence at concentrations lower than (1)/(100) in comparison to resveratrol (lowest IC(50) = 0.26 nM) and can thus be considered to belong to the most potent FLuc inhibitors reported thus far. Overall, the novel inhibitors form a unique molecular library for structure-activity relationship (SAR) analyses.

  17. 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.

  18. 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.

  19. 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

  20. Cp-Ftmw Spectroscopy of a Claisen Rearrangement Precursor Allyl Phenyl Ether

    NASA Astrophysics Data System (ADS)

    Grubbs, G. S., II; 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 for the first time and will be discussed. 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 APE conformers are presented and compared to similar molecules for discussion.

  1. 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.

  2. The effect of phenyl groups on the transport properties of tetracene molecule

    NASA Astrophysics Data System (ADS)

    Alizadeh, S.; Shahtahmassebi, N.; Pilevarshahri, R.; Vahedi Fakhrabad, D.

    2016-10-01

    Electronic transport properties of pure tetracene and rubrene molecules were studied using density functional theory within the non-equilibrium Green's function method. Transmission coefficient and I-V curve were calculated for both molecules. The comparison between transmission coefficients in tetracene and rubrene molecules shows that there are some extra peaks in rubrene that belong to phenyl rings which are attached to tetracene. Besides, we found that up to 2.2 V the current is almost the same in both rubrene and tetracene and above this value, the current in rubrene is increased in comparison to tetracene which is the result of attachment of additional phenyl groups in rubrene molecule. Finally, we detected that these two molecules exhibit negative differential resistance behavior in the range between 1.2 V and 2 V.

  3. 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.

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

    PubMed Central

    Charette, Bronte J.; Ritch, Jamie S.

    2015-01-01

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

  5. 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.

  6. Luminescent properties and photostability of thin films of N,N'-phenyl-substituted biphenyls

    NASA Astrophysics Data System (ADS)

    Chaplanova, Zh. D.; Mikhailovskii, Yu. K.; Agabekov, V. E.; Galinovskii, N. A.; Gracheva, E. A.

    2012-11-01

    We have studied the luminescent properties and morphology of thin films, formed by deposition from solutions (wet) and thermal vacuum deposition (TVD), of 4,4'- bis[(E)-2-[4-(diphenylamino)phenyl]ethenyl]-1,1'-biphenyl (PAB-1) and its 2-oxyhexyl derivative (PAB-2). We have established that the presence of an oxyhexyl side substituent in the structure of N,N'-phenyl-substituted biphenyl promotes quenching of the photoluminescence of the TVD film based on it when stored in air. We show that introducing PAB-2 into a polymer matrix (polymethylmethacrylate, polystyrene, polycyclohexadiene) significantly improves the stability of such composite films when exposed to UV light and to oxygen in the air. We use electron diffraction and atomic force microscopy to establish that these films have an amorphous structure that remains resistant to degradation during photooxidative aging.

  7. Phenyl-tetrazolyl acetophenones: discovery of positive allosteric potentiatiors for the metabotropic glutamate 2 receptor.

    PubMed

    Pinkerton, Anthony B; Vernier, Jean-Michel; Schaffhauser, Hervé; Rowe, Blake A; Campbell, Una C; Rodriguez, Dana E; Lorrain, Daniel S; Baccei, Christopher S; Daggett, Lorrie P; Bristow, Linda J

    2004-08-26

    Herein we disclose the discovery of a new class of positive allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2), phenyl-tetrazolyl acetophenones, e.g. 1-(2-hydroxy-3-propyl-4-[4-[4-(2H-tetrazol-5-yl)phenoxy]butoxy]phenyl) ethanone (4). These potentiators were shown to have no effect in the absence of glutamate as well as no effect at mGlu3 or the other mGlu receptors. The compounds were also evaluated in rodent models with potential relevance for schizophrenia, and 4 was shown to have activity in the inhibition of ketamine-induced norepinephrine release and ketamine-induced hyperactivity. This represents the first example of the efficacy of mGlu2 receptor potentiators in these models. PMID:15317469

  8. 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.

  9. Gas-phase reactions of charged phenyl radicals with neutral biomolecules evaporated by laser-induced acoustic desorption.

    PubMed

    Petzold, Christopher J; Ramírez-Arizmendi, Luis E; Heidbrink, Jenny L; Pérez, James; Kenttämaa, Hilkka I

    2002-02-01

    A generally applicable method for the study of phenyl radicals' reactions with neutral biomolecules in the gas phase is demonstrated. Neutral biomolecules were evaporated into a Fourier-transform ion cyclotron resonance mass spectrometer (FT-ICR) by means of laser-induced acoustic desorption (LIAD) and subsequently reacted with trapped charged phenyl radicals. The structural integrity of the evaporated alanylalanine molecules was verified by reaction with dichlorophosphenium ions. Examination of the reactions of charged phenyl radicals with alanylalanine and thymidine evaporated via LIAD revealed hydrogen atom abstraction for both alanylalanine and thymidine as well as an addition/elimination product for the reaction with thymidine. These reactions are consistent with the results obtained by others in solution. Further, a previously unstudied reaction of the nucleotide of thymine (T1) with charged phenyl radical was found to yield analogous products as the reaction with thymidine.

  10. 4-Hy-droxy-1-methyl-3-phenyl-quinolin-2(1H)-one.

    PubMed

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

    2013-02-01

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

  11. [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

  12. Copper-mediated aerobic (phenylsulfonyl)difluoromethylation of arylboronic acids with difluoromethyl phenyl sulfone.

    PubMed

    Li, Xinjin; Zhao, Jingwei; Hu, Mingyou; Chen, Dingben; Ni, Chuanfa; Wang, Limin; Hu, Jinbo

    2016-03-01

    A new method for the generation of the "PhSO2CF2Cu" species from readily available difluoromethyl phenyl sulfone (PhSO2CF2H) has been developed. The "PhSO2CF2Cu" reagent can be applied in (phenylsulfonyl)difluoromethylation of arylboronic acids, which affords a convenient approach to introducing the PhSO2CF2 group into aromatics. PMID:26854122

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

    NASA Astrophysics Data System (ADS)

    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.

  14. 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.

  15. 40 CFR 180.362 - Hexakis (2-methyl-2-phenyl-propyl)distannoxane; tolerances for residues.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... FOOD Specific Tolerances § 180.362 Hexakis (2-methyl-2-phenyl-propyl)distannoxane; tolerances for...: Commodity Parts per million Cattle, fat 0.5 Cattle, meat 0.5 Cattle, meat byproducts 0.5 Egg 0.1 Goat, fat 0.5 Goat, meat 0.5 Goat, meat byproducts 0.5 Hog, fat 0.5 Hog, meat 0.5 Hog, meat byproducts 0.5...

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

    PubMed

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

    2015-07-01

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

  17. 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

  18. 3-Phenyl­tetra­hydro­furan-2,5-dione

    PubMed Central

    Quan, Li; Yin, Handong

    2009-01-01

    In the title compound, C10H8O3, the dihedral angle between the approximately planar tetra­hydro­furan-2,5-dione ring [maximum deviation 0.014 (3) Å] and the phenyl ring is 85.68 (8)°. Weak C—H⋯O=C inter­molecular hydrogen-bonding contacts are observed in the structure. PMID:21581623

  19. Synthesis and biological activity of 3-[phenyl(1,3-thiazol-2-yl)-amino]propanoic acids and their derivatives.

    PubMed

    Mickevičius, Vytautas; Voskienė, Aušra; Jonuškienė, Ilona; Kolosej, Ramūnė; Šiugždaitė, Jūratė; Venskutonis, Petras Rimantas; Kazernavičiūtė, Rita; Brazienė, Zita; Jakienė, Elena

    2013-01-01

    New N,N-disubstituted β-amino acids and their derivatives with thiazole, aromatic, and heterocyclic substituents were synthesized from N-phenyl-N-thiocarbamoyl-β-alanine by the Hantzsch method; derivatives with hydrazone fragments were also obtained. Some of the synthesized compounds exhibited discrete antimicrobial activity, and 3-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)(phenyl)amino]propanoic acid was found to promote rapeseed growth and to increase seed yield and oil content.

  20. (E)-3-Methyl-2,6-di-phenyl-piperidin-4-one O-(3-methyl-benzo-yl)oxime.

    PubMed

    Kathiravan, V; Krishnan, K Gokula; Mohandas, T; Thanikachalam, V; Sakthivel, P

    2014-08-01

    In the title compound, C26H26N2O2, the piperidine ring exhibits a chair conformation. The phenyl rings are attached to the central heterocycle in an equatorial position. The dihedral angle between the planes of the phenyl rings is 57.58 (8)°. In the crystal, C-H⋯O inter-actions connect the mol-ecules into zigzag chains along [001].

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

    PubMed

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

    2015-04-15

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

  2. 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.

  3. 4-(Diphenyl­amino)­benzaldehyde 4-phenyl­thio­semicarbazone

    PubMed Central

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

    2012-01-01

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

  4. 5-Phenyl-4-pentenyl-hydroperoxide: a probe for hydroperoxide - metalloprotein interactions

    SciTech Connect

    Marnett, L.J.; Weller, P.E.

    1986-05-01

    5-Phenyl-4-pentenyl-hydroperoxide (PPHP) has been synthesized as a mechanistic probe for the reactions of hydroperoxides with metals and metalloproteins. Oxidation of PPHP by di-t-butyl-peroxyoxalate generated peroxyl radical cyclization products in 60% isolated yield. Reduction of PPHP by Fe/sup 2 +/-cysteine produced alkoxyl radical cyclization products in 40% yield along with 24% of 5-phenyl-4-pentenyl-alcohol (PPA). Reaction of PPHP with hematin produced 5-phenyl-4-pentenal (PPAL) in 96% yield. The structures of all products were assigned by high resolution NMR and mass spectroscopy and confirmed by independent synthesis. The fact that PPHP was converted by one-electron oxidation, one-electron reduction, and two-electron reduction to unique products prompted its use as a probe of metalloprotein- peroxide interactions. Horseradish peroxidase catalyzed the quantitative reduction of PPHP to PPa by phenol. Quantitative reduction in the presence of phenol was also catalyzed by catalase, lactoperoxidase, cytochrome c peroxidase, and prostaglandin H synthase. In contrast, microperoxidase, metmyoglobin, and methemoglobin catalyzed the conversion of PPHP to PPAL (80%) and PPA (20%) in either the presence or absence of phenol. The latter proteins exhibited low turnover numbers relative to the classical peroxidases. The results indicate that the PPHP can be used to differentiate a wide range of hemeproteins that reduce hydroperoxides by one or two electrons. Furthermore, the spectrum of products derived from it provides important information about the pathways of its metabolism.

  5. 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

  6. Fragrance material review on 1,2-ethanediol, 1-phenyl-, 1,2-diacetate.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of 1,2-ethanediol, 1-phenyl-, 1,2-diacetate when used as a fragrance ingredient is presented. 1,2-Ethanediol, 1-phenyl-, 1,2-diacetate 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 1,2-ethanediol, 1-phenyl-, 1,2-diacetate were evaluated, then summarized, and includes physical properties 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 fragrances.

  7. Fragrance material review on 1-phenyl-3-methyl-3-pentyl acetate.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of 1-phenyl-3-methyl-3-pentyl acetate when used as a fragrance ingredient is presented. 1-Phenyl-3-methyl-3-pentyl 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 1-phenyl-3-methyl-3-pentyl 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.

  8. Fragrance material review on 3-phenyl-3-buten-1-yl acetate.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of 3-phenyl-3-buten-1-yl acetate when used as a fragrance ingredient is presented. 3-Phenyl-3-buten-1-yl 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 3-phenyl-3-buten-1-yl acetate were evaluated, then summarized, and includes: physical properties, acute toxicity, skin irritation, mucous membrane (eye) 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.

  9. Fragrance material review on 2-methyl-4-phenyl-2-butyl acetate.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butyl acetate when used as a fragrance ingredient is presented. 2-Methyl-4-phenyl-2-butyl 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 2-methyl-4-phenyl-2-butyl acetate were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, skin sensitization, and elicitation 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.

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

    PubMed

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

    2015-02-23

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

  11. 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.

  12. 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.

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

    SciTech Connect

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

    2009-01-01

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

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

    PubMed Central

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

    2015-01-01

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

  15. Fragrance material review on 1-phenyl-3-methyl-3-pentyl acetate.

    PubMed

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

    2012-09-01

    A toxicologic and dermatologic review of 1-phenyl-3-methyl-3-pentyl acetate when used as a fragrance ingredient is presented. 1-Phenyl-3-methyl-3-pentyl 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 1-phenyl-3-methyl-3-pentyl 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:22406574

  16. 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).

  17. 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

  18. Anti-inflammatory effects of 4-phenyl-3-butenoic acid and 5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid methyl ester, potential inhibitors of neuropeptide bioactivation.

    PubMed

    Bauer, John D; Sunman, Jeffrey A; Foster, Michael S; Thompson, Jeremy R; Ogonowski, Alison A; Cutler, Stephen J; May, Sheldon W; Pollock, Stanley H

    2007-03-01

    Substance P (SP) and calcitonin gene-related peptide (CGRP) are well established mediators of inflammation. Therefore, inhibition of the biosynthesis of these neuropeptides is an attractive potential strategy for pharmacological intervention against a number of inflammatory diseases. The final step in the biosynthesis of SP and CGRP is the conversion of their glycine-extended precursors to the active amidated peptide, and this process is catalyzed by sequential action of the enzymes peptidylglycine alpha-monooxygenase (PAM) and peptidylamidoglycolate lyase. We have demonstrated previously that 4-phenyl-3-butenoic acid (PBA) is a PAM inhibitor, and we have also shown that in vivo inhibition of serum PAM by PBA correlates with this compound's ability to inhibit carrageenan-induced edema in the rat. Here we demonstrate the ability of PBA to inhibit all three phases of adjuvant-induced polyarthritis (AIP) in rats; this represents the first time that an amidation inhibitor has been shown to be active in a model of chronic inflammation. We recently introduced 5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid (AOPHA) as one of a new series of mechanism-based amidation inhibitors. We now report for the first time that AOPHA and its methyl ester (AOPHA-Me) are active inhibitors of serum PAM in vivo, and we show that AOPHA-Me correspondingly inhibits carrageenan-induced edema in rats in a dose-dependent manner. Neither PBA nor AOPHA-Me exhibits significant cyclooxygenase (COX) inhibition in vitro; thus, the anti-inflammatory activities of PBA and AOPHA-Me are apparently not a consequence of COX inhibition. We discuss possible pharmacological mechanisms that may account for the activities of these new anti-inflammatory compounds.

  19. 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)...

  20. Racemic tricarbonyl[(4a,5,6,7,8,8a-η)-2-phenyl-3,4-dihydro-2H-1-benzopyran]chromium(0)

    PubMed Central

    van Tonder, Johannes H.; Bezuidenhoudt, Barend C. B.; Janse van Rensburg, J. Marthinus

    2010-01-01

    The title compound, [Cr(C15H14O)(CO)3], displays a distorted envelope configuration of the dihydro­pyrane ring. The dihedral angle between the phenyl and phenyl­ene rings is 50.63 (4)°. The Cr0 atom is coordinated by three CO groups and the phenyl­ene ring of the flavan ligand in an η6 mode, with a common arene-to-metal distance PMID:21588503

  1. A 7-phenyl substituted triazolopyridazine has inverse agonist activity at the benzodiazepine receptor site.

    PubMed Central

    Biziere, K.; Bourguignon, J. J.; Chambon, J. P.; Heaulme, M.; Perio, A.; Tebib, S.; Wermuth, C. G.

    1987-01-01

    To investigate further the structural requirements for benzodiazepine (BZD) receptor ligands, we synthesized SR 95195, [7-phenyl-3-methyl-1,2,4-triazolo-(4,3-b) pyridazine], a positional isomer of the 6-phenyl-triazolo-pyridazines, which were the first non-BZD derivatives to exhibit high affinity for the BZD receptor and BZD-like activity in vivo. In vitro, SR 95195 displaced specifically bound [3H]-flunitrazepam from rat cerebellar and hippocampal membranes with respective IC50 values of 4 and 8 microM. In vivo, SR 95195 lacked BZD-like activity. At high doses SR 95195 induced clonic seizures in mice (threshold convulsant dose: 150 mg kg-1; CD50: 160 mg kg-1 i.p.) which were antagonized by Ro 15-1788. At non-convulsant doses (25 mg kg-1 i.p. and 100 mg kg-1 i.p.) SR 95195 significantly decreased punished responding in an operant conflict procedure in the rat, suggesting SR 95195 has intrinsic anxiogenic activity. SR 95195, in mice, reversed the anticonvulsant and myorelaxant actions of diazepam 3 mg kg-1, orally (respective ED50 values: 45 mg kg-1 i.p. and 44 mg kg-1 i.p.). In an operant-conflict test in rats, SR 95195 at non-anxiogenic doses, antagonized the disinhibitory action of diazepam 4 mg kg-1, i.p. (ED50: 8.6 mg kg-1, i.p.), but not that of pentobarbitone 15 mg kg-1, i.p. It is concluded that SR 95195 has the pharmacological profile of an inverse BZD agonist and that displacing the phenyl from the 6- to the 7-position in the triazolopyridazine series causes a shift from agonist to inverse agonist type activity at the BZD receptor site. PMID:3028557

  2. A New Phenyl Ethyl Glycoside from the Twigs of Acer tegmentosum.

    PubMed

    Park, Seonju; Lee, Hwa Young; Nhiem, Nguyen Xuan; Lee, Taek Hwan; Kim, Nanyoung; Cho, Seung Hun; Kim, Seung Hyun

    2015-07-01

    One new phenyl ethyl glycoside, 2-(4-hydroxyphenyl)ethyl-O-α-L-arabinofuranosyl-(1 --> 6)-O-β-D-glucopyranoide (1) and 11 known compounds (2-12) were isolated from the twigs of Acer tegmentosum. Compound 6 showed potent anti-neuroinflammatory activity against the LPS-stimulated BV-2 microglial cells with tNO production of 25.0 ± 2.5 μM and TNF-α concentration of 617.6 ± 47.1 pg/mL at 30 μM.

  3. 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

  4. 2-(3,4-Dichloro-phen-yl)-4-phenyl-benzo[h]quinoline.

    PubMed

    Wu, Nan; Xu, Zhou

    2011-11-01

    In the title compound, C(25)H(15)Cl(2)N, the benzo[h]quinoline system exhibits an approximately planar conformation with an r.m.s. deviation of 0.0202Å and a maximum deviation of 0.039 (1) Å. The aryl group at position 2 is nearly coplanar with the parent ring [dihedral angle = 6.68 (7)°] while the parent ring and the phenyl subsitituent at position 4 form a dihedral angle of 67.11 (4)°. Inter-molecular C-H⋯π inter-actions stabilize the crystal packing. PMID:22219893

  5. (E)-1-(4-Meth-oxy-anthracen-1-yl)-2-phenyl-diazene.

    PubMed

    Crochet, Aurelien; Fromm, Katharina M; Kurteva, Vanya; Antonov, Liudmil

    2011-04-01

    The title compound, C(21)H(16)N(2)O, has an E-conformation about the diazene N=N bond. It is reasonably planar with the phenyl ring being inclined to the mean plane of the anthracene moiety [planar to within 0.077 (3) Å] by 6.43 (10)°. The crystal structure is stabilized by C-H⋯π and weak π-π inter-actions [centroid-centroid distances of 3.7192 (16) and 3.8382 (15) Å], leading to the formation of two-dimensional networks stacking along [001] and lying parallel to (110).

  6. Pharmacological properties of 3-phenyl-5β diethylaminoethyl-1,2,4-oxadiazole

    PubMed Central

    Silvestrini, B.; Pozzatti, C.

    1961-01-01

    The general pharmacological properties of Oxolamine (3-phenyl-5β-diethylaminoethyl-1,2,4-oxadiazole) are described. The antitussive activity of this drug is more apparent in tests involving a diffuse stimulation of the bronchial tree than with electrical stimulation of the superior laryngeal nerve. These results suggest a predominantly peripheral mechanism of action. Oxolamine also possesses analgesic-anti-inflammatory, local anaesthetic and antispasmodic properties. The acute and chronic toxicities of Oxolamine are low, and the experimental results indicate the absence of side effects. The possibility that the antitussive activity is related to the other pharmacological properties is discussed. PMID:19108149

  7. 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.

  8. 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.

  9. 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

  10. 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.

  11. 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

  12. 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

  13. 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.

  14. 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

  15. 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.

  16. Palladium supported on chitosan as a recyclable and selective catalyst for the synthesis of 2-phenyl ethanol.

    PubMed

    Dabbawala, Aasif A; Sudheesh, N; Bajaj, Hari C

    2012-03-14

    Two different chitosan supported palladium based catalysts were prepared, wherein dispersed palladium nanoparticles were obtained via chemical reduction supported on chitosan (Pd/CTS) and amine functionalized modified chitosan (Pd/AFCTS). The catalytic activity of the Pd-based catalysts, Pd/CTS and Pd/AFCTS, were assessed in the hydrogenation of styrene oxide to 2-phenyl ethanol. Both Pd-based catalysts enhanced the formation of the desired 2-phenyl ethanol in contrast to a conventional Pd/C catalyst without the assistance of inorganic or organic base. A considerable influence on the conversion and selectivity was observed in the case of Pd/AFCTS, consisting of palladium nanoparticles stabilized and dispersed on amine-functionalized chitosan matrix, affording complete conversion of styrene oxide with 98% selectivity to 2-phenyl ethanol. The catalyst Pd/AFCTS has also been recycled without significant loss of activity and selectivity.

  17. 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.

  18. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine induced Parkinson's disease in zebrafish.

    PubMed

    Sarath Babu, Nukala; Murthy, Ch Lakshmi N; Kakara, Sameera; Sharma, Rahul; Brahmendra Swamy, Cherukuvada V; Idris, Mohammed M

    2016-05-01

    Parkinson's disease (PD) is the most common age associated neurodegenerative disease, which has been extensively studied for its etiology and phenotype. PD has been widely studied in alternate model system such as rodents towards understanding the role of neurotoxin by inducing PD. This study is aimed to understand the biomechanism of PD in zebrafish model system induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). The phenotype and role of various genes and proteins for Parkinsonism were tested and evaluated in this study using behavior, molecular and proteomic approaches. Zebrafish PD model induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine showed a significant level of decrease in the movement with erratic swimming pattern and increased freezing bouts. CHCHD2, EEF2B, LRRK2, PARK7, PARK2, POLG, SNCGB and SYNB genes were differentially regulated at the transcript level in PD zebrafish. Similarly a total of 73 proteins were recognized as differentially expressed in the nervous system of zebrafish due to Parkinsonism based on quantitative proteomics approach. Proteins such as NEFL, MUNC13-1, NAV2 and GAPVD1 were down regulated in the zebrafish brain for the PD phenotype, which were associated with the neurological pathways. This zebrafish based PD model can be used as a potential model system for screening prospective drug molecules for PD. PMID:26959078

  19. 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.

  20. 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.

  1. Synthesis, crystal structure and potential antimicrobial activities of di (4-sulfamoyl-phenyl-ammonium) sulphate.

    PubMed

    Essghaier, Badiaa; Naouar, Amani; Abdelhak, Jawher; Zid, Mohamed Faouzi; Sadfi-Zouaoui, Najla

    2014-01-01

    A new organic-inorganic hybrid SO4[C6H9N2O2S]2, has been synthesized and characterized by X-ray diffraction. This compound crystallizes in the orthorhombic system, spaces group Pbcn. In the title compound, the packing is stabilized by intermolecular N-H⋯O hydrogen bonds and π-π stacking interactions between the phenyl rings, linking the molecules into three-dimensional network. The in vitro antimicrobial activity of di (4-sulfamoyl-phenyl-ammonium) sulphate was determined by the broth dilution method against several strains selected to define their spectrum and potency. Here we show that the synthetic sulfanilamide exhibits promising antibacterial potency. High inhibition was also detected against Candida albicans. In this paper we firstly showed the antifungal activity of the sulfanilamide against two serious phytopathogenic fungi. Interestingly, the new compound was able to suppress mycelial growth as well as the spores germination of tested fungi, values of spore germination vary from 97.6% to 37.5%, respectively for Botrytis cinerea and Fusarium species. The minimal inhibitory concentrations (MIC) ranging from 8 to 100 μg ml(-1) and IC50 values varying from 5.81 to less than 100 μg ml(-1)), showed that the sulfanilamide sulphate had high activity against bacteria, yeast and fungi, compared to others published antifungal compounds. PMID:24472654

  2. 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.

  3. 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

  4. Photochemical oxidation processes for the elimination of phenyl-urea herbicides in waters.

    PubMed

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

    2006-11-16

    Four phenyl-urea herbicides (linuron, chlorotoluron, diuron, and isoproturon) were individually photooxidized by monochromatic UV radiation in ultra-pure aqueous solutions. The influence of pH and temperature on the photodegradation process was established, and the first-order rate constants and quantum yields were evaluated. The sequence of photodecomposition rates was: linuron>chlorotoluron>diuron>isoproturon. The simultaneous photooxidation of mixtures of the selected herbicides in several types of waters was then performed by means of UV radiation alone, and by UV radiation combined with hydrogen peroxide. The types of waters used were: ultra-pure water, a commercial mineral water, a groundwater, and a lake water. The influence of the independent variables in these processes - the presence or absence of tert-butyl alcohol, types of herbicide and waters, and concentration of hydrogen peroxide - were established and discussed. A kinetic study was performed using a competitive kinetic model that allowed various rate constants to be evaluated for each herbicide. This kinetic model allows one to predict the elimination of these phenyl-urea herbicides in contaminated waters by the oxidation systems used (UV alone and combined UV/H2O2). The herbicide concentrations predicted by this model agree well with the experimental results that were obtained.

  5. N,N′-Bis(phenyl­carbamo­thio­yl)benzene-1,3-dicarboxamide

    PubMed Central

    Ngaini, Zainab; Mohd Ariff, Maya Asyikin; Wan Zullkiplee, Wan Sharifatun Handayani; Hussain, Hasnain; Rosli, Mohd Mustaqim

    2013-01-01

    The asymmetric unit of the title compound, C22H18N4O2S2, contains two mol­ecules. In one of them, the dihedral angles between the central benzene ring and the phenyl rings are 16.97 (8) and 20.97 (8)°, while the phenyl rings make a dihedral angle of 37.87 (8)°. In the other mol­ecule, the corresponding values are 34.92 (7), 53.90 (7) and 60.68 (8)°, respectively. In each mol­ecule, two intra­molecular N—H⋯O hydrogen bonds generate S(6) rings and a short C—H⋯S contact also occurs. In the crystal, N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S inter­actions link the mol­ecules into a three-dimensional network. PMID:24427019

  6. 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.

  7. 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

  8. The UV Spectroscopy of Jet-Cooled 3-PHENYL-2-PROPYNENITRILE

    NASA Astrophysics Data System (ADS)

    Jawad, Khadija M.; Zwier, Timothy S.

    2016-06-01

    The atmosphere of Saturn's moon Titan is replete with hydrocarbons and nitriles, but knowledge of the formation and sink processes as well as the identities of molecules on the large end of photochemical models of the atmosphere is very limited. 3-phenyl-2-propynenitrile (Ph-C≡C-C≡N) is of potential importance in this atmosphere because it is a likely product of photochemical reaction between cyanoacetylene and benzene, bringing together two of the key functional groups in Titan's atmosphere in a single molecule. We present the UV spectrum of this molecule in the gas phase, under jet-cooled conditions, using 2-color resonant two-photon ionization. The spectrum was recorded from 292-208nm, taking advantage of the wide tunability of a BBO-based OPO as the excitation source. On its long wavelength end, the spectrum has sharp transitions arising from a ΠΠ* transition characteristic of a phenyl derivative, while deeper into the UV the spectrum is broadened in a manner reminiscent of cyanoacteylene.

  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, 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]...

  10. 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]...

  11. 2-Amino-4-phenyl-5,6-dihydro-benzo[h]quinoline-3-carbonitrile-3-amino-1-phenyl-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (5/3).

    PubMed

    Asiri, Abdullah M; Al-Youbi, Abdulrahman O; Faidallah, Hassan M; Ng, Seik Weng

    2011-11-01

    The asymmetric unit of the 5:3 title co-crystal of 2-amino-4-phenyl-5,6-dihydro-benzo[h]quinoline-3-carbonitrile and 3-amino-1-phenyl-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.625C(20)H(15)N(3).0.375C(22)H(15)N(3), has the atoms of the fused-ring system and those of the amino, cyano and phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring, the two flanking aromatic rings being twisted by 20.1 (1)°. This ethyl-ene portion is disordered over two positions in a 1:1 ratio. The phenyl ring is twisted by 69.5 (1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, two mol-ecules are linked by an N-H⋯N hydrogen bond, generating a a helical chain along [010]. PMID:22219912

  12. Radiationless S 1 → S 0 phenyl deactivation pathway: an investigation of iodine-marked bi-phenyl on a silicon surface by means of time resolved core-level photoelectron spectroscopy

    NASA Astrophysics Data System (ADS)

    Michelswirth, Martin; Dachraoui, Hatem; Mattay, Jochen; Heinzmann, Ulrich

    2012-02-01

    The S 1 → S 0 radiationless deactivation of iodine terminated bi-phenyl immobilized on a silicon surface was probed by analysing the I4d signature (BE: 45.6 eV, 47.3 eV) by means of High Harmonic Generation (HHG) based photoelectron spectroscopy. Modifications of the 4d5/2,3/2 spectroscopic contents spanning about 0.2 ps after UV activation (266 nm) were verified as showing a transient molecular response character. A localization to the terminated phenyl substructure in the complex structural environment on the surface was ensured according to the core-level nature of the recorded I4d. The activation of the bi-phenyl achieved by UV irradiation, corresponding to the UV absorption band-edge, was verified as being dominated by a Bπ → Bπ* phenyl excitation. Time-Dependent Density Functional Theory (TD-DFT) modellings were therefore performed. They were matched to Configuration Interaction semi-empirical calculations (CI-MNDO) verifying the Rustagi-Ducuing relation. The simulated singlet-singlet excitation spectrum was referenced to the spectra of an iodine terminated monomer and a linear oligophenyl chain (N = 8). Thus the deactivation response studied was assigned to a conical intersection promoted ? reaction pathway.

  13. 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

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

    NASA Astrophysics Data System (ADS)

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

    2009-12-01

    A new sensitive and selective spectrophotometric method has been developed for the determination of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid in pharmaceuticals in the presence of nicotinic acid. The method is based on the reaction of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid with 1,3,3-trimethyl-5-phenyl-2-[3-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-propenyl]-3 H-indolium chloride (PIC) followed by the extraction of the formed ion associate into toluene and spectrophotometric detection at 581 nm. Appropriate experimental conditions were found to be pH 7.8-9.8 and 3.6 × 10 -4 mol L -1 of PIC. The molar absorptivity is 5.0 × 10 -4 L mol -1 cm -1. The absorbance obeys Beer's law in the range 0.61-12.60 μg mL -1 of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid, and the detection limit calculated from a blank test was 0.20 μg mL -1.

  16. 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

  17. 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…

  18. 2D IR photon echo study of the anharmonic coupling in the OCN region of phenyl cyanate

    PubMed Central

    Tucker, Matthew J.; Kim, Yung Sam; Hochstrasser, Robin M.

    2009-01-01

    The vibrations in the OCN stretching region of phenyl cyanate are examined by two-dimensional infrared spectroscopy. In water and THF, these spectra display three diagonal peaks having cross peaks characteristic of anharmonically coupled transitions. The pattern of the spectra is reproduced by coupling of two overtones with the OCN fundamental. PMID:20160952

  19. 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.

  20. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.267 N- diallylamino-4- substituted phenyl] acetamide (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance...

  1. 40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.267 N- diallylamino-4- substituted phenyl] acetamide (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance...

  2. Annulation Reactions of Donor-Acceptor Cyclopropanes with (1-Azidovinyl)benzene and 3-Phenyl-2H-azirine.

    PubMed

    Curiel Tejeda, Joanne E; Irwin, Lauren C; Kerr, Michael A

    2016-09-16

    Under the influence of heat and Lewis acid, donor/acceptor cyclopropanes underwent annulation reactions with (1-azidovinyl)benzene and 3-phenyl-2H-azirine to form an unusual azabicyclic scaffold with an imbedded aziridine. The mechanism of reaction is believed to proceed via a vinyl nitrene intermediate. PMID:27598518

  3. Comparative adsorption of phenyl selenolate and selenocyanate on Au nanoparticle surfaces

    NASA Astrophysics Data System (ADS)

    Lim, Jong Kuk; Joo, Sang-Woo

    2007-03-01

    UV-vis absorbance spectra taken at different elapsed time for the surface plasmon band shift indicated that the self-assembly of PhSeCN on gold should be slower than that of phenyl selenolate (PhSeH). A surface-enhanced Raman scattering (SERS) study showed that a trace amount of CN species could remain on Au surfaces when aromatic selenocyanates are reduced to give CN and their selenium atoms bound to the surface. Our concentration dependent SERS spectra suggested that the CN adsorption should be more favorable at higher concentrations of PhSeCN as indicated from more prominent intensites of the CN stretching vibration at 2110-2150 cm -1.

  4. Unexpected effect of substituents on the zero-field splitting of triplet phenyl nitrenes

    NASA Astrophysics Data System (ADS)

    Korchagin, Denis V.; Akimov, Alexander V.; Yureva, Elena A.; Aldoshin, Sergei M.; Misochko, Eugenii Ya.

    2016-08-01

    The EPR spectrum of triplet 2,4,6-tribromophenyl nitrene was obtained in glassy methylcyclohexane at 15 K. Surprisingly, the zero-field splitting parameter D = 0.989 cm-1 derived from this spectrum is much lower than that reported previously for triplet 3,5-diazido-2,4,6-tribromophenyl nitrene and has the same value as in phenyl nitrenes composed with light atoms. DFT calculations of the zero-field splitting parameters support this unexpected experimental observation. Experimental and theoretical data provide evidence that the enhanced by bromine atoms spin-orbit contribution to the parameter D (the so called "heavy-atom effect") is strongly modulated by other substituents attached to the aromatic cycle.

  5. Potassium [(1S)-1-azido-2-phenyl­eth­yl]trifluorido­borate

    PubMed Central

    Lejon, Tore; Gorovoy, Alexey S.; Khrustalev, Victor N.

    2012-01-01

    The title compound, K+·C8H8BF3N3 −, is a salt containing the chiral organic trifluorido­borate anion. The organic anions and potassium cations are tightly bound to each other by the coordination K—F [2.654 (3)–3.102 (3) Å] and K—N [2.951 (4)–3.338 (4) Å] inter­actions. Thus, the potassium cation adopts a nine-vertex coordination polyhedron, which can be described as a distorted monocapped tetra­gonal anti­prism. In the crystal, the organic anions and potassium cations form layers parallel to (001). Weak C—H⋯π inter­actions between neighbouring phenyl rings further stabilize the crystal. PMID:22904724

  6. 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.

  7. Characterization of antiproliferative potential and biological targets of a copper compound containing 4'-phenyl terpyridine.

    PubMed

    Mendo, Ana Soraia; Figueiredo, Sara; Roma-Rodrigues, Catarina; Videira, Paula A; Ma, Zhen; Diniz, Mário; Larguinho, Miguel; Costa, Pedro M; Lima, João C; Pombeiro, Armando J L; Baptista, Pedro V; Fernandes, Alexandra R

    2015-09-01

    Several copper complexes have been assessed as anti-tumor agents against cancer cells. In this work, a copper compound [Cu(H2O){OS(CH3)2}L](NO3)2 incorporating the ligand 4'-phenyl-terpyridine antiproliferative activity against human colorectal, hepatocellular carcinomas and breast adenocarcinoma cell lines was determined, demonstrating high cytotoxicity. The compound is able to induce apoptosis and a slight delay in cancer cell cycle progression, probably by its interaction with DNA and induction of double-strand pDNA cleavage, which is enhanced by oxidative mechanisms. Moreover, proteomic studies indicate that the compound induces alterations in proteins involved in cytoskeleton maintenance, cell cycle progression and apoptosis, corroborating its antiproliferative potential.

  8. Dicyclo-hexyl-ammonium trimethyl-bis-(hydrogen phenyl-phospho-nato)stannate(IV).

    PubMed

    Diop, Tidiane; Diop, Libasse; Diop, Cheikh A K; Molloy, Kieran C; Kociok-Köhn, Gabriele

    2011-12-01

    In the title compound, (C(12)H(24)N)[Sn(CH(3))(3)(C(6)H(6)O(3)P)(2)], the SnMe(3) residues are axially coordinated by two monodentate [PhPO(3)H](-) anions, leading to a trigonal-bipyramidal geometry for the Sn(IV) atom. The two [SnMe(3)(PhPO(3)H)(2)](-) anions in the unit cell are associated into infinite chains along the a axis by O-H⋯O hydrogen bonds involving the hy-droxy group of the hydrogen phenyl-phospho-nate ion. The chains inter-act with one another via O-H⋯O hydrogen bonds along the c axis. These networks of anions assemble with the dicyclo-hexyl-ammonium ion through N-H⋯O hydrogen bonds, forming a three-dimensional network. PMID:22199636

  9. 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

  10. 2,4,6-Tri­nitro­phenyl 3-bromo­benzoate

    PubMed Central

    Moreno-Fuquen, Rodolfo; Mosquera, Fabricio; Ellena, Javier; Tenorio, Juan C.

    2014-01-01

    In the title picryl-substituted ester, C13H6BrN3O8, the mean plane of the central ester C–O–C(=O)–C fragment (r.m.s. deviation= 0.0186 Å) is rotated by 84.73 (7)° and 19.92 (12)° to the picryl and phenyl rings, respectively. In the crystal, the mol­ecules are linked by C—H⋯O inter­actions, forming centrosymmetric dimers enclosing R 2 2(10) and R 2 2(22) ring motifs along [001] and further helical chains of dimers enclosing R 2 2(10) ring motifs along [010]. PMID:24940266

  11. 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

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

    PubMed

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

    2013-01-01

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

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

    PubMed

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

    2015-07-01

    Polymer light-emitting diodes (PLEDs) have attracted much attention from academia and industry field because of their various applications such as large area flat-panel displays and lightings. In this paper, we suggest new blue emitting polymer based on anthracene, Poly(9-(3-Vinyl-phenyl)-anthracene) (PVPA). From NMR data, vinyl group protons were disappeared and aromatic protons showed broad proton peaks because of polymer characteristics. PVPA had film property well and it exhibited vivid PL maximum values of 431, 455, 482 nm and broad PL spectrum. Three dopants for green, red, yellow were used to PVPA, all energy transfer was happened well. By using rubrene dopant of yellow emission, doped film provided white PL. PMID:26373155

  14. 3-Acetyl-6-chloro-2-methyl-4-phenyl­quinolinium hydrogen sulfate

    PubMed Central

    Loh, Wan-Sin; Fun, Hoong-Kun; Sarveswari, S.; Vijayakumar, V.; Reddy, B. Palakshi

    2009-01-01

    In the title salt, C18H15ClNO+·HSO4 −, the quinolinium ring system is approximately planar, with a maximum deviation of 0.028 (2) Å, and forms a dihedral angle of 78.43 (4)° with the attached phenyl ring. A pair of inter­molecular O—H⋯O hydrogen bonds links two hydrogen sulfate anions into a dimer, generating a R 2 2(8) ring motif. Inter­molecular N—H⋯O hydrogen bonds and C—H⋯O contacts link the ions into a three-dimensional network. The structure is further stabilized by C—H⋯π inter­actions PMID:21578864

  15. 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.

  16. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  17. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  18. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

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

  19. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  20. 40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  1. 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

  2. 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.

  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. Anion-Controlled Positional Switching of a Phenyl Group about the Dinuclear Core of a AuSb Complex.

    PubMed

    Sen, Srobona; Ke, Iou-Sheng; Gabbaï, François P

    2016-09-19

    As part of our continuing interest in redox-active, anion-responsive main-group transition-metal platforms, we have investigated the effect of chloride by fluoride anion substitution on the core structure of a dinuclear AuSb platform. Starting from [(o-(iPr2P)C6H4)2Cl2SbPh]AuCl (2) in which the antimony-bound phenyl group is positioned trans to the gold atom, we found that the introduction of fluoride anions, as in [(o-(iPr2P)C6H4)2F2SbPh]AuCl (3) and [(o-(iPr2P)C6H4)2ClFSbPh]AuCl (4), produces structures in which the phenyl group switches to a perpendicular direction with respect to the gold atom. Replacement of the gold-bound chloride anion in 3 by a fluoride anion can be achieved by successive treatment with TlPF6 and [nBu4N][Ph3SiF2]. These reactions, which proceed via the intermediate zwitterionc gold antimonate complex [o-(iPr2P)C6H4)2F3SbPh]Au (6), trigger migration of the phenyl group to gold and afford [(o-(iPr2P)C6H4)2F3Sb]AuPh (7). Because the phenyl group in 7 is orthogonal to that in 3 and opposite to that in 2, the title AuSb platform can be regarded as a molecular analogue of a mechanical three-way switch in which the switching element is a phenyl group. Finally, while all complexes involved retain a Au → Sb interaction, this interaction is no longer present in the zwitterionic derivative 6 because of the neutralization of the Lewis acidity of the antimony center. PMID:27583565

  5. 1-[(2S)-1-Chloro-3-phenyl­propan-2-yl]-2,4,5-triphenyl-1H-imidazole

    PubMed Central

    Xiao, Yongmei; Yang, Liangru; He, Kun; Yuan, Jinwei; Mao, Pu

    2012-01-01

    In the title compound, C30H25ClN2, the chiral center maintains the S configuration of the stating l-phenyl­alaninol. The two phenyl groups closest to the substituted N atom adopt an almost perpendicular orientation relative to the central imidazole ring, with dihedral angles of 88.9 (4) and 84.7 (3)°. The third phenyl group is nearly coplanar with it, making a dihedral angle of 11.0 (5)°. PMID:22606099

  6. (S)-4,5-Diphenyl-1-[1-phenyl-3-(phenyl­sulfan­yl)propan-2-yl]-2-(thio­phen-2-yl)-1H-imidazole

    PubMed Central

    Gao, Jie; Wang, Hongyan; Yang, Liangru; Xiao, Yongmei; Mao, Pu

    2013-01-01

    In the title compound, C34H28N2S2, the central imidazole ring (r.m.s. deviation = 0.0015 Å) forms dihedral angles of 55.7 (3), 17.94 (11) and 86.27 (11)°, respectively, with the mean planes of the attached thienyl and two phenyl substituents. The thienyl ring shows ring-flip disorder [occupancy ratio = 0.647 (2):0.353 (2)]. The chiral centre maintains the S configuration of the l-phenyl­alaninol starting material. Intra- and inter­molecular C—H⋯S hydrogen bonds involving the disordered thienyl ring are observed. PMID:24454271

  7. 2-[3,4-Dibut-oxy-5-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-thien-yl]-5-phenyl-1,3,4-oxadiazole.

    PubMed

    Li, Hai-Lin; Zeng, Hai-Su; Kang, Si-Shun; Wang, Hai-Bo

    2008-07-05

    In the title compound, C(28)H(28)N(4)O(4)S, the dihedral angles between the central thio-phene ring and its pendant oxadiazole rings are 1.2 (3) and 9.8 (3)°. The dihedral angles between the oxadiazole and phenyl rings are 2.9 (3) and 1.8 (3)°. Some short intra-molecular C-H⋯O contacts occur.

  8. 2-[3,4-Dibut­oxy-5-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-thien­yl]-5-phenyl-1,3,4-oxadiazole

    PubMed Central

    Li, Hai-lin; Zeng, Hai-su; Kang, Si-shun; Wang, Hai-bo

    2008-01-01

    In the title compound, C28H28N4O4S, the dihedral angles between the central thio­phene ring and its pendant oxadiazole rings are 1.2 (3) and 9.8 (3)°. The dihedral angles between the oxadiazole and phenyl rings are 2.9 (3) and 1.8 (3)°. Some short intra­molecular C—H⋯O contacts occur. PMID:21203138

  9. 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

  10. Synthesis and analgesic activity of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones and 3-(substituted phenyl)-1,2,3-triazolo[4,5-b]pyridines.

    PubMed

    Clark, R L; Pessolano, A A; Shen, T Y; Jacobus, D P; Jones, H; Lotti, V J; Flataker, L M

    1978-09-01

    In a study of nonsteroidal antiinflammatory and analgesic agents, a series of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones-and 3-(substituted phenyl)triazolo[4,5-b]pyridines was prepared. Many of the imidazolones were alkylated on the free nitrogen. In a modified Randall-Selitto analgesic assay, the pain thresholds of both the inflamed and normal foot were elevated. This is not commonly observed with nonsteroidal antiinflammatory agents. The most active compounds were 1,3-dihydro-3[3,4-(methylenedioxy)phenyl]imidazo[4,5-b]pyridin-2-one (I-15) and its N-allyl (I-21) and N-isopropyl (I-121) derivatives. In the triazole series the 3-(2-fluoro- and 2,4-difluorophenyl)triazolo[4,5-b]pyridines (T-1 and T-8) were the best. The imidazole compounds were somewhat superior in analgesic activity to codeine and d-propoxyphene without showing any narcotic characteristics. Some of the compounds also possessed activity against carrageenan-induced foot edema in the rat, so these compounds represent a new class of nonnarcotic analgesic antiinflammatories, capable of producing a greater degree of analgesia than that obtainable with other nonsteroidal antiinflammatory agents.

  11. 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

  12. Synthesis and spectral studies of metal complexes of a Schiff base derived from (2-amino-5-chlorophenyl)phenyl methanone.

    PubMed

    Mini, S; Sadasivan, V; Meena, S S; Bhatt, Pramod

    2015-01-01

    Some new complexes of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Fe(III) with the Schiff base 5-chloro-2-(furan-2-yl methylamino)phenyl)phenyl methanone has been synthesized and characterized by elemental analysis, spectroscopic data including FT-IR, (1)H NMR, Electronic, ESI mass, Mössbauer & ESR. It has been found that the Schiff base behaves as a neutral bidentate N, O donor which chelates with the metal ions in 1:2 stoichiometry. Magnetic moment and electrolytic conductance data confirms this. The Schiff base and selected complexes were screened for antimicrobial activity. The complexes and the Schiff base were subjected to antioxidant study. The antitumor activity of Co(II) complex was tested by MTT assay. The result indicates the viability of the complex against tested cell lines.

  13. 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.

  14. Crystal structure of 2-[2-(hy-droxy-imino)-1-phenyl-propyl-idene]-N-phen-ylhydrazinecarbo-thio-amide.

    PubMed

    Anderson, Brian J; Freedman, Michael B; Millikan, Sean P; Smolenski, Victoria A; Jasinski, Jerry P

    2015-10-01

    In the title compound, C16H16N4OS, an intra-molecular C-H⋯S hydrogen bond is observed. With the exception of the phenyl ring of the phenyl-propyl-idene unit, the remainder of the mol-ecule has an almost planar skeleton with an r.m.s. deviation of 0.121 (5) Å from the plane through the remaining 16 atoms. In the crystal O-H⋯N hydrogen bonds are observed between the terminal hy-droxy-imino groups, forming inverson dimers with R 2 (2)(6) graph-set motifs. Additional C-H⋯N contacts stack the dimers along [100]. While no π-π inter-actions are present, weak C-H⋯O and O-H⋯Cg inter-actions are also observed and help stabilize the crystal packing.

  15. 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

  16. 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

  17. 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.

  18. Crystal structure of 2-[2-(hy-droxy-imino)-1-phenyl-propyl-idene]-N-phen-ylhydrazinecarbo-thio-amide.

    PubMed

    Anderson, Brian J; Freedman, Michael B; Millikan, Sean P; Smolenski, Victoria A; Jasinski, Jerry P

    2015-10-01

    In the title compound, C16H16N4OS, an intra-molecular C-H⋯S hydrogen bond is observed. With the exception of the phenyl ring of the phenyl-propyl-idene unit, the remainder of the mol-ecule has an almost planar skeleton with an r.m.s. deviation of 0.121 (5) Å from the plane through the remaining 16 atoms. In the crystal O-H⋯N hydrogen bonds are observed between the terminal hy-droxy-imino groups, forming inverson dimers with R 2 (2)(6) graph-set motifs. Additional C-H⋯N contacts stack the dimers along [100]. While no π-π inter-actions are present, weak C-H⋯O and O-H⋯Cg inter-actions are also observed and help stabilize the crystal packing. PMID:26594484

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

    PubMed Central

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

    2011-01-01

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

  20. N-heteroaryl-2-phenyl-3-(benzyloxy)piperidines: a novel class of potent orally active human NK1 antagonists.

    PubMed

    Ladduwahetty, T; Baker, R; Cascieri, M A; Chambers, M S; Haworth, K; Keown, L E; MacIntyre, D E; Metzger, J M; Owen, S; Rycroft, W; Sadowski, S; Seward, E M; Shepheard, S L; Swain, C J; Tattersall, F D; Watt, A P; Williamson, D W; Hargreaves, R J

    1996-07-19

    The preparation of a series of N-heteroarylpiperidine ether-based human NK1 antagonists is described. Two of the compounds 3-[-(2S,3S)-3-(((3,5-bis(trifluoromethyl)phenyl)methyl)oxy)- 2-phenylpiperidino}methyl]-1,2,4-triazole (11) and 5-[¿(2S,3S)-3-(((3,5-bis(trifluoromethyl)-phenyl)methyl)oxy)-2- phenylpiperidino}methyl]-3-oxo-1,2,4-triazolone (12)), in particular, are orally bioavailable and exhibited significant improvements in potency, both in vitro and in vivo, over the lead (carboxamidomethyl)piperidine ether 1. Rat liver microsome studies on a selected number of compounds from this series show the triazolone heterocycle to be considerably more stable than the others. Furthermore, both 11 and 12 have been profiled in a number of assays that may be predictive of the clinical utility of substance P antagonists.

  1. 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

  2. 6-(4-Amino­phen­yl)-2-meth­oxy-4-phenyl­nicotino­nitrile

    PubMed Central

    Suwunwong, Thitipone; Chantrapromma, Suchada; Quah, Ching Kheng; Fun, Hoong-Kun

    2013-01-01

    In the structure of the title nicotino­nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino­phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π–π inter­actions between the 4-amino­phenyl rings of adjacent sheets, with centroid–centroid distances of 3.7499 (9) Å. C—H⋯π inter­actions are also present. PMID:24454245

  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. SMILES-based QSPR model for half-wave potentials of 1-phenyl-5-benzyl-sulfanyltetrazoles using CORAL

    NASA Astrophysics Data System (ADS)

    Toropov, Andrey A.; Nesmerak, Karel

    2012-06-01

    The CORAL software (http://www.insilico.eu/coral) was used to build up the SMILES-based quantitative structure-property relationship (QSPR) for half-wave potential of 1-phenyl-5-benzyl-sulfanyltetrazoles. The QSPR developed is one-variable model based on the optimal descriptors calculated with the Monte Carlo method. The approach has been checked with three random splits into the training and test sets. Mechanistic interpretations (structural alerts related to the endpoint) of the model are discussed.

  5. 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

  6. 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

  7. A m-benzyne to o-benzyne conversion through a 1,2-shift of a phenyl group.

    PubMed

    Blake, Michael E; Bartlett, Kevin L; Jones, Maitland

    2003-05-28

    Pyrolysis of two differently labeled versions of 3-phenylphthalic anhydride shows that a m-benzyne can form the related o-benzyne through shift of a phenyl group. The highest energy point in the process is the transition structure for a reverse carbon-hydrogen insertion in an intermediate benzopentalene. With the minor addition of an intermediate alkyne formed through a Roger Brown rearrangement, the original mechanism for formation of acenaphthalene accommodates the labeling results.

  8. 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.

  9. Discovery and Characterization of the N-phenyl-N 0 -Naphthylurea Class of p38 Kinase Inhibitors

    SciTech Connect

    Cirillo, P.; Hickey, E; Moss, N; Breitfelder, S; Betageri, R; Fadra, T; Gaenzler, F; Gilmore, T; Xiong, Z; et al.

    2009-01-01

    An effort aimed at exploring structural diversity in the N-pyrazole-N{prime}-naphthylurea class of p38 kinase inhibitors led to the synthesis and characterization of N-phenyl-N{prime}-naphthylureas. Examples of these compounds displayed excellent inhibition of TNF-{alpha} production in vitro, as well as efficacy in a mouse model of lipopolysaccharide induced endotoxemia. In addition, perspective is provided on the role of a sulfonamide functionality in defining inhibitor potency.

  10. 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.

  11. Magnetic resonance in films and photodiodes based on poly-(phenyl-phenylene-vinylene)

    NASA Astrophysics Data System (ADS)

    Dyakonov, V.; Rösler, G.; Schwoerer, M.; Blumstengel, S.; Lüders, K.

    1996-02-01

    Films of poly-(2-phenyl-1,4-phenylene-vinylene) (PPPV) and photodiodes with PPPV as an active layer were studied by optically (ODMR) and electrically (EDMR) detected electron-spin resonance (ESR). Two different signals were observed in ODMR: enhancement of the photoluminescence (PL) at g=2.01 due to recombination of the photogenerated polarons (s=1/2), and a half-field enhancement signal, attributed to the fusion of triplet excitons. Both processes lead to the formation of singlet excitons. The spectral dependence of the s=1/2 signal follows the low energy part of the PL spectrum, indicating that delayed recombination of distant polarons is influenced by ESR, whereas the cw PL contains both prompt and delayed contributions. The linewidth and the intensity of the ODMR signal depend on the PL excitation intensity. Both effects are due to a decrease of the recombination lifetime of the polaron pairs at higher intensities. The relative decrease of the short-circuit photocurrent ISC through a PPPV photodiode by ESR saturation is due to recombination of nonthermalized, nongeminate excess charge polarons in the active layer of the device. This effect is at least two orders of magnitude stronger than the enhancement of total PL at the same temperature. This feature is found to be common for conjugated polymers investigated so far, and reflects the fact that the total photogenerated ISC is spin dependent, whereas ODMR selects only the nongeminate portion of recombining species in the sample.

  12. 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

  13. Conformational Analysis and Rotational Barriers of Alkyl- and Phenyl-Substituted Urea Derivatives

    SciTech Connect

    Bryantsev, Vyacheslav; Firman, Timothy K.; Hay, Benjamin P.

    2005-02-10

    Potential energy surfaces (PES) for rotation about the N-C(sp3) or N-C(aryl) bond and energies of stationary points on PES for rotation about the C(sp2)-N bond are reported for methylurea, ethylurea, isopropylurea, t-butylurea and phenylurea using the B3LYP/DZVP2 and MP2/aug-cc-pVDZ methods. The analysis of alkylureas reveals cis and (less stable) trans isomers that adopt anti geometries, whereas syn geometries do not correspond to stationary points. In contrast, the analysis of phenylurea reveals that the lowest energy form at the MP2 level is a trans isomer in a syn geometry. The fully optimized geometries are in good agreement with crystal structure data, and PESs are consistent with the experimental dihedral angle distribution. Rotation about the C(sp2)-N bond in alkylureas and phenylurea is slightly more hindered (8.6-9.4 kcal/mol) than the analogous motion in the unsubstituted molecule (8.2 kcal/mol). At the MP2 level of theory, the maximum barriers to rotation for the methyl, ethyl, isopropyl, t-butyl and phenyl groups are predicted to be 0.9, 6.2, 6.0, 4.6 and 2.4 kcal/mol, respectively. The results are used to benchmark the performance of the MMFF94 force field. Systematic discrepancies between MMFF94 and MP2 results were improved by modification of several torsional parameters.

  14. 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.

  15. A polymorph of 2,4-dinitro­phenyl­hydrazine

    PubMed Central

    Amimoto, Kiichi; Nishiguchi, Hiromitsu

    2013-01-01

    The crystal structure of a previously unreported polymorph (form II) of 2,4-dinitro­phenyl­hydrazine (DNPH), C6H6N4O4, was determined at 90 K. The first polymorph (form I) is described in the monoclinic space group P21/c [Okabe et al. (1993 ▶). Acta Cryst. C49, 1678–1680; Wardell et al. (2006 ▶). Acta Cryst. C62, o318–320], whereas form II is in the monoclinic space group Cc. The mol­ecular structures in forms I and II are closely similar, with the nitro groups at the 2- and 4-positions being almost coplanar with the benzene ring [dihedral angles of 3.54 (1) and 3.38 (1)°, respectively in II]. However, their packing arrangements are completely different. Form I exhibits a herringbone packing motif, whereas form II displays a coplanar chain structure. Each chain in form II is connected to adjacent chains by the inter­molecular inter­action between hydrazine NH2 and 2-nitro groups, forming a sheet normal to (101). The sheet is stabilized by N—H⋯π inter­actions. PMID:23476598

  16. 9-Phenyl-4,5-diaza-9H-fluoren-9-ol monohydrate

    PubMed Central

    Yin, Guo-Jie; Yang, Gang-Bin; Wang, Shi-Min

    2012-01-01

    The title compound, C17H12N2O·H2O, was synthesized by the reaction of 4,5-diaza­fluoren-9-one with a Grignard reagent in ether (the reaction mixture being hydrolysed with saturated NH4Cl solution), and crystallizes with two organic mol­ecules and two water mol­ecules in the asymmetric unit. The 4,5-diaza­fluorene fragment is approximately planar, with r.m.s. deviations of 0.0448 and 0.0198 Å in the two mol­ecules. The dihedral angles between the 4,5-diaza­fluorene planes and the phenyl ring are 80.49 (6) and 76.57 (7)°. The crystal packing features O—H⋯N and O—H⋯O hydrogen bonds involving the bridging solvent water mol­ecules, which link the mol­ecules into a three-dimensional network. PMID:22719589

  17. Phenyl-alpha-tert-butyl nitrone reverses mitochondrial decay in acute Chagas' disease.

    PubMed

    Wen, Jian-Jun; Bhatia, Vandanajay; Popov, Vsevolod L; Garg, Nisha Jain

    2006-12-01

    In this study, we investigated the mechanism(s) of mitochondrial functional decline in acute Chagas' disease. Our data show a substantial decline in respiratory complex activities (39 to 58%) and ATP (38%) content in Trypanosoma cruzi-infected murine hearts compared with normal controls. These metabolic alterations were associated with an approximately fivefold increase in mitochondrial reactive oxygen species production rate, substantial oxidative insult of mitochondrial membranes and respiratory complex subunits, and >60% inhibition of mtDNA-encoded transcripts for respiratory complex subunits in infected myocardium. The antioxidant phenyl-alpha-tert-butyl nitrone (PBN) arrested the oxidative damage-mediated loss in mitochondrial membrane integrity, preserved redox potential-coupled mitochondrial gene expression, and improved respiratory complex activities (47 to 95% increase) and cardiac ATP level (>or=40% increase) in infected myocardium. Importantly, PBN resulted twofold decline in mitochondrial reactive oxygen species production rate in infected myocardium. Taken together, our data demonstrate the pathological significance of oxidative stress in metabolic decay and energy homeostasis in acute chagasic myocarditis and further suggest that oxidative injuries affecting mitochondrial integrity-dependent expression and activity of the respiratory complexes initiate a feedback cycle of electron transport chain inefficiency, increased reactive oxygen species production, and energy homeostasis in acute chagasic hearts. PBN and other mitochondria-targeted antioxidants may be useful in altering mitochondrial decay and oxidative pathology in Chagas' disease.

  18. Triazolyl phenyl disulfides: 8-Amino-7-oxononanoate synthase inhibitors as potential herbicides.

    PubMed

    Hahn, Hoh-Gyu; Choi, Jung-Sup; Lim, Hee Kyung; Lee, Kee-In; Hwang, In Taek

    2015-11-01

    The chemical validation of a potential herbicide target was investigated with 8-amino-7-oxononanoate synthase (AONS, also known as 7-keto-8-aminopelargonate synthase, KAPAS) and triazolyl phenyl disulfide derivatives in vitro and in vivo. AONS activity was completely inhibited by these synthesized compounds, with an IC50 of 48 to 592μM in vitro. Forty five-day old Arabidopsis thaliana plants were completely killed by representative compound KHG23844 {N-(2-fluorophenyl)-3-(phenyldisulphanyl)-1H-1,2,4-triazole-1-carboxamide} at the application rate of 250gha(-1) of foliar treatment in greenhouse conditions. Foliar application of 1000gha(-1) KHG23844 induced 2.3-fold higher l-alanine accumulation in the treated A. thaliana plants. Foliar supplement of 1mM biotin at 1 and 2days before KHG23844 application effectively recovered the growth inhibition of A. thaliana plant treated with KHG23844. The results strongly suggested that representative compound KHG23844 and its derivatives are potential AONS inhibitors.

  19. 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.

  20. 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.

  1. Novel nonsecosteroidal VDR ligands with phenyl-pyrrolyl pentane skeleton for cancer therapy.

    PubMed

    Ge, Zhixin; Hao, Meixi; Xu, Meng; Su, Zhigui; Kang, Zisheng; Xue, Lingjing; Zhang, Can

    2016-01-01

    A series of nonsecosteroidal vitamin D3 receptor (VDR) ligands with phenyl-pyrrolyl pentane skeleton were synthesized for cancer therapy. In contrast to 1α,25-dihydroxyvitamin D3 (Calcitriol), these VDR ligands exhibited anti-proliferative activity without inducing hypercalcemia. These compounds were evaluated for vitamin D3-agonistic ability and anti-proliferative activity in vitro. Among them, compounds 5k and 5i exhibited equivalent vitamin D3-agonistic activity compared with Calcitriol. Meanwhile, compound 5k displayed promising inhibiting profile against MCF-7, HepG-2 and Caco-2 with IC50 values of 0.00586 μM, 0.176 μM, and 1.01 μM (Calcitriol: 5.58 μM, 80.83 μM and 4.46 μM) respectively. Compound 5i inhibited proliferation of PC-3 with IC50 value of 0.00798 μM (Calcitriol: 17.25 μM). Additionally, neither of these compounds significantly elevated serum calcium in rats.

  2. 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.

  3. Theoretical study of phenyl-substituted indacenodithiophene copolymers for high performance organic photovoltaics.

    PubMed

    Chochos, Christos L; Avgeropoulos, Apostolos; Lidorikis, Elefterios

    2013-02-14

    The theoretical estimation of energy levels and energy gaps of conjugated polymers for organic photovoltaics (OPVs) represents in principle a useful tool for the prescreening of new donor systems as a suitable pair for the fullerene derivative [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM). In this study, ten tetraphenyl-substituted indacenodithiophene (IDT) copolymers (eight in the form of donor-acceptor), whose energy gaps vary in the range of 1.48-2.11 eV have been selected and their highest occupied molecular orbitals (HOMOs), lowest unoccupied molecular orbitals (LUMOs), and gap energies have been calculated by applying density functional theory (DFT) and/or time-dependent density functional theory (TD-DFT) methods. In spite of the examined molecular structure variety, nice correlations (theoretical models) between experimental and theoretical electronic parameters were found. It is shown that the theoretical band gap estimated by the TD-DFT using dimer model compounds and DFT using tetramer model compounds provide in good agreement the optical band gap of these polymers. Finally, the optimum theoretical limits of the LUMO offset between the fullerene and the IDT tetramer model compounds, for which high performance OPVs (efficiency > 6%) are obtained, is presented for the first time.

  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. 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.

  6. Reactions of charged phenyl radicals with aliphatic amino acids in the gas phase.

    PubMed

    Huang, Yiqun; Guler, Leo; Heidbrink, Jenny; Kenttämaa, Hilkka

    2005-03-23

    Gas-phase reactivity of five differently substituted positively charged phenyl radicals was examined toward six amino acids by using Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR). The reactivity of the radicals studied was determined by the electrophilicity of the radical, which can be characterized by the radical's electron affinity (EA). The larger the electron affinity of the radical, the higher the overall reaction rate. In addition to the expected H-atom abstraction, several unprecedented reaction pathways were observed, including NH2 abstraction, SH abstraction, and SCH3 abstraction. These reaction pathways dominate for the most electrophilic radicals, and they may not follow radical but rather nucleophilic addition-elimination mechanisms. Hydrogen abstraction from glycine was also investigated theoretically. The results indicate that hydrogen abstraction from alphaC of glycine is both kinetically and thermodynamically favored over the NH2 group. The ordering of transition state energies for hydrogen abstraction from the alphaC and NH2 groups was found to reflect the radicals' EA ordering.

  7. 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.

  8. 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).

  9. Rat Liver Mitochondrial Dysfunction Induced by an Organic Arsenical Compound 4-(2-Nitrobenzaliminyl) Phenyl Arsenoxide.

    PubMed

    Jiao, Yuan-Hong; Zhang, Qian; Pan, Ling-Li; Chen, Xin-You; Lei, Ke-Lin; Zhao, Jie; Jiang, Feng-Lei; Liu, Yi

    2015-12-01

    Arsenic is successfully used in cancer chemotherapy and several cancer treatments on account of its apoptogenic effects. However, it is environmentally hazardous with potential for toxicity when distributed in the soil, water, and food, and long exposure to water contaminated with Arsenic may induce cancers. Some research studies have reported that liver is the storage site and an important target organ for Arsenic toxicity. In the present work, a new kind of organic arsenic compound, 4-(2-nitrobenzaliminyl) phenyl arsenoxide (NPA), was synthesized, and its potential involvement of mitochondria was explored. The results presented that the toxicology of NPA, at least in part, mediated mitochondrial function and may thoroughly destroy mitochondrial membrane physiological functions. NPA induced mitochondrial permeability transition pore (mtPTP) opening that induces mitochondrial biochemical abnormalities as evidenced by mitochondrial swelling, mitochondrial membrane potential breakdown, membrane fluidity alterations, and the strikingly remarkable protection of CsA. Meanwhile, both the decreased respiration rate of state 4 and the increased inner membrane H(+) permeabilization revealed that the inner membrane function regarding important energy production chain was destroyed. The toxicity of NPA is due to its interaction with mitochondrial membrane thiol protein. This conclusion is based on the protective effects of RR, DTT, and MBM(+). PMID:26087905

  10. 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.

  11. (E)-3-Methyl-2,6-di­phenyl­piperidin-4-one O-(3-methyl­benzo­yl)oxime

    PubMed Central

    Kathiravan, V.; Krishnan, K. Gokula; Mohandas, T.; Thanikachalam, V.; Sakthivel, P.

    2014-01-01

    In the title compound, C26H26N2O2, the piperidine ring exhibits a chair conformation. The phenyl rings are attached to the central heterocycle in an equatorial position. The dihedral angle between the planes of the phenyl rings is 57.58 (8)°. In the crystal, C—H⋯O inter­actions connect the mol­ecules into zigzag chains along [001]. PMID:25249925

  12. 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...

  13. 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...

  14. 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...

  15. 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...

  16. 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...

  17. 2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: synthesis, reactions and biological activity.

    PubMed

    Husain, Asif; Khan, M S Y; Hasan, S M; Alam, M M

    2005-12-01

    2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (1-17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3H)-pyrrolones (18-23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3H)-pyrrolones (24-29) respectively, which were characterized on the basis of 1H-, 13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (5, 6, 7, 25 and 26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against Staphylococcus aureus and Escherichia coli as well as antifungal activity against Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound 21, 22 and 23 showed excellent activity against C. albicans with MIC-10 microg/ml. Out of the above-mentioned compounds, 22 and 23 also showed good activity against S. aureus with MIC-20 and 15 microg/ml respectively. PMID:15878219

  18. 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.

  19. Local description of the through phenyl transfer of a negative charge within resonance theory: topological effects in xylylene radical anions

    NASA Astrophysics Data System (ADS)

    Karafiloglou, Padeleimon; Launay, Jean-Pierre

    1999-11-01

    The topological effects specifying a di-substituted phenyl ring bearing a negative charge are investigated by considering the radical anions of para- and meta-xylylene isomers as model systems. The super exchange (SE) and double exchange (DE) component mechanisms describing the through phenyl transfer of a negative charge are considered and examined within `resonance' or `mesomeric' theory. The radical anion electronic events characterizing the DE and SE resonance structures are investigated by means of poly-electron population analysis. Correlated ab initio MO wavefunctions are used as the starting material in our calculations, and the various second quantized density operators are built on the basis of natural AOs. Conditional electronic events specifying SE or DE mechanisms are defined, and the corresponding probabilities are compared for meta and para topologies. The main trends are rationalized by comparing the effects provoked in phenyl ring when the negative charge is transferred from one substituent or the other. In para topology the effects are additive for the most important resonance structures, while in meta (characterized from `quantum interferences') the same effects are antagonist in all structures and for both SE and DE mechanisms.

  20. 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.

  1. para-Substituted 2-phenyl-3,4-dihydroquinazolin-4-ones as potent and selective tankyrase inhibitors.

    PubMed

    Haikarainen, Teemu; Koivunen, Jarkko; Narwal, Mohit; Venkannagari, Harikanth; Obaji, Ezeogo; Joensuu, Päivi; Pihlajaniemi, Taina; Lehtiö, Lari

    2013-12-01

    Human tankyrases are attractive drug targets, especially for the treatment of cancer. We identified a set of highly potent tankyrase inhibitors based on a 2-phenyl-3,4-dihydroquinazolin-4-one scaffold. Substitutions at the para position of the scaffold's phenyl group were evaluated as a strategy to increase potency and improve selectivity. The best compounds displayed single-digit nanomolar potencies, and profiling against several human diphtheria-toxin-like ADP-ribosyltransferases revealed that a subset of these compounds are highly selective tankyrase inhibitors. The compounds also effectively inhibit Wnt signaling in HEK293 cells. The binding mode of all inhibitors was studied by protein X-ray crystallography. This allowed us to establish a structural basis for the development of highly potent and selective tankyrase inhibitors based on the 2-phenyl-3,4-dihydroquinazolin-4-one scaffold and outline a rational approach to the modification of other inhibitor scaffolds that bind to the nicotinamide site of the catalytic domain. PMID:24130191

  2. (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

  3. Synthetic, Infrared And Nmr (1H And 13C) Spectral Studies Of N-(Substituted Phenyl)-Methanesulphonamides

    NASA Astrophysics Data System (ADS)

    Jayalakshmi, K. L.; Gowda, B. Thimme

    2004-08-01

    Twenty two N-(substituted phenyl)-methanesulphonamides of the general formula, CH3SO2NHR, where R = 4-XC6H4(X = H, CH3, F, Cl, Br or NO2), i-XC6H4(X=CH3, Cl orNO2 and i=2 or 3) and i, j-X2C6H3(i, j-X2 = 2,3-(CH3)2, 2,4-(CH3)2, 2,5-(CH3)2, 2,6-(CH3)2, 3,5-(CH3)2, 2,3-Cl2, 2,4- Cl2, 2,5-Cl2, 2,6-Cl2 or 3,4-Cl2) were prepared, characterized and their infrared spectra in the solid state and the NMR (1H and 13C) spectra in solution studied. The N-H stretching vibrations absorb in the range, 3298 - 3232 cm-1. Asymmetric and symmetric SO2 stretching vibrations appear as strong absorptions in the ranges, 1331 - 1317 cm-1 and 1157 - 1139 cm-1, respectively. The sulphonamides exhibit S-N stretching vibrations in the range, 926 - 833 cm-1. The effect of substitution in the phenyl ring in terms of electron withdrawing and electron donating groups is non-systematic. The 1H and 13C chemical shifts of N-(substituted phenyl)-methanesulphonamides are assigned to various protons and carbons of the compounds. Further, incremental shifts of the ring protons and carbons due to CH3SO2- and CH3SO2NH- groups in the N-(phenyl)-methanesulphonamide are computed and used to calculate the 1H and 13C chemical shifts of various protons and carbons of N-(substituted phenyl)-methanesulphonamides, by adding substituent contributions to the corresponding aromatic proton or carbon chemical shifts of either aniline, substituted anilines, benzene or substituted benzenes, in different ways, as per the principle of substituent addition. The computed values by different procedures agree well with each other and with the experimental chemical shifts. The correlation of these incremental shifts with the Hammett substituent parameters is poor.

  4. 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.

  5. An attempt to estimate ionic interactions with phenyl and pentafluorophenyl stationary phases in supercritical fluid chromatography.

    PubMed

    West, Caroline; Lemasson, Elise; Khater, Syame; Lesellier, Eric

    2015-09-18

    Pentafluorophenyl-bonded silica (PFP) phases employed in high-performance liquid chromatography (HPLC) often provide very different results depending on the column manufacturer. PFP phases also provide significantly different selectivity from non-fluorinated aromatic phases. As all HPLC columns can also be employed with carbon dioxide-based mobile phases, PFP phases can also be useful to supercritical fluid chromatography (SFC). However, whether they provide adequate retention and selectivity in SFC conditions is necessary for them to find applicability with this technique. In our laboratory, a column classification for packed column SFC was designed, based on the solvation parameter model, which currently comprises data for about eighty different columns. In this paper, we present the characterization of eleven PFP phases provided by different manufacturers used with carbon dioxide-methanol mobile phases. The columns are compared to fifteen other non-fluorinated phenyl and diphenyl phases in terms of their retention and separation characteristics assessed by the solvation parameter model with five Abraham descriptors. The latter is insufficient for an accurate description of retention mechanisms on the PFP phases, thus two extra terms accounting for ionic interactions with anions and cations (D(-) and D(+)), previously developed for HPLC in hydrophilic interaction mode (HILIC), are introduced. While some approximations are necessary regarding the true pH and pKa values in CO2-based mobile phases, the retention models are significantly improved by this addition, allowing to integrate ionizable analytes in the test set for evaluation of ionic interactions in the chromatographic systems. PMID:26278356

  6. 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

  7. 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.

  8. Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.

    PubMed

    Vargas, Angelo; Bonalumi, Norberto; Ferri, Davide; Baiker, Alfons

    2006-01-26

    The conformational analysis of the synthetic chiral modifier O-phenyl-cinchonidine (PhOCD) used in enantioselective hydrogenations over noble metal catalysts has been performed at a PM3 semiempirical level in vacuum. The minimum energy conformations calculated at the DFT level with a medium-size basis set have been compared to those of the parent alkaloid cinchonidine (CD). PhOCD behaves similarly to CD and shows four main conformers, denoted as Closed(1), Closed(2), Open(3), and Open(4). Open(3) is found to be the most stable in vacuum and in CH2Cl2 and CCl4 solvents. A comprehensive normal-mode analysis has been performed for these conformers, and assignment of the infrared spectrum of PhOCD in CCl4 (epsilon = 2.2) has been performed using the calculated spectrum of Open(3), which appears to be the most populated in this solvent. A combined theoretical-experimental VCD spectroscopy approach was used to increase the spectroscopic sensitivity toward changes in the distribution of conformers upon change of solvent polarity. The VCD spectra confirm that Open(3) is by far the most stable conformation in CCl4 (epsilon = 2.2) and indicate that an excess Closed(2) conformer has to be expected in CD2Cl2 (epsilon = 8.9). The possible influence of this conformational behavior is discussed on the basis of available catalytic data and in relation to the enantioselective potential of PhOCD as a chiral modifier on supported metal catalysts.

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

    PubMed Central

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

    2012-01-01

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

  10. Spin canting in the 3D anionic dicyanamide structure (SPh(3))Mn(dca)(3) (Ph = phenyl, dca = dicyanamide).

    PubMed

    Schlueter, John A; Manson, Jamie L; Hyzer, Kylee A; Geiser, Urs

    2004-07-12

    Through use of the SPh(3)(+) (Ph = phenyl, C(6)H(5)) cation as a molecular template, a new three-dimensional Mn(dca)(3)(-) [dca = dicyanamide, N(CN)(2)(-)] anionic structure has been crystallized. At room temperature, (SPh(3))Mn(dca)(3) (1) crystallizes in the monoclinic space group P2(1)/c, with a = 11.7079(5) A, b = 12.8554(5) A, c = 16.8605(6) A, beta = 100.666(2) degrees, and V = 2493.8(3) A(3). Magnetic susceptibility measurements indicate that this salt exhibits a spin canted long range antiferromagnetically ordered ground state below 2.5 K.

  11. (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

  12. 1-Formyl-3-phenyl-5-(4-isopropylphenyl)-2-pyrazoline: Synthesis, characterization, antimicrobial activity and DFT studies

    NASA Astrophysics Data System (ADS)

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

    2016-10-01

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

  13. 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

  14. 3-(2-Ethyl-2-phenyl­hydrazin-1-yl­idene)indolin-2-one

    PubMed Central

    Ashiq, Uzma; Jamal, Rifat Ara; Ismail, Hina; Khan, Khalid Mohammed; Yousuf, Sammer

    2012-01-01

    In the title compound, C16H15N3O, the dihedral angle between the indole ring system (r.m.s. deviation = 0.020 Å) and the phenyl ring is 14.49 (9)°. The mol­ecular conformation is supported by an intra­molecular C—H⋯O inter­action, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops. PMID:23476282

  15. Beryllium derivatives of a phenyl-substituted β-diketiminate: a well-defined ring opening reaction of tetrahydrofuran.

    PubMed

    Arrowsmith, Merle; Crimmin, Mark R; Hill, Michael S; Kociok-Köhn, Gabriele

    2013-07-14

    The phenyl-substituted β-diketiminate ligand precursor (Ph)LH, [(Dipp)NC(Ph)CHC(Ph)NH(Dipp)] (Dipp = 2,6-di-isopropylphenyl) and its lithium and beryllium halide derivatives [(Ph)LLi(OEt2)], [(Ph)LBeCl] and [(Ph)LBeI] have been synthesised and characterised by NMR and X-ray structural analysis. The iodoberyllium complex [(Ph)LBeI] reacts with THF in a well-defined ring-opening insertion reaction to form the 4-iodo-n-butoxide complex [(Ph)LBeO(CH2)4I].

  16. 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

  17. Crystal structure of 4,4-dibutyl-2-phenyl-3,4-di­hydro­quinazoline

    PubMed Central

    El-Hiti, Gamal A.; Smith, Keith; Hegazy, Amany S.; Alshammari, Mohammed B.; Kariuki, Benson M.

    2014-01-01

    In the title compound, C22H28N2, the dihedral angle between the planes of the phenyl ring and the di­hydro­quinazoline ring system (r.m.s. deviation = 0.030 Å) is 24.95 (7)° and both n-butane chains assume all-trans conformations. In the crystal, N—H⋯N hydrogen bonds link the mol­ecules into C(4) chains propagating in the [001] direction. PMID:25484693

  18. 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

  19. 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

  20. 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.

  1. Design, Synthesis, and Biological Evaluation of New 2-Phenyl-4H-chromen-4-one Derivatives as Selective Cyclooxygenase-2 Inhibitors

    PubMed Central

    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 (Arg513, Val523, and His90) and the carbonyl group of the chromene ring could interact with Ser530. 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

  2. TFP5 prevents 1-methyl-4-phenyl pyridine ion-induced neurotoxicity in mouse cortical neurons

    PubMed Central

    Zhang, Qi-Shan; Liao, Yuan-Gao; Ji, Zhong; Gu, Yong; Jiang, Hai-Shan; Xie, Zuo-Shan; Pan, Su-Yue; Hu, Ya-Fang

    2016-01-01

    The present study aimed to investigate the protective effect of a modified p5 peptide, TFP5, on 1-methyl-4-phenyl pyridine ion (MPP+)-induced neurotoxicity in cortical neurons and explore the therapeutic effect of TFP5 on Parkinson's disease (PD). MPP+ was applied to a primary culture of mouse cortical neurons to establish the cell model of PD. Neurons were divided into four groups: Control, model (MPP+), scrambled peptide (Scb) (Scb + MPP+) and TFP5 (TFP5 + MPP+) groups. Pretreatment with Scb or TFP5 was applied to the latter two groups, respectively, for 3 h, while phosphate-buffered saline was applied to the control and model groups. MPP+ was then applied to all groups, with the exception of the control group, and neurons were cultured for an additional 24 h. Neuron viability was evaluated using a Cell Counting kit-8 (CCK8) assay. To explore the mechanism underlying the protective effects of TFP5, the expression levels of p35, p25 and phosphorylated myocyte enhancer factor 2 (p-MEF2D) were determined by western blotting. Fluorescence microscopy showed that TFP5 was able to pass through cell membranes and distribute around the nucleus. CCK8 assay showed that neuronal apoptosis was dependent on MPP+ concentration and exposure time. Cell viability decreased significantly in the model group compared with the control group (55±7 vs. 100±0%; P<0.01), and increased significantly in the TFP5 group compared with the model group (98±2 vs. 55±5%; P<0.01) and Scb group (98±2 vs. 54±4%; P<0.01). Scb exhibited no protective effect. Western blotting results showed that MPP+ induced p25 and p-MEF2D expression, TFP5 and Scb did not affect MPP+-induced p25 expression, but TFP5 reduced MPP+-induced p-MEF2D expression. In summary, TFP5 protects against MPP+-induced neurotoxicity in mouse cortical neurons, possibly through inhibiting the MPP+-induced formation and elevated kinase activity of a cyclin-dependent kinase 5/p25 complex.

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

    NASA Astrophysics Data System (ADS)

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

    2013-06-01

    New tetranitrosyl binuclear iron complex [Fe2(SС7H5N4)2(NO)4] (I) has been synthesized by interaction of aqueous solutions of anionic salts [Fе(S2O3)2(NO)2]3- and [SС7H5N4]-. The latter one was synthesized by reduction of bis-(1-phenyl-1H-tetrazole-5-yl) disulfide with hydrazine hydrate in ethanol at T = 25 °C. Molecular and crystalline structure of I was determined by X-ray analysis; the complex has binuclear structure of "μ-SCN" type with ˜4.02 Å between the iron atoms. Shortened О⋯О contacts (2.81 Å) between the NO groups of similar type are observed. Parameters of Mössbauer spectrum for I are: isomer shift δFe = 0.311(1) mm/s, quadrupole splitting ΔEQ = 1.044(1) mm/s, line width Γ = 0.267(1) mm/s at 85 K. From SQUID magnetometry data, the temperature and field dependences of the magnetic moment of I are well described in the frame of a simple model of binuclear iron complex with magnetic centers S1 = S2 = ½. In solution, binuclear structure of the complex remains, though the NO groups are non-equivalent. For solutions of I five-line hyperfine structure of spectrum (HFS) is observed, g-factor = 2.03. For polycrystals of I, no HFS was observed due to averaged exchange interaction between the electron spins of adjacent complexes. In polycrystals of I, the number of spins per one binuclear complex is <2, this being the evidence of antiferromagnetic exchange interaction of unpaired electrons of two iron atoms. The average number of spins in crystals (0.65) and solutions (0.55) are close. The maximum amount of NO generated by I in 1% dimethylsulfoxide (DMSO) aqueous solution is ˜13.8 nM, it halves in 8 min after decomposition starts, and reaches ˜3.8 nM in anaerobic conditions at Т = 25 °С, pH 7.0. This is due, according to quantum-chemical calculations, to the presence of a more stable Fesbnd NO bond in I than in its isostructural analog - nitrosyl iron complex with 1-methyltetrazole-5-yl (II).

  4. 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

    2016-03-28

    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) (1), [Cu(OCOPh)2L] (2), [Cu(o-OCOC6H4OH)2L] (3), [Cu(m-OCOC6H4OH)2L]4·MeOH (·MeOH) and [Cu(p-OCOC6H4OH)2L]5·2H2O (·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 2-5, are highly distorted as a result of the chelating-bidentate mode of one of the carboxylate ligands. Intermolecular π···π stacking interactions could also be found in 2-5 (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 1 and 4) and to an infinite 2D network (in 5). Compounds 1 and 4 show high in vitro cytotoxicity towards HCT116 colorectal carcinoma and HepG2 hepatocellular carcinoma cell lines. The antiproliferative potential of compound 1 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 1, 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.

  5. TFP5 prevents 1-methyl-4-phenyl pyridine ion-induced neurotoxicity in mouse cortical neurons

    PubMed Central

    Zhang, Qi-Shan; Liao, Yuan-Gao; Ji, Zhong; Gu, Yong; Jiang, Hai-Shan; Xie, Zuo-Shan; Pan, Su-Yue; Hu, Ya-Fang

    2016-01-01

    The present study aimed to investigate the protective effect of a modified p5 peptide, TFP5, on 1-methyl-4-phenyl pyridine ion (MPP+)-induced neurotoxicity in cortical neurons and explore the therapeutic effect of TFP5 on Parkinson's disease (PD). MPP+ was applied to a primary culture of mouse cortical neurons to establish the cell model of PD. Neurons were divided into four groups: Control, model (MPP+), scrambled peptide (Scb) (Scb + MPP+) and TFP5 (TFP5 + MPP+) groups. Pretreatment with Scb or TFP5 was applied to the latter two groups, respectively, for 3 h, while phosphate-buffered saline was applied to the control and model groups. MPP+ was then applied to all groups, with the exception of the control group, and neurons were cultured for an additional 24 h. Neuron viability was evaluated using a Cell Counting kit-8 (CCK8) assay. To explore the mechanism underlying the protective effects of TFP5, the expression levels of p35, p25 and phosphorylated myocyte enhancer factor 2 (p-MEF2D) were determined by western blotting. Fluorescence microscopy showed that TFP5 was able to pass through cell membranes and distribute around the nucleus. CCK8 assay showed that neuronal apoptosis was dependent on MPP+ concentration and exposure time. Cell viability decreased significantly in the model group compared with the control group (55±7 vs. 100±0%; P<0.01), and increased significantly in the TFP5 group compared with the model group (98±2 vs. 55±5%; P<0.01) and Scb group (98±2 vs. 54±4%; P<0.01). Scb exhibited no protective effect. Western blotting results showed that MPP+ induced p25 and p-MEF2D expression, TFP5 and Scb did not affect MPP+-induced p25 expression, but TFP5 reduced MPP+-induced p-MEF2D expression. In summary, TFP5 protects against MPP+-induced neurotoxicity in mouse cortical neurons, possibly through inhibiting the MPP+-induced formation and elevated kinase activity of a cyclin-dependent kinase 5/p25 complex. PMID:27698762

  6. 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.

  7. 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

  8. 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.

  9. 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.

  10. 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.

  11. Important role of molecular packing and intermolecular interactions in two polymorphs of (Z)-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile. Preparation, structures, and optical properties

    NASA Astrophysics Data System (ADS)

    Percino, M. Judith; Cerón, Margarita; Ceballos, Paulina; Soriano-Moro, Guillermo; Castro, M. Eugenia; Chapela, Víctor M.; Bonilla-Cruz, José; Reyes-Reyes, Marisol; López-Sandoval, Román; Siegler, Maxime A.

    2014-12-01

    The novel compound Z-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile (PPyPAN) was synthesized from the condensation reaction between phenylacetonitrile and 4-(pyridin-2-yl)benzaldehyde. This compound crystallizes in two forms: polymorph I (triclinic, P - 1, Z‧ = 2) and polymorph II (orthorhombic, Pbc21, Z‧ = 2). The molecular structures and optical properties of the two polymorphs have been characterized via1H NMR, EI, FTIR, UV-Vis spectroscopy, DSC, single-crystal and XRPD. The molecular structure, packing properties, and intermolecular interactions were examined for both polymorphs of PPyPAN in order to interpret the emission properties. A subtle change in the molecular conformation (e.g., a rotation around single Csbnd C bonds) found for both polymorph plays an important role in their solid-state properties. The structure and optical properties of the new structures were well characterized and showed unique features for both polymorphic phases. For phase I, we observed an excitation spectrum with an λex at 325-346 nm, which is the maximum excitation or absorption wavelength for the lowest So → S1 transition, which is characteristic to the π-π* transition, and an emission spectrum with an λemmax at 454 nm. For phase II, the excitation spectrum showed an λexmax at 325 nm, whereas the λemmax showed a red-shift to 492 nm.

  12. 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

  13. 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.

  14. Assessing Cholesterol Storage in Live Cells and C. elegans by Stimulated Raman Scattering Imaging of Phenyl-Diyne Cholesterol

    NASA Astrophysics Data System (ADS)

    Lee, Hyeon Jeong; Zhang, Wandi; Zhang, Delong; Yang, Yang; Liu, Bin; Barker, Eric L.; Buhman, Kimberly K.; Slipchenko, Lyudmila V.; Dai, Mingji; Cheng, Ji-Xin

    2015-01-01

    We report a cholesterol imaging method using rationally synthesized phenyl-diyne cholesterol (PhDY-Chol) and stimulated Raman scattering (SRS) microscope. The phenyl-diyne group is biologically inert and provides a Raman scattering cross section that is 88 times larger than the endogenous C = O stretching mode. SRS microscopy offers an imaging speed that is faster than spontaneous Raman microscopy by three orders of magnitude, and a detection sensitivity of 31 μM PhDY-Chol (~1,800 molecules in the excitation volume). Inside living CHO cells, PhDY-Chol mimics the behavior of cholesterol, including membrane incorporation and esterification. In a cellular model of Niemann-Pick type C disease, PhDY-Chol reflects the lysosomal accumulation of cholesterol, and shows relocation to lipid droplets after HPβCD treatment. In live C. elegans, PhDY-Chol mimics cholesterol uptake by intestinal cells and reflects cholesterol storage. Together, our work demonstrates an enabling platform for study of cholesterol storage and trafficking in living cells and vital organisms.

  15. Assessing Cholesterol Storage in Live Cells and C. elegans by Stimulated Raman Scattering Imaging of Phenyl-Diyne Cholesterol

    PubMed Central

    Lee, Hyeon Jeong; Zhang, Wandi; Zhang, Delong; Yang, Yang; Liu, Bin; Barker, Eric L.; Buhman, Kimberly K.; Slipchenko, Lyudmila V.; Dai, Mingji; Cheng, Ji-Xin

    2015-01-01

    We report a cholesterol imaging method using rationally synthesized phenyl-diyne cholesterol (PhDY-Chol) and stimulated Raman scattering (SRS) microscope. The phenyl-diyne group is biologically inert and provides a Raman scattering cross section that is 88 times larger than the endogenous C = O stretching mode. SRS microscopy offers an imaging speed that is faster than spontaneous Raman microscopy by three orders of magnitude, and a detection sensitivity of 31 μM PhDY-Chol (~1,800 molecules in the excitation volume). Inside living CHO cells, PhDY-Chol mimics the behavior of cholesterol, including membrane incorporation and esterification. In a cellular model of Niemann-Pick type C disease, PhDY-Chol reflects the lysosomal accumulation of cholesterol, and shows relocation to lipid droplets after HPβCD treatment. In live C. elegans, PhDY-Chol mimics cholesterol uptake by intestinal cells and reflects cholesterol storage. Together, our work demonstrates an enabling platform for study of cholesterol storage and trafficking in living cells and vital organisms. PMID:25608867

  16. Synthesis and bioevaluation of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acids as potent xanthine oxidase inhibitors.

    PubMed

    Guan, Qi; Cheng, Zengjin; Ma, Xiaoxue; Wang, Lijie; Feng, Dongjie; Cui, Yuanhang; Bao, Kai; Wu, Lan; Zhang, Weige

    2014-10-01

    A series of 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acid derivatives (8a-f, 9a-m) were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Structure-activity relationship analyses have also been presented. Most of the target compounds exhibited potency levels in the nanomolar range. Compound 9e emerged as the most potent xanthine oxidase inhibitor (IC50 = 5.5 nM) in comparison to febuxostat (IC50 = 18.6 nM). Steady-state kinetics measurements with the bovine milk enzyme indicated a mixed type inhibition with Ki and Ki' values of 0.9 and 2.3 nM, respectively. A molecular modeling study on compounds 9e was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 2-phenyl-4-methyl-1,3-selenazole-5-carboxylic acid scaffold.

  17. Crystal structure of 5-tert-but­yl-10,15,20-tri­phenyl­porphyrin

    PubMed Central

    Flanagan, Keith J.; Mothi, Ebrahim Mohamed; Kötzner, Lisa; Senge, Mathias O.

    2016-01-01

    In the title free base porphyrin, C42H34N4, the neighbouring N⋯N distances in the center of the ring vary from 2.818 (8) to 2.998 (8) Å and the phenyl rings are tilted from the 24-atom mean plane at angles varying between 62.42 (2)–71.63 (2)°. The NH groups are involved in intra­molecular bifurcated N—H⋯(N,N) hydrogen bonds. The Ca—Cm—Ca angles vary slightly for the phenyl rings, between 124.19 (18)–126.17 (18)°. The largest deviation from the mean plane of the 24-atom macrocycle is associated with the meso carbon at the substituted tert-butyl position, which is displaced from the mean plane by 0.44 (2) Å. The free base porphyrin is characterized by a significant degree of ruffled (B 1u) distortion with contributions from domed (A 2u) and wave [Eg(y) and Eg(x)] modes. In the crystal, mol­ecules are linked by a number of weak C—H⋯π inter­actions, forming a three-dimensional framework. The structure was refined as a two-component inversion twin. PMID:26958370

  18. Vibrational assignment, structure and intramolecular hydrogen bond study of 3-amino-1-phenyl-2-buten-1-one.

    PubMed

    Raissi, Haidar; Yarali, Atieh; Farzad, Farzaneh; Nowroozi, Alireza

    2006-03-01

    Fourier transform infrared and Fourier transform Raman spectra of 3-amino-1-phenyl-2-buten-1-one and its deuterated analogue were recorded in the regions 400-4,000 and 150-4,000 cm(-1), respectively. Furthermore, the molecular structure and vibrational frequencies of title compound were investigated by a series of density functional theoretical, DFT, and ab initio calculations at the post-Hartree-Fock (MP2) level. Although, the calculated frequencies are generally in agreement with the observed spectra but the DFT results are in much better quantitative agreement with the observed spectra than the MP2 results. The observed wavenumbers were analyzed and assigned to different normal modes of vibration of the molecule. The calculated geometrical parameters show a strong intramolecular hydrogen bond with a N...O distance of 2.621-2.668 A. This bond length is shorter than that of its parent, 4-amino-3-penten-2-one (with two methyl groups in the beta-position), which is in agreement with spectroscopic results. The topological properties of the electron density contributions for intramolecular hydrogen bond in 3-amino-1-phenyl-2-buten-1-one and 4-amino-3-penten-2-one have been analyzed in term of the Bader theory of atoms in molecules (AIM). These results also support the stronger hydrogen bond in the title compound with respect to the parent molecule.

  19. Copper(II) and nickel(II) complexes of benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone: Synthesis, characterization and biological activity

    NASA Astrophysics Data System (ADS)

    Prathima, B.; Subba Rao, Y.; Adinarayana Reddy, S.; Reddy, Y. P.; Varada Reddy, A.

    2010-09-01

    Benzyloxybenzaldehyde-4-phenyl-3-thiosemicarbazone ligand (L) has been synthesized from benzyloxybenzaldehyde and 4-phenyl-3-thiosemicarbazide. Complexes of this ligand with chlorides of Cu(II) and Ni(II) have been prepared. The structure of the ligand (L) is proposed based on elemental analysis, IR and 1H NMR spectra. Its complexes with Cu(II) and Ni(II) ions are characterized from the studies of electronic as well as EPR spectra. On the basis of electronic and EPR studies, rhombically distorted octahedral structure has been proposed for Cu(II) complex while the Ni(II) complex has been found to acquire an octahedral structure. The ligand and their metal complexes have been tested in vitro for their biological effects. Their antibacterial activities against Gram-negative bacteria ( Escherichia coli and Klebsiella pneumoniae) and Gram-positive bacteria ( Staphylococcus aureus and Bacillus subtilis) have been investigated. The prepared metal complexes exhibit higher antibacterial activities than the parent ligand. The in vitro antioxidant activity of free ligand and its metal(II) complexes have also been investigated and the results however reveal that the ligand exhibits greater antioxidant activity than its complexes.

  20. A new high phenyl lactic acid-yielding Lactobacillus plantarum IMAU10124 and a comparative analysis of lactate dehydrogenase gene.

    PubMed

    Zhang, Xiqing; Zhang, Shuli; Shi, Yan; Shen, Fadi; Wang, Haikuan

    2014-07-01

    Phenyl lactic acid (PLA) has been widely reported as a new natural antimicrobial compound. In this study, 120 Lactobacillus plantarum strains were demonstrated to produce PLA using high-performance liquid chromatography. Lactobacillus plantarum IMAU10124 was screened with a PLA yield of 0.229 g L(-1) . Compared with all previous reports, this is the highest PLA-producing lactic acid bacteria (LAB) when grown in MRS broth without any optimizing conditions. When 3.0 g L(-1) phenyl pyruvic acid (PPA) was added to the medium as substrate, PLA production reached 2.90 g L(-1) , with the highest 96.05% conversion rate. A lowest PLA-yielding L. plantarum IMAU40105 (0.043 g L(-1) ) was also screened. It was shown that the conversion from PPA to PLA by lactic dehydrogenase (LDH) is the key factor in the improvement of PLA production by LAB. Comparing the LDH gene of two strains, four amino acid mutation sites were found in this study in the LDH of L. plantarum IMAU10124.

  1. Efficient biocatalytic synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by a newly isolated Trichoderma asperellum ZJPH0810 using dual cosubstrate: ethanol and glycerol.

    PubMed

    Li, Jun; Wang, Pu; He, Jun-Yao; Huang, Jin; Tang, Jun

    2013-08-01

    (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol is a crucial intermediate for the synthesis of Aprepitant. An efficient biocatalytic process for (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol was developed via the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone, catalyzed by whole cells of newly isolated Trichoderma asperellum ZJPH0810 using ethanol and glycerol as dual cosubstrate for cofactor recycling. A fungal strain ZJPH0810, showing asymmetric biocatalytic activity of 3,5-bis(trifluoromethyl) acetophenone to its corresponding (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, was isolated from a soil sample. Based on its morphological and physiological characteristics and internal transcribed spacer sequence, this isolate was identified as T. asperellum ZJPH0810, which afforded an NADH-dependent (R)-stereospecific carbonyl reductase and was a promising biocatalyst for the synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol. Some key reaction parameters involved in the bioreduction catalyzed by T. asperellum ZJPH0810 were subsequently optimized. The effectiveness of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol production was significantly enhanced by employing a novel dual cosubstrate-coupled system for cofactor recycling. The established efficient bioreduction system contained 50 mM of 3,5-bis(trifluoromethyl) acetophenone and 60 g l(-1) of resting cells, employing ethanol (6.0 %, v/v) and glycerol (0.5 %, v/v) as dual cosubstrate. The bioreduction was performed in distilled water medium, at 30 °C and 200 rpm. Under the above conditions, a best yield of 93.4 % was obtained, which is nearly a 3.5-fold increase in contrast to no addition of cosubstrate. The ee value of the product reached above 98 %. This biocatalytic process shows great potential in the production of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, a valuable chiral building block in the pharmaceutical industry.

  2. Crystal structure of (E)-1-(2-nitro­benzyl­idene)-2,2-di­phenyl­hydrazine

    PubMed Central

    Flores-Alamo, Marcos; Meléndrez-Luévano, Ruth; Ortiz Márquez, José A.; Sansinenea Royano, Estibaliz; Cabrera-Vivas, Blanca M.

    2014-01-01

    The title compound, C19H15N3O2, shows an E conformation of the imine bond. The dihedral angle between the planes of the phenyl rings in the di­phenyl­hydrazine groups is 88.52 (4)°. The 2-nitro­benzene ring shows a torsion angle of 10.17 (8)° with the C=N—N plane. A short intra­molecular C—H⋯O contact occurs. In the crystal, only van der Waals contacts occur between the mol­ecules. PMID:25309247

  3. Intramolecular general acid catalysis of the hydrolysis of 2-(2'-imidazolium)phenyl phosphate, and bond length-reactivity correlations for reactions of phosphate monoester monoanions.

    PubMed

    Brandão, Tiago A S; Orth, Elisa S; Rocha, Willian R; Bortoluzzi, Adailton J; Bunton, Clifford A; Nome, Faruk

    2007-05-11

    Rate constants for the hydrolysis of 2-(2'-imidazolium)phenyl hydrogen phosphate (IMPP) in water at pH<6 indicate that activation by the imidazolium moiety disappears with the deprotonation of the phosphate group, and the reaction involves the hydrogen-bonding of the imidazolium NH with the aryl oxygen leaving group. The reaction should involve a near-planar conformation of the imidazolium and the phenyl groups in the activated complex, which favors proton-transfer. The crystal structure of IMPP was solved, and a bond length-reactivity correlation for reactions of phosphate monoester monoanions is described.

  4. The synthesis of rigid polycyclic structures for the study of diatropic or steric effects of a phenyl ring on CF bond.

    PubMed

    Chang, Yung-Yu; Ho, I-Ting; Ho, Tse-Lok; Chung, Wen-Sheng

    2013-12-20

    Polycyclic compounds 1a-c were synthesized to study the diatropic effects of a flanking phenyl ring on nearby CH and CF bonds. (19)F NMR spectra of 1b and 1c were strongly deshielded compared with those of the ring-opened compounds 3b, 7b, and 7c. DMol3 calculations on 1a-c provided quantitative bond lengths and torsional angles to support the conclusion that the downfield shifts in the (19)F NMR spectra are mainly due to steric interactions between the CF bonds and the π clouds of the phenyl ring(s).

  5. Thermal Studies of Zn(II), Cd(II) and Hg(II) Complexes of Some N-Alkyl-N-Phenyl-Dithiocarbamates

    PubMed Central

    Onwudiwe, Damian C.; Ajibade, Peter A.

    2012-01-01

    The thermal decomposition of Zn(II), Cd(II) and Hg(II) complexes of N-ethyl-N-phenyl and N-butyl-N-phenyl dithiocarbamates have been studied using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The products of the decomposition, at two different temperatures, were further characterized by scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDX). The results show that while the zinc and cadmium complexes undergo decomposition to form metal sulphides, and further undergo oxidation forming metal oxides as final products, the mercury complexes gave unstable volatiles as the final product. PMID:22949811

  6. meso-(4-(N,N-dialkylamino)phenyl)-substituted subporphyrins: remarkably perturbed absorption spectra and enhanced fluorescence by intramolecular charge transfer interactions.

    PubMed

    Inokuma, Yasuhide; Easwaramoorthi, Shanmugam; Yoon, Zin Seok; Kim, Dongho; Osuka, Atsuhiro

    2008-09-17

    A series of meso-(4-(N,N-dibenzylamino)phenyl)-substituted subporphyrins was synthesized by means of Buchwald-Hartwig amination protocol. Substitution of the amino group at the 4-position of the meso-phenyl substituent resulted in a remarkable red shift in the absorption spectra and drastic enhancement of fluorescence intensity probably as a consequence of intramolecular CT interaction. These characteristics have been utilized to construct a cation-sensing system by appending a 1-aza-15-crown-5 unit to subporphyrin that displays large spectral changes upon cation binding.

  7. Optimization of Phenyl-Substituted Benzimidazole Carboxamide Poly(ADP-Ribose) Polymerase Inhibitors: Identification of (S)-2-(2-Fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (A-966492), a Highly Potent and Efficacious Inhibitor

    SciTech Connect

    Penning, Thomas D.; Zhu, Gui-Dong; Gong, Jianchun; Thomas, Sheela; Gandhi, Viraj B.; Liu, Xuesong; Shi, Yan; Klinghofer, Vered; Johnson, Eric F.; Park, Chang H.; Fry, Elizabeth H.; Donawho, Cherrie K.; Frost, David J.; Buchanan, Fritz G.; Bukofzer, Gail T.; Rodriguez, Luis E.; Bontcheva-Diaz, Velitchka; Bouska, Jennifer J.; Osterling, Donald J.; Olson, Amanda M.; Marsh, Kennan C.; Luo, Yan; Giranda, Vincent L.

    2010-06-21

    We have developed a series of phenylpyrrolidine- and phenylpiperidine-substituted benzimidazole carboxamide poly(ADP-ribose) polymerase (PARP) inhibitors with excellent PARP enzyme potency as well as single-digit nanomolar cellular potency. These efforts led to the identification of (S)-2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (22b, A-966492). Compound 22b displayed excellent potency against the PARP-1 enzyme with a K{sub i} of 1 nM and an EC{sub 50} of 1 nM in a whole cell assay. In addition, 22b is orally bioavailable across multiple species, crosses the blood-brain barrier, and appears to distribute into tumor tissue. It also demonstrated good in vivo efficacy in a B16F10 subcutaneous murine melanoma model in combination with temozolomide and in an MX-1 breast cancer xenograft model both as a single agent and in combination with carboplatin.

  8. Discovery and structural optimization of 1-phenyl-3-(1-phenylethyl)urea derivatives as novel inhibitors of CRAC channel

    PubMed Central

    Zhang, Hai-zhen; Xu, Xiao-lan; Chen, Hua-yan; Ali, Sher; Wang, Dan; Yu, Jun-wei; Xu, Tao; Nan, Fa-jun

    2015-01-01

    Aim: Ca2+-release-activated Ca2+ (CRAC) channel, a subfamily of store-operated channels, is formed by calcium release-activated calcium modulator 1 (ORAI1), and gated by stromal interaction molecule 1 (STIM1). CRAC channel may be a novel target for the treatment of immune disorders and allergy. The aim of this study was to identify novel small molecule CRAC channel inhibitors. Methods: HEK293 cells stably co-expressing both ORAI1 and STIM1 were used for high-throughput screening. A hit, 1-phenyl-3-(1-phenylethyl)urea, was identified that inhibited CRAC channels by targeting ORAI1. Five series of its derivatives were designed and synthesized, and their primary structure-activity relationships (SARs) were analyzed. All derivatives were assessed for their effects on Ca2+ influx through CRAC channels on HEK293 cells, cytotoxicity in Jurkat cells, and IL-2 production in Jurkat cells expressing ORAI1-SS-eGFP. Results: A total of 19 hits were discovered in libraries containing 32 000 compounds using the high-throughput screening. 1-Phenyl-3-(1-phenylethyl)urea inhibited Ca2+ influx with IC50 of 3.25±0.17 μmol/L. SAR study on its derivatives showed that the alkyl substituent on the α-position of the left-side benzylic amine (R1) was essential for Ca2+ influx inhibition and that the S-configuration was better than the R-configuration. The derivatives in which the right-side R3 was substituted by an electron-donating group showed more potent inhibitory activity than those that were substituted by electron-withdrawing groups. Furthermore, the free N–H of urea was not necessary to maintain the high potency of Ca2+ influx inhibition. The N,N′-disubstituted or N′-substituted derivatives showed relatively low cytotoxicity but maintained the ability to inhibit IL-2 production. Among them, compound 5b showed an improved inhibition of IL-2 production and low cytotoxicity. Conclusion: 1-Phenyl-3-(1-phenylethyl)urea is a novel CRAC channel inhibitor that specifically targets

  9. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the labeling...-benzenetriol. (a) Identity. The color additive2- phenyl]azo]-1,3,5-benzenetriol is formed in situ in...

  10. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the labeling...-benzenetriol. (a) Identity. The color additive2- phenyl]azo]-1,3,5-benzenetriol is formed in situ in...

  11. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the labeling...-benzenetriol. (a) Identity. The color additive2- phenyl]azo]-1,3,5-benzenetriol is formed in situ in...

  12. Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant.

    PubMed

    Shen, Rong; Kusakabe, Taichi; Yatsu, Tomofumi; Kanno, Yuichiro; Takahashi, Keisuke; Nemoto, Kiyomitsu; Kato, Keisuke

    2016-01-01

    An efficient Pd(II)/Pd⁰-p-benzoquinone/hydroquinone-CuCl₂/CuCl catalyst system was developed that uses environmentally friendly molecular oxygen as the terminal oxidant to catalyze the cyclization-carbonylation-cyclization coupling reaction (CCC-coupling reaction) of (o-alkynyl phenyl) (methoxymethyl) sulfides. PMID:27607997

  13. 21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 1 2013-04-01 2013-04-01 false 4- -2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical Devices § 73.3122 4-...

  14. 21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 1 2012-04-01 2012-04-01 false 4- -2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical Devices § 73.3122 4-...

  15. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substance identified as...

  16. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substance identified as...

  17. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1800 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol. (a) Chemical substances and significant new uses subject to reporting. (1) The chemical substance identified as...

  18. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... C8-10-branched alkyl) derivs. 721.10022 Section 721.10022 Protection of Environment ENVIRONMENTAL...-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  19. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... C8-10-branched alkyl) derivs. 721.10022 Section 721.10022 Protection of Environment ENVIRONMENTAL...-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  20. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-rich C88-10-branched alkyl) derivs. 721.10023 Section 721.10023 Protection of Environment ENVIRONMENTAL...-10-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  1. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... C8-10-branched alkyl) derivs. 721.10022 Section 721.10022 Protection of Environment ENVIRONMENTAL...-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  2. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-rich C88-10-branched alkyl) derivs. 721.10023 Section 721.10023 Protection of Environment ENVIRONMENTAL...-10-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

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

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... C8-10-branched alkyl) derivs. 721.10022 Section 721.10022 Protection of Environment ENVIRONMENTAL...-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  4. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-rich C8-10-branched alkyl) derivs. 721.10023 Section 721.10023 Protection of Environment ENVIRONMENTAL...-10-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-rich C8-10-branched alkyl) derivs. 721.10023 Section 721.10023 Protection of Environment ENVIRONMENTAL...-10-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

  6. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-rich C8-10-branched alkyl) derivs. 721.10023 Section 721.10023 Protection of Environment ENVIRONMENTAL...-10-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar,ar′-(C9-rich C8-10-branched...

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... C8-10-branched alkyl) derivs. 721.10022 Section 721.10022 Protection of Environment ENVIRONMENTAL...-branched alkyl) derivs. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN...

  8. Rhodium(III)-catalyzed cyanation of vinylic C-H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent.

    PubMed

    Su, Wei; Gong, Tian-Jun; Xiao, Bin; Fu, Yao

    2015-07-28

    Rh(III)-catalyzed direct vinylic C-H cyanation reaction has been developed as a practical method for the synthesis of alkenyl nitriles. N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS), a user-friendly cyanation reagent, was used in the transformation. Both acrylamides and ketoximes can be employed in the new C-H cyanation process. PMID:26108194

  9. 21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 1 2010-04-01 2010-04-01 false 4- -2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical Devices § 73.3122 4-...

  10. 6-Allyl-8-meth­oxy-3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine

    PubMed Central

    Zhu, Jing; Ren, Zhi-Dong; Liu, Yang; Zhao, Lei; Wu, Yong

    2011-01-01

    In the title compound, C18H19NO2, the allyl group is disordered over two sets of sites [occupancy ratio 0.662 (4):0.338 (4)]. The dihedral angle between the phenyl and benzene rings is 87.44 (10)°. The oxazinane ring adopts a sofa conformation. PMID:22091082

  11. 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, 2010 CFR

    2010-07-01

    ...]amino]-4-(oxo-.kappa.O)-5-pyrimidinyl]azo-.kappaN1]-4-hydroxy-.kappa.O)-5-nitrobenzenesulfonato(3... substance identified as chromate(3-), bis phenyl]sulfonyl]amino]-4-(oxo-.kappa.O)-5-pyrimidinyl]azo-.kappaN1... Significant New Uses for Specific Chemical Substances § 721.8950 Chromate(3-), bis...

  12. Fast Hetero-Diels-Alder Reactions Using 4-Phenyl-1,2,4-Triazoline-3,5-Dione (PTAD) as the Dienophile

    ERIC Educational Resources Information Center

    Celius, Tevye C.

    2010-01-01

    A hetero-Diels-Alder reaction that proceeds rapidly and only requires a simple filtration to purify the product is presented. The dienophile, 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), is prepared by the heterogeneous oxidation of 4-phenylurazole by the bromenium ion, Br[superscript +], generated in situ by the oxidation of potassium bromide by…

  13. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  14. 21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2- phenyl]azo]-1,3,5-benzenetriol may be safely used to mark soft (hydrophilic) contact lenses with the letter R or the letter L for... exceed 1.1×10−7 grams in a soft (hydrophilic) contact lens. (2) When used as specified in the...

  15. Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant.

    PubMed

    Shen, Rong; Kusakabe, Taichi; Yatsu, Tomofumi; Kanno, Yuichiro; Takahashi, Keisuke; Nemoto, Kiyomitsu; Kato, Keisuke

    2016-09-05

    An efficient Pd(II)/Pd⁰-p-benzoquinone/hydroquinone-CuCl₂/CuCl catalyst system was developed that uses environmentally friendly molecular oxygen as the terminal oxidant to catalyze the cyclization-carbonylation-cyclization coupling reaction (CCC-coupling reaction) of (o-alkynyl phenyl) (methoxymethyl) sulfides.

  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, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Carbon black, 4- phenyl-modified, hydrochlorides (generic). 721.10080 Section 721.10080 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  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, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Carbon black, 4- phenyl-modified, hydrochlorides (generic). 721.10080 Section 721.10080 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  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, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Carbon black, 4- phenyl-modified, hydrochlorides (generic). 721.10080 Section 721.10080 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  19. 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, hydrochlorides (generic). 721.10080 Section 721.10080 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances...

  20. Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases.

    PubMed

    Cao, Li; Lee, Jintae; Chen, Wilfred; Wood, Thomas K

    2006-06-20

    Soluble epoxide hydrolase (EH) from the potato Solanum tuberosum and an evolved EH of the bacterium Agrobacterium radiobacter AD1, EchA-I219F, were purified for the enantioconvergent hydrolysis of racemic styrene oxide into the single product (R)-1-phenyl-1,2-ethanediol, which is an important intermediate for pharmaceuticals. EchA-I219F has enhanced enantioselectivity (enantiomeric ratio of 91 based on products) for converting (R)-styrene oxide to (R)-1-phenyl-1,2-ethanediol (2.0 +/- 0.2 micromol/min/mg), and the potato EH converts (S)-styrene oxide primarily to the same enantiomer, (R)-1-phenyl-1,2-ethanediol (22 +/- 1 micromol/min/mg), with an enantiomeric ratio of 40 +/- 17 (based on substrates). By mixing these two purified enzymes, inexpensive racemic styrene oxide (5 mM) was converted at 100% yield to 98% enantiomeric excess (R)-1-phenyl-1,2-ethanediol at 4.7 +/- 0.7 micromol/min/mg. Hence, at least 99% of substrate is converted into a single stereospecific product at a rapid rate.

  1. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium salt. 721.4040 Section 721.4040 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant...

  2. The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker.

    PubMed

    Marvania, Bhavin; Kakadiya, Rajesh; Christian, Wilson; Chen, Tai-Lin; Wu, Ming-Hsi; Suman, Sharda; Tala, Kiran; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long

    2014-08-18

    We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revealed that the C2-methylquinoline derivatives (18a-o) were generally more cytotoxic than the C2-phenylquinoline conjugates (23a-d) in inhibiting the cell growth of various human tumor cell lines in vitro. However, the methylamino or aniline substituents at C4 of quinoline did not influence the cytotoxic effects. The title conjugates were capable of inducing DNA cross-linking and promoting cell-cycle arrest at the G2/M phase. This study demonstrates that phenyl N-mustard-4-anilinoquinoline conjugates are generally more potent than phenyl N-mustard-4-anilinoquinazoline conjugates against the cell growth of various tumor cell-lines.

  3. Cytotoxic and Antitumour Studies of Acetoacetanilide N(4)-methyl(phenyl)thiosemicarbazone and its Transition Metal Complexes

    PubMed Central

    Priya, N. P.; Firdous, A. P.; Jeevana, R.; Aravindakshan, K. K.

    2015-01-01

    Cytotoxic activities of acetoacetanilide N(4)-methyl(phenyl)thiosemicarbazone (L2H) and its seven different metal complexes were studied. Of these, IC50 value of the copper complex was found to be 46 μg/ml. Antitumour studies of this copper complex was carried out using Daltons Lymphoma Ascites cell-induced solid tumour model and Ehrlich's Ascites Carcinoma cell-induced ascites tumour model. Administration of the copper complex at different concentrations (10, 5 and 1 mg/kg b. wt) inhibited the solid tumour development in mice and increased the mean survival rate and the life span of Ascites tumour bearing mice in a concentration dependent manner. PMID:26997691

  4. Three-Dimensional Carbon Allotropes Comprising Phenyl Rings and Acetylenic Chains in sp+sp(2) Hybrid Networks.

    PubMed

    Wang, Jian-Tao; Chen, Changfeng; Li, Han-Dong; Mizuseki, Hiroshi; Kawazoe, Yoshiyuki

    2016-01-01

    We here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+sp(2) bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp(2)-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells in the symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicate that phenylacetylene is metallic, while phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties.

  5. New phenyl derivatives from endophytic fungus Botryosphaeria sp. SCSIO KcF6 derived of mangrove plant Kandelia candel.

    PubMed

    Ju, Zhi-ran; Qin, Xiaochu; Lin, Xiu-ping; Wang, Jun-feng; Kaliyaperumal, Kumaravel; Tian, Yong-qi; Liu, Juan; Liu, Fen; Tu, Zhengchao; Xu, Shi-hai; Liu, Yonghong

    2016-01-01

    Two new phenyl derivatives (1 and 3), along with two new natural products (4 and 5), and three known compounds (2, 6 and 7), were isolated from an endophytic fungus Botryosphaeria sp. SCSIO KcF6. The structures of these compounds 1-7 were elucidated by the extensive 1D and 2D-NMR and HRESIMS Data analysis, and compared with those of reported data. The absolute configuration of the compounds 1 and 3 were assigned by optical rotation and CD data. The isolated compounds were evaluated for their cytotoxic, anti-inflammatory (COX-2) and antimicrobial activities. Compound 3 exhibited a specific COX-2 inhibitory activity with the IC50 value of 1.12 μM.

  6. [Design of Novel Carboxamides of Eremomycin and Vancomycin with 4- or 3-Amino Methyl Phenyl Boric Acid and Their Investigation].

    PubMed

    Bychkova, E N; Korolev, A M; Olsufyeva, E N; Mirchink, E P; Isakova, E B

    2015-01-01

    Amidation of the end carboxyl group of eremomycin and vancomycin by pinacolinic 4- or 3-amino methyl phenyl boron acids esters in the presence of the condensing reagent PyBOP resulted in formation of novel carboxamides of the antibiotics (IIIa-VIa). After elimination of the pinacolinic group under mild hydrolysis in weak acid aqueous medium there formed the respective derivatives with a residue of the nonprotected boric acid (III-VI). It was shown that the activity of the 4-substituted derivatives of the borole-containing eremomycin and vancomycin practically was the same as that of the initial antibiotics, while higher than that of the respective 3-substituted derivatives of the borole-containing derivatives against 8 strains of grampositive bacteria.

  7. Spectroscopic studies on 9H-carbazole-9-(4-phenyl) boronic acid pinacol ester by DFT method

    NASA Astrophysics Data System (ADS)

    Sas, E. B.; Kurt, M.; Can, M.; Horzum, N.; Atac, A.

    2016-08-01

    9H-Carbazole-9-(4-phenyl) boronic acid pinacol ester (9-CPBAPE) molecule was investigated by FT-IR, Raman, UV-vis, 1H and 13C NMR spectra. FT-IR, FT-Raman and dispersive Raman spectra were recorded in the solid phase. 1H, 13C NMR and UV-vis spectra were recorded in dimethyl sulfoxide (DMSO) solution. The results of theoretical calculations for the spectra of the title molecule were compared with the experimental spectra. The highest occupied molecular orbital (HOMO) the lowest unoccupied molecular orbital (LUMO) and molecular electrostatic potential (MEP) analyses were performed. The theoretical calculations for the molecular structure and spectroscopic studies were performed with DFT (B3LYP) and 6-311G (d,p) basis set calculations using the Gaussian 09 program. The total (TDOS), partial (PDOS) density of state and overlap population density of state (OPDOS) diagrams analyses were performed using GaussSum 2.2 program.

  8. Three-Dimensional Carbon Allotropes Comprising Phenyl Rings and Acetylenic Chains in sp+sp2 Hybrid Networks

    NASA Astrophysics Data System (ADS)

    Wang, Jian-Tao; Chen, Changfeng; Li, Han-Dong; Mizuseki, Hiroshi; Kawazoe, Yoshiyuki

    2016-04-01

    We here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+sp2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells in the symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicate that phenylacetylene is metallic, while phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties.

  9. 2-(4-Meth-oxy-phen-yl)-1-pentyl-4,5-di-phenyl-1H-imidazole.

    PubMed

    Simpson, Jim; Mohamed, Shaaban K; Marzouk, Adel A; Talybov, Avtandil H; Abdelhamid, Antar A

    2013-01-01

    The title compound, C27H28N2O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-meth-oxy substituent on the benzene ring. The two phenyl and meth-oxy-benzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the meth-oxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the meth-oxy C atom. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R2(2)(22) loops. These dimers are stacked along the a-axis direction. PMID:23476433

  10. 4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile

    PubMed Central

    Khan, F. Nawaz; Manivel, P.; Prabakaran, K.; Hathwar, Venkatesha R.; Akkurt, Mehmet

    2010-01-01

    In the title mol­ecule, C23H14N4, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.038 (2) Å and a maximum deviation of −0.030 (2) Å from the mean plane of the triazole ring C atom which is bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.65 (8) and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, mol­ecules are linked by weak aromatic π–π inter­actions [centroid–centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical inter­molecular C—H⋯N hydrogen bond. PMID:21579135

  11. 5-Phenyl-3-(2-thien­yl)-1,2,4-triazolo[3,4-a]isoquinoline

    PubMed Central

    Khan, F. Nawaz; Manivel, P.; Prabakaran, K.; Hathwar, Venkatesha R.; Ng, Seik Weng

    2010-01-01

    In the title mol­ecule, C20H13N3S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.045 Å and a maximum deviation of 0.090 (2) Å from the mean plane for the triazole ring C atom which is bonded to the thio­phene ring. The phenyl ring is twisted by 52.0 (1)° with respect to the mean plane of the triazoloisoquinoline ring system. The thio­phene ring is rotationally disordered by approximately 180° over two sites, the ratio of refined occupancies being 0.73 (1):0.27 (1). PMID:21579895

  12. Three-dimensional carbon allotropes comprising phenyl rings and acetylenic chains in sp+sp2 hybrid networks

    DOE PAGES

    Wang, Jian -Tao; Chen, Changfeng; Li, Han -Dong; Mizuseki, Hiroshi; Kawazoe, Yoshiyuki

    2016-04-18

    Here, we here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+sp2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells R-3m symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicate that phenylacetylene is metallic, whilemore » phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties.« less

  13. Three-Dimensional Carbon Allotropes Comprising Phenyl Rings and Acetylenic Chains in sp+sp2 Hybrid Networks

    PubMed Central

    Wang, Jian-Tao; Chen, Changfeng; Li, Han-Dong; Mizuseki, Hiroshi; Kawazoe, Yoshiyuki

    2016-01-01

    We here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+sp2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells in the symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicate that phenylacetylene is metallic, while phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties. PMID:27087405

  14. [1,5-Bis(2-meth-oxy-phen-yl)thio-carbazo-nato-κN,S]phenyl-mercury(II).

    PubMed

    von Eschwege, Karel; Muller, Fabian; Muller, Alfred

    2011-12-01

    The title compound, [Hg(C(6)H(5))(C(15)H(15)N(4)O(2)S)], shows the metal-phenyl moiety coordinated out of plane with the thio-carbazo-nate ligand by 43.84 (6)°. Important geometrical parameters include Hg-S = 2.3653 (10) Å, Hg-C = 2.058 (4) Å and S-Hg-C = 179.06 (11)°. There is a weak coordination of an N atom of the ligand to Hg [Hg-N = 2.725 (3) Å]. S⋯Hg inter-actions[3.2928 (10) Å] form chains along [001], stabilizing the crystal structure. PMID:22199587

  15. Crystal structure of catena-poly[[di-aqua-cadmium(II)]-μ-3,3'-(1,3-phenyl-ene)diacrylato].

    PubMed

    Zhang, Xiao-Ping; Chen, Xin; Huang, Kun-Lin

    2015-04-01

    In the crystal of the title polymeric complex, [Cd(C12H8O4)(H2O)2] n , the Cd(II) cation, located on a twofold rotation axis, is coordinated by two water mol-ecules and chelated by two phenyl-enediacrylate anions (mpda) in a distorted octa-hedral geometry. The mpda anions bridge the Cd(II) cations, forming helical chains propagating along the c-axis direction. The mpba anion has twofold symmetry with two benzene C atoms located on the twofold rotation axis. In the crystal, O-H⋯O hydrogen bonds link the polymeric helical chains into a three-dimensional supra-molecular architecture. PMID:26029417

  16. Effective attenuation of atrazine-induced histopathological changes in testicular tissue by antioxidant N-phenyl-4-aryl-polyhydroquinolines.

    PubMed

    Chandak, Navneet; Bhardwaj, Jitender K; Zheleva-Dimitrova, Dimitrina; Kitanov, Gerassim; Sharma, Rajnesh K; Sharma, Pawan K; Saso, Luciano

    2015-01-01

    Some of the environmental toxicants acting as endocrine disruptors have been associated with health hazards in human and wildlife by modulating hormonal actions. Atrazine, a strong endocrine disruptor, induces detrimental effects on gonads in male and female, and causes impairment of fertility and developmental problems as well as sex alterations. Atrazine decreases the activities of antioxidant enzymes and thus responsible for oxidative stress. Natural antioxidants have shown ability to reduce/slow down the apoptotic effect of atrazine on testicular tissue. In the present study, some N-phenyl-4-aryl-polyhydroquinolines bearing phenolic or/and alkoxy group(s) (6a-6g) were synthesized and evaluated for antioxidant activity in four different assays. Three best compounds (6e-6g) were studied for their ameliorative effect on testicular tissue supplemented with atrazine in vitro.

  17. Reaction progress kinetic analysis of a copper-catalyzed aerobic oxidative coupling reaction with N-phenyl tetrahydroisoquinoline.

    PubMed

    Scott, Martin; Sud, Abhishek; Boess, Esther; Klussmann, Martin

    2014-12-19

    The results from a kinetic investigation of a Cu-catalyzed oxidative coupling reaction between N-phenyl tetrahydroisoquinoline and a silyl enol ether using elemental oxygen as oxidant are presented. By using reaction progress kinetic analysis as an evaluation method for the obtained data, we discovered information regarding the reaction order of the substrates and catalysts. Based on this information and some additional experiments, a refined model for the initial oxidative activation of the amine substrate and the activation of the nucleophile by the catalyst was developed. The mechanistic information also helped to understand why silyl nucleophiles have previously failed in a related Cu-catalyzed reaction using tert-butyl hydroperoxide as oxidant and how to overcome this limitation. PMID:25203932

  18. Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

    PubMed Central

    2012-01-01

    Background A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. Results The structure of the dyes was confirmed by UV-vis, FT-IR, 1H NMR and 13C NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. Conclusions The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data. PMID:22824496

  19. Copper(II) complexes derived from di-2-pyridyl ketone- N4-phenyl-3-semicarbazone: Synthesis and spectral studies

    NASA Astrophysics Data System (ADS)

    Reena, T. A.; Kurup, M. R. Prathapachandra

    2010-08-01

    Five copper(II) complexes [CuLCl] 2·CuCl 2·4H 2O ( 1), [CuLOAc] ( 2), [CuLNO 3] 2 ( 3), [CuLN 3] ( 4) and [CuLNCS]·3/2H 2O ( 5) of di-2-pyridyl ketone- N4-phenyl-3-semicarbazone (HL) were synthesized and characterized by elemental analyses and electronic, infrared and EPR spectral techniques. In all these complexes the semicarbazone undergoes deprotonation and coordinates through enolate oxygen, azomethine and pyridyl nitrogen atoms. All the complexes are EPR active due to the presence of an unpaired electron. EPR spectra of all the complexes in DMF at 77 K suggest axial symmetry and the presence of half field signals for the complexes 1 and 3 indicates dimeric structures.

  20. The optical properties, synthesis and characterization of novel 5-aryl-3-benzimidazolyl-1-phenyl-pyrazoline derivatives

    NASA Astrophysics Data System (ADS)

    Cao, Xiao Qun; Lin, Xiao Hui; Zhu, Yan; Ge, Yan Qing; Wang, Jian Wu

    2012-12-01

    A series of novel 5-aryl-3-benzimidazolyl-1-phenyl-pyrazoline derivatives were synthesized by the reaction of benzimidazolyl chalcone and phenylhydrazine in 41-72% yields. The compounds were characterized using IR, 1H NMR and HRMS. Absorption and fluorescence spectra were measured in different organic solvent. An intense absorption maxima was noted at ca. 370 nm and emission maxima was noted at ca. 460 nm. The absorption spectra of the pyrazoline derivatives reveal that 5-aryl group attached to the pyrazoline ring hardly influenced the maximum absorption. The fluorescence spectra of these compounds indicated the emission wavelength was red shifted and the fluorescence intensity was decreased with the increase in solvent polarity.

  1. Quantum mechanics study of repulsive π-π interaction and flexibility of phenyl moiety in the iron azodioxide complex

    NASA Astrophysics Data System (ADS)

    Liu, Yuemin; Liu, Yucheng; Murru, Siva; Tzeng, Nianfeng; Srivastava, Radhey S.

    2015-10-01

    In this study, repulsive π-π interactions within iron azodioxide complex Fe[Ph(O)NN(O)Ph]3 were quantum mechanically characterized using DFT, MP2 and CCSD(T) methods. Flexibility of six phenyl moieties in this complex structure was also investigated by structural optimization approach using the DFT methods. Our MP2 and CCSD(T) calculations of the closest pair provided interaction energy of 6.62 and 8.29 kcal/mol respectively, which indicate a strongest repulsion among these intra-molecular π-π interactions. Interaction energy of the particular π-π pair calculated from 24 hybrid DFT methods ranges from 4.56 kcal/mol from BHandH method to 15.15 kcal/mol from O3LYP method. Cares should be exercised when interpreting interaction energy and geometry optimization from DFT simulation of systems containing π-π interaction. Comparison between the DFT results and the benchmark CCSD(T) results shows that the DFT calculations of π-π interaction are reasonable but still need to be interpreted with caution. Furthermore, MP2 interaction energy of -44.69 kcal/mol between two substituted π systems/phenyl rings Ph(O)N-moieties suggested that above energetically unfavorable π-π interaction can be compensated by the covalent bond N-N in a single ligand Ph(O)NN(O)Ph, which allows for a reasonable stability across the complex molecules. Optimizations of the entire complex molecule using B3LYP and M06HF methods produced a large variation of π-π distances and orientations, which implied that the complex molecule may perform catalysis at room temperature.

  2. Design, synthesis and biological evaluation of novel benzimidazole-2-substituted phenyl or pyridine propyl ketene derivatives as antitumour agents.

    PubMed

    Wu, Lin-tao; Jiang, Zhi; Shen, Jia-jia; Yi, Hong; Zhan, Yue-chen; Sha, Ming-quan; Wang, Zhen; Xue, Si-tu; Li, Zhuo-rong

    2016-05-23

    A series of novel benzimidazole-2-subsituted phenyl or pyridine propyl ketene derivatives were designed and synthesized. The biological activities of these derivatives were then evaluated as potential antitumour agents. These compounds were assayed for growth-inhibitory activity against HCT116, MCF-7 and HepG2 cell lines in vitro. The IC50 values of compounds A1 and A7 against the cancer cells were 0.06-3.64 μM and 0.04-9.80 μM, respectively. Their antiproliferative activities were significantly better than that of 5-Fluorouracil (IC50: 56.96-174.50 μM) and were close to that of Paclitaxel (IC50: 0.026-1.53 μM). The activity of these derivatives was over 100 times more effective than other reported structures of chalcone analogues (licochalcone A). A preliminary mechanistic study suggested that these compounds inhibit p53-MDM2 binding. Compounds A1, A7 and A9 effectively inhibited tumour growth in BALB/c mice with colon carcinoma HCT116 cells. The group administered 200 mg/kg of compound A7 showed a 74.6% tumour growth inhibition with no signs of toxicity at high doses that was similar to the inhibition achieved with the 12.5 mg/kg irinotecan positive control (70.2%). Therefore, this class of benzimidazole-2-subsituted phenyl or pyridine propyl ketene derivatives represents a promising lead structure for the development of possible p53-MDM2 inhibitors as new antitumour agents. PMID:27017265

  3. Structural and photophysical properties of HPPCO (4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one) derivatives

    NASA Astrophysics Data System (ADS)

    Jeong, Yong-Kwang; Kim, Min-Ah; Lee, Hyo-Sung; Kim, Jong-Moon; Lee, Sung Woo; Kang, Jun-Gill

    2015-01-01

    Proton-substitution effects of 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one (HPPCO) on structural and photophysical properties were presented. HPPCO crystallized in the orthorhombic space group Pbca with an intermolecular hydrogen bonding between OH and oxygen atom of the carbonyl. The proton-substituted derivatives, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl acetate (OPPCA) and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl benzoate (OPPCB), crystallized in the monoclinic P21/c space group. For OPPCA and OPPCB, a weak interaction between carbonyl oxygen atom in the substituted group and carbon atom in the fused ring was responsible for three-dimensional arrangements. In addition, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl furan-2-carboxylate (OPPCF), and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl naphthoate (OPPCN) were also synthesized. HPPCO and the four derivatives excited by ultraviolet (UV) light produced blue emission. Proton substitution of the OH group significantly increased the radiative transitions and moderately decreased the non-radiative transitions. Consequently the luminescence quantum yields of the derivatives enhanced more than 4.6-fold, no matter what the groups were substituted. Structural and optical properties were further determined using density functional theory (DFT) and ZINDO calculations. The planar structure of the pyridocarbazole-fused ring resulted in π → π* electronic transitions within the main frame, with an additional transition from the n(O) of carbonyl to the π* of the main frame. The three excited states that arose from these transitions were responsible for the blue luminescence.

  4. Microwave-assisted syntheses of N-heterocycles using alkenone-, alkynone- and aryl-carbonyl O-phenyl oximes: formal synthesis of neocryptolepine.

    PubMed

    Portela-Cubillo, Fernando; Scott, Jackie S; Walton, John C

    2008-07-18

    This research aimed to provide a new and "clean" synthetic method that would enable both known and novel N-heterocycles to be prepared efficiently. O-Phenyl oximes were found to be excellent precursors for iminyl radicals with a variety of acceptor side chains. Dihyropyrroles were made in good yields from O-phenyl oximes containing pent-4-ene acceptors. The analogous process with a hex-5-enyl acceptor did not yield a dihydropyridine, probably because the 6-exo-trig ring closure of the iminyl radical was too slow to compete with H-atom abstraction. The iminyl radical from a precursor with a pent-4-yne type side chain underwent ring closure followed by rearrangement to afford a pyrrole derivative. Suitably substituted iminyl radicals ring closed readily onto aromatic acceptors, thus enabling several polycyclic systems to be accessed. Quinolines were made from 3-phenylpropanones via their O-phenyl oximes. Syntheses of phenanthridines starting from 2-formylbiphenyls were particularly efficient, and this approach enabled the natural product trisphaeridine to be made. Starting from 2-phenylnicotinaldehyde derivatives, ring closures of the derived iminyl radicals onto the phenyl rings yielded benzo[h][1,6]naphthyridines. Similarly, ring closure onto a phenyl ring from a benzothiophene-based iminyl yielded a benzo[b]thieno[2,3-c]quinoline. By way of contrast, iminyl radical ring closure onto pyridine rings was not observed. However, iminyl radicals did cyclize onto indoles, enabling indolopyridines to be prepared. The latter route was exploited in a short formal synthesis of neocryptolepine starting from 2-((1H-indol-3-yl)methyl)cyclohexanone.

  5. Crystal structure of the 1:1 adduct of 2,3-diphenyl-3,4,5,6-tetra-hydro-2H-1,3-thia-zin-4-one with tri-phenyl-tin chloride.

    PubMed

    Yennawar, Hemant P; Fox, Ryan; Silverberg, Lee J

    2016-03-01

    The title adduct, chlorido-(2,3-diphenyl-3,4,5,6-tetra-hydro-2H-1,3-thia-zin-4-one-κO)tri-phenyl-tin, [Sn(C6H5)3Cl(C16H15NOS)], resulted from reaction of 2,3-diphenyl-3,4,5,6-tetra-hydro-2H-1,3-thia-zin-4-one with tri-phenyl-tin chloride. The thia-zine ring has an envelope conformation with the S atom forming the flap. The mol-ecule has five phenyl rings, two of them attached to the thia-zine ring at positions 2 and 3, and three in coordination with the Sn(IV) atom. The three rings of the tri-phenyl-tin group are involved in intra-molecular inter-actions of different types, C-H⋯O, edge-to-face (or T-type) π-π inter-actions with the 3-phenyl ring of the thia-zine, T-type inter-actions with both phenyl rings of the thia-zine etc. On the other hand, all the phenyl rings participate in inter-molecular π-π inter-actions. There is one instance of a 'parallel-displaced'-type inter-action extending continuously along the a-axis direction and seven instances of T-type inter-actions stabilizing the crystal lattice.

  6. 2-[2-(5-Bromo­thio­phen-2-yl)-4,5-diphenyl-1H-imidazol-1-yl]-3-phenyl­propan-1-ol

    PubMed Central

    Gao, Jie; Yang, Liangru; Mai, Wenpeng; Yuan, Jinwei; Mao, Pu

    2013-01-01

    In the title compound, C28H23BrN2OS, the dihedral angles formed by the imidazole ring with the 5-bromo­thio­phenyl and phenyl rings are 76.90 (8), 34.02 (10) and 80.93 (11)°, respectively. The chiral centre maintains the S configuration of the l-phenyl­alaninol starting material. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming chains running parallel to the a-axis direction. PMID:24427022

  7. Product branching ratios in photodissociation of phenyl radical: A theoretical ab initio/Rice-Ramsperger-Kassel-Marcus study

    NASA Astrophysics Data System (ADS)

    Mebel, Alexander M.; Landera, Alexander

    2012-06-01

    Ab initio CCSD(T)/CBS//B3LYP/6-311G** calculations of the potential energy surface for possible dissociation channels of the phenyl radical are combined with microcanonical Rice-Ramsperger-Kassel-Marcus calculations of reaction rate constants in order to predict statistical product branching ratios in photodissociation of c-C6H5 at various wavelengths. The results indicate that at 248 nm the photodissociation process is dominated by the production of ortho-benzyne via direct elimination of a hydrogen atom from the phenyl radical. At 193 nm, the statistical branching ratios are computed to be 63.4%, 21.1%, and 14.4% for the o-C6H4 + H, l-C6H4 ((Z)-hexa-3-ene-1,5-diyne) + H, and n-C4H3 + C2H2 products, respectively, in a contradiction with recent experimental measurements, which showed C4H3 + C2H2 as the major product. Although two lower energy pathways to the i-C4H3 + C2H2 products are identified, they appeared to be kinetically unfavorable and the computed statistical branching ratio of i-C4H3 + C2H2 does not exceed 1%. To explain the disagreement with experiment, we optimized conical intersections between the ground and the first excited electronic states of C6H5 and, based on their structures and energies, suggested the following photodissociation mechanism at 193 nm: c-C6H5 1 → absorption of a photon → electronically excited 1 → internal conversion to the lowest excited state → conversion to the ground electronic state via conical intersections at CI-2 or CI-3 → non-statistical decay of the vibrationally excited radical favoring the formation of the n-C4H3 + C2H2 products. This scenario can be attained if the intramolecular vibrational redistribution in the CI-2 or CI-3 structures in the ground electronic state is slower than their dissociation to n-C4H3 + C2H2 driven by the dynamical preference.

  8. Product branching ratios in photodissociation of phenyl radical: A theoretical ab initio/Rice-Ramsperger-Kassel-Marcus study

    SciTech Connect

    Mebel, Alexander M.; Landera, Alexander

    2012-06-21

    Ab initio CCSD(T)/CBS//B3LYP/6-311G** calculations of the potential energy surface for possible dissociation channels of the phenyl radical are combined with microcanonical Rice-Ramsperger-Kassel-Marcus calculations of reaction rate constants in order to predict statistical product branching ratios in photodissociation of c-C{sub 6}H{sub 5} at various wavelengths. The results indicate that at 248 nm the photodissociation process is dominated by the production of ortho-benzyne via direct elimination of a hydrogen atom from the phenyl radical. At 193 nm, the statistical branching ratios are computed to be 63.4%, 21.1%, and 14.4% for the o-C{sub 6}H{sub 4}+ H, l-C{sub 6}H{sub 4} ((Z)-hexa-3-ene-1,5-diyne) + H, and n-C{sub 4}H{sub 3}+ C{sub 2}H{sub 2} products, respectively, in a contradiction with recent experimental measurements, which showed C{sub 4}H{sub 3}+ C{sub 2}H{sub 2} as the major product. Although two lower energy pathways to the i-C{sub 4}H{sub 3}+ C{sub 2}H{sub 2} products are identified, they appeared to be kinetically unfavorable and the computed statistical branching ratio of i-C{sub 4}H{sub 3}+ C{sub 2}H{sub 2} does not exceed 1%. To explain the disagreement with experiment, we optimized conical intersections between the ground and the first excited electronic states of C{sub 6}H{sub 5} and, based on their structures and energies, suggested the following photodissociation mechanism at 193 nm: c-C{sub 6}H{sub 5} 1{yields} absorption of a photon {yields} electronically excited 1{yields} internal conversion to the lowest excited state {yields} conversion to the ground electronic state via conical intersections at CI-2 or CI-3{yields} non-statistical decay of the vibrationally excited radical favoring the formation of the n-C{sub 4}H{sub 3}+ C{sub 2}H{sub 2} products. This scenario can be attained if the intramolecular vibrational redistribution in the CI-2 or CI-3 structures in the ground electronic state is slower than their dissociation to n-C{sub 4}H

  9. Second monoclinic form of (E)-3-(4-fluoro­phen­yl)-1-phenyl­prop-2-en-1-one

    PubMed Central

    Arias-Ruiz, Saira N.; Romero, Nancy; Lobato-García, Carlos E.; Gómez-Rivera, Abraham; Mendoza, Angel

    2013-01-01

    The unit-cell dimensions and space group of the second monoclinic polymorph of the title compound, C15H11FO, differ from those of the previously reported form [Jing (2009 ▶). Acta Cryst. E65, o2515]. The title compound shows an E conformation of the C=C bond with the 4-fluoro­phenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluoro­phenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C—H⋯O and C—H⋯F inter­actions form a cross-linked packing motif, building sheets parallel to (-102). PMID:24454121

  10. Studies on Absorption and Emission Characteristics of Inclusion Complexes of Some 4-Arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols.

    PubMed

    Panda, Sunakar; Nayak, Sashikanta

    2016-03-01

    The inclusion complexes of a series of 4-arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols have been prepared with β-cyclodextrin. The compounds and their inclusion complexes have been characterized by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes and type of host-guest relation. Finally, absorption, excitation and emission spectra of the compounds (4-arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols) and their inclusion complexes have been taken. It is found that inclusion complex formation brings about a drastic change in absorption and fluorescence characteristic (both excitation and emission spectra) of newly synthesized compounds.

  11. Crystal structure of 2-[2-(hy­droxy­imino)-1-phenyl­propyl­idene]-N-phen­ylhydrazinecarbo­thio­amide

    PubMed Central

    Anderson, Brian J.; Freedman, Michael B.; Millikan, Sean P.; Smolenski, Victoria A.; Jasinski, Jerry P.

    2015-01-01

    In the title compound, C16H16N4OS, an intra­molecular C—H⋯S hydrogen bond is observed. With the exception of the phenyl ring of the phenyl­propyl­idene unit, the remainder of the mol­ecule has an almost planar skeleton with an r.m.s. deviation of 0.121 (5) Å from the plane through the remaining 16 atoms. In the crystal O—H⋯N hydrogen bonds are observed between the terminal hy­droxy­imino groups, forming inverson dimers with R 2 2(6) graph-set motifs. Additional C—H⋯N contacts stack the dimers along [100]. While no π—π inter­actions are present, weak C—H⋯O and O—H⋯Cg inter­actions are also observed and help stabilize the crystal packing. PMID:26594484

  12. Syntheses, structures and properties of two new coordination polymers based on D-camphoric acid and 2-phenyl-4,6-diamino-1,3,5-triazine

    NASA Astrophysics Data System (ADS)

    Lun, Huijie; Yang, Jinghe; Jin, Linyu; Cui, Sasa; Bai, Yanlong; Zhang, Xudong; Li, Yamin

    2015-05-01

    By hydrothermal method, two new coordination polymers [Co(ca)(phdat)]n (1), [Ni(ca)(phdat).0.125H2O]n (2) (H2ca=D-camphoric acid, phdat=2-phenyl-4,6-diamino-1,3,5-triazine) have been achieved and structurally characterized by IR, elemental analyses, X-ray single-crystal diffraction and TGA. The X-ray single-crystal diffraction reveals that compounds 1 and 2 are isostructural, both of which exhibit two-dimensional layered network built up from paddle-wheel Co2(CO2)4/Ni2(CO2)4 SBUs by ca2- ligand. In the existence of π…π stacking interactions between triazine rings and phenyl rings, the 3D networks are constructed with the hanging phdat filled between the neighboring layers. Furthermore, compounds 1-2 exhibit antiferromagnetic behavior and compound 2 displays a good activity for methanol oxidation.

  13. Oxidation of phenyl propyne catalyzed by copper(II) complexes of a benzimidazolyl schiff base ligand: Effect of acid/base, oxidant, surfactant and morphology

    NASA Astrophysics Data System (ADS)

    Kumar, Ravinder; Mathur, Pavan

    2015-02-01

    Copper(II) complexes with a new N-Substituted benzimidazolyl schiff base ligand are used as catalyst for the oxidation of 1-phenyl propyne. The oxidation is carried out under mild conditions using stoichiometric amounts of oxidant and catalytic amounts of Cu(II) complex as catalyst. Effect of acid/base, oxidant, morphology and surfactant has been studied. Two major products of phenyl propyne oxidation are the α-diketonic product and a terminal aldehyde. Diketone is the major product under acidic conditions while aldehyde formation is highest under basic conditions. The maximum conversion is found with the NO3- bound complex. GC-MS is used to find the percentage yields of products. SEM and PXRD of the reused complexes as catalyst suggest that morphology affects the catalytic efficiency.

  14. N-[(3-Ethyl­phen­yl)carbamo­thio­yl]-2,2-di­phenyl­acetamide

    PubMed Central

    Yusof, Mohd Sukeri Mohd; Razali, Nur Rafikah; Arshad, Suhana; Rahman, Azhar Abdul; Razak, Ibrahim Abdul

    2013-01-01

    In the title mol­ecule, C23H22N2OS, the di­phenyl­acetyl and ethyl­benzene groups adopt a trans–cis conformation, respectively, with respect to the S atom across the (S=)C—N bonds. This conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond and a weak C—H⋯S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N—H⋯O hydrogen bonds link mol­ecules into chains along [100]. A weak C—H⋯π inter­action is also observed. PMID:24046599

  15. Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-amino-phenyl-arsonate tetra-hydrate.

    PubMed

    Smith, Graham; Wermuth, Urs D

    2016-05-01

    In the structure of the brucinium salt of 4-amino-phenyl-arsonic acid (p-arsanilic acid), systematically 2,3-dimeth-oxy-10-oxostrychnidinium 4-amino-phenyl-ar-son-ate tetra-hydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water mol-ecules of solvation are accommodated between the layers and are linked to them through a primary cation N-H⋯O(anion) hydrogen bond, as well as through water O-H⋯O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure. PMID:27308034

  16. {Dimeth-yl [(phenyl-sulfon-yl)amido-]phosphato-κ(2) O,O'}bis-(tri-phenylphosphane-κP)copper(I).

    PubMed

    Moroz, Olesia V; Trush, Viktor A; Sliva, Tatiana Yu; Znovjyak, Kateryna O; Amirkhanov, Vladimir M

    2014-06-01

    In the title complex, [Cu(C8H11NO5PS)(C18H15P)2], the Cu(I) ion is coordinated by two tri-phenyl-phosphane mol-ecules and two O atoms of the chelating dimeth-yl(phenyl-sulfon-yl)amido-phosphate anion, generating a squashed CuO2P2 tetrahedron. In the six-membered chelate ring, the Cu, P and O atoms are almost coplanar (r.m.s. deviation = 0.024 Å), with the N and S atoms displaced in the same direction, by 0.708 (5) and 0.429 (2) Å, respectively.

  17. Crystal structure of N 1-phenyl-N 4-[(E)-(pyren-1-yl)methyl­idene]benzene-1,4-di­amine

    PubMed Central

    Faizi, Md. Serajul Haque; Prisyazhnaya, Elena V.

    2015-01-01

    In the title compound, C29H20N2, the dihedral angles subtended by the central p-phenyl­enedi­amine ring with respect to the mean plane of the terminal pyrenyl ring system (r.m.s. deviation = 0.027 Å) and the terminal N-phenyl ring are 29.34 (4) and 43.43 (7)°, respectively. The conformation about the C=N bond is E. In the crystal, mol­ecules are linked by N—H⋯π and C—H⋯π inter­actions forming chains propagating along the [10-2] direction. These chains are linked via π–π inter­actions [inter-centroid distances are in the range 3.5569 (11)–3.708 (1) Å], forming slabs lying parallel to (30-4). PMID:25844182

  18. Crystal structure of (E)-4-[N-(7-methyl-2-phenyl­imidazo[1,2-a]pyridin-3-yl)carboximido­yl]phenol

    PubMed Central

    Elaatiaoui, Abdelmalik; Saddik, Rafik; Benchat, Noureddine; Saadi, Mohamed; El Ammari, Lahcen

    2015-01-01

    The mol­ecule of the title compound, C21H17N3O, is built up from fused five- and six-membered rings connected to a methyl group, a phenyl ring and an (imino­meth­yl)phenol group. The fused ring system is almost planar (r.m.s. deviation = 0.031 Å) and forms dihedral angles of 64.97 (7) and 18.52 (6)° with the phenyl ring and the (imino­meth­yl)phenol group, respectively. In the crystal, centrosymmetric mol­ecules are linked by pairs of C—H⋯π inter­actions into dimeric units, which are further connected by O–H⋯N hydrogen bonds to form layers parallel to (101). PMID:26594488

  19. Crystal structure of (3E)-3-[(4-nitro-phen-oxy)-meth-yl]-4-phenyl-but-3-en-2-one.

    PubMed

    Zukerman-Schpector, Julio; Maganhi, Stella H; Moran, Paulo J S; de Paula, Bruno R S; Nucci, Paulo R; Tiekink, Edward R T

    2014-09-01

    In the title compound, C17H15NO4, the conformation about the C=C double bond [1.348 (2) Å] is E with the ketone group almost co-planar [C-C-C-C torsion angle = 7.2 (2)°] but the phenyl group twisted away [C-C-C-C = 160.93 (17)°]. The terminal aromatic rings are almost perpendicular to each other [dihedral angle = 81.61 (9)°] giving the mol-ecule an overall U-shape. The crystal packing feature benzene-C-H⋯O(ketone) contacts that lead to supra-molecular helical chains along the b axis. These are connected by π-π inter-actions between benzene and phenyl rings [inter-centroid distance = 3.6648 (14) Å], resulting in the formation of a supra-molecular layer in the bc plane. PMID:25309202

  20. Crystal structure of fac-tricarbon-yl(quinoline-2-carboxyl-ato-κ(2) N,O)(tri-phenyl-arsane-κAs)rhenium(I).

    PubMed

    Triantis, Charalampos; Shegani, Antonio; Kiritsis, Christos; Raptopoulou, Catherine P; Psycharis, Vassilis; Pelecanou, Maria; Pirmettis, Ioannis; Papadopoulos, Minas

    2016-02-01

    In the title compound, [Re(C10H6NO2)(CO)3{As(C6H5)3}], the coordination environment of Re(I) is that of a distorted octa-hedron. Three coordination sites are occupied by three carbonyl groups in a facial arrangement and the remaining three sites by tri-phenyl-arsane and deprotonated quinaldic acid in As-mono- and N,O-bidentate fashions, respectively. In the crystal, the complexes are linked through weak C-H⋯O hydrogen bonds, forming a three-dimensional network. It worth noting that, as far as we know, this complex is the first Re(I) tri-phenyl-arsane tricarbonyl compound to be reported. PMID:26958366

  1. Oxidation of phenyl propyne catalyzed by copper(II) complexes of a benzimidazolyl schiff base ligand: effect of acid/base, oxidant, surfactant and morphology.

    PubMed

    Kumar, Ravinder; Mathur, Pavan

    2015-02-01

    Copper(II) complexes with a new N-Substituted benzimidazolyl schiff base ligand are used as catalyst for the oxidation of 1-phenyl propyne. The oxidation is carried out under mild conditions using stoichiometric amounts of oxidant and catalytic amounts of Cu(II) complex as catalyst. Effect of acid/base, oxidant, morphology and surfactant has been studied. Two major products of phenyl propyne oxidation are the α-diketonic product and a terminal aldehyde. Diketone is the major product under acidic conditions while aldehyde formation is highest under basic conditions. The maximum conversion is found with the NO3(-) bound complex. GC-MS is used to find the percentage yields of products. SEM and PXRD of the reused complexes as catalyst suggest that morphology affects the catalytic efficiency. PMID:25448979

  2. (S)-(−)-2-(1H-Indol-3-yl)-N-(1-phenyl­eth­yl)acetamide

    PubMed Central

    Ramírez, Johana; Romero, Oscar; Juárez, Jorge R.; Terán, Joel L.; Mendoza, Angel

    2012-01-01

    In the title compound, C18H18N2O, the dihedral angle between the indole system and the phenyl ring is 17.2 (2)°. The crystal packing features two N—H⋯O hydrogen bonds, which link the mol­ecules into layers parallel to (001). The absolute configuration was determined by the synthetic procedure and was set according to the starting material. PMID:22798904

  3. Synthesis, spectroscopic investigations (X-ray, NMR and TD-DFT), antimicrobial activity and molecular docking of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone.

    PubMed

    Barakat, Assem; Ghabbour, Hazem A; Al-Majid, Abdullah Mohammed; Soliman, Saied M; Ali, M; Mabkhot, Yahia Nasser; Shaik, Mohammed Rafi; Fun, Hoong-Kun

    2015-07-21

    The synthesis of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone 1 is described. The molecular structure of the title compound 1 was confirmed by NMR, FT-IR, MS, CHN microanalysis, and X-ray crystallography. The molecular structure was also investigated by a set of computational studies and found to be in good agreement with the experimental data obtained from the various spectrophotometric techniques. The antimicrobial activity and molecular docking of the synthesized compound was investigated.

  4. Sequential Addition Reaction of Sulfanylmethyllithiums and Grignard Reagents to Thioformamides Leading to the Formation of 2-Phenyl-2-sulfanylethyl Tertiary Amines.

    PubMed

    Murai, Toshiaki; Mutoh, Natsumi

    2016-09-16

    The reaction of sulfanylmethyllithiums generated from benzylsulfanes and n-BuLi with N,N-dimethylthioformamide followed by the addition of Grignard reagents gave 2-phenyl-2-sulfanyl tertiary amines in moderate to good yields. A range of Grignard reagents involving primary alkyl, aryl, vinyl, and alkynyl Grignard reagents were used. Two carbon-carbon bond-forming reactions were achieved through a one-pot reaction. The reaction showed good to high diastereoselectivity, particularly with alkynyl Grignard reagents. PMID:27565031

  5. Supramolecular engineering through temperature-induced chemical modification of 2H-tetraphenylporphyrin on Ag(111): flat phenyl conformation and possible dehydrogenation reactions.

    PubMed

    Di Santo, Giovanni; Blankenburg, Stephan; Castellarin-Cudia, Carla; Fanetti, Mattia; Borghetti, Patrizia; Sangaletti, Luigi; Floreano, Luca; Verdini, Alberto; Magnano, Elena; Bondino, Federica; Pignedoli, Carlo A; Nguyen, Manh-Thuong; Gaspari, Roberto; Passerone, Daniele; Goldoni, Andrea

    2011-12-16

    Scratching the surface: Formation of a monolayer of 2H-tetraphenylporphyrins (2H-TPP) on Ag(111), either by sublimation of a multilayer in the range 525-600 K or by annealing (at the same temperature) a monolayer deposited at room temperature, induces a chemical modification of the molecules. Rotation of the phenyl rings into a flat conformation is observed and tentatively explained, by using DFT calculations, as a peculiar reaction due to molecular dehydrogenation. PMID:22113855

  6. Synthesis of 8-phenyl-10H-pyrido(1,2-. cap alpha. )indole salts from 2,3,3-trimethyl-3H-indole chlorides with cinnamaldehyde

    SciTech Connect

    Shachkus, A.A.; Degutis, Yu.A.

    1987-10-01

    Reaction of 2,3,3-trimethyl-3H-indole chloride with cinnamic and 4-dimethylaminocinnamic aldehydes led to salts of 8-phenyl and 8-(4-dimethylaminophenyl)-10,10-dimethyl-10H-pyrido(1,2-..cap alpha..)indole. PMR spectra were recorded on a Tesla BS-487C (80 MHz) instrument (internal standard HMDS) and IR spectra on a UR-20 spectrometer (KBr pellets).

  7. Synthesis, Antiviral and Cytotoxic Activities of 2-(2-Phenyl carboxylic acid)-3-Phenylquinazolin -4(3H)-one Derivatives

    PubMed Central

    Selvam, P.; Murugesh, N.; Chandramohan, M.; Pannecouque, C.; DE Clercq, E.

    2010-01-01

    A series of novel 2,3-disubstitutedquinazolin-4(3H)-ones have been synthesized by condensation of 2-substituted benzo[1,3]oxazine-4-ones and anthranilic acid. Synthesized compounds were evaluated for in vitro antiviral activity against HIV, HSV and vaccinia viruses. 5-Bromo-2-(6-bromo-4-oxo-2-phenyl-4H-quinazolin-3-yl)-benzoic acid (MBR2) exhibited distinct antiviral activity against Herpes simplex and vaccinia viruses. PMID:21969760

  8. Synthesis, Antiviral and Cytotoxic Activities of 2-(2-Phenyl carboxylic acid)-3-Phenylquinazolin -4(3H)-one Derivatives.

    PubMed

    Selvam, P; Murugesh, N; Chandramohan, M; Pannecouque, C; DE Clercq, E

    2010-11-01

    A series of novel 2,3-disubstitutedquinazolin-4(3H)-ones have been synthesized by condensation of 2-substituted benzo[1,3]oxazine-4-ones and anthranilic acid. Synthesized compounds were evaluated for in vitro antiviral activity against HIV, HSV and vaccinia viruses. 5-Bromo-2-(6-bromo-4-oxo-2-phenyl-4H-quinazolin-3-yl)-benzoic acid (MBR2) exhibited distinct antiviral activity against Herpes simplex and vaccinia viruses.

  9. Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides.

    PubMed

    Daifuku, Stephanie L; Kneebone, Jared L; Snyder, Benjamin E R; Neidig, Michael L

    2015-09-01

    While previous studies have identified FeMes2(SciOPP) as the active catalyst species in iron-SciOPP catalyzed Kumada cross-coupling of mesitylmagnesium bromide and primary alkyl halides, the active catalyst species in cross-couplings with phenyl nucleophiles, where low valent iron species might be prevalent due to accessible reductive elimination pathways, remains undefined. In the present study, in situ Mössbauer and magnetic circular dichroism spectroscopic studies combined with inorganic syntheses and reaction studies are employed to evaluate the in situ formed iron species and identify the active catalytic species in iron-SciOPP catalyzed Suzuki-Miyaura and Kumada cross-couplings of phenyl nucleophiles and secondary alkyl halides. While reductive elimination to form Fe(η(6)-biphenyl)(SciOPP) occurs upon reaction of FeCl2(SciOPP) with phenyl nucleophiles, this iron(0) species is not found to be kinetically competent for catalysis. Importantly, mono- and bis-phenylated iron(II)-SciOPP species that form prior to reductive elimination are identified, where both species are found to be reactive toward electrophile at catalytically relevant rates. The higher selectivity toward the formation of cross-coupled product observed for the monophenylated species combined with the undertransmetalated nature of the in situ iron species in both Kumada and Suzuki-Miyaura reactions indicates that Fe(Ph)X(SciOPP) (X = Br, Cl) is the predominant reactive species in cross-coupling. Overall, these studies demonstrate that low-valent iron is not required for the generation of highly reactive species for effective aryl-alkyl cross-couplings. PMID:26266698

  10. Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound

    NASA Astrophysics Data System (ADS)

    El-Gamel, Nadia E. A.; Farghaly, Thoraya A.

    2013-11-01

    Cu(II) (1), Ni(II) (2), Cr(III) (3) and Fe(III) (4) complexes with 3-acetyl-4-benzoyl-1-phenyl-1H-pyrazole (L1) were prepared and structurally characterized. Usual coordination of L1 was achieved through nitrogen of pyrazole moiety and carbonyl acetyl group. Electronic spectra of the complexes indicate that the geometry of the metal center was six coordinate octahedral. In vitro antimicrobial activity of the ligand and complex compounds was screened in terms of antibacterial effect on Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative) and antifungal effect on the fungi Aspergillus flavus and candida albicans using the modified Kirby-Bauer disc diffusion and minimum inhibitory concentrations (MIC) methods. Ni(II) complex (2) exhibited remarkable antifungal inhibition against Candida albicans equal to the standard antifungal agent. To continue our study some structural modifications are formed by adding 4-fluoro-benzoyl moiety to L1 in different forms to produce different ligands, 3-acetyl-4-(4-flourobenzoyl)-1-phenyl-1H-pyrazole (L2) and 3-[(3-acetyl-1-phenyl-1H-4-pyrazolyl)carbonyl]-1-phenyl-4-(4-flourobenzoyl)-1H-pyrazole (L3), Ni complexes (5 and 6) are prepared and comparable in vitro antimicrobial study is evaluated. In vitro cytotoxicity of the Ni(II) complex (2) is studied using MTT assay. The analysis of the cell test showed that (2) displayed quite small cytotoxic response at the higher concentration level which indeed would further enable us for more opportunities in therapeutic and biomedical challenges. Both of the capability as a potent in vitro antifungal agent and the cell test analysis show Ni(II) complex (2) as a promising material in the translation of observed in vitro biological phenomenon into clinical therapies settings.

  11. 3-Methyl­sulfanyl-5-phenyl-4H-1,2,4-triazol-4-amine–water (6/1)

    PubMed Central

    Wu, Deng-Ze; Liu, Miao-Chang; Wu, Hua-Yue; Huang, Xiao-Bo; Li, Jian-Jun

    2009-01-01

    In the title compound, 6C9H10N4S·H2O, the dihedral angle between the five-membered triazole ring and the phenyl ring is 44.33 (16)°. The solvent water molecule is disordered about a special position with symmetry and its occupancy cannot be greater than 0.1667. The crystal structure is stabilized by inter­molecular N—H⋯N and C–H⋯N hydrogen bonds. PMID:21582420

  12. Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides.

    PubMed

    Daifuku, Stephanie L; Kneebone, Jared L; Snyder, Benjamin E R; Neidig, Michael L

    2015-09-01

    While previous studies have identified FeMes2(SciOPP) as the active catalyst species in iron-SciOPP catalyzed Kumada cross-coupling of mesitylmagnesium bromide and primary alkyl halides, the active catalyst species in cross-couplings with phenyl nucleophiles, where low valent iron species might be prevalent due to accessible reductive elimination pathways, remains undefined. In the present study, in situ Mössbauer and magnetic circular dichroism spectroscopic studies combined with inorganic syntheses and reaction studies are employed to evaluate the in situ formed iron species and identify the active catalytic species in iron-SciOPP catalyzed Suzuki-Miyaura and Kumada cross-couplings of phenyl nucleophiles and secondary alkyl halides. While reductive elimination to form Fe(η(6)-biphenyl)(SciOPP) occurs upon reaction of FeCl2(SciOPP) with phenyl nucleophiles, this iron(0) species is not found to be kinetically competent for catalysis. Importantly, mono- and bis-phenylated iron(II)-SciOPP species that form prior to reductive elimination are identified, where both species are found to be reactive toward electrophile at catalytically relevant rates. The higher selectivity toward the formation of cross-coupled product observed for the monophenylated species combined with the undertransmetalated nature of the in situ iron species in both Kumada and Suzuki-Miyaura reactions indicates that Fe(Ph)X(SciOPP) (X = Br, Cl) is the predominant reactive species in cross-coupling. Overall, these studies demonstrate that low-valent iron is not required for the generation of highly reactive species for effective aryl-alkyl cross-couplings.

  13. Supramolecular engineering through temperature-induced chemical modification of 2H-tetraphenylporphyrin on Ag(111): flat phenyl conformation and possible dehydrogenation reactions.

    PubMed

    Di Santo, Giovanni; Blankenburg, Stephan; Castellarin-Cudia, Carla; Fanetti, Mattia; Borghetti, Patrizia; Sangaletti, Luigi; Floreano, Luca; Verdini, Alberto; Magnano, Elena; Bondino, Federica; Pignedoli, Carlo A; Nguyen, Manh-Thuong; Gaspari, Roberto; Passerone, Daniele; Goldoni, Andrea

    2011-12-16

    Scratching the surface: Formation of a monolayer of 2H-tetraphenylporphyrins (2H-TPP) on Ag(111), either by sublimation of a multilayer in the range 525-600 K or by annealing (at the same temperature) a monolayer deposited at room temperature, induces a chemical modification of the molecules. Rotation of the phenyl rings into a flat conformation is observed and tentatively explained, by using DFT calculations, as a peculiar reaction due to molecular dehydrogenation.

  14. Iron(II) Active Species in Iron–Bisphosphine Catalyzed Kumada and Suzuki–Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides

    PubMed Central

    2015-01-01

    While previous studies have identified FeMes2(SciOPP) as the active catalyst species in iron–SciOPP catalyzed Kumada cross-coupling of mesitylmagnesium bromide and primary alkyl halides, the active catalyst species in cross-couplings with phenyl nucleophiles, where low valent iron species might be prevalent due to accessible reductive elimination pathways, remains undefined. In the present study, in situ Mössbauer and magnetic circular dichroism spectroscopic studies combined with inorganic syntheses and reaction studies are employed to evaluate the in situ formed iron species and identify the active catalytic species in iron–SciOPP catalyzed Suzuki–Miyaura and Kumada cross-couplings of phenyl nucleophiles and secondary alkyl halides. While reductive elimination to form Fe(η6-biphenyl)(SciOPP) occurs upon reaction of FeCl2(SciOPP) with phenyl nucleophiles, this iron(0) species is not found to be kinetically competent for catalysis. Importantly, mono- and bis-phenylated iron(II)–SciOPP species that form prior to reductive elimination are identified, where both species are found to be reactive toward electrophile at catalytically relevant rates. The higher selectivity toward the formation of cross-coupled product observed for the monophenylated species combined with the undertransmetalated nature of the in situ iron species in both Kumada and Suzuki–Miyaura reactions indicates that Fe(Ph)X(SciOPP) (X = Br, Cl) is the predominant reactive species in cross-coupling. Overall, these studies demonstrate that low-valent iron is not required for the generation of highly reactive species for effective aryl-alkyl cross-couplings. PMID:26266698

  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

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  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, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  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, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  18. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  19. 40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound...

  20. Discovery of 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine as a Potent I Kur Inhibitor.

    PubMed

    Finlay, Heather J; Johnson, James A; Lloyd, John L; Jiang, Ji; Neels, James; Gunaga, Prashantha; Banerjee, Abhisek; Dhondi, Naveen; Chimalakonda, Anjaneya; Mandlekar, Sandhya; Conder, Mary Lee; Sale, Harinath; Xing, Dezhi; Levesque, Paul; Wexler, Ruth R

    2016-09-01

    A new series of phenylquinazoline inhibitors of Kv 1.5 is disclosed. The series was optimized for Kv 1.5 potency, selectivity versus hERG, pharmacokinetic exposure, and pharmacodynamic potency. 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine (13k) was identified as a potent and ion channel selective inhibitor with robust efficacy in the preclinical rat ventricular effective refractory period (VERP) model and the rabbit atrial effective refractory period (AERP) model.

  1. Synthesis of 24-phenyl-24-oxo steroids derived from bile acids by palladium-catalyzed cross coupling with phenylboronic acid. NMR characterization and X-ray structures.

    PubMed

    Mayorquín-Torres, Martha C; Romero-Ávila, Margarita; Flores-Álamo, Marcos; Iglesias-Arteaga, Martin A

    2013-11-01

    Palladium-catalyzed cross coupling of phenyboronic acid with acetylated bile acids in which the carboxyl functions have been activated by formation of a mixed anhydride with pivalic anhydride afforded moderate to good yield of 24-phenyl-24-oxo-steroids. Unambiguous assignments of the NMR signals were made with the aid of combined 1D and 2D NMR techniques. X-ray diffraction studies confirmed the obtained structures.

  2. Sodium hydroxide catalyzed N-alkylation of (hetero) aromatic primary amines and N1,C5-dialkylation of 4-phenyl-2-aminothiazoles with benzyl alcohols.

    PubMed

    Donthiri, Ramachandra Reddy; Pappula, Venkatanarayana; Mohan, Darapaneni Chandra; Gaywala, Hiren H; Adimurthy, Subbarayappa

    2013-07-01

    In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.

  3. Crystal structure of (1S,2R)-6,6-dimethyl-4,8-dioxo-2-phenyl-spiro-[2.5]octane-1-carbaldehyde.

    PubMed

    Chelli, Saloua; Troshin, Konstantin; Lakhdar, Sami; Mayr, Herbert; Mayer, Peter

    2016-02-01

    In the title compound, C17H18O3, the two non-spiro C atoms of the cyclo-propane ring bear a formyl and a phenyl substituent which are trans-oriented. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π contacts resulting in a three-dimensional supra-molecular structure.

  4. Crystal structure and spectroscopic study on photochromism of 1,3-diphenyl-4-(4‧-fluoro)benzal-5-pyrazolone N(4)-phenyl semicarba-zone

    NASA Astrophysics Data System (ADS)

    Chai, Hui; Liu, Guangfei; Liu, Lang; Jia, Dianzeng; Guo, Zaiping; Lang, Jianping

    2005-10-01

    A novel compound 1,3-diphenyl-4-(4'-fluoro)benzal-5-pyrazolone N(4)-phenyl semicarbazone (DP4FBP-PSC) has been synthesized. X-ray single crystal structure analysis shows that the compound has interlaced structure linked by intermolecular hydrogen bonds. The results of fluorescence emission spectroscopy, UV-Vis reflection spectroscopy and the reaction rate constant indicate that DP4FBP-PSC is photochromic material. Its photochromic mechanism was investigated by structure analysis.

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 3,3â²,5,5â²-Tetra-methyl-bi-phenyl-4,4â²-diol. 721.1800 Section 721.1800 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1800...

  6. Heterocyclic glucocorticoid receptor modulators with a 2,2-dimethyl-3-phenyl-N-(thiazol or thiadiazol-2-yl)propanamide core.

    PubMed

    Xiao, Hai-Yun; Wu, Dauh-Rurng; Sheppeck, James E; Habte, Sium F; Cunningham, Mark D; Somerville, John E; Barrish, Joel C; Nadler, Steven G; Dhar, T G Murali

    2013-10-15

    A series of heterocyclic glucocorticoid receptor (GR) modulators with 2,2-dimethyl-3-phenyl-N-(thiazol or thiadiazol-2-yl)propanamide core are described. Structure-activity relationships suggest a combination of H-bond acceptor and a 4-fluorophenyl moiety as being important structural components contributing to the glucocorticoid receptor binding and functional activity for this series of GR modulators. PMID:24011644

  7. Synthesis and Characterization of Ferroelectric Liquid Crystalline Organosiloxanes Containing 4-(4-undecanyloxy bi-phenyl-1-carboxyloxy)phenyl (2S,3S)-2-chloro-3-methylvalerate and 4-(4-undecanyloxybenzoyloxy)biphenyl (2S,3S)-2-chloro-3-methylvalerate

    PubMed Central

    Lin, Chih-Hung

    2013-01-01

    A series of new organosiloxane ferroelectric liquid crystalline (FLC) materials have been synthesized, and their mesomorphic and physical properties have been characterized. Four new disiloxanes and trisiloxanes, containing biphenyl 4-hydroxybenzoate and phenyl 4-hydroxybiphenylcarboxylate as mesogenic units and eleven methylene unit as spacers and (2S,3S)-2-chloro-3-methylvalerate unit as chiral end groups. The molecule, using three phenyl ring as a mesogenic unit, formulates much wider liquid crystalline phase temperature ranges than that of a two phenyl ring unit. The phenyl arrangement differences of mesogenic unit result in the greater differences of the liquid crystal phase formation. The siloxane molecule induction is helpful to the more regular smectic phase formation and smectic phase stabilization, such as chiral SC (SC*) and SB phases. The siloxane molecule is helpful to reduce the phase transition temperature and broaden the liquid crystal temperature range of the SC* phase and, simultaneously, it will not induce chain crystallization phenomenon and dilute the Ps value. The synthesis and characterization of the new FLCs materials, which exhibit a room temperature SC* phase and higher spontaneous polarization are presented. PMID:24232576

  8. Morphology and structure of microcapsules prepared by interfacial polycondensation of methylene bis(phenyl isocyanate) with hexamethylene diamine.

    PubMed

    Jabbari, E

    2001-01-01

    Polyurea microcapsules containing 2- chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl) acetamide as the active agent were prepared by the method of interfacial polycondensation with methylene bis(phenyl isocyanate) the multifunctional isocyanatae, hexamethylene diamine as the diamine, and anionic (SLS) as the emulsifying sodium lignin liinin the agent. The internal structure and morphology of the microcapsules were examined with transmission electron microscopy. The microcapsules had a micro-reservoir structure in which the wall extended well into the core and the active agent was accomodated by the micro-reservoirs, distributed uniformly throughout the entire volume of a microcapsule. Based on the observed morphology, permeability of the water soluble monomer in the polyurea film and its solubility in the oil phase have a significant effect on the morphology and microstructure of the microcapsules. The multivalent salt, calcium chloride, plays a significant role in stabilizing the microcapsule structure, by interacting with the anionic surfactant SLS, and physically crosslinks the SLS chains, by interacting with the negatively charged carboxylic and phenolic groups, with subsequent phase separation of the physically crosslinked chains to form a concentrated gel phase. This gel phase encompasses the microcapsule, increases the stability, and modifies its release behaviour.

  9. Crystal structures and fungicidal activities of anti-2,4-bis(X-phenyl)pentane-2,4-diols

    NASA Astrophysics Data System (ADS)

    Jiao, Yinchun; Cao, Chenzhong; Zhao, Xiaolin

    2012-11-01

    The 1,3-diol moiety is present in a number of natural products and has some biological activity. Four symmetric anti-2,4-bis(X-phenyl)pentane-2,4-diols (a, X = p-F; b, X = p-CF3; c, X = m-OMe; d, X = m-CF3) have been characterized by X-ray diffraction, and the results indicated that the dihedral angles between the every two benzene rings in the systems are 34.38(10)°, 39.46(13)°, 23.42(7)°(A), 30.42(7)°(B) and 44.74(9)°, respectively. All of the structures were stabilized by classical intra- and intermolecular hydrogen bonding and some other weak interactions. It was observed that the hydrogen bonding patterns were formed between each single-molecule in compounds a-d, whereas H-bonding dimers were formed in the crystal lattices of both the anti- and syn-2,4-bisphenylpentane-2,4-diols. The four symmetric diaryl 1,3-diols were evaluated alongside several other 1,3-diols as potential antifungal agents, and their in vitro antifungal activities were measured against several fungal species, including Gibberella zeae, Botrytis cinerea, Alternaria alternata and Sclerotonia sclerotiorum.

  10. Phenyl Ether- and Aniline-Containing 2-Aminoquinolines as Potent and Selective Inhibitors of Neuronal Nitric Oxide Synthase.

    PubMed

    Cinelli, Maris A; Li, Huiying; Pensa, Anthony V; Kang, Soosung; Roman, Linda J; Martásek, Pavel; Poulos, Thomas L; Silverman, Richard B

    2015-11-12

    Excess nitric oxide (NO) produced by neuronal nitric oxide synthase (nNOS) is implicated in neurodegenerative disorders. As a result, inhibition of nNOS and reduction of NO levels is desirable therapeutically, but many nNOS inhibitors are poorly bioavailable. Promising members of our previously reported 2-aminoquinoline class of nNOS inhibitors, although orally bioavailable and brain-penetrant, suffer from unfavorable off-target binding to other CNS receptors, and they resemble known promiscuous binders. Rearranged phenyl ether- and aniline-linked 2-aminoquinoline derivatives were therefore designed to (a) disrupt the promiscuous binding pharmacophore and diminish off-target interactions and (b) preserve potency, isoform selectivity, and cell permeability. A series of these compounds was synthesized and tested against purified nNOS, endothelial NOS (eNOS), and inducible NOS (iNOS) enzymes. One compound, 20, displayed high potency, selectivity, and good human nNOS inhibition, and retained some permeability in a Caco-2 assay. Most promisingly, CNS receptor counterscreening revealed that this rearranged scaffold significantly reduces off-target binding.

  11. Novel 1-Phenyl-3-hydroxy-4-pyridinone Derivatives as Multifunctional Agents for the Therapy of Alzheimer's Disease.

    PubMed

    Sheng, Rong; Tang, Li; Jiang, Liu; Hong, Lingjuan; Shi, Ying; Zhou, Naiming; Hu, Yongzhou

    2016-01-20

    A series of novel 1-phenyl-3-hydroxy-4-pyridinone derivatives were designed and synthesized as multifunctional agents for Alzheimer's disease (AD) therapy through incorporation of 3-hydroxy-4-pyridinone moiety from deferiprone into the scaffold of H3 receptor antagonists. Most of these new compounds displayed designed quadruple functions, H3 receptor antagonism, Aβ aggregation inhibition, metal ion chelation, and radical scavenging. Especially, the most promising compound 5c displayed nanomolar IC50 values in H3 receptor antagonism with high selectivity, efficient capability to interrupt the formation of Aβ(1-42) fibrils, good copper and iron chelating properties, and more potent 2,2'-azino-bis(3-ethyl-benzothiazoline-6-sulfonic acid) radical cation (ABTS(•+)) scavenging activity than Trolox. Further biological evaluation revealed that it did not show obvious cytotoxicity and hERG potassium channel inhibition at micromolar concentration. In addition, compound 5c demonstrated suitable pharmacokinetic properties and acceptable blood-brain barrier (BBB) permeability in vivo. All these results indicate that compound 5c is a potential multifunctional candidate for AD therapy. PMID:26479744

  12. 3, 4-dihydroxyl-phenyl lactic acid restores NADH dehydrogenase 1 α subunit 10 to ameliorate cardiac reperfusion injury.

    PubMed

    Yang, Xiao-Yuan; He, Ke; Pan, Chun-Shui; Li, Quan; Liu, Yu-Ying; Yan, Li; Wei, Xiao-Hong; Hu, Bai-He; Chang, Xin; Mao, Xiao-Wei; Huang, Dan-Dan; Wang, Li-Jun; Hu, Shui-Wang; Jiang, Yong; Wang, Guo-Cheng; Fan, Jing-Yu; Fan, Tai-Ping; Han, Jing-Yan

    2015-01-01

    The present study aimed to detect the role of 3, 4-dihydroxyl-phenyl lactic acid (DLA) during ischemia/reperfusion (I/R) induced myocardial injury with emphasis on the underlying mechanism of DLA antioxidant. Male Spragu-Dawley (SD) rats were subjected to left descending artery occlusion followed by reperfusion. Treatment with DLA ameliorated myocardial structure and function disorder, blunted the impairment of Complex I activity and mitochondrial function after I/R. The results of 2-D fluorescence difference gel electrophoresis revealed that DLA prevented the decrease in NDUFA10 expression, one of the subunits of Complex I. To find the target of DLA, the binding affinity of Sirtuin 1 (SIRT1) to DLA and DLA derivatives with replaced two phenolic hydroxyls was detected using surface plasmon resonance and bilayer interferometry. The results showed that DLA could activate SIRT1 after I/R probably by binding to this protein, depending on phenolic hydroxyl. Moreover, the importance of SIRT1 to DLA effectiveness was confirmed through siRNA transfection in vitro. These results demonstrated that DLA was able to prevent I/R induced decrease in NDUFA10 expression, improve Complex I activity and mitochondrial function, eventually attenuate cardiac structure and function injury after I/R, which was possibly related to its ability of binding to and activating SIRT1. PMID:26030156

  13. Adsorption of the enantiomers of 3-chloro-1-phenyl-propanol on silica-bonded chiral quinidine carbamate

    SciTech Connect

    Asnin, Leonid; Kaczmarski, Krzysztof; Felinger, Attila; Gritti, Fabrice; Guiochon, Georges A

    2005-10-01

    The interactions of 3-chloro-1-phenyl-propanol with a quinidine carbamate-bonded chiral stationary phase under NPLC conditions were studied by measuring the adsorption isotherm data of its enantiomers by frontal analysis, modeling these data with a suitable isotherm model, and comparing the experimental overloaded elution band profiles with those calculated with this isotherm and the equilibrium dispersive model of liquid chromatography. The affinity energy distribution was calculated from the adsorption isotherm data. The results show that the surface of the adsorbent is heterogeneous and exhibits a bimodal adsorption energy distribution. This fact is interpreted in terms of the presence of two different types of adsorption sites on the stationary phase, nonselective and enantioselective sites. Albeit the bi-Langmuir isotherm model successfully accounts for the single-component data corresponding to both enantiomers, the competitive bi-Langmuir isotherm model does not allow an accurate prediction of the overloaded band profiles of the racemic mixture. Thermodynamic data are drawn for explanation. Some aspects of the retention mechanism are discussed in the light of the data obtained.

  14. Measurement of Large Dipolar Couplings of a Liquid Crystal with Terminal Phenyl Rings and Estimation of the Order Parameters.

    PubMed

    Kumar, R V Sudheer; Ramanathan, Krishna V

    2015-07-20

    NMR spectroscopy is a powerful means of studying liquid-crystalline systems at atomic resolutions. Of the many parameters that can provide information on the dynamics and order of the systems, (1) H-(13) C dipolar couplings are an important means of obtaining such information. Depending on the details of the molecular structure and the magnitude of the order parameters, the dipolar couplings can vary over a wide range of values. Thus the method employed to estimate the dipolar couplings should be capable of estimating both large and small dipolar couplings at the same time. For this purpose, we consider here a two-dimensional NMR experiment that works similar to the insensitive nuclei enhanced by polarization transfer (INEPT) experiment in solution. With the incorporation of a modification proposed earlier for experiments with low radio frequency power, the scheme is observed to enable a wide range of dipolar couplings to be estimated at the same time. We utilized this approach to obtain dipolar couplings in a liquid crystal with phenyl rings attached to either end of the molecule, and estimated its local order parameters. PMID:26014117

  15. Electronic structure mapping of branching states in poly[methyl(phenyl)silane] upon exposure to UV radiation

    NASA Astrophysics Data System (ADS)

    Schauer, František; Tkáč, Lukáš; Ožvoldová, Miroslava; Nadáždy, Vojtech; Gmucová, Katarána; Végsö, Karol; Tkáčová, Miroslava; Chlpík, Juraj

    2016-02-01

    The origin of white photoluminescence in polysilanes has long been disputed, and this emission is closely connected with information recording in nanotechnologies. We elucidated UV degradation of an archetypal model polymer poly[methyl(phenyl)silane] by using a new method for electronic structure mapping of organic semiconductors, energy-resolved electrochemical impedance spectroscopy (ER-EIS) and photoluminescence spectroscopy. UV exposure at 345 nm resulted in two defect bands above the highest occupied molecular orbital (HOMO) in the energy region from -5.5 eV to -3.5 eV with respect to the zero vacuum energy level. The respective density of states was 1016 - 1017 cm-3eV-1, and the total integrated concentration was 0 - 1017 cm-3. The photoluminescence in the long-wavelength region gave wide bands with photon energies from 2.2 eV to 3.2 eV (corresponding to wavelengths from 600 nm to 390 nm). The observed bands were interpreted by assuming the formation of energetically distributed Si branching radiative states, whose distribution in the HOMO - lowest unoccupied molecular orbital (LUMO) gap was observed by using ER-EIS. The quantum efficiency of defect state formation increased from Φ(x)345 nm = 0.0045 to Φ(x)290 nm = 0.053. The obtained results may contribute to the production of effective polysilane nanomasks and to information recording.

  16. Strategies for enhancing the production of penicillin G acylase from Bacillus badius: influence of phenyl acetic acid dosage.

    PubMed

    Rajendran, Karthikeyan; Mahadevan, Surianarayanan; Jeyaprakash, Rajendhran; Paramasamy, Gunasekaran; Mandal, Asit Baran

    2013-11-01

    Bacillus badius isolated from soil has been identified as potential producer of penicillin G acylase (PGA). In the present study, batch experiments performed at optimized inoculum size, temperature, pH, and agitation yielded a maximum PGA of 9.5 U/ml in shake flask. The experiments conducted in bioreactor with different oxygen flow rates revealed that 0.66 vvm oxygen flow rate could be sufficient for the maximum PGA activity of 12.7 U/ml. From a detailed investigation on the strategies of the addition of phenyl acetic acid (PAA) for increasing the production of PGA, it was found that the controlled addition of 10 ml of 0.1 % (w/v) PAA once in every 2 h from 6th hour of growth showed the maximum PGA activity of 32 U/ml. Thus, our studies for the first time showed that at concentration above 0.1 % (w/v) PAA, the PGA production decreased. This selective condition paves the way for less costly bioprocess for the production of PGA. PMID:23949729

  17. Optimization of antiproliferative activity of substituted phenyl 4-(2-oxoimidazolidin-1-yl) benzenesulfonates: QSAR and CoMFA analyses.

    PubMed

    Masand, Vijay H; Mahajan, Devidas T; Alafeefy, Ahmed M; Bukhari, Syed Nasir Abbas; Elsayed, Nahed N

    2015-09-18

    Multiple separate quantitative structure-activity relationships (QSARs) models were built for the antiproliferative activity of substituted Phenyl 4-(2-Oxoimidazolidin-1-yl)-benzenesulfonates (PIB-SOs). A variety of descriptors were considered for PIB-SOs through QSAR model building. Genetic algorithm (GA), available in QSARINS, was employed to select optimum number and set of descriptors to build the multi-linear regression equations for a dataset of PIB-SOs. The best three parametric models were subjected to thorough internal and external validation along with Y-randomization using QSARINS, according to the OECD principles for QSAR model validation. The models were found to be statistically robust with high external predictivity. The best three parametric model, based on steric, 3D- and finger print descriptors, was found to have R(2)=0.91, R(2)ex=0.89, and CCCex=0.94. The CoMFA model, which is based on a combination of steric and electrostatic effects and graphically inferred using contour plots, gave F=229.34, R(2)CV=0.71 and R(2)=0.94. Steric repulsion, frequency of occurrence of carbon and nitrogen at topological distance of seven, and internal electronic environment of the molecule were found to have correlation with the anti-tumor activity of PIB-SOs. PMID:26066412

  18. Novel 1-Phenyl-3-hydroxy-4-pyridinone Derivatives as Multifunctional Agents for the Therapy of Alzheimer's Disease.

    PubMed

    Sheng, Rong; Tang, Li; Jiang, Liu; Hong, Lingjuan; Shi, Ying; Zhou, Naiming; Hu, Yongzhou

    2016-01-20

    A series of novel 1-phenyl-3-hydroxy-4-pyridinone derivatives were designed and synthesized as multifunctional agents for Alzheimer's disease (AD) therapy through incorporation of 3-hydroxy-4-pyridinone moiety from deferiprone into the scaffold of H3 receptor antagonists. Most of these new compounds displayed designed quadruple functions, H3 receptor antagonism, Aβ aggregation inhibition, metal ion chelation, and radical scavenging. Especially, the most promising compound 5c displayed nanomolar IC50 values in H3 receptor antagonism with high selectivity, efficient capability to interrupt the formation of Aβ(1-42) fibrils, good copper and iron chelating properties, and more potent 2,2'-azino-bis(3-ethyl-benzothiazoline-6-sulfonic acid) radical cation (ABTS(•+)) scavenging activity than Trolox. Further biological evaluation revealed that it did not show obvious cytotoxicity and hERG potassium channel inhibition at micromolar concentration. In addition, compound 5c demonstrated suitable pharmacokinetic properties and acceptable blood-brain barrier (BBB) permeability in vivo. All these results indicate that compound 5c is a potential multifunctional candidate for AD therapy.

  19. A novel synthetic 1,3-phenyl bis-thiourea compound targets microtubule polymerization to cause cancer cell death.

    PubMed

    Shing, Jennifer C; Choi, Jae Won; Chapman, Robert; Schroeder, Mark A; Sarkaria, Jann N; Fauq, Abdul; Bram, Richard J

    2014-07-01

    Microtubules are essential cytoskeletal components with a central role in mitosis and have been particularly useful as a cancer chemotherapy target. We synthesized a small molecule derivative of a symmetrical 1,3-phenyl bis-thiourea, (1,1'-[1,3-phenylene]bis[3-(3,5-dimethylphenyl)thiourea], named "41J"), and identified a potent effect of the compound on cancer cell survival. 41J is cytotoxic to multiple cancer cell lines at nanomolar concentrations. Cell death occurred by apoptosis and was preceded by mitotic arrest in prometaphase. Prometaphase arrest induced by 41J treatment was accompanied by dissociation of cyclin B1 levels from the apparent mitotic stage and by major spindle abnormalities. Polymerization of purified tubulin in vitro was directly inhibited by 41J, suggesting that the compound works by directly interfering with microtubule function. Compound 41J arrested the growth of glioblastoma multiforme xenografts in nude mice at doses that were well-tolerated, demonstrating a relatively specific antitumor effect. Importantly, 41J overcame drug resistance due to β-tubulin mutation and P-glycoprotein overexpression. Compound 41J may serve as a useful new lead compound for anticancer therapy development. PMID:24755487

  20. Electron angular distributions and attachment rates in o-Benzyne and Phenyl aromatic molecules: the effect of the permanent dipoles

    NASA Astrophysics Data System (ADS)

    Carelli, Fabio; Gianturco, Franco A.

    2013-12-01

    Free, gas-phase polycyclic aromatic hydrocarbons (PAHs) and related species are currently considered to play an important role in the interstellar/circumstellar medium as they are thought to significantly contribute to both Diffuse and Unidentified infrared interstellar bands. They are also considered fundamental blocks of the interstellar dust and several formation mechanisms were proposed with regard to their interstellar/circumstellar synthesis. In this paper we therefore present and discuss the results obtained from ab initio quantum scattering calculations of the response from neutral polar aromatic single-ring species to low-energies electron collisions. Our main purpose is here to provide new values for the rate constants for electron attachment to orthobenzyne and to phenyl molecules by discussing in detail the effects of the long-range dipole interaction in the framework of the Born perturbative approximation at the first order. We shall further discuss the specific behavior of the electrons' diffusion by such molecules, especially in the low-energy range of the scattered particles' energies as guided by their permanent dipole moments. We shall also provide accurate numerical fittings for both rates and give explicitly the fitting parameters for their possible use in evolutionary models.

  1. Conformation and tautomerism of methoxy-substituted 4-phenyl-4-thiazoline-2-thiones: a combined crystallographic and ab initio investigation.

    PubMed

    Balti, Monaem; Norberg, Bernadette; Efrit, Mohamed Lotfi; Lanners, Steve; Wouters, Johan

    2016-05-01

    4-Phenyl-4-thiazoline-2-thiol is an active pharmaceutical compound, one of whose activities is as a human indolenamine dioxygenase inhibitor. It has been shown recently that in both the solid state and the gas phase, the thiazolinethione tautomer should be preferred. As part of both research on this lead compound and a medicinal chemistry program, a series of substituted arylthiazolinethiones have been synthesized. The molecular conformations and tautomerism of 4-(2-methoxyphenyl)-4-thiazoline-2-thione and 4-(4-methoxyphenyl)-4-thiazoline-2-thione, both C10H9NOS2, are reported and compared with the geometry deduced from ab initio calculations [PBE/6-311G(d,p)]. Both the crystal structure analyses and the calculations establish the thione tautomer for the two substituted arylthiazolinethiones. In the crystal structure of the 2-methoxyphenyl regioisomer, the thiazolinethione unit was disordered over two conformations. Both isomers exhibit similar hydrogen-bond patterns [R2(2)(8) motif] and form dimers. The crystal packing is further reinforced by short S...S interactions in the 2-methoxyphenyl isomer. The conformations of the two regioisomers correspond to stable geometries calculated from an ab initio energy-relaxed scan. PMID:27146572

  2. Pharmacologic Evaluation of Antidepressant Activity and Synthesis of 2-Morpholino-5-phenyl-6H-1,3,4-thiadiazine Hydrobromide.

    PubMed

    Sarapultsev, Alexey P; Chupakhin, Oleg N; Sarapultsev, Petr A; Sidorova, Larisa P; Tseitler, Tatiana A

    2016-01-01

    Substituted thiadiazines exert a reliable therapeutic effect in treating stress, and a schematic description of their ability to influence all aspects of a stress response has been depicted. This study was conducted to pharmacologically evaluate compound L-17, a substituted thiadiazine, (2-morpholino-5-phenyl-6H-1,3,4-thiadiazine, hydrobromide) for possible anti-psychotic/antidepressant activity. Compound L-17 was synthesized by cyclocondensation of α-bromoacetophenone with the original morpholine-4-carbothionic acid hydrazide. Pharmacologic evaluations were conducted using methods described by E.F. Lavretskaya (1985), and in accordance with published guidelines for studying drugs for neuroleptic activity. Compound L-17 was evaluated for various possible mechanisms of action, including its effects on cholinergic system agonists/antagonists, dopaminergic neurotransmission, the adrenergic system, and 5-HT3 serotonin receptors. One or more of these mechanisms may be responsible for the beneficial effects shown by thiadiazine compounds in experiments conducted to evaluate their activity in models of acute stress and acute myocardial infarction. PMID:27213404

  3. Experimental and molecular modeling investigation of (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide

    NASA Astrophysics Data System (ADS)

    Özdemir, Namık; Dayan, Serkan; Dayan, Osman; Dinçer, Muharrem; Kalaycıoğlu, Nilgün Ö.

    2013-03-01

    The Schiff base compound (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide has been synthesized and characterized by IR, NMR and Uv-vis spectroscopies, and single-crystal X-ray diffraction technique. In addition, quantum chemical calculations employing density functional theory (DFT) method with the 6-311++G(d,p) basis set were performed to study the molecular, spectroscopic and some electronic structure properties of the title compound, and the results were compared with the experimental findings. There exists a good correlation between experimental and theoretical data. Enol-imine/keto-amine tautomerization mechanism was investigated in the gas phase and in solution phase using the polarizable continuum model (PCM) approximation. The energetic and thermodynamic parameters of the enol-imine → keto-amine transfer process show that the single proton exchange is thermodynamically unfavored both in the gas phase and in solution phase. However, the reverse reaction seems to be feasible with a low barrier height and is supported by negative values in enthalpy and free energy changes both in the gas phase and in solution phase. The solvent effect is found to be sizable with increasing polarity of the solvents for the reverse reaction. The predicted nonlinear optical properties of the compound are found to be much greater than those of urea.

  4. Natural bond orbital analysis, electronic structure and vibrational spectral analysis of N-(4-hydroxyl phenyl) acetamide: a density functional theory.

    PubMed

    Govindasamy, P; Gunasekaran, S; Ramkumaar, G R

    2014-09-15

    The Fourier transform infrared (FT-IR) and FT-Raman spectra of N-(4-hydroxy phenyl) acetamide (N4HPA) of painkiller agent were recorded in the region 4000-450 cm(-1) and 4000-50 cm(-1) respectively. Density functional theory (DFT) has been used to calculate the optimized geometrical parameter, atomic charges, and vibrational wavenumbers and intensity of the vibrational bands. The computed vibrational wave numbers were compared with the FT-IR and FT-Raman experimental data. The computational calculations at DFT/B3LYP level with 6-31G(d,p), 6-31++G(d,p), 6-311G(d,p) and 6-311++G(d,p) basis sets. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using Vibrational energy distribution analysis (VEDA 4) program. The oscillator's strength calculated by TD-DFT and N4HPA is approach complement with the experimental findings. The NMR chemical shifts 13C and 1H were recorded and calculated using the gauge independent atomic orbital (GIAO) method. The molecular electrostatic potential (MESP) and electron density surfaces of the molecule were constructed. The Natural charges and intermolecular contacts have been interpreted using Natural Bond orbital (NBO) analysis the HOMO-LUMO energy gap has been calculated. The thermodynamic properties like entropy, heat capacity and zero vibrational energy have been calculated.

  5. Pharmacologic Evaluation of Antidepressant Activity and Synthesis of 2-Morpholino-5-phenyl-6H-1,3,4-thiadiazine Hydrobromide

    PubMed Central

    Sarapultsev, Alexey P.; Chupakhin, Oleg N.; Sarapultsev, Petr A.; Sidorova, Larisa P.; Tseitler, Tatiana A.

    2016-01-01

    Substituted thiadiazines exert a reliable therapeutic effect in treating stress, and a schematic description of their ability to influence all aspects of a stress response has been depicted. This study was conducted to pharmacologically evaluate compound L-17, a substituted thiadiazine, (2-morpholino-5-phenyl-6H-1,3,4-thiadiazine, hydrobromide) for possible anti-psychotic/antidepressant activity. Compound L-17 was synthesized by cyclocondensation of α-bromoacetophenone with the original morpholine-4-carbothionic acid hydrazide. Pharmacologic evaluations were conducted using methods described by E.F. Lavretskaya (1985), and in accordance with published guidelines for studying drugs for neuroleptic activity. Compound L-17 was evaluated for various possible mechanisms of action, including its effects on cholinergic system agonists/antagonists, dopaminergic neurotransmission, the adrenergic system, and 5-HT3 serotonin receptors. One or more of these mechanisms may be responsible for the beneficial effects shown by thiadiazine compounds in experiments conducted to evaluate their activity in models of acute stress and acute myocardial infarction. PMID:27213404

  6. Observation of transient alignment-inversion walls in nematics of phenyl benzoates in the presence of a magnetic field.

    PubMed

    Hinov, Hristo P; Vistin', Leonard K; Marinov, Yordan G

    2014-04-17

    Formation of new transient walls by a constant magnetic field at the Fréedericsz critical value has been observed. They are oriented along the initial alignment of the nematic phase of phenyl benzoates and appeared only in relatively thick samples with a thickness between 50 and 100 μm of the cells. The excellent planarity of the liquid crystal orientation is considered to be the most important condition for their presence These magnetic walls are transient as they disappear either after a few seconds for 100 μm thick nematic cells or after parts of a second for thinner (50 μm) nematic cells. Nonregular stable magnetic walls, incorporating disclinations with core, appear immediately after the relaxation of the transient walls, when the planarity of the nematic orientation is not perfect. In thinner nematic cells of 20 μm or less, a Fréedericksz transition has only been observed. The formation of transient magnetic walls can be described by a model taking into account alignment-inversion, twisted along Y regions. The transient walls accompanied by a system of Becke lines relax by going through three-dimensional twist-splay-bend deformations. PMID:24670039

  7. Palladium(II) complexes of OS donor N-(di(butyl/phenyl)carbamothioyl)benzamide and their antiamoebic activity.

    PubMed

    Maurya, Mannar R; Uprety, Bhawna; Avecilla, Fernando; Tariq, Saba; Azam, Amir

    2015-06-15

    Two promising palladium(II) compounds of general formula, cis-[Pd(L-O,S)2] [where HL-O,S = N-(di(butyl/phenyl)carbamothioyl)benzamide] as metal based antiamoebic drug candidates, have been synthesized. Both complexes are characterized in the solid state by FT-IR spectroscopy, TGA and single crystal X-ray study, as well as in solution by other spectroscopic techniques such as (1)H and (13)C NMR, and UV-visible. All these studies confirm the coordination of ligands through oxygen and sulphur atoms upon thioenolization induced delocalization. Complexes adopt cis-configuration in the solid state. Both the complexes and their respective ligands were screened in vitro for antiamoebic activity against HM1:1MSS strain of Entamoeba histolytica by microdilution method and cell viability in response to drugs was checked by using MTT assay. The IC50 values in the range 0.30-0.80 μM for ligands as well as complexes compared to 1.40 for metronidazole along with their similar inhibitory effect on cell viability of HEK293 cells like metronidazole make them promising future antiamoebic drugs.

  8. Reactivity of superoxide radical anion and hydroperoxyl radical with alpha-phenyl-N-tert-butylnitrone (PBN) derivatives.

    PubMed

    Durand, Grégory; Choteau, Fanny; Pucci, Bernard; Villamena, Frederick A

    2008-12-01

    Nitrones have exhibited pharmacological activity against radical-mediated pathophysiological conditions and as analytical reagents for the identification of transient radical species by electron paramagnetic resonance (EPR) spectroscopy. In this work, competitive spin trapping, stopped-flow kinetics, and density functional theory (DFT) were employed to assess and predict the reactivity of O(2)(*-) and HO(2)(*) with various para-substituted alpha-phenyl-N-tert-butylnitrone (PBN) spin traps. Rate constants of O(2)(*-) trapping by nitrones were determined using competitive UV-vis stopped-flow method with phenol red (PR) as probe, while HO(2)(*) trapping rate constants were calculated using competition kinetics with 5,5-dimethylpyrroline N-oxide (DMPO) by employing EPR spectroscopy. The effects of the para substitution on the charge density of the nitronyl-carbon and on the free energies of nitrone reactivity with O(2)(*-) and HO(2)(*) were computationally rationalized at the PCM/B3LYP/6-31+G(d,p)//B3LYP/6-31G(d) level of theory. Theoretical and experimental data show that the rate of O(2)(*-) addition to PBN derivatives is not affected by the polar effect of the substituents. However, the reactivity of HO(2)(*) follows the Hammett equation and is increased as the substituent becomes more electron withdrawing. This supports the conclusion that the nature of HO(2)(*) addition to PBN derivatives is electrophilic, while the addition of O(2)(*-) to PBN-type compounds is only weakly electrophilic. PMID:18998656

  9. Phenyl mercuric acetate (PMA): mercury-bearing flexible gymnasium floors in schools--evaluation of hazards and controlled abatement.

    PubMed

    Beaulieu, Harry J; Beaulieu, Serrita; Brown, Chris

    2008-06-01

    Phenyl mercuric acetate (PMA) historically has been used as a catalyst in polyurethane systems. In the 1950s-1970s, PMA was used as a catalyst in the 3M Tartan brand polyurethane flexible floors that were installed commonly in school gymnasiums. Mercury vapor is released into air above the surface of these floors. Sampling mercury in bulk flooring material and mercury vapor in air was conducted in nine Idaho schools in the spring of 2006. These evaluations were conducted in response to concerns by school officials that the floors could contain mercury and could release the mercury vapor into the air, presenting a potential health hazard for students, staff, and visitors. Controlled abatement was conducted in one school where remodeling would impact the mercury-bearing flexible gym floors ( approximately 9,000 ft(2) total). The controlled abatement consisted of containment of the work area with negative air technology; worker protection, including mercury-specific training, use of personal protective equipment, and biological and exposure monitoring; and environmental protection, including proper disposal of mercury-bearing hazardous waste material. PMID:18365889

  10. Phenyl mercuric acetate (PMA): mercury-bearing flexible gymnasium floors in schools--evaluation of hazards and controlled abatement.

    PubMed

    Beaulieu, Harry J; Beaulieu, Serrita; Brown, Chris

    2008-06-01

    Phenyl mercuric acetate (PMA) historically has been used as a catalyst in polyurethane systems. In the 1950s-1970s, PMA was used as a catalyst in the 3M Tartan brand polyurethane flexible floors that were installed commonly in school gymnasiums. Mercury vapor is released into air above the surface of these floors. Sampling mercury in bulk flooring material and mercury vapor in air was conducted in nine Idaho schools in the spring of 2006. These evaluations were conducted in response to concerns by school officials that the floors could contain mercury and could release the mercury vapor into the air, presenting a potential health hazard for students, staff, and visitors. Controlled abatement was conducted in one school where remodeling would impact the mercury-bearing flexible gym floors ( approximately 9,000 ft(2) total). The controlled abatement consisted of containment of the work area with negative air technology; worker protection, including mercury-specific training, use of personal protective equipment, and biological and exposure monitoring; and environmental protection, including proper disposal of mercury-bearing hazardous waste material.

  11. Dextromethorphan prevents the diethyldithiocarbamate enhancement of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine toxicity in mice.

    PubMed

    Vaglini, Francesca; Pardini, Carla; Bonuccelli, Ubaldo; Maggio, Roberto; Corsini, Giovanni U

    2003-05-30

    In this report we show that dextromethorphan, a non-opioid cough suppressant, prevents the neurodegeneration of dopaminergic neurons in the substantia nigra of mice treated with diethyldithiocarbamate (DDC) and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). This effect is further substantiated by the assessment of dopamine (DA) content in the striatum of these animals. Dextromethorphan does not attenuate the striatal DA fall induced by MPTP alone but completely prevents DDC-induced enhancement after the combined treatment. Moreover, a study of DA metabolites has confirmed this neuroprotective property. The striatal levels of serotonin, which were studied as a control neuronal marker, did not change with any of the treatments administered. Furthermore, we show that dextromethorphan reduces the toxicity of glutamate against dopamine neurons in mesencephalic cell cultures. In line with previous data suggesting that dextromethorphan can prevent neuronal damage, our observations supply new evidence regarding the possibility of this compound being of therapeutic use in neurodegenerative diseases. PMID:12738074

  12. Growth and characterization of benzaldehyde 4-nitro phenyl hydrazone (BPH) single crystal: A proficient second order nonlinear optical material

    NASA Astrophysics Data System (ADS)

    Saravanan, M.; Abraham Rajasekar, S.

    2016-04-01

    The crystals (benzaldehyde 4-nitro phenyl hydrazone (BPH)) appropriate for NLO appliance were grown by the slow cooling method. The solubility and metastable zone width measurement of BPH specimen was studied. The material crystallizes in the monoclinic crystal system with noncentrosymmetric space group of Cc. The optical precision in the whole visible region was found to be excellent for non-linear optical claim. Excellence of the grown crystal is ascertained by the HRXRD and etching studies. Laser Damage Threshold and Photoluminescence studies designate that the grown crystal contains less imperfection. The mechanical behaviour of BPH sample at different temperatures was investigated to determine the hardness stability of the grown specimen. The piezoelectric temperament and the relative Second Harmonic Generation (for diverse particle sizes) of the material were also studied. The dielectric studies were executed at varied temperatures and frequencies to investigate the electrical properties. Photoconductivity measurement enumerates consummate of inducing dipoles due to strong incident radiation and also divulge the nonlinear behaviour of the material. The third order nonlinear optical properties of BPH crystals were deliberate by Z-scan method.

  13. Anti-parkinsonian effects of octacosanol in 1-methyl-4-phenyl-1,2,3,6 tetrahydropyridine-treated mice☆

    PubMed Central

    Wang, Tao; Liu, Yanyong; Yang, Nan; Ji, Chao; Chan, Piu; Zuo, Pingping

    2012-01-01

    Our previous research showed that octacosanol exerted its protective effects in 6-hydroxydopamine-induced Parkinsonian rats. The goal of this study was to investigate whether octacosanol would attenuate neurotoxicity in 1-methyl-4-phenyl-1,2,3,6 tetrahydropyridine (MPTP)-treated C57BL/6N mice and its potential mechanism. Behavioral tests, tyrosine hydroxylase immunohistochemistry and western blot were used to investigate the effects of octacosanol in a mouse model of Parkinson's disease. Oral administration of octacosanol (100 mg/kg) significantly improved behavioral impairments in mice treated by MPTP and markedly ameliorated morphological appearances of tyrosine hydroxylase-positive neuronal cells in the substantia nigra. Furthermore, octacosanol blocked MPTP-induced phosphorylation of p38MAPK and JNK, but not ERK1/2. These findings implicated that the protective effects afforded by octacosanol might be mediated by blocking the phosphorylation of p38MAPK and JNK on the signal transduction in vivo. Considering its excellent tolerability, octacosanol might be considered as a candidate agent for clinical application in treating Parkinson's disease. PMID:25722698

  14. Identification of 2-[4-[(4-Methoxyphenyl)methoxy]-phenyl]acetonitrile and Derivatives as Potent Oct3/4 Inducers.

    PubMed

    Cheng, Xinlai; Dimou, Eleni; Alborzinia, Hamed; Wenke, Frank; Göhring, Axel; Reuter, Stefanie; Mah, Nancy; Fuchs, Heiko; Andrade-Navarro, Miguel A; Adjaye, James; Gul, Sheraz; Harms, Christoph; Utikal, Jochen; Klipp, Edda; Mrowka, Ralf; Wölfl, Stefan

    2015-06-25

    Reprogramming somatic cells into induced-pluripotent cells (iPSCs) provides new access to all somatic cell types for clinical application without any ethical controversy arising from the use of embryonic stem cells (ESCs). Established protocols for iPSCs generation based on viral transduction with defined factors are limited by low efficiency and the risk of genetic abnormality. Several small molecules have been reported as replacements for defined transcriptional factors, but a chemical able to replace Oct3/4 allowing the generation of human iPSCs is still unavailable. Using a cell-based High Throughput Screening (HTS) campaign, we identified that 2-[4-[(4-methoxyphenyl)methoxy]phenyl]acetonitrile (1), termed O4I1, enhanced Oct3/4 expression. Structural verification and modification by chemical synthesis showed that O4I1 and its derivatives not only promoted expression and stabilization of Oct3/4 but also enhanced its transcriptional activity in diverse human somatic cells, implying the possible benefit from using this class of compounds in regenerative medicine. PMID:25898186

  15. Poly(vinyl chloride) blend with biodegradable cellulose acetate in presence of N-(phenyl amino) maleimides.

    PubMed

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

    2014-09-01

    Wider plastic applications of poly(vinyl chloride) (PVC) has raised serious problem to the environment. Since (PVC) waste products resist biodegradation and persist in the environment for longer time. The object of this study is to blend (PVC) with biodegradable cellulose acetate to thermally support the polymer during the molding process as well as to enhance the biodegradability of (PVC) waste products. Blending of poly(vinyl chloride) and cellulose acetate (CA) in presence of N-(phenyl amino) maleimides (R-PhAM) where (R=H, 4-NO2) led to improvement in the thermal stability of the blend film at high temperatures as shown from the high values of initial decomposition temperature (To) determined from their thermogravimetry (TG) curves. Also, blending (PVC) with (CA) led to improvement in the mechanical properties of the blend films as compared to (PVC). The crystalline regions of cellulose acetate enhanced the elasticity of the blend films as shown from their high Young's modulus values.

  16. Reduced Photoinhibition under Low Irradiance Enhanced Kacip Fatimah (Labisia pumila Benth) Secondary Metabolites, Phenyl Alanine Lyase and Antioxidant Activity

    PubMed Central

    Ibrahim, Mohd Hafiz; Jaafar, Hawa Z.E.

    2012-01-01

    A randomized complete block design experiment was designed to characterize the relationship between production of total flavonoids and phenolics, anthocyanin, photosynthesis, maximum efficiency of photosystem II (Fv/Fm), electron transfer rate (Fm/Fo), phenyl alanine lyase activity (PAL) and antioxidant (DPPH) in Labisia pumila var. alata, under four levels of irradiance (225, 500, 625 and 900 μmol/m2/s) for 16 weeks. As irradiance levels increased from 225 to 900 μmol/m2/s, the production of plant secondary metabolites (total flavonoids, phenolics and antocyanin) was found to decrease steadily. Production of total flavonoids and phenolics reached their peaks under 225 followed by 500, 625 and 900 μmol/m2/s irradiances. Significant positive correlation of production of total phenolics, flavonoids and antocyanin content with Fv/Fm, Fm/Fo and photosynthesis indicated up-regulation of carbon-based secondary metabolites (CBSM) under reduced photoinhibition on the under low light levels condition. At the lowest irradiance levels, Labisia pumila extracts also exhibited a significantly higher antioxidant activity (DPPH) than under high irradiance. The improved antioxidative activity under low light levels might be due to high availability of total flavonoids, phenolics and anthocyanin content in the plant extract. It was also found that an increase in the production of CBSM was due to high PAL activity under low light, probably signifying more availability of phenylalanine (Phe) under this condition. PMID:22754297

  17. NBO, conformational, NLO, HOMO-LUMO, NMR and electronic spectral study on 1-phenyl-1-propanol by quantum computational methods.

    PubMed

    Xavier, S; Periandy, S; Ramalingam, S

    2015-02-25

    In this study, FT-IR, FT-Raman, NMR and UV spectra of 1-phenyl-1-propanol, an intermediate of anti-depressant drug fluoxetine, has been investigated. The theoretical vibrational frequencies and optimized geometric parameters have been calculated by using HF and density functional theory with the hybrid methods B3LYP, B3PW91 and 6-311+G(d,p)/6-311++G(d,p) basis sets. The theoretical vibrational frequencies have been found in good agreement with the corresponding experimental data. (1)H and (13)C NMR spectra were recorded and chemical shifts of the molecule were compared to TMS by using the Gauge-Independent Atomic Orbital (GIAO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy, dipole moment and frontier molecular orbital energies are performed using HF and DFT methods. The thermodynamic properties (heat capacity, entropy and enthalpy) at different temperatures are also calculated. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. The local reactivity of the molecule has been studied using the Fukui function. NLO properties related to polarizability and hyperpolarizability are also discussed.

  18. Photocatalytic Conversion of CO2 to CO using Rhenium Bipyridine Platforms Containing Ancillary Phenyl or BODIPY Moieties

    SciTech Connect

    Andrade, Gabriel; Pistner, Allen; Yapp, Glenn P. A.; Lutterman, Daniel A; Rosenthal, Joel

    2013-01-01

    Harnessing of solar energy to drive the reduction of carbon dioxide to fuels requires the development of efficient catalysts that absorb sunlight. In this work, we detail the synthesis, electrochemistry and photophysical properties of a set of homologous fac-ReI(CO)3 complexes containing either an ancillary phenyl (8) or BODIPY (12) substituent. These studies demonstrate that both the electronic properties of the rhenium center and BODIPY chromophore are maintained for these systems. Photolysis studies demonstrate that both assemblies 8 and 12 are competent catalysts for the photochemical reduction of CO2 to CO in DMF using triethanolamine (TEOA) as a sacrificial reductant. Both these systems display TOFs for photocatalytic CO production upon irradiation with light ( ex 400 nm) of ~5 hr 1 with TON values of approximately 20. Although structural and photophysical measurements demonstrate that electronic coupling between the BODIPY and fac-ReI(CO)3 units is limited for complex 12, this work clearly shows that the photoactive BODIPY moiety is tolerated during catalysis and does not interfere with the observed photochemistry. When taken together, these results provide a clear roadmap for the development of advanced rhenium bipyridine complexes bearing ancillary BODIPY groups for the efficient photocatalytic reduction of CO2 using visible light.

  19. Molecular Docking Study of Catecholamines and [4-(Propan-2-yl) Phenyl]Carbamic acid with Tyrosine Hydroxylase

    PubMed Central

    Parveen, Zahida; Nawaz, Muhammad Sulaman; Shakil, Shazi; Greig, Nigel H.; Kamal, Mohammad A.

    2016-01-01

    Parkinson’s disease is a major age-related neurodegenerative disorder. As the classical disease-related motor symptoms are associated with the loss of dopamine-generating cells within the substantia nigra, tyrosine hydroxylase (TH), the rate-limiting enzyme in the synthesis of catecholamines has become an important target in the development of Parkinson’s disease drug candidates, with the focus to augment TH levels or its activity. By contrast, TH inhibitors are of relevance in the treatment of conditions associated with catecholamine over-production, as occurs in pheochromocytomas. To aid characterizing new drug candidates, a molecular docking study of catecholamines and a novel hypothetical compound [4-(propan-2-yl) phenyl]carbamic acid (PPCA) with TH is described. Docking was performed using Autodock4.2 and results were analyzed using Chimera1.5.2. All the studied ligands were found to bind within a deep narrow groove lined with polar aromatic and acidic residues within TH. Our results corroborated a ‘hexa interacting amino acids unit’ located in this deep narrow groove crucial to the interaction of PPCA and the studied catecholamines with TH, whereby the ‘His361-His336 dyad’ was found to be even more crucial to these binding interactions. PPCA displayed a binding interaction with human TH that was comparable to the original TH substrate, L-tyrosine. Hence PPCA may warrant in vitro and in vivo characterization with TH to assess its potential as a candidate therapeutic. PMID:22583429

  20. 3-(Adamantan-1-yl)-4-ethyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione

    PubMed Central

    El-Emam, Ali A.; Al-Abdullah, Ebtehal S.; Al-Tuwaijri, Hanaa M.; Said-Abdelbaky, Mohammed; García-Granda, Santiago

    2012-01-01

    The title compound, C25H35N5S, has an approximately C-shaped conformation. The dihedral angle between the triazole and phenyl planes is 79.5 (2)°. The crystal structure consists of infinite chains parallel to the b axis, constructed by C—H⋯S hydrogen bonds between translation-related mol­ecules. Adjacent chains are linked via weak C—H⋯C inter­actions between the adamantyl and phenyl groups. PMID:22904841

  1. Asymmetric hydrogenation in the presence of bisdiphenylphosphine complexes of rhodium. 3. Molecular structure of 2R-3-phenyl-2-(N-methyldiphenylphosphinamino)-1-diphenylphosphinoxypropane (1,5-cyclooctadiene)rhodium(I) perchlorate and its effectiveness as an enantioselective catalyst

    SciTech Connect

    Struchkov, Yu.T.; Yanovskii, A.I.; Pavlov, V.A.; Voloboev, A.A.; Klabunovskii, E.I.

    1987-09-10

    The structure of 2R-3-phenyl-2-methyl-diphenylphosphinamino-1-diphenylphosphinoxypropane(1,5-cyclooctadiene)rhodium (I) perchlorate was determined by x-ray crystallographic analysis, and the asymmetric arrangement of the phosphine phenyl groups was established. Examination of the established structure of the complex in comparison with the previously investigated structures of asymmetric hydrogenation catalysts showed the existence of a correlation between the configuration of the phosphorus atoms in the catalytic complexes and the configuration of the hydrogenation product.

  2. Oxidation of phenyl and hydride ligands of bis(pentamethylcyclopentadienyl)hafnium derivatives by nitrous oxide via selective oxygen atom transfer reactions: insights from quantum chemistry calculations.

    PubMed

    Xie, Hujun; Liu, Chengcheng; Yuan, Ying; Zhou, Tao; Fan, Ting; Lei, Qunfang; Fang, Wenjun

    2016-01-21

    The mechanisms for the oxidation of phenyl and hydride ligands of bis(pentamethylcyclopentadienyl)hafnium derivatives (Cp* = η(5)-C5Me5) by nitrous oxide via selective oxygen atom transfer reactions have been systematically studied by means of density functional theory (DFT) calculations. On the basis of the calculations, we investigated the original mechanism proposed by Hillhouse and co-workers for the activation of N2O. The calculations showed that the complex with an initial O-coordination of N2O to the coordinatively unsaturated Hf center is not a local minimum. Then we proposed a new reaction mechanism to investigate how N2O is activated and why N2O selectively oxidize phenyl and hydride ligands of . Frontier molecular orbital theory analysis indicates that N2O is activated by nucleophilic attack by the phenyl or hydride ligand. Present calculations provide new insights into the activation of N2O involving the direct oxygen atom transfer from nitrous oxide to metal-ligand bonds instead of the generally observed oxygen abstraction reaction to generate metal-oxo species.

  3. Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent.

    PubMed

    Radulović, Niko S; Mladenović, Marko Z; Stojanović-Radić, Zorica; Bogdanović, Goran A; Stevanović, Dragana; Vukićević, Rastko D

    2014-08-01

    A library of 16 2-substituted methyl acetoacetates containing ferrocenyl or phenyl units was designed to disclose differences in the antimicrobial activity of ferrocene-containing compounds and their phenyl analogs. Two methyl acetoacetates, whose structures do not contain an aromatic nucleus, were also included in order to probe the inherent activity of the scaffold itself. The acetoacetates were synthesized (low-to-good yields) and fully characterized by spectral (MS, IR, UV-Vis, 1D and 2D NMR) and electrochemical (cyclic voltammetry) techniques. Single-crystal X-ray analysis has been performed for methyl 2-acetyl-2-(ferrocenylmethyl)-5-methylhex-4-enoate. All compounds have demonstrated in vitro antimicrobial activity against six bacterial (three Gram-positive and three Gram-negative) and two fungal strains with minimal inhibitory concentration values of 0.0050-20.6 μmol mL(-1). The most active compound was 2-acetyl-2-(ferrocenylmethyl)-4-methylpent-4-enoate whose activity was comparable to that of nystatin against the yeast Candida albicans. Agglomerative hierarchical clustering statistical analysis of the antimicrobial assay data demonstrated that ferrocene-containing compounds have statistically different and greater antimicrobial activity when compared to their phenyl analogs.

  4. Efficient enantioselective synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by Leifsonia xyli CCTCC M 2010241 using isopropanol as co-substrate.

    PubMed

    Ouyang, Qi; Wang, Pu; Huang, Jin; Cai, Jinbo; He, Junyao

    2013-03-01

    (R)-[3,5-Bis(trifluoromethyl)phenyl] ethanol is a key chiral intermediate for the synthesis of aprepitant. In this paper, an efficient synthetic process for (R)-[3,5- bis(trifluoromethyl)phenyl] ethanol was developed via the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone, catalyzed by Leifsonia xyli CCTCC M 2010241 cells using isopropanol as the co-substrate for cofactor recycling. Firstly, the substrate and product solubility and cell membrane permeability of biocatalysts were evaluated with different co-substrate additions into the reaction system, in which isopropanol manifested as the best hydrogen donor of coupled NADH regeneration during the bioreduction of 3,5-bis(trifluoromethyl) acetophenone. Subsequently, the optimization of parameters for the bioreduction were undertaken to improve the effectiveness of the process. The determined efficient reaction system contained 200 mM of 3,5-bis(trifluoromethyl) acetophenone, 20% (v/v) of isopropanol, and 300 g/l of wet cells. The bioreduction was executed at 30°C and 200 rpm for 30 h, and 91.8% of product yield with 99.9% of enantiometric excess (e.e.) was obtained. The established bioreduction reaction system could tolerate higher substrate concentrations of 3,5- bis(trifluoromethyl) acetophenone, and afforded a satisfactory yield and excellent product e.e. for the desired (R)-chiral alcohol, thus providing an alternative to the chemical synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol.

  5. Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases

    NASA Astrophysics Data System (ADS)

    Singh, A. K.; Pandey, O. P.; Sengupta, S. K.

    New Zn(II) complexes have been synthesized by the reactions of zinc(II) acetate with Schiff bases derived from 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde, 2-hydroxyacetophenone or indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non-electrolytes. Elemental analyses suggest that the complexes have 1:1 stoichiometry of the type [ZnL(H 2O) 2], [ZnL'(OAc) 2(H 2O) 2] (L = dianionic Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and 2-hydroxyacetophenone or indoline-2,3-dione; L' = neutral Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde) and they were characterized by FT-IR, 1H NMR, 13C NMR and FAB mass. All these Schiff bases and their complexes have also been screened for their antibacterial activities against Bacillus subtilis, Escherichia coli and antifungal activities against Colletotrichum falcatum, Aspergillus niger, Fusarium oxysporium and Carvularia pallescence by petriplates methods.

  6. An improvement of performance in n-channel organic field effect transistors with N-phenyl[60]fulleropyrrolidines by molecular doping.

    PubMed

    Long, Dang Xuan; Karakawa, Makoto; Noh, Yong-Young

    2016-09-14

    The high performance of soluble [60]fulleropyrrolidine upon its use as the active layer of n-channel organic field-effect transistors (OFETs) is reported. The two materials, N-phenyl derivatives C60-fused-N-phenyl-2-phenylpyrrolidine ([C60]PhNPh) and C60-fused N-phenyl-2-hexylpyrrolidine ([C60]HexNPh), have well-controlled molecular structures with a modification of the pyrrolidine ring, with no increase in the LUMO level, achieving a high mobility and highly ambient stable n-type OFET. The top-gate, bottom-contact device shows a high electron charge-carrier mobility of up to 0.14 and 0.08 cm(2) V(-1) s(-1) for [C60]PhNPh and [C60]HexNPh, respectively, (Ion/Ioff = 10(6)) with the commonly used CYTOP dielectric. Excess carriers introduced by a small amount of chemical doping of polyethyleneimine (PEI) compensate traps by shifting the Fermi level (EF) toward the respective transport energy levels and therefore increase charge-carrier mobility (0.26 and 0.1 cm(2) V(-1) s(-1)) and provide good ambient operational stability compared with pristine devices. PMID:27523163

  7. Rapid purification of calsequestrin from cardiac and skeletal muscle sarcoplasmic reticulum vesicles by Ca2+-dependent elution from phenyl-sepharose.

    PubMed

    Cala, S E; Jones, L R

    1983-10-10

    Treatment of cardiac or skeletal muscle sarcoplasmic reticulum vesicles with 0.1 M sodium carbonate selectively extracts both the Ca2+-binding protein calsequestrin and the two "intrinsic glycoproteins," while leaving the Ca2+-dependent ATPase membrane bound. Phenyl-Sepharose chromatography in the presence of ethylene glycol bis(beta-aminoethyl ether)-N,N,N',N'-tetraacetic acid (EGTA) and high salt (0.5 M NaCl) readily fractionates these solubilized proteins into a Ca2+-elutable fraction, which contains purified calsequestrin, and a low ionic strength elutable fraction, which contains one of the two intrinsic glycoproteins. Elution of calsequestrin from phenyl-Sepharose occurs near 1 mM Ca2+. Copurifying with calsequestrin are an homologous set of high molecular weight proteins, which like calsequestrin stain blue with Stains-All. These proteins are present in trace amounts and do not correspond to any sarcoplasmic reticulum proteins previously identified. Elution of calsequestrin from phenyl-Sepharose is consistent with the Ca2+-binding protein losing its hydrophobic character in the presence of millimolar Ca2+. This behavior is converse to that observed for several calmodulin-like proteins, which are eluted from hydrophobic gels in the presence of EGTA. The high yield and purity of calsequestrin prepared by this method makes possible a unique system for studying what may be a distinct class of Ca2+-binding proteins.

  8. [N-Benzyl-N-(2-phenyl­eth­yl)di­thio­carbamato-κ2 S,S′]tri­phenyl­tin(IV) and [bis­(2-meth­oxy­eth­yl)di­thio­carbamato-κ2 S,S′]tri­phenyl­tin(IV): crystal structures and Hirshfeld surface analysis

    PubMed Central

    Mohamad, Rapidah; Awang, Normah; Kamaludin, Nurul Farahana; Jotani, Mukesh M.; Tiekink, Edward R. T.

    2016-01-01

    The crystal and mol­ecular structures of two tri­phenyl­tin di­thio­carbamates, [Sn(C6H5)3(C16H16NS2)], (I), and [Sn(C6H5)3(C7H14NO2S2)], (II), are described. In (I), the di­thio­carbamate ligand coordinates the SnIV atom in an asymmetric manner, leading to a highly distorted trigonal–bipyramidal coordination geometry defined by a C3S2 donor set with the weakly bound S atom approximately trans to one of the ipso-C atoms. A similar structure is found in (II), but the di­thio­carbamate ligand coordinates in an even more asymmetric fashion. The packing in (I) features supra­molecular chains along the c axis sustained by C—H⋯π inter­actions; chains pack with no directional inter­actions between them. In (II), supra­molecular layers are formed, similarly sustained by C—H⋯π inter­actions; these stack along the b axis. An analysis of the Hirshfeld surfaces for (I) and (II) confirms the presence of the C—H⋯π inter­actions but also reveals the overall dominance of H⋯H contacts in the respective crystals. PMID:27746946

  9. Optical and THz reflectance investigations of organic solar cells

    NASA Astrophysics Data System (ADS)

    Sporea, Dan; Mihai, Laura; Sporea, Adelina; Galagan, Yulia

    2016-04-01

    Two Organic Photovoltaic devices having a photoactive layer containing Poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5- (4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) and [6,6]-phenyl C61-butyric acid methyl ester (PCBM, 99%), and the layer sequences - glass/ITO/ZnO/PAL/PEDOT:PSS/Ag/encapsulation were non-destructively investigated by diffuse optical spectral reflectance, THz spectroscopy and THz imaging. The proposed methods proved to be powerful tools to support quality assurance in organic solar cells development, facilitating both the localization of manufacturing defects and the device degradation, as they are combined with "classical" evaluation means.

  10. Negative polarity of phenyl-C{sub 61} butyric acid methyl ester adjacent to donor macromolecule domains

    SciTech Connect

    Alley, Olivia J.; Dawidczyk, Thomas J.; Hardigree, Josué F. Martínez; Katz, Howard E.; Wu, Meng-Yin; Johns, Gary L.; Markovic, Nina; Arnold, Michael S.

    2015-01-19

    Interfacial fields within organic photovoltaics influence the movement of free charge carriers, including exciton dissociation and recombination. Open circuit voltage (V{sub oc}) can also be dependent on the interfacial fields, in the event that they modulate the energy gap between donor HOMO and acceptor LUMO. A rise in the vacuum level of the acceptor will increase the gap and the V{sub oc}, which can be beneficial for device efficiency. Here, we measure the interfacial potential differences at donor-acceptor junctions using Scanning Kelvin Probe Microscopy, and quantify how much of the potential difference originates from physical contact between the donor and acceptor. We see a statistically significant and pervasive negative polarity on the phenyl-C{sub 61} butyric acid methyl ester (PCBM) side of PCBM/donor junctions, which should also be present at the complex interfaces in bulk heterojunctions. This potential difference may originate from molecular dipoles, interfacial interactions with donor materials, and/or equilibrium charge transfer due to the higher work function and electron affinity of PCBM. We show that the contact between PCBM and poly(3-hexylthiophene) doubles the interfacial potential difference, a statistically significant difference. Control experiments determined that this potential difference was not due to charges trapped in the underlying substrate. The direction of the observed potential difference would lead to increased V{sub oc}, but would also pose a barrier to electrons being injected into the PCBM and make recombination more favorable. Our method may allow unique information to be obtained in new donor-acceptor junctions.

  11. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine pretreatment attenuates methamphetamine-induced dopamine toxicity.

    PubMed

    Kita, Taizo; Saraya, Tutomu; Konishi, Noboru; Matsunari, Yasunori; Shimada, Keiji; Nakamura, Mitsutoshi; O'Hara, Kiichi; Wagner, George C; Nakashima, Toshikatsu

    2003-02-01

    The effects of pretreatment with MPTP (1-methyl4-phenyl-1,2,3,6-tetrahydropyridine) on the acute and long-term effects of methamphetamine on striatal dopamine were evaluated in BALB/c mice. Four subcutaneous injections of a non-toxic dose of MPTP (8 mg/kg, at 2 hr intervals) were followed three days later by a toxic regimen of methamphetamine (four injections of 4 mg/kg, at 2 hr intervals) and mice were sacrificed immediately or three days later. Control mice received saline in place of the MPTP or methamphetamine and mice were observed for acute changes in body temperature, self-injurious behaviour, and striatal dopamine metabolites, or long-term changes in striatal dopamine levels, tyrosine hydroxylase immunoreactivity and glial fibrillary acidic protein. It was observed that pretreatment with MPTP protected mice against the acute increase in body temperature caused by the methamphetamine but, at the same time, delayed the occurrence of self-injurious behaviour following the repeated injections of methamphetamine. Likewise, pretreatment with MPTP attenuated the long-term depletion of striatal dopamine induced by the methamphetamine as well as the large increase in glial fibrillary acidic protein and the reduction in tyrosine hydroxylase immunoreactivity. The MPTP-treatment itself did not alter any of these neurotoxic markers. Finally, the acute decrease in 3,4-dihydroxyphenyacetic acid levels and increased ratio of 3-methoxytyramine/dopamine observed 60 min. after a single injection of methamphetamine (4 mg/kg) were also attenuated in MPTP-treated mice. These results are discussed in the context of the hypothesis that the low-dose treatment with MPTP may modify exchange diffusion across the striatal cell membrane thereby altering the acute and long-lasting effects of methamphetamine.

  12. Mechanical and electrophysiological studies on the positive inotropic effect of 2-phenyl-4-oxo-hydroquinoline in rat cardiac tissues.

    PubMed Central

    Su, M. J.; Chang, G. J.; Kuo, S. C.

    1993-01-01

    1. The pharmacological and electrophysiological effect of 2-phenyl-4-oxo-hydroquinoline (YT-1), a new synthetic agent, were determined in rat isolated cardiac tissues and ventricular myocytes. 2. YT-1 was found to have a positive inotropic effect in both atria and ventricular muscles but did not cause significant increases in the spontaneously beating rate of right atria. 3. The positive inotropic effect of YT-1 was antagonized neither by beta-nor by alpha-adrenoceptor antagonists but was partially antagonized by a Ca2+ channel blocker (verapamil) and a K+ channel blocker (4-AP). 4. The action potential duration and amplitude of ventricular cells were progressively increased as the concentration of YT-1 was increased from 3 to 30 microM. 5. A voltage clamp study revealed that the prolongation of action potential duration by YT-1 was associated with a prominent inhibition of 4-AP-sensitive transient outward current (I(to)). At potentials negative to the reversal potential of K1-channels, the inward current through these channels was partially reduced by YT-1. At potentials positive to the reversal potential, the outward current through these channels was affected very little. 6. Although YT-1 blocked the amplitude of I(to), the voltage-dependence of the steady-state inactivation of I(to), was unaffected. 7. Apart from the inhibition of K+ currents, YT-1 also inhibited the sodium inward current. 8. The evidence suggests that YT-1 increases the slow inward Ca2+ current (ICa) significantly. 9. It is concluded that the positive inotropic effect of YT-1 is due predominantly to the increase of ICa and inhibition of I(to).(ABSTRACT TRUNCATED AT 250 WORDS) PMID:8106106

  13. Theoretical investigation on the isomerization reaction of 4-phenyl-hexa-1,5-enyne catalyzed by homogeneous Au catalysts.

    PubMed

    Liu, Yuxia; Zhang, Dongju; Bi, Siwei

    2010-12-16

    By carrying out density functional theory calculations, we have performed a detailed mechanism study for the cycloisomerization reaction of 4-phenyl-hexa-1,5-enyne catalyzed by homogeneous gold to better understand the observed different catalytic activity of several catalysts, including (PPh(3))AuBF(4), (PPh(3))AuCl, AuCl(3), and AuCl. In all situations, the reaction is found to involve two major steps: the initial nucleophilic addition of the alkynyl onto the alkene group and the subsequent 1,2-H migration. It is found that the potential energy surface profiles of systems are very different when different catalysts are used. For (PMe(3))AuBF(4)- and (PMe(3))AuCl-mediated systems, the nucleophilic addition is the rate-determining step, and the calculated free energy barriers are 15.2 and 41.9 kcal/mol, respectively. In contrast, for AuCl(3)- and AuCl-mediated systems, the reactions are controlled by the dissociations of catalysts from the product-like intermediates, and the calculated dissociation energies are 18.1 and 21.7 kcal/mol, respectively, which are larger than both the corresponding free energy barriers of the nucleophilic addition and the H-migration processes (8.5 and 7.3 kcal/mol for the AuCl(3)-mediated reaction, and 16.9 and 11.3 kcal/mol for the AuCl-mediated reaction). These results can rationalize the early experimental observations that the reactant conversion rates are 100, 0, and 50% when using (PPh(3))AuBF(4), (PPh(3))AuCl, and AuCl(3) as catalysts, respectively. The present study indicates that both the ligand and counterion of homogeneous Au catalysts importantly influence their catalytic activities, whereas the oxidation state of Au is not a crucial factor controlling the reactivity.

  14. Functional induction of P-glycoprotein efflux pump by phenyl benzenesulfonamides: Synthesis and biological evaluation of T0901317 analogs.

    PubMed

    Padala, Anil K; Wani, Abubakar; Vishwakarma, Ram A; Kumar, Ajay; Bharate, Sandip B

    2016-10-21

    N-(2,2,2-Trifluoroethyl)-N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-benzenesulfonamide (T0901317, 6) is a potent activator of pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. Herein, we aimed to investigate P-gp induction activity of T0901317 and establish its structure-activity relationship. T0901317 along with a series of N-triazolyl-methylene-linked benzenesulfonamides were synthesized and screened for P-gp induction activity using a rhodamine-123 based efflux assay in the P-gp overexpressing human adenocarcinoma LS-180 cells, wherein several compounds showed potent P-gp induction activity at 5 μM. Treatment with benzene sulphonamides led to the decrease in intracellular accumulation of a fluorescent P-gp substrate rhodamine-123 up to 48% (control 100%). In the western-blot studies, T0901317 (6) and its triazole linked analog 26e at 5 μM displayed induction of P-gp expression in LS180 cells. These compounds were non-toxic in LS-180 and human neuroblastoma SH-SY5Y cells (IC50 > 50 μM). The compound 26e showed significant P-gp induction even at 0.3 μM, indicating an excellent therapeutic window. These results clearly indicate promise of this class of compounds as potential agents to enhance amyloid-β clearance in Alzheimers patients.

  15. The Synthetic Elicitor 2-(5-Bromo-2-Hydroxy-Phenyl)-Thiazolidine-4-Carboxylic Acid Links Plant Immunity to Hormesis.

    PubMed

    Rodriguez-Salus, Melinda; Bektas, Yasemin; Schroeder, Mercedes; Knoth, Colleen; Vu, Trang; Roberts, Philip; Kaloshian, Isgouhi; Eulgem, Thomas

    2016-01-01

    Synthetic elicitors are drug-like compounds that induce plant immune responses but are structurally distinct from natural defense elicitors. Using high-throughput screening, we previously identified 114 synthetic elicitors that activate the expression of a pathogen-responsive reporter gene in Arabidopsis (Arabidopsis thaliana). Here, we report on the characterization of one of these compounds, 2-(5-bromo-2-hydroxy-phenyl)-thiazolidine-4-carboxylic acid (BHTC). BHTC induces disease resistance of plants against bacterial, oomycete, and fungal pathogens and has a unique mode of action and structure. Surprisingly, we found that low doses of BHTC enhanced root growth in Arabidopsis, while high doses of this compound inhibited root growth, besides inducing defense. These effects are reminiscent of the hormetic response, which is characterized by low-dose stimulatory effects of a wide range of agents that are toxic or inhibitory at higher doses. Like its effects on defense, BHTC-induced hormesis in Arabidopsis roots is partially dependent on the WRKY70 transcription factor. Interestingly, BHTC-induced root hormesis is also affected in the auxin-response mutants axr1-3 and slr-1. By messenger RNA sequencing, we uncovered a dramatic difference between transcriptional profiles triggered by low and high doses of BHTC. Only high levels of BHTC induce typical defense-related transcriptional changes. Instead, low BHTC levels trigger a coordinated intercompartmental transcriptional response manifested in the suppression of photosynthesis- and respiration-related genes in the nucleus, chloroplasts, and mitochondria as well as the induction of development-related nuclear genes. Taken together, our functional characterization of BHTC links defense regulation to hormesis and provides a hypothetical transcriptional scenario for the induction of hormetic root growth.

  16. A phenyl-thiadiazolylidene-amine derivative ejects zinc from retroviral nucleocapsid zinc fingers and inactivates HIV virions

    PubMed Central

    2012-01-01

    Background Sexual acquisition of the human immunodeficiency virus (HIV) through mucosal transmission may be prevented by using topically applied agents that block HIV transmission from one individual to another. Therefore, virucidal agents that inactivate HIV virions may be used as a component in topical microbicides. Results Here, we have identified 2-methyl-3-phenyl-2H-[1,2,4]thiadiazol-5-ylideneamine (WDO-217) as a low-molecular-weight molecule that inactivates HIV particles. Both HIV-1 and HIV-2 virions pretreated with this compound were unable to infect permissive cells. Moreover, WDO-217 was able to inhibit infections of a wide spectrum of wild-type and drug-resistant HIV-1, including clinical isolates, HIV-2 and SIV strains. Whereas the capture of virus by DC-SIGN was unaffected by the compound, it efficiently prevented the transmission of DC-SIGN-captured virus to CD4+ T-lymphocytes. Interestingly, exposure of virions to WDO-217 reduced the amount of virion-associated genomic RNA as measured by real-time RT-qPCR. Further mechanism-of-action studies demonstrated that WDO-217 efficiently ejects zinc from the zinc fingers of the retroviral nucleocapsid protein NCp7 and inhibits the cTAR destabilization properties of this protein. Importantly, WDO-217 was able to eject zinc from both zinc fingers, even when NCp7 was bound to oligonucleotides, while no covalent interaction between NCp7 and WDO-217 could be observed. Conclusion This compound is a new lead structure that can be used for the development of a new series of NCp7 zinc ejectors as candidate topical microbicide agents. PMID:23146561

  17. Synthesis and biological properties of new N-Mannich bases derived from 3-methyl-3-phenyl- and 3,3-dimethyl-succinimides. Part V.

    PubMed

    Kamiński, Krzysztof; Obniska, Jolanta; Chlebek, Iwona; Liana, Piotr; Pękala, Elżbieta

    2013-08-01

    Twenty four new 1-[(4-phenylpiperazin-1-yl)-methyl]- derivatives of 3-phenyl-3-methyl- (6-17) and 3,3-dimethyl-pyrrolidine-2,5-diones (18-29) have been synthesized and evaluated for their anticonvulsant activity in the maximum electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests after intraperitoneal injection in mice. The acute neurological toxicity was determined using the rotorod screen. Although no anti-seizure properties were found in the scPTZ screen, fourteen compounds revealed protection in electrically induced seizures. From these molecules seven compounds were tested in rats after oral administration (MES test). In the whole series the most effective in rats were 1-[{4-(4-fluorophenyl)-piperazin-1-yl}-methyl]-3-methyl-3-phenyl-pyrrolidine-2,5-dione (8) with ED₅₀ value of 7.78 mg/kg, it's 3-chlorophenyl- (10) and 3,4-dichlorophenyl- (12) analogs with ED₅₀ values of 27.93 mg/kg and 15.11 mg/kg, respectively. To explain the possible mechanism of action for the most active derivatives 8, 10 and 12 the influence on NaV1.2 sodium channel currents were evaluated in vitro. The results of electrophysiological studies showed higher inhibition of NaV1.2 currents in comparison with phenytoin used as a model antiepileptic drug active in electrically induces seizures. Additionally, eleven 3-phenyl-3-methyl-pyrrolidine-2,5-diones as more promising in the anticonvulsant screening were evaluated in the Vibrio harveyi test to estimate their anti/mutagenic activity.

  18. High-resolution rovibrational spectroscopy of jet-cooled phenyl radical: the ν19 out-of-phase symmetric CH stretch.

    PubMed

    Buckingham, Grant T; Chang, Chih-Hsuan; Nesbitt, David J

    2013-10-01

    Phenyl radical has been studied via sub-Doppler infrared spectroscopy in a slit supersonic discharge expansion source, with assignments for the highest frequency b2 out-of-phase C-H symmetric stretch vibration (ν19) unambiguously confirmed by ≤6 MHz (0.0002 cm(-1)) agreement with microwave ground state combination differences of McMahon et al. [Astrophys. J. 2003, 590, L61-64]. Least squares analysis of over 100 resolved rovibrational peaks in the sub-Doppler spectrum to a Watson Hamiltonian yields precision excited-state rotational constants and a vibrational band origin (ν0 = 3071.8915(4) cm(-1)) consistent with a surprisingly small red-shift (0.9 cm(-1)) with respect to Ar matrix isolation studies of Ellison and co-workers [J. Am. Chem. Soc. 2001, 123, 1977]. Nuclear spin weights and inertial defects confirm the vibrationally averaged planarity and (2)A1 rovibronic symmetry of phenyl radical, with analysis of the rotational constants consistent with a modest C2v distortion of the carbon backbone frame due to partial sp rehybridization of the σ C radical-center. Most importantly, despite the number of atoms (N = 11) and vibrational modes (3N - 6 = 27), phenyl radical exhibits a remarkably clean jet cooled high-resolution IR spectrum that shows no evidence of intramolecular vibrational relaxation (IVR) phenomena such as local or nonlocal perturbations due to strongly coupled nearby dark states. This provides strong support for the feasibility of high-resolution infrared spectroscopy in other aromatic hydrocarbon radical systems.

  19. High Resolution Rovibrational Spectroscopy of Jet-Cooled Phenyl Radical: the ν_{19} Out-Of Symmetric C-H Stretch

    NASA Astrophysics Data System (ADS)

    Buckingham, Grant T.; Chang, Chih-Hsuan; Nesbitt, David J.

    2013-06-01

    Phenyl radical has been studied via sub-Doppler infrared spectroscopy in a slit supersonic discharge expansion source, with assignments for the highest frequency b_{2} out-of-phase C-H symmetric stretch vibration (ν_{19}) unambiguously confirmed by ≤ 6 MHz (0.0002 cm^{-1}) agreement with microwave ground state combination differences of McMahon et al. [Astrophys. J. 590, L61-64 (2003)]. Least squares analysis of > 100 resolved rovibrational peaks in the sub-Doppler spectrum to a Watson Hamiltonian yields precision exited-state rotational constants and a vibrational band origin (ν_{0} = 3071.8915(4) cm^{-1}) consistent with a surprisingly small red-shift (0.9 cm^{-1}) with respect to Ar matrix isolation studies of Ellison and coworkers [J. Am. Chem. Soc. 123, 1977 (2001)]. Nuclear spin weights and inertial defects confirm the vibrationally averaged planarity and ^{2}A_{1} rovibronic symmetry of phenyl radical, with analysis of the rotational constants consistent with a modest C_{2v} distortion of the carbon backbone frame due to partial sp rehybridization of the σ C radical-center. Most importantly, despite the number of atoms (N = 11) and vibrational modes (3N-6 = 27), phenyl radical exhibits a remarkably clean jet cooled high resolution IR spectrum that shows no evidence of intramolecular vibrational relaxation (IVR) phenomena such as local or non-local perturbations due to strongly coupled nearby dark states. This provides strong support for the feasibility of high resolution infrared spectroscopy in other cyclic aromatic hydrocarbon radical systems.

  20. High-Resolution Rovibrational Spectroscopy of Jet-Cooled Phenyl Radical: The ν19 Out-of-Phase Symmetric CH Stretch

    NASA Astrophysics Data System (ADS)

    Buckingham, Grant T.; Chang, Chih-Hsuan; Nesbitt, David J.

    2013-10-01

    Phenyl radical has been studied via sub-Doppler infrared spectroscopy in a slit supersonic discharge expansion source, with assignments for the highest frequency b2 out-of-phase C-H symmetric stretch vibration (-19) unambiguously confirmed by ≤6 MHz (0.0002 cm-1) agreement with microwave ground state combination differences of McMahon et al. [Astrophys. J. 2003, 590, L61-64]. Least squares analysis of over 100 resolved rovibrational peaks in the sub-Doppler spectrum to a Watson Hamiltonian yields precision excited-state rotational constants and a vibrational band origin (-0 = 3071.8915(4) cm-1) consistent with a surprisingly small red-shift (0.9 cm-1) with respect to Ar matrix isolation studies of Ellison and co-workers [J. Am. Chem. Soc. 2001, 123, 1977]. Nuclear spin weights and inertial defects confirm the vibrationally averaged planarity and 2A1 rovibronic symmetry of phenyl radical, with analysis of the rotational constants consistent with a modest C2v distortion of the carbon backbone frame due to partial sp rehybridization of the σ C radical-center. Most importantly, despite the number of atoms (N = 11) and vibrational modes (3N - 6 = 27), phenyl radical exhibits a remarkably clean jet cooled high-resolution IR spectrum that shows no evidence of intramolecular vibrational relaxation (IVR) phenomena such as local or nonlocal perturbations due to strongly coupled nearby dark states. This provides strong support for the feasibility of high-resolution infrared spectroscopy in other aromatic hydrocarbon radical systems.