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Sample records for phenyl p-fluorophenyl thienyl-2

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

    PubMed

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

    1981-01-01

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

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

    PubMed Central

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

    2009-01-01

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

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

    PubMed

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

    2013-03-01

    1-(2-Thienyl)-2-(methylamino)propane (methiopropamine, MPA), the thiophene analogue of methamphetamine, has recently appeared on a number of websites offering 'legal highs' for sale and has also been reported as a new psychoactive substance by the European Monitoring Centre for Drugs and Drugs Addiction (EMCDDA) Early Warning System. The drug is currently not controlled in the European Union (EU) but it would be expected that forensic laboratories will encounter it during routine analysis. As no reference standard was available, we have established a three-step protocol for its synthesis. We have also synthesized its 3-thienyl isomer and have established that this is separable from methiopropamine by gas chromatography using one of our routine protocols. The synthetic methodology presented here could be readily extended to the syntheses of analogous compounds. Copyright © 2011 John Wiley & Sons, Ltd.

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

    PubMed

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

    2010-03-01

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

  5. 1-Phenyl­isatin

    PubMed Central

    Shukla, Deepak; Rajeswaran, Manju

    2011-01-01

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

  6. 4-Bromo­phenyl benzoate

    PubMed Central

    Gowda, B. Thimme; Foro, Sabine; Babitha, K. S.; Fuess, Hartmut

    2008-01-01

    The structure of the title compound (4BPBA), C13H9BrO2, is similar to that of phenyl benzoate (PBA), 4-methyl­phenyl benzoate (4MePBA) and 4-methoxy­phenyl benzoate, with somewhat different bond parameters. The dihedral angle between the phenyl and benzoyl rings in 4BPBA is 58.43 (17)°, compared with values of 55.7° in PBA and 60.17 (7)° in 4MPBA. The mol­ecules in the title compound are packed into infinite chains in the a-axis direction. PMID:21202158

  7. 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.

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... phenyl esters (generic name). 721.3063 Section 721.3063 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as substituted phenyl azo substituted phenyl esters (PMNs P-95...

  9. 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 P-95...

  10. 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...

  11. 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...

  12. Testing Consent Order on Dilsodecyl Phenyl Phosphite

    EPA Pesticide Factsheets

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

  13. 40 CFR 721.3063 - Substituted phenyl azo substituted phenyl esters (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  14. 40 CFR 721.536 - Halogenated phenyl alkane.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

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

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  18. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  19. 40 CFR 721.5917 - Phenyl azo dye (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  20. 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.

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

    PubMed

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

    2006-12-14

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

  2. 2-Amino-N′-phenyl­benzohydrazide

    PubMed Central

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

    2012-01-01

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

  3. Phenyl valerate esterase activity of human butyrylcholinesterase.

    PubMed

    Mangas, Iris; Vilanova, Eugenio; Estévez, Jorge

    2017-03-15

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

  4. S-Phenyl benzothio-ate.

    PubMed

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

    2012-10-01

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

  5. Photochemistry of ortho, ortho' dialkyl phenyl azides.

    PubMed

    Tsao, Meng-Lin; Platz, Matthew S

    2003-10-01

    Phenyl azide, 2,6-diethylphenyl azide, 2,6-diisopropylphenyl azide, and 2,4,6-tri-tert-butylphenyl azide were studied by laser flash photolysis (LFP) methods. LFP (266 nm) of the azides in glassy 3-methylpentane at 77 K produces the transient UV-vis absorption spectra of the corresponding singlet nitrenes. At 77 K, the singlet nitrenes relax to the corresponding triplet nitrenes. The triplet nitrenes are persistent at 77 K and their spectra were recorded. The rate constants of singlet to triplet intersystem crossing were determined at this temperature. LFP of 2,4,6-tri-tert-butyl phenyl azide in pentane at ambient temperature again produces a singlet nitrene, which is too short-lived to detect by nanosecond spectroscopy under these conditions. Unlike the other azides, the first detectable intermediate produced upon LFP of 2,4,6-tri-tert-butyl phenyl azide at ambient temperature is the benzazirine (285 nm) which has a lifetime of 62 ns controlled by ring opening to a didehydroazepine. The results are interpreted with the aid of Density Functional Theoretical and Molecular Orbital Calculations.

  6. Guanidinium 2-phenyl­acetate

    PubMed Central

    Smith, Graham; Wermuth, Urs D.

    2010-01-01

    In the structure of the title salt, CH6N3 +·C8H7O2 −, the guanidinium cation gives three cyclic hydrogen-bonding inter­actions with O-atom acceptors of three independent phenyl­acetate anions, one R 2 2(8) and two R 2 1(6), giving one-dimensional columnar structures which extend down the 42 axis in the tetra­gonal cell. Within these structures, there are solvent-accessible voids of volume 86.5 Å3. PMID:21588273

  7. Epoxy resin cure. [Phenyl glycidyl ether

    SciTech Connect

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

    1986-07-01

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

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

    PubMed

    Comandini, A; Malewicki, T; Brezinsky, K

    2012-03-15

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

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

    USDA-ARS?s Scientific Manuscript database

    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...

  10. Synthesis and Electrochromic Properties of Star-Shaped Oligomers with Phenyl Cores.

    PubMed

    Zeng, Jinming; Zhang, Xiaoyuan; Zhu, Xiaoting; Liu, Ping

    2017-09-05

    A series of star-shaped conjugated oligomers, 1,3,5-tri(2'-thienyl) benzene (3TB), 1,3,5-tri(3',4'-ethylenedioxythienyl) benzene (3EB), 1,3,5-tri[5',2"-(3",4"-ethylenedioxy-thienyl)-2'-thienyl] benzene (3ETB), and 1,3,5-tri[5',2"-(3",4"-ethylenedioxy-thienyl)-2'-thienyl]-4-(3',4'-ethylenedioxythienyl)benzene (3TB-4EDOT), were synthesized. The star-shaped polymer, poly(1,3,5-tri[5',2"-(3",4"-ethylenedioxythineyl)-2'-thienyl]benzene) (P3ETB), was also prepared. The electrochemical and electrochromic properties of these conjugated oligomers and polymer were investigated. These oligomer and polymer films showed reversible, clear color changes upon electrochemical doping and dedoping. The color of the P3ETB film reversibly changed from orange to blue under doping and dedoping. The switching times for doping and dedoping were 1.2 and 0.9 s, respectively. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. 4-Carbamoylpiperidinium phenyl­acetate hemihydrate

    PubMed Central

    Smith, Graham; Wermuth, Urs D.

    2010-01-01

    The asymmetric unit of the title compound, C6H13N2O+·C8H7O2 −·0.5H2O, comprises two isonipecotamide cations, two phenyl­acetate anions and a water mol­ecule of solvation. The hydrogen-bonding environments for both sets of ion pairs are essentially identical with the piperidinium and amide ‘ends’ of each cation involved in lateral heteromolecular hydrogen-bonded cyclic N—H⋯O associations [graph set R 2 2(11)] which incorporate a single carboxyl O-atom acceptor. These cyclic motifs enclose larger R 5 5(21) cyclic systems, forming sheet substructures which lie parallel to (101) and are linked across b by the single water mol­ecule via water O—H⋯Oc (c = carboxylate) associations, giving a duplex-sheet structure. PMID:21589544

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

    PubMed Central

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

    2014-01-01

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

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

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M. (Inventor)

    1990-01-01

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

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

    PubMed

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

    2012-05-01

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

  15. The zeolite mediated isomerization of allyl phenyl ether

    NASA Astrophysics Data System (ADS)

    Pebriana, R.; Mujahidin, D.; Syah, Y. M.

    2017-04-01

    Allyl phenyl ether is an important starting material in organic synthesis that has several applications in agrochemical industry. The green transformation of allyl phenyl ether assisted by heterogeneous catalyst is an attractive topic for an industrial process. In this report, we investigated the isomerization of allyl phenyl ether by heating it in zeolite H-ZSM-5 and Na-ZSM-5. The conversion of allyl phenyl ether (neat) in H-ZSM-5 was 67% which produced 40% of 2-allylphenol, 17% of 2-methyldihydrobenzofuran, and other product (4:1.7:1), while in Na-ZSM-5 produced exclusively 2-allylphenol with 52% conversion. These results showed that zeolite properties can be tuned to give a selective transformation by substitution of metal ion into the zeolite interior.

  16. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  17. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  18. 40 CFR 721.10349 - 1,4-Benzenediamine, N′-(alkyl)-N-[4-[(alkyl)amino]phenyl]-N-phenyl- (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  19. A biochemical explanation of phenyl acetate neurotoxicity in experimental phenylketonuria.

    PubMed

    Loo, Y H; Potempska, A; Wisniewski, H M

    1985-11-01

    The in vivo formation of [1-14C]acetyl-coenzyme A from D-[3-14C]3-hydroxybutyrate in the brain of the suckling rat was not affected by postnatal exposure to phenyl acetate. However, utilization of the generated acetyl-coenzyme A was significantly inhibited in certain metabolic reactions, namely synthesis of fatty acids and of sterols, but not in others as the Krebs cycle reactions that lead to the production of dicarboxylic amino acids. The incorporation of D-[U-14C]glucosamine into N-acetylneuraminic acid bound to glycoproteins was appreciably diminished in the rat pup previously exposed to maternal phenylketonuria induced by phenyl acetate. During the period of very rapid development of the brain, interference by phenyl acetate and/or its metabolites with certain critical biosynthetic pathways that require acetyl-coenzyme A would significantly contribute to retarded maturation of the brain that occurs in phenylketonuria.

  20. 4-Chloro­phenyl 4-methyl­benzoate

    PubMed Central

    Gowda, B. Thimme; Foro, Sabine; Babitha, K. S.; Fuess, Hartmut

    2008-01-01

    The crystal structure of the title compound (4CP4MBA), C14H11ClO2, resembles those of 3-chloro­phenyl 4-methyl­benzoate (3CP4MBA), 4-methyl­phenyl 4-methyl­benzoate (4MP4MBA), 4-methyl­phenyl 4-chloro­benzoate (4MP4CBA) and other aryl benzoates with similar bond parameters. The dihedral angle between the benzene rings in 4CP4MBA is 63.89 (8)°, compared with 71.75 (7)° in 3CP4MBA, 63.57 (5)° in 4MP4MBA and 51.86 (4)° in 4MP4CBA. In the crystal structure of the title compound, the mol­ecules are linked into an infinite chain along the a axis via C—H—O hydrogen bonds. PMID:21203226

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

    NASA Technical Reports Server (NTRS)

    Ottenbrite, Raphael M. (Inventor)

    1989-01-01

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

  2. 40 CFR 721.9825 - Phenyl substituted triazolinones.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  3. 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.). Copyright © 2011 Elsevier Ltd. All rights reserved.

  4. 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 P-00...

  5. 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 P-00...

  6. 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 P-00...

  7. 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 P-00...

  8. 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 P-00...

  9. 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...

  10. 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...

  11. 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...

  12. 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.

  13. 2-Phenyl-2-(pyridin-2-yl)hexahydro­pyrimidine

    PubMed Central

    Jayaratna, Naleen B.; Norman, Richard E.

    2010-01-01

    The title compound, C15H17N3, was prepared by reaction of benzoyl­pyridine and hexahydropyrimidine. The 1,3-diazinane ring adopts a chair conformation with one N—H group axial and the other equatorial. The axial N—H group participates in very weak hydrogen bonding to the lone pair of electrons of the N atom with the equatorial H atom producing a very weakly hydrogen-bonded dimer. The pyridine N atom accepts an inter­nal hydrogen bond from the equatorial H atom. The phenyl ring adopts an equatorial position while the pyridine ring is axial. The phenyl ring exhibits a slight twist (ca 25°) relative to the hexahydropyrimidine ring. The pyridine ring stacks with symmetry-related pyridine rings. PMID:21589448

  14. Surfactant composition containing alkylated biphenylyl phenyl ether sulfonates

    SciTech Connect

    Hinkamp, P. E.

    1984-09-04

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

  15. Synthesis and Modification of Carboxylated Polyphenylenes and Phenylated Polyimides

    DTIC Science & Technology

    1976-03-01

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

  16. Photochemistry of Fluorinated Phenyl Nitrenes: Matrix Isolation of Fluorinated Azirines.

    PubMed

    Morawietz, Jens; Sander, Wolfram

    1996-06-26

    2,6-Difluorophenylnitrene and pentafluorophenylnitrene were generated in solid argon at 10 K by irradiation of the corresponding phenyl azides and characterized by IR and UV spectroscopy. Selective irradiation with lambda = 444 nm results in the formation of the corresponding azirines, while ketene imines are not produced. On lambda = 366 nm irradiation the azirines rearrange back to the nitrenes. The assignment of the azirines is confirmed by ab-initio calculations.

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

    PubMed

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

    1999-01-01

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

  18. 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. Copyright © 2011 Elsevier Ltd. All rights reserved.

  19. 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. Copyright © 2012 Elsevier Ltd. All rights reserved.

  20. 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. Copyright © 2011 Elsevier Ltd. All rights reserved.

  1. 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. Copyright © 2011 Elsevier Ltd. All rights reserved.

  2. 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. Copyright © 2011 Elsevier Ltd. All rights reserved.

  3. Electron Correlation and Photo Physics of Phenyl Substituted Polyacetylenes

    NASA Astrophysics Data System (ADS)

    Ghosh, Haranath; Mazumdar, S.; Shukla, Alok

    We investigate theoretically photoluminescence (PL) properties of mono and di-phenyl substituted trans-polyacetylene (t-PA), namely, poly-phenylacetylene (PPA) and poly-diphenylacetylene (PDPA), respectively. PL is a consequence of the occurrence of the two-photon state (2Ag) above the optically excited state (1Bu). Usually, electron correlation leads to confinement of 1Bu as well as the ground state. We show, in contrast, that in phenyl-substituted polyacetylenes electron-electron interactions cause enhanced delocalization of quasiparticles in the optically excited state from the backbone polyene chain into the phenyl groups. This coulomb enhanced delocalization in the transverse direction leads to confinement in the longitudinal direction and causes crossover between the 1Bu and 2Ag. We further show that in the absence of electron repulsion the low energy absorption is x-polarized whereas the high energy absorpion is predominantly y-polarized. In contrast, in presence of many body electron interaction both of them (low and high energy absorptions) are x-polarized. Thus photophysics of PPA/PDPA etc. are consequences of true many body effects.

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

    SciTech Connect

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

    2007-01-01

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

  5. 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.

  6. Phase transformation of calcium phenyl phosphate in calcium hydroxyapatite

    SciTech Connect

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

    2007-07-03

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

  7. S-Phenyl 4-meth-oxy-benzothio-ate.

    PubMed

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

    2012-04-01

    In the mol-ecule of the title thio-ester, C(14)H(12)O(2)S, the dihedral angle between the phenyl and benzene rings is 71.8 (3)°. The meth-oxy group is essentially coplanar with the benezene ring to which it is bonded, with an r.m.s. deviation of 0.0065 (5) Å for the non-H atoms involved. In the crystal, weak C-H⋯π inter-actions are present.

  8. 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

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

    DTIC Science & Technology

    1982-09-01

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

  10. 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

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

    PubMed

    Lapin, I

    2001-01-01

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

  12. Thermolysis of surface-immobilized phenethyl phenyl ether

    SciTech Connect

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

    1991-01-01

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

  13. 6-Butyryl-5-hy-droxy-4-phenyl-seselin.

    PubMed

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

    2010-08-28

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

  14. 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 uses...

  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 721.9545 - 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...

  18. 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...

  19. 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...

  20. 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...

  1. 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...

  2. 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...

  3. 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...

  4. 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...

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

    NASA Technical Reports Server (NTRS)

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

    1985-01-01

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

  6. 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...

  7. 40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  8. 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...

  9. 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...

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

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  11. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  12. 40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

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

    DTIC Science & Technology

    1984-11-15

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

  14. 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...

  15. 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 subject...

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

    PubMed

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

    2008-01-01

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

  17. Water-promoted One-step Anodic Acetoxylation of Benzene to Phenyl Acetate with High Selectivity

    NASA Astrophysics Data System (ADS)

    Pei, Juan; Qin, Song; Li, Gui-ying; Hu, Chang-wei

    2011-04-01

    One-step anodic acetoxylation of benzene to phenyl acetate was studied in acetic acid-water solution using a one-compartment electrochemical cell in galvanostatic mode. Compared to the anhydrous system, the addition of water improved the current efficiency for the electro-synthesis of phenyl acetate. The maximum efficiency reached 4.8% with the selectivity of 96% to phenyl acetate when the electrolysis was carried out under the optimal conditions. The investigation also indicated that the concentration of phenyl acetate increased linearly in 12 h and reached 1.07 g/L with the selectivity of 95%. Cyclic voltammetry experiments showed that the adsorption of benzene at Pt anode enhanced by the addition of water was critical to the formation of phenyl acetate. An activated benzene mechanism was proposed for the anodic acytoxylation, and the analysis of gas products demonstrated that Kolbe reaction was the main side reaction.

  18. Orientation in methylation and phenylation of alkylbenzenes by cations generated by the nuclear chemical method

    SciTech Connect

    Sinotova, E.N.; Krylov, E.N.

    1987-11-10

    The distribution of the isomers and the relative activity of alkylbenzenes in electrophilic methylation and phenylation with methyl and phenyl cations generated by the nuclear chemical method are examined. These reactions are a convenient model of aromatic electrophilic substitution. Free methyl cations were generated by radioactive ..beta../sup -/ decay of tritium in totally tritiated methane. Free phenyl cations were generated from totally tritiated benzene C/sub 6/T/sub 6/ according to a similar scheme. During the reaction with alkylbenzenes methyl cations form isomeric alkyltoluenes and tritium-labeled toluene. The phenyl cations react with the alkylbenzenes and form isomeric alkyldiphenyls and tritium-labeled diphenyl. Both the Nathan-Baker substrate and position effects caused by the steric effect of the alkyl substitutents are observed in methylation and phenylation of alkylbenzenes by CT/sub 3//sup +/ and C/sub 6/T/sub 5//sup +/ cations generated by the nuclear chemical method.

  19. 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...

  20. 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...

  1. 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...

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

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

    Code of Federal Regulations, 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...

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Carbon black, 4- substituted] phenyl... Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl...) The chemical substance identified generically as carbon black, 4- substituted] phenyl-modified, sodium...

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

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

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  7. Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.

    PubMed

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

    2016-04-01

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

  8. Phenyl Derivative of Iron 5,10,15-Tritolylcorrole

    PubMed Central

    2015-01-01

    The phenyl–iron complex of 5,10,15-tritolylcorrole was prepared by reaction of the starting chloro–iron complex with phenylmagnesium bromide in dichloromethane. The organometallic complex was fully characterized by a combination of spectroscopic methods, X-ray crystallography, and density functional theory (DFT) calculations. All of these techniques support the description of the electronic structure of this phenyl–iron derivative as a low-spin iron(IV) coordinated to a closed-shell corrolate trianion and to a phenyl monoanion. Complete assignments of the 1H and 13C NMR spectra of the phenyl–iron derivative and the starting chloro–iron complex were performed on the basis of the NMR spectra of the regioselectively β-substituted bromo derivatives and the DFT calculations. PMID:24697623

  9. The Exotic Excited State Behavior of 3-PHENYL-2-PROPYNENITRILE

    NASA Astrophysics Data System (ADS)

    Jawad, Khadija M.; Viquez Rojas, Claudia I.; Slipchenko, Lyudmila V.; Zwier, Timothy S.

    2017-06-01

    3-phenyl-2-propynenitrile (Ph-C≡C-C≡N) is of interest to the study of Titan's atmosphere as it is a likely product of the photochemical reaction between two known species in that environment: benzene and cyanoacetylene. The gas phase jet-cooled resonant two-photon ionization, laser induced fluorescence, and preliminary dispersed fluorescence spectra were previously reported without firm assignments due to the scarcity of totally symmetric vibrations and the prevalence of strong bands of b2 and b1 symmetry vibrations. These had called into question the identity and geometry of the excited state(s) involved in the transitions. We will here present the completed set of dispersed fluorescence data along with an analysis of the potential energy surfaces and vibronic coupling characteristic of the close-lying excited states in this intriguing molecule.

  10. Eco-friendly synthesis and antimicrobial activities of some 1-phenyl-3(5-bromothiophen-2-yl)-5-(substituted phenyl)-2-pyrazolines.

    PubMed

    Sasikala, Ramalingam; Thirumurthy, Kannan; Mayavel, Perumal; Thirunarayanan, Ganesamoorthy

    2012-06-11

    Green catalyst fly ash: H2SO4 was prepared by mixing fly ash and sulphuric acid. Microwave irradiations are applied for solid phase cyclization of 5-bromo-2-thienyl chalcones and phenyl hydrazine hydrate in the presence of fly ash: H2SO4 yields, 1-phenyl-3(5-bromothiophen-2-yl)-5-(substituted phenyl)-2-pyrazolines. These pyrazolines were characterized by their physical constants and spectral data. The antimicrobial activities of all synthesized pyrazolines have been studied. Scanning electron microscopy (SEM) analysis shows the morphology changes between fly ash and the catalyst fly ash: H2SO4. The SEM photographs with the scale of 1 and 50 μm show the fly-ash particle is corroded by H2SO4 (indicated by arrow mark), and this may be due to dissolution of fly ash by H2SO4. The yields of 1-phenyl-3(5-bromothiophen-2-yl)-5-(substituted phenyl)-2-pyrazolines is more than 75% using this catalyst under microwave heating. All pyrazolines showed moderate activities against antimicrobial strains. We have developed an efficient catalytic method for synthesis of 1-phenyl-3(5-bromothiophen-2-yl)-5-(substituted phenyl)-2-pyrazolines by solid phase cyclization using a solvent-free environmentally greener catalyst fly ash: H2SO4 under microwave irradiation between aryl chalcones and hydrazine hydrate. This reaction protocol offers a simple, economical, environment friendly, non-hazardous, easier work-up procedure, and good yields. All synthesized pyrazoline derivatives showed moderate antimicrobial activities against bacterial and fungal strains.

  11. 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

    2015-01-07

    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. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  12. Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation.

    PubMed

    Lee, Myungmo; Lee, Young-Ju; Park, Eunyoung; Park, Yohan; Ha, Min Woo; Hong, Suckchang; Lee, Yeon-Ju; Kim, Taek-Soo; Kim, Mi-hyun; Park, Hyeung-geun

    2013-03-28

    An efficient enantioselective synthetic method for the synthesis of (2R)-5-phenyl-2-alkylproline tert-butyl esters was reported. The phase-transfer catalytic alkylation of tert-butyl-5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylate in the presence of chiral quaternary ammonium catalysts gave the corresponding alkylated products (up to 97% ee). The following diastereoselective reductions afforded chiral 5-phenyl-2-alkylprolines which can be applied to asymmetric synthesis as organocatalysts or synthesis of biologically active proline based compounds, such as chiral α-alkylated analogues of (+)-RP66803, as potential CCK antagonists.

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

    PubMed

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

    2011-08-01

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

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

    PubMed

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

    2016-05-01

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

  15. 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.

  16. 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.

  17. 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)

  18. 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)

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

    PubMed

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

    2013-01-01

    Six novel 2-(benzylcarbamoyl)phenyl derivatives were synthesized and characterized by (1) H-NMR, mass spectrometry, infrared spectra and elemental analysis. Their europium complexes were prepared and characterized by elemental analysis, EDTA titrimetric analysis, IR and UV spectra as well as molar conductivity measurements. The luminescence properties of these complexes were investigated and results show that 2-(benzylcarbamoyl)phenyl derivatives possess high selectivity and good coordination with the europium ion. Complex Eu-2-(benzylcarbamoyl)phenyl-2-phenylacetate showed green luminescence that was emitted by the ligand of 2-(benzylcarbamoyl)phenyl-2-phenylacetate, while other complexes showed the characteristic red luminescence of europium ion and also possessed high luminescence intensity. Copyright © 2012 John Wiley & Sons, Ltd.

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

    PubMed

    Imamura, Yorishige; Narumi, Rika; Shimada, Hideaki

    2007-02-01

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

  1. 6-(4-Amino-phen-yl)-2-meth-oxy-4-phenyl-nicotino-nitrile.

    PubMed

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

    2013-11-23

    In the structure of the title nicotino-nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino-phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π-π inter-actions between the 4-amino-phenyl rings of adjacent sheets, with centroid-centroid distances of 3.7499 (9) Å. C-H⋯π inter-actions are also present.

  2. 1-[2,2-Bis(phenyl-sulfon-yl)ethen-yl]-4-meth-oxy-benzene.

    PubMed

    Asahara, Haruyasu; Mayer, Peter; Mayr, Herbert

    2012-02-01

    In the title compound, C(21)H(18)O(5)S(2), the two sulfur-bound phenyl rings lie on opposite sides of the meth-oxy-phenyl group, making dihedral angles of 77.58 (8) and 87.45 (8)°with it. The dihedral angle between the sulfur-bound phenyl rings is 57.31 (8)°. In the crystal, π-π stacking is observed between the two sulfur-bound phenyl rings, with a centroid-centroid distance of 3.878 (1) Å and a dihedral angle of 7.58 (8)°. The mol-ecules are linked by weak C-H⋯O and C-H⋯π contacts.

  3. Methyl (E)-2-[(2-nitro-phen-oxy)meth-yl]-3-phenyl-acrylate.

    PubMed

    Anuradha, T; Devaraj, A; Seshadri, P R; Bakthadoss, M

    2012-06-01

    The title compound, C(17)H(15)NO(5), adopts an E conformation with respect to the C=C double bond of the phenyl-acrylate unit. The phenyl ring and methyl acrylate group of the phenyl-acrylate unit are disordered over two sets of sites with site-occupancy ratios of 0.705 (5):0.295 (5) and 0.683 (3):0.317 (3), respectively. The mean plane through the benzene ring of the phenyl acrylate makes dihedral angles of 88.4 (8) (major component) and 86.7 (8)° (minor component) with the nitro-phen-oxy ring; the dihedral angle between the two components is 3.64 (6)°. Intra-molecular C-H⋯O interactions stabilise the molecular structure. In the crystal, C-H⋯O inter-actions result in a chain of mol-ecules running along the b axis.

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

    PubMed

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

    2013-11-01

    In order to find the vitamin D receptor (VDR) ligand whose VDR agonistic activity is separated from the calcemic activity sufficiently, novel nonsecosteroidal analogs with phenyl-pyrrolyl pentane skeleton were synthesized and evaluated for the VDR binding affinity, antiproliferative activity in vitro and serum calcium raising ability in vivo (tacalcitol used as control). Among them, several compounds showed varying degrees of VDR agonistic and growth inhibition activities of the tested cell lines. The most effective compound 2g (EC₅₀: 1.06 nM) exhibited stronger VDR agonistic activity than tacalcitol (EC₅₀: 7.05 nM), inhibited the proliferations of HaCaT and MCF-7 cells with IC₅₀ of 2.06 μM and 0.307 μM (tacalcitol: 2.07 μM and 0.057 μM) and showed no significant effect on serum calcium. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

  5. Synthesis and photopolymerization kinetics of 2-phenyl-benzodioxole.

    PubMed

    Wang, Bowen; Yang, Jinliang; Nie, Jun; Zhu, Xiaoqun

    2014-04-01

    In this paper, a new photocoinitiator for free radical photopolymerization, belonging to the benzodioxole (BDO) derivatives, was synthesized and characterized, and the effect of phenyl at the 2-position of BDO was estimated. The structure of PhBDO was characterized by elemental analysis, (1)H NMR and (13)C NMR. Laser flash photolysis (LFP) and an electron spin resonance spin trapping technique (ESR-ST) were used to study the photochemical mechanisms. The rate of decomposition (Rd) of PhBDO in acetonitrile was studied by UV-Vis spectroscopy and the photopolymerization kinetics were monitored by real time Fourier Transform near-IR (FT-IR). The FT-IR results showed that the concentration of PhBDO and BP functionalities of the acrylates and the light intensity affected the polymerization rate and the final conversion. The results showed that the BP/PhBDO system had the same hydrogen abstraction mechanism and reactivity as the BP/BDO system. Consequently, PhBDO could also be an effective coinitiator.

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

    NASA Astrophysics Data System (ADS)

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

    2009-04-01

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

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

    PubMed Central

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

    2013-01-01

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

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

    PubMed

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

    2013-10-24

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

  9. Structural characterization of some N-phenyl-4-oxo-4H-2-chromone carboxamides.

    PubMed

    Gomes, Ligia Rebelo; Low, John Nicolson; Cagide, Fernando; Gaspar, Alexandra; Reis, Joana; Borges, Fernanda

    2013-06-01

    N-phenyl-4-oxo-4H-2-chromone carboxamides were found to be inactive as MAO inhibitors in contrast with their N-phenyl-4-oxo-4H-3-chromone carboxamide isomers. In order to obtain a close insight into the docking mechanism for this family of compounds, the molecular and supramolecular structures of nine N-phenyl-4-oxo-4H-2-chromone carboxamides were determined. It was found that, in most of the secondary structures, the N(amido) and the O(carboxyl) of the carboxamide residue participate in strong intramolecular interactions, with the O atom of the chromene ring and with the H(ortho)-C (phenyl), respectively. When the phenyl ring had accessible acceptors as substituents a third intramolecular hydrogen bond was also observed. As a consequence, rotations of the chromone and phenyl rings around the N-C(alpha) and C(alpha')-C=O are constrained and the compounds were found to be more planar than would otherwise be expected. The deviation from planarity of the whole molecule can be quantified by the dihedral angles between mean planes of the aromatic rings and it was found that they were mainly affected by the degree of torsion of the phenyl ring with respect to the amide residue. The molecular conformations assumed by the secondary amides clearly contrast with that of a related tertiary amide that was also determined in this study. The unavailability of the N in this compound as a donor strongly influences the molecular isomerism and conformation. This analysis demonstrates that the molecules can be classified into four groups depending on the types of interactions formed as described above. If the secondary N(amido) of the carboximide is involved in two intramolecular interactions then this atom does not form any intermolecular contacts. In all other cases it does and the supramolecular structure formed is in most cases supplemented by weak C-H···O interactions.

  10. 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.

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

    SciTech Connect

    Beste, Ariana; Buchanan III, A C

    2012-01-01

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

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

    PubMed

    Tezcan, Habibe; Tokay, Nesrin

    2010-01-01

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

  13. 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.

  14. 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.

  15. 1-Benzhydryl-4-(4-chloro­phenyl­sulfonyl)piperazine

    PubMed Central

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

    2008-01-01

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

  16. Synthesis of 1-methyl-2-phenyl-4-arylphthalazinium salts and their reaction with benzaldehyde

    SciTech Connect

    Ovchinnikova, I.G.; Pavlova, L.A.; Samartseva, I.V.

    1986-10-01

    1-Methyl-2-phenyl-4-arylphthalazinium perchorates, which exhibit the characteristics of CH acids, were obtained by the action of methylmagnesium iodide on 1-oxo-2-phenyl-4-aryl-1,2-dihydrophthalazines (Ar = C/sub 6/H/sub 5/, p-CH/sub 3/C/sub 6/H/sub 4/, p-C/sub 2/H/sub 5/OC/sub 6/H/sub 4/, p-FC/sub 6/H/sub 4/, p-ClC/sub 6/H/sub 4/, p-BrC/sub 6/H/sub 4/) followed by decomposition of the reaction mass with 57% perchloric acid. The 1-methylphthalazinium salts condense with benzaldehyde, giving 1-styryl-2-phenyl-4-arylphthalazinium perchlorates.

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

    PubMed Central

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

    2014-01-01

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

  18. 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

  19. 2-(1,3-Benzothia-zol-2-ylsulfan-yl)-1-phenyl-ethanone.

    PubMed

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

    2009-09-12

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

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

    PubMed

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

    2004-01-01

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

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

    PubMed

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

    2011-12-01

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

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

    PubMed

    Cao, Zhiling; Liu, Weiwei; Yin, Fujun

    2010-11-17

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

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

    PubMed Central

    Deng, Yanhua; Ma, Changqin; Zhang, Xiaomei

    2011-01-01

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

  4. Ethyl 3-(4-meth-oxy-phen-yl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propano-ate.

    PubMed

    Sugumar, P; Sankari, S; Manisankar, P; Ponnuswamy, M N

    2012-08-01

    In the title compound, C(26)H(24)N(2)O(3)Se, the selenadiazole ring is planar [maximum deviation = 0.002 (2) Å]. The dihedral angle between the selenadiazole ring and the attached phenyl ring is 49.00 (13)°. The crystal structure is stabilized by inter-molecular C-H⋯N and C-H⋯π inter-actions.

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

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Carbon black, 4- substituted] phenyl...

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

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Carbon black, 4- substituted] phenyl...

  7. 40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10075 Carbon black, 4- substituted] phenyl... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Carbon black, 4- substituted] phenyl...

  8. 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…

  9. 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…

  10. Stretching the phenazine MO in dppz: the effect of phenyl and phenyl-ethynyl groups on the photophysics of Re(I) dppz complexes.

    PubMed

    van der Salm, Holly; Larsen, Christopher B; McLay, James R W; Fraser, Michael G; Lucas, Nigel T; Gordon, Keith C

    2014-12-21

    A series of dipyrido[3,2-a:2',3'-c]phenazine (dppz)-based ligands have been synthesised in which phenyl or phenyl-ethynyl linkers are terminated by (t)Bu or CN units. The corresponding [ReCl(CO)3(L)] complexes are also prepared. Electrochemistry shows the ligand which contains a phenyl-ethynyl linker and CN substituent is most easily reduced (by 15 mV relative to the other ligands). All complexes are reduced and oxidised at similar potentials. Electronic absorption spectra are consistent with stabilisation of the LUMO by the binding of the metal centre, as complex spectra are red-shifted relative to their ligand. In addition, those containing phenyl-ethynyl linkers show spectra red-shifted (by 650 cm(-1)) relative to their phenyl-linked analogues. Raman and resonance Raman spectroscopy combined with DFT and TD-DFT calculations are consistent with ligands showing π,π* transitions, and complexes showing metal-to-ligand charge-transfer (MLCT) transitions as the lowest energy absorption. Ligands emit from the π,π* excited state (λem ranging from 450 to 470 nm in CH2Cl2). The complexes show emission from both π,π* and MLCT states; the λem(MLCT) lies at 650-666 nm. Transient lifetimes in CH2Cl2 are decreased by the CN substituent, as this increases knr. Transient resonance Raman spectra (TR(2)) of ligands show spectral features associated with the LC state, and the strong similarities between these and complex spectra support an LC excited state at 355 nm for the complexes. Two-colour TR(3) spectra show only small differences to ground state spectra, the most obvious being a decrease in intensity of C[triple bond, length as m-dash]C bands. For [ReCl(CO)3()] and [ReCl(CO)3()] an increase in intensity of a 1575 cm(-1) band attributed to the dppz˙(-) species suggests that these complexes have significant MLCT state population between 20-60 ns after photoexcitation.

  11. 1-(2,6-Diisopropyl-phen-oxy)-4-phenyl-phthalazine.

    PubMed

    Tong, Bihai; Mei, Qunying

    2012-08-01

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

  12. 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...

  13. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  14. 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...

  15. 40 CFR 721.2577 - Copper complex of (substituted sulfonaphthyl azo substituted phenyl) disulfonaphthyl azo, amine...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

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

  16. 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 copper...

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

    SciTech Connect

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

    2001-04-12

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

  18. 40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized (substituted) benzenesulfonic acid and naphthalenol (generic). 721.5286 Section 721.5286 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.5286 Benzenediazonium, phenyl]sulfonyl]amino...

  19. 40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized (substituted) benzenesulfonic acid and naphthalenol (generic). 721.5286 Section 721.5286 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.5286 Benzenediazonium, phenyl]sulfonyl]amino...

  20. 40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized (substituted) benzenesulfonic acid and naphthalenol (generic). 721.5286 Section 721.5286 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.5286 Benzenediazonium, phenyl]sulfonyl]amino...

  1. 40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized (substituted) benzenesulfonic acid and naphthalenol (generic). 721.5286 Section 721.5286 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.5286 Benzenediazonium, phenyl]sulfonyl]amino...

  2. 40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized (substituted) benzenesulfonic acid and naphthalenol (generic). 721.5286 Section 721.5286 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.5286 Benzenediazonium, phenyl]sulfonyl]amino...

  3. 40 CFR 721.10572 - Benzamide, N - [ [ 4- [(cyclopropylamino) carbonyl]phenyl] sulfonyl] -2 -methoxy-.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  4. 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.

  5. 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)

  6. Diastereoselective synthesis of 2-phenyl-3-(trifluoromethyl)piperazines as building blocks for drug discovery.

    PubMed

    Sánchez-Roselló, María; Delgado, Oscar; Mateu, Natalia; Trabanco, Andrés A; Van Gool, Michiel; Fustero, Santos

    2014-06-20

    The synthesis of enantiomerically pure cis- and trans-2-phenyl-3-(trifluoromethyl)piperazines is described. It involved, as the key step, a diastereoselective nucleophilic addition of the Ruppert-Prakash reagent (TMSCF3) to α-amino sulfinylimines bearing Ellman's auxiliary. This methodology allows an entry into hitherto unknown trifluoromethylated and stereochemically defined piperazines, key scaffold components in medicinal chemistry.

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

    USDA-ARS?s Scientific Manuscript database

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

  8. 4-Benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine

    PubMed Central

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

    2010-01-01

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

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

    PubMed

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

    2001-10-01

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

  10. 40 CFR 721.1620 - Benzenesulfonamide, alkylphenyl substituted phenyl substituted carbonyl- (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... phenyl substituted carbonyl- (PMN P-00-368) is subject to reporting under this section for the...), (g)(4)(i), and (g)(5). (iii) Release to water. Requirements as specified in § 721.90(a)(4), (b)(4... in § 721.125(a), (b), (c), (d), (f), (g), (h), and (k) are applicable to manufacturers, importers...

  11. 1,1,2,2-Tetra­phenyl-1λ5-diphosphane 1-sulfide

    PubMed Central

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

    2009-01-01

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

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

    PubMed

    Matayoshi, E D; Kleinfeld, A M

    1981-06-22

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

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

    USDA-ARS?s Scientific Manuscript database

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

  14. 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)

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  16. 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.

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

    PubMed

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

    2014-06-26

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

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

    PubMed

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

    2014-09-02

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

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

    PubMed Central

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

    2014-01-01

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

  20. 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

  1. 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.

  2. 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.

  3. 3-Benzyl-2-phenyl-1,3-thia­zolidin-4-one

    PubMed Central

    Fun, Hoong-Kun; Hemamalini, Madhukar; Shanmugavelan, Poovan; Ponnuswamy, Alagusundaram; Jagatheesan, Rathinavel

    2011-01-01

    In the title compound, C16H15NOS, the thia­zolidine ring, which is essentially planar [maximum deviation = 0.071 (2) Å], makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 49.45 (5)°. In the crystal, mol­ecules are linked by a weak inter­molecular C—H⋯O hydrogen bond, forming a supra­molecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C—H⋯π inter­action. PMID:22064819

  4. 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.

  5. 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

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

    PubMed

    Charette, Bronte J; Ritch, Jamie S

    2015-03-01

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

  7. Preparation and Characterization of Flexible Substrate Material from Phenyl-Thiophene-2-Carbaldehyde Compound.

    PubMed

    Rahman, Ashiqur; Islam, Mohammad Tariqul; Samsuzzaman, Md; Singh, Mandeep Jit; Akhtaruzzaman, Md

    2016-05-11

    In this paper, a novel phenyl-thiophene-2-carbaldehyde compound-based flexible substrate material has been presented. Optical and microwave characterization of the proposed material are done to confirm the applicability of the proposed material as a substrate. The results obtained in this work show that the phenyl-thiophene-2-carbaldehyde consists of a dielectric constant of 3.03, loss tangent of 0.003, and an optical bandgap of 3.24 eV. The proposed material is analyzed using commercially available EM simulation software and validated by the experimental analysis of the flexible substrate. The fabricated substrate also shows significant mechanical flexibility and light weight. The radiating copper patch deposited on the proposed material substrate incorporated with partial ground plane and microstrip feeding technique shows an effective impedance bandwidth of 3.8 GHz. It also confirms an averaged radiation efficiency of 81% throughout the frequency band of 5.4-9.2 GHz.

  8. 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.

  9. The influence of the different inductivity of acetyl phenyl-thiosemicarbazone-chitosan on antimicrobial activities.

    PubMed

    Zhong, Zhimei; Aotegen, Bayaer; Xu, Hui

    2011-06-01

    Ten different acetyl phenyl-thiosemicarbazone derivatives of chitosan were synthesized. Their structures were characterized by FT-IR and elemental analysis. The antimicrobial behaviors of CS and its derivatives against four species of bacteria and four crop-threatening pathogenic fungi were investigated in this paper. The results indicated that the antimicrobial activities of acetyl phenyl-thiosemicarbazone derivatives are much better than that of pure CS. The minimum value of MIC and MBC of the derivatives against Escherichia coli was 7.03 and 225 μg mL(-1), respectively. All of the derivatives had significant inhibiting effect on the investigated fungi in the concentration of 50-500 μg mL(-1), and the maximum inhibitory index was 93.10%. The bioactivities of the derivatives have relationship with the grafted groups with different inductivity. Copyright © 2011 Elsevier B.V. All rights reserved.

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

    PubMed

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

    2017-03-01

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

  11. The synthesis and characterization of Bis- (biguanide-p-phenyl) methane

    NASA Astrophysics Data System (ADS)

    Peng, Yongli; Pi, Zhenglin

    2017-06-01

    To decrease the curing temperature of epoxy resin with dicyandiamide, a new kind of modified dicyandiamide curing agent was prepared with daimio diphenyl methane and dicyandiamide as raw materials, distilled water as solvent and hydrochloric acid as a catalyst. The optimum preparation technology of bis-(biguanide-p-phenyl) methane was studied by orthogonal experiments of three factors and three levels. The results show that the yield of bis-(biguanide-p-phenyl) methane reaches to 85.12% at reaction time of 4h, reaction temperature of 120 °C, mole ratio of 1:2.15. The structures of the compounds were analysed and confirmed by the Infrared spectroscopy and Hydrogen nuclear magnetic spectroscopy. The product is pure without by-products by this way and the modified dicyandiamide had higher reactivity than unmodified dicyandiamide.

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

    PubMed Central

    Cao, Zhiling; Liu, Weiwei; Yin, Fujun

    2010-01-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2013-07-01

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

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

    PubMed Central

    Wang, Ping-An

    2011-01-01

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

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

    PubMed

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

    2005-01-03

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

  16. 2-Phenyl-2,3-dihydro-phenanthro[9,10-b][1,4]dioxine.

    PubMed

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

    2011-02-05

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

  17. 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.

  18. 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.

  19. 3-Hydroxy-2-phenyl-4(1H)-quinolinones as promising biologically active compounds.

    PubMed

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

    2009-06-01

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

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

    PubMed

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

    2015-07-08

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

  1. The thermodynamic parameters of reactions of phenyl isocyanate with methanol associates

    NASA Astrophysics Data System (ADS)

    Samuilov, A. Ya.; Zenitova, L. A.; Levin, Ya. A.; Kurdyukov, A. I.; Samuilov, Ya. D.

    2008-12-01

    The thermodynamic parameters of reactions of phenyl isocyanate with methanol monomer, dimer, and trimer were calculated by the B3LYP and MP2 quantum-chemical methods. The enthalpies and entropies of transformations were found to increase as the degree of methanol association grew. An isokinetic dependence was observed for the transformations under consideration. The influence of the polarity of solvents on the Gibbs energies of these reactions was estimated.

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

    PubMed Central

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

    2014-01-01

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

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

    SciTech Connect

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

    1988-10-20

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

  4. 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.

  5. 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

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

    PubMed

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

    2003-04-03

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

  7. 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.

  8. Benzoxyl radical decomposition kinetics: formation of benzaldehyde + H, phenyl + CH2O, and benzene + HCO.

    PubMed

    da Silva, Gabriel; Bozzelli, Joseph W

    2009-06-25

    The kinetics of benzoxyl radical decomposition was studied using ab initio computational chemistry and RRKM rate theory. The benzoxyl radical is an important but short-lived intermediate in the combustion of toluene and other alkylated aromatic hydrocarbons. A theoretical study of the thermochemistry and kinetics to products over a range of temperatures and pressures for benzoxyl decomposition is reported. Ab initio calculations with the G3X theoretical method reveal low-energy pathways from the benzoxyl radical to benzaldehyde + H and the phenyl radical + formaldehyde (CH(2)O), as well as a novel mechanism to benzene + the formyl radical (HC(*)O). RRKM simulations were performed for benzoxyl decomposition as a function of temperature and pressure. Benzaldehyde formation constitutes more than 80% of the total reaction products at temperatures below 1000 K, decreasing to around 50% at 2000 K. Formation of benzene + HC(*)O and phenyl + CH(2)O is of similar importance, each accounting for 5-10% of the decomposition products at around 1000 K, increasing to 20-30% at 2000 K. The results presented here should lead to improved kinetic models for the oxidation of alkylated aromatic hydrocarbons, particularly for the formation of benzene as a direct oxidation product of toluene. Re-evaluation of the phenyl radical heat of formation leads us to suggest a benzene C-H bond dissociation energy in the range of 113.5-114.5 kcal mol(-1).

  9. 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.

  10. 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

  11. Molecular structure and ring tunneling of phenyl formate as observed by microwave spectroscopy and quantum chemistry

    NASA Astrophysics Data System (ADS)

    Ferres, Lynn; Mouhib, Halima; Stahl, Wolfgang; Schwell, Martin; Nguyen, Ha Vinh Lam

    2017-07-01

    Phenyl formate has been investigated by molecular jet Fourier-transform microwave spectroscopy in the frequency range from 2 to 26.5 GHz. Quantum chemical calculations at the MP2/6-311++G(d,p) level of theory indicate that this molecule does not have a plane of symmetry at equilibrium, and that the phenyl ring performs a large amplitude tunneling motion from one side of the Cs configuration to the other. The tilt angle of the ring out of the Hsbnd (Cdbnd O)O plane is ±70° and the calculated tunneling barrier is only 28 cm-1. The two lowest torsional states vt = 0 and 1 are assigned in the experimental spectrum and fitted using the program SPFIT/SPCAT. The Coriolis splitting ΔE between these states is 46.2231(25) GHz, very close to the value of 48.24 GHz calculated using a simple two-top torsional Hamiltonian of the formate group and the phenyl ring.

  12. 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. Copyright © 2012 Elsevier Ltd. All rights reserved.

  13. 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. Copyright © 2012 Elsevier Ltd. All rights reserved.

  14. 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. Copyright © 2012 Elsevier Ltd. All rights reserved.

  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. Copyright © 2012 Elsevier Ltd. All rights reserved.

  16. 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.

  17. Energetics and electronic structure of phenyl-disubstituted polyacetylene: A first-principles study

    NASA Astrophysics Data System (ADS)

    Sony, Priya; Shukla, Alok; Ambrosch-Draxl, Claudia

    2010-07-01

    Phenyl-disubstituted polyacetylene (PDPA) is an organic semiconductor which has been studied during recent years for its efficient photoluminescence. In contrast, the molecular geometry, providing the basis for the electronic and optical properties has been hardly investigated. In this paper, we apply a density-functional-theory based molecular-dynamics approach to reveal the molecular structure of PDPA in detail. We find that oligomers of this material are limited in length, being stable only up to eight repeat units, while the polymer is energetically unfavorable. These facts, which are in excellent agreement with experimental findings, are explained through a detailed analysis of the bond lengths. A consequence of the latter is the appearance of pronounced torsion angles of the phenyl rings with respect to the plane of the polyene backbone, ranging from 55° up to 95° . We point out that such large torsion angles do not destroy the conjugation of the π electrons from the backbone to the side phenyl rings, as is evident from the electronic charge density.

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

    PubMed

    Beste, Ariana; Buchanan, A C

    2009-04-03

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

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

    PubMed

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

    2009-01-01

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

  20. In vitro biological studies and structural elucidation of fluoro-substituted phenyl acrylic acids.

    PubMed

    Hussain, Mukhtiar; Hanif, Muhammad; Ali, Saqib; Butcher, Ray; Mirza, Tahira; Vanderveer, Don; Aziz-ur-Rehman

    2010-09-01

    Synthesis, characterization, and biological significance of different substituted phenyl acrylic acids have been studied. These acids are contributing a key role during synthesis of antimicrobial drugs. The acids were prepared by condensation of various substituted phenyl acetic acids and aldehydes. o-piperonal was prepared using 2,3-methylenedioxy benzaldehyde. These phenyl acrylic acids were characterized by using analytical techniques, for example, Fourier transform infrared spectroscopy, multinuclear NMR (1H, 13C NMR), and GC-MS. The structure of crystalline products was also elucidated by X-ray crystallography. Small intermolecular and intramolecular weaker interactions were also studied by these characterization techniques. The geometry of compounds in solid and solution state has been studied. The presence of weaker interactions in these molecules is also observed which may increase the hydrolysis and lipophilicity and ultimately improve the activity against different microbes. The effect of different groups attached to the main rings and the presence of smaller interaction have been studied. Their factors may enhance the activity of these compounds.

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

    PubMed Central

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

    2013-01-01

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

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

    PubMed Central

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

    2012-01-01

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

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

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 1 2011-04-01 2011-04-01 false 4- -2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one...-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. (a) Identity. The color additive is 4- -2,4-dihydro-5-methyl-2-phenyl-3H- pyrazol-3-one (CAS Reg. No. 6407-78-9). (b) Uses and restrictions. (1) The substances listed...

  4. 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

    ...-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT... Devices § 73.3122 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. (a) Identity. The color additive is 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H- pyrazol-3-one (CAS...

  5. 40 CFR 721.4040 - Glycols, polyethylene-, 3-sulfo-2-hydroxypropyl-p-(1,1,3,3-tetra-methylbutyl)phenyl ether, sodium...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-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) is...

  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

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

  7. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  8. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  9. 40 CFR 721.10023 - Benzenamine, N-phenyl-, ar ar′-(C9-rich C88-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

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

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  11. Amino substituted analogs of 1-phenyl-3-phenylimino-2-indolones with potent galanin Gal3 receptor binding affinity and improved solubility.

    PubMed

    Konkel, Michael J; Packiarajan, Mathivanan; Chen, Heidi; Topiwala, Upendra P; Jimenez, Hermogenes; Talisman, Ian Jamie; Coate, Heather; Walker, Mary W

    2006-08-01

    A series of amino analogs of 1,3-dihydro-1-phenyl-3-[[3-(trifluoromethyl)phenyl]imino]-2H-indol-2-one (1) were synthesized to improve aqueous solubility, while retaining high affinity for the human galanin Gal3 receptor. A very potent analog (9e, 1,3-dihydro-1-[3-(2-pyrrolidinylethoxy)phenyl]-3-[[3-(trifluoromethyl)phenyl]imino]-2H-indol-2-one, Ki=5 nM) shows good selectivity and solubility of 48 microg/mL at pH 7.4.

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

    NASA Astrophysics Data System (ADS)

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

    2014-12-01

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

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

    PubMed

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

    2015-07-16

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

  14. 17O NMR studies of ortho-substituent effects in substituted phenyl tosylates.

    PubMed

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

    2012-10-01

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

  15. Effects of 3-chloro-phenyl-1,4-dihydropyridine derivatives on Trypanosome cruzi epimastigotes.

    PubMed

    Maya, J D; Morello, A; Repetto, Y; Tellez, R; Rodriguez, A; Zelada, U; Puebla, P; Caballero, E; Medarde, M; Núñez-Vergara, L J; Squella, J A; Bontá, M; Bollo, S; San Feliciano, A

    2000-01-01

    A series of 3-chloro-phenyl-1,4-dihydropyridine derivatives produced different degrees of inhibition of parasite growth and respiration on clone Brener, LQ and Tulahuen strains of Trypanosome cruzi epimastigotes. Respiratory chain inhibition appears to be a posible determinant of the trypanosomicidal activity of this compounds. No difference in the action of these derivatives was found among the different parasite strains. For comparative purposes, the inhibitory effects of felodipine and nicardipine are also reported. A good correlation between toxic effects and the easiness of oxidation of the dihydripyridine ring was found. The presence of a fused ring on the dihydropyridine moiety significantly diminished the inhibitory effects.

  16. Poly[potassium-μ-2-[2-(carboxymethyl)phenyl]acetato

    PubMed Central

    García-Zarracino, Reyes; Rangel-Marrón, Marcela; Tlahuext, Hugo; Höpfl, Herbert

    2008-01-01

    In the title salt, [K(C10H9O4)]n, the K+ ions are coordinated by six O atoms from three different anions, and there is a cation–π inter­action at ca 3.14 Å. The 2-[2-(carboxymethyl)phenyl]acetate anions are stabilized by intramolecular O—H⋯O hydrogen bonds, and the K+ cations are linked into one-dimensional coordination polymers running along the b axis; these are further inter­connected by weak C—H⋯O hydrogen bonds. PMID:21581216

  17. 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.

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

    PubMed

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

    2008-01-18

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

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

    NASA Astrophysics Data System (ADS)

    soni, Namrata; Parsai, Neetu; Mishra, Ashutosh

    2016-10-01

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

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

    SciTech Connect

    Bikkulova, A.T.

    1985-08-20

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

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

    PubMed Central

    Ye, Fei; Fu, Ying; Zhao, Shuang

    2010-01-01

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

  2. N,N-Bis(4-chloro-phenyl-sulfon-yl)succinamide dihydrate.

    PubMed

    Purandara, H; Foro, Sabine; Gowda, B Thimme

    2012-07-01

    The asymmetric unit of the title compound, C(16)H(14)Cl(2)N(2)O(6)S(2)·2H(2)O, contains one half-mol-ecule of N,N-bis-(4-chloro-phenyl-sulfon-yl)succinamide, with a centre of symmetry at the mid-point of the central C-C bond, and one water mol-ecule. The succinamide mol-ecules are not directly connected via hydrogen bonds, but by hydrogen bonds via the water mol-ecules.

  3. 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.

  4. Kresoxim-methyl Derivatives: Synthesis and Herbicidal Activities of (Pyridinylphenoxymethylene)phenyl Methoxyiminoacetates.

    PubMed

    Cao, Yang-Yang; Mao, Da-Jie; Wang, Wei-Wei; Du, Xiao-Hua

    2017-08-02

    A series of new kresoxim-methyl derivatives, (pyridinylphenoxymethylene)phenyl methoxyiminoacetates, were synthesized and their structures were confirmed by NMR and high-resolution mass spectrometry (HRMS). Although derived from a fungicide, the bioassays indicated that several new compounds had good herbicidal activities. At 37.5 g a.i./ha, compound 5c showed 100% inhibition against Abutilon theophrasti, Amaranthus retroflexus, and Eclipta prostrata, which was better than mesotrione. Compound 5e had a broad herbicidal spectrum against broadleaf weeds. The present work indicates that 5c and 5e may serve as new candidates for potential herbicides.

  5. S-Phenyl 4-meth­oxy­benzothio­ate

    PubMed Central

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

    2012-01-01

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

  6. Ethyl N-(2-benzoyl-3-oxo-3-phenyl-propano-yl)carbamate.

    PubMed

    Akkurt, Mehmet; Sarıoğlu, Ahmet Oral; Sönmez, Mehmet; Tahir, Muhammad Nawaz

    2013-02-01

    In the title compound, C(19)H(17)NO(5), the dihedral angle between the phenyl groups is 79.55 (15)°. The terminal eth-oxy group is disordered over two orientations in a 0.873 (6):0.127 (6) ratio. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into [001] chains which incorporate R(1) (2)(6) loops. A very weak C-H⋯π contact also occurs.

  7. Ethyl N-(2-benzoyl-3-oxo-3-phenyl­propano­yl)carbamate

    PubMed Central

    Akkurt, Mehmet; Sarıoğlu, Ahmet Oral; Sönmez, Mehmet; Tahir, Muhammad Nawaz

    2013-01-01

    In the title compound, C19H17NO5, the dihedral angle between the phenyl groups is 79.55 (15)°. The terminal eth­oxy group is disordered over two orientations in a 0.873 (6):0.127 (6) ratio. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into [001] chains which incorporate R 1 2(6) loops. A very weak C—H⋯π contact also occurs. PMID:23424501

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

    NASA Astrophysics Data System (ADS)

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

    2008-01-01

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

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

    DTIC Science & Technology

    1984-10-01

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

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

    DTIC Science & Technology

    1984-10-01

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

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

    PubMed

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

    2005-10-05

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

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

    PubMed

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

    2014-04-23

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

  13. Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones.

    PubMed

    Narasimhan, Balasubramanian; Sharma, Deepika; Kumar, Pradeep; Yogeeswari, Perumal; Sriram, Dharmarajan

    2011-10-01

    A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (1-11) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (12-20) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol-1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC] = 3.13 µg) was equipotent as standard drug ciprofloxacin and [2-(4-Nitro-phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC = 1.56 µg) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC = 0.002 µg) was two times more effective than standard drug ciprofloxacin (MIC = 0.004 µg) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)-imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC = 0.005 µg) was equipotent to the reference compound, fluconazole against tested fungal strains.

  14. 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.

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

    PubMed Central

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

    2010-01-01

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

  16. 2-[(1R,3S)-6,7-Dimeth­oxy-1-phenyl-1,2,3,4-tetra­hydro­isoquinolin-3-yl]-4-phenyl-1,3-thia­zole

    PubMed Central

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

    2011-01-01

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

  17. 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.

  18. (3R,4S)-3-Methyl-4-phenyl-2-[(R)-1-phenyl­eth­yl]-3,4-di­hydro­isoquinolin-2-ium tetra­fluorido­borate

    PubMed Central

    Ben Ali, Karim; Retailleau, Pascal

    2014-01-01

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

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

    PubMed

    Hsu, Liang-Yan; Rabitz, Herschel

    2012-11-02

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

  20. 1-Ethyl-2-phenyl-3-[2-(tri-methyl-sil-yl)ethyn-yl]-1H-indole.

    PubMed

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

    2013-06-01

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

  1. Separation Differences Among Phenyl Hydride, UDC Cholesterol and Bidentate C8 Stationary Phases for Stability Indicating Methods of Tetracyclines

    PubMed Central

    Young, Joshua E.; Matyska, Maria T.; Azad, Anil K.; Yoc, Sergio E.; Pesek, Joseph J.

    2014-01-01

    Formulation extracts of tetracycline hydrochloride (HCl), minocycline hydrochloride (HCl), and doxycycline hyclate were degraded by strong acidic conditions and heating. Subsequently, components of the extracts were separated by Bidentate C8, Phenyl Hydride and Cholesterol (UDC) HPLC columns operating in the reverse phase mode. The Phenyl Hydride column was able to baseline separate minocycline from the observed degradant, while partial or total co-elution was observed with the other two columns using otherwise identical method conditions. For both the degraded tetracycline HCl and doxycycline hyclate extracts, the UDC column gave the best resolution for the critical pair. The findings suggest that the postulated secondary retention mechanisms of π–π interactions from the Phenyl Hydride and shape selectivity from the UDC can provide superior resolution for structurally similar analytes compared to hydrophobic interactions alone. PMID:24748763

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

    SciTech Connect

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

    1991-01-01

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

  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.

  4. 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. Copyright © 2013 Elsevier GmbH. All rights reserved.

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

    PubMed

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

    2013-12-01

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

  6. Preparation and Characterization of Flexible Substrate Material from Phenyl-Thiophene-2-Carbaldehyde Compound

    PubMed Central

    Rahman, Ashiqur; Islam, Mohammad Tariqul; Samsuzzaman, Md; Singh, Mandeep Jit; Akhtaruzzaman, Md.

    2016-01-01

    In this paper, a novel phenyl-thiophene-2-carbaldehyde compound-based flexible substrate material has been presented. Optical and microwave characterization of the proposed material are done to confirm the applicability of the proposed material as a substrate. The results obtained in this work show that the phenyl-thiophene-2-carbaldehyde consists of a dielectric constant of 3.03, loss tangent of 0.003, and an optical bandgap of 3.24 eV. The proposed material is analyzed using commercially available EM simulation software and validated by the experimental analysis of the flexible substrate. The fabricated substrate also shows significant mechanical flexibility and light weight. The radiating copper patch deposited on the proposed material substrate incorporated with partial ground plane and microstrip feeding technique shows an effective impedance bandwidth of 3.8 GHz. It also confirms an averaged radiation efficiency of 81% throughout the frequency band of 5.4–9.2 GHz. PMID:28773479

  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

    2016-06-03

    In this work, two new types of polycyclic aromatic grafted polysiloxanes, namely, 3,4-bis(4-fluoro phenyl)-2,5-diphenyl polysiloxane (FPP) and 3,4-bis(3,4,5-trifluoro phenyl)-2,5-diphenyl polysiloxane (TFPP), were synthesized and statically coated onto capillary columns as stationary phases for gas chromatography (GC). Based on their McReynolds constants, both columns exhibited moderate polarity. The efficiencies of the FPP and TFPP columns were 3316 (k=3.96, naphthalene; 0.25mm inner diameter) and 3768 (k=4.14, naphthalene; 0.25mm inner diameter) plates/m, respectively. The thermostability of the polymers was tested by thermogravimetric analysis (TGA), and results revealed that both TFPP and FPP began to decompose slightly at 380°C. Separation of polyethylene pyrolysis products showed that the upper working temperature of the two columns can reach up to 360°C. Relying on their unique polarizable characteristics in combination with other types of interactions, such as H-bond acceptor, dipole-dipole, and dispersive interactions, the newly synthesized polarizable stationary phases offered unique selectivity for aromatic isomers and substituted benzenes. A slight separation difference between TPP and TFPP was observed. TFPP also exerted excellent selectivity for polycyclic aromatic hydrocarbons, fatty acid esters, and fatty alcohols. Overall, FPP and TFPP demonstrated considerable potential for further applications because of their unique structures and outstanding separation performance. Copyright © 2016 Elsevier B.V. All rights reserved.

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

    PubMed Central

    Devendran, Saravanan; Yadav, Ganapati D.

    2014-01-01

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

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

    PubMed

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

    2016-03-07

    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. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. The Influence of Alkoxy Substitutions on the Properties of Diketopyrrolopyrrole-Phenyl Copolymers for Solar Cells

    PubMed Central

    George, Zandra; Kroon, Renee; Gehlhaar, Robert; Gbabode, Gabin; Lundin, Angelica; Hellström, Stefan; Müller, Christian; Geerts, Yves; Heremans, Paul; Andersson, Mats R.

    2013-01-01

    A previously reported diketopyrrolopyrrole (DPP)-phenyl copolymer is modified by adding methoxy or octyloxy side chains on the phenyl spacer. The influence of these alkoxy substitutions on the physical, opto-electronic properties, and photovoltaic performance were investigated. It was found that the altered physical properties correlated with an increase in chain flexibility. Well-defined oligomers were synthesized to verify the observed structure-property relationship. Surprisingly, methoxy substitution on the benzene spacer resulted in higher melting and crystallization temperatures in the synthesized oligomers. This trend is not observed in the polymers, where the improved interactions are most likely counteracted by the larger conformational possibilities in the polymer chain upon alkoxy substitution. The best photovoltaic performance was obtained for the parent polymer: fullerene blends whereas the modifications on the other two polymers result in reduced open-circuit voltage and varying current densities under similar processing conditions. The current densities could be related to different polymer: fullerene blend morphologies. These results show that supposed small structural alterations such as methoxy substitution already significantly altered the physical properties of the parent polymer and also that oligomers and polymers respond divergent to structural alterations made on a parent structure. PMID:28811420

  11. 4-Phenyl quinoline derivatives as potential serotonin receptor ligands with antiproliferative activity.

    PubMed

    Joshi, Pranaya V; Sayed, Alim A; RaviKumar, Ameeta; Puranik, Vedavati G; Zinjarde, Smita S

    2017-08-18

    Antagonists of signaling receptors are often effective non-toxic therapeutic agents. Over the years, there have been evidences describing the role of serotonin or 5-hydroxytryptamine (5-HT) in development of cancer. Although there are reports on the antiproliferative effects of some serotonin receptor antagonists, there are very few investigations related to understanding their structure-activity relationships. In this study, we report the screening of a library of 4-phenyl quinoline derivatives for their antiproliferative activities. Preliminary docking studies indicated that these ligands had the ability to bind to two of the serotonin receptors, 5-HT1B and 5-HT2B. The results of the in silico experiments were validated by performing in vitro studies on MCF-7 breast cancer cell line. The ethylpiperazine derivatives showed maximum toxicity against this cancer cell line. The compounds inhibited Calcium ion efflux (induced by serotonin) and ERK activation. One of the most active 4-phenyl quinoline derivatives (H3a) also induced apoptosis, thereby, suggesting the use of this scaffold as a potential anticancer drug. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

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

    SciTech Connect

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

    2009-02-04

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

  13. Solution photochemistry of [p-(dimethylamino)phenyl]pentazole (DMAPP) at 193 and 300 nm.

    PubMed

    Bazanov, B; Haas, Y

    2015-03-19

    The photochemistry of [p-(dimethylamino)phenyl]pentazole (DMAPP) at 193 nm and in the near UV is reported, with emphasis on the nature of the final stable products. The (dimethylamino)phenyl azide (DMAPA) is found as a major product in MeCN, but not in dichloromethane (DCM). (In this paper the acronyms DMAPP and DMAPA refer to the para isomers.) The photochemistry of DMAPA is also explored for comparison. The data obtained in MeCN solutions are consistent with the initial formation of the corresponding nitrene, but in DCM, different products are found, on the basis of NMR data. In the case of high reactant concentration in DCM (10(-2) M), quantitative conversion of DMAPP and DMAPA is observed, indicating a high quantum yield. In contrast, MeCN solutions react much more slowly. A radical-type chain reaction mechanism is proposed to account for this observation. At high dilution, DMAPP is completely converted to products in both solvents. Possible mechanisms accounting for these results are discussed.

  14. 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.

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

    PubMed

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

    2012-12-28

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

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

    PubMed

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

    2017-01-06

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

  17. 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.

  18. 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one

    PubMed Central

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

    2012-01-01

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

  19. Spectroscopic and thermal studies on 2- and 4-phenyl-1H-imidazoles

    NASA Astrophysics Data System (ADS)

    Hachuła, Barbara; Polasz, Anna; Książek, Maria; Kusz, Joachim; Starczewska, Oliwia; Pisarski, Wojciech

    2017-08-01

    The polarized IR spectra of isotopically neat and isotopically substituted monocrystalline samples of 2-phenyl-1H-imidazole (2PI) and 4-phenyl-1H-imidazole (4PI) were recorded at two temperatures of 293 K and 77 K. The room-temperature ATR-FTIR and Raman spectra of 2PI and two polymorphic forms of 4PI were also recorded. Theoretical analysis of the vibrational spectra of selected imidazole derivatives reflected similar characteristics of their hydrogen-bond networks and allowed us to obtain the information about the mechanism of the H/D isotopic ;self-organization; phenomenon. The distribution of protons and deuterons in the lattices of the isotopically diluted crystalline samples of 2PI and 4PI was found to be non-random. In the crystals of the hydrogen- and deuterium-bonded imidazole derivatives the strongest vibrational exciton interactions favored the intrachain (;tail-to-head;)-type exciton coupling widespread at 77 K via the π-electrons. At room temperature a weak interchain (;through-space;)-type exciton coupling was also partially responsible for the IR spectra generation. Differential scanning calorimetry (DSC) measurements showed that the two polymorphic forms of 4PI exhibit an extensive supercooling of crystallization process and cold crystallization on reheating. Additionally, both polymorphic modifications of 4PI are monotropically related. 2PI exhibits only the crystallization and melting processes.

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

    PubMed

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

    2017-02-01

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

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

    SciTech Connect

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

    2007-08-15

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

  2. 6-Butyryl-5-hy­droxy-4-phenyl­seselin

    PubMed Central

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

    2010-01-01

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

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

    PubMed

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

    2015-12-01

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

  4. 2,3,5-Triphenyl-2H-tetra­zol-3-ium tetra­phenyl­borate

    PubMed Central

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

    2012-01-01

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

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

    PubMed

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

    2010-11-27

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

  6. 2-Carbaborane-3-phenyl-1H-indoles--synthesis via McMurry reaction and cyclooxygenase (COX) inhibition activity.

    PubMed

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

    2013-02-01

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

  7. A newly Synthesis and characterization of metal complexes of 3-(N- phenyl) thiourea-pentanone-2 as ligand

    NASA Astrophysics Data System (ADS)

    Mishra, A.; Ninama, S.; Sharma, P.; Soni, N.; Awate, R.

    2012-05-01

    Present communication deals with the synthesis of copper and cobalt complexes derived from 3-(N- phenyl) thiourea-pentanone-2 as the ligand. Structure of all the compounds was characterized by elemental, XRD, FTIR, UV-VIS, SEM and 1HNMR spectroanalytical studies. The X-ray diffraction studies indicate that 3-(N- phenyl) thiourea-pentanone-2 and their complexation with copper and cobalt metals are crystalline in nature. The FTIR spectroscopic data were used to assign the characteristic vibrational frequencies of various groups present in the compounds. Scanning electron Micrograms were used to assign the morphology and particle size of the compounds.

  8. 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... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a...

  9. 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... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a...

  10. 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... (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10080 Carbon black, 4- phenyl-modified, hydrochlorides (generic). (a...

  11. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  12. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  13. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

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

  14. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

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

  15. 40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  16. 1-Phenyl-1-propyne on Cu(111): TOFMS TPD, XPS, UPS, and 2PPE Studies.

    PubMed

    Sohn, Youngku; Wei, Wei; White, John M

    2007-11-20

    The bonding properties of 1-phenyl-1-propyne (PP, C6H5CCCH3) on Cu(111) at 100 K have been studied using temperature-programmed desorption (TPD), and X-ray, ultraviolet, and two-photon photoemission spectroscopies (XPS, UPS, and 2PPE). In TPD, there is no evidence for dissociation. Multilayer desorption occurs at 187 K, and monolayer desorption occurs at 320 (83.5 kJ/mol) and 390 K (102.4 kJ/mol), with the latter dominating. Based on the calibrated C(1s) XPS, the saturation monolayer coverage is one PP per four surface Cu atoms. The broad and asymmetric C(1s) intensity profile of the monolayer can be resolved into three symmetric components, with peaks at 283.6, 284.5, and 285.2 eV and intensities of 2:6:1, respectively. These are attributed, respectively, to acetylenic carbons bound to Cu, phenyl, and methyl carbons. The monolayer valence band ultraviolet photoemission spectrum profile contains four resonances attributable to PP perturbed by interactions with the Cu(111) substrate. With the exception of the highest occupied molecular orbital (HOMO) that is shifted by 0.4 eV, these are uniformly shifted by 1 eV further from the Fermi level for the multilayer. Calculated electron density plots of the occupied orbitals coupled with UPS profiles suggest a spectator role for the phenyl group and bonding to Cu via the acetylenic carbons. The adsorption of 1.0 monolayer (ML) of PP on Cu(111) lowers the work function by 0.85 eV. Using 2PPE, two unoccupied orbitals were identified at 1.0 (U1*-LUMO) and 0.6 eV (U2*-image state) below the vacuum level. A chemisorption model consistent with these spectroscopic results and the major chemisorption peak in TPD involve di-sigma-bonding of the acetylenic carbons to a pair of second-nearest neighbor surface Cu atoms (cross-bridge).

  17. Controlling the Conformational Energy of a Phenyl Group by Tuning the Strength of a Nonclassical CH···O Hydrogen Bond: The Case of 5-Phenyl-1,3-dioxane.

    PubMed

    Bailey, William F; Lambert, Kyle M; Stempel, Zachary D; Wiberg, Kenneth B; Mercado, Brandon Q

    2016-12-16

    Anancomeric 5-phenyl-1,3-dioxanes provide a unique opportunity to study factors that control conformation. Whereas one might expect an axial phenyl group at C(5) of 1,3-dioxane to adopt a conformation similar to that in axial phenylcyclohexane, a series of studies including X-ray crystallography, NOE measurements, and DFT calculations demonstrate that the phenyl prefers to lie over the dioxane ring in order to position an ortho-hydrogen to participate in a stabilizing, nonclassical CH···O hydrogen bond with a ring oxygen of the dioxane. Acid-catalyzed equilibration of a series of anancomeric 2-tert-butyl-5-aryl-1,3-dioxane isomers demonstrates that remote substituents on the phenyl ring affect the conformational energy of a 5-aryl-1,3-dioxane: electron-withdrawing substituents decrease the conformational energy of the aryl group, while electron-donating substituents increase the conformational energy of the group. This effect is correlated in a very linear way to Hammett substituent parameters. In short, the strength of the CH···O hydrogen bond may be tuned in a predictable way in response to the electron-withdrawing or electron-donating ability of substituents positioned remotely on the aryl ring. This effect may be profound: a 3,5-bis-CF3 phenyl group at C(5) in 1,3-dioxane displays a pronounced preference for the axial orientation. The results are relevant to broader conformational issues involving heterocyclic systems bearing aryl substituents.

  18. 1-Phenyl-3-methyl-4-benzoylpyrazol-5-one as a group-extraction reagent for spectrophotometric determination of trace elements.

    PubMed

    Mirza, M Y; Nwabue, F I

    1981-01-01

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

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

    PubMed

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

    2009-12-01

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

  20. Synthesis and Properties of Phenylated Aromatic Heterocyclic Imide and Thiazole Polymers Containing Pendant Diphenylether and Diphenylsulfide Groups.

    DTIC Science & Technology

    1983-10-01

    1 11 RESULTS AND DISCUSSION 2 1 . Synthesis 3 a...Monomers 3 b. Polymers 6 2 . Properties 6 a. Polymer Solubility 6 b. Thermal Mechanical Behavior 8 c. Thermal Evaluation 8 III EXPERIMENTAL 10 1 ...Two isomeric acetylenic benzothiazole monomers, 2 -(ethynylphenyl)- 5-ethynyl benzothiazol e and 2 -( 3 -ethynyl phenyl )-6-ethynyl benzothiazol e

  1. 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.

  2. 40 CFR 721.5930 - Phenylenebis[imino (chlorotriazinyl)imino(substituted naphthyl)azo(substituted phenyl)azo, sodium...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  3. A Combination of Guanidyl and Phenyl Groups on a Dendrimer Enables Efficient siRNA and DNA Delivery.

    PubMed

    Chang, Hong; Zhang, Jia; Wang, Hui; Lv, Jia; Cheng, Yiyun

    2017-08-14

    Gene therapy has received considerable attention due to its great potential in the treatment of various diseases; however, the design of efficient and biocompatible carriers for the delivery of siRNA as well as DNA still remains a major challenge. In this study, we developed an efficient carrier for gene delivery by modification of a compound containing both guanidyl and phenyl groups on the surface of a cationic dendrimer. The guanidyl group on the dendrimer facilitates nucleic acid condensation via specific guanidinium-phosphate interactions, whereas the phenyl group on the polymer is critical for efficient endosomal escape. The combination of guanidyl and phenyl shows a synergistic effect in facilitated endocytosis. The designed material is much more efficient in siRNA and DNA delivery than control materials such as dendrimers engineered with a guanidyl or phenyl group only, as well as intact dendrimers, and shows comparable efficacy to commercial transfection reagent Lipofectamine 2000. In addition, the material and its complex with nucleic acid show minimal toxicity on the transfected cells. This study provides a new strategy to develop multifunctional polymers for efficient siRNA and DNA delivery.

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

    PubMed

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

    2017-03-10

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

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

    PubMed

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

    2007-02-15

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

  6. 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 to...

  7. 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 to...

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

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

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

    Code of Federal Regulations, 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 to...

  10. 2-(1,3-Benzoxazol-2-ylsulfan-yl)-1-phenyl-ethanone.

    PubMed

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

    2009-08-29

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

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

    PubMed

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

    2014-01-03

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

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

    NASA Astrophysics Data System (ADS)

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

    2015-04-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2017-01-01

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

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

    PubMed

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

    2005-01-01

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

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

    SciTech Connect

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

    1994-09-01

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

  16. Structure Based Development of Phenyl-imidazole-derived Inhibitors of Indoleamine 2,3-Dioxygenase

    PubMed Central

    Kumar, Sanjeev; Jaller, Daniel; Patel, Bhumika; LaLonde, Judith M.; DuHadaway, James B.; Malachowski, William P.; Prendergast, George C.; Muller, Alexander J.

    2011-01-01

    Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. With the goal of developing more potent IDO inhibitors, a systematic study of 4-phenyl-imidazole (4-PI) derivatives was undertaken. Computational docking experiments guided design and synthesis efforts with analogs of 4-PI. In particular, three interactions of 4-PI analogs with IDO were studied: the active site entrance, the interior of the active site and the heme iron binding. The three most potent inhibitors (1, 17 and 18) appear to exploit interactions with C129 and S167 in the interior of the active site. All three inhibitors are approximately ten-fold more potent than 4-PI. The study represents the first example of enzyme inhibitor development with the recently reported crystal structure of IDO and offers important lessons in the search for more potent inhibitors. PMID:18665584

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

    PubMed Central

    Smith, Graham; Wermuth, Urs D.

    2010-01-01

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

  18. 2-Chloro-N-(3,5-dichloro­phenyl)­benzamide

    PubMed Central

    Gowda, B. Thimme; Foro, Sabine; Sowmya, B. P.; Fuess, Hartmut

    2008-01-01

    The amide group in the structure of the title compound (N35DCP2CBA), C13H8Cl3NO, is trans-planar, similar to that observed in N-(3-chloro­phen­yl)benzamide, N-(3,5-dichloro­phen­yl)benzamide, 2-chloro-N-phenyl­benzamide and other benzanilides. The C=O bond in N35DCP2CBA is anti to the ortho-chloro substituent in the benzoyl ring. The amide group makes dihedral angles of 63.1 (12) and 31.1 (17)°, respectively, with the benzoyl and aniline benzene rings, while the dihedral angle between the two benzene rings is 32.1 (2)°. The mol­ecules are linked into chains along the b axis by N—H⋯O hydrogen bonds. PMID:21202924

  19. 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.

  20. 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.

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

    PubMed

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

    1999-01-01

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

  2. Dicyclo­hexyl­ammonium (S)-2-azido-3-phenyl­propano­ate

    PubMed Central

    Petrik, Sebastian J.; Brown, Christopher L.; Boyd, Sue E.; Healy, Peter C.

    2012-01-01

    The asymmetric unit of the title compound, C12H24N+·C9H8N3O2 −, consists of two dicyclo­hexyl­ammonium cations linked to two (S)-2-azido-3-phenyl­propano­ate anions by four short N—H⋯O hydrogen bonds with N⋯O distances in the range 2.712 (3)–2.765 (3) Å. The dicyclo­hexyl­ammonium cations and the aryl and carboxyl­ate groups of the anion are related by a pseudo-inversion centre, with overall crystallographic inversion symmetry for the structure broken by the chirality of the α-C atoms of the anions. PMID:22807875

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

    PubMed

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

    1996-01-31

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

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

    SciTech Connect

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

    1996-10-01

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

  5. Dicyclo-hexyl-ammonium (S)-2-azido-3-phenyl-propano-ate.

    PubMed

    Petrik, Sebastian J; Brown, Christopher L; Boyd, Sue E; Healy, Peter C

    2012-07-01

    The asymmetric unit of the title compound, C(12)H(24)N(+)·C(9)H(8)N(3)O(2) (-), consists of two dicyclo-hexyl-ammonium cations linked to two (S)-2-azido-3-phenyl-propano-ate anions by four short N-H⋯O hydrogen bonds with N⋯O distances in the range 2.712 (3)-2.765 (3) Å. The dicyclo-hexyl-ammonium cations and the aryl and carboxyl-ate groups of the anion are related by a pseudo-inversion centre, with overall crystallographic inversion symmetry for the structure broken by the chirality of the α-C atoms of the anions.

  6. Block-Localized Wavefunction (BLW) Based Two-State Approach for Charge Transfers between Phenyl Rings.

    PubMed

    Mo, Yirong; Song, Lingchun; Lin, Yuchun; Liu, Minghong; Cao, Zexing; Wu, Wei

    2012-03-13

    The block-localized wave function (BLW) method is the simplest and most efficient variant of ab initio valence bond (VB) theory which defines electron-localized resonance states following the conventional VB concepts. Here, a BLW-based two-state approach is proposed to probe the charge/hole transfer reactions within the Marcus-Hush model. With this approach, both the electronic coupling and reorganization energies can be derived at the ab initio level. Pilot applications to the electron/hole transfers between two phenyl rings are presented. Good exponential correlation between the electronic coupling energy and the donor-acceptor distance is shown, whereas the inner-sphere reorganization shows little geometric dependency. Computations also support the assumption in Marcus theory that the thermal electron transfer barrier (ΔG*), which is a sum of the reaction barrier (ΔEa) for electron/hole transfer and the coupling energy (VAB), is a quarter of the reorganization energy (λ).

  7. 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.

  8. Conformations and steric and stacking interactions of trisubstituted ureas and thioureas with alkyl and phenyl groups

    NASA Astrophysics Data System (ADS)

    Mido, Yoshiyuki; Okada, Hiroko; Itoh, Tamotsu

    1980-08-01

    The monomeric ν(N—H) vibrations of various trisubstituted ureas of the R 2UPh type and -thioureas of the R 2TUPh type have been studied. The trans—out isomerism in the former and the trans—out— cis isomerism in the latter are discussed from the point of view of steric effect. The monomeric ν(N—H) vibrations of RPhUPh and RPhTUPh are also examined. The single band appearing in the spectrum of both ureas is characteristic of the cis form; this suggests the existence of phenyl—phenyl interaction (the stacking interaction proposed by Galabov et al. [10]). Behavior of ν(N—H) vibrations at several concentrations is shown to be clearly different in the three forms ( trans, out and cis). The presence of the cis form is confirmed by solvent effect experiments.

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

    NASA Astrophysics Data System (ADS)

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

    2015-12-01

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

  10. 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.

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

    SciTech Connect

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

    2007-01-01

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

  12. (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.

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

    PubMed Central

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

    2016-01-01

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

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

    PubMed

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

    2012-04-16

    Intramolecular π-π stacking interaction in one kind of phosphorescent cationic iridium complexes has been controlled through fluorination of the pendant phenyl rings on the ancillary ligands. Two blue-green-emitting cationic iridium complexes, [Ir(ppy)(2)(F2phpzpy)]PF(6) (2) and [Ir(ppy)(2)(F5phpzpy)]PF(6) (3), with the pendant phenyl rings on the ancillary ligands substituted with two and five fluorine atoms, respectively, have been synthesized and compared to the parent complex, [Ir(ppy)(2)(phpzpy)]PF(6) (1). Here Hppy is 2-phenylpyridine, F2phpzpy is 2-(1-(3,5-difluorophenyl)-1H-pyrazol-3-yl)pyridine, F5phpzpy is 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)-pyridine, and phpzpy is 2-(1-phenyl-1H-pyrazol-3-yl)pyridine. Single crystal structures reveal that the pendant phenyl rings on the ancillary ligands stack to the phenyl rings of the ppy ligands, with dihedral angles of 21°, 18°, and 5.0° between least-squares planes for complexes 1, 2, and 3, respectively, and centroid-centroid distances of 3.75, 3.65, and 3.52 Å for complexes 1, 2, and 3, respectively, indicating progressively reinforced intramolecular π-π stacking interactions from complexes 1 to 2 and 3. Compared to complex 1, complex 3 with a significantly reinforced intramolecular face-to-face π-π stacking interaction exhibits a significantly enhanced (by 1 order of magnitude) photoluminescent efficiency in solution. Theoretical calculations reveal that in complex 3 it is unfavorable in energy for the pentafluorophenyl ring to swing by a large degree and the intramolecular π-π stacking interaction remains on the lowest triplet state. © 2012 American Chemical Society

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

    PubMed

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

    2011-01-01

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

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

    PubMed

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

    2013-01-07

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

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

    PubMed

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

    2001-07-12

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

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

    PubMed

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

    2008-12-15

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

  19. (1′S,2R,3R)-(−)-2-Hydr­oxy-3-morpholino-3-phenyl-N-(1′-phenyl­ethyl)propion­amide

    PubMed Central

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

    2009-01-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2013-05-01

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

  1. Synthesis and Mossbauer spectroscopic studies of chemically oxidized ferrocenyl(phenyl)phosphines.

    PubMed

    Durfey, D A; Kirss, R U; Frommen, C; Feighery, W

    The electrochemical potentials of Fc3-xPPhx, (1-3, x = 0-2) and (FcPPh)n (4) indicate that iodine should oxidize ferrocenyl(phenyl)phosphines. The molar conductivity of solutions of 1-3 increases sharply when the solutions are titrated with iodine, leveling off after the addition of > 2 equiv of oxidant, consistent with formation of 1:1 electrolytes. Diamagnetic salts 6-9 are observed upon addition of a benzene solution of iodine to a benzene solution of 1-4 at ambient temperature in ratios of I2/metallocene ranging from 1:1 to 2:1. Well-resolved 1H and 31P NMR spectra are obtained for 6-8. Absorptions assigned to the I3- anion dominate the UV-vis spectrum of 6-8, whereas characteristic absorptions for [Fc][I3] are absent. Mossbauer spectra of 7-9 reveal isomer shifts consistent with low-spin iron(II) in ferrocene derivatives rather than those in ferricenium ions. Small amounts of low-spin FeIII appear to be present in 6. Taken together, the results suggest that 6-9 are iodophosphonium salts and not ferricenium salts. Diferrocenyl(phenyl)phosphine oxide (5) reacts with iodine to produce a diamagnetic, dark solid 10. Low-spin FeII is observed at 77 and 293 K in the Mossbauer spectra of 10 with no evidence for oxidation of FeII to FeIII. Compound 10 is proposed to be a neutral complex between 5 and I2. Reactions between 5 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) yield [Fc2P(=O)][DDQ]2 (11). Mossbauer spectroscopy of 11 indicates the presence of a mixture of low-spin FeII and low-spin FeIII at 77 K, suggesting that some electron transfer occurs from 5 to DDQ. The fraction of low-spin FeIII increases at room temperature.

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

    PubMed

    Kitagawa, Daichi; Kobatake, Seiya

    2014-05-01

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

  3. Crystal structure of [N,N-bis-(di-phenyl-phospho-ro-thio-yl)amidato-κ(2)S,S']bis-(tri-phenyl-phosphane-κP)copper(I) di-chloro-methane monosolvate.

    PubMed

    Nishi, Tatsuya; Tsukuda, Toshiaki; Nishikawa, Michihiro; Tsubomura, Taro

    2017-07-01

    The title compound, [Cu(C24H20NP2S2)(C18H15P)2]·CH2Cl2 or [Cu(dppaS2)(PPh3)2]·CH2Cl2, is a neutral mononuclear copper(I) complex bearing an N,N-bis-(di-phenyl-phospho-rothio-yl)amidate (dppaS2(-)) ligand and two tri-phenyl-phosphane ligands. The molecular structure shows that the two S atoms of the dppaS2(-) ligand [Cu-S = 2.3462 (9) and 2.3484 (9) Å] and the two P atoms of the two tri-phenyl-phosphane ligands [Cu-P = 2.3167 (9) and 2.2969 (9) Å] coordinate to the copper(I) atom, resulting in a tetra-hedral coordination geometry. The crystallographically observed mol-ecular structure is compared to the results of DFT calculations.

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

    NASA Astrophysics Data System (ADS)

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

    2012-03-01

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

  5. 2-(4-Chloro­phen­yl)-4-phenyl-1,2-di­hydro­quinazoline

    PubMed Central

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

    2013-01-01

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

  6. 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

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

    NASA Astrophysics Data System (ADS)

    Faghihi, Khalil; Shabanian, Meisam; Dadfar, Ehsan

    2012-02-01

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

  8. A novel enantioselective epoxide hydrolase for (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol.

    PubMed

    Wu, Shijin; Shen, Jiajia; Zhou, Xiaoyun; Chen, Jianmeng

    2007-10-01

    Bacillus sp. Z018, a novel strain producing epoxide hydrolase, was isolated from soil. The epoxide hydrolase catalyzed the stereospecific hydrolysis of (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol. Epoxide hydrolase from Bacillus sp. Z018 was inducible, and (R)-phenyl glycidyl ether was able to act as an inducer. The fermentation conditions for epoxide hydrolase were 35 degrees C, pH 7.5 with glucose and NH(4)Cl as the best carbon and nitrogen source, respectively. Under optimized conditions, the biotransformation yield of 45.8% and the enantiomeric excess of 96.3% were obtained for the product (R)-3-phenoxy-1,2-propanediol.

  9. Synthesis and SAR of (piperazin-1-yl-phenyl)-arylsulfonamides: a novel series of atypical antipsychotic agents.

    PubMed

    Park, Chul Min; Kim, So Young; Park, Woo Kyu; Choi, Jung Hwan; Seong, Churl Min

    2010-09-01

    (Piperazin-1-yl-phenyl)-arylsulfonamides were synthesized and identified to show high affinities for both 5-HT(2C) and 5-HT(6) receptors. Among them, naphthalene-2-sulfonic acid isopropyl-[3-(4-methyl-piperazin-1-yl)-phenyl]-amide (6b) exhibits the highest affinity towards both 5-HT(2C) (IC(50)=4 nM) and 5-HT(6) receptors (IC(50)=3 nM) with good selectivity over other serotonin (5-HT(1A), 5-HT(2A), and 5-HT(7)) and dopamine (D(2)-D(4)) receptor subtypes. In 5-HT(2C) and 5-HT(6) receptor functional assays, this compound showed considerable antagonistic activity for both receptors.

  10. 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

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

    PubMed

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

    2016-12-26

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

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

    PubMed

    Pruett, S B; Chambers, J E

    1988-01-01

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

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

    PubMed Central

    Gessner, Viktoria H.

    2014-01-01

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

  14. 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.

  15. 2-Carbaborane-3-phenyl-1H-indoles – Synthesis via McMurry Reaction and COX Inhibition Activity

    PubMed Central

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

    2013-01-01

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

  16. Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives.

    PubMed

    Tabatabai, Sayyed Abbas; Barghi Lashkari, Saoka; Zarrindast, Mohammad Reza; Gholibeikian, Mohammadreza; Shafiee, Abbas

    2013-01-01

    Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conformers of the compounds on estazolam, a known benzodiazepine agonist, reveal that the main proposed benzodiazepine pharmacophores were well matched. Anticonvulsant activity of the synthesized compounds, determined by pentylenetetrazole-induced lethal convulsion test, showed that the introduction of an amino substituent in position 5 of 1,3,4- oxadiazole ring generates compound 9 which has a respectable effect. The results are in agreement with SAR of benzodiazepine receptor ligands since the elimination of electronegative substituent in position 2 of phenoxy ring or position 4 of phenyl ring reduces the anticonvulsant activity.

  17. Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives

    PubMed Central

    Tabatabai, Sayyed Abbas; Barghi Lashkari, Saoka; Zarrindast, Mohammad Reza; Gholibeikian, Mohammadreza; Shafiee, Abbas

    2013-01-01

    Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conformers of the compounds on estazolam, a known benzodiazepine agonist, reveal that the main proposed benzodiazepine pharmacophores were well matched. Anticonvulsant activity of the synthesized compounds, determined by pentylenetetrazole-induced lethal convulsion test, showed that the introduction of an amino substituent in position 5 of 1,3,4- oxadiazole ring generates compound 9 which has a respectable effect. The results are in agreement with SAR of benzodiazepine receptor ligands since the elimination of electronegative substituent in position 2 of phenoxy ring or position 4 of phenyl ring reduces the anticonvulsant activity. PMID:24250678

  18. 2-Phenyl-2,3-dihydro­phenanthro[9,10-b][1,4]dioxine

    PubMed Central

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

    2011-01-01

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

  19. 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.

  20. 2-[(E)-(2-Phenyl-2H-1,2,3-triazol-4-yl)methyl-eneamino]ethanol.

    PubMed

    Dang, Yan-Qiu; Tian, Lai-Jin

    2009-03-11

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

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

    PubMed

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

    2011-08-01

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

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

    PubMed

    Basheer, Ahmad; Rappoport, Zvi

    2008-01-04

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

  3. Iron-promoted intramolecular [4 + 2] Diels-Alder cycloadditions of 1-phenyl-3,4-dimethylphosphole with selected dienophiles

    SciTech Connect

    Bhaduri, D.; Nelson, J.H. ); Day, C.L.; Jacobson, R.A. ); Solujic, L.; Milosavljevic, E.B. )

    1992-12-01

    The complex [([eta][sup 5]-C[sub 5]H[sub 5])Fe(CO)[sub 2]I] reacts with 1-phenyl-3,4-dimethylphosphole (DMPP), diphenylvinylphosphine (DPVP), and divinylphenylphosphine (DVPP) to produce [([eta][sup 5]-C[sub 5]H[sub 5])Fe(CO)(R[sub 3]P)I], [([eta][sup 5]-C[sub 5]H[sub 5])Fe(CO)(R[sub 3]P)[sub 2

  4. New N-phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATPase inhibitors of DNA gyrase.

    PubMed

    Zidar, Nace; Tomašič, Tihomir; Macut, Helena; Sirc, Anja; Brvar, Matjaž; Montalvão, Sofia; Tammela, Päivi; Ilaš, Janez; Kikelj, Danijel

    2016-07-19

    Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 μM against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds - especially by varying their size, the position and orientation of key functional groups, and their acid-base properties. The structure-activity relationship (SAR) was examined and the results were rationalised with molecular docking. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  5. 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

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

    NASA Astrophysics Data System (ADS)

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

    2014-12-01

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

  7. 11-Methyl-12a-phenyl-9a,12a-dihydrophenanthro[9',10:5,6][1,4]dioxino[2,3-d]thiazole.

    PubMed

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

    2002-09-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2016-12-01

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

  9. 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.

  10. 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 acid...

  11. 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 acid...

  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, 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 acid...

  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, 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 acid...

  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, 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 acid...

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

    Code of Federal Regulations, 2010 CFR

    2010-07-01

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

  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

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

  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

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

  18. 40 CFR 721.1800 - 3,3′,5,5′-Tetra-methyl-bi-phenyl-4,4′-diol.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

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

  19. 2-[4-Acetyl-5-(biphenyl-4-yl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]phenyl acetate

    PubMed Central

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

    2010-01-01

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

  20. Novel Microtubule-Interacting Phenoxy Pyridine and Phenyl Sulfanyl Pyridine Analogues for Cancer Therapy

    PubMed Central

    Anchoori, Ravi Kumar; Kortenhorst, Madeleine Susanne Quirine; Hidalgo, Manuel; Sarkar, Taradas; Hallur, Gurulingappa; Bai, Ruoli; Van Diest, Paul J.; Hamel, Ernest; Khan, Saeed R.

    2008-01-01

    Current microtubule inhibitory agents used in the clinic to treat cancer have severe side effects, and development of resistance is frequent. We have evaluated the antitumor effect of a novel 30-compound library of phenoxy pyridine and phenyl sulfanyl pyridine derivatives. MTT assays revealed that, of all 30 compounds tested, compounds 2 and 3 showed the largest decrease in proliferation (low μM range) against Panc1 and HS766T human pancreatic cancer cells. Flow cytometry experiments with MCF7 breast cancer cells showed a G2/M arrest comparable to that of colcemid. Immunofluorescence staining demonstrated complete disappearance of intracellular microtubules. Tubulin assembly assays, however, showed a dose-dependent decrease in tubulin assembly with compound 3 that seemed limited to about 50% of the control reaction. With compound 2 treatment, there was only a delay in the onset of assembly, with no effect on the extent of the reaction. Taken together, our results show that these novel microtubule inhibitors have promising anticancer activity and can be potentially used to overcome paclitaxel resistance in the clinical setting. PMID:18778046

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

    PubMed

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

    1996-01-01

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

  2. 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. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

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

    PubMed Central

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

    2010-01-01

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

  4. Electroreduction of Viologen Phenyl Diazonium Salts as a Strategy To Control Viologen Coverage on Electrodes.

    PubMed

    Cao, Liangcheng; Fang, Gan; Wang, Yuechuan

    2017-01-31

    A majority of the reported electrografting of aryldiazonium salts result in the formation of covalently attached films with a limited surface coverage of below 5 nmol·cm(-2). Herein, we report the preparation of higher-thickness redox-active viologen-grafted electrodes from the electroreduction of viologen phenyl diazonium salts, by either cyclic voltammetric (CV) sweeps or electrolysis using a fixed potential. Both of the methodologies were successfully applied for various conductive surfaces, including glassy carbon (GC), gold disc, indium tin oxide glass, mesoporous TiO2 electrodes, and 3D compacted carbon fibers. A robust maximal viologen coverage, Γviologen = 9.5 nmol·cm(-2), was achieved on a GC electrode by CV electroreduction. Electroreduction held at a fixed potential at Eappl. = -0.3 V can fabricate viologen-grafted electrodes with Γviologen in the range of 0-37 nmol·cm(-2) in a controllable way, by simply adjusting the electrodeposition time tappl.. Time-dependent Γviologen were found to be 10 nmol·cm(-2)@2 min, 20 nmol·cm(-2)@4.2 min, and 30 nmol·cm(-2)@7 min. Furthermore, a TiO2 electrode coupled with Γviologen of 140 nmol·cm(-2) exhibited electrochromic performance, with the color changing from pale yellow to blue and red brown.

  5. In vitro photosensitization initiated by camphorquinone and phenyl propanedione in dental polymeric materials.

    PubMed

    Christensen, Terje; Morisbak, Else; Tønnesen, Hanne Hjorth; Bruzell, Ellen M

    2010-09-02

    Documentation is scarce on the photobiological effects of photoinitiators present in dental light curable materials. The aim of this study was to determine cellular effects of the photoinitiators camphorquinone (CQ) and phenyl propanedione (PPD) and to investigate whether these substances produced reactive oxygen species after low and high doses of optical radiation (between 0 and 17J/cm(2)). Rat salivary gland cells in vitro were exposed to visible blue light and/or UVA. Hematoporphyrin (HP), a photosensitizer used in medicine, and the UVA-filter 2-methoxy-4-hydroxy-benzophenone (B-3) were used as reference substances. It was found that PPD produced hydrogen peroxide, but not singlet oxygen, upon light irradiation. CQ produced neither hydrogen peroxide nor singlet oxygen. Cell death by necrosis and apoptosis was induced by irradiation in the presence of CQ, PPD and HP. Doses higher than 6J/cm(2) UVA and blue visible light from a source similar to clinically applied sources, induced apoptosis even in the absence of photosensitizers added. A reciprocity relationship was found between radiant exposure (at constant irradiance) and concentration of photoinitiators. In conclusion, the oral cells under investigation were light sensitive, and the sensitivity increased in presence of photoinitiators. PPD acted by mechanisms that included reactive oxygen species and CQ probably by formation of free radicals. Copyright (c) 2010 Elsevier B.V. All rights reserved.

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

    PubMed

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

    2009-09-01

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

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

    PubMed Central

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

    2009-01-01

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

  8. 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.

  9. Efficient kinetic resolution of phenyl glycidyl ether by a novel epoxide hydrolase from Tsukamurella paurometabola.

    PubMed

    Wu, Kai; Wang, Hualei; Sun, Huihui; Wei, Dongzhi

    2015-11-01

    Enantioselective hydrolysis of racemic epoxides mediated by epoxide hydrolases (EHs) is one of the most promising approaches to obtain enantiopure epoxides. In this study, we identified and characterized a novel EH (TpEH1) from Tsukamurella paurometabola by analyzing the conserved catalytic residues of EH. TpEH1 was overexpressed and purified, and its catalytic properties were studied using racemic phenyl glycidyl ether (PGE) and its derivatives as substrates. TpEH1 showed excellent enantioselectivity to the substrates PGE, 3-methylPGE, and 3-nitroPGE. The highest enantioselectivity (E > 100) was achieved when 3-nitroPGE was used as the substrate. The recombinant Escherichia coli TpEH1 demonstrated high substrate tolerance toward PGE and could hydrolyze PGE at concentrations of up to 400 mM (60 g/L) with high enantioselectivity (E = 65), giving (R)-PGE with enantiomeric excess of more than 99 % ee and 45 % yield within 1 h. This concentration of PGE is the highest reported concentration catalyzed by native EHs to date. Thus, the easily available and highly active E. coli TpEH1 showed great potential for the practical preparation of optically pure (R)-PGE.

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

    PubMed

    Ogawa, Kakuyou; Ito, Michiho

    2016-01-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2013-03-01

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

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

    PubMed

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

    2017-01-27

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

  13. 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.

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

    NASA Astrophysics Data System (ADS)

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

    2016-03-01

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

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

    PubMed

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

    2007-05-01

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

  16. 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.

  17. 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).

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

    PubMed

    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. © 2013 Published by Elsevier Inc.

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

    PubMed

    Glaser, Rainer; Knotts, Nathan

    2006-02-02

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

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

    PubMed

    Muller, Alfred; Davis, Wade L

    2012-12-01

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

  1. 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.

  2. Magneto-optical spectroscopic studies of solid and solution-phase tetra-phenyl porphyrin

    NASA Astrophysics Data System (ADS)

    Wahlen-Strothman, Jacob; Pan, Zhen Wen; Manning, Lane; Furis, Madalina; Chu, Kelvin

    2011-03-01

    Tetraphenylporphyrin (TPP) is a synthetic heterocyclic compound that serves as a model system for heme proteins and cytochromes. TPP can accomodate a metal ion in the center; D-shell ion porphyrin complexes with a crystalline solid phase are of interest for magnetic studies because of the possibility of macroscopic long range magnetic order of the ion spins. We have investigated the 5K magnetic properties of poly-crystalline thin films of the heme protoporphyrin IX analogue tetra-phenyl porphyrin, complexed with Zn and Mn, deposited through a capillary pen technique that produces 100um to 1 mm sized grains. Our novel experimental setup measures the UV/VIS, linear dichroism and magnetic circular dichorism simultaneously, incorporates a photoelastic modulator and a microscopy superconducting magnet for high-field (5T) measurements. We present solution and crystalline data on metal-complexed TPP; data are analyzed in terms of A and B-type MCD using a perimeter model. We find good agreement with previous solution data, and novel crystalline phase spectra that are correlated to the long range ordering. This work supported by NSF DMR-0821268, DUE-0942562 and EPS-0701410.

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

    NASA Astrophysics Data System (ADS)

    Badawi, Hassan M.; Förner, Wolfgang

    2011-09-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2012-08-01

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

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

    PubMed

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

    2012-12-07

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

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

    PubMed

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

    1978-01-01

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

  7. Structures, Metal Ion Affinities, and Fluorescence Properties of Soluble Derivatives of Tris((6-phenyl-2-pyridyl)methyl)amine

    PubMed Central

    Liang, Jian; Zhang, Jing; Zhu, Lei; Duarandin, Alexander; Young, Victor G.; Geacintov*, Nicholas; Canary, James W.

    2009-01-01

    Metal complexes of tris((6-phenyl-2-pyridyl)methyl)amine (2) have hydrophobic cavities that potentially accommodate small molecules. However, the utility of this attractive motif has been hampered by the poor solubility of such complexes in many common solvents. In this study, two tripodal ligands (3, tris-[6-(3,4,5-trimethoxy-phenyl)-pyridin-2-ylmethyl]-amine, and 4, tris((6-(3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)pyridin-2-yl)methyl)amine) derived from 2 were prepared with enhanced solubility in organic and aqueous solvents. The X-ray crystallographic analyses of selected ligands and complexes revealed that the hydrophobic cavities inside the zinc complexes were retained after derivatization. Fluorescence, NMR, and potentiometric titration studies, which were enabled by the improved solubility, were performed to investigate the binding properties of the soluble ligands (3, 4) with metal ions such as Zn2+ and Cu2+. When saturating quantities of Zn2+ ions are added to ligand 3 in acetonitrile, the fluorescence emission maximum exhibits a pronounced red shift of ~ 80 nm (from 376 to 457 nm) and is enhanced by a factor of > 100 when measured at 520 nm. The fluorescence properties of the Zn2+ ion-coordinated ligands in the Zn(3) complex are consistent with a charge-transfer character in the excited state, with possible contributions from a planarization of the pyridyl-trimethoxyphenyl groups in the excited state, and from excitonic interactions. PMID:19877674

  8. 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.

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

    PubMed

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

    2015-04-01

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

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

    PubMed

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

    2014-12-08

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

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

    PubMed

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

    2015-01-01

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

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

    PubMed

    Bulut, Gülen; Oktav, Mehmet; Ulgen, Mert

    2004-01-01

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

  13. Binding of the Amphetamine-like 1-Phenyl-piperazine to Monoamine Transporters

    PubMed Central

    2012-01-01

    The human serotonin transporter (hSERT), the human dopamine transporter (hDAT), and the human norepinephrine transporter (hNET) facilitate the active uptake of the neurotransmitters serotonin, dopamine, and norepinephrine from the synaptic cleft. Drugs of abuse such as MDMA (streetname “ecstasy”) and certain 1-phenyl-piperazine (PP) analogs such as 1-(3-chlorophenyl)-piperazine (mCPP) elicit their stimulatory effect by elevating the synaptic concentration of serotonin by blocking or reversing the normal transport activity of hSERT. Recent data suggest that certain analogs of PP may be able to counteract the addictive effect of cocaine. Little is still known about the precise mechanism by which MDMA and PP analogs function at hSERT, hDAT, and hNET and even less is known about the specific protein–ligand interactions. In this study, we provide a comprehensive biochemical examination of a repertoire of PP analogs in hSERT, hDAT, and hNET. Combined with induced fit docking models and molecular dynamics simulations of PP and 1-(3-hydroxyphenyl)-piperazine (3-OH-PP) bound to hSERT and hDAT, we present detailed molecular insight into the promiscuous binding of PP analogs in the monoamine transporters. We find that PP analogs inhibit uptake as well as induce release in all three monoamine transporters. We also find that the selectivity of the PP analogs can be adjusted by carefully selecting substituents on the PP skeleton. PMID:23019496

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

    NASA Astrophysics Data System (ADS)

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

    2011-12-01

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

  15. Validation and scale-up of plasmid DNA purification by phenyl-boronic acid chromatography.

    PubMed

    Gomes, A Gabriela; Azevedo, Ana M; Aires-Barros, M Raquel; Prazeres, D Miguel F

    2012-11-01

    This study addresses the feasibility of scaling-up the removal of host cell impurities from plasmid DNA (pDNA)-containing Escherichia coli lysates by phenyl-boronic (PB) acid chromatography using columns packed with 7.6 and 15.2 cm(3) of controlled porous glass beads (CPG) derivatized with PB ligands. Equilibration was performed with water at 10 cm(3) /min and no conditioning of the lysate feed was required. At a ratio of lysate feed to adsorbent volume of 1.3, 93-96% of pDNA was recovered in the flow through while 66-71% of impurities remained bound (~2.5-fold purification). The entire sequence of loading, washing, elution, and re-equilibration was completed in 20 min. Run-to-run consistency was observed in terms of chromatogram features and performance (yield, purification factor, agarose electrophoresis) across the different amounts of adsorbent (0.75-15.2 cm(3) ) by performing successive injections of lysates prepared independently and containing 3.7 or 6.1 kbp plasmids. The column productivity at large scale was 4 dm(3) of alkaline lysate per hour per dm(3) of PB-CPG resin. The method is rapid, reproducible, simple, and straightforward to scale-up. Furthermore, it is capable of handling heavily contaminated samples, constituting a good alternative to purification techniques such as isopropanol precipitation, aqueous two-phase systems, and tangential flow filtration. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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

    PubMed

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

    2003-01-01

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

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

    SciTech Connect

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

    2009-01-01

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

  18. alpha-Phenyl-tert-butyl-nitrone inhibits free radical release in brain concussion.

    PubMed

    Sen, S; Goldman, H; Morehead, M; Murphy, S; Phillis, J W

    1994-06-01

    Traumatic brain injury (TBI) is one of the important causes of mortality and morbidity. The pathogenesis of the underlying brain dysfunction is poorly understood. Recent data have suggested that oxygen free radicals play a key role in the primary and secondary processes of acute TBI. We report direct electron spin resonance (ESR) evidence of hydroxyl (.OH) radical generation in closed-head injury of rats. Moderate brain concussion was produced by controlled and reproducible mechanical, fixed, closed-head injury. A cortical cup was placed over one cerebral hemisphere within 20 min of the concussion, perfused with artificial cerebrospinal fluid (aCSF) containing the spin trap agent pyridyl-N-oxide-tert-butyl nitrone (POBN, 100 mM), and superfusate samples collected at 10 min intervals for a duration up to 130 min post brain trauma. In addition, POBN was administered systemically (50 mg/kg body wt.) 10 min pretrauma and 20 min posttrauma to improve our ability to detect free radicals. ESR analysis of the superfusate samples revealed six line spectra (alpha N = 15.4 G and alpha beta H = 2.5 G) characteristic of POBN-OH radical adducts, the intensity of which peaked 40 min posttrauma. The signal was undetectable after 120 min. Administration of alpha-phenyl-tert-butyl-nitrone (PBN), a spin adduct forming agent systemically (100 mg/kg body wt. IP 10 min prior to concussion) alone or along with topical PBN (100 mM PBN in aCSF), significantly (p < 0.001) attenuated the ESR signal, suggesting its possible role in the treatment of TBI.

  19. 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.

  20. 2-Phenyl-APB-144-Induced Retinal Pigment Epithelium Degeneration and Its Underlying Mechanisms

    PubMed Central

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

    2015-01-01

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

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

    PubMed

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

    2001-07-15

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

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

    PubMed

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

    2016-04-15

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

  3. Tuning the electronic nature of mono-bay alkynyl-phenyl-substituted perylene bisimides: synthesis, structure, and photophysical properties.

    PubMed

    Mishra, Ruchika; Lim, Jong Min; Son, Minjung; Panini, Piyush; Kim, Dongho; Sankar, Jeyaraman

    2014-05-05

    Perylene bisimide (PBI) derivatives with various alkynyl-phenyl substituents at a single bay position have been synthesised by Sonogashira coupling. NMR spectroscopic studies reveal the unsymmetric nature of the dyads. All of the dyads undergo two reversible reductions, which demonstrates their structural and electrochemical rigidity. The synthesised dyads show a remarkable redshift in their absorption maxima and sharp vibronic progression. Electron-rich substituents facilitate efficient charge transfer from the substituent HOMO to the electron-deficient PBI core. The most interesting spectral signatures were exhibited by a PBI with a strongly electron-donating ethynyl(dimethylaminophenyl) substituent. The steady-state features of this PBI showed a broad absorption that covered almost the whole visible region with no emission. A twisted intramolecular charge-transfer (TICT) process, related to the rotational motion of ethynyl(dimethylaminophenyl) PBI, was also demonstrated. Computational investigations shed light on the coplanarity of the various substituents with respect to the PBI core; the PBI core itself remains flat without any noticeable deformation even after mono-functionalisation. This illustrates that mono-functionalisation exerts meagre steric hindrance on the bay positions relative to disubstituted analogues. Despite several previous reports on the structural characterisation of 1,7-disubstituted PBI derivatives, we present the first structural characterisation of a mono-bay ethynyl-phenyl substituted PBI. The solid-state structure of the phenyl derivative has a flat PBI core without any noticeable steric constraints from the substituents, as predicted. In contrast, single-crystal X-ray analysis for the mono-bromo bay-substituted PBI shows that the bromine substituent is not in the plane of the PBI core. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  4. Synthesis and evaluation of fluorine-substituted phenyl acetate derivatives as ultra-short recovery sedative/hypnotic agents.

    PubMed

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

    2014-01-01

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

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

    PubMed Central

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

    2014-01-01

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

  6. 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

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

    PubMed

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

    2017-01-12

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

  8. 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.

  9. [The characteristic infrared spectra of N-(2-phenyl-(1,2,3-triazole-formyl)-N'-arylthioueas].

    PubMed

    An, Y; Li, Y; Hu, J; Meng, L; Wang, G

    2001-04-01

    The characteristic infrared spectra of N-(2-phenyl-(1,2,3-triazole-formyl)-N'-aryl)-thioueas have been studied and the changing rules with the change of chemical structure have been discussed. Specially, the effect of the characteristic infrared of long-range radical by different substitute is discussed in detail. Results show that characteristic bands of radical which as far as five radicals away form substitute group are still affected. It is very suggestive meaning for long-range spectra research.

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

    PubMed

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

    2014-04-22

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

  11. 7-Phenyl-sulfonyl-2,3-dihydro-7H-1,4-benzodioxino[6,7-b]carbazole.

    PubMed

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

    2010-11-20

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

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

    PubMed

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

    2012-09-15

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

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

    NASA Astrophysics Data System (ADS)

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

    1995-08-01

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

  14. Discovery of substituted (4-phenyl-1H-imidazol-2-yl)methanamine as potent somatostatin receptor 3 agonists.

    PubMed

    Lai, Zhong; He, Shuwen; Sherer, Edward C; Wu, Zhicai; Yu, Yang; Ball, Richard; Hong, Qingmei; Yang, David X; Guo, Liangqing; Li, Derun; Tuang, Quang; Chicchi, Gary G; Trusca, Dorina; Tsao, Kwei-Lan; Zhou, Yun-Ping; Howard, Andrew D; Nargund, Ravi P; Hagmann, William K

    2015-09-01

    We report SAR studies on a novel non-peptidic somatostatin receptor 3 (SSTR3) agonist lead series derived from (4-phenyl-1H-imidazol-2-yl)methanamine. This effort led to the discovery of a highly potent low molecular weight SSTR3 agonist 5c (EC50=5.2 nM, MW=359). The results from molecular overlays of 5c onto the L-129 structure indicate good alignment, and two main differences of the proposed overlays of the antagonist MK-4256 onto the conformation of 5c lead to inversion of antagonism to agonism. Copyright © 2015 Elsevier Ltd. All rights reserved.

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

    SciTech Connect

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

    1983-01-01

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

  16. 4-Hy­droxy-1-methyl-3-phenyl­quinolin-2(1H)-one

    PubMed Central

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

    2013-01-01

    In the title compound, C16H13NO2, 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 mol­ecules into infinite chains running along the b-axis direction. PMID:23424511

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

    PubMed

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

    2012-08-01

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

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

    PubMed

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

    2011-05-20

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

  19. Effects of deuteration of the methyl and phenyl hydrogens on the rotational spectrum of anisole-water

    NASA Astrophysics Data System (ADS)

    Giuliano, Barbara M.; Melandri, Sonia; Caminati, Walther

    2017-07-01

    The role of non-covalent interactions in determining the structure of the 1:1 anisole-water molecular complex has been investigated by the analysis of the rotational spectra of the complex formed by the C6H5OCD3 and C6D5OCH3 deuterated species of anisole recorded with pulsed jet Fourier transform microwave spectroscopy. The deuteration of the methyl and phenyl hydrogens does not affect the structure and the internal dynamics of the complex, differently from the deuteration of the water moiety, which leads to large isotopic effects (Giuliano et al., 2005).

  20. Electronic properties of electron-doped [6,6]-phenyl-C61-butyric acid methyl ester and silylmethylfullerene

    NASA Astrophysics Data System (ADS)

    Furutani, Sho; Okada, Susumu

    2017-06-01

    Electronic properties of electron-doped chemically decorated C60 fullerenes, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) and silylmethylfullerene (SIMEF), by a planar electrode were studied using density functional theory combined with the effective screening medium method to simulate the heterointerface between the chemically decorated C60 and cationic counter materials. We find that the distribution of accumulated electrons and induced electric field depend on the molecular arrangement with respect to the external electric field of the electrode. We also show that the quantum capacitance of the molecule is sensitive to molecular arrangement owing to the asymmetric distribution of the accumulated electrons.

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

    PubMed

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

    2004-05-13

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

  2. Crystal structure of 4-(2-bromo­prop­ion­yl)-3-phenyl­sydnone

    PubMed Central

    Grossie, D.; Harrison, L.; Turnbull, K.

    2014-01-01

    Sydnones are a class of mesoionic compounds containing a five-membered heterocyclic ring. In general, sydnone com­pounds are synthesized with an aromatic substutuent at the N3 position. This feature, adds to the stability of the heterocyclic ring. In the title compound {systematic name: 4-(2-bromo­propano­yl)-3-phenyl-1,2,3λ5-oxa­diazol-3-ylium-5-olate}, C11H9BrN2O3, the aromatic substitutent is an unsubstituted phenyl ring. The sydnone ring is almost planar, with a maximum deviation from the mean plane of 0.023 (1) Å, but is not coplanar with the phenyl ring, having a dihedral angle of 40.93 (8)°. The carbonyl side chain is twisted relative to the syndone ring by 15.8 (2)°. The mol­ecules are packed in the unit cell as pairs related by an inversion center at (1, 0, 1/2). The pairs inter­act via π-stacking, with the distance separating the centroids being 3.824 (1) Å. The Br atom has two contacts, one to an N atom in a neighboring asymmetric unit with a distance of 3.346 (2) Å (the sum of the van der Waals radii is 3.40 Å) and a second to an H atom with a distance of 3.03 Å. The contact with the H atom is perpendicular (C—Br⋯H = 98.60°) to the C—Br bond, and that to the N atom is linear [C—Br⋯N = 169.10 (5)°] to the C—Br bond. The O atom of the sydnone ring is involved in two hydrogen bonds, one intra­molecular with a donor–acceptor distance of 3.1486 (19) Å and a second that is inter­molecular, with a phenyl H atom as the donor and has a donor–acceptor distance of 3.346 (2) Å. PMID:25484806

  3. Oxidative Activation of C-S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides.

    PubMed

    Kitowski, Annabel; Jiménez-Moreno, Ester; Salvadó, Míriam; Mestre, Jordi; Castillón, Sergio; Jiménez-Osés, Gonzalo; Boutureira, Omar; Bernardes, Gonçalo J L

    2017-10-06

    A method for the selective activation of thioglycosides that uses the N(+)-thiophilic reagent O-mesitylenesulfonylhydroxylamine (MSH) as a promoter is presented. The reaction proceeds via anomeric mesitylensulfonate intermediates, which could be isolated and fully characterized by placing a fluorine atom at the C2 position. In the presence of a soft Lewis acid, glycosylation reaction proceeds at ambient temperature with good yields. It is further demonstrated that it is possible to orthogonally activate S-ethyl in the presence of S-phenyl donors, enabling the design of sequential glycosylation strategies.

  4. 1-[4-Chloro-3-(trifluoro-meth-yl)phen-yl]-4-phenyl-1H-1,2,3-triazole.

    PubMed

    Altimari, Jarrad M; Healy, Peter C; Henderson, Luke C

    2012-11-01

    In the title compound, C(15)H(9)ClF(3)N(3), the phenyl and chloro-trifluoro-methyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the crystal, the mol-ecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å.

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

    PubMed Central

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

    2016-01-01

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

  6. 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.

  7. 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

  8. Synthesis and anticonvulsant and neurotoxic properties of substituted N-phenyl derivatives of the phthalimide pharmacophore.

    PubMed

    Vamecq, J; Bac, P; Herrenknecht, C; Maurois, P; Delcourt, P; Stables, J P

    2000-04-06

    A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal (ip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 microM, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 microM excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.

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

    NASA Astrophysics Data System (ADS)

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

    2013-06-01

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

  10. 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.

  11. Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione

    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.

  12. Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione.

    PubMed

    Sahani, M K; Yadava, U; Pandey, O P; Sengupta, S K

    2014-05-05

    A new class of oxovanadium(IV) complexes with Schiff bases derived by the condensation of 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazoles and indoline-2,3-dione have been prepared in ethanol in the presence of sodium acetate. Micro-analytical data, magnetic susceptibility, UV-Vis, IR, EPR and XRD spectral techniques were used to confirm the structures. Electronic absorption spectra of the complexes suggest a square-pyramidal geometry. The oxovanadium(IV) complexes have monoclinic crystal system and particle sizes were found to be in the range 18.0 nm to 24.0 nm (nano-size). In vitro antifungal activity of synthesized compounds was determined against fungi Aspergillus niger, Colletotrichum falcatum and Colletotrichum pallescence and in vitro antibacterial activity was determined by screening the compounds against Gram-negative (Escherichia coli and Salmonella typhi) and Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacterial strains. The oxovanadium(IV) complexes have higher antimicrobial effect than free ligands.

  13. Preclinical pharmacokinetic characterization of 2-(4-(4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl) acetic acid, a novel DGAT-1 inhibitor.

    PubMed

    Kwak, Eun-Young; Im, So Hee; Seo, Hyewon; Cho, Woon-Ki; Lee, Ye-Lim; Woo, Jaechun; Ahn, Sunjoo; Ahn, Sung-Hoon; Kwak, Hyun Jung; Ahn, Jin Hee; Bae, Myung Ae; Song, Jin Sook

    2014-05-01

    1. A novel diacylglyceride acyltransferase-1 (DGAT-1) inhibitor, 2-(4-(4-(5-(2-phenyl-5-(trifluoromethyl) oxazole-4-carboxamido)-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl) acetic acid (KR-69232), was synthesized for a potential therapeutic use against several metabolic disorders, such as obesity, insulin resistance, and type II diabetes, characterized by excessive triglycerides (TGs) in the blood. 2. The half-lives against phase I metabolism were measured as 75.3 ± 20.9 min and over 120 min in rat and human liver microsomes, respectively. In Caco-2 cell monolayers, extremely low permeability (<0.13 × 10⁻⁶cm/s) was seen in the absorptive direction, predicting limited intestinal absorption of KR-69232. This compound was highly bound to rat and human plasma proteins (>99.8%). 3. With the intravenous administration of KR-69232 in rats (1, 2, and 5 mg/kg), non-linear kinetics were observed at the highest dose, with significantly higher systemic clearance, higher volume of distribution, and lower dose-normalized AUC. Following oral administration, it exhibited low bioavailability (<10%) and was absorbed slowly (T(max), 3.8-5.2 h) over the dose range. We also confirmed that considerable KR-69232 remained in the intestine at T(max), demonstrating its limited absorption into the systemic circulation.

  14. Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea.

    PubMed

    Kashaw, Sushil K; Kashaw, Varsha; Mishra, Pradeep; Jain, N K; Stables, J P

    2009-11-01

    Several new 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea were synthesized and screened for anticonvulsant, CNS depressant and sedative-hypnotic activity in the mice. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight synthesized compounds were examined in the maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data and elemental analysis were consistent with the newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. Compounds E1, E6, E9, E12, P3, P4 and P6 were found to be active in the MES screen whereas E1, P4, P6 and P11 were found to be active in the scPTZ screen. All except E6, E11 and P6 showed more than 50% decrease in locomotor activity at 1h of compound administration via actophotometer screen. CNS depressant activity screened with the help of the forced swim method resulted into some potent compounds. All the compounds were found to exhibit potent CNS depressants activity as indicated by increased immobility time. It can be concluded that newly synthesized compounds possessed promising CNS activities.

  15. 3-(1,3-Di­phenyl­propan-2-yl)-4-methyl-6-phenyl­isoxazolo[3,4-d]pyridazin-7(6H)-one

    PubMed Central

    Campana, Charles F.; Mirzaei, Joseph; Koerner, Chris; Gates, Christina; Natale, Nicholas R.

    2013-01-01

    In the title compound, C27H23N3O2, the geminal benzyl groups branching out from the methine adjacent to the isoxazole group are both syn-oriented to the methyl group of the pyridazinone moiety, as reflected by C—C distances of 3.812 (2) and 4.369 (2) Å between the methyl carbon and the nearest ring carbon of each benzyl group. This kind of conformation is retained in CDCl3 solution, as evidenced by distinct phenyl-shielding effects on the 1H NMR signals of the methyl H atoms. The isoxazolo[3,4-d]pyridazin ring system is virtually planar (r.m.s. deviation from planarity = 0.031 Å), but the N-bonded phenyl group is inclined to the former by an ring–ring angle of 55.05 (3)°. In the crystal, the T-shaped mol­ecules are arranged in an inter­locked fashion, forming rod-like assemblies along [10-1]. The mol­ecules are held together by unremarkable weak C—H⋯N, C—H⋯O and C—H⋯π inter­actions (C—O,N,C > 3.4 A), while significant π–π-stacking inter­actions are absent. PMID:24454112

  16. 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.

  17. 3-(Phenyl-4-oxy)-5-phenyl-4,5-dihydro-(1H)-pyrazole: A fascinating molecular framework to study the enantioseparation ability of the amylose (3,5-dimethylphenylcarbamate) chiral stationary phase. Part II. Solvophobic effects in enantiorecognition process.

    PubMed

    Pierini, Marco; Carradori, Simone; Menta, Sergio; Secci, Daniela; Cirilli, Roberto

    2017-05-26

    The enantiomers of five chiral compounds incorporating the 3-(phenyl-4-oxy)-5-phenyl-4,5-dihydro-(1H)-pyrazole scaffold and differing only in the linear alkyl chain (varying in length from 1 to 5 carbon atoms) linked to the oxygen atom were directly separated on the amylose (3,5-dimethylphenylcarbamate) based Chiralpak AD-3 chiral stationary phase. The effects of the mobile phase composition, the structure of the analytes and temperature on the retention and enantioselectivity were investigated. It was found that the enantiomeric separations were in all cases enthalpy-driven and disfavored by entropic term. U-shape curves obtained by plotting the chromatographic data versus the alcoholic percentage in n-pentane-methanol and n-hexane-ethanol mobile phases highlighted that, at higher alcohol concentrations, solvophobic interactions were operative in the retention mechanism. The unusual trend of such curves was linked to the nature of alkyl chain of the pyrazolines and it was indicative of the solvophobic contribution to the achievement of a high degree of enantioseparation. Copyright © 2017 Elsevier B.V. All rights reserved.

  18. 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.

  19. 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.

  20. The role of polymer dots on efficiency enhancement of organic solar cells: Improving charge transport property

    NASA Astrophysics Data System (ADS)

    Li, Jinfeng; Zhang, Xinyuan; Liu, Chunyu; Li, Zhiqi; He, Yeyuan; Zhang, Zhihui; Shen, Liang; Guo, Wenbin; Ruan, Shengping

    2017-07-01

    In this work, poly(9,9-dioctylfluorene)-co-(4,7-di-2-thienyl-2,1,3-benzothiadiazole) (PF-5DTBT) and copolymer poly(styrene-co-maleic anhydride) (PSMA) dots were prepared as additive for active layer doping to enhance the power conversion efficiency (PCE) of organic solar cells (OSCs), which based on poly[N-9″-hepta-decanyl-2,7-carbazole-alt-5,5-(4‧,7‧-di-2-thienyl-2‧,1‧,3‧-benzothiadiazole) (PCDTBT) and [6,6]-phenyl C71 butyric acid methyl-ester (PC71BM). A high efficiency of 7.40% was achieved due to increase of short-circuit current (Jsc) and fill factor (FF). The operation mechanism of OSCs doping with polymer dots was investigated, which demonstrated that the efficiency enhancement ascribes to improvement of electrical properties, such as exciton generation, exction dissociation, charge transport, and charge collection.

  1. 1-Ethyl-2-phenyl-3-[2-(tri­methyl­sil­yl)ethyn­yl]-1H-indole

    PubMed Central

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

    2013-01-01

    The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with tri­methyl­silyl­acetyl­ene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C—H⋯π inter­actions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the tri­methyl­silyl unit are equally disordered over two sets of sites. PMID:23795091

  2. Novel Synthesis of Highly Phenyl-Substituted Spirobifluorene and Carbazole Derivatives Through Diels-Alder Reaction for Light-Emitting Diodes

    NASA Astrophysics Data System (ADS)

    Lee, Seung Eun; Cho, Hyun Nam; Jung, Sung Hyun; Park, Ho Cheol; Lee, Chang June; Park, Jong Wook

    We synthesized and characterized novel highly phenyl-substituted spirobifluorene and carbazole derivatives such as 3,6-bis[(2,3,4,5-tetraphenyl)phenyl]-9-ethylcarbazole (BTPEC); 3,6-bis(7,10-diphenyl-fluoranthene)-9-ethylcarbazole (BDFEC); 2,7-Bis[(2,3,4,5-tetraphenyl)phenyl]-9,9‧-spirobifluorene (BTPSF); and 3,6-bis(7,10-diphenyl-fluo-ran-thene)-9,9‧-spirobifluorene (BDFSF), through Diels-Alder reaction. BDFEC showed sky blue PL spectrum at 481 nm and BTPSF showed ultra-violet PL spectrum at 374 nm in chloroform solution. Also BTPEC and BDFSF exhibited PL spectrum at around the UV region, 390 and 467 nm.

  3. Separation Differences Among Phenyl Hydride, UDC Cholesterol and Bidentate C8 Stationary Phases for Stability Indicating Methods of Tetracyclines: Journal of Liquid Chromatography & Related Technologies.

    PubMed

    Young, Joshua E; Matyska, Maria T; Azad, Anil K; Yoc, Sergio E; Pesek, Joseph J

    2013-04-01

    Formulation extracts of tetracycline hydrochloride (HCl), minocycline hydrochloride (HCl), and doxycycline hyclate were degraded by strong acidic conditions and heating. Subsequently, components of the extracts were separated by Bidentate C8, Phenyl Hydride and Cholesterol (UDC) HPLC columns operating in the reverse phase mode. The Phenyl Hydride column was able to baseline separate minocycline from the observed degradant, while partial or total co-elution was observed with the other two columns using otherwise identical method conditions. For both the degraded tetracycline HCl and doxycycline hyclate extracts, the UDC column gave the best resolution for the critical pair. The findings suggest that the postulated secondary retention mechanisms of π-π interactions from the Phenyl Hydride and shape selectivity from the UDC can provide superior resolution for structurally similar analytes compared to hydrophobic interactions alone.

  4. 3-Bromo-methyl-4-meth-oxy-2-(2-nitro-phen-yl)-9-phenyl-sulfonyl-9H-carbazole.

    PubMed

    Gopinath, S; Sethusankar, K; Saravanan, Velu; Mohanakrishnan, Arasambattu K

    2014-06-01

    In the title compound, C26H19BrN2O5S, the carbazole tricycle is essentially planar, with the largest deviation being 0.126 (3) Å for the C atom connected to the nitro-phenyl group. The carbazole moiety is almost orthogonal to the benzene rings of the adjacent phenyl-sulfonyl and nitro-phenyl groups, making dihedral angles of 85.43 (15) and 88.62 (12)°, respectively. The mol-ecular conformation is stabilized by two C-H⋯O hydrogen bonds involving the sulfone group, which form similar six-membered rings. In the crystal, mol-ecules symmetrically related by a glide plane are linked in C(6) chains parallel to [001] by C-H⋯O hydrogen bonds formed with the participation of the nitro group. The chains are reinforced by additional C-H⋯π inter-actions.

  5. 1,4-Dimethyl-3-phenyl-3H-pyrazolo[3,4-c]isoquinolin-5(4H)-one.

    PubMed

    Meneghetti, Fiorella; Bombieri, Gabriella; Maggio, Benedetta; Daidone, Giuseppe

    2008-04-16

    The title compound, C(18)H(15)N(3)O, is the product of the thermal decomposition of the diazo-nium salt derived from 2-amino-N-methyl-N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)benzamide. It is characterized by a trans orientation of the methyl groups with respect to the tricyclic ring system. The mol-ecule has a nearly planar phenyl-pyrazolo[3,4-c]isoquinolin-5-one system, the largest deviation from the mean plane being 0.066 (2) Å for the O atom. The dihedral angle between the phenyl substituent and the heterotricycle is 67 (1)°. The packing is stabilized by C-H⋯N hydrogen-bond inter-actions, with the formation of mol-ecular chains along the c axis.

  6. (η6-Benzophenone)(η5-penta­methyl­cyclo­penta­dien­yl)ruthenium(II) tetra­phenyl­borate

    PubMed Central

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

    2009-01-01

    The structure of the title compound, [Ru(C10H15)(C13H10O)](C24H20B), consists of discrete [Cp*Ru(II)benzophenone] cations and tetra­phenyl­borate anions (Cp* = penta­methyl­cyclo­penta­dien­yl). Tethering the Cp*Ru group to one aryl ring of benzophenone results in average values of 1.42 (1) and 1.38 (1) Å for the C—C bond lengths in the Ru-tethered and untethered phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings of the benzophenone group is 50.5 (1)°. PMID:21578208

  7. 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

  8. Phenyl aldehyde and propanoids exert multiple sites of action towards cell membrane and cell wall targeting ergosterol in Candida albicans

    PubMed Central

    2013-01-01

    In the present study, two phyto-compounds phenyl aldehyde (cinnamaldehyde) and propanoid (eugenol) were selected to explore their modes of action against Candida albicans. Electron microscopy, flow cytometry and spectroscopic assays were employed to determine the targets of these compounds. Treatment of C. albicans (CA04) with sub-MICs of cinnamaldehyde (50 μg/mL) and eugenol (200 μg/mL) indicated multiple sites of action including damages to cell walls, cell membranes, cytoplasmic contents and other membranous structures as observed under electron microscopy. Concentration and time dependent increase in the release of cytoplasmic contents accompanied with change in extracellular K+ concentration was recorded. Exposure of Candida cells at 4 × MIC of cinnaamldehyde and eugenol resulted in 40.21% and 50.90% dead cells, respectively as revealed by flow cytometry analysis. Treatment of Candida cells by cinnamaldehyde and eugenol at 0.5 × MIC showed 67.41% and 76.23% reduction in ergosterol biosynthesis, respectively. The binding assays reflected the ability of compounds to bind with the ergosterol. Our findings have suggested that the membrane damaging effects of phenyl aldehyde and propanoids class of compounds is attributed to their ability to inhibit ergosterol biosynthesis and simultaneously binding with ergosterol. Indirect or secondary action of these compounds on cell wall is also expected as revealed by electron microscopic studies. PMID:24010721

  9. Experimental and theoretical study of 2,5-diaryloxazoles whose aryl are para-substituted phenyl groups

    NASA Astrophysics Data System (ADS)

    Ionescu, Sorana; Popovici, Daniela; Balaban, Alexandru T.; Hillebrand, Mihaela

    2005-11-01

    Absorption and emission properties of some phenoxy derivatives of diphenyloxazole (PPO) are presented and discussed. The photophysical properties reflect a dependence on the substituted 2 or 5 position of the oxazole ring. The experimental data were correlated with molecular parameters such as molecular flexibility, electronic structure and the singlet-triplet gap. The substitution with heteroatomic-bridged phenyls maintains the same frontier orbitals ( m, m + 1) as in the parent compound, but introduces a new molecular orbital, m - 1, located on the terminal phenyl. The presence of the so-called band B in the absorption spectra of some diaryloxazoles was attributed to the m - 1 → m + 1 transition participating to the second excited state wave function. The other main component of this state, the m → m + 2 transition, was found to have a forbidden character, explaining the lack or the low intensity of band B. The decrease of the fluorescence quantum yield subsequent to substitution of PPO with phenoxy fragments was found to be due to the enhanced molecular flexibility comparing to PPO. The differences between the 2- or 5-substituted derivatives were rationalized in terms of a smaller S 1-T 2 gap for the former, thus increasing the rate of the overall nonradiative intersystem crossing processes.

  10. Interactions of the neurotoxic amine 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine with monoamine oxidases.

    PubMed

    Singer, T P; Salach, J I; Castagnoli, N; Trevor, A

    1986-05-01

    1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), a thermal breakdown product of a meperidine-like narcotic used by drug abusers as a heroin substitute, produces Parkinsonian symptoms in humans and primates. The nigrostriatal toxicity is not due to MPTP itself but to one or more oxidation products resulting from the action of monoamine oxidase (MAO) on this tertiary allylamine. Both MAO A and B catalyse the oxidation of MPTP to the 1-methyl-4-phenyl-2,3-dihydropyridinium species (MPDP+), which undergoes further oxidation to the fully aromatic 1-methyl-4-phenylpyridinium species (MPP+). These bio-oxidations are blocked by selective inhibitors of MAO A and B. Additionally, MPTP, MPDP+ and MPP+ are competitive inhibitors of MAO A and B. The A form of the enzyme is particularly sensitive to this type of reversible inhibition. Both MAO A and B also are irreversibly inactivated by MPTP and MPDP+, but not by MPP+. This inactivation obeys the characteristics of a mechanism-based or 'suicide' process. The inactivation, which is accompanied by the incorporation of radioactivity from methyl-labelled MPTP, is likely to result from covalent modification of the enzyme.

  11. Phenyl and ionic liquid based bifunctional periodic mesoporous organosilica supported copper: An efficient nanocatalyst for clean production of polyhydroquinolines.

    PubMed

    Elhamifar, Dawood; Ardeshirfard, Hakimeh

    2017-11-01

    A novel phenyl and ionic liquid based bifunctional periodic mesoporous organosilica supported copper (Cu@BPMO-Ph-IL) is prepared, characterized and its catalytic application is developed in the clean production of polyhydroquinolines. The Cu@BPMO-Ph-IL was prepared via chemical grafting of ionic liquid groups onto phenyl-based PMO followed by treatment with copper acetate. This nanocatalyst was characterized with transmission electron microscopy (TEM), scanning electron microscopy (SEM), diffuse reflectance infrared Fourier transform spectroscopy (DRIFTs), thermal gravimetric analysis (TGA), powder X-ray diffraction (PXRD), nitrogen-sorption and energy dispersive X-ray (EDX) analyses. This was successfully applied in the one-pot Hantzsch condensation of aldehydes, ammonium acetate, alkylacetoacetates and dimedone to prepare a set of different derivatives of polyhydroquinolines in high yields and selectivity. The catalyst was effectively recovered and reused several times without important decrease in efficiency. The recovered catalyst was also characterized with TEM analysis to study its stability and durability under applied conditions. Copyright © 2017 Elsevier Inc. All rights reserved.

  12. 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. © 2014 Federation of European Microbiological Societies. Published by John Wiley & Sons Ltd. All rights reserved.

  13. 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.

  14. Discovery of novel N-phenyl 1,4-dihydropyridines with a dual mode of antimycobacterial activity.

    PubMed

    Lentz, Fabian; Hemmer, Marc; Reiling, Norbert; Hilgeroth, Andreas

    2016-12-15

    There is an urgent need for novel drugs for the treatment of tuberculosis (TB) due to the increasing prevalence of antibiotic resistance among Mycobacterium tuberculosis (Mtb) strains against first-line and second-line therapeutics. We developed novel N-phenyl 1,4-dihydropyridines as potential antituberculotic agents. The observed activity depends on the substitution patterns of the aromatic residues. N-unsubstituted 1,4-dihydropyridines are known inhibitors of the cancer-relevant transmembrane efflux pump ABCB1. Based on the similarity of ABCB1 amino acids sequences relevant to 1,4-dihydropyridine binding and the MTb efflux pump Rv0194, we determined ABCB1-inhibitory properties of our compounds in a cell line model. We identified one compound, which substantially increased the activity of two antituberculotic drugs which are substrates of ABCB1. The data indicate that our N-phenyl 1,4-dihydropyridines represent a novel compound class which improves the efficacy of anti-TB drugs by interfering with transmembrane efflux pumps in Mtb. Copyright © 2016 Elsevier Ltd. All rights reserved.

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

    NASA Astrophysics Data System (ADS)

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

    2010-09-01

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

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

    PubMed

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

    2014-10-06

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

  17. SKF-38393, a dopamine receptor agonist, attenuates 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity.

    PubMed

    Muralikrishnan, D; Ebadi, M

    2001-02-23

    Parkinson's disease (PD) is characterized by progressive degeneration of nigrostriatal dopaminergic neurons. Several factors such as inhibition of the mitochondrial respiration, generation of hydroxyl radicals and reduced free radical defense mechanisms causing oxidative stress, have been postulated to contribute to the degeneration of dopaminergic neurons. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) treated animals is a useful experimental model of PD, exhibiting most of the clinical features, as well as the main biochemical and pathologic symptoms of the disease. In the present study, we have examined a dopaminergic (D1) receptor agonist, SKF-38393 HCl (SKF) for its possible neuroprotective action against MPTP-induced insults on dopaminergic neurons. MPTP is converted by monoamine oxidase-B (MAO-B) to its neurotoxic metabolite 1-methyl-4-phenyl-pyridinium (MPP+), which is then taken up into the dopaminergic neurons. SKF-38393 had no effects either on total or monoamine oxidase B in the striatum. SKF-38393 blocked the MPTP-induced depletion of glutathione and attenuated MPTP-induced depletion of dopamine. Furthermore, it enhanced the activity of superoxide dismutase and hence mimicked the action of selegiline. The results of these studies are interpreted to suggest that SKF-38393 may prove a valuable drug in the treatment of Parkinson's disease.

  18. 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

  19. Aminobenzoic acid diuretics. 7. 3-Substituted 4-phenyl-, 4-arylcarbonyl-, and 4-arylmethyl-5-sulfamoylbenzoic acids and related compounds.

    PubMed

    Nielsen, O B; Bruun, H; Bretting, C; Feit, P W

    1975-01-01

    Various 4-substituted 3-alkylamino-, 3-alkoxy-, 3-alkylthio-, and 3-alkyl-5-sulfamoylbenzoic acids related to known aminobenzoic acid diuretics were synthesized and screened for their diuretic properties in dogs. The tabulated results from a 3-hr test period revealed that generally the diuretic profile and potency could be retained when 3-alkoxy, 3-alkylthio, and 3-phenethyl were substituted for the 3-alkylamino moiety. The high potency of several 3-alkoxy-, 3-alkylthio-, and 3-phenethyl-4-benzoyl-5-sulfamoylbenzoic acids confirmed previous suggestions that the apparent diuretic effect of 4- and 5-alkylamino-6-carboxy-3-phenyl-1,2-benzisothiazole 1,1-dioxides originates from the corresponding 4-benzoyl-5-sulfamoylbenzoic acid derivatives due to an existing equilibrium in plasma. 4-Benzoyl-5-sulfamoyl-3-(3-thenyloxy) benzoic acid (118) is among the most potent benzoic acid diuretics hitherto synthesized and shows significant diuretic activity in dogs at 1 mug/kg. The results obtained with different 3-substituted 4-phenyl-5-sulfamoylbenzoic acids supported the earlier concept regarding the steric influence of the 4-substituent on the diuretic potency of sulfamoylbenzoic acid diuretics.

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

    PubMed

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

    2010-09-15

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

  1. Synthesis and COX-2 Inhibitory Activity of 4-[(E)-2-(4-Oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethenyl]benzene-1-sulfonamideand Its Analogs

    PubMed Central

    Hayun; Hudiyono, Sumi; Hanafi, Muhammad; Yanuar, Arry

    2012-01-01

    Some novel 3-phenyl-2-[(E)-2-phenylethenyl]-3,4-dihydroquinazolin-4-one derivatives possessing para-sulfonamides groups on the phenyl ring of the 2-phenylethenyl moiety have been synthesized and their COX-2 inhibitory activity evaluated. The stuctures of the synthesized compounds were confirmed on the basis of FT-IR, 1H-NMR, 13C-NMR and mass spectral data. The COX-2 inhibition screening assay revealed that 4-[(E)-2-{3-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl}ethenyl]benzene-1-sulfonamide had a maximum COX-2 inhibition (47.1%), at a concentration of 20 μM. PMID:24281337

  2. 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as orphanin FQ receptor agonists.

    PubMed

    Wichmann, J; Adam, G; Röver, S; Cesura, A M; Dautzenberg, F M; Jenck, F

    1999-08-16

    A series of 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan+ ++-4-one derivatives 1 was studied with respect to the binding affinity for the orphanin FQ (OFQ) and opioid (mu, kappa, delta) receptors. The influence of stereochemistry as well as the substitution pattern of the phenyl-ring in position 1 on the affinity for the orphanin FQ receptor and selectivity to opioid (mu, kappa, delta) receptors is discussed. The most interesting compound 1c was tested for its anxiolytic-like properties in vivo.

  3. 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

  4. Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-phenyl-3-substituted quinazolin-4(3H) ones.

    PubMed

    Alagarsamy, Veerachamy; Salomon, Viswas Raja; Vanikavitha, Gnanavel; Paluchamy, Veeran; Chandran, Muniyandi Ravi; Sujin, Augustin Arnald; Thangathiruppathy, Arunachalam; Amuthalakshmi, Sivaperuman; Revathi, Rajappan

    2002-11-01

    A series of novel 2-phenyl-3-substituted quinazolin-4(3H)-ones have been synthesized by treating methyl-N-(2-phenyl quinazolin-3-yl-4(3H)-one) dithiocarbamate with different amines, the starting material dithiocarbamate was synthesized from anthranilic acid. The title compounds were investigated for analgesic, anti-inflammatory and antibacterial activities. All the test compounds exhibited significant activity, the compounds A1, A2 and A3 shown more potent analgesic activity, and the compound A3 shown more potent anti-inflammatory activity than the reference standard diclofenac sodium.

  5. Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.

    PubMed

    Das, Bhaskar C; Mohapatra, Seetaram; Campbell, Philip D; Nayak, Sabita; Mahalingam, Sakkarapalayam M; Evans, Todd

    2010-05-01

    Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets.

  6. 2-(2-Fluoro­phen­yl)-3-methyl­sulfanyl-5-phenyl-1-benzo­furan

    PubMed Central

    Choi, Hong Dae; Seo, Pil Ja; Lee, Uk

    2013-01-01

    In the title compound, C21H15FOS, the dihedral angles between the mean plane [r.m.s. deviation = 0.041 (1) Å] of the benzo­furan fragment and the pendant 2-fluoro­phenyl and phenyl rings are 46.09 (3) and 24.34 (5)°, respectively. In the crystal, mol­ecules are linked by weak C—H⋯π inter­actions, forming a three-dimensional network. PMID:23723873

  7. Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans.

    PubMed

    Wang, Shihua; Li, Pinhua; Yu, Lin; Wang, Lei

    2011-11-18

    Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.

  8. Synthesis and biological evaluation of substituted 2-phenyl-2H-indazole-7-carboxamides as potent poly(ADP-ribose) polymerase (PARP) inhibitors.

    PubMed

    Scarpelli, Rita; Boueres, Julia K; Cerretani, Mauro; Ferrigno, Federica; Ontoria, Jesus M; Rowley, Michael; Schultz-Fademrecht, Carsten; Toniatti, Carlo; Jones, Philip

    2010-01-15

    A potent series of substituted 2-phenyl-2H-indazole-7-carboxamides were synthesized and evaluated as inhibitors of poly (ADP-ribose) polymerase (PARP). This extensive SAR exploration culminated with the identification of substituted 5-fluoro-2-phenyl-2H-indazole-7-carboxamide analog 48 which displayed excellent PARP enzyme inhibition with IC(50)=4nM, inhibited proliferation of cancer cell lines deficient in BRCA-1 with CC(50)=42nM and showed encouraging pharmacokinetic properties in rats compared to the lead 6.

  9. Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1H-phenalen-1-one: a functional group exclusion approach.

    PubMed

    Duque, Luisa; Zapata, Carolina; Rojano, Benjamín; Schneider, Bernd; Otálvaro, Felipe

    2013-07-19

    2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elata, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore the effect of each functional group. H-Atom transfer from the phenolic hydroxyl, a captodative effect from the hydroxy ketone, and the presumed involvement of the phenyl ring in the termination step of the radical reaction were disclosed as relevant features of this type of antioxidant.

  10. 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.

  11. 2,5-disubstituted oxazole research: fluorescence quantum yields and laser conversion efficiencies of 2-(p-italic-biphenyl)-5-phenyl oxazole and its 5-p-italic-substituted derivatives

    SciTech Connect

    Yu Peifeng

    1986-03-01

    The fluorescence quantum yield and laser conversion efficiency of 2-(p-italic-biphenyl)-5-phenyl-oxazole and thirteen 5-substituted phenyl derivatives are measured. A brief discussion is also given on the relation between the subtituent effects and spectral properties of the compounds.

  12. Homo-C-nucleoside analogs III. Studies on the base-catalyzed dehydrative cyclization of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole.

    PubMed

    Sallam, Mohammed A E

    2010-10-13

    Treatment of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole with one molar equivalent of 2,4,6-triisopropylbenzenesulfonyl chloride (TIBSCl) in pyridine solution afforded the homo-C-nucleoside analog; 4-(2,5-anhydro-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole in 54% yield and 4-(α-d-arabinopyranosyl)-2-phenyl-2H1,2,3-triazole analog in 3% yield. The 4-(5-O-triisopropylbenzenesulfonyl)-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole analog was isolated as an intermediate and identified as its tetra-O-acetyl derivative. The 4-(5-chloro-5-deoxy-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole analog was isolated as a byproduct. The structure and anomeric configuration of the products were determined by acylation, NMR spectroscopy, and mass spectrometry.

  13. Crystal structure of 1-phenyl­imido-1-{6-[1-(phenyl­imino)­eth­yl]pyridin-2-yl}ethan-1-yl-κ3 N,N′,N′′)iron(II)

    PubMed Central

    Lau, Ka-Cheong; Filatov, Alexander S.; Jordan, Richard F.

    2016-01-01

    The title iron complex, [Fe(C21H19N3)2], consists of an FeII atom chelated by two tridentate bis­(imino)­pyridine radical anions in a slightly distorted octa­hedral coordination environment. In the solid state, there are two independent half-mol­ecules in the asymmetric unit, and the complete mol­ecular structure is formed by applying twofold rotation symmetry with the twofold rotation axis passing through an Fe atom. In the crystal, the Fe-containing complexes are not involved in any particular direct inter­molecular inter­actions, with the shortest C—HAr contacts between neighboring phenyl groups being ca 3.2 Å. PMID:27840716

  14. 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.

  15. Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor.

    PubMed

    Lapierre, Jean-Marc; Eathiraj, Sudharshan; Vensel, David; Liu, Yanbin; Bull, Cathy O; Cornell-Kennon, Susan; Iimura, Shin; Kelleher, Eugene W; Kizer, Darin E; Koerner, Steffi; Makhija, Sapna; Matsuda, Akihisa; Moussa, Magdi; Namdev, Nivedita; Savage, Ronald E; Szwaya, Jeff; Volckova, Erika; Westlund, Neil; Wu, Hui; Schwartz, Brian

    2016-07-14

    The work in this paper describes the optimization of the 3-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine chemical series as potent, selective allosteric inhibitors of AKT kinases, leading to the discovery of ARQ 092 (21a). The cocrystal structure of compound 21a bound to full-length AKT1 confirmed the allosteric mode of inhibition of this chemical class and the role of the cyclobutylamine moiety. Compound 21a demonstrated high enzymatic potency against AKT1, AKT2, and AKT3, as well as potent cellular inhibition of AKT activation and the phosphorylation of the downstream target PRAS40. Compound 21a also served as a potent inhibitor of the AKT1-E17K mutant protein and inhibited tumor growth in a human xenograft mouse model of endometrial adenocarcinoma.

  16. Reactivity of N-Phenyl-1-Aza-2-Cyano-1,3-Butadienes in the Diels-Alder Reaction.

    PubMed

    Sisti, Nicholas J.; Motorina, Irina A.; Tran Huu Dau, Marie-Elise; Riche, Claude; Fowler, Frank W.; Grierson, David S.

    1996-05-31

    It is found that N-phenyl-2-cyano-1-azadiene 4, prepared via a two-step, one-pot, sequence from acrylanilide, undergoes efficient [4 + 2] cycloaddition with a complete range of electron rich, electron poor, and neutral dienophiles under remarkably mild thermal conditions (90-120 degrees C for 20-48 h). Regiospecific formation of the alpha-cycloadduct wherein the dienophile substituent is alpha to nitrogen is observed for vinyl ethers and styrene, whereas the Diels-Alder reactions with methyl acrylate and methyl vinyl ketone (MVK) produce alpha/beta mixtures in which the alpha-cycloadduct is the major regioisomer (approximately 4-5:1). An essentially identical reaction pattern was observed in the Diels-Alder reaction of N-(p-methoxyphenyl)-2-cyano-1-azadiene 18 and the 4-methyl-substituted azadiene 27. For compound 19 derived from cycloaddition of 18 with ethyl vinyl ether, facile conversion to the dihydropyridine 21 through loss of EtOH on brief acid treatment was also noted. The 2,4-cis-disubstitution pattern confirmed by X-ray diffraction for the major cycloadduct 29 isolated from the reaction of 27 with styrene provides evidence for the endo mode of cycloaddition in the Diels-Alder reaction of N-phenyl(aryl)-2-cyano-1-azadienes. Calculation of the frontier orbital energies and coefficients, as well as the transition state geometries for the [4 + 2] cycloaddition of N-phenyl-2-cyano-1-azadiene 4 with methyl vinyl ether, styrene, and MVK were carried out at the RHF AM1 level (MOPAC, Version 5.0). The FMO treatment indicates that the reaction of 4 with methyl vinyl ether occurs under LUMO(diene) control, whereas in contrast, the corresponding cycloaddition with MVK occurs preferably under HOMO(diene) control. A high degree of asynchronicity is observed in the calculated transition states for reaction of 4 with the three representative dienophiles. In all cases the transition states leading to the alpha-cycloadducts are lower in energy than those giving the beta

  17. INHIBITION OF JNK AND P38 MAPK PHOSPHORYLATION BY 5-(ACETYLAMINO)-4-OXO-6-PHENYL-2-HEXENOIC ACID METHYL ESTER AND 4-PHENYL-BUTENOIC ACID DECREASES SUBSTANCE P-INDUCED TNF-α UPREGULATION IN MACROPHAGES

    PubMed Central

    Lucrezi, Jacob; Burns, Timothy J.; Matesic, Diane F.; Oldham, Charlie; May, Sheldon W.

    2014-01-01

    The interactions between the immune and nervous systems play an important role in immune and inflammatory conditions. Substance P (SP), the unidecapeptide RPKPQQFFGLM-NH2, is known to upregulate the production of pro-inflammatory cytokines such as tumor necrosis factor (TNF)-α. We report here that 5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid methyl ester (AOPHA-Me) and 4-phenyl-3-butenoic acid (PBA), two anti-inflammatory compounds developed in our laboratory, reduce SP-stimulated TNF-α expression in RAW 264.7 macrophages. We also show that AOPHA-Me and PBA both inhibit SP-stimulated phosphorylation of JNK and p38 MAPK. Furthermore, molecular modeling studies indicate that both AOPHA-Me and PBA dock at the ATP binding site of apoptosis signal-regulating kinase 1 (ASK1), a member of the MAPKs upstream of both JNK and p38 MAPK, with predicted interaction energies of −7.0 kcal/mol and −5.9 kcal/mol, respectively; this binding overlaps with that of staurosporine, a known inhibitor of ASK1. Taken together, these findings suggest that AOPHA-Me and PBA inhibition of TNF-α expression in SP-stimulated RAW 264.7 macrophages is a consequence of the inhibition JNK and p38 MAPK phosphorylation. We have previously shown that AOPHA-Me and PBA inhibit the amidative bioactivation of SP, which also would be expected to decrease formation of pro-inflammatory cytokines. It is conceivable that this dual action of inhibiting amidation and MAPK phosphorylation may be of some advantage in enhancing the anti-inflammatory activity of a therapeutic molecule. PMID:24746749

  18. 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…

  19. 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

  20. Synthesis and evaluation of 3-amino/guanidine substituted phenyl oxazoles as a novel class of LSD1 inhibitors with anti-proliferative properties.

    PubMed

    Dulla, Balakrishna; Kirla, Krishna Tulasi; Rathore, Vandana; Deora, Girdhar Singh; Kavela, Sridhar; Maddika, Subbareddy; Chatti, Kiranam; Reiser, Oliver; Iqbal, Javed; Pal, Manojit

    2013-05-21

    A series of functionalized phenyl oxazole derivatives was designed, synthesized and screened in vitro for their activities against LSD1 and for effects on viability of cervical and breast cancer cells, and in vivo for effects using zebrafish embryos. These compounds are likely to act via multiple epigenetic mechanisms specific to cancer cells including LSD1 inhibition.