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Sample records for benzoxazoles

  1. Benzoxazoles and oxazolopyridines in medicinal chemistry studies

    DEFF Research Database (Denmark)

    Demmer, Charles S; Bunch, Lennart

    2015-01-01

    and the use of benzoxazole as a bioisostere are discussed. The review is extended to cover structure-activity relationship studies of 2-substituted benzoxazoles, 2-substituted oxazolopyridines, and in perspective, application of the recently published novel heterocycle oxazolopyrazine in medicinal chemistry......The benzoxazole heterocycle is often found in ligands targeting a plethora of receptors and enzymes. By analysis of published X-ray structures, this review aims at highlighting key interactions which the benzoxazole may engage in with its host protein. Furthermore, bioavailability, metabolism...

  2. Benzoxazoles and oxazolopyridines in medicinal chemistry studies.

    Science.gov (United States)

    Demmer, Charles S; Bunch, Lennart

    2015-06-05

    The benzoxazole heterocycle is often found in ligands targeting a plethora of receptors and enzymes. By analysis of published X-ray structures, this review aims at highlighting key interactions which the benzoxazole may engage in with its host protein. Furthermore, bioavailability, metabolism and the use of benzoxazole as a bioisostere are discussed. The review is extended to cover structure-activity relationship studies of 2-substituted benzoxazoles, 2-substituted oxazolopyridines, and in perspective, application of the recently published novel heterocycle oxazolopyrazine in medicinal chemistry studies.

  3. Crystal structure and stereochemistry study of 2-substituted benzoxazole derivatives.

    Science.gov (United States)

    Mabied, Ahmed F; Shalaby, Elsayed M; Zayed, Hamdia A; El-Kholy, Esmat; Farag, Ibrahim S A; Ahmed, Naima A

    2014-01-01

    The structure of 2-[(4-chlorophenylazo) cyanomethyl] benzoxazole, C15H9ClN4O (I), has triclinic ([Formula: see text]) symmetry. The structure displays N-H ⋯ N hydrogen bonding. The structure of 2-[(arylidene) cyanomethyl] benzoxazoles, C17H10N2O3 (II), has triclinic ([Formula: see text]) symmetry. The structure displays C-H ⋯ N, C-H ⋯ C hydrogen bonding. In (I), the chlorophenyl and benzoxazole groups adopt a trans configuration with respect to the central cyanomethyle hydrazone moiety. Compound (II) crystallized with two molecules in the asymmetric unit shows cisoid conformation between cyano group and benzoxazole nitrogen, contrary to (I). In (II) the benzodioxole has an envelope conformation (the C17 atom is the flap atom). The molecular geometry obtained using molecular mechanics (MM) calculations has been discussed along with the results of single crystal analysis.

  4. Antibacterial and antifungal activities of benzimidazole and benzoxazole derivatives.

    OpenAIRE

    Elnima, E I; Zubair, M U; Al-Badr, A A

    1981-01-01

    The in vitro antibacterial and antifungal activities of six benzimidazole and benzoxazole derivatives were tested against standard strains and 59 clinical isolates. Of the six compounds, only compounds II and III (both benzoxazoles) were active, whereas the rest were devoid of any activity. Considerable growth inhibition of all of the standard strains, including fungi and gram-positive and gram-negative bacteria, resulted when they were treated with these compounds. Fifty-nine clinical isolat...

  5. Heterocyclic benzoxazole-based liquid crystals: Synthesis and mesomorphic properties

    Institute of Scientific and Technical Information of China (English)

    Sie Tiong Ha; Kok Leei Foo; Ramesh T. Subramaniam; Masato M. Ito; S. Sreehari Sastry; Siew Teng Ong

    2011-01-01

    New Schiff base liquid crystals containing benzoxazole core and alkanoyloxy chain at the end group of the molecules (Cn-1H2n-1COO-, n= 14,16,18) was synthesized. The present compounds are enantiotropic smectic A liquid crystals. It was also found that the end groups of the molecules and polar chloro substituent at the benzoxazole fragment had effect on the mesomorphic properties.

  6. 2-Arylbenzoxazoles as CETP inhibitors: Substitution of the benzoxazole moiety.

    Science.gov (United States)

    Smith, Cameron J; Ali, Amjad; Chen, Liya; Hammond, Milton L; Anderson, Matt S; Chen, Ying; Eveland, Suzanne S; Guo, Qiu; Hyland, Sheryl A; Milot, Denise P; Sparrow, Carl P; Wright, Samuel D; Sinclair, Peter J

    2010-01-01

    A series of 2-arylbenzoxazole inhibitors of the cholesterol ester transfer protein (CETP) is described. Structure-activity studies focused on variation of the substitution of the benzoxazole moiety. Substitution at the 5- and 7-positions of the benzoxazole moiety was found to be beneficial for CETP inhibition. Compound 47 was found to be the most potent inhibitor in this series and inhibited CETP with an IC(50) of 28nM.

  7. 2-Methyl-1,3-benzoxazol-4-yl diphenylphosphinate

    Directory of Open Access Journals (Sweden)

    Dewald J. Kleinhans

    2011-02-01

    Full Text Available The title compound, C20H16NO3P, was synthesized by the addition of diphenylphosphine chloride to a tetrahydrofuran solution of Et3N and 2-methyl-1,3-benzoxazol-4-ol at 233 K. In the molecule, the almost planar (r.m.s. deviation = 0.010 Å benzoxazole moiety is attached to the slightly distorted tetrahedral P atom [C—P—C—C torsion angle = 132.20 (18°]. The crystal structure does not exhibit any significant intermolecular interactions.

  8. A novel thermooxidatively stable poly(ester-imide-benzoxazole)

    Energy Technology Data Exchange (ETDEWEB)

    Sundar, R.A.; Mathias, L.J. [Univ. of Sothern Mississippi, Hattiesburg, MS (United States)

    1993-12-31

    A poly(ester-amide-imide) was synthesized by the low temperature solution polycondensation of 4-amino-5-hydroxy-N,4{prime}-hydroxyphenyl phthalimide with isophthaloyl chloride. Subsequent thermal cyclodehydration of the poly(ester-amide-imide) at 320{degrees}C in vacuum afforded the poly(ester-imide-benzoxazole). This polymer was only soluble in sulfuric acid. FTIR and NMR spectra confirmed structure. The poly(ester-imide-benzoxazole) had no detectable thermal transitions up to 500{degrees}C in nitrogen, and was reasonably stable in air and nitrogen, with weight retentions of 95% at 500{degrees}C.

  9. 3-[Chloro(phenylmethyl]-6-methyl-1,2-benzoxazole

    Directory of Open Access Journals (Sweden)

    M. Kayalvizhi

    2011-11-01

    Full Text Available The title compound, C15H12ClNO, is a functionalized 1,2-benzoxazole with a chloro(phenylmethyl substituent. The molecule is V-shaped, the dihedral angle between the mean plane of the 1,2-benzoxazole system [maximum deviation = 0.023 (3 Å for the N atom] and the phenyl ring being 70.33 (14°. There are no hydrogen-bonding interactions in the crystal structure, which is stabilized by van der Waals interactions only.

  10. Design, synthesis and biological estimation of 1-(benzoxazole-2-y1)piperazine and 4-(benzoxazole-2-yl)piperidine derivatives as potential α1-AR antagonists

    Institute of Scientific and Technical Information of China (English)

    Jia Bin Li; Lin Xia; Bin Wu; Tao Wang; Zhen Zhou Jiang

    2008-01-01

    Two series of 1-(benzoxazole-2-yl)piperazine(8a-i)and 4-(benzoxazole-2-yl)piperidine compounds(10a-i)were designed,synthesized and evaluated for their α1-AR antagonistic activities.Biological assay in vitro indicated that 10h showed slightly stronger α1-AR antagonistic activity to that of our lead compound 1.

  11. A triphenylamine-based benzoxazole derivative as a high-contrast piezofluorochromic material induced by protonation.

    Science.gov (United States)

    Xue, Pengchong; Chen, Peng; Jia, Junhui; Xu, Qiuxia; Sun, Jiabao; Yao, Boqi; Zhang, Zhenqi; Lu, Ran

    2014-03-11

    A triphenylamine-based benzoxazole derivative exhibits a low contrast piezofluorochromic behavior under external pressure, and a high-contrast fluorescence change induced by protonation can be observed.

  12. The thermodynamic properties of benzothiazole and benzoxazole

    Energy Technology Data Exchange (ETDEWEB)

    Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.

    1991-08-01

    This research program, funded by the Department of Energy, Office of Fossil Energy, Advanced Extraction and Process Technology, provides accurate experimental thermochemical and thermophysical properties for key'' organic diheteroatom-containing compounds present in heavy petroleum feedstocks, and applies the experimental information to thermodynamic analyses of key hydrodesulfurization, hydrodenitrogenation, and hydrodeoxygenation reaction networks. Thermodynamic analyses, based on accurate information, provide insights for the design of cost-effective methods of heteroatom removal. The results reported here, and in a companion report to be completed, will point the way to the development of new methods of heteroatom removal from heavy petroleum. Measurements leading to the calculation of the ideal-gas thermodynamic properties are reported for benzothiazole and benzoxazole. Experimental methods included combustion calorimetry, adiabatic heat-capacity calorimetry, comparative ebulliometry, inclinded-piston gauge manometry, and differential-scanning calorimetry (d.s.c). Critical property estimates are made for both compounds. Entropies, enthalpies, and Gibbs energies of formation were derived for the ideal gas for both compounds for selected temperatures between 280 K and near 650 K. The Gibbs energies of formation will be used in a subsequent report in thermodynamic calculations to study the reaction pathways for the removal of the heteratoms by hydrogenolysis. The results obtained in this research are compared with values present in the literature. The failure of a previous adiabatic heat capacity study to see the phase transition in benzothiazole is noted. Literature vibrational frequency assignments were used to calculate ideal gas entropies in the temperature range reported here for both compounds. Resulting large deviations show the need for a revision of those assignments. 68 refs., 6 figs., 15 tabs.

  13. An efficient and green synthesis of novel benzoxazole under ultrasound irradiation.

    Science.gov (United States)

    Nikpassand, Mohammad; Fekri, Leila Zare; Farokhian, Pegah

    2016-01-01

    Ultrasound as green process and an alternative energy source was investigated for the environmentally benign synthesis of novel benzoxazoles from different azo-linked salicylic acid derivatives and 2-amino-4-chlorophenol in short reaction time and high yield. These benzoxazole compounds have been characterized by elemental analysis, FT-IR, (1)H NMR and (13)C NMR spectroscopy.

  14. 2-(1,3-Benzoxazol-2-yl-1-phenylethenyl benzoate

    Directory of Open Access Journals (Sweden)

    Mohammad Hassan Ghorbani

    2011-10-01

    Full Text Available In the title molecule, C22H15NO3, the configuration about the ethylenic double bond is Z configuration and it is approximately coplanar with the adjacent phenyl ring and benzoxazole ring system as indicated by the C(H=C(O—Cphenyl—Cphenyl and Obenzoxazole—C—C(H=C(O torsion angles of 179.88 (15 and 5.7 (2°, respectively. The dihedral angle between the essentially planar (r.m.s. deviation = 0.080 Å 2-(1,3-benzoxazol-2-yl-1-phenylethenyl group and the benzoate phenyl ring is 61.51 (6°. A short intramolecular O...O non-bonded interaction of 2.651 (2 Å is present.

  15. 2-(1,3-Benzoxazol-2-ylsulfanyl-1-phenylethanone

    Directory of Open Access Journals (Sweden)

    Hossein Loghmani-Khouzani

    2009-09-01

    Full Text Available In the title compound, C15H11NO2S, a new thio-benzoxazole derivative, the dihedral angle between the benzoxazole ring and the phenyl ring is 9.91 (9°. An interesting 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, molecules are linked together by zigzag intermolecular C—H...N interactions into a column along the a axis. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid = 3.8048 (10 Å].

  16. 2-(4-Aminophenyl-1,3-benzoxazole

    Directory of Open Access Journals (Sweden)

    Yuan Qu

    2008-07-01

    Full Text Available In the title molecule, C13H10N2O, the dihedral angle between the benzoxazole ring system and the benzene ring is 11.8 (1°. In the crystal structure, molecules are linked by intermolecular N—H...N hydrogen bonds and π...π interactions [centroid–centroid distance = 3.6560 (15 Å] to form a two-dimensional network.

  17. SYNTHESIS THROUGH MICROWAVE IRRADIATION, CHARACTERIZATION AND EVALUATION OF ANTIMICROBIAL ACTIVITY OF 2-PHENYL-1, 3-BENZOXAZOLE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    Tariq Sana

    2012-09-01

    Full Text Available A series of 2-phenyl-1,3-benzoxazoles were synthesized by the reaction of 2-aminophenol and acyl chlorides using microwave irradiation. Purity of compounds was determined by TLC. All the synthesized compounds were characterized by spectral analysis (FTIR, 1H-NMR . The compounds were evaluated for in vitro antimicrobial activity against Bacillus pumilus, Bacillus subtilis (Gram positive; Escherichia coli, Pseudomonas aeruginosa (Gram negative and Candida albicans and Aspergillus niger by agar-well diffusion method at 2.5, 5, 10mg/ml. Compounds 2-(2-methoxyphenyl-1,3-benzoxazole, 2-(4-bromophenyl-1,3-benzoxazole, 2-(3-cholorophenyl-1,3-benzoxazole, 2-(2-nitrophenyl-1,3-benzoxazole have been found to have good antibacterial activity. Compounds 2-pheny-1,3-benzoxazole, 2-(4-bromophenyl-1,3-benzoxazole, were potent antifungal compounds amongst the series.

  18. Benzoxazole piperidines as selective and potent somatostatin receptor subtype 5 antagonists.

    Science.gov (United States)

    Martin, Rainer E; Mohr, Peter; Maerki, Hans Peter; Guba, Wolfgang; Kuratli, Christoph; Gavelle, Olivier; Binggeli, Alfred; Bendels, Stefanie; Alvarez-Sánchez, Rubén; Alker, André; Polonchuk, Liudmila; Christ, Andreas D

    2009-11-01

    SAR studies of a recently described SST5R selective benzoxazole piperidine lead series are described with particular focus on the substitution pattern on the benzyl and benzoxazole side-chains. Introduction of a second meta substituent at the benzyl unit significantly lowers residual hH1 activity and insertion of substituents onto the benzoxazole periphery entirely removes remaining h5-HT2B activity. Compounds with single digit nM activity, functional antagonism and favorable physicochemical properties endowed with a good pharmacokinetic profile in rats are described which should become valuable tools for exploring the pharmacological role of the SST5 receptor in vivo.

  19. Novel benzoxazole inhibitors of mPGES-1.

    Science.gov (United States)

    Kablaoui, Natasha; Patel, Snahel; Shao, Jay; Demian, Douglas; Hoffmaster, Keith; Berlioz, Francioise; Vazquez, Michael L; Moore, William M; Nugent, Richard A

    2013-02-01

    A novel series of potent benzoxazole mPGES-1 inhibitors has been derived from a hit from a high throughput screen. Compound 37 displays mPGES-1 inhibition in an enzyme assay (0.018 μM) and PGE-2 inhibition in a cell-based assay (0.034 μM). It demonstrates 500- and 2500-fold selectivity for mPGES-1 over COX-2 and 6-keto PGF-1α, respectively. In vivo PK studies in dogs demonstrate 55% oral bioavailability and an 7 h half-life.

  20. 2-(1,3-Benzoxazol-2-ylguanidinium chloride

    Directory of Open Access Journals (Sweden)

    Shaaban K. Mohamed

    2011-11-01

    Full Text Available The non-H atoms of the cation of the title salt, C8H9N4O+·Cl−, are approximately co-planar (r.m.s. deviation = 0.024 Å with one amino group forming an intramolecular hydrogen bond to the tertiary N atom of the benzoxazole fused-ring system. The cations and anions are linked by cyclic R21(6 N—H...Cl hydrogen-bonding associations, generating linear chains running along the a-axis direction.

  1. Efficient Syntheses of 2-Substituted Benzimidazoles and Benzoxazoles from β-Keto Esters

    Institute of Scientific and Technical Information of China (English)

    XIAO Li-wei; ZHANG Min; SUN Wen-hua

    2011-01-01

    An efficient synthetic method was developed to synthesize 2-substituted benzimidazoles and benzoxazoles withβ-keto esters as starting materials under mild reaction conditions, during which other functional groups are bearable from reactants to products.

  2. Copper-catalysed intramolecular O-arylation: a simple and efficient method for benzoxazole synthesis.

    Science.gov (United States)

    Wu, Fengtian; Zhang, Jie; Wei, Qianbing; Liu, Ping; Xie, Jianwei; Jiang, Haojie; Dai, Bin

    2014-12-21

    A wide range of 2-substituted benzoxazoles can be efficiently synthesized from N-(2-iodo-/bromo-phenyl)benzamides, and even the less reactive N-(2-chlorophenyl)benzamides, via Cu-catalysed intramolecular coupling cyclization reactions using methyl 2-methoxybenzoate as the ligand under mild reaction conditions. In addition, the benzoxazoles can be easily prepared from the primary amides coupling with o-dihalobenzenes in a single step.

  3. Time dependent density functional study of the absorption spectra of 1,3-benzoxazole and three substituted benzoxazole in gas phase and liquid phase

    Energy Technology Data Exchange (ETDEWEB)

    Carrasquilla, Rafael J; Neira, Oscar L, E-mail: rjcarrasquilla@yahoo.com [Grupo de Espectroscopia Optica y Laser, Universidad Popular del Cesar, Valledupar (Colombia)

    2011-01-01

    Time dependent density functional (TD-DFT) calculations were performed on 1,3-benzoxazole and substituted benzoxazoles using the B3LYP functional and the 6-31+G(d) basis sets. The geometry of the S{sub 0} and S{sub 1} singlet ground and excited states were optimized in gas phase, toluene and methanol using B3LYP/6-31+G(d) y CIS/6-31+G(d) methods, respectively, and the vertical {pi} {yields} {pi}{sup *} absorption largest wavelength transitions were determined. Several global molecular descriptors were considered such as the hardness, chemical potential, electronegativity and the dipole moment for each molecule and was determined the influence that has, about the values of these descriptors, the alteration of the main molecular chain of an initial structure (1,3 not substituted Benzoxazole). Generally, the predicted spectra are in agreement with the experimental data.

  4. 1,3-Benzoxazole-4-carbonitrile as a novel antifungal scaffold of β-1,6-glucan synthesis inhibitors.

    Science.gov (United States)

    Kuroyanagi, Jun-ichi; Kanai, Kazuo; Sugimoto, Yuuichi; Horiuchi, Takao; Achiwa, Issei; Takeshita, Hiroshi; Kawakami, Katsuhiro

    2010-11-01

    Synthesis and in vitro antifungal evaluations of 1,3-benzoxazole-7-carbonitrile 3, 1,3-benzoxazole-4-carbonitrile 4, benzofuran 5, benzoxazine 7, and benzimidazole 8 were reported. Among them, 1,3-benzoxazole-4-carbonitrile was found to be a superior scaffold structure with moderate growth inhibition against Candida species. 1,3-Benzoxazole-4-carbonitrile 6 showed potent activity against Candida species compared to 5-desmethyl compound 4 and triazolopyridine 2. Compound 6 was efficiently prepared from versatile intermediate 24, which possessed six different substituents on the benzene ring. Conversion of benzene 24 into various 1,3-benzoxazole derivatives such as 2-aliphatic 34, 2-amino 35, and lactone 38 was demonstrated.

  5. In vitro antifungal activity of 2-(2'-hydroxy-5'-aminophenyl)benzoxazole in Candida spp. strains.

    Science.gov (United States)

    Daboit, Tatiane Caroline; Stopiglia, Cheila Denise Ottonelli; Carissimi, Mariana; Corbellini, Valeriano Antonio; Stefani, Valter; Scroferneker, Maria Lúcia

    2009-11-01

    The development of azole antifungals has allowed for the treatment of several fungal infections. However, the use of these compounds is restricted because of their hepatotoxicity or because they need to be administered together with other drugs in order to prevent resistance to monotherapy. Benzoxazole derivatives are among the most thriving molecular prototypes for the development of antifungal agents. 2-(2'-hydroxyphenyl) benzoxazoles are versatile molecules that emit fluorescence and have antibacterial, antiviral and antifungal properties. 2-(2'-hydroxy-5'-aminophenyl) benzoxazole (HAMBO) was tested against Candida yeast. The inhibition provided by HAMBO was lower than that of fluconazole, showing low antifungal activity against Candida spp., but equivalent to that of benzoxazoles tested in similar studies. HAMBO showed fungistatic activity against all analysed strains. This class of novel benzoxazole compounds may be used as template to produce better antifungal drugs.

  6. 2-(4-Methyl-phen-yl)-6-nitro-1,3-benzoxazole.

    Science.gov (United States)

    Centore, Roberto; Piccialli, Vincenzo; Tuzi, Angela

    2013-05-01

    The title compound, C14H10N2O3, is a π-conjugated mol-ecule containing a benzoxazole aromatic fused heterobicycle. The benzoxazole ring system is planar within 0.01 Å. The mol-ecule assumes an approximately flat conformation, the benzoxazole ring system forming dihedral angles of 6.52 (12) and 7.4 (3)° with the benzene ring and the nitro group, respectively. In the crystal, mol-ecules are connected by very weak C-H⋯O hydrogen inter-actions, forming chains running parallel to the a or c axes. The methyl H atoms are disordered over two sets of sites of equal occupancy rotated by 60°.

  7. Preparation and in vitro evaluation of benzylsulfanyl benzoxazole derivatives as potential antituberculosis agents.

    Science.gov (United States)

    Klimesová, Vera; Kocí, Jan; Waisser, Karel; Kaustová, Jarmila; Möllmann, Ute

    2009-05-01

    A set of 2-benzylsulfanyl derivatives of benzoxazole was synthesized and evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis, non-tuberculous mycobacteria and multidrug-resistant M. tuberculosis. The activities were expressed as the minimum inhibitory concentration (MIC) in mmol/L. The substances showed similar activity against all tested strains. The lead compounds in the set, dinitro derivatives exhibited significant activity against both sensitive and resistant strains of M. tuberculosis and also against non-tuberculous mycobacteria. To facilitate drug design of benzoxazole as potential antituberculosis agent, we have explored the quantitative structure-activity relationship (QSAR). We demonstrated that lower lipophilicity has significant contribution to activity. Dinitrobenzylsulfanyl derivative of benzoxazole represents the promising small-molecule synthetic antimycobacterials.

  8. A chemometric approach for prediction of antifungal activity of some benzoxazole derivatives against Candida albicans

    Directory of Open Access Journals (Sweden)

    Podunavac-Kuzmanović Sanja O.

    2012-01-01

    Full Text Available The purpose of the article is to promote and facilitate prediction of antifungal activity of the investigated series of benzoxazoles against Candida albicans. The clinical importance of this investigation is to simplify design of new antifungal agents against the fungi which can cause serious illnesses in humans. Quantitative structure activity relationship analysis was applied on nineteen benzoxazole derivatives. A multiple linear regression (MLR procedure was used to model the relationships between the molecular descriptors and the antifungal activity of benzoxazole derivatives. Two mathematical models have been developed as a calibration models for predicting the inhibitory activity of this class of compounds against Candida albicans. The quality of the models was validated by the leave-one-out technique, as well as by the calculation of statistical parameters for the established model. [Projekat Ministarstva nauke Republike Srbije, br. 172012 i br. 172014

  9. 3-[Chloro-(phen-yl)meth-yl]-6-methyl-1,2-benzoxazole.

    Science.gov (United States)

    Kayalvizhi, M; Vasuki, G; Ramamurthi, K; Veerareddy, A; Laxminarasimha, G

    2011-11-01

    The title compound, C(15)H(12)ClNO, is a functionalized 1,2-benzoxazole with a chloro-(phen-yl)methyl substituent. The mol-ecule is V-shaped, the dihedral angle between the mean plane of the 1,2-benzoxazole system [maximum deviation = 0.023 (3) Å for the N atom] and the phenyl ring being 70.33 (14)°. There are no hydrogen-bonding inter-actions in the crystal structure, which is stabilized by van der Waals inter-actions only.

  10. Design, Synthesis, and Cytotoxicity of 5-Fluoro-2-methyl-6-(4-aryl-piperazin-1-yl Benzoxazoles

    Directory of Open Access Journals (Sweden)

    Thuraya Al-Harthy

    2016-09-01

    Full Text Available To design new compounds suitable as starting points for anticancer drug development, we have synthesized a novel series of benzoxazoles with pharmaceutically advantageous piperazine and fluorine moieties attached to them. The newly synthesized benzoxazoles and their corresponding precursors were evaluated for cytotoxicity on human A-549 lung carcinoma cells and non-cancer HepaRG hepatocyes. Some of these new benzoxazoles show potential anticancer activity, while two of the intermediates show lung cancer selective properties at low concentrations where healthy cells are unaffected, indicating a selectivity window for anticancer compounds.

  11. Synthesis, characterization, and spectroscopic investigation of benzoxazole conjugated Schiff bases.

    Science.gov (United States)

    Santos, Fabiano S; Costa, Tania M H; Stefani, Valter; Gonçalves, Paulo F B; Descalzo, Rodrigo R; Benvenutti, Edilson V; Rodembusch, Fabiano S

    2011-11-24

    Two Schiff bases were synthesized by reaction of 2-(4'-aminophenyl)benzoxazole derivatives with 4-N,N-diethylaminobenzaldehyde. UV-visible (UV-vis) and steady-state fluorescence in solution were applied in order to characterize its photophysical behavior. The Schiff bases present absorption in the UV region with fluorescence emission in the blue-green region, with a large Stokes' shift. The UV-vis data indicates that each dye behaves as two different chromophores in solution in the ground state. The fluorescence emission spectra of the dye 5a show that an intramolecular proton transfer (ESIPT) mechanism takes place in the excited state, whereas a twisted internal charge transfer (TICT) state is observed for the dye 5b. Theoretical calculations were performed in order to study the conformation and polarity of the molecules at their ground and excited electronic states. Using density functional theory (DFT) methods at theoretical levels BLYP/Aug-SV(P) for geometry optimizations and B3LYP/6-311++G(2d,p) for single-point energy evaluations, the calculations indicate that the lowest energy conformations are in all cases nonplanar and that the dipole moments of the excited state relaxed structures are much larger than those of the ground state structures, which corroborates the experimental UV-vis absorption results.

  12. Synthesis of substituted benzoxazoles by the iron(Ⅲ)-catalyzed aerobic oxidation process

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    The FeCl3-catalyzed aerobic oxidation process for the synthesis of benzoxazoles,benzothiazole and benzimidazole has been discovered.This method has proved to be effective to a wide range of substrates,and it has been applied for the synthesis of JTP-426467.

  13. 2-Amino-7-substituted benzoxazole analogs as potent RSK2 inhibitors.

    Science.gov (United States)

    Costales, Abran; Mathur, Michelle; Ramurthy, Savithri; Lan, Jiong; Subramanian, Sharadha; Jain, Rama; Atallah, Gordana; Setti, Lina; Lindvall, Mika; Appleton, Brent A; Ornelas, Elizabeth; Feucht, Paul; Warne, Bob; Doyle, Laura; Basham, Stephen E; Aronchik, Ida; Jefferson, Anne B; Shafer, Cynthia M

    2014-03-15

    2-Amino-7-substituted benzoxazole analogs were identified by HTS as inhibitors of RSK2. Molecular modeling and medicinal chemistry techniques were employed to explore the SAR for this series with a focus of improving in vitro and target modulation potency and physicochemical properties.

  14. Hit to lead SAR study on benzoxazole derivatives for an NPY Y5 antagonist.

    Science.gov (United States)

    Omori, Naoki; Kouyama, Naoki; Yukimasa, Akira; Watanabe, Kana; Yokota, Yasunori; Tanioka, Hideki; Nambu, Hirohide; Yukioka, Hideo; Sato, Norihito; Tanaka, Yukari; Sekiguchi, Kazutaka; Okuno, Takayuki

    2012-03-01

    We report a hit to lead study on a novel benzoxazole NPY Y5 antagonist. Starting from HTS hit 1, structure-activity relationships were developed. Compound 12 showed reduction of food intake and a tendency to suppress body weight gain over the 21-day experimental period.

  15. Room-Temperature Palladium-Catalyzed Direct 2-Arylation of Benzoxazoles with Aryl and Heteroaryl Bromides†

    Science.gov (United States)

    Gao, Feng; Kim, Byeong-Seon; Walsh, Patrick J.

    2014-01-01

    An efficient room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl bromides is presented. The Pd(OAc)2/NiXantphos-based catalyst enables the introduction of various aryl and heteroaryl groups, via a deprotonative cross-coupling process (DCCP) in good to excellent yields (75–99%). PMID:25078988

  16. Synthesis of luminescent 2-(2'-hydroxyphenyl)benzoxazole (HBO) borate complexes.

    Science.gov (United States)

    Massue, Julien; Frath, Denis; Ulrich, Gilles; Retailleau, Pascal; Ziessel, Raymond

    2012-01-01

    Complexation of boron trifluoride by a series of electron donor/acceptor substituted 2-(2'-hydroxy phenyl)benzoxazole (HBO) derivatives yields luminescent B(III) complexes with an emission wavelength ranging from 385 to 425 nm in dichloromethane or toluene. Appropriate chemical functionalization of these new dyes allows connection to different photoactive subunits (Boranil, BODIPY), endowing an efficient cascade energy transfer.

  17. Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents

    Indian Academy of Sciences (India)

    C Praveen; A Nandakumar; P Dheenkumar; D Muralidharan; P T Perumal

    2012-05-01

    Microwave-assisted synthesis of benzothiazole and benzoxazole libraries via PIFA promoted cyclocondensation of 2-aminothiophenols/2-aminophenols with aldehydes under one-pot condition in good to excellent yields was achieved. Twenty compounds have been investigated for their analgesic activity and showed moderate to good activity.

  18. Rotational energy barrier of 2-(2',6'-dihydroxyphenyl)benzoxazole: a case study by NMR.

    Science.gov (United States)

    Chen, Weihua; Twum, Eric B; Li, Linlin; Wright, Brian D; Rinaldi, Peter L; Pang, Yi

    2012-01-01

    2-(2'-Hydroxyphenyl)benzoxazole (HBO) derivatives represent an important class of luminescent materials, as they can undergo excited state intramolecular proton transfer (ESIPT). The material's ESIPT properties are dependent on the ratio of two different rotamers, whose interconversion is poorly understood. By using HBO derivative 4, the rotational energy barrier of 2- (2',6'-hydroxyphenyl)benzoxazole is determined to be 10.5 kcal/mol by variable-temperature NMR. Although a HBO derivative typically exhibits two rotamers with O···H-O (e.g., 1a) and N···H-O bonding (e.g., 1b), correlation of NMR with fluorescence data reveals that the rotamer with N···H-O bonding is predominant in the solution.

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

    Science.gov (United States)

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

    2012-01-10

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

  20. Correlation between the lipophilicity and antifungal activity of some benzoxazole derivatives

    Directory of Open Access Journals (Sweden)

    Podunavac-Kuzmanović Sanja O.

    2010-01-01

    Full Text Available In the present work, a quantitative relationship between the lipophilicity and antifungal activity of some benzoxazole derivatives against Candida albicans was investigated by using QSAR (quantitative structure-activity relationship analyses. The descriptors which describe numerically the lipophilicity, logP, were calculated using Chem-Office Software version 7.0. The linear correlation between the minimal inhibitory concentration (log1/cMIC and lipophilicity descriptors was investigated. The best QSAR model predicting the antifungal activity of the investigated series of benzoxazole was developed. The results are discussed on the basis of statistical data. High agreement between theoretical and experimental inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on antifungal activity of this class of compounds, which can be very useful in the design of new biologically active molecules.

  1. Synthesis and Biological Evaluation of Novel 5,7-Dichloro-1,3-benzoxazole Derivatives

    Directory of Open Access Journals (Sweden)

    N. D. Jayanna

    2013-01-01

    Full Text Available A new class of 5,7-dichloro-1,3-benzoxazole derivatives 4–11 were synthesized by fusing 5,7-dichloro-2-hydrazino-1,3-benzoxazole 3 nucleus with aliphatic acids, active methylene compounds, and with selected esters to form heterocyclic ring systems like 1,2,4-triazoles, pyrazoles, and triazine moieties. The compound 3 on diazotization reaction affords the tetrazole compound. The synthesized compounds were characterized by 1H NMR, IR, Mass, and 13C NMR spectral data and screened for cytotoxic, antimicrobial, antioxidant, and antilipase activities. The compounds 4, 5, and 8 have shown significant antimicrobial activities, whereas compounds 6 and 8 have been emerged as leading cytotoxic agents. The compounds 9, 10, and 11 were found to be strong enzyme inhibitors.

  2. Versatile chemical transformations of benzoxazole based ligands on complexation with 3d-metal ions.

    Science.gov (United States)

    Iasco, Olga; Novitchi, Ghenadie; Jeanneau, Erwann; Tommasino, Jean Bernard; Roques, Nans; Luneau, Dominique

    2012-02-20

    Two benzoxazoles derivative ligands were synthesized from the condensation of 3,5-di-tert-butyl-o-benzoquinone (DTBBQ) with ethanolamine or 1,3-diamino-2-hydroxypropane in methanol. Condensation of DTBBQ with ethanolamine gives the expected 5,7-di-tert-butyl-2-methylenhydroxylbenzoxazole (HL1) while with 1,3-diamino-2-hydroxypropane it gives (2-hydroxyethyl-2-{2,4-bis(1,1-dimethylethyl)-1-phenol-6 amino}-2{5,7-di-tert-butyl-benzoxazole}) (H(2)L2) with only one benzoxazole ring instead of the symmetric bis-benzoxazole derivative. The structure of HL1 and H(2)L2 were confirmed by NMR-spectroscopy and X-ray diffraction on a single crystal for HL1. The reaction of HL1 with CuCl(2) gives a mononuclear [Cu(II)(HL1)(2)Cl(2)] (1) complex for which the crystal structure shows that HL1 is preserved. In contrast, upon reaction with nickel(II), cobalt(II), and manganese(II) H(2)L2 is further oxidized and transformed in new ligands HL3 in mononuclear complexes [M(II)(L3)(2)] (M = Ni(II) (2); M = Co(II) (3)) and H(2)L4 in tetranuclear complex [Mn(II)(4)(HL4)(4)Cl(4)] (4) as found from the crystal structures of complexes 2-4. Electrochemical studies for complexes 2 and 3 evidence complicated redox properties. [Mn(II)(4)(HL4)(4)Cl(4)] (4) has a cubane-like structure with a "4 + 2" fashion The magnetic susceptibility of 4 is well fitted considering one Mn---Mn interaction J(a)(Mn(II)-Mn(II)) = -0.50(1) cm(-1) with g = 2.00(7).

  3. Identification of benzoxazole analogs as novel, S1P(3) sparing S1P(1) agonists.

    Science.gov (United States)

    Deng, Guanghui; Meng, Qinghua; Liu, Qian; Xu, Xuesong; Xu, Qiongfeng; Ren, Feng; Guo, Taylor B; Lu, Hongtao; Xiang, Jia-Ning; Elliott, John D; Lin, Xichen

    2012-06-15

    A novel series of benzoxazole-derived S1P(1) agonists were designed based on scaffold hopping molecular design strategy combined with computational approaches. Extensive SAR studies led to the discovery of compound 17d as a selective S1P(1) agonist (over S1P(3)) with high CNS penetration and favorable DMPK properties. 17d also demonstrated in vivo pharmacological efficacy to reduce blood lymphocyte in mice after oral administration.

  4. 1,1,2,2-Tetrakis(1,3-benzoxazol-2-ylethene

    Directory of Open Access Journals (Sweden)

    Tesfamariam K. Hagos

    2011-08-01

    Full Text Available The title compound, C30H16N4O4, reveals overline1 crystallographic and molecular symmetry and accordingly the asymmetric unit comprises one half-molecule. The dihedral angle between the planes of the two geminal benzoxazole rings is 74.39 (5°. The packing features weak C—H...N and π–π interactions [centroid–centroid distance = 3.652 (1 Å].

  5. 3-Anilinomethyl-5-chloro-1,3-benzoxazol-2(3H-one

    Directory of Open Access Journals (Sweden)

    Orhan Büyükgüngör

    2012-05-01

    Full Text Available In the title compound, C14H11ClN2O2, the 2,3-dihydro-1,3-benzoxazole ring system is essentially planar [maximum deviation = 0.009 (2 Å] and makes a dihedral angle of 79.15 (7° with the phenyl ring. Intermolecular N—H...O and weak C—H...Cl hydrogen bonds occur in the crystal structure.

  6. Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase.

    Science.gov (United States)

    Braun, Stephan; Botzki, Alexander; Salmen, Sunnhild; Textor, Christian; Bernhardt, Günther; Dove, Stefan; Buschauer, Armin

    2011-09-01

    Bacterial hyaluronan lyases (Hyal) degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread. Hyal inhibitors may serve as tools to study the role of the enzyme, its substrates and products in the course of bacterial infections. Moreover, such enzyme inhibitors are potential candidates for antibacterial combination therapy. Based on crystal structures of Streptococcus pneumoniae Hyal in complex with a hexasaccharide substrate and with different inhibitors, 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones were derived as new leads for the inhibition of Streptococcus agalactiae strain 4755 Hyal. Structure-based optimization led to N-(3-phenylpropionyl)benzoxazole-2-thione, one of the most potent compounds known to date (IC(50) values: 24 μM at pH 7.4, 15 μM at pH 5). Among the 27 new derivatives, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5. The results support a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch.

  7. Synthesis and Antimycobacterial and Photosynthesis-Inhibiting Evaluation of 2-[(E-2-Substituted-ethenyl]-1,3-benzoxazoles

    Directory of Open Access Journals (Sweden)

    Ales Imramovsky

    2014-01-01

    Full Text Available A series of twelve 2-[(E-2-substituted-ethenyl]-1,3-benzoxazoles was designed. All the synthesized compounds were tested against three mycobacterial strains. The compounds were also evaluated for their ability to inhibit photosynthetic electron transport (PET in spinach (Spinacia oleracea L. chloroplasts. 2-[(E-2-(4-Methoxyphenylethenyl]-1,3-benzoxazole, 2-[(E-2-(2,3-dihydro-1-benzofuran-5-ylethenyl]-1,3-benzoxazole and 2-{(E-2-[4-(methylsulfanylphenyl]ethenyl}-1,3-benzoxazole showed the highest activity against M. tuberculosis, M. kansasii, and M. avium, and they demonstrated significantly higher activity against M. avium and M. kansasii than isoniazid. The PET-inhibiting activity of the most active ortho-substituted compound 2-[(E-2-(2-methoxyphenylethenyl]-1,3-benzoxazole was IC50 = 76.3 μmol/L, while the PET-inhibiting activity of para-substituted compounds was significantly lower. The site of inhibitory action of tested compounds is situated on the donor side of photosystem II. The structure-activity relationships are discussed.

  8. Synthesis and Antimycobacterial and Photosynthesis-Inhibiting Evaluation of 2-[(E)-2-Substituted-ethenyl]-1,3-benzoxazoles

    Science.gov (United States)

    Imramovsky, Ales; Kozic, Jan; Stolarikova, Jirina; Vinsova, Jarmila

    2014-01-01

    A series of twelve 2-[(E)-2-substituted-ethenyl]-1,3-benzoxazoles was designed. All the synthesized compounds were tested against three mycobacterial strains. The compounds were also evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 2-[(E)-2-(4-Methoxyphenyl)ethenyl]-1,3-benzoxazole, 2-[(E)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1,3-benzoxazole and 2-{(E)-2-[4-(methylsulfanyl)phenyl]ethenyl}-1,3-benzoxazole showed the highest activity against M. tuberculosis, M. kansasii, and M. avium, and they demonstrated significantly higher activity against M. avium and M. kansasii than isoniazid. The PET-inhibiting activity of the most active ortho-substituted compound 2-[(E)-2-(2-methoxyphenyl)ethenyl]-1,3-benzoxazole was IC50 = 76.3 μmol/L, while the PET-inhibiting activity of para-substituted compounds was significantly lower. The site of inhibitory action of tested compounds is situated on the donor side of photosystem II. The structure-activity relationships are discussed. PMID:25197708

  9. 2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation.

    Science.gov (United States)

    Seth, Kapileswar; Garg, Sanjeev K; Kumar, Raj; Purohit, Priyank; Meena, Vachan S; Goyal, Rohit; Banerjee, Uttam C; Chakraborti, Asit K

    2014-05-01

    The 2-(2-arylphenyl)benzoxazole moiety has been found to be a new and selective ligand for the enzyme cyclooxygenase-2 (COX-2). The 2-(2-arylphenyl)benzoxazoles 3a-m have been synthesized by Suzuki reaction of 2-(2-bromophenyl)benzoxazole. Further synthetic manipulation of 3f and 3i led to 3o and 3n, respectively. The compounds 3g, 3n, and 3o selectively inhibited COX-2 with selectivity index of 3n much better than that of the COX-2 selective NSAID celecoxib. The in vivo anti-inflammatory potency of 3g and 3n is comparable to that of celecoxib and the nonselective NSAID diclofenac at two different doses, and 3o showed better potency compared to these clinically used NSAIDs.

  10. Synthesis and biological activity of novel series of 1,3-benzoxazol-2(3H)-one derivatives.

    Science.gov (United States)

    Krawiecka, Mariola; Kuran, Bozena; Kossakowski, Jerzy; Kierzkowska, Marta; Młynarczyk, Grazyna; Cieślak, Marcin; Kaźmierczak-Barańska, Julia; Królewska, Karolina; Dobrowolski, Michał A

    2013-01-01

    In the search for novel biological agents, a series of new derivatives N-substituted 1,3-benzoxazol-2(3H)-one, 5-chloro-1,3-benzoxazol-2(3H)-one, 6-bromo-1,3-benzoxazol-2(3H)-one were prepared. All of the compounds were characterized by 1H NMR, 13C NMR and ESI MS spectra. Moreover, for compound 1 an Xray structure was determined. All derivatives were tested for antimicrobial activity against a selection of Gram-positive, Gram-negative bacteria and yeasts. The selected compounds (2-8, 10) were tested for their cytotoxic properties in K562, HeLa and normal cells.

  11. Mechanistic evidence for a ring-opening pathway in the Pd-catalyzed direct arylation of benzoxazoles

    DEFF Research Database (Denmark)

    Sanchez, R.S.; Zhuravlev, Fedor

    2007-01-01

    The direct Pd-catalyzed arylation of 5-substituted benzoxazoles, used as a mechanistic model for 1,3-azoles, was investigated experimentally and computationally. The results of the primary deuterium kinetic isotope effect, Hammett studies, and H/D exchange were shown to be inconsistent with the r......The direct Pd-catalyzed arylation of 5-substituted benzoxazoles, used as a mechanistic model for 1,3-azoles, was investigated experimentally and computationally. The results of the primary deuterium kinetic isotope effect, Hammett studies, and H/D exchange were shown to be inconsistent...

  12. 2-(4-carbonylphenyl)benzoxazole inhibitors of CETP: scaffold design and advancement in HDLc-raising efficacy.

    Science.gov (United States)

    Sweis, Ramzi F; Hunt, Julianne A; Kallashi, Florida; Hammond, Milton L; Chen, Ying; Eveland, Suzanne S; Guo, Qiu; Hyland, Sheryl A; Milot, Denise P; Cumiskey, Anne-Marie; Latham, Melanie; Rosa, Raymond; Peterson, Larry; Sparrow, Carl P; Wright, Samuel D; Anderson, Matt S; Sinclair, Peter J

    2011-03-15

    The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Initial efforts aimed at engineering replacements for the aniline substructures in the benchmark molecule. Reversing the connectivity of the central aniline lead to a new class of 2-(4-carbonylphenyl)benzoxazoles. Structure-activity studies at the C-7 and terminal pyridine ring allowed for the optimization of potency and HDLc-raising efficacy in this new class of inhibitors. These efforts lead to the discovery of benzoxazole 11v, which raised HDLc by 24 mg/dl in our transgenic mouse PD model.

  13. Structure-activity relationships of 1,3-benzoxazole-4-carbonitriles as novel antifungal agents with potent in vivo efficacy.

    Science.gov (United States)

    Kuroyanagi, Jun-ichi; Kanai, Kazuo; Horiuchi, Takao; Takeshita, Hiroshi; Kobayashi, Shozo; Achiwa, Issei; Yoshida, Kumi; Nakamura, Koichi; Kawakami, Katsuhiro

    2011-01-01

    A series of 1,3-benzoxazole-4-carbonitriles was synthesized and evaluated for its antifungal activity, solubility, and metabolic stability. Among those compounds, 4-cyano-N,N,5-trimethyl-7-[(3S)-3-methyl-3-(methylamino)pyrrolidin-1-yl]-6-phenyl-1,3-benzoxazole-2-carboxamide (16b) exhibited potent in vitro activity against Candida species, higher water solubility, and improved metabolic stability compared to lead compound 1. Compound 16b showed potent in vivo efficacy against mice Candida infection models and good bioavailability in rats.

  14. Synthesis and anti-inflammatory activity of 2-substituted-((N, N-disubstituted)-1, 3-benzoxazole)-5-carboxamides.

    Science.gov (United States)

    Reena, M; Kiran, G; Rajyalakshmi, G; Venkateshwa, Rao J; Sarangapani, M

    2010-06-01

    A series of 2-substituted-((N, N-disubstituted)-1, 3-benzoxazole)-5-carboxamides derivatives were synthesized by the reaction of 2-substituted-5-carbomethoxy benzoxazole with different secondary amines. The newly synthesized compounds were characterized on the basis of spectral (FT-IR, 1H NMR, MS) & elemental analysis. All these compounds were screened for anti-inflammatory activity using carrageenan induced rat paw edema method. All of these compounds exhibited significant activity. Among the tested compounds Ve, Vg, Vf and Va were considered to have potent anti-inflammatory activity and was comparable with standard.

  15. A pilot study of the novel J-PET plastic scintillator with 2-(4-styrylphenyl)benzoxazole as a wavelength shifter

    CERN Document Server

    Wieczorek, A; Niedźwiecki, Sz; Bednarski, T; Białas, P; Czerwiński, E; Danel, A; Gajos, A; Gruntowski, A; Kamińska, D; Kapłon, Ł; Kochanowski, A; Korcyl, G; Kowal, J; Kowalski, P; Kozik, T; Krzemień, W; Kubicz, E; Molenda, M; Pałka, M; Raczyński, L; Rudy, Z; Rundel, O; Salabura, P; Sharma, N G; Silarski, M; Słomski, A; Smyrski, J; Strzelecki, A; Uchacz, T; Wiślicki, W; Zieliński, M; Zoń, N

    2015-01-01

    For the first time a molecule of 2-(4-styrylphenyl)benzoxazole containing benzoxazole and stilbene groups is applied as a scintillator dopant acting as a wavelength shifter. In this article a light yield of the plastic scintillator, prepared from styrene doped with 2 wt% of 2,5-diphenylbenzoxazole and 0.03 wt% of 2-(4-styrylphenyl)benzoxazole, is determined to be as large as 60% $\\pm$ 2% of the anthracene light output. There is a potential to improve this value in the future by the optimization of the additives concentrations.

  16. Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT.

    Science.gov (United States)

    Nahakpam, Lokendrajit; Chipem, Francis A S; Chingakham, Brajakishor S; Laitonjam, Warjeet S

    2016-08-10

    An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism.

  17. Separation of lanthanides and actinides(III) using tridentate benzimidazole, benzoxazole and benzothiazole ligands

    Energy Technology Data Exchange (ETDEWEB)

    Drew, M.G.B.; Hudson, M.J.; Iveson, P.B.; Vaillant, L.; Youngs, T.G.A. [Reading Univ. (United Kingdom). Dept. of Chemistry; Hill, C.; Madic, Ch. [CEA Valrho, Dir. de l' Energie Nucleaire, Departement RadioChimie et Procedes, Service de Chimie des Procedes de Separation (DEN/DRCP/SCPS/LCSE), 30 - Marcoule (France)

    2004-04-01

    The ability of new hydrophobic tridentate ligands based on 2,6-bis(benzimidazole-2-yl)pyridine, 2,6-bis(benzoxazole-2-yl)pyridine and 2,6-bis(benzothiazole-2-yl)pyridine to selectively extract americium(III) from europium(III) was measured. The most promising ligand - 2,6-bis(benzoxazole-2-yl)-4-(2-decyl-1-tetra-decyl-oxy)pyridine L{sup 9} was found to give separation factors (SF{sub Am/Eu}) of up to 70 when used to extract cations from 0.02-0.10 M HNO{sub 3} into TPH in synergy with 2-bromo-decanoic acid. Six structures of lanthanide complexes with 2,6-bis(benzoxazole-2-yl)pyridine L{sup 6} were then determined to evaluate the types of species that are likely to be involved in the separation process. Three structural types were observed, namely [LnL{sup 6}(NO{sub 3}){sub 3}(H{sub 2}O){sub 2}), 11-coordinate only for La, [LnL{sup 6}(NO{sub 3})3 (CH{sub 3}CN)], 10-coordinate for Pr, Nd and Eu and [LnL{sup 6}(NO{sub 3}){sub 3}(H{sub 2}O)], L 10-coordinate for Eu and Gd. Quantum Mechanics calculations were carried out on the tridentate ligands to elucidate the conformational preferences of the ligands in the free state and protonated and di-protonated forms and to assess the electronic properties of the ligands for comparison with other ter-dentate ligands used in lanthanide/actinide separation processes. (authors)

  18. Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5'-monophosphate dehydrogenase.

    Science.gov (United States)

    Gorla, Suresh Kumar; Kavitha, Mandapati; Zhang, Minjia; Chin, James En Wai; Liu, Xiaoping; Striepen, Boris; Makowska-Grzyska, Magdalena; Kim, Youngchang; Joachimiak, Andrzej; Hedstrom, Lizbeth; Cuny, Gregory D

    2013-05-23

    Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5'-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD(+). The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD50 > 50 μM) against a panel of four mammalian cells lines.

  19. 5-tert-Butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl-2-thienyl]-1,3-benzoxazole

    Directory of Open Access Journals (Sweden)

    Fang-Fang Jian

    2008-12-01

    Full Text Available The title compound, C26H26N2O2S, was prepared by the reaction of thiophene-2,5-dicarboxylic acid and 2-amino-4-tert-butylphenol. One of the tert-butyl groups is disordered over two conformations, with occupancies of 0.539 (1 and 0.461 (2. The two 1,3-benzoxazole rings are almost planar, with dihedral angles of 0.83 (18 and 1.64 (17° between the five- and six-membered rings. The thiophene ring makes dihedral angles of 21.54 (19 and 4.49 (18° with the planes of the five-membered oxazole rings. The crystal packing is controlled by π–π stacking interactions involving the thiophene and benzene rings, with a centroid–centroid distance of 3.748 (2 Å.

  20. Synthesis, antimicrobial and cytotoxic activities of pyrimidinyl benzoxazole, benzothiazole and benzimidazole.

    Science.gov (United States)

    Seenaiah, D; Reddy, P Ramachandra; Reddy, G Mallikarjuna; Padmaja, A; Padmavathi, V; Krishna, N Siva

    2014-04-22

    A variety of pyrimidinyl benzoxazoles, benzothiazoles and benzimidazoles linked by thio, methylthio and amino moieties were prepared and studied their antimicrobial and cytotoxic activities. The compound pyrimidinyl bis methylthio benzimidazole 22 was a potent antimicrobial agent particularly against Staphylococcus aureus (29 mm, MIC 12.5 μg/mL) and Penicillium chrysogenum (38 mm, MIC 12.5 μg/mL). The amino linked pyrimidinyl bis benzothiazole 24 exhibited cytotoxic activity on A549 cells with IC50 value of 10.5 μM.

  1. Discovery of 2-substituted benzoxazole carboxamides as 5-HT3 receptor antagonists.

    Science.gov (United States)

    Yang, Zhicai; Fairfax, David J; Maeng, Jun-Ho; Masih, Liaqat; Usyatinsky, Alexander; Hassler, Carla; Isaacson, Soshanna; Fitzpatrick, Kevin; DeOrazio, Russell J; Chen, Jianqing; Harding, James P; Isherwood, Matthew; Dobritsa, Svetlana; Christensen, Kevin L; Wierschke, Jonathan D; Bliss, Brian I; Peterson, Lisa H; Beer, Cathy M; Cioffi, Christopher; Lynch, Michael; Rennells, W Martin; Richards, Justin J; Rust, Timothy; Khmelnitsky, Yuri L; Cohen, Marlene L; Manning, David D

    2010-11-15

    A new class of 2-substituted benzoxazole carboxamides are presented as potent functional 5-HT(3) receptor antagonists. The chemical series possesses nanomolar in vitro activity against human 5-HT(3)A receptors. A chemistry optimization program was conducted and identified 2-aminobenzoxazoles as orally active 5-HT(3) receptor antagonists with good metabolic stability. These novel analogues possess drug-like characteristics and have potential utility for the treatment of diseases attributable to improper 5-HT(3) receptor function, especially diarrhea predominant irritable bowel syndrome (IBS-D).

  2. Synthesis of benzoxazole derivatives of honokiol as insecticidal agents against Mythimna separata Walker.

    Science.gov (United States)

    Yang, Chun; Zhi, Xiaoyan; Xu, Hui

    2015-01-01

    A series of novel benzoxazole compounds derived from a naturally occurring neolignan honokiol were prepared. Their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker) in vivo. Most of the tested derivatives exhibited more potential insecticidal activity than their precursor honokiol at the concentration of 1mg/mL. Especially compound 6e, containing 4-acetyloxyphenyl groups at the C8 and C8' positions, displayed the most potent insecticidal activity with the final mortality rate of 62.1%.

  3. Photophysical properties of 3-[2-(N-phenylcarbazolyl)benzoxazol-5-yl]alanine derivatives--experimental and theoretical studies.

    Science.gov (United States)

    Guzow, Katarzyna; Czerwińska, Marlena; Ceszlak, Agnieszka; Kozarzewska, Marta; Szabelski, Mariusz; Czaplewski, Cezary; Łukaszewicz, Anna; Kubicki, Aleksander A; Wiczk, Wiesław

    2013-02-01

    Solvatochromic probes are often used in biophysical studies to obtain information about polarity of the microenvironment. As there is not much natural fluorophores with such properties, there is still need for new synthetic compounds such as 3-(2-benzoxazol-5-yl)alanine derivatives. Among this group of non-proteinogenic fluorescent amino acids especially interesting are 3-[2-(4-aminophenyl)benzoxazol-5-yl]alanine derivatives whose solvatochromism depends on the substituents on the nitrogen atom, as revealed by our recent studies. To expand them we synthesized two new derivatives with an N-phenylcarbazole moiety in position 2 of the benzoxazole ring and studied their photophysical properties in solvents of different polarity and ability to form hydrogen bonds using absorption and steady-state and time-resolved fluorescence spectroscopy. Applying single parameter and multi-linear correlations with different solvent parameters, the excited state dipole moments were determined as well as the influence of solvent parameters on each photophysical property was estimated. Moreover, the geometry of compounds and vertical absorption transition were theoretically calculated (DFT and TD DFT methods). It was found that the place of substitution of the N-phenylcarbazole part by the benzoxazole unit determines the character of the electron transition (π-π* or ICT) and thereby the spectral and photophysical properties of the compounds studied.

  4. Complex formation of 2-(o-hydroxyphenyl)-benzoxazole and 2-(o-hydroxyphenyl)-benzothiazole with beryllium ions

    Energy Technology Data Exchange (ETDEWEB)

    Gladilovich, D.B.; Stolyarov, K.P. (Leningradskij Gosudarstvennyj Univ. (USSR))

    1984-12-01

    Using spectrophotometric and luminescence methods the interaction of beryllium ions With 2-(0-hydroxyphenyl)-benzoxazole and 2-(0-hydroxyphenyl)-benzothiazole has been studied. The formation of at least three BeL/sup +/, Be(OH)L and BeL/sub 2/ complexes (where L=singly charged anion of ligand) is established.

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

    Science.gov (United States)

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

    2012-02-01

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

  6. Benzoxazole-based heterometallic dodecanuclear complex [Dy(III)4Cu(II)8] with single-molecule-magnet behavior.

    Science.gov (United States)

    Iasco, Olga; Novitchi, Ghenadie; Jeanneau, Erwann; Wernsdorfer, Wolfgang; Luneau, Dominique

    2011-08-15

    Three Cu-Ln (Ln = Dy, Gd, Y) dodecanuclear clusters assembled by a novel ligand of the benzoxazole type are reported. The dysprosium cluster exhibits a frequency dependence of the alternating-current susceptibility and hysteresis loop at low temperature, indicating single-molecule-magnet behavior.

  7. One-pot sequential alkynylation and cycloaddition: regioselective construction and biological evaluation of novel benzoxazole-triazole derivatives.

    Science.gov (United States)

    Srivastava, Ananya; Aggarwal, Leena; Jain, Nidhi

    2015-01-12

    Individually, benzoxazole and triazole moieties are of significant biological interest owing to their importance in drugs and pharmaceuticals. To assess their combined biological impact when woven into one molecule, we designed a novel, regioselective, multicomponent, one-pot (MCOP) approach for the construction of benzoxazole-linked triazoles. The synthesis has been achieved in two sequential steps involving copper-catalyzed alkynylation of benzoxazole followed by a 1,3-dipolar cycloaddition reaction. By combination of these two bioactive units into one core, a series of new benzoxazole-triazole scaffolds has been synthesized and subjected to in vitro antibacterial and anticancer evaluation. Tests against clinical isolates of Staphylococcus aureus and Escherichia coli showed potent Gram-negative activity for compounds 4{1,1,1}, 4{1,1,4}, and 4{1,2,1}. The cytotoxicity of the synthesized library was determined against three cancer cell lines: HeLa, SKBr3, and Hep G2. Compound 4{2,2,2} showed significant cytotoxicity against all the cell lines. These preliminary bioassay evaluations strongly suggest the promise and scope of these novel molecules as therapeutic agents in medical science.

  8. An efficient Biginelli one-pot synthesis of new benzoxazole-substituted dihydropyrimidinones and thiones catalysed by trifluoro acetic acid under solvent-free conditions

    Institute of Scientific and Technical Information of China (English)

    D.Shobha; M.Adharvana Chari; K.H.Ahn

    2009-01-01

    An efficient synthesis of benzoxazole-substituted 3,4-dihydropyrimidinones(DHPMs)using trifluoro acetic acid as the catalyst for the first time from an aldehyde,β-keto ester and benzoxazole-substituted urea/thiourea under solvent-free conditions is described.Compared to the classical Biginelli reaction conditions,this new method consistently has the advantage of excellent yields(80-91%)and short reaction time(40-130 min)at reflux temperature.

  9. Improvement of surface wetting properties of poly(p-phenylene benzoxazole) by incorporation of ionic groups

    Energy Technology Data Exchange (ETDEWEB)

    Luo Kaiqing [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 200051 (China); Jin Junhong [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 200051 (China); Yang Shenglin [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 200051 (China); Li Guang [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 200051 (China)]. E-mail: lig@dhu.edu.cn; Jiang Jianming [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 200051 (China)

    2006-07-25

    Modified poly(p-phenylene benzoxazole), SPBO, containing ionic sulfonate groups was synthesized by polycondensation of the corresponding monomers in polyphosphoric acid. SPBO fiber was spun via a dry-jet wet-spinning technique. The wetting property of poly(p-phenylene benzoxazole) (PBO) fiber and SPBO fiber were measured by contact angle analysis, and the interfacial shear strength (IFSS) between fibers and epoxy was determined by microbond pull-out testing. The contact angles of water and ethanol on SPBO fiber surface get smaller, and the wetting process becomes faster. The surface free energy of SPBO fiber increases to 38.9 mJ m{sup -2}, which is 9.6% higher than that of PBO fiber. Furthermore the ionic introducing leads to a 23% increase in IFSS from 8.2 MPa for PBO/epoxy to 10.1 MPa for SPBO/epoxy. It could be expected that the failure mode may change from fiber/matrix interface adhesive failure to partly cohesive failure mode.

  10. A fluorescent bis(benzoxazole) ligand: toward binuclear Zn(II)-Zn(II) assembly.

    Science.gov (United States)

    Chu, Qinghui; Medvetz, Doug A; Panzner, Matthew J; Pang, Yi

    2010-06-14

    A bis(benzoxazole) ligand (HL) has been synthesized, and its reaction with Zn(OAc)(2) has led to fluorescent complexes via formation of binuclear Zn(II)-Zn(II) cores. The ligand-to-metal ratio of the complexes varies from 1 : 1 to 2 : 1, depending on the reaction conditions. A large binding constant K = 8.3 x 10(20) [M(-3)] has been determined for the reaction L + Zn(2+)-->L(2):Zn(2)(2+). The result indicates that the bis(benzoxazole) ligand is a useful building block to construct a binuclear core. On the basis of X-ray analysis, the binuclear Zn(II)-Zn(II) distance in the complexes is determined to be approximately 3.22 A, which is quite comparable to that found in the enzymes (3.3 A). Absorption and fluorescence study shows that a subtle chemical environmental change within the binuclear core can induce a large optical response.

  11. Synthesis, anti-breast cancer activity, and molecular modeling of some benzothiazole and benzoxazole derivatives.

    Science.gov (United States)

    Abdelgawad, Mohamed A; Belal, Amany; Omar, Hany A; Hegazy, Lamees; Rateb, Mostafa E

    2013-07-01

    A new series of benzothiazoles and benzoxazoles was synthesized using 4-benzothiazol-2-yl-phenylamine and 4-benzoxazol-2-yl-phenylamine as starting materials. All the prepared compounds were evaluated for their antitumor activities against human breast cancer cell lines, MCF-7 and MDA-231, using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) cell viability analysis. Almost all the tested compounds revealed potent antitumor activity, especially the N-methyl piperazinyl substituted derivatives 6f and 6c, which displayed the most potent inhibitory activity with IC50 values ranging from 8 to 17 nM. Docking the synthesized compounds into the epidermal growth factor receptor (EGFR), which is highly expressed in breast cancer, was employed to explore the possible interactions of these compounds with the EGFR. The activity of the reported compounds supports its clinical promise as a component of therapeutic strategies for cancer, for which high concentrations of chemotherapeutic agents are always a major limitation.

  12. Characterization of the Biosynthetic Gene Cluster for Benzoxazole Antibiotics A33853 Reveals Unusual Assembly Logic.

    Science.gov (United States)

    Lv, Meinan; Zhao, Junfeng; Deng, Zixin; Yu, Yi

    2015-10-22

    A33853, which shows excellent bioactivity against Leishmania, is a benzoxazole-family compound formed from two moieties of 3-hydroxyanthranilic acid and one 3-hydroxypicolinic acid. In this study, we have identified the gene cluster responsible for the biosynthesis of A33853 in Streptomyces sp. NRRL12068 through genome mining and heterologous expression. Bioinformatics analysis and functional characterization of the orfs contained in the gene cluster revealed that the biosynthesis of A33853 is directed by a group of unusual enzymes. In particular, BomK, annotated as a ketosynthase, was found to catalyze the amide bond formation between 3-hydroxypicolinic and 3-hydroxyanthranilic acid during the assembly of A33853. BomJ, a putative ATP-dependent coenzyme A ligase, and BomN, a putative amidohydrolase, were further proposed to be involved in the benzoxazole formation in A33853 according to gene deletion experiments. Finally, we have successfully utilized mutasynthesis to generate two analogs of A33853, which were reported previously to possess excellent anti-leishmanial activity.

  13. Fluorescence characteristics and photostability of benzoxazole derived donor-acceptor dyes in constrained media.

    Science.gov (United States)

    Fayed, Tarek A; Etaiw, Safaa El-Din H

    2006-10-01

    The spectroscopic properties and photoreactivity of 2-(4-dimethylaminostryl)benzoxazole and its butadienyl analogue (abbreviated as DMASBO and BODB, respectively) were investigated in thin films of PS, PMMA and PVA polymer matrices as well as immobilized on silica surface. The experimental results showed that the investigated benzoxazole derivatives are sensitive to the polarity of its microenvironment even in the glassy matrices and in the solid state. The micropolarity of PVA and silica surface is greater than that of PMMA and PS. The combined results of fluorescence quantum yield and photoisomerization indicated that the size of the free volume within the polymer matrix influence strongly the photochemical reactivity of the used dyes. In PVA, which offers the smaller free volume, the photoreaction is totally blocked while the fluorescence yield is extremely enhanced relative to those in solutions and other polymer matrices. This is associated with an emission of green laser from DMASBO-PVA doped film when pumped by nitrogen laser (337 nm). The results showed that the present dyes are excellent probes for non-fluorescent systems presenting constrained geometry. The spectra of amorphous solid thin films of both dyes were also measured and show large red shifts relative to those in solutions indicating symmetric aggregation of molecules in the solid crystals.

  14. Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.

    Science.gov (United States)

    Xiong, Li; Zhu, Xiao-Lei; Shen, Yan-Qing; Wishwajith, Wickramabahu Kandergama Wasala Mudiyanselage; Li, Kui; Yang, Guang-Fu

    2015-05-05

    Succinate-ubiquinone oxidoreductase (SQR, EC 1.3.5.1, complex II), an essential component of cellular respiratory chain and tricarboxylic acid (or Krebs) cycle, has been identified as one of the most significant targets for pharmaceutical and agrochemical. Herein, with the aim of discovery of new antibacterial lead structure, a series of N-benzoxazol-5-yl-pyrazole-4-carboxamides were designed, synthesized, and evaluated for their SQR inhibitory effects. Very promisingly, one candidate (Ki = 11 nM, porcine SQR) was successfully identified as the most potent synthetic SQR inhibitor so far. The further inhibitory kinetics studies revealed that the candidate is non-competitive with respect to the substrate cytochrome c and DCIP. Computational simulations revealed that the titled compounds have formed hydrogen bond with D_Y91 and B_W173 and the pyrazole ring formed cation-π interaction with C_R46. In addition, in R(1) position, -CHF2 group has increased the binding affinity and decreased the entropy contribution, while -CF3 group displayed completely opposite effect when bound with SQR. The results of the present work showed that N-benzoxazol-5-yl-pyrazole-4-carboxamide is a new scaffold for discovery of SQR inhibitors and worth further study.

  15. Synthesis, metal ion binding, and biological evaluation of new anticancer 2-(2'-hydroxyphenyl)benzoxazole analogs of UK-1.

    Science.gov (United States)

    McKee, Mireya L; Kerwin, Sean M

    2008-02-15

    UK-1 is a bis(benzoxazole) natural product displaying activity against a wide range of human cancer cell lines. A simplified analog of UK-1, 4-carbomethoxy-2-(2'-hydroxyphenyl)benzoxazole, was previously found to be almost as active as UK-1 against cancer cell lines, and similar to the natural product, formed complexes with a variety of metal ions such as Mg2+ and Zn2+. A series of 4-substituted-2-(2'-hydroxyphenyl)benzoxazole analogs of this 'minimal pharmacophore' of UK-1 were prepared. The anti-cancer activity of these analogs was examined in breast and lung cancer cell lines. Spectrophotometric titrations in methanol were carried out in order to assess the ability of UK-1 and these analogs to coordinate with Mg2+ and Cu2+ ions. Although none of the new analogs were more cytotoxic than 4-carbomethoxy-2-(2'-hydroxyphenyl)benzoxazole, some analogs were identified that display similar cytotoxicity to this simplified UK-1 analog with improved water solubility. UK-1 and all of these new analogs bind Cu2+ ions better than Mg2+ ions, and the nature of the 4-substituent is important for the Mg2+ ion binding ability of these 2-(2'-hydroxyphenyl)benzoxazoles. Previous studies of a limited number of UK-1 analogs demonstrated a correlation between Mg2+ ion binding ability and cytotoxicity; however, within this series of 4-substituted-2-(2'-hydroxyphenyl)benzoxazoles the variations in cytotoxicity do not correlate with either Mg2+ or Cu2+ ion binding ability. These results, together with recent ESI-MS studies of Cu2+-mediated DNA binding by UK-1 and analogs, indicate that UK-1 and analogs may exert their cytotoxic effects by interaction with Cu2+ or other transition metal ions, rather than Mg2+, and that metal ion-mediated DNA binding, rather than metal ion binding affinity, is important for the cytotoxic effect of these compounds. The potential role of Cu2+ ions in the cytotoxic action of UK-1 is further supported by the observation that UK-1 in the presence of Cu2

  16. Expeditious and Efficient Synthesis of Benzoxazoles, Benzothiazoles, Benzimidazoles Catalyzed by Ga(OTf)3 under Solvent-Free Conditions%Expeditious and Efficient Synthesis of Benzoxazoles, Benzothiazoles, Benzimidazoles Catalyzed by Ga(OTf)3 under Solvent-Free Conditions

    Institute of Scientific and Technical Information of China (English)

    刘巨艳; 刘倩; 徐玮; 王玮璐

    2011-01-01

    A new and efficient method for the synthesis of benzoxazoles, benzothiazoles, benzimidazoles from reactions of o-substituted aminoaromatics with orthoesters in the presence of catalytic amounts of Ga(OTf)3 under solvent-free conditions is presented. The remarkable features of this new protocol are high conversion, very short reaction times, cleaner reaction profiles under solvent-free conditions, straight forward procedure, and use of relatively non-toxic catalysts.

  17. Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives

    Directory of Open Access Journals (Sweden)

    Vikas S. Padalkar

    2016-11-01

    Full Text Available In an endeavor to find a new class of antimicrobial agents, a series of 2-(1H-benzimidazol-2-yl-5-(diethylaminophenol, 2-(1,3-benzoxazol-2-yl-5-(diethylaminophenol, 2-(1,3-benzothiazol-2-yl-5-(diethylaminophenol and their derivatives were synthesized starting from p-N,N-diethyl amino salicylaldehyde with different substituted o-phenylenediamine or o-aminophenol or o-aminothiophenol. The newly synthesized compounds were characterized by FT-IR, 1H NMR and LC–MS analysis. All compounds were evaluated for in vitro antibacterial activities against Escherichia coli and Staphylococcus aureus strains and in vitro antifungal activity against Candida albicans and Aspergillus niger strains by using serial dilution method. The antibacterial activities were expressed as the minimum inhibitory concentration (MIC in μg/mL.

  18. Multistep divergent synthesis of benzimidazole linked benzoxazole/benzothiazole via copper catalyzed domino annulation.

    Science.gov (United States)

    Liao, Jen-Yu; Selvaraju, Manikandan; Chen, Chih-Hau; Sun, Chung-Ming

    2013-04-21

    An efficient, facile synthesis of structurally diverse benzimidazole integrated benzoxazole and benzothiazoles has been developed. In a multi-step synthetic sequence, 4-fluoro-3-nitrobenzoic acid was converted into benzimidazole bis-heterocycles, via the intermediacy of benzimidazole linked ortho-chloro amines. The amphiphilic reactivity of this intermediate was designed to achieve the title compounds by the reaction of various acid chlorides and isothiocyanates in a single step through the in situ formation of ortho-chloro anilides and thioureas under microwave irradiation. A versatile one pot domino annulation reaction was developed to involve the reaction of benzimidazole linked ortho-chloro amines with acid chlorides and isothiocyanates. The initial acylation and urea formation followed by copper catalyzed intramolecular C-O and C-S cross coupling reactions furnished the angularly oriented bis-heterocycles which bear a close resemblance to the streptomyces antibiotic UK-1.

  19. Design and synthesis of novel benzoxazole analogs as Aurora B kinase inhibitors.

    Science.gov (United States)

    An, Ying; Lee, Eun; Yu, Yeongji; Yun, Jieun; Lee, Myeong Youl; Kang, Jong Soon; Kim, Woo-Young; Jeon, Raok

    2016-07-01

    A novel series of benzoxazole analogs was designed and synthesized, and their inhibitory activities against Aurora kinases were evaluated. Some of the tested compounds exhibited a promising activity with respect to the inhibition of Aurora B kinase. A structure-activity relationship study indicated that linker length, regiochemistry, and halogen substitution play important roles in kinase inhibitory potency. The binding modes between representative compounds and Aurora kinases were interpreted through a molecular docking study to explain the inhibitory activity and selectivity for Aurora A and B kinases. Compounds 13l and 13q also show an antiproliferative effect on the human tumor cell lines in a dose-dependent manner. The most potent 13q demonstrated good efficacy in the prostate cancer PC-3 tumor xenograft model.

  20. Synthesis and blue electroluminescent properties of zinc (II) [2-(2-hydroxyphenyl)benzoxazole

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Won Sam [Department of Chemistry and BPRC, Inje University, Gimhae 621-749 (Korea, Republic of); You, Jung Min [Department of Chemistry and BPRC, Inje University, Gimhae 621-749 (Korea, Republic of); Lee, Burm-Jong [Department of Chemistry and BPRC, Inje University, Gimhae 621-749 (Korea, Republic of)]. E-mail: chemlbj@inje.ac.kr; Jang, Yoon-Ki [Department of Electrical Engineering, Dong-A University, Busan 604-714 (Korea, Republic of); Kim, Dong-Eun [Department of Electrical Engineering, Dong-A University, Busan 604-714 (Korea, Republic of); Kwon, Young-Soo [Department of Electrical Engineering, Dong-A University, Busan 604-714 (Korea, Republic of)

    2007-04-23

    This study reports on the properties of organic light-emitting diodes (OLEDs) with zinc (II) [2-(2-hydroxyphenyl)benzoxazole] as a hole-blocking layer. OLEDs devices are prepared in a conventional OLEDs structure (i.e., anode/HTL/EL/HBL/cathode and anode/HTL/HBL/EL/cathode). The luminescence efficiencies and the turn-on voltage are significantly affected by the existence of the hole-blocking layer. This is attributed to an excellent hole-blocking property, which is in turn due to the high HOMO energy level (6.5 eV). The device showed luminous efficiency 2.46 lm/W at 5 V. The maximum luminance of about 10,000 cd/m{sup 2} is obtained, and the turn-on voltage (2.5 V) is affected by the existence of the hole-blocking layer.

  1. Molecular design, synthesis and cell based HCV replicon assay of novel benzoxazole derivatives.

    Science.gov (United States)

    Ismail, M A H; Adel, M; Ismail, N S M; Abouzid, K A M

    2013-03-01

    Hepatitis C virus inhibitors based on benzoxazole scaffold were designed based on molecular modeling simulation study including docking into the NS5B polymerase active site. Several compounds showed significant high simulation docking scores relative to the assigned benzimidazole lead compound. The designed compounds were synthesized, structurally elucidated and their antiviral activity was evaluated through cell-based replicon in cultured Huh 5-2 cells. A number of the synthesized compounds showed significant inhibitory activity ranging from (52.2% inhibition up to 98% at<50 µg/mL). N-Benzyl-2-phenylbenzo[1,3]oxazole-5-carboxamide (8b) and N-Phenethyl-2-phenylbenzo[1,3] oxazole-5-carboxamide (8c) demonstrated genuine HCV inhibitory activity with EC50 values of 41.6 and 24.5 µg/mL respectively.

  2. Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors.

    Science.gov (United States)

    Jonckers, Tim H M; Rouan, Marie-Claude; Haché, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C

    2012-08-01

    A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl)amino)-N-isobutylbenzo[d]oxazole-6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent 'boosting' properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers.

  3. 2-(2{prime}-hydroxyphenyl)benzothiazoles, -benzoxazoles, and -benzimidazoles for plastic scintillation applications

    Energy Technology Data Exchange (ETDEWEB)

    Pla-Dalmau, A. [Fermi National Accelerator Lab., Batavia, IL (United States)

    1995-08-25

    A new series of fluorescent compounds has been tested as dopants for plastic scintillation applications. Several 2-(2{prime}-hydroxyphenyl)benzothiazole, -benzoxazole, and -benzimidazole derivatives have been prepared and studied in a polystyrene matrix. Each derivative has been added to a styrene solution which has been thermally polymerized. The transmittance, fluorescence, and light yield characteristics of these compounds in polystyrene have been determined. Their emission time distributions have also been measured, and the decay time constants have been calculated from these data. In addition, the doped polystyrene samples have been irradiated to a total dose of 10 Mrad, utilizing a {sup 60}Co source in order to evaluate their susceptibility to radiation-induced damage. 6 figs., 1 tab.

  4. Synthesis and pharmacological evaluation of piperidine (piperazine)-substituted benzoxazole derivatives as multi-target antipsychotics.

    Science.gov (United States)

    Huang, Ling; Zhang, Wenjun; Zhang, Xiaohua; Yin, Lei; Chen, Bangyin; Song, Jinchun

    2015-11-15

    The present study describes the optimization of a series of novel benzoxazole-piperidine (piperazine) derivatives combining high dopamine D2 and serotonin 5-HT1A, 5-HT2A receptor affinities. Of these derivatives, the pharmacological features of compound 29 exhibited high affinities for the DA D2, 5-HT1A and 5-HT2A receptors, but low affinities for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. Furthermore, compound 29 reduced apomorphine-induced climbing and 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI)-induced head twitching without observable catalepsy, even at the highest dose tested. Thus, compound 29 is a promising candidate as a multi-target antipsychotic treatment.

  5. Synthesis, photo-physical and DFT studies of ESIPT inspired novel 2-(2',4'-dihydroxyphenyl) benzimidazole, benzoxazole and benzothiazole.

    Science.gov (United States)

    Patil, Vikas S; Padalkar, Vikas S; Tathe, Abhinav B; Gupta, Vinod D; Sekar, N

    2013-09-01

    Novel ESIPT inspired benzimidazole, benzoxazole and benzothiazole were synthesized from 2,4-dihydroxy benzoic acid and 1,2-phenelenediamine, 2-aminophenol, and 2-aminothiophenol respectively. The synthesized 2-(2',4'-dihydroxyphenyl) benzimidazole, benzoxazole and benzothiazole are fluorescent and the emission characteristic are very sensitive to the micro-environment. They show a single absorption and dual emission with large Stokes shift originating from excited state intramolecular proton transfer. The absorption-emission characteristics of all these compounds are studied as a function of pH. The change in the electronic transition, energy levels, and orbital diagrams of synthesized compounds were investigated by the molecular orbital calculation and were correlated with the experimental spectral emission. Experimental absorption and emission wavelengths are in good agreement with those predicted using the Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT) [B3LYP/6-31G(d)].

  6. Excited state intramolecular proton transfer and charge transfer dynamics of a 2-(2'-hydroxyphenyl)benzoxazole derivative in solution.

    Science.gov (United States)

    Kim, Chul Hoon; Park, Jaehun; Seo, Jangwon; Park, Soo Young; Joo, Taiha

    2010-05-13

    Excited state intramolecular proton transfer (ESIPT) and subsequent intramolecular charge transfer (ICT) dynamics of a 2-(2'-hydroxyphenyl)benzoxazole derivative conjugated with an electron withdrawing group (HBOCE) in solutions and a polymer film has been investigated by femtosecond time-resolved fluorescence (TRF) and TRF spectra measurements without the conventional spectral reconstruction method. TRF with high enough resolution (benzoxazole groups is invoked to account for the dispersive ESIPT dynamics in liquids. From the TRF spectra of both the enol and keto isomers, we have identified the ICT reaction of the keto isomer occurring subsequent to the ESIPT. The ICT proceeds also by two time constants of near instantaneous and 2.7 ps. Since the ICT dynamics of HBOCE is rather close to the polar solvation dynamics, we argue that the ICT is barrierless and determined mostly by the solvent fluctuation.

  7. 2-(Nitroaryl)benzothiazole and benzoxazole derivatives as fluorogenic substrates for the detection of nitroreductase activity in clinically important microorganisms.

    Science.gov (United States)

    Cellier, Marie; Gignoux, Amandine; James, Arthur L; Orenga, Sylvain; Perry, John D; Robinson, Shaun N; Stanforth, Stephen P; Turnbull, Graeme

    2015-12-15

    A series of carboxy-substituted 2-(nitroaryl)benzothiazole derivatives and carboxy-substituted 2-(nitroaryl)benzoxazole derivatives were prepared and evaluated as potential nitroreductase substrates for the purpose of detecting clinically important microorganisms. Several of the substrates produced highly fluorescent colonies with the majority of a panel of 10 Gram-negative bacteria and also with two of a panel of 8 Gram-positive bacteria.

  8. The Synthesis and Evaluation of Third-Order Optical Nonlinearities of Model Compounds Containing Benzothiazole, Benzimidazole and Benzoxazole Moieties.

    Science.gov (United States)

    1991-02-01

    AD-A235 622 WL-TR-91-4015 THE SYNTHESIS AND EVALUATION OF THIRD-ORDER OPTICAL NONLINEARITIES OF MODEL COMPOUNDS CONTAINING BENZOTHIAZOLE ...Nonlinearities of Model Compounds Containing Benzothiazole , Benzimidazole, and Benzoxazole Moieties 12 PERSONAL AUTHOR(S) Bruce A. Reinhardt, Marilyn R...necessary and identify by block number) FIELD GROUP SUB-GROUP nonlinear optical properties benzothiazole u/ 03 degenerate four-wave mixing benzimidazole 21

  9. NaHSO4-SiO2-Promoted Solvent-Free Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazole Derivatives

    Directory of Open Access Journals (Sweden)

    K. Ravi Kumar

    2013-01-01

    Full Text Available An efficient protocol has been developed for the preparation of a library of benzoxazole, benzimidazole, and benzothiazole derivatives from reactions of acyl chlorides with o-substituted aminoaromatics in the presence of catalytic amount of silica-supported sodium hydrogen sulphate under solvent-free conditions. Simple workup procedure, high yield, easy availability, reusability, and use of ecofriendly catalyst are some of the striking features of the present protocol.

  10. Draft Genome Sequence of Marine Actinomycete Streptomyces sp. Strain NTK 937, Producer of the Benzoxazole Antibiotic Caboxamycin.

    Science.gov (United States)

    Olano, Carlos; Cano-Prieto, Carolina; Losada, Armando A; Bull, Alan T; Goodfellow, Michael; Fiedler, Hans-Peter; Méndez, Carmen; Salas, José A

    2014-07-03

    Streptomyces sp. strain NTK 937 is the producer of the benzoxazole antibiotic caboxamycin, which has been shown to exert inhibitory activity against Gram-positive bacteria, cytotoxic activity against several human tumor cell lines, and inhibition of the enzyme phosphodiesterase. In this genome announcement, we present a draft genome sequence of Streptomyces sp. NTK 937 in which we identified at least 35 putative secondary metabolite biosynthetic gene clusters.

  11. Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives.

    Science.gov (United States)

    Satyendra, R V; Vishnumurthy, K A; Vagdevi, H M; Rajesh, K P; Manjunatha, H; Shruthi, A

    2011-07-01

    A novel 6,8-dichloro [1,2,4]triazolo [3,4-b] [1,3]benzoxazole-3(2H)-thione 4 and its derivatives 5a and 5b are synthesized from 5,7-dichloro-2-hydrazinyl-1,3-benzoxazole 3, obtained by reaction of hydrazine hydrate with ethyl [(5,7-dichloro-1,3-benzoxazol-2-yl)sulfanyl]acetate 2. The newly synthesized compounds are characterized by analytical (1)H NMR, (13)C NMR, LC-MS mass spectrometry and elemental analysis. All synthesized compounds are screened for in vitro antioxidant and anthelmintic activities. In correlation to anthelmintic activity, compounds are subjected to molecular docking studies for the binding to β-Tubulin, target protein elite to the parasites. Compounds 3, 4 and 5a exhibited potential radical scavenging capacity with good anthelmintic activity. In molecular docking study also, compounds showed minimum binding energy and have good affinity toward the active pocket thus, they may be considered as good inhibitor of β-Tubulin.

  12. Polymer supported synthesis of novel benzoxazole linked benzimidazoles under microwave conditions: in vitro evaluation of VEGFR-3 kinase inhibition activity.

    Science.gov (United States)

    Chanda, Kaushik; Maiti, Barnali; Yellol, Gorakh S; Chien, Ming-Hsien; Kuo, Min-Liang; Sun, Chung-Ming

    2011-03-21

    An efficient soluble polymer-supported method has been developed for the parallel synthesis of substituted benzimidazole linked benzoxazoles using focused microwave irradiation. The key step involves the amidation of 4-hydroxy-3-nitrobenzoic acid with polymer-immobilized o-phenylenediamine. Application of mild acidic conditions promoted the ring closure to furnish the benzimidazole ring. After hydrogenation of the nitro-group to amine, the resulted polymer conjugates underwent efficient ring closure with various alkyl, aryl and heteroaryl isothiocyanates to generate the polymer-bound benzimidazolyl benzoxazoles. The polymer-bound compounds were finally cleaved from the support to furnish benzimidazole linked benzoxazole derivatives. The efficacy of the resultant angular bis-heterocyclic library was studied against vascular endothelial growth factor receptor (VEGFR-3). The preliminary screening of these novel compounds exhibits moderate to high inhibition (IC(50) = 0.56-1.42 μM). This protocol provides an easy access to novel angular bis-heterocycles which have potential for the discovery of novel leads for targeted cancer therapeutics.

  13. Synthesis and optical properties of poly[(4-(benzoxazole-2-yl)phenyl)methyl methacrylate] with 1,8-naphthalimide end group

    Institute of Scientific and Technical Information of China (English)

    JIN ZhengNeng; XU OingFeng; LU JianMei; YAN Feng; XIA XueWei; WANG LiHua; LI NaJun

    2009-01-01

    A series of homopolymers,poly[(4-(benzoxazole-2-yl)phenyl)methyl methacrylate] (NAPH-PMABEs) containing benzoxazole side chain and 1,8-naphthalimide end group,were prepared by atom transfer radical polymerization (ATRP) and end-group modification.The structure of NAPH-PMABE was char-acterized by GPC,1H-NMR and UV-vis spectra.The polymer has good solubility in common organic solvents,such as dichloromethane (CH2Cl2),tetrahydrofuran (THF),N,N-dimethylformamide (DMF),chloroform (CHCl3),acetone and toluene.The optical properties of NAPH-PMABE were investigated.Results show that NAPH-PMABE has a composite emission spectrum comprising an ultraviolet com-ponent originating from benzoxazole side chains and a green component originating from 1,8-naphthalimide end group in both solution and film.The intensity of the two emission bands can be easily tuned by changing molecular weight.

  14. The Structure of Poly-2,5-Benzoxazole (ABPBO) and Poly-2,6-Benzothiazole (ABPBT) Fibers By X-Ray Diffraction

    Science.gov (United States)

    1985-07-01

    AFWAL-TR-85-4097 ADA \\bC \\ Uq THE STRUCTURE OF POLY-2,5-BENZOXAZOLE (ABPBO) AND POLY-2,6-BENZOTHIAZOLE (ABPBT) FIBERS BY X-RAY DIFFRACTION Albert V...Classification) THE STRUCTURE OF POLY-2,5-BENZOXAZOLE (ABPBO) AND POLY-2,6-BENZOTHIAZOLE (ABPBT) FIBERS BY X-RAY DIFFRACTION 12. PERSONAL AUTHOR(S) W. Wade Adams...and identify by block number) FIELD GROUP SUB-GROUP Polybenzoxazole Unit Cell ABPBO Aromatic Heterocyclic 07 04 Polymer 11 04 19. ABSTRACT (Continue

  15. Synthesis, structures and electrochemical and photophysical properties of anilido-benzoxazole boron difluoride (ABB) complexes.

    Science.gov (United States)

    Meesala, Yedukondalu; Kavala, Veerababurao; Chang, Hao-Ching; Kuo, Ting-Shen; Yao, Ching-Fa; Lee, Way-Zen

    2015-01-21

    A new series of four-ring-fused π-conjugated anilido-benzoxazole boron difluoride (ABB) dyes were synthesized by employing an unsymmetrical bidentate ligand under a mild reaction condition. X-ray structural analysis demonstrated that the four-ring-fused π-conjugated skeleton is nearly coplanar, and almost orthogonal to the side anilido phenyl group with dihedral angles of 74-86°. The synthesized complexes exhibit very bright luminescence in solution (Φf = 0.45-0.96 in CH2Cl2) and in the solid-state (Φf = 0.07-0.37). These complexes show a larger Stokes shift (56-128 nm) than the well-known boron dipyrromethene dyes (8-12 nm, in most cases). The role of molecular packing patterns elucidated by the assistance of their X-ray crystal structures rationalizes the solid-state fluorescence. One of the tested compounds displayed aggregation induced emission (AIE). First-principle-based quantum-chemical studies were carried out on complexes . Time-dependent DFT (TD-DFT) calculations support the experimental results. The participation of the anilido phenyl moiety and the fluorine atoms was found to be negligible in the LUMO orbitals.

  16. Facile formation and redox of benzoxazole-2-thiolate-bridged dinuclear Pt(II/III) complexes.

    Science.gov (United States)

    Wang, Zhe; Jiang, Lu; Liu, Zhi-Pan; Gan, C R Raymond; Liu, Zhaolin; Zhang, Xin-Hai; Zhao, Jin; Hor, T S Andy

    2012-10-28

    Reaction of [Pt(L)(μ-Cl)](2) (L = ppy (2-phenylpyridine) or bzq (benzo[h]quinoline)) with 2-mercaptobenzoxazole (NOSH) and NaOAc in THF at r.t. yields the dinuclear Pt(II) d(8)-d(8) complexes [Pt(2)L(2)(μ-NOS-κN,S)(2)] (L = ppy, 1; L = bzq, 2) and the Pt(III) d(7)-d(7) complexes [Pt(2)(ppy)(2)(μ-NOS-κN,S)(2)(NOS-κS)(2)] (L = ppy, 3; L = bzq, 4) in one pot. The C,N-cyclometalated ligand is chelating whereas the N,S-donating benzoxazole-2-thiolates doubly bridge the two metal centers. The Pt···Pt separations of 3.0204(3) and 2.9726(8) Å in 1 and 2 contract to 2.685(1) Å in 3 and 2.6923(3) Å in 4, respectively, when two S-bound thiolate ligands coordinate trans- to the Pt···Pt axis. However, cyclometalation is preserved and there is minimum perturbation of the bridging ligands. Complexes 3 and 4 can be also obtained by oxidative addition of the thiolate ligand. In the presence of NaBH(4), 3 and 4 can be reduced to 1 and 2, respectively. At r.t., 1 and 2 exhibit intense orange-red luminescence at 625 nm and 631 nm, respectively. The electrochemical properties of 1-4 have been also discussed.

  17. Absorption and Emission Sensitivity of 2-(2'-Hydroxyphenyl)benzoxazole to Solvents and Impurities.

    Science.gov (United States)

    Yuan, Zhao; Tang, Qing; Sreenath, Kesavapillai; Simmons, J Tyler; Younes, Ali H; Jiang, De-En; Zhu, Lei

    2015-01-01

    2-(2'-Hydroxyphenyl)benzoxazole (HBO) is known for undergoing intramolecular proton transfer in the excited state to result in the emission of its tautomer. A minor long-wavelength absorption band in the range 370-420 nm has been reported in highly polar solvents such as dimethylsulfoxide (DMSO). However, the nature of this species has not been entirely clarified. In this work, we provide evidence that this long-wavelength absorption band might have been caused by base or metal salt impurities that are introduced into the spectral sample during solvent transport using glass Pasteur pipettes. The contamination by base or metal salt could be avoided by using borosilicate glass syringes or nonglass pipettes in sample handling. Quantum chemical calculations conclude that solvent-mediated deprotonation is too energetically costly to occur without the aid of a base of an adequate strength. In the presence of such a base, the deprotonation of HBO and its effect on emission are investigated in dichloromethane and DMSO, the latter of which facilitates deprotonation much more readily than the former. Finally, the absorption and emission spectra of HBO in 13 solvents are reported, from which it is concluded that ESIPT is hindered in polar solvents that are also strong hydrogen bond acceptors.

  18. An 2-(2'-aminophenyl)benzoxazole-based OFF-ON fluorescent chemosensor for Zn2+ in aqueous solution.

    Science.gov (United States)

    Chen, Maliang; Lv, Xin; Liu, Yunlong; Zhao, Yun; Liu, Jing; Wang, Pi; Guo, Wei

    2011-04-01

    A water-soluble fluorescent sensor, 1, based on the "receptor-spacer-fluorophore" [2-(2'-aminophenyl)benzoxazole-amide-2-picolylamine] sensor platform, demonstrates the high sensitivity for Zn(2+) with a 25-fold fluorescence enhancement upon chelation to Zn(2+) and also exhibits high selectivity to Zn(2+) over other metal ions. X-ray crystal structure of Zn(2+) complex reveals that the amide oxygen (O2) cooperates with 2-picolylamine unit (N3, N4) as a receptor bind Zn(2+).

  19. Design and synthesis of benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-γ/δ dual agonists.

    Science.gov (United States)

    Gim, Hyo Jin; Cheon, Ye-Jin; Ryu, Jae-Ha; Jeon, Raok

    2011-05-15

    A series of benzoxazole or benzothiazole containing indole analogs, 6-alkoxyindole-2-carboxylic acids and 5-alkoxy-3-indolylacetic acids, were synthesized as novel candidates of PPARγ/δ dual agonists and their ligand activities for PPAR subtypes (α, γ, and δ) were investigated. In transient transactivation assay, several compounds activated PPARγ and δ with little activity of PPARα. Putative binding mode of the compounds 1a and 2a in the active site of PPARγ was similar with that of rosiglitazone and the molecular modeling provides molecular insight to the observed activity.

  20. Synthesis, photophysical property study of novel fluorescent 4-(1,3-benzoxazol-2-yl)-2-phenylnaphtho[1,2-][1,3]oxazole derivatives and their antimicrobial activity

    Indian Academy of Sciences (India)

    Kiran R Phatangare; Bhushan N Borse; Vikas S Padalkar; Vikas S Patil; Vinod D Gupta; Prashant G Umape; N Sekar

    2013-01-01

    A series of 4-(1,3-benzoxazol-2-yl)-2-phenylnaphtho[1,2-][1,3]oxazole derivatives have been synthesized from intermediate 1-amino-3-(1,3-benzoxazol-2-yl)naphthalen-2-ol. This intermediate was obtained by coupling 3-(1,3-benzoxazol-2-yl)naphthalen-2-ol with 4-sulphobenzenediazonium chloride followed by reduction with sodium dithionate in water at pH 8-9. 3-(1,3-benzoxazol-2-yl)naphthalen-2-ol was synthesized from 3-hydroxynaphthalene-2-carboxylic acid and 2-amino phenol in the presence of PCl3 in chlorobenzene at 130-135°C. All these compounds were characterized by FT-IR, 1H NMR, mass spectral and elemental analysis. The synthesized compounds are fluorescent which absorbs in the range of 296 to 332 nm while emits in the ranges of 368 to 404 nm with excellent quantum yield. All compounds were evaluated for in vitro antibacterial activities against Escherichia coli and Staphylococcus aureus strains and in vitro antifungal activity against Candida albicans and Aspergillus niger strains by using serial dilution method.

  1. Switchable and selective detection of Zn2+ or Cd2+ in living cells based on 3'-O-substituted arrangement of benzoxazole-derived fluorescent probes.

    Science.gov (United States)

    Xu, Yongqian; Xiao, Liangliang; Sun, Shiguo; Pei, Zhichao; Pei, Yuxin; Pang, Yi

    2014-07-18

    Two benzoxazole-derived ESIPT fluorescent sensors and show highly selective detection of Zn(2+) and Cd(2+), respectively, in aqueous solution and living cells. The selectivity switching from Zn(2+) to Cd(2+) is attributed to the different binding mode which is dependent on the 3'-O-substituted arrangement.

  2. Progress in the Synthesis of 2-Substituted Benzoxazoles Derivatives%2-取代苯并噁唑类化合物合成研究进展

    Institute of Scientific and Technical Information of China (English)

    肖立伟; 高红杰; 孔洁; 刘光仙; 彭晓霞; 王树军

    2014-01-01

    2-取代苯并噁唑类化合物在医药、农药以及配位催化等领域有广阔的应用前景,因而其合成方法备受关注。近年来,微波促进、水为介质、无溶剂合成、组合化学以及过渡金属催化等一系列高效、绿色的合成方法在2-取代苯并噁唑类化合物的合成中得到广泛的应用。按照不同的合成原料和合成方法进行分类,综述了近年来2-取代苯并噁唑类化合物合成研究的新进展。%2-Substituted benzoxazole derivatives play important roles in pharmaceuticals, pesticide and coordination cataly-sis, so the synthetic methods for 2-substituted benzoxazoles have been attracted widely. Recently, a series of efficient green methods such as microwave irradiation, water as solvent, solvent-free, combinatorial chemistry and transition metal catalysis etc. have been used to synthesize 2-substituted benzoxazoles derivatives. Based on different starting materials and different methods, the recent advances in synthesis of 2-substituted benzoxazole are reviewed.

  3. A comprehensive spectroscopic and computational investigation of intramolecular proton transfer in the excited states of 2-(2′-hydroxyphenyl) benzoxazole and its derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Padalkar, Vikas S. [Tinctorial Chemistry Group, Institute of Chemical Technology, Matunga, Mumbai 400019 (India); Ramasami, Ponnadurai, E-mail: ramchemi@intnet.mu [Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit (Mauritius); Sekar, Nagaiyan, E-mail: n.sekar@ictmumbai.edu.in [Tinctorial Chemistry Group, Institute of Chemical Technology, Matunga, Mumbai 400019 (India)

    2014-02-15

    The excited-state intramolecular proton transfer (ESIPT) fluorescence of the 2-(2′ hydroxyphenyl) benzoxazole (HBO) and its derivatives with NO{sub 2} as electron acceptor and NH{sub 2} as electron donor at the 4 and 5 position of benzoxazole ring was studied by spectroscopic and computational methods. The changes in the electronic transition, energy levels, and orbital diagrams of the HBO derivatives were investigated using the DFT computations and they were correlated with the experimental spectral emission. The benzoxazole derivatives are fluorescent under UV-light in solution. Photophysical properties of the compounds were also studied in solvents of different polarities. Experimental absorption and emission wavelengths are in agreement with those computed with a deviation ranging between 0 and 50%. The computational methods have been useful for molecular understanding of the transitions responsible for the fluorescent spectra. -- Highlights: • Experimental photophysical properties of 2-substituted benzoxazoles in different solvents have been studied and compared with the computational data. • Compounds show dual emission due to ESIPT process and was supported by DFT and TD-DFT computations. • Experimental results and computational results are in good agreements.

  4. Synthesis of new N-benzoxazole and N-benzothiazole derivatives of 3-(4-substituted phenyl) aminoisoxazol-5(2H)-ones and comparison of their base induced rearrangement

    Energy Technology Data Exchange (ETDEWEB)

    Khalafy, Jabbar; Marjani, Ahmad Poursattar; Ebrahimlo, Ali Reza Molla [Urmia University, Urmia (Iran, Islamic Republic of). Dept. of Chemistry]. E-mail: jkhalafi@yahoo.com

    2006-05-15

    3-Arylaminoisoxazol-5(2H)-ones, substituted on nitrogen with benzoxazole and benzothiazole groups react with triethylamine in ethanol under reflux to afford the corresponding indole and imidazobenzothiazole derivatives, respectively. (author)

  5. Excited state intramolecular proton transfer of 2-(2′,6′-dihydroxyphenyl)benzoxazole: Insights using computational methods

    Energy Technology Data Exchange (ETDEWEB)

    Tathe, Abhinav B.; Gupta, Vinod D.; Shreykar, Milind R. [Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, Maharashtra 400019 (India); Ramasami, Ponnadurai, E-mail: ramchemi@intnet.mu [Computational Chemistry Group, Department of Chemistry, Faculty of Science University of Mauritius, Réduit (Mauritius); Sekar, Nagaiyan, E-mail: n.sekar@ictmumbai.edu.in [Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, Maharashtra 400019 (India)

    2014-10-15

    The photo-physical behaviour of 2-(2′,6′-dihydroxyphenyl) benzoxazole was studied using the Density Functional Theory (DFT), Time Dependent Density Functional Theory (TD-DFT) and Configuration Interaction Singles (CIS). Different functionals including the hybrid and M06X series were used to compute the absorption and emission. Experimental absorption and emission wavelengths are in good agreement with those predicted using TD-DFT [TD-B3LYP/6–31 G(d)]. The further improvement was not observed with the larger basis sets like 6–31 G(d,p) and 6–311 G(d,p). The rotational barrier was also calculated theoretically in chloroform (10.5–14.1 kcal/mol) and it was found to be close to the experimental energy value (10.5 kcal/mol). - Highlights: • Photo-physical data of 2-(2′,6′-dihydroxyphenyl)benzoxazole was studied theoretically. • The methods employed are DFT, TD-DFT and CIS. • The rotational barriers evaluated computationally. • The results of DFT and TD-DFT are in good agreement with the experiments. • This study can lead to a better understanding of ESIPT phenomenon computationally.

  6. A Durable Alternative for Proton-Exchange Membranes: Sulfonated Poly(Benzoxazole Thioether Sulfone)s

    Energy Technology Data Exchange (ETDEWEB)

    Zhao, Dan; Li, Jin Hui; Song, Min Kyu; Yi, Baolian; Zhang, Huamin; Liu, Meilin

    2011-02-24

    To develop a durable proton-exchange membrane (PEM) for fuel-cell applications, a series of sulfonated poly(benzoxazole thioether sulfone)s ( SPTESBOs) are designed and synthesized, with anticipated good dimensional stability (via acid–base cross linking), improved oxidative stability against free radicals (via incorporation of thioether groups), and enhanced inherent stability (via elimination of unstable end groups) of the backbone. The structures and the degree of sulfonation of the copolymers are characterized using Fourier-transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy ({sup 1}H NMR and {sup 19}F NMR). The electrochemical stabilities of the monomers are examined using cyclic voltammetry in a typical three-electrode cell configuration. The physicochemical properties of the membranes vital to fuel-cell performance are also carefully evaluated under conditions relevant to fuel-cell operation, including chemical and thermal stability, proton conductivity, solubility in different solvents, water uptake, and swelling ratio. The new membranes exhibit low dimensional change at 25°C to 90°C and excellent thermal stability up to 250°C. Upon elimination of unstable end groups, the co-polymers display enhanced chemical resistance and oxidative stability in Fenton's test. Further, the SPTESBO-HFB-60 (HFB-60=hexafluorobenzene, 60 mol% sulfone) membrane displays comparable fuel-cell performance to that of an NRE 212 membrane at 80°C under fully humidified condition, suggesting that the new membranes have the potential to be more durable but less expensive for fuel-cell applications.

  7. A durable alternative for proton-exchange membranes: sulfonated poly(benzoxazole thioether sulfone)s

    Energy Technology Data Exchange (ETDEWEB)

    Zhao, Dan [Center for Innovative Fuel Cell and Battery Technologies, School of Materials Science and Engineering, Georgia Institute of Technology, Atlanta, GA 30332-0245 (United States); Lab of PEMFC Key Materials and Technologies, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Liaoning, Dalian 116023 (China); Graduate School of the Chinese Academy of Sciences, Beijing 100039 (China); Li, Jinhuan [Center for Innovative Fuel Cell and Battery Technologies, School of Materials Science and Engineering, Georgia Institute of Technology, Atlanta, GA 30332-0245 (United States); College of Materials Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 210016 (China); Song, Min-Kyu; Liu, Meilin [Center for Innovative Fuel Cell and Battery Technologies, School of Materials Science and Engineering, Georgia Institute of Technology, Atlanta, GA 30332-0245 (United States); Yi, Baolian; Zhang, Huamin [Lab of PEMFC Key Materials and Technologies, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Liaoning, Dalian 116023 (China)

    2011-03-18

    To develop a durable proton-exchange membrane (PEM) for fuel-cell applications, a series of sulfonated poly(benzoxazole thioether sulfone)s (SPTESBOs) are designed and synthesized, with anticipated good dimensional stability (via acid-base cross linking), improved oxidative stability against free radicals (via incorporation of thioether groups), and enhanced inherent stability (via elimination of unstable end groups) of the backbone. The structures and the degree of sulfonation of the copolymers are characterized using Fourier-transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy ({sup 1}H NMR and {sup 19}F NMR). The electrochemical stabilities of the monomers are examined using cyclic voltammetry in a typical three-electrode cell configuration. The physicochemical properties of the membranes vital to fuel-cell performance are also carefully evaluated under conditions relevant to fuel-cell operation, including chemical and thermal stability, proton conductivity, solubility in different solvents, water uptake, and swelling ratio. The new membranes exhibit low dimensional change at 25 C to 90 C and excellent thermal stability up to 250 C. Upon elimination of unstable end groups, the co-polymers display enhanced chemical resistance and oxidative stability in Fenton's test. Further, the SPTESBO-HFB-60 (HFB-60=hexafluorobenzene, 60 mol% sulfone) membrane displays comparable fuel-cell performance to that of an NRE 212 membrane at 80 C under fully humidified condition, suggesting that the new membranes have the potential to be more durable but less expensive for fuel-cell applications. (Copyright copyright 2011 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim)

  8. Reproducibility and correctness of the procedure of photometric determination of beryllium with 2-(o-hydroxyphenyl)benzoxazole

    Energy Technology Data Exchange (ETDEWEB)

    Tikhonova, N.B.; Charykov, A.K.; Gladilovich, D.B.

    1985-09-01

    This paper discusses two methods of evaluation of correctness on the example of the fluorometric determination of beryllium by 2-(o-hydroxyphenyl) benzoxazole (HPBO), as well as an evaluation of the reproducibility of this procedure for the level of beryllium concentration 10-36 ng/ml. The traditional method of detection and evaluation of systematic errors in chemical analysis is comparison of the average result of repeated analysis of a standard sample with specified content of the component to be determined. The second method discussed is based on an experimental estimation of the constant and proportional components of the systematic error by a combination of the methods of doubling and additives. It is shown that the fluorometric method of determining beryllium with HPBO at an absolute beryllium content of 0.25-1.0 micrograms is satisfactorily reproducible and does not contain systematic errors at the level of significance beta=0.05.

  9. Oxazoles revisited: On the nature of binding of benzoxazole and 2-methylbenzoxazole with the zinc and palladium halides.

    Science.gov (United States)

    Jones, Roderick C; Chojnacka, Maja W; Quail, J Wilson; Gardiner, Michael G; Decken, Andreas; Yates, Brian F; Gossage, Robert A

    2011-02-21

    A synthetic and structural (X-ray) investigation into the bonding modes of benzoxazole (box) and 2-methylbenzoxazole (Mebox) ligands with halide precursors of Zn and Pd has been undertaken to clarify earlier discrepancies concerning the nature of the bonding mode(s) of the two azoles. In four structurally characterised examples, all contain the title ligands in a κ(1)N bonding motif. Calculations at the density functional level (DFT) of theory (B3LYP) confirm the ground state stability of this class of coordination for several hypothetical Pd and Zn (gas phase) compounds. The attempt to obtain suitable crystalline material of PdCl(2)(box)(2) (i.e., 5) leads to substantial complex degradation. One minor product of this process has been identified (X-ray) as the diarylformamidinato complex C(26)H(22)N(4)O(4)Pd, presumably formed via a complex combination of the decomposition products of both free box and 5.

  10. Fluorescent dendritic organogels based on 2-(2'-hydroxyphenyl)benzoxazole: emission enhancement and multiple stimuli-responsive properties.

    Science.gov (United States)

    Chen, Hui; Feng, Yu; Deng, Guo-Jun; Liu, Zhi-Xiong; He, Yan-Mei; Fan, Qing-Hua

    2015-07-27

    A new highly efficient and versatile poly(benzyl ether) dendritic organogelator HPB-G1 with 2-(2'-hydroxyphenyl)benzoxazole (HPB) at the focal point has been designed and synthesized. HPB-G1 can form stable organogels toward various apolar and polar organic solvents. Further studies revealed that intermolecular multiple π-π stacking interactions are the main driving forces for the formation of the organogels. Notably, dendron HPB-G1 exhibited a significantly enhanced emission in the gel state in contrast to weak emission in solution. Most interestingly, these dendritic organogels exhibited multiple stimuli-responsive behaviors upon exposure to environmental stimuli, including temperature, sonication, shear stress, and the presence of anions, metal cations, acids/bases, thus leading to reversible sol-gel phase transitions.

  11. A green and efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using heteropolyanion-based ionic liquids: as a recyclable solid catalyst.

    Science.gov (United States)

    Vahdat, Seyed Mohammad; Baghery, Saeed

    2013-09-01

    In this paper, we introduce two nonconventional ionic liquid compounds which are composed of propane sulfonate functionalized organic cations and heteropolyanions as green solid acid catalysts for the highly efficient and green synthesis of 2,3-disubstitutedquinoxaline derivatives. These ionic liquids are in the solid state at room temperature and the synthesis is carried out via the one-pot condensation reaction of various o-phenylenediamine with 1,2-diketone derivatives. Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the one-pot condensation from reaction orthoester with o-aminophenol (synthesis of benzoxazole derivatives) and ophenylenediamine (synthesis of benzimidazole derivatives). All experiments successfully resulted in the desired products. The described novel synthesis method has several advantages of safety, mild condition, high yields, short reaction times, simplicity and easy workup compared to the traditional method of synthesis.

  12. Radiosynthesis and in vivo evaluation of a ¹⁸F-labelled styryl-benzoxazole derivative for β-amyloid targeting.

    Science.gov (United States)

    Ribeiro Morais, G; Gano, L; Kniess, T; Bergmann, R; Abrunhosa, A; Santos, I; Paulo, A

    2013-12-01

    The formation of β-amyloid deposits is considered a histopathological feature of Alzheimer's disease (AD). In vivo molecular imaging by means of amyloid-avid radiotracers will allow for an early and conclusive diagnostic of AD. Herein, we describe the radiosynthesis of the radiofluorinated styryl benzoxazole derivative [¹⁸F]-[2-[N-methyl-N-(2'-fluoroethyl)-4'-aminostyryl]benzoxazole] ([¹⁸F]-1) and its pre-clinical evaluation, including metabolic and biodistribution studies in male Wistar rats. The in vivo biological evaluation of [¹⁸F]-1 showed that this new radiotracer has a moderate brain uptake with a slow brain washout and a poor in vivo stability.

  13. 2-Arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria.

    Science.gov (United States)

    Cellier, Marie; Fabrega, Olivier J; Fazackerley, Elizabeth; James, Arthur L; Orenga, Sylvain; Perry, John D; Salwatura, Vindhya L; Stanforth, Stephen P

    2011-05-01

    A series of 2-(2-nitrophenyl)benzothiazole 7, 2-(2-nitrophenyl)benzoxazole 10 and 2-(2-nitrophenyl)benzimidazole 13 derivatives have been synthesised and assessed as indicators of nitroreductase activity across a range of clinically important Gram negative and Gram positive bacteria. The majority of Gram negative bacteria produced strongly fluorescent colonies with substrates 7 and 10 whereas fluorescence production in Gram positive bacteria was less widespread. The l-alanine 16 and 19 and β-alanine 21 and 23 derivatives have been prepared from 2-(2-aminophenyl)benzothiazole 14 and 2-(2-aminophenyl)benzoxazole 17. These four compounds have been evaluated as indicators of aminopeptidase activity. The growth of Gram positive bacteria was generally inhibited by these substrates but fluorescent colonies were produced with the majority of Gram negative bacteria tested.

  14. Synthesis and spectra of a kind of novel longer-wavelength benzoxazole indole styryl cyanine dye with a carbazole-bridged chain.

    Science.gov (United States)

    Fei, Xuening; Gu, Yingchun; Li, Chao; Liu, Yuru; Yu, Lu

    2013-01-01

    Based on cyanine dye probe oxazole yellow (YO) and Cy(3), a series of novel styryl cyanine dyes were designed and synthesized. Carbazole was inserted into the structures of YO and Cy(3) to act as a bridge to link the benzoxazole and indole group. This modification resulted in a novel kind of benzoxazole indole styryl cyanine dye with a carbazole-bridged chain. The dyes were characterized by (1)HNMR and MS. The spectra of the novel dyes were also performed and the results showed that the maximum emission wavelength of the carbazole styryl cyanine dye was shifted red, the Stokes shift increased and the fluorescence intensity enhanced compared with those of YO and Cy(3). These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.

  15. Synthesis, characterization and catalytic activity of copper(II) complexes containing a redox-active benzoxazole iminosemiquinone ligand.

    Science.gov (United States)

    Balaghi, S Esmael; Safaei, Elham; Chiang, Linus; Wong, Edwin W Y; Savard, Didier; Clarke, Ryan M; Storr, Tim

    2013-05-21

    A tridentate benzoxazole-containing aminophenol ligand HL(BAP) was synthesized and complexed with Cu(II). The resulting Cu(II) complexes were characterized by X-ray, IR, UV-vis-NIR spectroscopies, and magnetic susceptibility studies, demonstrating that the ligand is oxidized to the o-iminosemiquinone form [L(BIS)](-) in the isolated complexes. L(BIS)Cu(II)Cl exhibits a distorted tetrahedral geometry, while L(BIS)Cu(II)OAc is square pyramidal. In both solid state structures the ligand is coordinated to Cu(II)via the benzoxazole, as well as the nitrogen and oxygen atoms from the o-iminosemiquinone moiety. The chloride, or acetate group occupies the fourth and/or fifth positions in L(BIS)Cu(II)Cl and L(BIS)Cu(II)OAc, respectively. Magnetic susceptibility measurements indicate that both complexes are diamagnetic due to antiferromagnetic coupling between the d(9) Cu(II) centre and iminosemiquinone ligand radical. Electrochemical studies of the complexes demonstrate both a quasi-reversible reduction and oxidation process for the Cu complexes. While L(BIS)Cu(II)X (X = Cl) is EPR-silent, chemical oxidation affords a species with an EPR signal consistent with ligand oxidation to form a d(9) Cu(II) iminoquinone species. In addition, chemical reduction results in a Cu(II) centre most likely bound to an amidophenoxide. Mild and efficient oxidation of alcohol substrates to the corresponding aldehydes was achieved with molecular oxygen as the oxidant and L(BIS)Cu(II)X-Cs2CO3 as the catalyst.

  16. Novel benzoxazole derivatives DCPAB and HPAB attenuate Th1 cell-mediated inflammation through T-bet suppression

    Science.gov (United States)

    Oh, Yeon Ji; Kim, Darong; Oh, Sera; Jang, Eun Jung; Won, Hee Yeon; Jeong, Hana; Jeong, Mi Gyeong; Choo, Hea-Young Park; Hwang, Eun Sook

    2017-01-01

    Interferon-γ (IFN-γ), a critical inflammatory cytokine, is primarily produced by T helper 1 (Th1) cells and accelerates the pathogenesis of inflammatory colitis. Pharmacological suppression of IFN-γ production attenuates dysregulated inflammatory responses and may be beneficial for treating inflammatory disease. In this study, we aimed to discover potent anti-inflammatory compounds that suppress IFN-γ production and found that the novel benzoxazole derivatives, 2-((3,4-dichlorophenyl) amino) benzo[d]xazol-5-ol (DCPAB) and 2-((3,4-hydroxyphenyl) amino) benzo[d]xazol-5-ol (HPAB), suppressed IFN-γ production by T cells. Treatment of CD4+ T cells with DCPAB and HPAB selectively inhibited Th1 cell development, and DCPAB more potently suppressed IFN-γ than HPAB did. Interestingly, DCPAB and HPAB significantly suppressed the expression of T-box containing protein expressed in T cells (T-bet) that activates IFN-γ gene transcription. DCPAB additionally suppressed transcriptional activity of T-bet on IFN-γ gene promoter, whereas HPAB had no effect on T-bet activity. IFN-γ suppressive activity of DCPAB and HPAB was impaired in the absence of T-bet but was retrieved by the restoration of T-bet in T-bet-deficient T cells. Furthermore, DCPAB and HPAB attenuated inflammatory colitis development that was induced by CD4+ T cells in vivo. We suggest that the novel benzoxazole derivatives, DCPAB and HPAB, may have therapeutic effects on inflammatory colitis. PMID:28169371

  17. Modulating the near-infrared luminescence of neodymium and ytterbium complexes with tridentate ligands based on benzoxazole-substituted 8-hydroxyquinolines.

    Science.gov (United States)

    Shavaleev, Nail M; Scopelliti, Rosario; Gumy, Frédéric; Bünzli, Jean-Claude G

    2009-04-01

    An improved synthesis of 2-(2'-benzothiazole)- and 2-(2'-benzoxazole)-8-hydroxyquinoline ligands that combine a tridentate N,N,O-chelating unit for metal binding and extended chromophore for light harvesting is developed. The 2-(2'-benzoxazole)-8-hydroxyquinoline ligands form mononuclear nine-coordinate complexes with neodymium, [Nd(kappa(3)-ligand)(3)], and an eight-coordinate complex with ytterbium, [Yb(kappa(3)-ligand)(2) x (kappa(1)-ligand) x H(2)O], as verified by crystallographic characterization of five complexes with four different ligands. The chemical stability of the complexes increases when the ligand contains 5,7-dihalo-8-hydroxyquinoline versus an 8-hydroxyquinoline group. The complexes feature a ligand-centered visible absorption band with a maximum at 508-527 nm and an intensity of (7.5-9.6) x 10(3) M(-1) x cm(-1). Upon excitation with UV and visible light within ligand absorption transitions, the complexes display characteristic lanthanide luminescence in the near-infrared at 850-1450 nm with quantum yields and lifetimes in the solid state at room temperature as high as 0.33% and 1.88 micros, respectively. The lanthanide luminescence in the complexes is enhanced upon halogenation of the 5,7-positions in the 8-hydroxyquinoline group and upon the addition of electron-donating substituents to the benzoxazole ring. Facile modification of chromophore units in 2-(2'-benzoxazole)-8-hydroxyquinoline ligands provides means for controlling the luminescence properties of their lanthanide complexes.

  18. In vivo visualization of alpha-synuclein deposition by carbon-11-labelled 2-[2-(2-dimethylaminothiazol-5-yl)ethenyl]-6-[2-(fluoro)ethoxy]benzoxazole positron emission tomography in multiple system atrophy.

    Science.gov (United States)

    Kikuchi, Akio; Takeda, Atsushi; Okamura, Nobuyuki; Tashiro, Manabu; Hasegawa, Takafumi; Furumoto, Shozo; Kobayashi, Michiko; Sugeno, Naoto; Baba, Toru; Miki, Yasuo; Mori, Fumiaki; Wakabayashi, Koichi; Funaki, Yoshihito; Iwata, Ren; Takahashi, Shoki; Fukuda, Hiroshi; Arai, Hiroyuki; Kudo, Yukitsuka; Yanai, Kazuhiko; Itoyama, Yasuto

    2010-06-01

    The histopathological hallmark of multiple system atrophy is the appearance of intracellular inclusion bodies, named glial cytoplasmic inclusions, which are mainly composed of alpha-synuclein fibrils. In vivo visualization of alpha-synuclein deposition should be used for the diagnosis and assessment of therapy and severity of pathological progression in multiple system atrophy. Because 2-[2-(2-dimethylaminothiazol-5-yl)ethenyl]-6-[2-(fluoro)ethoxy] benzoxazole could stain alpha-synuclein-containing glial cytoplasmic inclusions in post-mortem brains, we compared the carbon-11-labelled 2-[2-(2-dimethylaminothiazol-5-yl)ethenyl]-6-[2-(fluoro)ethoxy] benzoxazole positron emission tomography findings of eight multiple system atrophy cases to those of age-matched normal controls. The positron emission tomography data demonstrated high distribution volumes in the subcortical white matter (uncorrected P benzoxazole positron emission tomography is a promising surrogate marker for monitoring intracellular alpha-synuclein deposition in living brains.

  19. Common benzothiazole and benzoxazole fluorescent DNA intercalators for studying Alzheimer Aβ1-42 and prion amyloid peptides.

    Science.gov (United States)

    Stefansson, Steingrimur; Adams, Daniel L; Tang, Cha-Mei

    2012-05-01

    Amyloids are fibrillar protein aggregates associated with a number of neurodegenerative pathologies including Alzheimer and Creutzfeldt-Jakob disease. The study of amyloids is usually based on fluorescence with the dye thioflavin-T. Although a number of amyloid binding compounds have been synthesized, many are nonfluorescent or not readily available for research use. Here we report on a class of commercial benzothiazole/benzoxazole containing fluorescent DNA intercalators from Invitrogen that possess the ability to bind amyloid Aβ1-42 peptide and hamster prion. These dyes fluoresce from 500-750 nm and are available as dimers or monomers. We demonstrate that these dyes can be used as acceptors for thioflavin-T fluorescence resonance energy transfer as well as reporter groups for binding studies with Congo red and chrysamine G. As more potential therapeutic compounds for these diseases are generated, there is a need for simple and inexpensive methods to monitor their interactions with amyloids. The fluorescent dyes reported here are readily available and can be used as tools for biochemical studies of amyloid structures and in vitro screening of potential therapeutics.

  20. Synthesis, vibrational spectroscopic investigations, molecular docking, antibacterial and antimicrobial studies of 5-ethylsulphonyl-2-(p-aminophenyl)benzoxazole

    Science.gov (United States)

    Parveen S, Shana; Al-Alshaikh, Monirah A.; Panicker, C. Yohannan; El-Emam, Ali A.; Arisoy, Mustafa; Temiz-Arpaci, Ozlem; Van Alsenoy, C.

    2016-07-01

    The optimized molecular structure, vibrational wavenumbers, corresponding vibrational assignments of 5-ethylsulphonyl-2-(p-aminophenyl)benzoxazole have been investigated experimentally and theoretically based on density functional theory. Synthesis and antibacterial and antimicrobial activities of the title compound were reported. The FT-IR and FT-Raman spectra were recorded in solid phase and the experimental bands were assigned and characterized on the basis of potential energy distribution. The HOMO and LUMO energies show that the charge transfer occur within the molecule. Stability arising from hyperconjugative interactions and charge delocalization were analysed using natural bond orbital analysis. Binding free energy of -9.8 kcal/mol as predicted by docking studies suggests good binding affinity and the inhibitor forms a stable complex with FAK as is evident from the ligand-receptor interactions. The title compound possesses lower activity against Candida albicans with MIC value of 64 μg/ml than the compared reference drugs as fluconazole and amphotericin B and possesses the same activity with value of 64 μg/ml against Candida krusei as the reference drug, fluconazole.

  1. Novel Benzothiazole, Benzimidazole and Benzoxazole Derivatives as Potential Antitumor Agents: Synthesis and Preliminary in Vitro Biological Evaluation

    Directory of Open Access Journals (Sweden)

    Li Yang

    2012-01-01

    Full Text Available In a previous hit-to-lead research program targeting anticancer agents, two promising lead compounds, 1a and 1b, were found. However, the poor solubility of 1a and 1b made difficult further in vivo studies. To solve this problem, a lead optimization was conducted through introducing N-methyl-piperazine groups at the 2-position and 6-position. To our delight, the optimized analogue 1d showed comparable antiproliferative activity in vitro with better solubility, compared with 1a. Based on this result, the replacement of the benzothiazole scaffold with benzimidazole and benzoxazole moieties afforded 1f and 1g, whose activities were fundamentally retained. In the preliminary in vitro biological evaluation, the immunofluorescence staining of HCT116 cells indicated that 1d, 1f and 1g led to cytosolic vacuolization which was not induced by 1a at low micromolecular concentrations. These results suggest that these optimized compounds might potentially constitute a novel class of anticancer agents, which merit further studies.

  2. Novel benzothiazole, benzimidazole and benzoxazole derivatives as potential antitumor agents: synthesis and preliminary in vitro biological evaluation.

    Science.gov (United States)

    Xiang, Pu; Zhou, Tian; Wang, Liang; Sun, Chang-Yan; Hu, Jing; Zhao, Ying-Lan; Yang, Li

    2012-01-17

    In a previous hit-to-lead research program targeting anticancer agents, two promising lead compounds, 1a and 1b, were found. However, the poor solubility of 1a and 1b made difficult further in vivo studies. To solve this problem, a lead optimization was conducted through introducing N-methyl-piperazine groups at the 2-position and 6-position. To our delight, the optimized analogue 1d showed comparable antiproliferative activity in vitro with better solubility, compared with 1a. Based on this result, the replacement of the benzothiazole scaffold with benzimidazole and benzoxazole moieties afforded 1f and 1g, whose activities were fundamentally retained. In the preliminary in vitro biological evaluation, the immunofluorescence staining of HCT116 cells indicated that 1d, 1f and 1g led to cytosolic vacuolization which was not induced by 1a at low micromolecular concentrations. These results suggest that these optimized compounds might potentially constitute a novel class of anticancer agents, which merit further studies.

  3. Multivariate regression modelling of antifungal activity of some benzoxazole and oxazolo[4,5-b]pyridine derivatives.

    Science.gov (United States)

    Kovačević, Strahinja Z; Podunavac Kuzmanović, Sanja O; Jevrić, Lidija R

    2013-01-01

    In the present study, principal component analysis (PCA) followed by principal component regression (PCR) and partial least squares (PLS) method was applied in order to identify the most important in silico molecular descriptors and quantify their influence on antifungal activity (expressed as minimal inhibitory concentration) of selected benzoxazole and oxazolo[4,5-b]pyridine derivatives against Candida albicans. PLS regression showed the best statistical performance, according to the lowest value of the standard error (root mean square errors of calibration of 0.02526 and cross-validation of 0.04533), while PCR model was characterized by root mean square errors of calibration of 0.03176 and cross-validation of 0.05661. The most important descriptors in both PLS and PCR model are solubility in water, expressed as AClogS and ABlogS, and lipophilicity, expressed as XlogP2 and ABlogP. Very good predictive ability of the established models, confirmed by corresponding statistical parameters, allows us to estimate antifungal activity of structurally similar compounds.

  4. Dimer of Bis[trans-5-methyl-2-[2-(4-methoxylphenyl) ethenyl]-benzoxazole]di-μ-nitratosilver(I)

    Institute of Scientific and Technical Information of China (English)

    LIU Hui-Min; ZHANG Wei; XIN Ying; ZHANG Wen-Qin

    2004-01-01

    The title complex [AgNO3(C17H15NO2)2]2 was synthesized and characterized by X-ray diffraction analysis. The compound crystallizes in triclinic, space group Pī with a = 11.226(7), b = 11.906(7), c = 12.144(7) (A。), α = 99.796(10), β = 91.631(10), γ = 101.225(10)°, V = 1565.6(16)(A。)3, Z = 1, Mr = 1400.96, Dc = 1.486 g/cm3, F(000) = 716 and μ(Mo-Kα) = 0.697 mm-1. The final R and wR are 0.0401 and 0.0995, respectively for 5492 independent observable reflections with I > 2σ(I). The results show that the central Ag atom is four-coordinated with two O atoms from two distinct NO3- anions and two N atoms from two trans-5-methyl-2-[2-(4-methoxylphenyl)ethenyl]- benzoxazole ligands, and the two Ag atoms bridged with two O atoms give an interesting Ag-O-Ag-O parallelogram structure. The coordination sphere of Ag atom exhibits a heavily distorted tetrahedral geometry and the coordination angles lie in the range of 66.73(12)~129.59(10)°. The intra- molecular dihedral angles between the benzoxazolyl and phenyl planes are 4.1(3) and 2.9(3)°, respectively.

  5. FT-IR, FT-Raman, SERS and computational study of 5-ethylsulphonyl-2-(o-chlorobenzyl)benzoxazole.

    Science.gov (United States)

    Mary, Y Sheena; Raju, K; Yildiz, Ilkay; Temiz-Arpaci, Ozlem; Nogueira, Helena I S; Granadeiro, Carlos M; Van Alsenoy, Christian

    2012-10-01

    FT-IR, FT-Raman and surface-enhanced Raman scattering spectra of 5-ethylsulphonyl-2-(o-chlorobenzyl)benzoxazole were recorded and analyzed. The vibrational wavenumbers were examined theoretically using the Gaussian09 set of quantum chemistry codes, and the normal modes were assigned by potential energy distribution calculations. The presence of CH(2), SO(2) and CH(3) modes in the SERS spectrum indicates the nearness of the methyl group to the metal surface which affects the orientation and metal molecule interaction. The synthesis, NMR spectra and antibacterial properties are reported. The title compound shows more inhibitory effect against Pseudomonas aeruginosa than ampicillin and found to be more potent against Klebsiella pneumoniae and drug-resistant Bacillus subtilis than the other microorganisms. A computation of the first hyperpolarizability indicates that the compound may be a good candidate as a NLO material. The RMS errors of the observed Raman and IR bands are found to be 30.93, 29.77 for HF and 9.57, 6.75 for DFT methods, respectively.

  6. Synthesis of luminescent ethynyl-extended regioisomers of borate complexes based on 2-(2'-hydroxyphenyl)benzoxazole.

    Science.gov (United States)

    Massue, Julien; Frath, Denis; Retailleau, Pascal; Ulrich, Gilles; Ziessel, Raymond

    2013-04-22

    A series of thirteen luminescent tetrahedral borate complexes based on the 2-(2'-hydroxyphenyl)benzoxazole (HBO) core is presented. Their synthesis includes the incorporation of an ethynyl fragment by Sonogashira cross-coupling reaction, with the goal of extending the conjugation and consequently redshifting their emission wavelength. Different regioisomers, substituted in the 3-, 4-, or 5-position of the phenolate side of the HBO core, were studied in order to compare their photophysical properties. The complexes were characterized by X-ray diffraction and NMR, UV/Vis, and emission spectroscopy in solution and in the solid state. In all cases, complexation to boron leads to a donor-acceptor character that impacts their photophysical properties. Complexes with a 3- or 5-substituted fragment display mild to pronounced internal charge transfer (ICT), a feature strengthened by the presence of p-dibutylaminophenylacetylene in the molecular structure, protonation of the nitrogen atom of which leads to a significant blueshift and an increase in quantum yield. On the contrary, when the ethynyl module is grafted on the 4-position, narrow, structured, symmetrical absorption/emission bands are observed. Moreover, the fact that protonation has little effect on the emission maximum wavelength reveals singlet excited-state decay. Solid-state emission properties reveal a redshift compared to solution, explained by tight packing of the π-conjugated systems and the high planarity of the dyes. Subsequent connection of these complexes to other photoactive subunits (BODIPY, Boranil) provides dyads in which efficient cascade energy transfer is observed.

  7. 苯并噁唑与苯并噻唑的合成方法∗%Methods for Synthesis of Benzoxazole and Benzothiazole

    Institute of Scientific and Technical Information of China (English)

    周晓玉; 陈霞; 杨发旺; 刘义龙; 令狐克美

    2016-01-01

    苯并噁唑和苯并噻唑等芳香杂环化合物是一类重要的有机合成中间体,是许多医药、农药、天然产物和功能分子等的骨架结构。因此,该类化合物的合成备受广大研究者的关注。本文着重综述了近年来此类化合物的合成发展情况,按照分子间缩合和分子内缩合反应进行分类归纳总结。文章还结合目前有机合成的前沿领域和现状,提出了目前各种合成方法存在的不足和缺陷。最后,在课题组研究工作的基础上,提出了合成此类化合物的研究前景和展望。%Benzoxazole and benzothiazole, which are common and important substructures in pharmaceuticals, pesticides, natural products and biologically active molecules, are widely used in organic synthesis and concerned by many researchers. The synthesis of benzoxazole and benzothiazol by intermolecular condensation reactions and intramolecular condensation reactions currently were described. The deficiencies and shortcomings of the existing synthesis methods were also described. Finally, the research prospects and expectation for the synthesis of benzoxazole and benzothiazole were proposed based on our previous work.

  8. Zn2+-triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative.

    Science.gov (United States)

    Xu, Yongqian; Pang, Yi

    2011-02-21

    Near-infrared (NIR) emission can offer distinct advantages for biological applications. A fluorescent sensor, Zinhbo-1, based on bis(benzoxazole) ligand with 2,2'-dipicolylamine (DPA) as receptor, was synthesized. In aqueous solution, Zinhbo-1 demonstrates high sensitivity and selectivity for sensing Zn(2+) with about 10-fold enhancement and nanomolar sensitivity (K(d) = 0.29 nM). Moreover, sensor Zinhbo-1 can detect Zn(2+) in near-infrared region (over 700 nm) with large Stokes shift (ca. 230 nm) attributing to the Zn(2+)-induced excited state intramolecular proton transfer (ESIPT).

  9. Unique regioselectivity in the C(sp3)-H α-alkylation of amines: the benzoxazole moiety as a removable directing group.

    Science.gov (United States)

    Lahm, Günther; Opatz, Till

    2014-08-15

    The benzoxazol-2-yl- substituent was found to act as a removable activating and directing group in the Ir-catalyzed alkylation of C(sp(3))-H bonds adjacent to nitrogen in secondary amines. It can be easily introduced by oxidative coupling or by an SNAr reaction, and it can be removed by hydroxide or by hydride reduction. For 1,2,3,4-tetrahydroisoquinolines, activation exclusively takes place in the 3-position. A variety of activated as well as unactivated terminal olefins are suitable reaction partners.

  10. Conformational Analysis of Poly-2,5-Benzimidazole (ABPBI), Poly-2,5- Benzoxazole (ABPBO), and Poly-2,6-Benzothiazole (ABPBT) Dimers by the Modified Neglect of Diatomic Overlap (MNDO) and Austin Method 1 (AM1) Semiempirical Molecular Orbital Methods

    Science.gov (United States)

    1987-07-01

    AFWAL-TR-87-4034 A\\) CONFORMATIONAL ANALYSIS OF POLY-2,5-BENZOIMIDAZOLE (ABPBI), POLY-2,5-BENZOXAZOLE (ABPBO), AND POLY-2,6- BENZOTHIAZOLE (ABPBT... benzothiazole Molecular Orbital 19. ABSTRACT (Continue on reverse if necessar and identif-y by block number) The two repeat unit analogs of three, aromatic...SECURITY CLASSIFICATION OF THIS PAGE 11. TITLE (Cont) Poly-2,5-benzoxazole (ABPBO), and Poly-2,6- benzothiazole (ABPBT) Dimers by the Modified Neglect

  11. Synthesis, FT-IR investigation and computational study of 5-[(4-Bromophenyl)acetamido]-2-(4-tert-butylphenyl) benzoxazole.

    Science.gov (United States)

    Bhagyasree, J B; Samuel, Jadu; Varghese, Hema Tresa; Panicker, C Yohannan; Arisoy, Mustafa; Temiz-Arpaci, Ozlem

    2013-11-01

    The synthesis and antimicrobial properties of 5-[(4-Bromophenyl)acetamido]-2-(4-tertbutylphenyl) benzoxazole are reported in the present work. The optimized molecular structure, (1)H NMR, vibrational frequencies, corresponding vibrational assignments of 5-[(4-Bromophenyl)acetamido]-2-(4-tert-butylphenyl) benzoxazole have been investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of the normal modes of vibrations was done using GAR2PED program. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. MEP was performed by the SDD method and the predicted infrared intensities have also been reported. The calculated geometrical parameters are in agreement with that of similar derivates. The first hyperpolarizability is high and the title compound is suitable for further NLO studies. Microbiological results indicated that the title compound possessed a broad spectrum activity against the tested Gram-positive, Gram-negative bacteria.

  12. 一锅法合成苯并噁唑类化合物%A one-pot synthetic route to substituted benzoxazoles

    Institute of Scientific and Technical Information of China (English)

    唐叶绿; 杜宗波; 江国防

    2016-01-01

    Aliphatic acids, aromatic acids andβ-aryl-α,β-unsaturated acids were selected to react witho-aminophenol in the presence of phosphorus oxytrichloride (POCl3) in refluxing CHCl3 to afford four series of 2-alkyl,2-aryl and 2-styryl benzoxazoles,respectively, and a possible reaction mechanism for their synthesis was proposed. The reaction conditions including the molar ratio of substrates and POCl3, the structure and activity of carboxylic acid, the reaction temperature and the different solvents were optimized. All the structures of the target products were confirmed by1HNMR and MS.The results show that the molar ratio of substrates and the different carboxylic acid structures play an important role in the yields of benzoxazoles. The impact of the selected solvent on yield is relatively small when the reaction temperature equals or surpasses 60℃. The yields of 2-alkyl substituted benzoxazoles are significantly higher than those of 2-phenyl and 2-styryl substituted benzoxazoles. The method is concise and efficient for the synthesis of 2-substituted benzoxazoles.%以三氯氧磷(POCl3)为缩合剂,将邻氨基苯酚和羧酸在CHCl3中回流一锅法合成4个系列的2-烷基、2-芳基、2-苯乙烯基取代的苯并噁唑类化合物,并研究其可能的反应历程;通过考察反应过程中邻氨基苯酚和羧酸以及POCl3的物质的量比、羧酸的结构及活性、反应温度以及溶剂种类对目标化合物产率的影响,得到最佳的反应条件参数,并对目标化合物进行1HNMR和MS表征。研究结果表明:邻氨基苯酚和羧酸以及POCl3的物质的量比、羧酸的结构及活性对苯并噁唑的产率影响比较大;当温度达到或超过60℃时,所选的溶剂对其产率的影响比较小;2-烷基取代苯并噁唑的产率整体比2-芳基和2-苯乙烯基取代的苯并噁唑产率高;该方法是一种简便、高效的合成2-取代苯并噁唑类化合物的方法。

  13. Synthesis, photophysical properties of novel fluorescent metal complexes from 3-(1,3-benzoxazol-2-ylnaphthalen-2-ol, and their antimicrobial activities

    Directory of Open Access Journals (Sweden)

    Vinod D. Gupta

    2012-01-01

    Full Text Available A series of novel metal complexes containing metal atoms such as Zn, Co, Cu, Cd, Ni, Mg and Sn have been synthesized from 3-(1,3-benzoxazol-2-ylnaphthalen-2-ol. The synthesized ligand was well characterized by IR, 1H-NMR and mass spectrometry. The electrochemical properties were studied by cyclic voltammetric analysis. The synthesized complexes are fluorescent and absorb in the range of 317 to 323 nm while emit in the range of 371 to 416 nm with good quantum yield. All metal complexes show significant in vitro antibacterial activity against E. coli and S. aureus strains and in vitro antifungal activity against C. albicans and A. niger strains by using serial dilution method. The antibacterial activities were expressed as the minimum inhibitory concentration (MIC in μg/mL.

  14. Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfanylacetyl]-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

    Directory of Open Access Journals (Sweden)

    G. Aridoss

    2011-07-01

    Full Text Available In the title compound, C29H26N2O5S, the piperidine ring adopts a half-chair conformation. The phenyl rings are oriented at dihedral angles of 75.76 (12 and 86.64 (9° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 30.81 (13°. The benzoxazole ring system is approximately planar [maximum deviation = 0.016 (4 Å]. The atoms of the ethyl side chain are disordered over two sets of sites [site occupancies = 0.376 (9 and 0.624 (9]. The molecular conformation is stabilized by an intramolecular O—H...O hydrogen bond, generating an S(6 motif. The crystal packing is stabilized by intermolecular C—H...O interactions, generating a chain running along the a axis.

  15. A highly selective fluorescent sensor for Cu{sup 2+} based on 2-(2'-hydroxyphenyl)benzoxazole in a poly(vinyl chloride) matrix

    Energy Technology Data Exchange (ETDEWEB)

    Zhang Xiaobing [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (China); Peng Jing [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (China); He Chunlian [Medical college, Hunan Normal University, Changsha 410006 (China); Shen Guoli [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (China); Yu Ruqin [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (China)]. E-mail: rqyu@hnu.cn

    2006-05-17

    This paper describes a copper selective optical chemical sensor based on static quenching of the fluorescence of 2-(2'-hydroxyphenyl)benzoxazole entrapped in a poly(vinyl chloride) (PVC) membrane. The effect of the composition of the sensing membrane was studied, and experimental conditions were optimized. The sensors exhibit stable response over the concentration range from 4.0 x 10{sup -8} M to 5.0 x 10{sup -5} M Cu{sup 2+} at pH 4.0-6.5, and a high selectivity. The response time for Cu{sup 2+} with concentration {<=}5 x 10{sup -6} M is less than 7 min. The optode can be regenerated using 0.1 M HCl and acetate buffer solution. The sensor has been used for direct measurement of copper content in river water samples with a relative error less than 4% with reference to that obtained by atomic absorption spectrometry.

  16. Responsive mechanism of 2-(2’-hydroxyphenyl)benzoxazole-based two-photon fluorescent probes for zinc and hydroxide ions

    Institute of Scientific and Technical Information of China (English)

    张玉瑾; 张秋月; 丁红娟; 宋秀能; 王传奎

    2015-01-01

    The response theory is used to investigate one-and two-photon absorption (TPA) as well as emission properties of a series of potential zinc ion and pH sensitive materials containing 2-(2’-hydroxyphenyl)benzoxazole (HPBO) end groups. Special emphasis is placed on the evolution of their optical properties upon combining with zinc ions or deprotonation. Calculated results indicate that upon combining with zinc ions or deprotonation, these HPBO derivatives show drastic changes in their one-photon absorption (OPA), emission, and TPA properties. Moreover, mechanisms of the probes are analyzed to be intramolecular charge transfer. These compounds are thus proved to be excellent candidates for two-photon fl uorescent zinc and pH probes.

  17. Heterogeneously porous γ-MnO₂-catalyzed direct oxidative amination of benzoxazole through C-H activation in the presence of O₂.

    Science.gov (United States)

    Pal, Provas; Giri, Arnab Kanti; Singh, Harshvardhan; Ghosh, Subhash Chandra; Panda, Asit Baran

    2014-09-01

    Oxidative amination of azoles through catalytic C-H bond activation is a very important reaction due to the presence of 2-aminoazoles in several biologically active compounds. However, most of the reported methods are performed under homogeneous reaction conditions using excess reagents and additives. Herein, we report the heterogeneous, porous γ-MnO2-catalyzed direct amination of benzoxazole with wide range of primary and secondary amines. The amination was carried under mild reaction conditions and using molecular oxygen as a green oxidant, without any additives. The catalyst can easily be separated by filtration and reused several times without a significant loss of its catalytic performance. Of note, the reaction tolerates a functional group such as alcohol, thus indicating the broad applicability of this reaction.

  18. 3-苯并嚼唑-6-甲酰基咔唑的合成%Synthesis of 3-benzoxazole-6-formyl Carbazole

    Institute of Scientific and Technical Information of China (English)

    杨旭; 费学宁; 谷迎春; 李超

    2011-01-01

    Two novel 3-benzoxazole-6-formyl carbazole derivatives were synthesized from carbazole by alkylation, formylation, oxidation of carbazole schiff bases and formylation. The cqmpounds' structures were characterized by 1H NMR and MS and their fluorescent spectra were preliminarily studied.%以咔唑为原料,经过烷基化、甲酰化、咔唑席夫碱氧化、甲酰化,合成了2个3-苯并嗯唑-6-甲酰基咔唑衍生物,其结构经1HNMR和MS表征,并初步研究了其荧光光谱.

  19. Synthesis and biological evaluation of a series of benzoxazole/benzothiazole-containing 2,3-dihydrobenzo[b][1,4]dioxine derivatives as potential antidepressants.

    Science.gov (United States)

    Wang, Songlin; Chen, Yin; Zhao, Song; Xu, Xiangqing; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen

    2014-04-01

    A series of benzoxazole/benzothiazole-2,3-dihydrobenzo[b][1,4]dioxine derivatives (5a-5d and 8a-8j) was synthesized. Compounds were evaluated for binding affinities at the 5-HT1A and 5-HT2A receptors. Antidepressant activities of the compounds were screened using the forced swimming test (FST) and the tail suspension test (TST). The results indicated that the compounds exhibited high affinities for the 5-HT1A and 5-HT2A receptors and showed a marked antidepressant-like activity. Compound 8g exhibited high affinities for the 5-HT1A (Ki=17 nM) and 5-HT2A (Ki=0.71 nM) receptors; it also produced a decrease of the immobility time and exhibited potent antidepressant-like effects in the FST and TST in mice.

  20. Vibrational spectroscopic (FT-IR, FT-Raman, ¹H NMR and UV) investigations and computational study of 5-nitro-2-(4-nitrobenzyl) benzoxazole.

    Science.gov (United States)

    Bhagyasree, J B; Varghese, Hema Tresa; Panicker, C Yohannan; Samuel, Jadu; Van Alsenoy, Christian; Bolelli, Kayhan; Yildiz, Ilkay; Aki, Esin

    2013-02-01

    The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-nitro-2-(4-nitrobenzyl) benzoxazole have been investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of the normal modes of vibrations was done using GAR2PED program. The energy and oscillator strength calculated by time dependent density functional theory almost compliments with experimental findings. Gauge-including atomic orbital (1)H NMR chemical shifts calculations were carried out by using B3LYP functional with 6-31G basis set. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization have been analyzed using NBO analysis. MEP was performed by the DFT method and the predicted infrared intensities and Raman activities have also been reported. The calculated geometrical parameters are in agreement with that of similar derivatives.

  1. 2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: attenuation of hERG binding and improved HDLc-raising efficacy.

    Science.gov (United States)

    Sweis, Ramzi F; Hunt, Julianne A; Sinclair, Peter J; Chen, Ying; Eveland, Suzanne S; Guo, Qiu; Hyland, Sheryl A; Milot, Denise P; Cumiskey, Anne-Marie; Latham, Melanie; Rosa, Raymond; Peterson, Larry; Sparrow, Carl P; Anderson, Matt S

    2011-05-01

    The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Efforts focused on finding suitable replacements for the central piperidine with the aim of reducing hERG binding: a main liability of our benchmark benzoxazole (1a). Replacement of the piperidine with a cyclohexyl group successfully attenuated hERG binding, but was accompanied by reduced in vivo efficacy. The approach of substituting a piperidine moiety with an oxazolidinone also attenuated hERG binding. Further refinement of this latter scaffold via SAR at the pyridine terminus and methyl branching on the oxazolidinone led to compounds 7e and 7f, which raised HDLc by 33 and 27mg/dl, respectively, in our transgenic mouse PD model and without the hERG liability of previous series.

  2. Synthesis, Antibacterial and Antioxidant Evaluation of Novel 1-(5,7-Dichloro-1,3-benzoxazol-2-yl-1H-pyrazolo[3,4-b]quinoline Derivatives

    Directory of Open Access Journals (Sweden)

    N. D. Jayanna

    2013-01-01

    Full Text Available Some novel 1-(5,7-dichloro-1,3-benzoxazol-2-yl-1H-pyrazolo[3,4-b]quinoline derivatives 8(a–f were synthesized by reacting 5,7-dichloro-2-hydrazino-1,3-benzoxazole 4 and substituted-2-chloro-3-quinoline carbaldehydes using p-toluenesulfonic acid (PTSA as a catalyst for the cyclisation. The target molecules have been characterized by IR, 1H NMR, 13C NMR, and mass spectral studies. The synthesized compounds were screened for biological activities, and some of the compounds have exhibited encouraging antibacterial and antioxidant activities. The compounds 8a and 8e showed potent antibacterial activity, whereas the compounds 8e and 8f act as antioxidants.

  3. Experimental and theoretical study of the structures and enthalpies of formation of 3H-1,3-benzoxazole-2-thione, 3H-1,3-benzothiazole-2-thione, and their tautomers.

    Science.gov (United States)

    Roux, Maria Victoria; Temprado, Manuel; Jiménez, Pilar; Foces-Foces, Concepción; Notario, Rafael; Parameswar, Archana R; Demchenko, Alexei V; Chickos, James S; Deakyne, Carol A; Liebman, Joel F

    2010-06-01

    This paper reports an experimental and theoretical study of the structures and standard (p(o) = 0.1 MPa) molar enthalpies of formation of 3H-1,3-benzoxazole-2-thione and 3H-1,3-benzothiazole-2-thione. The enthalpies of combustion and sublimation were measured by rotary bomb combustion calorimetry and the Knudsen effusion technique, and gas-phase enthalpies of formation values at T = 298.15 K of (42.0 +/- 2.7) and (205.5 +/- 3.8) kJ x mol(-1) for 3H-1,3-benzoxazole-2-thione and 3H-1,3-benzothiazole-2-thione, respectively, were determined. G3-calculated enthalpies of formation are in excellent agreement with the experimental values. The present work discusses the question of tautomerism explicitly for both compounds and compares the energetics of all the related species. A comparison of the theoretical results with the structural data is also reported.

  4. Reactive, spectroscopic and antimicrobial assessments of 5-[(4-methylphenyl) acetamido]-2-(4-tert-butylphenyl)benzoxazole: Combined experimental and computational study

    Science.gov (United States)

    Mary, Y. Sheena; Alzoman, Nourah Z.; Menon, Vidya V.; Al-Abdullah, Ebtehal S.; El-Emam, Ali A.; Panicker, C. Yohannan; Temiz-Arpaci, Ozlem; Armaković, Stevan; Armaković, Sanja J.; Van Alsenoy, C.

    2017-01-01

    The synthesis, FT-IR, FT-Raman and NMR spectral analysis of an antimicrobial active benzoxazole derivative, 5-[(4-methylphenyl)acetamido]-2-(4-tert-butylphenyl) benzoxazole (MPATB) is reported. The localization of HOMO, LUMO plots in the title compound over the title molecule shows the charge transfer in the molecular system through the conjugated paths.The electrophilic and nucleophilic sites are revealed from the molecular electrostatic potential map. The first hyperpolarizability of the title compound is greater than that of the standard nonlinear optical material urea and the title compound and its derivatives are good objects for further research in nonlinear optical analysis. Molecule sites prone to electrophilic attacks have been detected by calculation of average local ionization energies, while calculations of Fukui functions have provided additional information about the local reactivity properties. Bond dissociation energies have been calculated in order to investigate autoxidation possibilities of the title molecule, as well as to determine the weakest bonds and therefore the sites where process of degradation could start. Reactive properties with water have been investigated by molecular dynamics simulations and calculations of radial distribution functions. The compound possessed broad spectrum activity against all of the tested Gram-positive and Gram-negative bacteria and yeasts, their minimum inhibitory concentrations ranging between 8 and 128 μg/ml. The compound exhibited significant antifungal activity (64 μg/ml) against Candida krusei, at same potency with the compared standard drugs fluconazole. The docked title compound forms a stable complex with thymidylate synthase and got a binding affinity value of -8.5 kcal/mol and the title compound can be a lead compound for developing new anti-cancerous drug.

  5. Discovery and optimization of new benzimidazole- and benzoxazole-pyrimidone selective PI3Kβ inhibitors for the treatment of phosphatase and TENsin homologue (PTEN)-deficient cancers.

    Science.gov (United States)

    Certal, Victor; Halley, Frank; Virone-Oddos, Angela; Delorme, Cécile; Karlsson, Andreas; Rak, Alexey; Thompson, Fabienne; Filoche-Rommé, Bruno; El-Ahmad, Youssef; Carry, Jean-Christophe; Abecassis, Pierre-Yves; Lejeune, Pascale; Vincent, Loic; Bonnevaux, Hélène; Nicolas, Jean-Paul; Bertrand, Thomas; Marquette, Jean-Pierre; Michot, Nadine; Benard, Tsiala; Below, Peter; Vade, Isabelle; Chatreaux, Fabienne; Lebourg, Gilles; Pilorge, Fabienne; Angouillant-Boniface, Odile; Louboutin, Audrey; Lengauer, Christoph; Schio, Laurent

    2012-05-24

    Most of the phosphoinositide-3 kinase (PI3K) kinase inhibitors currently in clinical trials for cancer treatment exhibit pan PI3K isoform profiles. Single PI3K isoforms differentially control tumorigenesis, and PI3Kβ has emerged as the isoform involved in the tumorigenicity of PTEN-deficient tumors. Herein we describe the discovery and optimization of a new series of benzimidazole- and benzoxazole-pyrimidones as small molecular mass PI3Kβ-selective inhibitors. Starting with compound 5 obtained from a one-pot reaction via a novel intermediate 1, medicinal chemistry optimization led to the discovery of compound 8, which showed a significant activity and selectivity for PI3Kβ and adequate in vitro pharmacokinetic properties. The X-ray costructure of compound 8 in PI3Kδ showed key interactions and structural features supporting the observed PI3Kβ isoform selectivity. Compound 8 achieved sustained target modulation and tumor growth delay at well tolerated doses when administered orally to SCID mice implanted with PTEN-deficient human tumor xenografts.

  6. Environment-sensitive benzoxazole based fluorescein derivatives: Synthesis and application to the design of ON–OFF fluorescent chemosensors for microenvironment

    Energy Technology Data Exchange (ETDEWEB)

    Patil, Vikas; Padalkar, Vikas; Sekar, Nagaiyan, E-mail: nethi.sekar@gmail.com

    2015-02-15

    The intermediate 2-(2′, 4,-dihydroxyphenyl) benzoxazole was used for the synthesis of substituted fluorescein derivatives. Fluorescence behavior of the synthesized fluorescein derivatives was studied under different microenvironments like pH, viscosity, surfactant sodium dodecyl sulfate (SDS) and protein Bovine Serum Albumin (BSA). Further, the fluorescence of these molecules was used for the detection of blood sample. Photophysical properties show that all the fluorescent compounds are very sensitive to pH, and in basic medium these compounds show hyper chromic shift. These compounds are also sensitive to the viscosity of the medium. All the compounds are characterized by FT-IR, H NMR and mass spectral analysis. - Highlights: • Synthesized novel ESIPT inspired compounds which are unknown to this date, synthesis route is very easy. • Existing fluorescein compounds show single absorption in UV region having restricted applications are overcome by introducing ESIPT unit in fluorescein core. • First and unique study of fluorescein compounds having pH sensitive dual absorption–emission characteristics. • Relative fluorescence quantum yield of fluorescein derivatives was investigated.

  7. Preparation of highly conjugated water-dispersible graphene-butyric acid for the enhancement of electron transfer within polyamic acid-benzoxazole: potential applications in electrochemical sensing.

    Science.gov (United States)

    Chen, Hsiao-Chien; Chen, Yen-Hsuan; Chen, Shi-Liang; Chern, Yaw-Terng; Tsai, Rung-Ywan; Hua, Mu-Yi

    2013-08-15

    To break through the long time and complex procedures for the preparation of highly conjugated reduced graphene oxide (r-GO) in developing electrochemical sensor, a time-saving and simple method is investigated in this study. One novel step of the exfoliated accompanying carboxylated graphene sheet from pristine is achieved via Friedel-Crafts acylation. By electrophilic aromatic substitution, the succinic anhydride ring is opened and attaches covalently to the graphene sheet (Gs) to form exfoliated graphene with grafted 1-one-butyric acid (Gs-BA). The grafting chain converts anions in aqueous solution to maintain Gs-BA in a stable dispersion and noticeably decreases the π-π stacking of the exfoliated Gs during the drying process. The analytical results of the absorption spectroscopy demonstrate that the conjugation of Gs-BA is not significantly destroyed by this chemical modification; Gs-BA retains the Gs electrical properties favorable for developing electrochemical sensors. When polyamic acid-benzoxazole (PAA-BO), a hydrogen peroxide (H₂O₂)-sensitive probe, hybridizes with Gs-BA to form Gs-BA-PAA-BO, the electron transfer rate relating to the response time improves markedly from 1.09 s(-1) to 38.8 s(-1). Additionally, it offers a high performance for H₂O₂ sensing in terms of sensitivity and response time, making this method applicable for developing glucose and choline biosensors.

  8. White emitters by tuning the excited-state intramolecular proton-transfer fluorescence emission in 2-(2'-hydroxybenzofuran)benzoxazole dyes.

    Science.gov (United States)

    Benelhadj, Karima; Muzuzu, Wenziz; Massue, Julien; Retailleau, Pascal; Charaf-Eddin, Azzam; Laurent, Adèle D; Jacquemin, Denis; Ulrich, Gilles; Ziessel, Raymond

    2014-09-26

    The synthesis, structural, and photophysical properties of a new series of original dyes based on 2-(2'-hydroxybenzofuran)benzoxazole (HBBO) is reported. Upon photoexcitation, these dyes exhibit intense dual fluorescence with contribution from the enol (E*) and the keto (K*) emission, with K* being formed through excited-state intramolecular proton transfer (ESIPT). We show that the ratio of emission intensity E*/K* can be fine-tuned by judiciously decorating the molecular core with electron-donating or -attracting substituents. Push-pull dyes 9 and 10 functionalized by a strong donor (nNBu2 ) and a strong acceptor group (CF3 and CN, respectively) exhibit intense dual emission, particularly in apolar solvents such as cyclohexane in which the maximum wavelength of the two bands is the more strongly separated. Moreover, all dyes exhibit strong solid-state dual emission in a KBr matrix and polymer films with enhanced quantum yields reaching up to 54 %. A wise selection of substituents led to white emission both in solution and in the solid state. Finally, these experimental results were analyzed by time-dependent density functional theory (TD-DFT) calculations, which confirm that, on the one hand, only E* and K* emission are present (no rotamer) and, on the other hand, the relative free energies of the two tautomers in the excited state guide the ratio of the E*/K* emission intensities.

  9. TD-DFT study on fluoride-sensing mechanism of 2-(2'-phenylureaphenyl)benzoxazole: the way to inhibit the ESIPT process.

    Science.gov (United States)

    Li, Guang-Yue; Chu, Tianshu

    2011-12-14

    The fluoride-sensing mechanism of the sensor 2-(2'-phenylurea-phenyl)benzoxazole (PUBO) has been investigated by means of the TD-DFT method. The present theoretical study indicates that there is an excited-state intramolecular proton transfer (ESIPT) process in the sensor PUBO. The added fluoride anion could capture the proton in the free N-H moiety instead of the hydrogen-bonding one. The experimental UV/Vis and fluorescence spectra (J. Org. Chem. 2007, 72, 62) are well reproduced by the calculated vertical excitation energies in the ground state and the first singlet excited state. For example, the calculated emission wavelength of PUBO at 534 nm is very close to the fluorescence band at 554 nm. Furthermore, we theoretically confirmed that the added fluoride anions could inhibit the ESIPT process in PUBO. But different from the classical ESIPT-inhibition mechanism, the ESIPT process in the sensor PUBO is inhibited by the high energy barrier of its deprotonated form rather than by the absence of the transferred proton.

  10. Spectroscopic characterizations of non-amphiphilic 2-(4-biphenylyl)-6-phenyl benzoxazole molecules at the air-water interface and in Langmuir-Blodgett films

    Energy Technology Data Exchange (ETDEWEB)

    Hussain, S.A. [Department of Physics, Tripura University, Suryamaninagar, Agartala: 799130 Tripura (India); Deb, S. [Department of Physics, Tripura University, Suryamaninagar, Agartala: 799130 Tripura (India); Bhattacharjee, D. [Department of Physics, Tripura University, Suryamaninagar, Agartala: 799130 Tripura (India)]. E-mail: tuphysic@sancharnet.in

    2005-09-15

    This communication reports about the successful incorporation of a well-known non-amphiphilic derivative of oxazole chromophore 2-(4-biphenylyl)-6-phenyl benzoxazole abbreviated as PBBO, in Langmuir-Blodgett films when mixed with stearic acid (SA) as well as also an inert polymer matrix polymethylmethacrylate (PMMA). The surface pressure versus area per molecule isotherms of the Langmuir films of PBBO mixed with PMMA or SA at different mole fractions reveal that the area per molecule decreases consistently with increasing mole fractions of PBBO. Area per molecule versus mole fraction curve shows that the experimental data points coincide with the ideality curve predicted by the additivity rule, which leads to the conclusion of either ideal mixing or complete demixing of the binary components. The UV-vis absorption and fluorescence spectroscopic studies of mixed LB films of PBBO reveal the nature of complete demixing of the binary components of the sample molecules (PBBO) and PMMA or SA molecules. This complete demixing leads to the formation of clusters and aggregates of PBBO molecules in Langmuir and Langmuir-Blodgett films. J-type aggregates of PBBO molecules in LB films have been confirmed by UV-vis absorption spectroscopic study. Aggregation of PBBO molecules in LB films giving rise to excimeric emission has been demonstrated by fluorescence spectroscopic study. Excitation spectroscopic study clearly confirmed the presence of excimeric sites.

  11. Excited state intramolecular proton transfer (ESIPT) in 2-(2'-hydroxyphenyl)benzoxazole and its naphthalene-fused analogs: a TD-DFT quantum chemical study.

    Science.gov (United States)

    Roohi, Hossein; Hejazi, Fahimeh; Mohtamedifar, Nafiseh; Jahantab, Mahjobeh

    2014-01-24

    The intramolecular proton transfer reactions in 2-(2'-hydroxyphenyl)benzoxazole (HBO) and its naphthalene-fused analogs, (HNB1-3) in both S0 and S1 states at the PBE1PBE/6-311++G(2d,2p) level of theory in the gas phase and water have been investigated to find the effects of extension of aromaticity on the intramolecular proton transfer and photophysical properties. The results show that the ground state intramolecular proton transfer (GSIPT) in the studied species is impossible. Excited states potential energy surface calculations support the existence of ESIPT process. Structural parameters, relative energy of isomers, H-bonding energy, adsorption and emission bands, vertical excitation and emission energies, oscillator strength, fluorescence rate constant, dipole moment, atomic charges and electron density at critical points were calculated. Orbital analysis shows that vertical S0→S1 transition in the studied molecules corresponds essentially to the excitation from HOMO (π) to LUMO (π(*)). The potential of HNB2 molecule as an emissive and electron transport material in designing improved organic white light emitting diodes is predicted in this work. Our calculations are also supported by the experimental observations.

  12. Excited-state intramolecular hydrogen bonding of compounds based on 2-(2-hydroxyphenyl)-1,3-benzoxazole in solution: a TDDFT study.

    Science.gov (United States)

    Li, Hui; Liu, Yufang; Yang, Yonggang; Yang, Dapeng; Sun, Jinfeng

    2014-12-10

    The excited-state properties of intramolecular hydrogen bonding in the compounds based on 2-(2-hydroxyphenyl)-1,3-benzoxazole (6 and its tautomers 6a and 6b) have been investigated using theoretical methods. According to the geometric optimization and IR spectra in the ground and excited states calculated by density functional theory (DFT) and time-dependent DFT (TD-DFT) methods respectively, the type of intramolecular hydrogen bonding N⋯HO in 6 and 6a is demonstrated to be significantly strengthened, while NH⋯O in the tautomers 6a and 6b are proved to be sharply weakened upon excitation to excited state S1. The calculated absorption peaks of 6 are in good accordance with the experimental results. Moreover, other compounds based on 6 that R1 and R2 are both substituted as well as that only R1 is substituted are investigated to understand the effect of substituent on intramolecular hydrogen bonding. It is found that the hydrogen bond strength can be controlled by the inductive field effect of the substituent. In addition, the intramolecular charge transfers (ICT) of the S1 state for 6 and its tautomers 6a and 6b were theoretically investigated by analyses of molecular orbital.

  13. Probing ligand-binding modes and binding mechanisms of benzoxazole-based amide inhibitors with soluble epoxide hydrolase by molecular docking and molecular dynamics simulation.

    Science.gov (United States)

    Chen, Hang; Zhang, Ying; Li, Liang; Han, Ju-Guang

    2012-08-30

    Soluble epoxide hydrolase (sEH) has become a new therapeutic target for treating a variety of human diseases. The inhibition of human sEH hydrolase activity was studied by molecular docking and molecular dynamics (MD) simulation techniques. A set of six benzoxazole-based amide inhibitors binding to sEH has been studied through molecular docking, MD simulation, free energy calculations, and energy decomposition analysis. On the basis of molecular mechanics-generalized Born/surface area (MM-GB/SA) computation and normal-mode analysis (NMA), the obtained results indicate that the rank of calculated binding free energies (ΔΔGTOT) of these inhibitors is in excellent agreement with that of experimental bioactivity data (IC50). The correlation coefficient (r(2)) between the predicted ΔΔGTOT and IC50 is 0.88. van der Waals energies are the largest component of the total energies, and the entropy changes play an indispensable role in determining the ΔΔGTOT. Rational binding modes were discussed and determined by the docking results and binding free energies. The free energy decomposition of each residue reveals that the residue Trp334 dominates the most binding free energies among all residues and that the activities for these molecules to the sEH are not decided by hydrogen bonds or a certain residue but by the common effect of multiple side chains in the active site.

  14. Moderate modulation of disease in the G93A model of ALS by the compound 2-(2-hydroxyphenyl)-benzoxazole (HBX).

    Science.gov (United States)

    Evans, Teresa M; Bhattacharya, Arunabh; Shi, Yun; Qi, Wenbo; Block, Travis J; Chaudhuri, Asish; Chaudhuri, Alakananda Ray; Hawker, Kara; Van Remmen, Holly

    2016-06-15

    Amyotrophic lateral sclerosis (ALS) is a progressive and fatal neurological disease characterized by degeneration and death of motor neurons. Aberrant protein aggregation and oxidative stress are implicated in the etiology of ALS; thus preventing propagation of early aggregation events and oxidative damage could be an effective therapy. We tested the effect of dietary supplementation (initiated 40 days of age) with 2-(2-hydroxyphenyl)-benzoxazole (HBX), a compound with metal chelator and anti-aggregation properties, on disease onset, progression and lifespan in the G93A mouse model of ALS. Tests were not sufficiently powerful to detect any change to survival distribution of mice treated with HBX. However, the disease onset was delayed and max lifespan was increased in the treatment group. Additionally, disease progression was moderated as shown by reduced neuromuscular denervation measured by repetitive nerve stimulation. F2-isoprostanes, a marker of oxidative damage, are elevated in skeletal muscle from G93A mice at onset and this increase is prevented in HBX fed G93A mice. Furthermore, HBX treatment reduced mutant SOD1 protein aggregation in whole spinal cord of G93A mice at disease onset. Overall, our data suggests that HBX may be able to improve the degenerative symptoms of ALS through the prevention of oxidative damage and protein aggregation. Further studies are needed to uncover the mechanistic effects of HBX in ameliorating ALS pathology.

  15. 微波促进下2-取代苯并噁唑类化合物合成研究%Microwave Irradiation Promoted Synthesis of 2-Substituted Benzoxazoles

    Institute of Scientific and Technical Information of China (English)

    郭强; 杨雅芬; 程彪; 张峰涛; 范学森

    2013-01-01

    研究了离子液体介质中、微波辐射促进下邻氨基苯酚与醛的缩合反应,并利用该反应合成了一系列2-取代苯并号唑.与文献方法相比,所报道的新方法具有反应速度快、收率高以及对环境友好等诸多优势,从而为2-取代苯并噁唑类化合物的合成提供了一条新途径.%A clean and efficient synthesis of 2-substituted benzoxazoles through tandem reactions of 2-aminophenols and aldehydes mediated with [bmim][BF4] under MWI has been developed.Compared with literature methods toward 2-substituted benzoxazoles,the synthetic strategy presented in the paper has such advantages as enhanced reaction rate,high yield and environmental benigncy.

  16. Molecular recognition between ligands and nucleic acids: Novel pyridine- and benzoxazole-containing agents related to Hoechst 33258 that exhibit altered DNA sequence specificity deduced from footprinting analysis and spectroscopic studies

    Energy Technology Data Exchange (ETDEWEB)

    Bathini, Y.; Rao, K.E.; Shea, R.G.; Lown, J.W. (Univ. of Alberta, Edmonton (Canada))

    The syntheses of certain analogues of the DNA minor groove binding agent Hoechst 33258 designed to exhibit altered sequence recognition are described. The structural modifications include the following: substitution of pyridine for the benzene ring of the benzimidazole moiety, replacement of one benzimidazole unit by a benzoxazole in the two possible orientations with respect to the DNA receptor, and a synthesis of 2,2{prime}-m-phenylenebis(6-(4-methyl-1-piperazinyl)benzimidazole). Sequence recognition of these agents on a HindIII/EcoRI fragment of pBR322 DNA was determined by MPE footprinting procedures. Some of the analogues exhibited altered DNA sequence preference compared with Hoechst 33258. In particular, a structure bearing a benzoxazole moiety with the oxygen oriented inward to the minor groove together with an inward-directed pyridine nitrogen appears to confer the property of recognition of a GC base pair within the binding sequence. The possible factors, structural, stereochemical, and electrostatic, contributing to the altered DNA sequence recognition properties are discussed.

  17. Revealing the ionization ability of binding site I of human serum albumin using 2-(2'-hydroxyphenyl)benzoxazole as a pH sensitive probe.

    Science.gov (United States)

    Abou-Zied, Osama K

    2012-02-28

    The ability of site I of human serum albumin (HSA) to bind medium sized molecules is important for the distribution, metabolism, and efficacy of many drugs. Herein, we show that this binding site has the ionization ability that may alter the drug structure during the process of its delivery. We reveal this ability by employing 2-(2'-hydroxyphenyl)benzoxazole (HBO) as a pH sensitive probe. Binding of HBO in site I is studied here at physiological pH 7.2 using steady-state and lifetime spectroscopic measurements, molecular docking and molecular dynamics (MD) simulation methods. The complex photophysics of HBO and the unique fluorescence signature of its anionic form indicate that, upon binding with HSA, the molecule exists in equilibrium between the anionic and the syn-keto forms. The position of HBO inside the binding site was determined experimentally by measuring the fluorescence quenching of W214, the sole tryptophan residue in HSA. The ionization degree of HBO inside the binding site was estimated to be close to the ionization degree of HBO in an aqueous solution of pH 10. This was concluded by comparing the fluorescence behavior of bound HBO to that of HBO in different solvents and in aqueous solutions of different pH values. Molecular docking and MD simulations show that HBO binds in site I close to W214, confirming the experimental results, and pinpoint the dominant role of hydrophobic interactions in the binding site. The formation of the anionic form is proposed to be due to through-space interaction between the OH group of HBO and both R222 and I290 with a binding mode similar to that of warfarin in site I. Comparison of the results with those of HBO mixed with key amino acids in solution indicates the importance of through-space interaction in the formation of the anion, similar to enzymatic reactions.

  18. Synthesis, vibrational spectroscopic investigations, molecular docking, antibacterial studies and molecular dynamics study of 5-[(4-nitrophenyl)acetamido]-2-(4-tert-butylphenyl)benzoxazole

    Science.gov (United States)

    Sheena Mary, Y.; Al-Shehri, Mona M.; Jalaja, K.; Al-Omary, Fatmah A. M.; El-Emam, Ali A.; Yohannan Panicker, C.; Armaković, Stevan; Armaković, Sanja J.; Temiz-Arpaci, Ozlem; Van Alsenoy, C.

    2017-04-01

    Antimicrobial active 5-[(4-nitrophenyl)acetamido]-2-(4-tert-butylphenyl)benzoxazole (NATPB) was synthesized and observed IR, Raman bands are compared with the theoretically predicted wave numbers. In the IR spectrum the NH stretching wave number splits into a doublet with a noted difference and is red shifted from the computed value, which indicates the weakening of NH bond resulting in proton transfer to the neighbouring oxygen atom. The HOMO-LUMO plots reveal the charge transfer in the molecular system through the conjugated paths. The electrophilic and nucleophilic reactive sites are identified from the MEP plot. Mapping of average local ionization energy (ALIE) values to the electron density surface served us as a tool for prediction of molecule sites possibly prone to electrophilic attacks. Other important reactive centres of the title molecule were detected by calculations of Fukui functions. Calculations of bond dissociation energies (BDE) for hydrogen abstraction were used in order to assess whether the NATPB molecules is prone to autoxidation mechanism or not, while BDE of the remaining single acyclic bonds were used in order to determine the weakest bond. Interaction properties with water were investigated by molecular dynamics (MD) simulations and calculations of radial distribution functions (RDFs). The compound possessed broad spectrum activity against all of the tested Gram-positive and Gram-negative bacteria and yeasts, their minimum inhibitory concentrations (MICs) ranging between 32 and 128 μg/ml. The compound exhibited significant antibacterial activity (32 μg/ml) against an antibiotic resistant E. faecalis isolate, at same potency with the compared standard drugs vancomycin and gentamycin sulfate. The molecular docking studies show that the compound might exhibit inhibitory activity against CDK inhibitors.

  19. Comparison of experimental and DFT-calculated NMR chemical shifts of 2-amino and 2-hydroxyl substituted phenyl benzimidazoles, benzoxazoles and benzothiazoles in four solvents using the IEF-PCM solvation model.

    Science.gov (United States)

    Pierens, Gregory K; Venkatachalam, T K; Reutens, David C

    2016-04-01

    A comparative study of experimental and calculated NMR chemical shifts of six compounds comprising 2-amino and 2-hydroxy phenyl benzoxazoles/benzothiazoles/benzimidazoles in four solvents is reported. The benzimidazoles showed interesting spectral characteristics, which are discussed. The proton and carbon chemical shifts were similar for all solvents. The largest chemical shift deviations were observed in benzene. The chemical shifts were calculated with density functional theory using a suite of four functionals and basis set combinations. The calculated chemical shifts revealed a good match to the experimentally observed values in most of the solvents. The mean absolute error was used as the primary metric. The use of an additional metric is suggested, which is based on the order of chemical shifts. The DP4 probability measures were also used to compare the experimental and calculated chemical shifts for each compound in the four solvents. Copyright © 2015 John Wiley & Sons, Ltd.

  20. Synthesis of 2-Substituted Aryl Benzoxazoles Catalyzed by Ammonium Metavanadate%偏钒酸铵催化合成2-芳基取代苯并噁唑

    Institute of Scientific and Technical Information of China (English)

    肖立伟

    2011-01-01

    在偏钒酸铵催化下,以2-氨基苯酚和芳醛为原料、乙醇为溶剂,在室温下合成了一系列2-芳基取代苯并噁唑类化合物.该方法具有操作简便、反应条件温和、产率高等优点.%Ammonium metavanadate was found to be a practical catalyst for synthesizing 2-substituted aryl benzoxazoles, starting from 2-amino-phenol and aromatic aldehydes in ethanol at room temperature.The method was proved to be simple and convenient, and the product was isolated with excellent yields.

  1. A DFT/TD DFT study of the structure and spectroscopic properties of 5-methyl-2-(8-quinolinyl)benzoxazole and its complexes with Zn(II) ion.

    Science.gov (United States)

    Guzow, Katarzyna; Milewska, Magda; Czaplewski, Cezary; Wiczk, Wiesław

    2010-02-01

    The structure and spectroscopic properties of 5-methyl-2-(8-quinolinyl)benzoxazole and its complexes with Zn(II) ion were studied using a DFT and TD DFT methods with def2-TZVP basis set. It was shown that the type of functional used (B3-LYP or pbe0) implemented in TURBOMOLE package does not have essential influence on the geometry (small differences in bond length, valence and dihedral angles) of studied compounds in both ground and excited states. However, significant differences were obtained for the position of vertical absorption and emission transition but not for the oscillator strength of transition. Application of pbe0 functional seems to reproduce better the experimental spectrum.

  2. Synthesis and Properties of Soluble Polyimide with Benzoxazole Pendent Group%含苯并噁唑侧基可溶性聚酰亚胺的合成与性能

    Institute of Scientific and Technical Information of China (English)

    鲁东奎; 曾科; 武迪蒙; 李黎; 高帅; 郭乔; 林淦; 杨刚

    2011-01-01

    A novel soluble polyimide with benzoxazole pendent group (PIBO) was successfully synthesized.Compared with the corresponding unmodified polyimide ( PIMA), the solubility of PIMA was maintained and the thermal property of PIBO was enhanced.DSC study showed the glass transition temperature of polyimide increased from 219 ℃ to 260 ℃.%合成出了一种含苯并噁唑侧基可溶性的聚酰亚胺(PIBO),并和相应的不含侧基的聚酰亚胺(PIMA)做了对比:实验数据表明,PIBO在保持PIMA良好溶解性的同时,其热稳定性得到了提高,玻璃化转变温度(Tg)由219℃提高到了260℃.

  3. Design of new arylamino-2-ethane-1,1-diyl- and benzoxazole-2-methylene-bisphosphonates vs cytotoxicity and chronic inflammation diseases. From hydrophobicity prediction to synthesis and biological evaluation.

    Science.gov (United States)

    Abdou, Wafaa M; Barghash, Reham F; Sediek, Ashraf A

    2012-11-01

    A general synthetic approach to two new series of methylenebisphosphonates: arylamino-2-ethane-1,1-diyl- and benzoxazole-2-methylenebisphosphonates is presented. Acid hydrolysis of selected BPs was undertaken to give the corresponding bisphosphonic acid (BP-acid). Next, the prediction of the permeability (hydrophobicity) of the target compounds was measured, by a combination of RP-HPLC and computational techniques, to study the capacity of transporting the molecule through cellular membranes. Cytotoxicity/growth inhibition of 50% (GI(50), mg/L) and antichronic inflammation properties of the products were evaluated. Later on, a comparison of the pharmacological results with water-octanol partition coefficients (log K(OW)) of the compounds was also reported.

  4. Paliperidone: 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-ylpiperidin-1-yl]ethyl}-9-hydroxy-2-methyl-1,6,7,8,9,9a-hexahydropyrido[1,2-a]pyrimidin-4-one

    Directory of Open Access Journals (Sweden)

    Richard Betz

    2011-11-01

    Full Text Available The title compound (also known as 9-hydroxyrisperidone, C23H27FN4O3, is a heterocyclic compound with manifold pharmacological properties. The hydroxy group shows disorder over two positions, with site-occupancy factors of 0.856 (2 and 0.144 (2. The piperidine ring adopts a chair conformation, while the annulated ring bearing the hydroxy group is present in a half-chair conformation. Classical O—H...O hydrogen bonds as well as C—H...N contacts connect the molecules into undulating sheets lying perpendicular to the crystallographic b axis. The shortest centroid–centroid distance between two centers of gravity is 3.5867 (8 Å and is apparent between the benzoxazole moiety and the six-membered ring bearing the keto substituent.

  5. The direct arylation of benzoxazoles with aryl bromides cocatalyzed by Pd(OAc)2 and CuI%Pd(OAc)2/CuI共催化杂环C—H键与芳基溴的直接芳基化反应研究

    Institute of Scientific and Technical Information of China (English)

    颜雪明; 肖新荣; 谭倪

    2012-01-01

    研究开发了一个实用高效的Pd(OAc)2/Cul共催化体系,只需在1% Pd(OAc)2,10% CuI,0.5 mol PPh3配 体存在下,苯并唑类杂环与各种芳基溴的直接芳基化反应就能够在温和的反应条件下顺利进行,并得到良好的收率.%A practical,efficient Pd(OAc)2/CuI cocatalytic system has been developed. With only 1% Pd(OAc)2,10% CuI,and 0. 5 mol of inexpensive PPh3 as ligand,the direct arylation of benzoxazoles with aryl bromides could be performed smoothly in mild condition, affording the desired arylated benzoxazoles in good yields.

  6. 对苯撑二(4-氨基苯并恶唑)合成工艺的正交试验%The Orthogonal Test of Synthesizing Poly p(4-Amino Benzoxazole)

    Institute of Scientific and Technical Information of China (English)

    王兴利; 于洪艳

    2012-01-01

    The poly p (4-amino benzoxazole) was synthesized with using terephthalic acid and 2,4-diaminophenol chloride as raw materials. The effects of molar ratio of reactants, reaction time and temperature and catalyst dosage on the yield were investigated by orthogonal experiments. The optimum conditions for reaction were obtained as follows: n(2,4-diaminophenol chloride):n(terephthalic acid)=2.1, the reaction time was 7h, the reaction temperature was 210℃, n(polyphosphoric acid):n(terephthaiic acid)=1.5. And the yield of poly p(4-amino benzoxazole) reached over 87%. The purity of product was above 99.4%.%用对苯二甲酸、2,4-二氨基苯酚盐酸盐为原料合成了对苯撑二(4-氨基苯并恶唑).采用正交试验方法讨论了原料配比、反应时间、反应温度和催化剂的用量对产品收率的影响,并得出了优选反应工艺条件为:物料配比为n(2,4-二氨基苯酚盐酸盐)∶n(对苯二甲酸)=2.1;反应时间为7h;反应温度为210℃;n(多聚磷酸)∶n(对苯二甲酸)=1.5,在此条件下产品的收率可以达到87%以上,经精制后产品的纯度可以达到99.4以上.

  7. N-二氯乙酰基-5-氯-2,3-二氢苯并噁唑的合成%Synthesis of N-Dichloroacetyl-5-chloro-2,3-dihydro-benzoxazole

    Institute of Scientific and Technical Information of China (English)

    付颖; 王敏; 叶非

    2012-01-01

    The total synthetic route of using the ring closure and acylation reactions, to synthesize the N-dichloroacetyl-5-chloro-2,3-dihydro-benzoxazole with 2-amino-4-chlorophenol, dichloromethane and dichloroacetyl chloride as raw materials was investigated. The factors affecting the yields of the intermediate 5-chloro-2,3-dihydro-benzoxazole and the title compound N-dichloroacetyl-5-chloro-2,3-dihydro-benzoxazole, such as the polarity of solvent and the species of attaching acid agent used, reaction temperature, stirring time, and the molar ratio of reactants, were studied by orthogonal experiments, and the results were discussed. The optimum experimental conditions for the preparation of the intermediate 5-chloro-2,3-dihydro-benzoxazole were found as following: N,N-dimethylacetamide is used as solvent, reaction temperature used is 90°C, stirring time is 1 h and NaOH is used as attaching acid agent. Under above conditions, the yield of 5-chloro-2,3-dihydro-benzoxazole is 72.6%. The optimum synthetic conditions found for preparing the title compound are as follows: N,N-dimethylacetamide is used as solvent, reaction temperature used is 20~25°C, stirring time is 2 h and the molar ratio of 5-chloro-2,3-dihydro-benzoxazole and dichloroacetyl chloride is 1:1.2; and the yield of the title compound could be 91.8%. The structures of the obtained compounds were characterized by IR, 'H-NMR, 13C-NMR and ultimate analysis. The proposed synthetic route is simple, the reaction conditions are mild and the raw materials are cheap and easy to be obtained.%探索了以廉价的对2-氨基-4-氯苯酚、二氯甲烷和二氯乙酰氯为原料,经环合及酰基化反应获得N-二氯乙酰基-5-氯-2,3-二氢苯并噁唑的全合成路线.利用正交实验设计分别研究了反应过程中溶剂效应、反应温度、搅拌时间、缚酸剂对中间体5-氯-2,3-二氢苯并噁唑产率的影响及反应溶剂、温度、搅拌时间及原料的摩尔比对终产物产率的影响.

  8. Electronic and photophysical properties of 2-(2′-hydroxyphenyl)benzoxazole and its derivatives enhancing in the excited-state intramolecular proton transfer processes: A TD-DFT study on substitution effect

    Energy Technology Data Exchange (ETDEWEB)

    Daengngern, Rathawat; Kungwan, Nawee, E-mail: naweekung@gmail.com

    2015-11-15

    The effect of electron donating and withdrawing substituents on the enol absorption and keto emission spectra of 2-(2′-hydroxyphenyl)benzoxazole (HBO) and its derivatives has been systematically investigated by means of density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. The enol absorption spectra of HBO were simulated by using five different DFTs with various exchange-correlation functions to validate a suitable functional prior to being further used as a method of choice to study the effect of substituents on the spectral characteristics of HBO derivatives. The popular B3LYP (Becke, three-parameter, Lee–Yang–Parr) exchange-correlation functional is found to provide the best desirable result in predicting the absorption spectrum close to experimental data. In the ground state, enol forms of HBO and its derivatives are more stable than those of keto forms, while in the first lowest excited state, keto forms are found to be more stable than their enol forms. Overall, simulated absorption and emission spectra of HBO and its derivatives from TD-B3LYP calculations are in good agreement with the experimental data. For enol, absorption maxima of HBO derivatives having electron-withdrawing groups are red-shift corresponding to their lower HOMO–LUMO energy gaps compared to that of HBO. For keto emission, HBO having electron donating groups (m-MeHBO and MHBO) and withdrawing group (CNHBO) at 4′-position on the phenol fragment as well as electron donating groups (HBOMe and HBOM) at 6-position on the benzoxazole fragment make the position of keto emission peak shift to shorter wavelength (blue-shift). However, HBO derivatives with electron withdrawing groups (HBOF, HBOCl, HBOA and HBOE) at 6-position give redshifted emission compared to the parent compound (HBO). The type of substituent on both 4′- and 6-positions certainly has a pronounced effect on the absorption and emission spectra of HBO derivatives. - Highlights: • Simulated spectra

  9. Influence of Exciplex formation on the electroluminescent properties of dimeric Zn (II) bis-2-(2'-hydroxyphenyl) benzoxazole complex and monomeric Zn (II) 2-(1'-hydroxynaphthyl) benzothiazole complex

    Science.gov (United States)

    Prakash, Sattey; Anand, R. S.; Manoharan, S. Sundar

    2011-10-01

    In this paper we present the factors affecting electroluminescent properties of Zinc complexes of oxazole & thiazole derivatives. Electroluminescent spectra of the Zinc (II) complex of bis-[2-(2'-hydroxyphenyl) benzoxazole], [Zn (HPBO)2]2 and 2-(1'-hydroxynaphthyl) benzothiazole [Zn (HNBT)2] show unusual broadening and shows structural and photophysical similarity with [Zn (HPBT)2]2, a dimeric complex. The [Zn (HPBO)2]2 complex as an emissive layer in the device structure ITO /PEDOT:PSS /TPD (30nm) /[Zn (HPBO)2]2 (60nm) /BCP (6nm) /Ca (3nm) /Al (200nm) shows a broad bluish green emission, with a full width at half maxima (FWHM1˜70nm). The EL spectra is much broader compared to the PL spectra because of exciplex formation at the interfacial region between the emissive layer (EML) & hole transport layer (HTL). We also show the device performance of Zinc 2-(1'-hydroxynaphthyl) benzothiazole [Zn (HNBT)2] complex as emissive layer. Distinctly this device shows a broad greenish yellow emission with a peak maxima at 535nm and 690nm, owing to the exciplex formation between electron transport layer (ETL) and emissive layer (EML), which is in sharp contrast to the exciplex formation across the HTL-EML interface observed for the [Zn (HPBO)2]2 complex.

  10. 基于1-(1′,3′-苯并噁唑-2′-甲基)苯并咪唑的钴(Ⅱ)配合物:晶体结构、弱相互作用和荧光发射光谱%Cobalt(H) Complex Based on 1-(1′ ,3′ -Benzoxazole-2′ -methyl)benzimidazole:Crystal Structure, Weak Interactions and Fluorescent Emission Spectra

    Institute of Scientific and Technical Information of China (English)

    吕世真; 李树娟; 王修光; 柳清湘

    2011-01-01

    配体1-(1′,3′-苯并恶唑-2′-甲基)苯并咪唑(L)是通过苯并咪唑与2-(氯甲基)-1,3-苯并恶唑烷基化制备而来.配体L与CoCl2·2H2O反应得到了配合物[CoCl2L2] (1).配合物1通过π-π堆积作用和C-H…Cl氢键形成了三维超分子框架结构.测定了L和1的荧光发射光谱.%The ligand 1-(1′,3′-benzoxazole-2′-methyl)benzimidazole (L) was prepared from benzimidazole by alkylation with 2-(chloromethyl)-1,3-benzoxazole.Reaction of ligand L with CoCl2 ·2H2O afforded a complex [CoCl2L2] (1).In complex 1,3D supramolecular frameworks were formed through π-π interactions and C-H…Cl hydrogen bonds.The fluorescence emission spectra of L and 1 are described.CCDC:843658.

  11. 苯乙烯基氮氧杂芳烃间的交叉光二聚反应%Cross- photodimerization of 4- (2- phenylethenyl)pyridine,2- (2- phenylethenyl)benzoxazole and 5- phenyl- 2- (2- phenyl- ethenyl) oxazole

    Institute of Scientific and Technical Information of China (English)

    庄俊鹏; 张文勤

    2004-01-01

    用中压汞灯(λ>300nm)照射4-苯乙烯基吡啶、2-苯乙烯基苯并口恶唑和5-苯基-2-苯乙烯基口恶唑三种杂芳基乙烯单体中任意两种的硫酸水溶液,得到三种交叉二聚体.用高效液相色谱跟踪研究了交叉光二聚反应,发现每组反应生成三种光二聚体,其中二种为单体自身的光二聚体,而另外一种是两种不同单体的交叉光二聚体.交叉二聚体通过柱色谱分离得到,其顺式头对尾结构经紫外、红外、氢谱、碳谱和元素分析确定.用紫外光谱和高效液相色谱跟踪研究了交叉光二聚体的稀溶液在低压汞灯(λmax=254nm)照射下的光解反应.研究发现交叉二聚体能够彻底发生光解,首先生成原来的反式单体,所生成的反式单体容易发生异构化而生成顺式单体,最终建立起反顺异构化平衡.%Three cross- photodimers were synthesized by irradiation of each two monomers of 4- (2- phenylethenyl)pyridine,2- (2- phenylethenyl)benzoxazole and 5- phenyl- 2- (2- phenylethenyl)oxazole in H2SO4 solution using medium- pressure Mercury lamp (λ > 300 nm) as light source.The cross- photodimerization was monitored by HPLC titration.The results showed that three photodimers were produced in each reaction,two of them were the self- photodimers and the other one was the cross- photodimer.The cross- photodimers were isolated by column chromatography and their structures with syn- head- to- tail configurations were determined by UV,IR,1H NMR,13C NMR and MS.The photolysis of the cross- photodimer was performed in dilute methanol solution upon the irradiation of low- pressure Mercury lamp (λ =254 nm) and monitored by HPLC and UV titration.It was found that the cross- photodimer was photolyzed into trans- monomers at first,and then the new formed trans- monomers were converted into cis- ones by the trans- cis isomerization.

  12. 用正交实验法优化5-氨基-2-(对氨基苯)苯并(噁)唑的合成工艺%The optimized synthesis method of 5-amino-2-(P-aminophenyl) benzoxazole by orthodoxy design

    Institute of Scientific and Technical Information of China (English)

    孟祥丽; 王鹏; 宋美霞

    2011-01-01

    5-amino-2-(P-aminophenyl) benzoxazole was synthesized by the reacting from 2,4-diaminophenol dihydrochloride and P-aminobenzoic acid in polyphosphoric acid. The synthesis method was investigated by orthodoxy experiment, and got the optimized conditions: the reacting temperature is 200 ℃, the reacting time is 5 h, and the content of P2O5 is 84%. The yield of the product is over 90%. The product was purified by methanol with the high purity over 98%, and the product can be used as a monomer in polymerization.%以2,4-二氨基苯酚盐酸盐和对氨基苯甲酸为原料在多聚磷酸中合成了高纯度的5-氨基-2-(对氨基苯)苯并恶唑.用正交实验设计对该合成方法进行了研究,得出了最优化的反应条件:反应温度为200 ℃,反应时间5 h,P2O5质量分数为84%.产品产率较高,可达90%以上.并对产品的纯化方法进行了改进,用甲醇作为重结晶溶剂,得到的产品纯度达98%以上.产物可作为聚合反应的单体原料.

  13. Novel Thermooxidatively Stable Poly(ether-imide-benzoxazole) and Poly (ester-imide-benzoxazole)

    Science.gov (United States)

    1994-07-15

    INTRODUCTION Wholly aromatic polyimldes (PI), polybenzoxazoles (PBO) and polyesters (PES, Scheme 1) all have high thermal stabilities, and find use In high...strength, high modulus fibers and engineering resins.1*2A4 Drawbacks of these systems are their insolubility and intractability, which cause difficulties...method for the production of PBO films and fibers ." Insolubility is circumvented in polyesters through polycondensations under melt conditions

  14. 2-(2'-吡啶基)苯并噁唑和甘氨酸铜配合物的结构、抑菌活性及与DNA作用%Structure, Antibacterial Activities and DNA Interaction of a Copper(Ⅱ)Complex with 2-(2'-Pyridyl) benzoxazole and Glycinate

    Institute of Scientific and Technical Information of China (English)

    区志镔; 黄山华; 乐学义

    2012-01-01

    A new ternary copper(II) complex: [Cu(PB0)(Gly)(H20)]C104 (PBO=2-(2'-pyridyl) benzoxazole, Gly= glycinate), was synthesized and characterized by elemental analysis, molar conductivity, IR, UV-Vis and single crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pca2t, with the crystal cell parameters: a=1.029 2(2) nm, 6=1.032 9(2) nm, c=1.566 8(3) nm, Z=4,7=1.665 6(6) nm3, Z)c=1.800 g-cm-3, F(000)=916, R1,= 0.042 6, wR2=0.101 3. The complex was assayed against gram-positive (S. aureus, B. subtilis, B. thuringiensis) and gram-negative (X. oryzae, Salmonella, E. coil) bacteria by doubling dilutions method, and the interaction of the complex to DNA was investigated by electronic absorption spectroscopy, fluorescence spectroscopy, and viscosity measurement. The results show that the complex has good antibacterial activities and can bind to DNA by intercalative mode. CCDC: 852991.%本文以2-(2'-吡啶基)苯并噁唑、甘氨酸和高氯酸铜(Ⅱ)为原料合成了新的三元配合物:[Cu(PBO)(Gly)(H2O)]ClO4(PBO=2-(2'-吡啶基)苯并噁唑,Gly=甘氨酸根).应用元素分析、红外光谱、紫外可见光谱、摩尔电导率等方法对配合物进行了表征.X-射线单晶衍射测得该配合物晶体属正交晶系,Pca21空间群,晶胞参数:a=1.029 2(2) nm,b=1.032 9(2) nm,c=1.566 8(3) nm;Z=4,V=1.665 6(6) nm3,Dc=1.800 g·cm-3,F(000)=916.最终偏离因子:R1=0.042 6,wR2=0.101 3.利用试管二倍稀释法测定了配合物的抗菌活性,通过电子吸收光谱、荧光光谱和粘度测定研究了配合物与DNA的作用.结果表明,与2-(2 '-吡啶基)苯并噁唑相比较,该配合物对枯草杆菌(B.subtilis,G+),金黄色葡萄球菌(S.aureus,G+),苏云金芽孢杆菌(B.thuringiensis,G+),水稻条斑病细菌(X.oryzae,G-),大肠杆菌(E.coil,G-)和沙门氏杆菌(Salmonella,G-)具有良好的抑制活性,并且以插入方式与DNA作用.

  15. Synthesis and Screening of Fluoro Substituted Pyrazolyl Benzoxazoles

    Directory of Open Access Journals (Sweden)

    R. K. Jadhav

    2015-06-01

    Full Text Available A series of 3-Formylchromone 1 was reacted with 1-(4-(4-fluorophenylthiazol-2-ylhydrazine 2 to get (1-(4-(4-fluorophenylthiazol-2-yl-1H-pyrazol-4-yl(2-hydroxyphenyl methanone 3 which on reaction with hydroxylamine hydrochloride given methanone oxime 4 and 4 on treatment with POCl3 formed 2-(1-(4-(4-fluorophenylthiazol-2-yl-1H-pyrazol-4-ylbenzo[d]oxazole 5. The structures of synthesized compounds were confirmed by spectral analysis further they were screened for their biological activity.

  16. Fluorometric determination of beryllium with 2-(o-hydroxylphenyl)benzoxazole

    Energy Technology Data Exchange (ETDEWEB)

    Gladilovich, D.B.; Stolyarov, K.P.

    1985-09-01

    According to the authors, of great interest for the fluorometric determination of small quantities of beryllium is 2-(o-hydroxyphenyl)benzthiazole (HPBT). In this work, 2-(o-hydroxyphenyl)benzoaxzole (HPBO), which is an analog of HPBT and differs from it in that the sulfur atom in the heterocyclic portion of the molecule is replaced by an oxygen atom, is proposed as a reagent for the fluorometric determination of beryllium. The fluorescent reaction of HPBO with beryllium is studied in this paper, in addition to the selection of the optimum conditions for the determination and the development of a procedure for the analysis of complex objects on this basis. The reaction proceeds in aqueous ethanol medium at pH 7.2-7.5. The limit of detection is 0.6 ng/ml. Methods have been developed for the determination of 10/sup -2/% beryllium in alloys based on copper and 10/sup -3/-10/sup -4/% in standard samples of silicate rocks.

  17. 5-Iodo-3-phenyl-2,1-benzoxazole.

    Science.gov (United States)

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

    2013-04-01

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

  18. 3-Benzyl-5-methyl-1,2-benzoxazole 2-oxide

    Directory of Open Access Journals (Sweden)

    G. Anuradha

    2012-10-01

    Full Text Available In the title compound, C15H13NO2, the isoxazole unit and the attached benzene ring are almost coplanar, making a dihedral angle of 1.42 (8°. The benzyl ring is inclined to the isoxazole ring by 74.19 (8° and is in a +sc conformation with respect to the benzisoxazole unit. In the crystal, C—H...O hydrogen bonds link the molecules, forming zigzag chains propagating along the b axis. There are also π–π interactions present involving the isoxazole and benzyl rings [centroid–centroid distance = 3.5209 (10 Å], and C—H...π interactions involving the benzene ring of the benzoisoxazole unit and the methylene bridging group.

  19. 3-Chloromethyl-6,7-dimethyl-1,2-benzoxazole

    Directory of Open Access Journals (Sweden)

    M. Kayalvizhi

    2012-10-01

    Full Text Available In the title compound, C10H10ClNO, the benzoisoxazole ring is almost planar (r.m.s. deviation = 0.0121 Å and the chloro substituent in the side chain is anticlinal relative to the N—C bond of the isoxazole ring. In the crystal, adjacent molecules are linked via a pair of weak C—H...N hydrogen bonds, forming dimers through a cyclic R22(8 association.

  20. 5-Iodo-3-phenyl-2,1-benzoxazole

    Directory of Open Access Journals (Sweden)

    Yuriy Teslenko

    2013-04-01

    Full Text Available The title compound, C13H8INO, was prepared by a condensation reaction of 4-nitrobenzene with phenylacetonitrile in NaOH–ethanol solution. There are two independent molecules in the asymmetric unit, in which the dihedral angles between the benzene ring and the benzoisoxazole unit are 4.2 (3 and 4.1 (3°. The crystal packing is governed by C—H...N, C—I...π and C—I...O interactions.

  1. Synthesis and Characterization of Novel Thiazole Anchored Pyrazolyl Benzoxazoles

    Directory of Open Access Journals (Sweden)

    H. N. Akolkar

    2015-03-01

    Full Text Available 3-Formylchromone 1 was treated with 1-(4-(4-bromophenylthiazol-2-ylhydrazine 2 to get (1-(4-(4-bromophenylthiazol-2-yl-1H-pyrazol-4-yl(2-hydroxyphenylmethanone ­­­­­­­­(3a-e. Compound 3 on treatment with NH2OH/HCl gavethe compound 2-[(E-{1-[4-(4-bromophenyl-1,3-thiazol-2-yl]-1H-pyrazol-4-yl}(hydroxyiminomethyl]phenol (4a-e. Compound 4 on treatment with POCl3 gave 2-(1-(4-(4-bromophenylthiazol-2-yl-1H-pyrazol-4-ylbenzo[d]oxazole (5a-e. The synthesized compounds have been characterized with the help of spectral techniques.

  2. Poly(ether-imide-benzoxazole) via Nucleophilic Aromatic Substitution with Fluorophenyl/phenolic Precursor

    Science.gov (United States)

    1992-05-29

    mixture cooled, and 1 equivalent of HCI Polyimides and polybenzoxazoles have good mechanical and added to give 3b; 255-257*C. Ammonium formate was reacted...synthesis and 2a: 216T0, 3a: 225- 227CC and 4a: 325- 3270C. 4-Fluorobenzoyl processing. For these reasons, polybenzoxazoles have only recently chloride...Characterization and Applications: Pie .jm Press: New York, 1989. 3. Yang, H. H., Aromatic High Strength Fibers : Wiley- lnterscience: New York, 1989

  3. Crystal structure of 2-(2-aminophenyl-1,3-benzoxazole

    Directory of Open Access Journals (Sweden)

    Imelda Pérez-Pérez

    2015-02-01

    Full Text Available Crystals of the title compound, C13H10N2O, were grown from a dichloromethane/ketone/methanol solvent mixture. It crystallizes with two molecules, A and B, in the asymmetric unit with very similar almost planar conformations [dihedral angles between the ring planes = 0.74 (8 and 0.67 (6° for molecules A and B, respectively; r.m.s. overlay fit = 0.019 Å]. Each molecule features an intramolecular N—H...N hydrogen bond, which closes an S(6 ring and therefore establishes a syn relationship for the N atoms. In the crystal, molecules are linked by N—H...N hydrogen bonds, generating [100] chains containing alternating A and B molecules. Weak aromatic π–π stacking [minimum centroid–centroid separation = 3.6212 (9 Å] links the chains into a three-dimensional network.

  4. Crystal structure of 2-(2-amino­phen­yl)-1,3-benzoxazole

    Science.gov (United States)

    Pérez-Pérez, Imelda; Martínez-Otero, Diego; Rojas-Lima, Susana; López-Ruiz, Heraclio

    2015-01-01

    Crystals of the title compound, C13H10N2O, were grown from a di­chloro­methane/ketone/methanol solvent mixture. It crystallizes with two mol­ecules, A and B, in the asymmetric unit with very similar almost planar conformations [dihedral angles between the ring planes = 0.74 (8) and 0.67 (6)° for mol­ecules A and B, respectively; r.m.s. overlay fit = 0.019 Å]. Each mol­ecule features an intra­molecular N—H⋯N hydrogen bond, which closes an S(6) ring and therefore establishes a syn relationship for the N atoms. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds, generating [100] chains containing alternating A and B mol­ecules. Weak aromatic π–π stacking [minimum centroid–centroid separation = 3.6212 (9) Å] links the chains into a three-dimensional network. PMID:25878815

  5. 苯并噁唑类荧光增白剂%Benzoxazole Type Fluorescent Brightener

    Institute of Scientific and Technical Information of China (English)

    肖锦平; 竹百均; 石赵泉; 程德文

    2008-01-01

    本文综述了苯并噁唑类荧光增白剂的主要品种,典型产品的合成工艺,该类荧光增白剂的主要应用领域及应用方法,重点介绍了该类荧光增白荆各品种之间及和其它化学结构类型荧光增白荆之间按一定比例混合复配后使用能产生加和增效的效果.简介了国内生产现状.提出发展过程中要重视的问题.

  6. 2-苯基苯并噁唑的合成%Synthesis of 2-phenyl Benzoxazoles

    Institute of Scientific and Technical Information of China (English)

    冯桂荣; 刘征原; 张健扬; 张会茹

    2006-01-01

    以邻氨基苯酚和苯甲酸为原料合成2-苯基苯并噁唑,用正交试验得出最佳合成条件:溴化四丁基铵(TBAB)为相转移催化剂,n(邻氨基苯酚):n(苯甲酸)=1:1.5,反应温度为110℃,反应时间为6h,产率89.5%.

  7. Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita-Baylis-Hillman carbonates.

    Science.gov (United States)

    Ceban, Victor; Putaj, Piotr; Meazza, Marta; Pitak, Mateusz B; Coles, Simon J; Vesely, Jan; Rios, Ramon

    2014-07-18

    An expedited method has been developed for the diastereoselective synthesis of highly functionalized alkyl-azaarene systems with good yields and high diastereoselectivities (>15 : 1 dr). The methodology includes a synergistic catalysis event involving organometallic (10 mol% AgOAc) activation of an alkyl azaarene and Lewis base (10 mol% DABCO) activation of a Morita-Baylis-Hillman carbonate. The structure and relative configuration of a representative product were confirmed by X-ray analysis.

  8. Crystal structure of 2-(2-amino-phen-yl)-1,3-benzoxazole.

    Science.gov (United States)

    Pérez-Pérez, Imelda; Martínez-Otero, Diego; Rojas-Lima, Susana; López-Ruiz, Heraclio

    2015-02-01

    Crystals of the title compound, C13H10N2O, were grown from a di-chloro-methane/ketone/methanol solvent mixture. It crystallizes with two mol-ecules, A and B, in the asymmetric unit with very similar almost planar conformations [dihedral angles between the ring planes = 0.74 (8) and 0.67 (6)° for mol-ecules A and B, respectively; r.m.s. overlay fit = 0.019 Å]. Each mol-ecule features an intra-molecular N-H⋯N hydrogen bond, which closes an S(6) ring and therefore establishes a syn relationship for the N atoms. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, generating [100] chains containing alternating A and B mol-ecules. Weak aromatic π-π stacking [minimum centroid-centroid separation = 3.6212 (9) Å] links the chains into a three-dimensional network.

  9. Novel benzoxazole inhibitor of dengue virus replication that targets the NS3 helicase.

    Science.gov (United States)

    Byrd, Chelsea M; Grosenbach, Douglas W; Berhanu, Aklile; Dai, Dongcheng; Jones, Kevin F; Cardwell, Kara B; Schneider, Christine; Yang, Guang; Tyavanagimatt, Shanthakumar; Harver, Chris; Wineinger, Kristin A; Page, Jessica; Stavale, Eric; Stone, Melialani A; Fuller, Kathleen P; Lovejoy, Candace; Leeds, Janet M; Hruby, Dennis E; Jordan, Robert

    2013-04-01

    Dengue virus (DENV) is the predominant mosquito-borne viral pathogen that infects humans with an estimated 50 to 100 million infections per year worldwide. Over the past 50 years, the incidence of dengue disease has increased dramatically and the virus is now endemic in more than 100 countries. Moreover, multiple serotypes of DENV are now found in the same geographic region, increasing the likelihood of more severe forms of disease. Despite extensive research, there are still no approved vaccines or therapeutics commercially available to treat DENV infection. Here we report the results of a high-throughput screen of a chemical compound library using a whole-virus assay that identified a novel small-molecule inhibitor of DENV, ST-610, that potently and selectively inhibits all four serotypes of DENV replication in vitro. Sequence analysis of drug-resistant virus isolates has identified a single point mutation, A263T, in the NS3 helicase domain that confers resistance to this compound. ST-610 inhibits DENV NS3 helicase RNA unwinding activity in a molecular-beacon-based helicase assay but does not inhibit nucleoside triphosphatase activity based on a malachite green ATPase assay. ST-610 is nonmutagenic, is well tolerated (nontoxic) in mice, and has shown efficacy in a sublethal murine model of DENV infection with the ability to significantly reduce viremia and viral load compared to vehicle controls.

  10. 苯并噁唑类液晶的合成%Synthesis of Benzoxazoles Liquid Crystals

    Institute of Scientific and Technical Information of China (English)

    张建立; 尚洪勇; 梁晓; 刘鑫勤

    2009-01-01

    自主设计了苯并噁唑类液晶的合成路线.采用对烷基苯酚为起始原料,合成制得对烷基邻硝基苯酚,还原得到对烷基邻氨基苯酚,再与烷基苯氰在多聚磷酸脱水剂存在下合环得到2,5-取代苯并噁唑类液晶化合物,并在此基础上进一步拓展,合成出了系列化合物.标定了产品结构,测定了相关液晶参数,对液晶材料的性能进行了研究.在所研究的液晶化合物中,有的品种已实现了量产.

  11. Aromatic Polyimide and Crosslinked Thermally Rearranged Poly(benzoxazole-co-imide) Membranes for Isopropanol Dehydration via Pervaporation

    KAUST Repository

    Ming Xu, Yi

    2015-10-31

    Novel crosslinked thermally rearranged polybenzoxazole (C-TR-PBO) membranes, which show impressive results for isopropanol dehydration, have been obtained via in-situ thermal conversion of hydroxyl-containing polyimide precursors. The polyimide precursors are synthesized by the polycondensation of three monomers; namely, 4,4′-(hexafluoroisopropylidene) diphthalic anhydride (6FDA), 3,3′-dihydroxybenzidine diamine (HAB) and 3,5-diaminobenzoic acid (DABA). Due to the incorporation of the carboxylic-group containing diamine DABA into an ortho-hydroxypolyimide precursor, the thermal induced crosslinking reaction can be achieved together with the thermal rearrangement process. Consequently, a synergistic effect of high permeability and high selectivity can be realized in one step. The resultant C-TR-PBO membrane exhibits an unambiguous enhancement in permeation flux compared to their polyimide precursors. Moreover, the newly developed C-TR-PBO membrane displays stable isopropanol dehydration performance at 60 °C throughout the continuous 200 hours. The promising preliminary results achieved in this study may offer useful insights for the selection of membrane materials for pervaporation and new methods to molecularly design next-generation pervaporation membranes.

  12. S8 -Mediated Cyclization of 2-Aminophenols/thiophenols with Arylmethyl Chloride: Approach to Benzoxazoles and Benzothiazoles.

    Science.gov (United States)

    Gan, Haifeng; Miao, Dazhuang; Pan, Qiang; Hu, Renhe; Li, Xiaotong; Han, Shiqing

    2016-06-21

    A metal-free approach to benzazoles from arylmethyl chlorides and 2-mercaptan/2-hydroxyanilines using elemental sulfur as a traceless oxidizing agent has been developed. The reactions proceeded in good to excellent yields, exhibiting good functional groups tolerance and gram-scale ability. A key mechanistic investigation indicated that the key intermediate trisulfide 6, which was characterized by NMR, HRMS and crystal X-ray crystallography, was separated in the reaction prior to the formation of the product.

  13. Progress in Synthesis of 2-Substituted Benzoxazoles%2-取代苯并(噁)唑的合成进展

    Institute of Scientific and Technical Information of China (English)

    邢瑞光; 李亚男

    2014-01-01

    苯并(噁)唑是医药、农药和天然产物等领域中非常重要的一类中间体,其中2-取代苯并(噁)唑又是苯并(噁)唑中最重要的一类化合物.从不同的原料出发,综述了近些年来关于2-取代苯并(噁)唑的合成方法的研究进展,并对各类合成方法的反应条件、适用范围、产率以及机理的研究进行了讨论和总结.

  14. 2-甲基苯并恶唑的合成研究%Synthesis of 2-Methyl Benzoxazoles

    Institute of Scientific and Technical Information of China (English)

    冯桂荣

    2007-01-01

    以邻氨基苯酚和乙酸为原料合成2-甲基苯并恶唑,用正交试验得出优化合成条件:溴化四丁基铵(TBAB)为相转移催化荆,n(邻氨基苯酚):n(乙酸)=1:1,反应温度为50℃,收率90.4%.此法原料易得,条件温和,操作简便,收率良好.

  15. Stimulated emission of ultraviolet radiation by vapors of complex molecules

    Energy Technology Data Exchange (ETDEWEB)

    Barkova, L.A.; Gruzinskii, V.V.; Danilova, V.I.; Degtyarenko, K.M.; Kopylova, T.N.; Kuznetsov, A.L.

    1981-08-01

    Lasing was observed in vapors of new organic compounds: para-terphenyl, 2-phenylbenzoxazole, 2-(n-tolyl) benzoxazole, 2-(n-methoxyphenyl) benzoxazole, 2-(n-dimethylaminophenyl) benzoxazole, 2-biphenylbenzoxazole, 2-(..cap alpha..-naphthyl) benzoxazole, and also 1,4-di(n-phenylethynyl) benzole, and para-quaterphenyl pumped transversely by XeCl excimer laser radiation at lambda/sub p/ = 308 nm. The lasing bands without tuning covered the 330--370 nm range. The shortest-wavelength maximum (333.5 nm) was observed for 2-(n-methoxyphenyl) benzoxazole. An analysis was made of the lasing ability of the molecules.

  16. The role of hydrogen bonding in the fluorescence quenching of 2,6-bis((E)-2-(benzoxazol-2-yl)vinyl)naphthalene (BBVN) in methanol

    Science.gov (United States)

    Hammam, Essam; Basahi, Jalal; Ismail, Iqbal; Hassan, Ibrahim; Almeelbi, Talal

    2017-02-01

    The excited state hydrogen bonding dynamics of BBVN in hydrogen donating methanol solvent was explored at the TD-BMK/cc-pVDZ level of theory with accounting for the bulk environment effects at the polarizable continuum model (PCM). The heteroatoms of the BBVN laser dye form hydrogen bonds with four methanol molecules. In the formed BBVN-(MeOH)4 complex, the A-type hydrogen bond (N…HO), of an average strength of 25 kJ mol- 1, is twofold stronger than the B-type (O…HO) one. Upon photon absorption, the total HB binding energy increases from 78.5 kJ mol- 1 in the ground state to 82.6 kJ mol- 1 in the first singlet (S1) excited state. In consequence of the hydrogen bonding interaction, the absorption band maximum of the BBVN-(MeOH)4 complex, which was anticipated at 398 nm (exp. 397), is redshifted by 5 nm relative to that of the free dye in methanol. The spectral shift of the stretching vibrational mode for the hydrogen bonded hydroxyl groups (with a maximum shift of 285 cm- 1) from that of the free methanol indicated the elevated strengthening of hydrogen bonds in the excited state. The vibrational modes associated with hydrogen bonding provide effective accepting modes for the dissipation of the excitation energy, thus, decreasing the fluorescence quantum yield of BBVN in alcohols as compared to that in the polar aprotic solvents. Since there is no sign of photochemistry or phosphorescence, it seems reasonable in view of the outcomes of this study to assign the major decay process of the excited singlet (S1) of BBVN in alcohols to vibronically induced internal conversion (IC) facilitated by hydrogen bonding.

  17. Solid phase extraction-preconcentration and high performance liquid chromatographic determination of 2-mercapto-(benzothiazole, benzoxazole and benzimidazole) using copper oxide nanoparticles.

    Science.gov (United States)

    Parham, Hooshang; Khoshnam, Farzaneh

    2013-09-30

    This study introduces a novel method of solid phase extraction (SPE), preconcentration and HPLC determination of 2-mercaptobenzimidazole (2MBI), 2-mercaptobenzoxazole (2MBO) and 2-mercaptobenzothiazole (2MBT) from an aqueous solution by a SPE cartridge loaded with copper oxide nanoparticles. Results demonstrated that copper oxide nanoparticles are quite efficient for extraction and preconcentration of trace amounts of these mercaptans at room temperature. The study also investigated the effects of parameters such as pH, buffer and its volume, electrolyte concentration, flow rate of the test solution, composition and volume of the desorbing solvent, accepted tolerable volume, amount of adsorbent, reusability of cartridges and evidence of some co-existing species on extraction and determination of the above mentioned mercaptans. The method showed good linearity for determination of these mercaptans in the range of 0.01-10 μg mL(-1) with regression coefficients better than 0.9969. The limits of detection (LODs) evaluations were 0.0021, 0.0027 and 0.0019 μg mL(-1) for 2MBT, 2MBO and 2MBI, respectively. The relative standard deviations (RSDs) for 0.2 μg mL(-1) and 5 μg mL(-1) of the measured mercaptans were below 3.04% and 4.23%, respectively. Ramin Power Plant (3000 MW, Ahvaz, Iran) cooling water containing some 2MBT (as corrosion inhibitor) was used as the real sample. Recovery tests with spiked levels of 2MBT, 2MBI and 2MBO were carried out and satisfied results were obtained.

  18. Review on the Synthesis of Poly(Imide-Benzoxazole)%聚苯并口恶唑-酰亚胺的合成方法

    Institute of Scientific and Technical Information of China (English)

    陈向群; 王娟; 孙秋; 蔡伟; 王福平

    2008-01-01

    文中简要概述了聚苯并口恶唑-酰亚胺的性能和应用,并对聚苯并口恶唑-酰亚胺的合成作了较详细的综述,特别阐述了在多聚磷酸中"一锅法"合成聚苯并口恶唑-酰亚胺合成的新方向,以及展望了聚苯并口恶唑-酰亚胺合成研究的前景.

  19. 苯并(噁)唑侧基聚酰亚胺的制备与性能%Preparation and Characterization of Polyimide with Benzoxazole Pendent Group

    Institute of Scientific and Technical Information of China (English)

    杨进; 周雪松; 詹怀宇; 胡健; 顾宜; 刘向阳

    2009-01-01

    为了改善聚酰亚胺的不溶不熔性,一类可溶性苯并噁唑侧基聚酰亚胺树脂被成功制备.从合成的前体侧链为邻羟基苯胺酰胺结构的聚酰亚胺体系出发,进一步催化环化邻羟基苯胺酰胺为苯并噁唑结构,制备了苯并噁唑侧基聚酰亚胺.对这两类不同侧链结构的聚合物树脂进行了红外光谱的结构表征,以及最终成膜的溶解性能、力学性能和耐热性能测试.研究结果表明,苯并噁唑侧基聚酰亚胺溶解于非质子极性有机溶剂中,其力学性能优于相应的主链型聚酰亚胺,且TGA分析表明,其初始分解温度高达597℃,有望用于航空航天方面高强、高模、耐高温的结构材料.

  20. 4,4'-双苯并唑二苯乙烯的合成%Synthesis of 4,4'-bis(2-benzoxazol-2-yl ) stilbene

    Institute of Scientific and Technical Information of China (English)

    王金波; 秦瑞香; 刘福胜; 于世涛

    2005-01-01

    以对氰基苄基氯、邻氨基苯酚和对醛基苯基苯并口恶唑为原料,经加成环化、酯化、缩合三步反应,合成了荧光增白剂双苯并口恶唑二苯乙烯.重点讨论了酯化、缩合两步反应的优化条件,在n(对氯甲基苯基苯并口恶唑)∶n(亚磷酸三乙酯)=1∶4,反应温度165℃,反应时间5 h下,酯化收率可达92%;在n(苯并口恶唑基苄基膦酸二乙酯)∶n(对醛基苯基苯并口恶唑)∶n(甲醇钠)=1∶1∶1.6,反应温度20℃,反应时间8 h下,缩合收率达到91%以上.双苯并口恶唑二苯乙烯产品纯度大于99%,并用元素分析、红外光谱以及紫外吸收光谱对所得的化合物进行了表征.

  1. Novel ¹⁸F-labeled benzoxazole derivatives as potential positron emission tomography probes for imaging of cerebral β-amyloid plaques in Alzheimer's disease.

    Science.gov (United States)

    Cui, Mengchao; Ono, Masahiro; Kimura, Hiroyuki; Ueda, Masashi; Nakamoto, Yuji; Togashi, Kaori; Okamoto, Yoko; Ihara, Masafumi; Takahashi, Ryosuke; Liu, Boli; Saji, Hideo

    2012-11-01

    Two radiofluoro-pegylated phenylbenzoxazole derivatives, 4-(5-(2-(2-(2-[(18)F]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N-methylaniline ([(18)F]24) and 4-(5-(2-(2-(2-[(18)F]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N,N-dimethylaniline ([(18)F]32), were synthesized and evaluated as probes for imaging cerebral β-amyloid (Aβ) plaques in living brain tissue by PET. [(18)F]24 and [(18)F]32 displayed high affinity for Aβ(1-42) aggregates (K(i) = 9.3 and 3.9 nM, respectively). In vitro autoradiography with sections of post-mortem AD brain and transgenic mouse brain confirmed the affinity of these tracers. Initial high uptake into and rapid washout from the brain in normal mice were observed. [(18)F]24 also displayed excellent binding to Aβ plaques in ex vivo autoradiographic experiments with Tg2576 mice. Furthermore, small-animal PET studies demonstrated significant differences in the clearance profile after the administration of [(18)F]24 between Tg2576 and wild-type mice. The results suggest [(18)F]24 to be a useful PET agent for detecting Aβ plaques in the living human brain.

  2. Synthesis and the spectral properties of benzoxazole compounds%苯并噁唑类化合物合成及光谱性质研究

    Institute of Scientific and Technical Information of China (English)

    郭安众; 欧阳杰; 张家祥; 李敦猛

    2010-01-01

    在乙醇中以取代水杨醛与邻氨基酚反应合成希夫碱,以Mn(OAc)3氧化生成相应的羟基苯基苯并噁唑类化合物.测定了相应荧光化合物的荧光光谱图,发现化合物中羟基对位取代卤素随着分子量的增大,吸收和发射波长增长,荧光量子收率增大,Stokes位移减小.羟基邻位、对位都有溴原子取代时量子收率最大,吸收和发射波长也增大.

  3. 2-对甲苯基苯并(噁)唑合成方法综述(续)%A Review of Synthesis Methods for 2-(p-Tolyl)benzoxazole

    Institute of Scientific and Technical Information of China (English)

    葛广周

    2014-01-01

    在深入研究报道的苯并(噁)唑类化合物合成方法及分析2-对甲苯基苯并(噁)唑化合物结构特点的基础上,以2-对甲苯基苯并(噁)唑为代表,以合成苯并(噁)唑环为主线,归纳出拉登堡(Ladenburg)苯并(噁)唑合成法、类-拉登堡苯并(噁)唑合成法及非-拉登堡苯并(噁)唑合成法三大合成途径.按合成原料类别分类,系统概述了2-对甲苯基苯并(噁)唑合成路线和合成方法.列出了各反应的主要条件和收率,讨论了部分路线的反应机理,给出了一些研究建议.

  4. 一锅法合成对苯撑二(4-氨基苯并恶唑)%One-pot Synthesis of Poly p(4-Amino Benzoxazole)

    Institute of Scientific and Technical Information of China (English)

    于洪艳; 王兴利

    2012-01-01

      用对苯二甲酸、2,4-二氨基苯酚盐酸盐为原料,五氧化二磷和磷酸反应生成的多聚磷酸为催化剂,合成了对苯撑二(4-氨基苯并恶唑).考察了催化剂配比、原料配比及粗品精制溶剂等因素对产品纯度及收率的影响.结果表明,对苯二甲酸:2,4-二氨基苯酚盐酸盐=1︰2.05;磷酸:五氧化二磷=1︰1.35;采用混合溶剂进行精制,在此条件下产品的最终纯度达到99.2%

  5. 主链含有苯并噁唑环的PPV型齐聚物的合成%SYNTHESIS OF PPV OLIGOMER CONTAINING BENZOXAZOLE IN MAIN CHAIN

    Institute of Scientific and Technical Information of China (English)

    张田林; 吴亚明; 高云

    2003-01-01

    以5-甲基-2-氯甲基苯并(口恶)唑和对二苯甲醛为主要原料,通过两次Wittig-Horner反应,合成了未见文献报道的主链含有苯并NFDA1唑环的PPV型齐聚物.目的在于在PPV聚合物主链中嵌入电子传输型结构单元,提高聚对苯撑乙烯共轭链的电子传输能力,改变PPV的发光特性.分析数据表明,该齐聚物的w为2500,并且分子结构中的乙烯基 C C 双键均为反式结构特征.UV-Vis吸收光谱特征峰λmax等于497 nm.

  6. 5-氨基-2-(对氨基苯)苯并(哑)唑的合成%Synthesis of 5-amino-2-(p-aminophenyl)benzoxazole

    Institute of Scientific and Technical Information of China (English)

    梁栎桦; 杨光; 刘超

    2008-01-01

    以2,4-二氨基苯酚盐酸盐和对氨基苯甲酸为原料合成了5-氨基-2-(对氨基苯)苯并(噁)唑.反应过程中,首次加入SnCl2作为还原剂,抑止了2,4-二氨基苯酚盐酸盐的氧化,有效地提高了反应产率.同时研究了一种有效的提纯5-氨基-2-(对氨基苯)苯并(噁)唑的方法.与其他方法相比,该方法操作过程简便,产率较高,产物可作为聚合反应的单体原料.

  7. 一种荧光增强型苯并噁唑类锌离子探针%A Fluorescence Enhancement Zn2+ Probe Based on Benzoxazole

    Institute of Scientific and Technical Information of China (English)

    熊启杰; 王强; 李伟; 石玉娟; 潘蕾; 艾思凡; 张勇; 方志强

    2016-01-01

    以8-氨基喹啉为识别基团,设计合成了一种苯并噁唑类荧光增强型锌离子探针( ZY7 ) ,用质谱和核磁等方法对其进行了结构表征,并研究了它的荧光性质. 实验结果表明,ZY7对Zn2+具有较强的选择性,响应快速,抗干扰能力强,可实现对Zn2+的可视化检测;在水体样品中对Zn2+的检测表明ZY7具有潜在的应用价值.

  8. Synthesis of L-tyrosine Derivatives、with Benzoxazole%含苯并噁唑的L-酪氨酸衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    杨金志; 欧阳贵平; 陈琨; 汪春梅; 任志尧

    2008-01-01

    从L-酪氨酸乙酯出发,经氨基保护、硝化、还原反应制得3-氨基-L-酪氨酸乙酯(4);4与苯甲醛或取代苯甲醛完成环化反应,合成了6个新的含苯并噁唑的L-酪氨酸衍生物,其结构经1H NMR,13C NMR,IR和元素分析表征.

  9. 3-{[5-(4-Bromophenylimidazo[2,1-b][1,3,4]thiadiazol-2-yl]methyl}-1,2-benzoxazole

    Directory of Open Access Journals (Sweden)

    Ravi S. Lamani

    2011-01-01

    Full Text Available In the title compound, C18H11BrN4OS, the imidazothiadiazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3 0.015 (4 Å, respectively, and are inclined at an angle of 23.51 (7° with respect to each other. The planes of the imidazothiadiazole and bromophenyl rings are inclined at an angle of 27.34 (3°. In the crystal, intermolecular C—H...N interactions result in chains of molecules along the b and c axes. Moreover, C—H...O interactions result in centrosymmetric head-to-head dimers with R22(24 graph-set motifs. The molecular packing is further stabilized by π–π stacking interactions between the imidazole rings with a shortest centroid–centroid distance of 3.492 (3 Å. In addition, C—H...π interactions are observed in the crystal structure.

  10. Large fluorescence response by alcohol from a bis(benzoxazole)-zinc(II) complex: the role of excited state intramolecular proton transfer.

    Science.gov (United States)

    Wang, Junfeng; Chu, Qinghui; Liu, Xiumin; Wesdemiotis, Chrys; Pang, Yi

    2013-04-18

    The formation of a bis(HBO) anion is known to turn on the fluorescence to give red emission, via controlling the excited-state intramolecular proton transfer (ESIPT). The poor stability of the formed anion, however, hampered its application. The anion stability is found to be greatly improved by attaching the anion to Zn(2+) cation (i.e., forming zinc complex), whose emission is at λem ≈ 550 and 760 nm. Interestingly, addition of methanol to the zinc complex induces a remarkable red fluorescence (λem ≈ 630 nm, φfl ≈ 0.8). With the aid of spectroscopic studies ((1)H NMR, UV-vis, fluorescence, and mass spectra), the structures of the zinc complexes are characterized. The emission species is identified as a dimer-like structure. The study thus reveals an effective fluorescence switching mechanism that could further advance the application of ESIPT-based sensors.

  11. Preparation and properties of polyimide containing benzoxazole units%含苯并噁唑结构共聚酰亚胺的合成及其性能

    Institute of Scientific and Technical Information of China (English)

    卢泓旭; 陈英韬; 董杰; 尹朝清; 吉亚丽; 张清华

    2014-01-01

    联苯四羧酸二酐(BPDA)与4,4 '-二氨基二苯醚(ODA)及自制的2,6-二(对氨基苯)苯并[1,2-d;5,4-d']二噁唑(DAPBBO)在二甲基乙酰胺中共聚,然后进行铺膜和热酰亚胺化,得到了含有双苯并噁唑的共聚酰亚胺薄膜,对其结构、热性能、力学性能及光学性能进行了表征.结果表明:杂环单体的引入提高了聚酰亚胺的力学性能,增加了聚酰亚胺的玻璃化转变温度,并且使聚酰亚胺薄膜具有良好的紫外吸收能力.

  12. Synthesis of Novel Benzoxazole and Benzothiazole Derivatives%新型苯并噁唑(噻唑)衍生物的合成与表征

    Institute of Scientific and Technical Information of China (English)

    张英俊; 谭小华; 邵光; 彭志鸿; 安德烈

    2005-01-01

    通过N-氯乙酰或N,N′-二氯乙酰取代的含氮杂环中间体, 4,5-二氯-2-苯基-3-哒嗪酮分别与2-巯基苯并噁唑和2-巯基苯并噻唑反应,合成了8个未见文献报道的苯并噁唑和苯并噻唑衍生物,其结构经1H NMR, IR, MS及元素分析确认.

  13. 3-({4-[(2-Methylbenzylideneamino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl-1,3-benzoxazol-2(3H-one

    Directory of Open Access Journals (Sweden)

    Abdullah Aydın

    2013-02-01

    Full Text Available In the title compound, C18H15N5O2S, a weak intramolecular C—H...S hydrogen bond results in a small dihedral angle of 3.71 (9° between the methylphenyl and triazole rings, which, in turn, form dihedral angles of 80.09 (8 and 77.32 (8°, respectively, with the benzoxazolone mean plane. In the crystal, N—H...O hydrogen bonds link molecules into chains along [001], and weak C—H...N hydrogen bonds and π–π interactions between the five- and six-membered rings [centroid–centroid distances = 3.5074 (11 and 3.616 (1 Å] consolidate the crystal packing.

  14. Generation of UV radiation by vapors of complex molecules

    Energy Technology Data Exchange (ETDEWEB)

    Barkova, L.A.; Gruzinskii, V.V.; Danilova, V.I.; Degtiarenko, K.M.; Kopylova, T.N.; Kuznetsov, A.L.

    1981-08-01

    Laser action has been obtained in the following organic compounds under pumping by XeCl excimer laser radiation at 308 nm: para-terphenyl, 2-phenylbenzoxazole, 2-(n-tolyl)-benzoxaxole, 2-(n-methoxyphenyl)-benzoxazole, 2-(n-dimethylaminophenyl)-benzoxazole, 2-biphenylbenzoxazole, (2-alpha-naphthyl)-benzoxazole, 1.4-di(n-phenylethynyl)-benzole, and paraquaterphenyl. The nontuning lasing bands covered the range of 330-370 nm, and the most short-wavelength maximum (333.5 nm) was found for 2(n-methoxyphenyl)-benzoxazole. The lasing capability of the molecules was analyzed.

  15. Research on the Microwave Synthesis and Spectroscopy of 2-Aryl-substituted Benzoxazole%2-芳基取代苯并噁唑的微波合成及光谱研究

    Institute of Scientific and Technical Information of China (English)

    冯丽恒; 赵三虎; 陈兆斌

    2005-01-01

    在微波辐射条件下,利用邻氨基酚和芳基羧酸在多聚磷酸催化下进行缩合反应,合成了5种2-芳基取代苯并噁唑化合物.反应的最佳条件为:多聚磷酸为催化剂,辐射功率260 W,辐射时间为4 min.并对其荧光光谱进行了初步研究,研究表明:随着苯环上取代基吸电子能力的减弱,化合物的荧光最大发射波长向长波方向移动.

  16. Synthesis of 4-(5-methylbenzoxazol-2-yl )-4'-( benzoxazol-2-yl ) stilbene%4-(5-甲基苯并恶唑基)-4′-苯并恶唑基二苯乙烯的合成

    Institute of Scientific and Technical Information of China (English)

    王金波; 秦瑞香; 刘福胜; 于世涛

    2005-01-01

    以对氰基苄基氯、邻氨基对甲苯酚和对醛基苯基苯并恶唑为原料,经加成环化、酯化、缩合三步反应合成了荧光增白剂4-(5-甲基苯并恶唑基)-4'-苯并恶唑基二苯乙烯,三步反应的收率分别可达85%、92%和91%以上.双苯并恶唑二苯乙烯产品纯度>99%,并用元素分析、红外光谱以及紫外吸收光谱对所得的化合物进行了表征.

  17. 含苯并噁唑环双偶氮光导颜料的制备及性能%Study on the synthesis and photo-conductivity of a bisazo compound with benzoxazole moiety

    Institute of Scientific and Technical Information of China (English)

    王世荣; 邵斌; 何莉莉; 胡雅琴; 李祥高

    2007-01-01

    以2-(4'-氨基苯基)-6-氨基苯并噁唑为重氮组分,以N-(2-氯苯基)-N'-(3-羟基-2-萘甲酰)脲为偶合组分合成双偶氮化合物.通过紫外可见吸收光谱和红外吸收光谱对产物的结构进行了鉴定.并以合成的双偶氮化合物为电荷产生材料制成功能分离型有机光导体,测试结果表明,在15℃下用DMF处理有利于低结晶度光敏性产物的生成,在可见光区的吸收较强.制备的光导体具有较好的光导性能,V0=770V,VR=40V,E1/2=7.6 lx·s.

  18. Synthesis and Structure of p-tert-Butylthiacalix[4]arene Derivatives Containing Benzoxazole Group%含苯并噁唑基的硫桥杯[4]芳烃衍生物的合成及结构

    Institute of Scientific and Technical Information of China (English)

    赵邦屯; 周振; 颜振宁

    2009-01-01

    在碳酸钾存在下,对叔丁基硫桥杯[4]芳烃(1)分别与端基二溴代烷和碘甲烷反应,生成硫桥杯[4]芳烃衍生物2~4.含端基溴代的硫桥杯[4]芳烃衍生物2和4分别与2-巯基苯并噁唑在碳酸钾存在下反应,生成硫桥杯[4]芳烃衍生物5a~5d.通过1H NMR,13C NMR,IR,MS和元素分析等手段对产物进行了表征.同时,X射线分析确定了硫桥杯[4]芳烃5b的晶体结构.

  19. Theoretic Study on the Nonlinear Optical Properties of 2-Phenyl-1,3-benzoxazole Derivations%2-苯基-1,3-苯并唑衍生物分子的非线性光学性质

    Institute of Scientific and Technical Information of China (English)

    孙振范; 韩长日; 李玉光

    2006-01-01

    2-苯基-1,3-苯并唑分子为母体,设计了一系列取代衍生物,研究了不同取代基,不同取代位置对分子电子结构及分子的非线性光学性质的影响.研究结果表明取代位置对分子的一阶极化率影响不太,对分子的二阶、三阶极化率影响较大,目标分子的二阶极化率与分子的(μe-μg)/ΔE2有较好的相关性.在母体分子的7、8位连接-NO2,13位连接-NH2得到的分子其分子的二阶极化率最大,而在7、8位连接-NH2,13位连接-NO2得到的分子具有最大的三阶极化率.

  20. N-酰基苯并噁唑啉酮类化合物的合成及其生物活性%Synthesis and Bioactivity of Substituted 3H-Benzoxazol-2-ones

    Institute of Scientific and Technical Information of China (English)

    武岳; 袁莉萍; 郭庆铭; 张一宾

    2005-01-01

    采用邻氨基酚为原料合成了N-酰基苯并噁唑啉酮类化合物30个,其化学结构经1H NMR及元素分析确证.初步的生物活性试验结果表明,该类化合物具有一定的杀虫、杀菌活性,其中化合物3b、4b、14b、19b在50 mg/L浓度下对淡色库蚊Culex pipiens palles的致死率为100%,有7个化合物在1 000 mg/L浓度下对朱砂叶螨Tetranychus cennbarinus的致死率达95%以上.

  1. 苯并(口恶)唑封端的聚(2,5-二丁氧基对苯乙炔)的合成%Synthesis of Poly(2,5-dibutoxyl-p-phenylene vinylene)Capped with Benzoxazole

    Institute of Scientific and Technical Information of China (English)

    张田林

    2003-01-01

    研究在2,5-二丁氧基对二氯苄的脱氯化氢聚合反应过程中,掺入2-(4-氯甲基苯基)-5-叔丁基苯并(口恶)唑,直接合成一种可溶性苯并(口恶)唑封端的聚(2,5-二丁氧基对苯乙炔)的方法;应用IR、1H-NMR、UV-Vis等分析方法,对其结构特征进行表征.分析结果表明:苯并(口恶)唑封端的聚(2,5-二丁氧基对苯乙炔)具有链状π-共轭体系的高分子结构特征.

  2. Research on the Synthesis and Spectroscopy of 2-( 2-Phenyl Propenyl ) Benzoxazoles%2-(2-苯基丙烯基)苯并唑类化合物的合成与光谱研究

    Institute of Scientific and Technical Information of China (English)

    王超杰; 赵瑾; 潘家杏

    2001-01-01

    本文讨论了2-(2-取代苯基丙烯基)苯并唑类化合物的合成方法以及取代基对产率的影响,并用IR,NMR,MS,FL等光谱方法对它们进行了结构表征.初步探讨了取代基对各种光谱的影响.结果表明,取代基对苯并唑环的特征红外吸收有影响但没有明显的线性规律,吸电子取代基对分子中丙烯氢和甲基的化学位移影响明显,取代的标题化合物的质谱易出现较强的双正离子碎片.同时讨论了有关紫外光谱和荧光光谱的一些实验现象.

  3. Preparation and Characterization of Acid-Treated Multi-Walled Carbon Nanotubes/Poly(p-Phenylene-2,6-Benzoxazole) Composites%酸处理碳纳米管/PBO复合材料的制备与表征

    Institute of Scientific and Technical Information of China (English)

    李霞; 黄玉东

    2007-01-01

    用原位聚合法成功地制备了碳纳米管/聚对苯撑苯并双(噁)唑(PBO)复合材料.用 FT-IR、XPS、SEM和AFM对碳纳米管和所制备的复合材料进行了表征,结果表明,碳纳米管的酸处理效果好,表面含有C-O、COOH等极性官能团; 复合材料中碳纳米管在聚合物基体中分散均匀,两相界面间存在较强的作用力.

  4. The New Synthesis Method of 2-(4' -hydroxyphenoxy)-6-chloro-benzoxazole%2-(4'-羟基苯氧基)-6-氯苯并恶唑的合成新方法

    Institute of Scientific and Technical Information of China (English)

    吴永虎

    2005-01-01

    以2,6-二氯苯并恶唑、对苯二酚为原料,于水-甲苯体系中在PTC的作用下合成2-(4'-羟基苯氧基)-6-氯苯并恶唑,彻底改变了原来的二甲苯单一溶剂反应体系,产品含量大于95%,收率达到83%以上.该方法克服了老工艺收率低,产量小,产品质量差的缺点.

  5. 含有苯并(噁)唑及吡啶基团的双杂芳基乙炔的合成%Synthesis of Diheteroarylacetylenes Containing Benzoxazole and Pyridine Groups

    Institute of Scientific and Technical Information of China (English)

    刘杰; 庄俊鹏; 郝海军; 张曙光; 牛俊宇

    2015-01-01

    标题化合物通过双杂芳基乙烯在加热回流的二氯甲烷中加溴,然后室温下在四氢呋喃溶液中由叔丁醇钾脱溴的方法进行制备,合成了8种未见文献报道的标题化合物.与过渡金属催化方法相比,此种制备方法原料易得,反应简便高效,不需要有昂贵金属参与.对所得产物进行了紫外和荧光光谱的检测,光化学测试表明,在紫外光照射下,标题化合物在有机溶剂或酸性水溶液中没有光化学活性.

  6. Synthesis and Photoelectricity of Bipolar Stilbenyl Derivatives with Triphenylamino and Benzoxazole as Charge-transporting Groups%双极型均二苯乙烯发光材料的合成和光电特性

    Institute of Scientific and Technical Information of China (English)

    张田林; 马娟娟; 贾海红

    2007-01-01

    已发现三苯胺基和苯并(噁)唑是优良的有机共轭发光材料电荷传输基团.将三苯胺基作为空穴传输基团和苯并(噁)唑作为电子传输基团引入均二苯乙烯分子中,设计并合成了四个新双极小分子发光物质4-二苯氨基-4'-(2-苯并(噁)唑)均二苯乙烯.通过光谱分析和元素分析等方法确认了其化学结构.所合成化合物的相关分析结果表明化学结构、取代基效应、溶剂环境等因素对其UV-Vis光谱、荧光光谱、荧光量子产率、电致发光谱和启亮电压都产生一定的影响.

  7. 微波辅助下苯并噁唑衍生物的合成与结构表征%Microwave-assisted Synthesis and Structural Characteristic of Benzoxazole Derivatives

    Institute of Scientific and Technical Information of China (English)

    王帆; 袁金伟; 张瑞; 买文鹏; 杨亮茹; 毛璞; 屈凌波

    2015-01-01

    在微波辐射条件下,以邻氨基苯酚衍生物和原甲酸三乙酯为原料,发生分子间和分子内的消去反应合成了5种取代苯并噁唑化合物,其结构通过IR、NMR和ESI MS等证实.通过对反应影响因素的考察,最佳的反应条件是:在无溶剂条件下,邻氨基苯酚衍生物与原甲酸三乙酯的物质的量比为1∶1.5,反应温度为100℃,反应时间为15 min,目标产物最高产率可达94.9%.

  8. Syntheses of 5-Amino-2-(4-aminophenyl)benzoxazole%5-氨基-2-(4-氨基苯)苯并噁唑合成研究

    Institute of Scientific and Technical Information of China (English)

    姜佳一; 庞立营

    2008-01-01

    以邻氨基对硝基苯酚和对硝基苯甲酰氯为原料进行酰胺化反应,再用多聚磷酸进行环化反应,得到中间体5-硝基-2-(4-硝基苯)苯并噁唑(NNB);中间体在77~80℃,压力为2.0~2.5MPa,Raney-Ni作催化剂条件下高压催化加氢合成了5-氨基2-(4-氨基苯)苯并噁唑,纯度为99.8%,总收率为81.1%.通过熔点、MS、元素分析对产品进行了结构表征.

  9. 含噁唑结构固化剂的分子动力学模拟研究%Study on Curing Agent Containing Benzoxazole Groups by Using Molecular Simulation Technology

    Institute of Scientific and Technical Information of China (English)

    卢晓东; 贾近; 肖海英; 黄玉东; 张红星

    2011-01-01

    The models of diglycidyl ether of bisphenol A/diaminophenylbenzoxazoie (E/ABO) were established by means of molecular simulation technique. The study on the glass transition temperature of the cured epoxy resin was performed by means of the models with computer and the simulations were verifying in the experiments. The results showed that the glass transition temperature of cured epoxy resin system could be predicted by means of molecular simulation technique and the glass transition temperatures of the developed E/ABO system were 217t (determined by DSC) and 1881C (determined by DMA). Compared to E/DDS system, it was a great improvement.%首先利用分子模拟技术建立了缩水甘油醚双酚A环氧树脂/二胺基苯并噁唑(E/ABO)固化环氧树脂体系的简单分子模型,并利用这些模型在计算机上对树脂体系的玻璃化转变温度进行研究,同时利用实验进行验证.结果表明,利用分子模拟技术可以很好地预测环氧树脂固化体系的玻璃化转变温度;同时新开发的E/ABO环氧树脂固化体系的玻璃化转变温度分别为217℃(DSC法)和188℃(DMA法),与环氧树脂/二胺基二苯基砜(E/DDS)固化体系相比有很大的提高.

  10. Spacecraft Thermal Protection Systems (TPS) Based on Polybenzoxazole (PBO) With Unique UV, Atomic-O and Solar Wind Protective Coatings Project

    Data.gov (United States)

    National Aeronautics and Space Administration — Poly(benzoxazole) (PBO) is a new polymeric material extremely promising for external spacecraft structural applications, including, e.g., debris and micrometeoroid...

  11. Recent advances in high temperature polymers for microelectronic applications

    Energy Technology Data Exchange (ETDEWEB)

    Labadie, J.W.; Hedrick, J.L. (IBM Almaden Research Center, San Jose, CA (USA))

    1989-12-01

    This paper describes research concerned with the synthesis and properties of a variety of new materials based on polyphenylquinoxalines, polyquinoxalones, polybenzoxazoles and polyimide random copolymers containing phenylquinoxaline and benzoxazole moieties. The synthesis of NMP processable phenylquinoxaline and benzoxazole based poly(aryl ethers) was carried out using a novel heterocyclic activated fluoro displacement by bisphenoxides, affording high T(g), melt and solvent processable polymers with tough, ductile mechanical properties. In addition, heterocyclic activated ether synthesis was used to prepare phenylquinoxaline and benzoxazole containing diamines which were used in conventional polyimide syntheses, yielding random copolymers which showed moduli comparable to PMDA/ODA polyimide and elongations ranging from 60 to 120 percent. Polyquinoxalones were synthesized by the step growth polymerization of bis(keto esters) with bis(o-diamines) and represent an interesting new class of linear polyquinoxalines. The thermal and mechanical properties were evaluated for many of these polymers, and were found to be comparable to polyimides. 11 refs.

  12. Utility of 4-formylantipyrine in heterocyclic synthesis

    Directory of Open Access Journals (Sweden)

    Abdou O. Abdelhamid

    2010-04-01

    Full Text Available Pyrrolo[3,4-c]pyrazole-4,6(1H,5H-dione, pyrano[2,3-c]pyrazole-5-carbonitrile, pyrano[2,3-d]4-imidazolines, pyrido[2,1-b]benzimidazole, pyrido[2,1-b][1,3]benzoxazole, pyrido[2,1-b][1,3]benzothiazole and pyrido[2,1-b]quinazoline were synthesised from antipyrine derivatives with appropriate reagents such as maleimides, malononitrile, ethyl cyanoacetate, benzimidazole-2-acetonitrile, benzothiazole-2-acetonitrile, benzoxazol-2-acetonitrile, benzoylacetonitrile and other reagents. The newly synthesised compounds were established by elemental analysis, spectral data, and alternative synthetic routes whenever possible.

  13. Spectral and electrooptical absorption and emission studies on internally hydrogen bonded benzoxazole 'double' derivatives: 2,5-bis(benzoxazolyl)hydroquinone (BBHQ) and 3,6-bis(benzoxazolyl)pyrocatechol (BBPC). Single versus double proton transfer in the excited BBPC revisited

    Energy Technology Data Exchange (ETDEWEB)

    Wortmann, R.; Lebus, S.; Reis, H. [Institute of Physical Chemistry, University of Mainz, Jakob-Welder-Weg 11, 55099 Mainz (Germany); Grabowska, A.; Kownacki, K. [Institute of Physical Chemistry, Polish Academy of Sciences, 44/52 Kasprzaka, 01-224 Warsaw (Poland); Jarosz, S. [Institute of Organic Chemistry, Polish Academy of Sciences, 44/52 Kasprzaka, 01-224 Warsaw (Poland)

    1999-05-15

    Ground and excited state dipole moments and polarizabilities of 2,5-bis(benzoxazolyl)hydroquinone (BBHQ) and 3,6-bis(benzoxazolyl)pyrocatechol (BBPC) are determined by means of electrooptical absorption and emission measurements. BBHQ is found to exhibit a small, while BBPC a large increase of the static polarizability in the Franck-Condon (FC) excited singlet state. The change of the dipole moments upon excitation to the FC state is zero within experimental error. However, both molecules show dipole moments in the fluorescent states of their phototautomers, of about 5 D, the major component being parallel to the long molecular axis. The experimental and theoretical results strongly suggest that the fluorescent species of BBHQ and BBPC are monoketo-tautomers created by single proton transfer in the course of the excited state relaxation. For BBPC this was confirmed by a comparative photophysical study with its monomethoxy-derivative (MeBBPC), in which one active proton is replaced by the CH{sub 3} group. These results lead to the revision of previous conclusions [Grabowska et al., Chem. Phys. Lett. 177 (1991) 17] stating that BBPC undergoes a double proton transfer in the excited state. For BBHQ the previously found single proton transfer mechanism of tautomerization is fully confirmed. (Copyright (c) 1999 Elsevier Science B.V., Amsterdam. All rights reserved.)

  14. Synthesis of Novel Benzoxazole Heteroaryl Thioether Compounds and Their Effects on Wheat Seed Germination Rate%新型苯并噁唑杂芳基硫醚化合物的合成及其对小麦种子发芽率的影响

    Institute of Scientific and Technical Information of China (English)

    刘霞; 马彩莲; 伊泽

    2016-01-01

    根据活性基团拼接原理,分别以4-甲基-2-氨基苯酚和邻氨基苯酚为原料,SCH2为“桥梁”基团,设计并合成了9个苯并噁唑杂芳基硫醚化合物(6a~6e和10a~10d),其中6,10a和10d为新化合物,其结构经1H NMR,13C NMR,IR和元素分析表征.采用培养皿滤纸发芽法考察了6和10对小麦种子发芽率的影响.结果表明:在合适的浓度下,6和10对小麦种子发芽率均有促进作用.

  15. 原位聚合法制备多壁碳纳米管-聚对苯撑苯并双噁唑纳米复合材料%Multi-walled carbon nanotubes-poly (p-phenylene-2,6-benzoxazole) nanocomposites prepared by in-situ polymerization process

    Institute of Scientific and Technical Information of China (English)

    李霞; 黄玉东; 刘丽; 黎俊

    2006-01-01

    采用强氧化性酸处理多壁碳纳米管(MWNTs),形成官能化的多壁碳纳米管(FMWNTs),用傅立叶红外光谱(FTIR)、光电子能谱(XPS)对处理前后MWNTs的表面官能团进行了分析,并利用原位聚合法成功制备了FMWNTS-PBO纳米复合材料.结果表明,碳纳米管经过酸处理后,表面含有较多羰基和羟基的极性官能团,FMWNTs-PBO纤维的钩接强度比同条件下PBO纤维的钩接强度高出30%.文中给出了FMWNTs和PBO低聚物的聚合机理.

  16. 双[2-(2'-苯氧基)苯并(口恶)唑]二吡啶合锰(Ⅱ)配合物的研究%Synthesis, Crystal Structure and Thermal Decomposition of Bis [2-( 2'-phenoxyl )-benzoxazole]-di-pyridine Manganese(Ⅱ)

    Institute of Scientific and Technical Information of China (English)

    周建华; 李淑兰; 姜海辉; 刘德信; 杨兆荷

    1998-01-01

    X射线晶体结构分析结果表明,标题化合物晶体(C36H26MnN4O4)属单斜晶系,空间群为P21/α,α=0.9833(3),b=1.8646(3),c=0.9449(1)nm,Z2,最终因子Rw=0.057.利用热重分析对配合物晶体两步热分解过程进行了非等温热力学研究,探讨了反应的可能机理,得到其相应的动力学参数.第一步非等温动力学方程为:dα/dt=A·exp(-E/RT)·2(1-α)1/2,第二步:dα/dt=A·exp(-E/RT)·3/2(1-α)[-ln(1-α)]1/3.

  17. Design,Synthesis and 3D-QSAR Study of 2-[N′-(2-Aryloxyethyl)piperazinomethyl]-benzoxazole Series as α1-Adrenoceptor Antagonists%芳氧烷基哌嗪苯并(噁)唑类α1-受体拮抗剂的设计、合成及其3D-QSAR研究

    Institute of Scientific and Technical Information of China (English)

    吴斌; 李敏勇; 江振洲; 夏霖

    2004-01-01

    结合α1-受体拮抗剂的构效关系和我们应用计算机辅助药物设计方法所构建的药效团模型,设计合成了17个1-(5-甲基-2-苯并噁唑甲基)-4(2-取代芳氧乙基)哌嗪类化合物,其结构均经1H NMR,IR及MS(HRMS)确证.初步生物活性测试表明,所合成的目标化合物多数具有较好的α1-受体拮抗活性.3D-QSAR研究为该类化合物的结构改造提供了理论依据.

  18. 4,4′-双(苯并噁唑-2-基)二苯乙烯荧光增白剂(OB-1)的合成%Synthetic Process of Fluorescent Bleaching Agent 4,4′-Bis(benzoxazol-2-yl)stilbene OB-1

    Institute of Scientific and Technical Information of China (English)

    熊振湖

    2003-01-01

    以对甲基苯甲酸及其乙酯为原料,经过三氧化铬在乙酐中的氧化反应、在氯苯溶剂中以氯化亚砜为氯化试剂的侧链氯化反应和亚磷酸三乙酯为乙基化试剂的酯化反应,再经两步缩合反应,合成了荧光增白剂4,4′-双(苯并口恶唑-2-基)二苯乙烯(OB-1).OB-1(由Ⅲ合成Ⅳ粗品)的收率由文献中平均90%提高到平均99%以上.通过对化合物的元素分析、红外光谱以及在DMF中紫外吸收光谱的测定,确定了目标产物的结构.经HPLC测定,w(OB-1)>99%.

  19. Effect of ionic groups on the surface and the interfacial adhesion properties of poly(p-phenylene benzoxazole) (PBO) fiber%离子基团对PBO纤维的表面性能及其界结性能的影响

    Institute of Scientific and Technical Information of China (English)

    金俊弘; 罗开清; 江建明; 杨胜林; 李光

    2006-01-01

    PBO作为增强纤维存在与环氧树脂基体界面粘结性能差的问题.通过在聚合过程中添加少量5-磺酸钠-间苯二甲酸部分替代对苯二甲酸与4,6-二氨基间苯二酚盐酸盐进行共聚,合成了大分子链上含有离子基团的SPBO共聚物,并制得SPBO初生纤维.通过接触角测试和XPS研究了纤维的表面性能,通过微脱粘实验和SEM评价了纤维与环氧树脂基体的界面粘结性能.结果表明: 与PBO纤维相比,SPBO纤维表面浸润性能提高,表面含氮、氧量均增加,与环氧树脂的界面剪切强度从8.2MPa提高到10.1Mpa,提高了23%.

  20. 新型氮杂2-β萘基苯并噁唑分子设计与光物理性质的研究%Molecular design and photophysic properties investigation of novel nitrogen heteroatom 2-beta-naphthyl-benzoxazoles

    Institute of Scientific and Technical Information of China (English)

    冯玉玲; 孙京国; 张之佩

    2002-01-01

    为了寻找新的有效光敏材料,设计了一系列新型氮杂2-β萘基苯并眂唑分子,用改进的PPP-SCF-CI方法,对设计分子的第一激发单线态、三线态、振子强度和跃迁矩等光物理性质进行了较为详细的研究.筛选出了一些新型的具有特殊光物理特性的分子,并预测了有可能产生新型氮杂2-β萘基苯并眂唑分子类光敏感功能材料的取代基部位.

  1. Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

    OpenAIRE

    Almeida, P; Reis, L. V.; SANTOS, P.F.; Ramos, S. S.; Pardal, A. C.

    2002-01-01

    The synthesis and spectroscopic characterisation of some representative N-alkylsubstituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzoselenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine dyes.

  2. Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

    Directory of Open Access Journals (Sweden)

    P. Almeida

    2002-03-01

    Full Text Available The synthesis and spectroscopic characterisation of some representative N-alkylsubstituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzoselenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine dyes.

  3. Fluorescent compounds for plastic scintillation applications

    Energy Technology Data Exchange (ETDEWEB)

    Pla-Dalmau, A.; Bross, A.D.

    1994-04-01

    Several 2-(2{prime}-hydroxyphenyl)benzothiazole, -benzoxazole, and -benzimidazole derivatives have been prepared. Transmittance, fluorescence, light yield, and decay time characteristics of these compounds have been studied in a polystyrene matrix and evaluated for use in plastic scintillation detectors. Radiation damage studies utilizing a {sup 60}C source have also been performed.

  4. Crystal Structure and Molecular Mechanics Modelling of 2-(4-Amino-3-benzyl-2-thioxo-2,3-dihydrothiazol-5-ylbenzoxazole

    Directory of Open Access Journals (Sweden)

    Ahmed F. Mabied

    2014-01-01

    Full Text Available The crystal structure of the title compound, 2-(4-amino-3-benzyl-2-thioxo-2,3-dihydrothiazol-5-ylbenzoxazole, was determined. The crystal has P1 space group and triclinic system with unit cell parameters a = 5.174(3 Å, b = 6.411(6 Å, c = 12.369(10 Å, α = 86.021(4°, β = 84.384(5°, and γ = 77.191(5°. The structure consists of benzoxazole group connected with benzyl via thiazole (attached with amino and thione. Benzoxazole and thiazole rings are almost planar (maximum deviation at C1, −0.013(3 Å, and C10, 0.0041(3 Å, resp.. The phenyl ring is nearly perpendicular to both thiazole and benzoxazole rings. A network of intermolecular hydrogen bonds and intermolecular interactions stabilizes the structure, forming parallel layers. The molecular geometry obtained using single crystal analysis is discussed along with results of the molecular mechanics modeling (MM, and the results showed the same cis conformation between benzoxazole nitrogen atom and the amino group.

  5. ZSM-5催化一锅法合成3-(5’-取代-2’-苯并噁唑基)-7-二乙基氨基-2H-1-苯并吡喃-2-酮%One-Pot Synthesis of 3-(5'-Subsituted-benzoxazol-2'-yl)-7-diethyl-amino-chromen-2-one Catalyzed with ZSM-5

    Institute of Scientific and Technical Information of China (English)

    蒋绍亮; 韩亮

    2012-01-01

    3-(5'-Subsituted-benzooxazol-2'-yl)-7-diethylamino-chromen-2-ones were prepared by one-pot three-component reaction of 4-diethylaminosalicylaldehydes, ethyl cyanoacetate and o-aminophenols in refluxing rc-butanol catalyzed by ZSM-5. This method has advantages of better yields and more environment-friendly process compared with that catalyzed by liquid catalysts.%以绿色环保的固体酸ZSM-5分子筛为催化剂,正丁醇为溶剂,4-位取代邻氨基苯酚、4-二乙氨基水杨醛和氰乙酸乙酯三组分一锅法合成了香豆素类化合物3-(5’-取代-2’-苯并噁唑基)-7-二乙基氨基-2H-1-苯并吡喃-2-酮.与液体酸催化相比,该方法具有收率更高、环境友好等优点.

  6. Laser generation in vapors of complex molecules at 330 to 350 nm

    Energy Technology Data Exchange (ETDEWEB)

    Borisevich, N.A.; Gorelenko, A.Ya.; Kazak, N.S.; Kalosha, I.I.; Morgun, Yu.F.; Agashkov, A.V.; Tolkachev, V.A.; Tugbaev, V.A.

    1980-02-01

    In pumping by a the fourth harmonic neodymium laser, the lasing has been produced in the vapours of 1,4-di(1-(4-ethyl)phenyl)-benzene (I), 1,4-di(n-phenylethynly)-benzene (II), 2-(n-butoxyphenyl)-benzoxazole (III) and 2-(n-hexadecyloxyphenyl)benzoxazole (IV). In order to reduce the lasing threshold, foreign gases (propane and pentane) were used. The wave lengths of the band centers, pressures of the foreign gas and temperatures amounted respectively to: I-335.5 nm, 15 atm, 160/sup 0/C; II-349.5 nm, 55 atm, 127/sup 0/C; III-337.5 nm, 55 atm, 127/sup 0/C; IV-339 nm, 65 atm, 132/sup 0/C. Lasing has been produced in shorter wave region and at lower temperatures than in the gas phase of the active compounds reported earlier.

  7. Syntheses and electroluminescent properties of two europium ternary complexes Eu(DBM){sub 3}(PBO) and Eu(DBM){sub 3}(PBT)

    Energy Technology Data Exchange (ETDEWEB)

    Guan Min [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China); Gao Lihua [Department of Chemistry, Beijing Normal University, Beijing 100875 (China); Wang Shanshan [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China); Huang Chunhui [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China)], E-mail: chhuang@pku.edu.cn; Wang Kezhi [Department of Chemistry, Beijing Normal University, Beijing 100875 (China)

    2007-12-15

    Two europium complexes, Eu(DBM){sub 3}(PBO) and Eu(DBM){sub 3}(PBT) (DBM=dibenzoylmethanato, PBO=2-(2-pyridyl)benzoxazole, PBT=2-(2-pyridyl)benzothiazole), were prepared and used as emitting materials in organic electroluminescent (EL) devices. The devices with the structures ITO/TPD/Eu(DBM){sub 3}(PBO) (or Eu(DBM){sub 3}(PBT)/BCP/Alq{sub 3}/Mg:Ag/Ag emit red light originating from the europium complexes.

  8. Design, synthesis and antitumor activity of 3-substituted quinolone derivatives (Ⅰ)

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    A series of quinolone derivatives containing benzimidazole, benzoxazole or benzothiazole ring were synthesized. The cytotoxicity of 12 new compounds was evaluated in KB, Be17402, A2780 and HT-29 cell lines. Most of synthesized compounds showed moderate inhibitory activity against cancer cells. The inhibitory activities of 6k, against KB and A2780 tumor cells are comparable to that of topotecan, one of topoisomerase I inhibitors.

  9. Two novel fluorescent calix[4]arene derivatives with benzoazole units in 1,3-alternate conformation for selective recognition to Fe~(3+) and Cr~(3+)

    Institute of Scientific and Technical Information of China (English)

    He Wen Wang; Ya Qing Feng; Chen Chen; Jin Qiang Xue

    2009-01-01

    Two novel fluorescent calix[4]arene derivatives 1a and 1b with benzoxazole or benzothiazole units in 1,3-alternate conformation have been synthesized and characterized by IR, ~1H NMR, ~(13)C NMR and MS. Their complexation properties to different heavy and transition metal ions have been studied by UV-vis spectroscopy and fluorescence spectrometer. Compounds la and lb show selective recognition to Fe~(3+) and Cr~(3+).

  10. Methodology for detecting residual phosphoric acid in polybenzoxazole fibers.

    Science.gov (United States)

    Park, Eun Su; Sieber, John; Guttman, Charles; Rice, Kirk; Flynn, Kathleen; Watson, Stephanie; Holmes, Gale

    2009-12-01

    Because of the premature failure of in-service soft-body armor containing the ballistic fiber poly[(benzo-[1,2-d:5,4-d']-benzoxazole-2,6-diyl)-1,4-phenylene] (PBO), the Office of Law Enforcement Standards (OLES) at the National Institute of Standards and Technology (NIST) initiated a research program to investigate the reasons for this failure and to develop testing methodologies and protocols to ensure that these types of failures do not reoccur. In a report that focused on the stability of the benzoxazole ring that is characteristic of PBO fibers, Holmes, G. A.; Rice, K.; Snyder, C. R. J. Mater. Sci. 2006, 41, 4105-4116, showed that the benzoxazole ring was susceptible to hydrolytic degradation under acid conditions. Because of the processing conditions for the fibers, it is suspected by many researchers that residual phosphoric acid may cause degradation of the benzoxazole ring resulting in a reduction of ballistic performance. Prior to this work, no definitive data have indicated the presence of phosphoric acid since the residual phosphorus is not easily extracted and the processed fibers are known to incorporate phosphorus containing processing aids. Methods to efficiently extract phosphorus from PBO are described in this article. Further, characterization determined that the majority of the extractable phosphorus in PBO was attributed to the octyldecyl phosphate processing aid with some phosphoric acid being detected. Analysis by matrix assisted laser desorption ionization of model PBO oligomers indicates that the nonextractable phosphorus is attached to the PBO polymer chain as a monoaryl phosphate ester. The response of model aryl phosphates to NaOH exposure indicates that monoaryl phosphate ester is stable to NaOH washes used in the manufacturing process to neutralize the phosphoric acid reaction medium and to extract residual phosphorus impurities.

  11. Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

    OpenAIRE

    Eduardo Soriano; Cory Holder; Andrew Levitz; Maged Henary

    2015-01-01

    Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural ch...

  12. Protonation and strong H-bonding as the factors controlling structural changes in excited azaaromatics

    Energy Technology Data Exchange (ETDEWEB)

    Grabowska, A. (Polska Akademia Nauk, Warsaw. Inst. Chemii Fizycznej)

    1981-11-01

    The relationship between the structure of a molecule and electron density distribution in excited states of protonated N-heteroaromatics has been discussed, basing on (1) Walsh rules (2) dihydroflavines as model compounds. Two selected examples of inter- and intramolecular proton transfer have been quoted, namely the net charge distribution in 7-azaindole and proton transfer kinetics in 2(2'-hydroxyphenyl)benzoxazole.

  13. Rh(I)–Bisphosphine-Catalyzed Asymmetric, Intermolecular Hydroheteroarylation of α-Substituted Acrylate Derivatives

    Science.gov (United States)

    2015-01-01

    Asymmetric hydroheteroarylation of alkenes represents a convenient entry to elaborated heterocyclic motifs. While chiral acids are known to mediate asymmetric addition of electron-rich heteroarenes to Michael acceptors, very few methods exploit transition metals to catalyze alkylation of heterocycles with olefins via a C–H activation, migratory insertion sequence. Herein, we describe the development of an asymmetric, intermolecular hydroheteroarylation reaction of α-substituted acrylates with benzoxazoles. The reaction provides 2-substitued benzoxazoles in moderate to excellent yields and good to excellent enantioselectivities. Notably, a series of mechanistic studies appears to contradict a pathway involving enantioselective protonation of a Rh(I)–enolate, despite the fact that such a mechanism is invoked almost unanimously in the related addition of aryl boronic acids to methacrylate derivatives. Evidence suggests instead that migratory insertion or beta-hydride elimination is enantiodetermining and that isomerization of a Rh(I)–enolate to a Rh(I)–heterobenzyl species insulates the resultant α-stereocenter from epimerization. A bulky ligand, CTH-(R)-Xylyl-P-Phos, is crucial for reactivity and enantioselectivity, as it likely discourages undesired ligation of benzoxazole substrates or intermediates to on- or off-cycle rhodium complexes and attenuates coordination-promoted product epimerization. PMID:25545834

  14. Intramolecular proton transfer and tunnelling reactions of hydroxyphenylbenzoxazole derivatives in Xenon at 15 K

    Energy Technology Data Exchange (ETDEWEB)

    Walla, Peter J. [Max-Planck-Institute for Biophysical Chemistry, Department 010, Spectroscopy and Photochemical Kinetics, Am Fassberg 11, D-37077 Goettingen (Germany) and Department for Biophysical Chemistry, Technical University of Brunswick, Institute for Physical and Theoretical Chemistry, Hans-Sommerstr. 10, D-38106 Braunschweig (Germany)]. E-mail: pwalla@gwdg.de; Nickel, Bernhard [Max-Planck-Institute for Biophysical Chemistry, Department 010, Spectroscopy and Photochemical Kinetics, Am Fassberg 11, D-37077 Goettingen (Germany)

    2005-06-06

    We investigated the site dependence and the tunnelling processes of the intramolecular proton and deuteron transfer in the triplet state of the compounds 2-(2'-hydroxy-4'-methylphenyl)benzoxazole (m-MeHBO) and 2-(2'-hydroxy-3'-methylphenyl)benzoxazoles (o-MeHBO) and their deuterio-oxy analogues in a solid xenon matrix. After singlet excitation there occurs an ultrafast intramolecular enol {yields} keto proton transfer and subsequent intersystem crossing mainly to the keto triplet state. In the triplet state of m-MeHBO, the proton transfer back to the lower enol triplet state is governed by tunnelling processes. In o-MeHBO, however, the enol triplet state is higher and therefore normally no tunnel reaction can be observed. Because of the external heavy atom-effect in a xenon matrix, we were able to investigate the reverse enol-keto-tunnelling after exciting directly the enol triplet state of deuterated o-MeHBO. The time constants of the reverse enol-keto tautomerization are similar to those of the normal keto-enol tautomerization. In a xenon matrix, the observed site-selective phosphorescence spectra are very well-resolved vibrationally. This allowed the study of the tunnel rates in different well-defined sites. The vibrational energies obtained in the spectra are in good agreement with vibrational energies found in resonant Raman and IR spectra of 2-(2'-hydroxyphenyl)benzoxazole (HBO)

  15. Insights on the binding of thioflavin derivative markers to amyloid fibril models and Aβ{sub 1-40} fibrils from computational approaches

    Energy Technology Data Exchange (ETDEWEB)

    Alí-Torres, Jorge; Rimola, Albert; Sodupe, Mariona [Departament de Química, Universitat Autònoma de Barcelona, Bellaterra 08193 (Spain); Rodriguez-Rodríguez, Cristina [Medicinal Inorganic Chemistry Group, Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1 (Canada)

    2014-10-06

    The present contribution analyzes the binding of ThT and neutral ThT derivatives to a β-sheet model by means of quantum chemical calculations. In addition, we study the properties of four molecules: (2-(2-hydroxyphenyl)benzoxazole (HBX), 2-(2-hydroxyphenyl)benzothiazole (HBT) and their respective iodinated compounds, HBXI and HBTI, in binding to amyloid fibril models and Aβ{sub 1-40}fibrils by using a combination of docking, molecular dynamics and quantum mechanics calculations.

  16. Ti (IV complexes of some heterocyclic ligands. Synthesis, characterization and ethylene polymerization activity

    Directory of Open Access Journals (Sweden)

    Hamdi Ali Elagab

    2016-03-01

    Full Text Available 31 complexes of bis - (benzimidazole, benzothiazole and benzoxazole compounds with Ti (IV metal centers were synthesized, characterized, activated with methylalumoxane (MAO and then tested for catalytic ethylene polymerization. The activities of the various catalysts were found to be functions of the hetero atoms in the ligand frameworks. The highest activity was obtained with 39 / MAO (573 kg PE / mol cat. h. The produced polyethylenes showed high molecular weights (up to 1.5 ×106 g/mol and broad molecular weight distributions (PD = 65. This could result from different interactions of the MAO counterion with the heteroatoms of the catalyst ligand generating different active sites.

  17. Cyclopalladated Ferrocenylimine Catalyzed Chlorination of 2-Arylbenzoxazoles%Cyclopalladated Ferrocenylimine Catalyzed Chlorination of 2-Arylbenzoxazoles

    Institute of Scientific and Technical Information of China (English)

    冷瑜婷; 杨帆; 吴养洁; 李克

    2011-01-01

    An efficient and facile protocol for palladacycle-catalyzed chlorination of 2-arylbenzoxazoles was developed. The results represent the first examples involving the palladacycle as the catalyst for such chlorination. This chlori- nation was not a ligand-directed ortho-C--H activation, but an electrophilic substitution process at the para-position of the nitrogen atom in the benzo ring of benzoxazole moiety, the regiochemistry of which had been confirmed by HMBC spectral analysis. The catalytic system could tolerate various halogen atoms, such as F, Cl and Br, affording the corresponding products in moderate to excellent yields.

  18. PALS investigations of free volumes thermal expansion of J-PET plastic scintillator synthesized in polystyrene matrix

    CERN Document Server

    Wieczorek, A; Jasińska, B; Gorgol, M; Bednarski, T; Białas, P; Czerwiński, E; Gajos, A; Kamińska, D; Kapłon, Ł; Kochanowski, A; Korcyl, G; Kowalski, P; Kozik, T; Krzemień, W; Kubicz, E; Niedźwiecki, S; Pałka, M; Raczyński, L; Rudy, Z; Rundel, O; Sharma, N G; Silarski, M; Słomski, A; Strzelecki, A; Wiślicki, W; Zieliński, M; Moskal, P

    2015-01-01

    The polystyrene dopped with 2,5-diphenyloxazole as a primary fluor and 2-(4-styrylphenyl)benzoxazole as a wavelength shifter, prepared as a plastic scintillator was investigated using positronium probe in wide range of temperatures from 123 to 423 K. Three structural transitions at 260 K, 283 K and 370 K were found in the material. In the o-Ps intensity dependence on temperature, the significant hysteresis is observed. Heated to 370 K, the material exhibits the o-Ps intensity variations in time.

  19. BOXTO as a real-time thermal cycling reporter dye

    Indian Academy of Sciences (India)

    Ashraf I Ahmad

    2007-03-01

    The unsymmetrical cyanine dyes BOXTO (4-[6-(benzoxazole-2-yl-(3-methyl-)-2,3-dihydro-(benzo-1,3-thiazole)-2-methylidene)]-1-methyl-quinolinium chloride) and its positive divalent derivative BOXTO-PRO (4-[(3-methyl-6-(benzoxazole-2-yl)-2,3-dihydro-(benzo-1,3-thiazole)-2-methylidene)]-1-(3-trimethylammonium-propyl)-quinolinium dibromide) were studied as real-time PCR reporting fluorescent dyes and compared to SYBR GREEN I (SG) (2-[N-(3-dimethylaminopropyl)-N-propylamino]-4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl)-methylidene]-1-phenyl-quinolinium). Unmodified BOXTO showed no inhibitory effects on real-time PCR, while BOXTO-PRO showed complete inhibition. Sufficient fluorescent signal was acquired when 0.5–1.0 M BOXTO was used with RotorGene and iCycler platforms. Statistical analysis showed that there is no significant difference between the efficiency and dynamic range of BOXTO and SG. BOXTO stock solution (1.5 mM) was stable at –20°C for more than one year and 40 M BOXTO solution was more stable than 5x SG when both were stored at 4°C for 45 days.

  20. Synthesis and evaluation of mutual azo prodrug of 5-aminosalicylic acid linked to 2-phenylbenzoxazole-2-yl-5-acetic acid in ulcerative colitis

    Directory of Open Access Journals (Sweden)

    Jilani JA

    2013-07-01

    Full Text Available Jamal A Jilani,1 Maha Shomaf,2 Karem H Alzoubi3 1Department of Medicinal Chemistry and Pharmacognosy, Jordan University of Science and Technology, Irbid, Jordan; 2Department of Pathology, Jordan University, Amman, Jordan; 3Department of Clinical Pharmacy, Jordan University of Science and Technology, Irbid, Jordan Abstract: In this study, the syntheses of 4-aminophenylbenzoxazol-2-yl-5-acetic acid, (an analogue of a known nonsteroidal anti-inflammatory drug [NSAID] and 5-[4-(benzoxazol-2-yl-5-acetic acidphenylazo]-2-hydroxybenzoic acid (a novel mutual azo prodrug of 5-aminosalicylic acid [5-ASA] are reported. The structures of the synthesized compounds were confirmed using infrared (IR, hydrogen-1 nuclear magnetic resonance (1H NMR, and mass spectrometry (MS spectroscopy. Incubation of the azo compound with rat cecal contents demonstrated the susceptibility of the prepared azo prodrug to bacterial azoreductase enzyme. The azo compound and the 4-aminophenylbenzoxazol-2-yl-5-acetic acid were evaluated for inflammatory bowel diseases, in trinitrobenzenesulfonic acid (TNB-induced colitis in rats. The synthesized diazo compound and the 4-aminophenylbenzoxazol-2-yl-5-acetic acid were found to be as effective as 5-aminosalicylic acid for ulcerative colitis. The results of this work suggest that the 4-aminophenylbenzoxazol-2-yl-5-acetic acid may represent a new lead for treatment of ulcerative colitis. Keywords: benzoxazole acetic acid, azo prodrug, colon drug delivery

  1. Smart synthesis of high performance thermosets based on ortho-(amide-co-imide functional benzoxazines

    Directory of Open Access Journals (Sweden)

    Hatsuo eIshida

    2015-02-01

    Full Text Available High performance thermosets via amide-imide functional benzoxazine resins as precursors have been synthesized. The structures of synthesized monomers have been confirmed by 1H NMR and FT-IR. Among these two benzoxazine monomers, the ortho-amide-imide functional benzoxazine resin shows powerful features both in the synthesis of benzoxazine monomers and the properties of the corresponding thermosets. For the cross-linked poly(amide-co-imide based on ortho-amide-imide functional benzoxazine, a smart route is adopted to develop a more thermally stable cross-linked poly(benzoxazole-co-imide. Besides, the poly(benzoxazole-co-imide can also undergo a further thermal treatment to form polybenzoxazole. Furthermore, a main-chain type ortho-functional polybenzoxazine with amide-co-imide and benzoxazine groups as repeating units has also been prepared. Both the ortho-amide-imide functional benzoxazine and main-chain type polybenzoxazine resins show the possibility to form high performance thermosets with low cost and easy processability .

  2. National Institute for Petroleum and Energy Research quarterly technical report, January 1--March 31, 1990

    Energy Technology Data Exchange (ETDEWEB)

    1990-04-19

    Fuels research is discussed in the following areas: (1) Department of Analytical Methodology for Analysis of Heavy Crudes; and (2) thermochemistry and thermophysical properties of organic nitrogen-, and diheteroatom-containing compounds. This quarter for project (1), inspection analysis of five 1000{degree}F+ resids employed in the carbonization study were completed. Also, subfractionation of Cerro Negro neutrals fraction was carried out. Progress on Project 2 consisted of: a thermodynamic analysis for the key hydrogen-consuming steps in the hydrodenitrogenation (HDN) reaction network for quinoline; heat-capacity and enthalpy measurements were completed for the diheteroatom-containing compound, thianthrene. Following completion measurements on thianthrene, the heat capacity of the empty calorimeter was determined, and in another calorimeter, heat-capacity and enthalpy studies were started on benzoxazole. Methods to convert benzoxazole to its low-temperature form were developed, and measurements were completed between 80 and 240 K; and high-temperature heat capacities were determined for phenoxathin and carbazole. 1 ref., 14 figs., 11 tabs.

  3. HPLC/FLD测定聚酯纤维纺织品中9种非离子荧光增白剂%Determination of nine non-ionic fluorescent whitening agent residues in polyester fibre textile by HPLC/FLD

    Institute of Scientific and Technical Information of China (English)

    吴晓琼; 丁友超; 汤娟; 徐海; 郑丹丹

    2016-01-01

    建立了纺织品中DT、SWN、OB、KSN、ER-Ⅰ、ER-Ⅱ、KCB、OB-Ⅰ、OB-Ⅱ9种非离子荧光增白剂(FWAs)的前处理方法以及高效色谱荧光检测(HPLC/FLD)方法。样品经二甲苯提取、浓缩、定容后,进行HPLC/FLD定性定量分析。采用Phenomenex Gemini 5u C18(150 mm×4.6 mm,5μm)色谱柱进行分离,以乙腈-2.5 mmol/L乙酸铵溶液为流动相,梯度洗脱。9种非离子FWAs的相关系数均不小于0.9993,定量下限(LOQs,S/N=10)为0.70~0.95 mg/kg。不同添加水平下,9种非离子FWAs的回收率为83.0%~100%,相对标准偏差(RSDs)为4.0%~8.8%。该方法简单、灵敏度高,具有一定的实际应用价值。%A sample pertreatment coupled to high performance with fluorescent detector (HPLC/FLD) method was developed for determination of nine non-ionic fluorescent whitening agents, including 1,2-bis(5-methyl-2-benzoxazole)ethylene (DT), 7-diethylamino-4-methylcoumarin (SWN), 2,2′-(2,5-thiophenedi⁃yl)bis[5-(1,1-dimethylethyl)-benzoxazol] (OB), 2-[4-[2-[4-(2-benzoxazolyl)phenyl]ethenyl]phenyl]-5-methyl-benzoxazol (KSN), 1,4-bis(2-cyano styryl)benzene (ER-Ⅰ), 1-(2-cyano styryl)-4-1-(2-cyano styryl)-4-(4-cy⁃ano styryl) benzene (ER-Ⅱ), 2,2′-(1,4-naphthalenediyl)bis-benzoxazol (KCB), 4,4′-bis[2-(2-methoxyphenyl) ethenyl]-1′-biphenyl (OB-Ⅰ), 2,2′-(1,2-ethenediyldi-4,1-phenylene)bis(5-methyl-benzoxazol) (OB-Ⅱ) in textile. The sample was extracted with xylene and concentrated, and then qualitatively and quantitatively ana⁃lyzed by HPLC/FLD. The separation of target compounds was performed on a phenomenex Gemini 5u C18 (150 mm × 4.6 mm,5 μm) column by gradient elution using acetonitrile/ammonium acetate solution (containing 2.5 mmol/L ammonium acetate) as mobile phase. The correlation coefficients of nine kinds of non-ionic fluo⁃rescent whitening agents was not less than 0.999 3. The limits of quantification of the nine compounds (LOQs, S/N=10) were 0

  4. Behavior of a fenhexamid photoproduct during the alcoholic fermentation of Saccharomyces cerevisiae.

    Science.gov (United States)

    Cabras, Paolo; Farris, Giovanni A; Pinna, Maria V; Pusino, Alba

    2004-12-29

    The fungicide fenhexamid [N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide] degraded rapidly by UV or sunlight irradiation, yielding 7-chloro-6-hydroxy-2-(1-methylcyclohexyl)-1,3-benzoxazole (CHB) as a main photoproduct. CHB was isolated, and its effect on alcoholic fermentation of Saccharomyces cerevisiae was studied. The results indicate that the presence of CHB does not affect the extent of alcohol production. After 12 days, the amount of CHB in the fermentation medium decreased by ca. 65%. Only 25% of the missing CHB was recovered unchanged from yeasts, most likely because it was adsorbed on the yeast wall cell. The remaining part degraded during the fermentation process. Glucan and chitin, two potential adsorbents, which constitute yeast cell walls, exhibited affinity for CHB.

  5. Inhibition of copper corrosion in aerated hydrochloric acid solution by heterocyclic compounds containing a mercapto group

    Energy Technology Data Exchange (ETDEWEB)

    Zhang Daquan; Gao Lixin; Zhou Guoding

    2004-12-01

    Inhibition of copper corrosion by benzotriazole (BTA), 2-mercapto benzoxazole (MBO) and 2-mercapto benzimidazole (MBI) in 0.5 mol L{sup -1} HCl was investigated by weight-loss measurements, potentiodynamic polarization curves and electrochemical impedance spectroscopy. MBI was shown to be the most effective inhibitor among those tested. Potentiodynamic polarization results revealed that the three compounds acted as anodic inhibitors, particularly MBI strongly suppressed anodic current densities. Molecular structure parameters of BTA, MBO and MBI were obtained by using an MM2 forcefield program and PPP-SCF quantum chemical calculation. It was found that MBI has higher levels of HOMO and LUMO energy and the larger {pi}-electron density.

  6. Introduction of fluorin into PBO polymer chains:Toward higher thermal stability and lower dielectric constant

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    A series of novel fluorinated benzoxazole polymers (6FPBO’s) with high thermal stability and low dielectric constant were synthesized by copolymerization of 1,3-diamino-4, 6-dihydroxybenzene dihy-drochloride (DAR), 1,4-benzenedicarboxylic acid (PTA) and various amount of 4’4- (hexafluoroisopro-pylidene) bis (benzoic acid) (BIS-B-AF) in the medium of polyphosphoric acid (PPA). 6FPBO fibers were then obtained via dry-jet wet-spinning technique and characterized by means of Fourier transform infrared (FTIR) spectra, thermogravimetric analysis (TGA), single fiber tensile testing machine and scanning electron microscopy (SEM). FTIR spectrum of 6FPBO fibers indicated that the fluorine groups had been incorporated into PBO molecular chains successfully. TGA curves revealed that 6FPBO fibers possessed high thermal stability just as pure PBO fibers. Moreover, dielectric constant spectrum of 6FPBO exhibited that the polymers had low dielectric constant, especially in the range of high- frequency.

  7. Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties.

    Science.gov (United States)

    Soriano, Eduardo; Holder, Cory; Levitz, Andrew; Henary, Maged

    2015-12-24

    Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.

  8. Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

    Directory of Open Access Journals (Sweden)

    Eduardo Soriano

    2015-12-01

    Full Text Available Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.

  9. New Fluorescence Probes for Biomolecules

    Directory of Open Access Journals (Sweden)

    Katarzyna Jurek

    2015-07-01

    Full Text Available Steady state fluorescence measurements have been used for the investigation of interaction between the bovine serum albumin (BSA and fluorescence probes: 3-hydroxy-2,4- bis[(3-methyl-1,3-benzoxazol-2(3H-ylidenemethyl]cyclobut-2-en-1-one (SQ6, 3-hydroxy- 2,4-bis[(3-methyl-1,3-benzothiazol-2(3H-ylidenemethyl]cyclobut-2-en-1-one (SQ7 and 3-hydroxy-2,4-bis[(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidenemethyl]cyclobut-2-en-1-one (SQ8. The binding constant between bovine serum albumin and squarine dyes has been determined by using both the Benesi-Hildebrand and Stern-Volmer equations. The negative value of free energy change indicates the existence of a spontaneous complexation process of BSA with squarine dyes.

  10. Syntheses of 2- or 6-Substituted Chromones and Chromone Ring-opening Reaction in Polyphosphoric Acid

    Institute of Scientific and Technical Information of China (English)

    HE Xun-gui; YOU Qi-dong; LI Zhi-yu

    2004-01-01

    In an attempt to find new antitumor agents, a novel class of chromone compounds with a benzimidazole or a benzoxazole ring in positions 2 or 6 were synthesized via condensation in polyphosphoric acid(PPA) by using chromone acids as the starting materials. During the preparation process, it was found that PPA could cleave the chromone ring to produce a ring-opening compound(6). The molar ratio of the chromone compound(5) to the ring-opening compound(6) varied with the change of reaction temperature and time. Based on MTT protocol, the antitumor activity of each of the compounds obtained was evaluated against three human cancer cell lines: KB(oral epidermal), A2780(ovary) and Bel7402(liver). The IC50 varied from 54.7 μmol/L to more than 180 μmol/L.

  11. XPS study of PBO fiber surface modified by incorporation of hydroxyl polar groups in main chains

    Energy Technology Data Exchange (ETDEWEB)

    Zhang Tao; Hu Dayong; Jin Junhong; Yang Shenglin [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 201620 (China); Li Guang, E-mail: lig@dhu.edu.cn [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 201620 (China); Jiang Jianming [State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 201620 (China)

    2010-01-15

    Dihydroxy poly(p-phenylene benzobisoxazole) (DHPBO), a modified poly(p-phenylene benzoxazole) (PBO) polymer containing double hydroxyl groups in polymer chains, was synthesized by copolymerization of 4,6-diamino resorcinol dihydrochloride (DAR), purified terephthalic acid (TA) and 2,5-dihydroxyterephthalic acid (DHTA). DHPBO fibers were prepared by dry-jet wet-spinning method. The effects of hydroxyl polar groups on the surface elemental compositions of PBO fiber were investigated by X-ray photoelectron spectroscopy (XPS). The results show that the ratio of oxygen/carbon on the surface of DHPBO fibers is higher than that on the surface of PBO fibers, which indicates the content of polar groups on the surface of DHPBO fiber increase compared with PBO fiber.

  12. FY 2000 report on the results of the R and D of the fusion domain. Volume 2. Chemo-intelligence; 2000 nendo yugo ryoiki kenkyu kaihatsu. 2. Kemo intelligence

    Energy Technology Data Exchange (ETDEWEB)

    NONE

    2001-03-01

    For the purpose of developing materials with excellent functions by design/synthesis of molecules/molecular aggregates with biological functions, study was made, and the FY 2000 results were reported. In the basic study of intermolecular interactions, analysis was made of the directional dependence of hydrogen bond, CH-(pai),NH-(pai) and OH-(pai) interactions. In the study of the design and synthesis of macrocyclic host molecules, a method for phased change of ether oxygen to OH group was found out, and new macrocyclic host molecules with 3 or 4 hydroxy groups were obtained. In the study of the synthesis and properties of ligands for synthesis and functional development of metal complexes, compounds having both phenolic hydroxy groups and benzoxazole moieties were synthesized by the Claisen rearrangement. In the study of the structuring of novel supermolecular systems, it was found out that 25-membered ring crownophane made super-molecule with pseudorotaxane by reaction with organic ammonium salts. (NEDO)

  13. Synthesis and properties of polybenzazoles containing flexible methylene in backbone

    Institute of Scientific and Technical Information of China (English)

    Xiaohui XU; Xiaoyun LIU; Chengjun ZHOU; Qixin ZHUANG; Zhewen HAN

    2008-01-01

    A novel series of polybenzazoles with rigid-rod benzoxazole cycle and soft methylene segment was designed and synthesized via solution condensation poly-merizations from 4,6-diamino-l,3-benzenediol dipho-sphate, terephthalic acid and aliphatic dicarboxylic acid. The structures of polybenzazoles were characterized by means of FT-IR,1H NMR and Wide-angle X-ray diffrac-tion (WAXRD). All the polymers show excellent thermal stability and the TdS was above 471℃, The intrinsic vis-cosities [η] of the polymers ranged from 0.8 to 0.9. The UV-Vis absorption peaks of the polymers in MSA were blue-shifted from 429 nm for PBO to 291 nm for PBOC7, and the Stokes shifts in PL spectra enlarged.

  14. Selective blue emission from an HPBO-Li{sup +} complex in alkaline media

    Energy Technology Data Exchange (ETDEWEB)

    Obare, S.O.; Murphy, C.J. [South Carolina Univ., Dept. of Chemistry and Biochemistry, Graduate Science Research Center, Columbia, SC (United States)

    2001-12-01

    Li{sup +} sensors are currently in demand for monitoring Li{sup +} transport in Li{sup +} batteries. Fluorescent receptors specific for metal ions are desirable since they allow both direct and real-time detection. Here we show that 2-(2-Hydroxyphenyl)benzoxazole(HPBO) exhibits enhanced fluorescence and specificity for Li{sup +} compared to Na{sup +} and K{sup +}, in an alkaline medium. The selectivity was observed in several organic solvents in the presence of bases such as pyridine, triethylamine and trimethyl-amine. HPBO-Li{sup +} complex formation results in an intense blue emission readily observed by the naked eye under UV light. Spectroscopic titrations suggest that the structure of the complex is one in which two HPBO anionic ligands coordinate to one Li{sup +}, with a second Li{sup +} as a counter-ion. (authors)

  15. New heterocycles having double characters; as antimicrobial and surface active agents.

    Directory of Open Access Journals (Sweden)

    El-Sayed, R.

    2004-12-01

    Full Text Available Fatty acids isothiocyanate (1 was used as a starting material to synthesize some important heterocycles such as triazoles, oxazoles, thiazoles, benzoxazoles and quinazolines by treating with different types of nucleophiles such as nitrogen nucleophiles, oxygen nucleophiles, and sulfur nucleophiles. The produced compounds were subjected to propylene oxide in different moles (n = 3, 5 and 7 to produce novel groups of nonionic compounds having the double function as antimicrobial and surface active agents which can be used in the manufacturing of drugs, cosmetics, pesticides or can be used as antibacterial and/or antifungal. The physical properties as surface and interfacial tension, cloud point, foaming height, wetting time, emulsification power and the critical micelle concentration (CMC were determined, antimicrobial and biodegradability were also determined.Isocianatos de acidos grasos se utilizaron como material de partida para la síntesis de importantes heterociclos tales como triazoles, oxazoles, thoazoles, benzoxazoles y quinazolinas mediante el tratamiento de los mismos con diferentes tipos de nucleofilos tales como nucleofilos nitrogenados, oxigenados, o azufrados. Los compuestos producidos se trataron con oxido de propileno a diferentes concentraciones molares (n = 3, 5 y 7 para producir nuevos grupos de compuestos no iónicos que tuvieran la doble función de ser compuestos antimicrobianos y agentes de superficie, que se pudieran usar en la fabricación de medicinas, cosméticos, pesticidas o como antibacterianos o antifúngicos. Se determinaron sus propiedades tales como tensión superficial e interfacial, punto de turbidez, altura de espuma, tiempo de mojado, poder de emulsificación y concentración micelar crítica (CMC, asi como sus propiedades antimicrobianas y de degradabilidad.

  16. Synthesis of benzothiazole derivatives%苯并噻唑类衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    巨修练; 杨诗宏

    2013-01-01

    Heterocyclic compounds are becoming a research focus in drug development field with wide range of biological activity, low toxicity, high efficiency, environmental friendship and diverse structures. 5-chloro-2-benzoxazole ketone (chlorzoxazone) which is a nicotinic acetylcholine receptor antagonist was appliecl as a lead. The oxygen atom of the structure of 5-chloro-2-benzoxazole ketone was replaced by sulfur atom. Then a series of 5-chloro-2-benzothiazole derivatives were designed by the principle of bioisosterism and new structure of nicotinic acetylcholine receptor antagonists was developed. 5-chloro-2-benzothiazole ketones were synthesized by the reaction of 4-chloride-2-amino benzene mercaptan and urea, finally six phenylethanolamine benzothiazole derivatives were prepared followed by nucleophilic substitution with a series of halogenated hydrocarbon. All target compounds were characterized by 1HNMR, MS spectra. The biological activities of these compounds need further investigation.%由于杂环化合物具有广泛的生物活性,且具低毒、高效、对环境友好、结构多样化等多种优点,已成为当今药物开发的热点.以烟碱乙酰胆碱受体拮抗剂5-氯-2-苯并噁唑酮(商品名氯唑杀宗,chlorzoxazone)为先导,依据电子等排原理,将5-氯-2-苯并噁唑酮变换为以5-氯-2-苯并噻唑酮,设计了一系列5-氯-2-苯并噻唑酮衍生物,以期开发具有新型结构的烟碱乙酰胆碱受体拮抗剂.在合成方面,以4-氯-2-氨基苯硫醇为起始原料与脲素在酸性条件下闭环反应生成中间体5-氯-2-苯并噻唑酮,该中间体经重结晶纯化后,在碱性条件下,与一系列带有良好生物活性基团的卤代烃发生亲核取代,合成了六个未见文献报道的苯并噻唑衍生物,所有化合物均经过MS、[1H]NMR进行了结构表征,其生物活性有待研究.

  17. Imaging of amyloid deposition in human brain using positron emission tomography and [{sup 18}F]FACT: comparison with [{sup 11}C]PIB

    Energy Technology Data Exchange (ETDEWEB)

    Ito, Hiroshi [National Institute of Radiological Sciences, Molecular Imaging Center, Chiba (Japan); National Institute of Radiological Sciences, Biophysics Program, Molecular Imaging Center, Chiba (Japan); Shinotoh, Hitoshi; Shimada, Hitoshi; Miyoshi, Michie; Takano, Harumasa; Takahashi, Hidehiko; Arakawa, Ryosuke; Kodaka, Fumitoshi; Ono, Maiko; Eguchi, Yoko; Higuchi, Makoto; Fukumura, Toshimitsu; Suhara, Tetsuya [National Institute of Radiological Sciences, Molecular Imaging Center, Chiba (Japan); Yanai, Kazuhiko; Okamura, Nobuyuki [Tohoku University School of Medicine, Department of Pharmacology, Sendai (Japan)

    2014-04-15

    The characteristic neuropathological changes in Alzheimer's disease (AD) are deposition of amyloid senile plaques and neurofibrillary tangles. The {sup 18}F-labeled amyloid tracer, [{sup 18}F]2-[(2-{(E)-2-[2-(dimethylamino)-1,3-thiazol-5-yl]vinyl}-1, 3-benzoxazol-6-yl)oxy ]-3-fluoropropan-1-ol (FACT), one of the benzoxazole derivatives, was recently developed. In the present study, deposition of amyloid senile plaques was measured by positron emission tomography (PET) with both [ {sup 11}C ]Pittsburgh compound B (PIB) and [ {sup 18}F ]FACT in the same subjects, and the regional uptakes of both radiotracers were directly compared. Two PET scans, one of each with [ {sup 11}C ]PIB and [ {sup 18}F ]FACT, were performed sequentially on six normal control subjects, two mild cognitive impairment (MCI) patients, and six AD patients. The standardized uptake value ratio of brain regions to the cerebellum was calculated with partial volume correction using magnetic resonance (MR) images to remove the effects of white matter accumulation. No significant differences in the cerebral cortical uptake were observed between normal control subjects and AD patients in [ {sup 18}F ]FACT studies without partial volume correction, while significant differences were observed in [ {sup 11}C ]PIB. After partial volume correction, the cerebral cortical uptake was significantly larger in AD patients than in normal control subjects for [ {sup 18}F ]FACT studies as well as [ {sup 11}C ]PIB. Relatively lower uptakes of [ {sup 11}C ]PIB in distribution were observed in the medial side of the temporal cortex and in the occipital cortex as compared with [ {sup 18}F ]FACT. Relatively higher uptake of [ {sup 11}C ]PIB in distribution was observed in the frontal and parietal cortices. Since [ {sup 18}F ]FACT might bind more preferentially to dense-cored amyloid deposition, regional differences in cerebral cortical uptake between [ {sup 11}C ]PIB and [ {sup 18}F ]FACT might be due to differences

  18. Synthesis of Some New Heterocycles Derived from Phenylacetyl Isothiocyanate

    Institute of Scientific and Technical Information of China (English)

    HEMDAN M.M.; FAHMY A.F.; ALI N.F.; HEGAZI E.; ABD-ELHALEEM A.

    2008-01-01

    Phenylacetyl isothiocyanate (1) was reacted with benzoyl hydrazine (2a) in acetonitrile to give thiosemicarbazide derivative 3 which was cyclized by polyphosphoric acid to give 1,2,4-triazoline-5-thione derivative 4.Treatment of 1 with thiosemicarbazide (2b) yielded another 1,2,4-triazoline-5-thione derivative 5.Similar treatment of 1 with phenyl hydrazine (2c) in acetonitrile gave a differently substituted 1,2,4-triazoline-5-thione derivative 6 in one pot-reaction.On the other hand, when the reaction was carried out in acetone, a mixture of 6 and thiadiazolidine derivative 7 was obtained.However, reaction of 1 with hydrazine hydrate (2d) gave hydrazine derivative 8.Reaction of isothiocyanate 1 with anthranilic acid (9) gave benzo[d][1,3,6]oxazin-1-one derivative 10.Treatment of 1 with 2-aminothiophenol (11a), 2-aminophenol (11b) or o-phenylenediamine (11c) produced benzothiazole derivative 12a, benzoxazole derivative 12b and benzimidazole derivative 12c, respectively.The structures of all the products were confirmed by micro-analytical and spectral data.

  19. 3-D QSAR CoMFA study of nitrogen mustards possessing new chemical entities as possible anticancer agents

    Directory of Open Access Journals (Sweden)

    Anand R

    2006-01-01

    Full Text Available This present work is an investigation of anticancer activities of the nitrogen mustards possessing quinazolinone, benzimidazole, benzoxazole, and benzothiazole nuclei by the three-dimensional Quantitative Structure Activity paradigm, Comparative Molecular Field Analysis. A total of 39 compounds were modelled in SYBYL 6.7 (Tripos, USA. The molecules were aligned by root-mean-square fit of atoms and field fit of the steric and electrostatic molecular fields and the resulting databases analysed by partial least squares analysis with cross-validation, leave-one-out and no validation to extract the optimum number of components. The analysis was then repeated with bootstrapping to give the final Quantitative Structure Activity Relationship models. Eight compounds, which were kept separately as test set, were used to test the predictive ability of the Comparative Molecular Field Analysis models. Out of the two models generated, one was found to be useful. The predicted activities of the test set were in good agreement with experimentally determined values.

  20. Synthesis and antitumor activity evaluation of new 2-(4-aminophenyl)benzothiazole derivatives bearing different heterocyclic rings.

    Science.gov (United States)

    Yurttaş, Leyla; Tay, Funda; Demirayak, Şeref

    2015-06-01

    Twenty-five new N-[4-(benzothiazole-2-yl)phenyl]acetamide derivatives bearing different heterocyclic ring systems were synthesized using 2-(4-aminophenyl)benzothiazole structure as a pharmacophoric group. Final compounds were screened for their potential antitumor activity in vitro against approximately 60 human tumor cell lines derived from nine neoplastic diseases at National Cancer Institute, USA. 2-(4-Aminophenyl)benzothiazole structure was prepared by the reaction of 4-aminobenzoic acid and 2-aminothiophenol in polyphosphoric acid using microwave irradiation. After acetylation reaction, amide compounds 2a and 2b were obtained, which were then reacted with 2-mercapto(benz)imidazole/benzothiazole/benzoxazole derivatives in acetone with the presence of potassium carbonate to gain final compounds (3-27). Among all tested compounds, compound 10, namely N-[4-(benzothiazole-2-yl)-3-chlorophenyl]-2-[(benzimidazole-2-yl)thio]acetamide, and compound 16, namely N-[4-(benzothiazole-2-yl)phenyl]-2-[(1,5-diphenyl-1H-imidazole-2-yl)thio]acetamide, were found to be of considerable anticancer activity against some cancer cell lines.

  1. {beta} - amyloid imaging probes

    Energy Technology Data Exchange (ETDEWEB)

    Jeong, Jae Min [Seoul National University College of Medicine, Seoul (Korea, Republic of)

    2007-04-15

    Imaging distribution of {beta} - amyloid plaques in Alzheimer's disease is very important for early and accurate diagnosis. Early trial of the {beta} -amyloid plaques includes using radiolabeled peptides which can be only applied for peripheral {beta} - amyloid plaques due to limited penetration through the blood brain barrier (BBB). Congo red or Chrysamine G derivatives were labeled with Tc-99m for imaging {beta} - amyloid plaques of Alzheimer patient's brain without success due to problem with BBB penetration. Thioflavin T derivatives gave breakthrough for {beta} - amyloid imaging in vivo, and a benzothiazole derivative [C-11]6-OH-BTA-1 brought a great success. Many other benzothiazole, benzoxazole, benzofuran, imidazopyridine, and styrylbenzene derivatives have been labeled with F-18 and I-123 to improve the imaging quality. However, [C-11]6-OH-BTA-1 still remains as the best. However, short half-life of C-11 is a limitation of wide distribution of this agent. So, it is still required to develop an Tc-99m, F-18 or I-123 labeled agent for {beta} - amyloid imaging agent.

  2. 2-Benzazolyl-4-Piperazin-1-Ylsulfonylbenzenecarbohydroxamic Acids as Novel Selective Histone Deacetylase-6 Inhibitors with Antiproliferative Activity.

    Directory of Open Access Journals (Sweden)

    Lei Wang

    Full Text Available We have screened our compound collection in an established cell based assay that measures the derepression of an epigenetically silenced transgene, the locus derepression assay. The screen led to the identification of 4-[4-(1-methylbenzimidazol-2-ylpiperazin-1-yl]sulfonylbenzenecarbohydroxamic acid (9b as an active which was found to inhibit HDAC1. In initial structure activity relationships study, the 1-methylbenzimidazole ring was replaced by the isosteric heterocycles benzimidazole, benzoxazole, and benzothiazole and the position of the hydroxamic acid substituent on the phenyl ring was varied. Whereas compounds bearing a para substituted hydroxamic acid (9a-d were active HDAC inhibitors, the meta substituted analogues (8a-d were appreciably inactive. Compounds 9a-d selectively inhibited HDAC6 (IC50 = 0.1-1.0 μM over HDAC1 (IC50 = 0.9-6 μM and moreover, also selectively inhibited the growth of lung cancer cells vs. patient matched normal cells. The compounds induce a cell cycle arrest in the S-phase while induction of apoptosis is neglible as compared to controls. Molecular modeling studies uncovered that the MM-GBSA energy for interaction of 9a-d with HDAC6 was higher than for HDAC1 providing structural rationale for the HDAC6 selectivity.

  3. A SAR study of novel antiproliferative ruthenium and osmium complexes with quinoxalinone ligands in human cancer cell lines.

    Science.gov (United States)

    Ginzinger, Werner; Mühlgassner, Gerhard; Arion, Vladimir B; Jakupec, Michael A; Roller, Alexander; Galanski, Markus; Reithofer, Michael; Berger, Walter; Keppler, Bernhard K

    2012-04-12

    A series of ruthenium(II) arene complexes with 3-(1H-benzimidazol-2-yl)-1H-quinoxalin-2-one, bearing pharmacophoric groups of known protein kinase inhibitors, and related benzoxazole and benzothiazole derivatives have been synthesized. In addition, the corresponding osmium complexes of the unsubstituted ligands have also been prepared. The compounds have been characterized by NMR, UV-vis, and IR spectroscopy, ESI mass spectrometry, elemental analysis, and by X-ray crystallography. Antiproliferative activity in three human cancer cell lines (A549, CH1, SW480) was determined by MTT assays, yielding IC(50) values of 6-60 μM for three unsubstituted metal-free ligands, whereas values for the metal complexes vary in a broad range from 0.3 to 140 μM. Complexation with osmium of quinoxalinone derivatives with benzimidazole or benzothiazole results in a more consistent increase in cytotoxicity than complexation with ruthenium. For selected compounds, the capacity to induce apoptosis was confirmed by fluorescence microscopy and flow-cytometric analysis, whereas cell cycle effects are only moderate.

  4. 2-Benzazolyl-4-Piperazin-1-Ylsulfonylbenzenecarbohydroxamic Acids as Novel Selective Histone Deacetylase-6 Inhibitors with Antiproliferative Activity.

    Science.gov (United States)

    Wang, Lei; Kofler, Marina; Brosch, Gerald; Melesina, Jelena; Sippl, Wolfgang; Martinez, Elisabeth D; Easmon, Johnny

    2015-01-01

    We have screened our compound collection in an established cell based assay that measures the derepression of an epigenetically silenced transgene, the locus derepression assay. The screen led to the identification of 4-[4-(1-methylbenzimidazol-2-yl)piperazin-1-yl]sulfonylbenzenecarbohydroxamic acid (9b) as an active which was found to inhibit HDAC1. In initial structure activity relationships study, the 1-methylbenzimidazole ring was replaced by the isosteric heterocycles benzimidazole, benzoxazole, and benzothiazole and the position of the hydroxamic acid substituent on the phenyl ring was varied. Whereas compounds bearing a para substituted hydroxamic acid (9a-d) were active HDAC inhibitors, the meta substituted analogues (8a-d) were appreciably inactive. Compounds 9a-d selectively inhibited HDAC6 (IC50 = 0.1-1.0 μM) over HDAC1 (IC50 = 0.9-6 μM) and moreover, also selectively inhibited the growth of lung cancer cells vs. patient matched normal cells. The compounds induce a cell cycle arrest in the S-phase while induction of apoptosis is neglible as compared to controls. Molecular modeling studies uncovered that the MM-GBSA energy for interaction of 9a-d with HDAC6 was higher than for HDAC1 providing structural rationale for the HDAC6 selectivity.

  5. The effects of coagulants on the structure of PBO materials

    Institute of Scientific and Technical Information of China (English)

    LI Jin-huan; HUANG Yu-dong; MENG Lin

    2006-01-01

    PBO materials possess super mechanical properties and high thermal and chemical resistance due to their special rigid-rod backbones with heterocyclic chemical structure and supermolecular microstructure. But these structures may be affected by a series of preparing technologies, among which the coagulant is even more important. In this paper the chemical and microstructure changes of PBO materials coagulated with different solvents were investigated. Analyses of molecular weight and chemical structure of PBO coagulated indicate that the heterocyclic ring of PBO will experience cleavage in coagulation and in this stage water plays an important role. The final structure of PBO materials may involve several intermediate structures lying between benzoxazole and the open ring. Wide-angle X-ray diffraction (WAXD) 2θ scans and scanning probe microscope (SPM) show that the microstructure of PBO materials coagulated in solvents with different properties will change a lot and those coagulants with the smaller rate of diffusion like methanol can cause more ordered molecule alignment containing fewer voids.

  6. Strong Fluorescent Smart Organogel as a Dual Sensing Material for Volatile Acid and Organic Amine Vapors.

    Science.gov (United States)

    Xue, Pengchong; Yao, Boqi; Wang, Panpan; Gong, Peng; Zhang, Zhenqi; Lu, Ran

    2015-11-23

    An L-phenylalanine derivative (C12PhBPCP) consisting of a strong emission fluorophore with benzoxazole and cyano groups is designed and synthesized to realize dual responses to volatile acid and organic amine vapors. The photophysical properties and self-assembly of the said derivative in the gel phase are also studied. C12PhBPCP can gelate organic solvents and self-assemble into 1 D nanofibers in the gels. UV/Vis absorption spectral results show H-aggregate formation during gelation, which indicates strong exciton coupling between fluorophores. Both wet gel and xerogel emit strong green fluorescence because the cyano group suppresses fluorescence quenching in the self-assemblies. Moreover, the xerogel film with strong green fluorescence can be used as a dual chemosensor for quantitative detection of volatile acid and organic amine vapors with fast response times and low detection limits owing to its large surface area and amplified fluorescence quenching. The detection limits are 796 ppt and 25 ppb for gaseous aniline and trifluoroacetic acid (TFA), respectively.

  7. Photoluminescent mixed ligand complexes of CuX (X = Cl, Br, I) with PPh3 and a polydentate imino-pyridyl ligand - Syntheses, structural variations and catalytic property

    Science.gov (United States)

    Ghorai, Anupam; Mondal, Jahangir; Patra, Goutam K.

    2015-10-01

    Three ternary copper(I) complexes [CuI2Cl2(L1)(PPh3)4] (1), [CuI2Br2(L1) (PPh3)4] (2) and [CuI2(μ-I)2 (μ-L1) (PPh3)2]n (3) have been prepared by reactions of CuX (X = Cl, Br and I) with PPh3 and the polydentate imino-pyridyl ligand L1. These complexes have been characterized by elemental analysis, IR, UV-Vis, NMR and X-ray crystallography. From single crystal structural analysis it has been found that complexes 1 and 2 are homo-dinuclear having non-bridging halide ions whereas complex 3 is a 1-D zig-zag co-ordination polymer containing bridged iodide ions. Complexes 1, 2 and 3 are photoluminescent at room temperature in chloroform whereas ligand L1 is non-emissive. The E½ values of the CuIsbnd CuII couple of 1, 2 and 3 are 0.98 V, 0.92 V and 0.42 V respectively (vs Ag/AgCl in 1 M KCl, scan rate 100 mV s-1). All three complexes function as effective catalysts for the synthesis of 2-substituted benzoxazoles.

  8. Introduction of fluorin into PBO polymer chains:Toward higher thermal stability and lower dielectric constant

    Institute of Scientific and Technical Information of China (English)

    ZHANG Tao; HU DaYong; JIN JunHong; YANG ShengLin; LI Guang; JIANG JianMing

    2009-01-01

    A series of novel fluorinated benzoxazole polymers (6FPBO's) with high thermal stability and low di-electric constant were synthesized by copolymerization of 1,3-diamino-4, 6-dihydroxybenzene dihy-drochloride (DAR), 1,4-benzenedicarboxylic acid (PTA) and various amount of 4'4- (hexafluoroisopro-pylidene) bis (benzoic acid) (BIS-B-AF) in the medium of polyphosphoric acid (PPA). 6FPBO fibers were then obtained via dry-jet wet-spinning technique and characterized by means of Fourier transform in-flared (FTIR) spectra, thermogravimetric analysis (TGA), single fiber tensile testing machine and scan-ning electron microscopy (SEe). FTIR spectrum of 6FPBO fibers indicated that the fluorine groups had been incorporated into PBO molecular chains successfully. TGA curves revealed that 6FPBO fibers possessed high thermal stability just as pure PBO fibers. Moreover, dielectric constant spectrum of 6FPBO exhibited that the polymers had low dielectric constant, especially in the range of high-fre-quency.

  9. Benzothiazoles: how relevant in cancer drug design strategy?

    Science.gov (United States)

    Singh, Meenakshi; Singh, Sushil K

    2014-01-01

    Heterocyclic compounds, analogs and derivatives have attracted attention due to their diverse biological and pharmacological properties. Benzoheterocycles such as benzothiazoles, benzimidazoles and benzoxazoles are constituents of many bioactive heterocyclic compounds, having wider range of applications. They have been extensively studied for their biological activities, and can serve as unique and versatile scaffolds for drug design. The benzothiazole, in the family of heterocyclic compounds has assumed special significance in synthetic chemistry, pharmaceutical chemistry as well as in clinical applications because of its anti-tumor properties. This review is organized in the following ways. It begins with brief introduction on the chemical diversity of synthetic analogs of benzothiazole. After this, drug design strategy and mechanisms of action through its diverse biological targets in which benzothiazole and its derivatives display their anticancer activity are discussed. It ends with the metabolism pattern of benzothiazole and its analogs. Analysis of the structure-activity relationships (SAR), quantitative structure-activity relationships (QSAR) as well as on docking studies of this family of compounds highlights the potential that may lead to the development of novel anticancer agents. Such relationships will definitely create lot of interest among the researchers to synthesize optimized variety of benzothiazole derivatives and to screen them for their anticancer activity.

  10. QSAR study of heparanase inhibitors activity using artificial neural networks and Levenberg-Marquardt algorithm.

    Science.gov (United States)

    Jalali-Heravi, M; Asadollahi-Baboli, M; Shahbazikhah, P

    2008-03-01

    A linear and non-linear quantitative structure-activity relationship (QSAR) study is presented for modeling and predicting heparanase inhibitors' activity. A data set that consisted of 92 derivatives of 2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid, furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acids is used in this study. Among a large number of descriptors, four parameters classified as physico-chemical, topological and electronic indices are chosen using stepwise multiple regression technique. The artificial neural networks (ANNs) model shows superiority over the multiple linear regressions (MLR) by accounting 87.9% of the variances of antiviral potency of the heparanase inhibitors. This paper focuses on investigating the role of weight update functions in developing ANNs. Levenberg-Marquardt (L-M) algorithm shows a better performance compared with basic back propagation (BBP) and conjugate gradient (CG) algorithms. The accuracy of 4-3-1 L-M ANN model was illustrated using leave-one-out (LOO), leave-multiple-out (LMO) cross-validations and Y-randomization. The mean effect of descriptors and sensitivity analysis show that log P is the most important parameter affecting the inhibitory behavior of the molecules.

  11. Hydroxy-substituted polyenaminonitrile as a soluble precursor for rigid-rod polybenzoxazole

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Ji Heung; Lee, Jae Kwan [Sungkyunkwan Univ., Suwon (Korea, Republic of)

    2001-09-01

    (1-Chloro-2,2-dicyanovinyl)benzene or 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene was reacted with 2-amino-phenol to give the model compound, hydroxy enaminonitrile, which was found to undergo thermal cyclization reaction to form the corresponding benzoxazole. This intramolecular cyclization reaction is expected to occur through nucleophilic attack to electropositive enamine carbon by ortho-hydroxy group on the phenyl ring, which is accompanied by the release of neutral malononitrile through rearrangement. From each bifunctional monomer, o-hydroxy substituted polyenaminonitrile was prepared and characterized as a new precursor polymer for well-known aromatic polybenzoxazole. Also the unusual macrocyclic dimer formation from the 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane polymerization reaction system was discussed. The thermal cyclization reactions and the properties of polymers were investigated using FR-IR and thermal analysis (DSC and TGA)

  12. Improved performance of organic light-emitting diodes using a Zn complex

    Energy Technology Data Exchange (ETDEWEB)

    Jang, Yoon-Ki; Kim, Dong-Eun; Kwon, Oh-Kwan; Kwon, Young-Soo [Dong-A University, Busan (Korea, Republic of); Kim, Won-Sam; Lee, Burm-Jong [Inje University, Gimhae (Korea, Republic of)

    2006-09-15

    We have synthesized new electroluminescence materials, including [2-(2-hydroxyphenyl) benzoxazole] (Zn(HPB){sub 2}) and [(1,10-phenanthroline)(8-hydroxyquinoline)] Zn(phen)q. The photoluminescence (PL) spectra of Zn(HPB){sub 2} and Zn(phen)q were observed to be blue and yellowish green, respectively. The ionization potential (IP) and the electron affinity (EA) of each Zn complex were measured using cyclic voltammetry (CV). Zn(HPB){sub 2} was used as an emitting material while Zn(phen)q and Alq{sub 3} were used as electron transport materials. We investigated the electron transport properties of Zn(phen)q compared with Alq{sub 3}. The fundamental structures of the organic lightemitting diodes (OLEDs) were ITO/NPB/Zn(HPB){sub 2}/Zn(phen)q and Alq{sub 3}/LiF/Al. As a result, the electron transport properties of Zn(phen)q were better than those of Alq{sub 3}. Therefore, Zn(phen)q should be useful as an electron transport material to enhance the performance of OLEDs.

  13. Detecting local heterogeneity and ionization ability in the head group region of different lipidic phases using modified fluorescent probes

    Science.gov (United States)

    Abou-Zied, Osama K.; Zahid, N. Idayu; Khyasudeen, M. Faisal; Giera, David S.; Thimm, Julian C.; Hashim, Rauzah

    2015-01-01

    Local heterogeneity in lipid self-assembly is important for executing the cellular membrane functions. In this work, we chemically modified 2-(2′-hydroxyphenyl)benzoxazole (HBO) and attached a C8 alkyl chain in two different locations to probe the microscopic environment of four lipidic phases of dodecyl β-maltoside. The fluorescence change in HBO and the new probes (HBO-1 and HBO-2) shows that in all phases (micellar, hexagonal, cubic and lamellar) three HBO tautomeric species (solvated syn-enol, anionic, and closed syn-keto) are stable. The formation of multi tautomers reflects the heterogeneity of the lipidic phases. The results indicate that HBO and HBO-1 reside in a similar location within the head group region, whereas HBO-2 is slightly pushed away from the sugar-dominated area. The stability of the solvated syn-enol tautomer is due to the formation of a hydrogen bond between the OH group of the HBO moiety and an adjacent oxygen atom of a sugar unit. The detected HBO anions was proposed to be a consequence of this solvation effect where a hydrogen ion abstraction by the sugar units is enhanced. Our results point to a degree of local heterogeneity and ionization ability in the head group region as a consequence of the sugar amphoterism. PMID:25731606

  14. Emissive polymeric materials for optoelectronic devices

    Science.gov (United States)

    Shiang, Joseph John; Chichak, Kelly Scott; Cella, James Anthony; Lewis, Larry Neil; Janora, Kevin Henry

    2011-07-05

    Polymers including at least one structural unit derived from a compound of formula I or including at least one pendant group of formula II may be used in optoelectronic devices ##STR00001## wherein R.sup.1, R.sup.3, R.sup.4 and R.sup.6 are independently hydrogen, alkyl, alkoxy, oxaalkyl, alkylaryl, aryl, arylalkyl, heteroaryl, substituted alkyl; substituted alkoxy, substituted oxaalkyl, substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted heteroaryl; R.sup.1a is hydrogen or alkyl; R.sup.2 is alkylene, substituted alkylene, oxaalkylene, CO, or CO.sub.2; R.sup.2a is alkylene; R.sup.5 is independently at each occurrence hydrogen, alkyl, alkylaryl, aryl, arylalkyl, alkoxy, carboxy, substituted alkyl; substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted alkoxy, X is halo, triflate, --B(OR.sup.1a).sub.2, or ##STR00002## located at the 2, 5- or 2, 7-positions; and L is derived from phenylpyridine, tolylpyridine, benzothienylpyridine, phenylisoquinoline, dibenzoquinozaline, fluorenylpyridine, ketopyrrole, 2-(1-naphthyl)benzoxazole)), 2-phenylbenzoxazole, 2-phenylbenzothiazole, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, phenylimine, vinylpyridine, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, phenylindole, derivatives thereof or combinations thereof.

  15. Studies on biodegradation and molecular characterization of 2,4-D Ethyl Ester and Pencycuron induced Cyanobacteria by using GC-MS and 16S rDNA sequencing

    Directory of Open Access Journals (Sweden)

    J. I. Nirmal Kumar

    2013-03-01

    Full Text Available GC-MS study and molecular characterization by 16S rDNA amplification were carried out to evaluate differential effects of 2,4-D ethyl ester and pencycuron on Anabaena fertilissima, Aulosira fertilissima and Westiellopsis prolifica. Each organism has its own capacity to degrade both pesticides into various subgroups depending largely upon the main functional group of each individual pesticide. Hence, different subgroups like 2,4-D methyl ester, 2,4-D isobutyl ester, Isobutyric acid allyl ester, 3-Bromobutyric acid, 2,4-D butyl ester, Hydroxyurea, Trifluroacetic acid, 2-Methyl propyl ester, Acetic acid 2-propenyl ester and Acetic acid (2,3-dichlorophenoxy were transformed from 2,4-D ethyl ester while Benzoxazole was the only compound generated from pencycuron treated W. prolifica. The results obtained by 16S rDNA sequencing confirmed that 16S rDNA region of Anabaena fertilissima was more affected by 2,4-D ethyl ester as there was no homology in the region of 39 basepairs, in addition, several mismatches and gaps were observed, whereas less difference in 16S rDNA was observed in case of Aulosira fertilissima and W. prolific on forth day. However, there was no significant change in the sequence of 16S rDNA pattern of all the three test organisms after 16-days of exposure to pencycuron treatment.

  16. High pressure optical studies of crystalline anils and related compounds

    Energy Technology Data Exchange (ETDEWEB)

    Hockert, E.N.; Drickamer, H.G.

    1977-12-01

    High pressure optical studies have been made on a series of crystalline therochromic and photochromic anils and model compounds. Measurements include absorption and emission peak locations and the integrated intensities of various absorption peaks including the uv peak and visible peaks introduced thermally or by irradiation at various temperatures and pressures. Emission yields were also obtained. For the thermochromic compounds there was a large increase in the equilibrium yield of the thermally induced peak with pressure (piezochromism), corresponding to a volume decrease of approx.1.2 cc/mole for 5-bromosalicylidene aniline (5BrSA). The emission peak shifts to lower energy and decreases in intensity primarily because of increased rate of the radiationless conversion. For salicylidene aniline and related photochromic crystals the rate of photochromic conversion varied with both pressure and temperature in a manner which depends on the size of the energy barriers to the forward and reverse processes. The emission yield increases with pressure at low pressure, goes through a maximum, and decreases at high pressure. At low pressure the dominant feature is increase in occupation of the emitting state while at high pressure the increased rate of the radiationless process governs. For 2- (O-hydroxyphenyl) benzoxazole (OHBO) (see Fig. 1), where a keto--enol rearrangement is most probable, the changes in absorption and emission intensity can be related to the same diagram used for the anils. This diagram also describes the behavior of benzilidene aniline (BA), where only a cis--trans isomerization is possible.

  17. Improvement of color purity in white OLED based on Zn(HPB){sub 2} as blue emitting layer

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Dong-Eun [Department of Electrical Engineering and NTRC, Dong-A University, Busan, 604-714 (Korea, Republic of); Kim, Won-Sam [Department of Chemistry and Institute of Functional Materials, Inje University, Gimhae, 621-749 (Korea, Republic of); Kim, Byoung-Sang [Department of Electrical Engineering and NTRC, Dong-A University, Busan, 604-714 (Korea, Republic of); Lee, Burm-Jong [Department of Chemistry and Institute of Functional Materials, Inje University, Gimhae, 621-749 (Korea, Republic of); Kwon, Young-Soo [Department of Electrical Engineering and NTRC, Dong-A University, Busan, 604-714 (Korea, Republic of)], E-mail: yskwon@dau.ac.kr

    2008-04-01

    We synthesized zinc (II) [2-(2-hydroxyphenyl)benzoxazole] (Zn(HPB){sub 2}) as blue emitting materials and evaluated in the organic light emitting diodes (OLEDs). The layer of Zn(HPB){sub 2} doped with 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) (Zn(HPB){sub 2}:DCJTB) as emitters has been demonstrated. The structure of the device is indium-tin-oxide (ITO)/N,N'-bis-(1-naphthl)-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB, 40 nm)/Zn(HPB){sub 2}/Zn(HPB){sub 2}:DCJTB/Alq{sub 3} (20 nm)/LiF/Al. The thickness of Zn(HPB){sub 2} layer was 0, 10, 20, 30 nm at the same time the thickness of Zn(HPB){sub 2}:DCJTB layer were 40, 30, 20, 10 nm. When thickness of Zn(HPB){sub 2} layer was 30 nm and the thickness of Zn(HPB){sub 2}:DCJTB layer was 10 nm, white emission is achieved. The Commission Internationale de l'Eclairage (CIE) coordinates of the white emission are (0.304, 0.332) at an applied voltage of 10.5 V.

  18. Rapid detection of eight fluorescent whitening agents in textile by ultra performance convergence chromatography%超高效合相色谱法快速检测纺织品中的8种荧光增白剂

    Institute of Scientific and Technical Information of China (English)

    汤娟; 丁友超; 曹锡忠; 齐琰; 钱凯

    2014-01-01

    An accurate quantitative and confirmative method has been developed for the deter-mination of eight fluorescent whitening agents(FWAs)in textile by ultra performance conver-gence chromatography( UPC 2 )coupled with photo diode array( PDA)detection,including 1,2-bis(5-methyl-2-benzoxazole)ethylene( PF),7-diethylamino-4-methylcoumarin( SWN),2, 2′-(2,5-thiophenediyl)bis( 5-( 1,1-dimethylethyl)-benzoxazol( OB),2-[ 4-[ 2-[ 4-( 2-benzox-azolyl)phenyl]ethenyl]phenyl]-5-methyl-benzoxazol( KSN),1,4-bis(2-cyanostyryl)benzene (ER-Ⅰ),1-(2-cyanostyryl)-4-( 4-cyanostyryl)benzene( ER-Ⅱ),2,2′-( 1,4-naphthalenediyl) bis-benzoxazol(KCB),4,4′-bis[2-(2-methoxyphenyl)ethenyl]-1,1′-biphenyl( FP). The sam-ple was extracted with xylene and concentrated by a rotary evaporator,and then qualitatively and quantitatively analyzed by UPC 2 . The separation of target compounds was achieved on an ACQUITY UPC 2 HSS C18 SB column(100 mm × 3. 0 mm,1. 8 μm)by a gradient elution with supercritical carbon dioxide and methanol as mobile phases. External standard method was used for the quantitative determination and the calibration curves showed good linearity in the concentration range of 1. 0 - 20.0 mg / L for the eight target compounds with correlation coeffi-cients not less than 0. 999 1. The limits of quantification of the eight compounds(LOQs,S / N =10)were 0. 70-0. 95 mg / L. The average recoveries of the eight compounds ranged from 90. 9%to 96. 5% at the spiked levels of 2. 0,5. 0,10. 0 mg / kg with the relative standard deviations (RSDs)of 2. 8% -4. 2% . The method is simple,accurate and time-saving with high sensitivity, and can be used for the rapid determination of the eight FWAs in textile.%建立了同时检测纺织品中1,2-双(5-甲基-2-苯并恶唑基)-乙烯(PF)、7-二乙氨基-4-甲基香豆素(SWN)、2,2′-(2,5-二苯基硫代)双[5-(1,1-二甲基乙基)]苯并恶唑( OB)、2-[4-[2-[4-(2-苯并恶唑基)苯基]乙烯基]苯基]-5

  19. Synthesis and Properties of Poly[p-(2,5-dihydroxy- phenylenebenzobisoxazole] Fiber

    Directory of Open Access Journals (Sweden)

    Hong Lin

    2008-11-01

    Full Text Available The novel polymer poly[p-(2,5-dihydroxy-phenylenebenzobisoxazole] (PBOH fiber was synthesized in the presence of 2,5-dihydroxyterephthalicacid (DHTA and 4,6-diamino-1,3-benzenediol in poly(phosphoric acid (PPA using typical polycondensation conditions. The crystalline solutions of liquid PBOH in PPA were spun into fibers using dry-jet wet spinning. Furthermore, the thermostability and mechanical properties of PBOH were compared with poly(p-phenylene-2,6-benzoxazole (PBO in order to investigate the relationship between the chain structure and properties. The results indicated that the thermal degradation temperature of PBOH was above 750K and the tensile strength of the PBOH fiber was 3.1GPa, which were much lower than those of PBO fiber. The compressive strength of PBOH fiber was 331 M Pa, which was slightly higher than that of PBO fiber. In addition, molecular simulation was employed to explain why the compressive strength of PBOH fiber did not increase significantly compared to PBO fiber.

  20. 2-Benzazolyl-4-Piperazin-1-Ylsulfonylbenzenecarbohydroxamic Acids as Novel Selective Histone Deacetylase-6 Inhibitors with Antiproliferative Activity

    Science.gov (United States)

    Wang, Lei; Kofler, Marina; Brosch, Gerald; Melesina, Jelena; Sippl, Wolfgang; Martinez, Elisabeth D.; Easmon, Johnny

    2015-01-01

    We have screened our compound collection in an established cell based assay that measures the derepression of an epigenetically silenced transgene, the locus derepression assay. The screen led to the identification of 4-[4-(1-methylbenzimidazol-2-yl)piperazin-1-yl]sulfonylbenzenecarbohydroxamic acid (9b) as an active which was found to inhibit HDAC1. In initial structure activity relationships study, the 1-methylbenzimidazole ring was replaced by the isosteric heterocycles benzimidazole, benzoxazole, and benzothiazole and the position of the hydroxamic acid substituent on the phenyl ring was varied. Whereas compounds bearing a para substituted hydroxamic acid (9a-d) were active HDAC inhibitors, the meta substituted analogues (8a-d) were appreciably inactive. Compounds 9a-d selectively inhibited HDAC6 (IC50 = 0.1–1.0μM) over HDAC1 (IC50 = 0.9–6μM) and moreover, also selectively inhibited the growth of lung cancer cells vs. patient matched normal cells. The compounds induce a cell cycle arrest in the S-phase while induction of apoptosis is neglible as compared to controls. Molecular modeling studies uncovered that the MM-GBSA energy for interaction of 9a-d with HDAC6 was higher than for HDAC1 providing structural rationale for the HDAC6 selectivity. PMID:26698121

  1. Redox effects and cytotoxic profiles of MJ25 and auranofin towards malignant melanoma cells

    Science.gov (United States)

    Drummond, Catherine J.; McCarthy, Anna R.; Higgins, Maureen; Campbell, Johanna; Brodin, Bertha; Arnér, Elias S.J.; Laín, Sonia

    2015-01-01

    Malignant melanoma is the most dangerous type of skin cancer. Although recent progress in treatment has been achieved, lack of response, drug resistance and relapse remain major problems. The tumor suppressor p53 is rarely mutated in melanoma, yet it is inactive in the majority of cases due to dysregulation of upstream pathways. Thus, we screened for compounds that can activate p53 in melanoma cells. Here we describe effects of the small molecule MJ25 (2-{[2-(1,3-benzothiazol-2-ylsulfonyl)ethyl]thio}-1,3-benzoxazole), which increased the level of p53-dependent transactivation both as a single agent and in combination with nutlin-3. Furthermore, MJ25 showed potent cytotoxicity towards melanoma cell lines, whilst having weaker effects against human normal cells. MJ25 was also identified in an independent screen as an inhibitor of thioredoxin reductase 1 (TrxR1), an important selenoenzyme in the control of oxidative stress and redox regulation. The well-characterized TrxR inhibitor auranofin, which is FDA-approved and currently in clinical trials against leukemia and a number of solid cancers, displayed effects comparable with MJ25 on cells and led to eradication of cultured melanoma cells at low micromolar concentrations. In conclusion, auranofin, MJ25 or other inhibitors of TrxR1 should be evaluated as candidate compounds or leads for targeted therapy of malignant melanoma. PMID:26029997

  2. Electron beam damage in high temperature polymers

    Energy Technology Data Exchange (ETDEWEB)

    Kumar, S. (Dayton Univ., OH (USA). Research Inst.); Adams, W.W. (Air Force Materials Lab., Wright-Patterson AFB, OH (USA))

    1990-01-01

    Electron microscopic studies of polymers are limited due to beam damage. Two concerns are the damage mechanism in a particular material, and the maximum dose for a material before damage effects are observed. From the knowledge of the dose required for damage to the polymer structure, optimum parameters for electron microscopy imaging can be determined. In the present study, electron beam damage of polymers has been quantified by monitoring changes in the diffraction intensity as a function of electron dose. The beam damage characteristics of the following polymers were studied: poly(p-phenylene benzobisthiazole) (PBZT); poly(p-phenylene benzobisoxazole) (PBO); poly(benzoxazole) (ABPBO); poly(benzimidazole) (ABPBI); poly(p-phenylene terephthalamide) (PPTA); and poly(aryl ether ether ketone) (PEEK). Previously published literature results on polyethylene (PE), polyoxymethylene (POM), nylon-6, poly(ethylene oxide) (PEO), PBZT, PPTA, PPX, iPS, poly(butylene terephthalate) (PBT), and poly(phenylene sulphide) (PPS) were reviewed. This study demonstrates the strong dependence of the electron beam resistivity of a polymer on its thermal stability/melt temperature. (author).

  3. Monophthalocyanine complexes of samarium and terbium with axial ligands:synthesis, structure and optoelectronic properties

    Institute of Scientific and Technical Information of China (English)

    Alexander A Maleev; Mikhail N Bochkarev; Anatoly P Pushkarev; Vasily A Ilichev; Mikhail A Lopatin; Maxim A Samsonov; Georgy K Fukin; Georgy L Pakhomov; Vladislav V Travkin; Ivan D Grishin

    2014-01-01

    The monophthalocyanine complexes of samarium and terbium containing axial 2-mercaptobenzothiazole (PcSm(MBT) (1)), 2-(2-benzoxazol-2-yl) phenolate (PcTb(OON) (2)) or 2-(2-benzothiazol-2-yl)phenolate (PcTb(SON) (3)) ligands were synthe-sized and identified by elemental, LDI-TOF and X-ray (for 1) analysis. Photoluminescence (PL) and electroluminescence (EL) spec-tra of the compounds contained only emission bands of phthalocyanine and axial ligands but did not contain the bands of f-f transi-tions. It was found that among the complexes 1, 2, 3 the latter had highest photoconductivity (~10–7 S/cm) and photovoltaic properties. An organic photovoltaic device (OPV) of configuration of ITO/3/C60/Alq3/Al revealed open-circuit voltage (VOC) of 0.24 V and short current density (ISC) of 0.3μA/cm2 under illumination by a xenon lamp at 17 mW/cm2.

  4. Radiation chemistry of cyanine dyes: Oxidation and reduction of merocyanine 540. [Accelerated electrons

    Energy Technology Data Exchange (ETDEWEB)

    Harriman, A. (Univ. of Texas, Austin (United States)); Shoute, L.C.T.; Neta, P. (National Inst. of Standards and Technology, Gaithersburg, MD (United States))

    1991-03-21

    Merocyanine 540 (MC) shows promise as a treatment for certain types of leukemia. It is shown that MC readily undergoes one-electron reduction under pulse radiolytic conditions. The {pi}-radical anion, produced by reduction with hydrated electrons and 2-hydroxypropyl radicals, disproportionates rapidly (k = 1.9 {times} 10{sup 9} M{sup {minus}1}s{sup {minus}1}) under anaerobic conditions but reduces O{sub 2} to superoxide ions (k = 1.6 {times} 10{sup 9} M{sup {minus}1}s{sup {minus}1}) in aerated solution. The dye reacts with trichloromethylperoxyl radicals (k = 9 {times} 10{sup 8} M{sup {minus}1}s{sup {minus}1}) to form several products, one of which is believed to be an adduct formed by addition of CCl{sub 3}OO{sup {sm bullet}} to the bridgehead carbon atom of the benzoxazole subunit. This species decays via first-order kinetics (k = 4.0 {times} 10{sup 3} s{sup {minus}1}) under pulse radiolytic conditions to form cleavage products. A second primary product is believed to arise from addition of CCl{sub 3}O{sub 2}{sup {sm bullet}} to the polymethine chain to form an {alpha}-amino carbon-centered radical capable of reducing O{sub 2} to superoxide ions. Preliminary studies indicate that the breakdown products are cytotoxic and could be important intermediates for the known antiviral activity of MC.

  5. Synthesis and Antimicrobial Activities of Some New 1,2,4-Triazole Derivatives

    Directory of Open Access Journals (Sweden)

    Hakan Bektaş

    2010-04-01

    Full Text Available Some novel 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazol-3-one (3, 6, 8, 9 derivatives and or 3-(4-methylphenyl[1,2,4]triazolo[3,4-b][1,3]benzoxazole (5 were synthesized from the reaction of various ester ethoxycarbonylhydrazones (1a-e with several primary amines. The synthesis of 4-amino-5-(4-chlorophenyl-2-[(5-mercapto-1,3,4-oxadiazol-2-ylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (13 was performed starting from 4-Amino-5-(4-chlorophenyl-2,4-dihydro-3H-1,2,4-triazol-3-one (2 by four steps; then 13 was converted to the corresponding Schiff base (14 by using 4-methoxybenzaldehyde. Finally, two Mannich base derivatives of 14 were obtained by using morpholine or methyl piperazine as amine component. All newly synthesized compounds were screened for their antimicrobial activities and some of which were found to possess good or moderate activities against the test microorganisms.

  6. Neural network modelling of antifungal activity of a series of oxazole derivatives based on in silico pharmacokinetic parameters

    Directory of Open Access Journals (Sweden)

    Kovačević Strahinja Z.

    2013-01-01

    Full Text Available In the present paper, the antifungal activity of a series of benzoxazole and oxazolo[ 4,5-b]pyridine derivatives was evaluated against Candida albicans by using quantitative structure-activity relationships chemometric methodology with artificial neural network (ANN regression approach. In vitro antifungal activity of the tested compounds was presented by minimum inhibitory concentration expressed as log(1/cMIC. In silico pharmacokinetic parameters related to absorption, distribution, metabolism and excretion (ADME were calculated for all studied compounds by using PreADMET software. A feedforward back-propagation ANN with gradient descent learning algorithm was applied for modelling of the relationship between ADME descriptors (blood-brain barrier penetration, plasma protein binding, Madin-Darby cell permeability and Caco-2 cell permeability and experimental log(1/cMIC values. A 4-6-1 ANN was developed with the optimum momentum and learning rates of 0.3 and 0.05, respectively. An excellent correlation between experimental antifungal activity and values predicted by the ANN was obtained with a correlation coefficient of 0.9536. [Projekat Ministarstva nauke Republike Srbije, br. 172012 i br. 172014

  7. Ground- and excited-state structural orientation of 2-(2`-hydroxyphenyl)benzazoles in cyclodextrins

    Energy Technology Data Exchange (ETDEWEB)

    Roberts, E.L.; Dey, J.; Warner, I.M. [Louisiana State Univ., Baton Rouge, LA (United States)

    1996-12-12

    The effects of {alpha}-, {beta}-, {gamma}-, and 2,6-di-O-methyl-{beta}-cyclodextrins (CDs) on the ground- and excited-state properties of 2-(2`-hydroxyphenyl)benzoxazole, 2-(2`-hydroxyphenyl)benzothiazole, and 2-(2`-hydroxyphenyl)benzimidazole in aqueous media are investigated. Steady-state fluorescence measurements are used to characterize the interaction of CDs with these azoles. Absorbance measurements indicate increased solubility of the azoles in aqueous solutions of CDs. Measurements of acidity constants (pK{sub a}) and data from induced circular dichroism indicate increased ground- and excited-state acidities of the phenolic protons of the molecules in the presence of CDs and axial orientation of the molecules within the CD cavity, respectively. The data further suggest a planar structure for HBO and a twisted confirmation for both HBT and HBI. The association constants of the inclusion complexes have also been estimated. These studies are further supplemented by comparative spectroscopic studies of 2-(2`-methoxyphenyl)benzothiazole in aqueous solutions of CDs. On the basis of the spectral data acquired, it is believed that the HBA molecules exist as zwitterionic tautomers in the presence of CDs. 35 refs., 6 figs., 2 tabs.

  8. Synthesis,Structure and Photoluminescence of Co-crystal of Bis[2-(benz(oxa/imida)zol-2-yl)phenolato-κ2N,O]zinc(Ⅱ) Being Site Occupancy Disorder with a Heteroatom Ratio of NH to O (0.408/0.592)

    Institute of Scientific and Technical Information of China (English)

    TONG Yi-Ping

    2007-01-01

    The zinc(Ⅱ) complex with Hpbx (Hpbx = 2-(benzoxazol-2-yl)phenol) and Hpbm (Hpbm=2-(benzimidazol-2-yl)phenol),namely[Zn(pbm)2]1.633[Zn(bpx)2]2.367·DMF·2H2O1,has been synthesized and characterized by X-ray crystallography,FTIR and elemental analysis.The coordination structures are statistically disordered and can be regarded as a co-crystal of [Zn(pbm)2]and [Zn(pbx)2] with the ratio of ca.0.408/0.592.Solvate water and DMF molecules are also present in the lattice.Crystal data for 1:monoclinic,space group P21/c,Mr= 2049.02,Z = 2,α = 9,7571(6),b = 25.6415(16),c = 19.8675(10)(A),β = 111.342(2)°,V = 4629.7(5) (A)3,Dc = 1.470 g/cm3,μ =1.100 mm-1,F(000) = 2104,R = 0.0575 and wR = 0.1282 for 5528 observed reflections (I> 2σ(I)).The photoluminescent spectra for this compound have also been studied.

  9. Zn(2+) binding-enabled excited state intramolecular proton transfer: a step toward new near-infrared fluorescent probes for imaging applications.

    Science.gov (United States)

    Xu, Yongqian; Liu, Qin; Dou, Bairui; Wright, Brian; Wang, Jingyun; Pang, Yi

    2012-07-01

    In order to facilitate the in vivo study of zinc-related biology, it is essential to develop a zinc-selective sensor that exhibits both near-infrared (NIR) emission and larger Stokes shift. A fluorescent sensor, Zinhbo-5, has been constructed by using bis(benzoxazole) ligand with 2, 2'-dipicolylamine (DPA) as metal ion receptor. In aqueous solution, Zinhbo-5 exhibits high sensitivity (K(d) = 2.58 nM(2) ) and selectivity for Zn(2+) cation, revealing about 14-fold fluorescence enhancement upon zinc binding to give green emission. Remarkably, Zn(2+) binding to Zinhbo-5 switches on the excited state intramolecular proton transfer (ESIPT), producing the desirable near-infrared region (over 710 nm) with large Stokes shift (ca. 240 nm). The new probe is demonstrated to be useful for in vivo imaging of the intracellular Zn(2+) ion. The Zinhbo-5 is also useful for detecting zinc ion distribution during the development of living zebrafish embryos.

  10. NHC-manganese(i) complexes as carbene transfer agents.

    Science.gov (United States)

    Ruiz, Javier; Berros, Angela; Perandones, Bernabé F; Vivanco, Marilín

    2009-09-21

    Tautomerization of coordinated azoles to their corresponding N-heterocyclic carbenes (NHCs) has been carried out by reaction of complexes fac-[Mn(L)(CO)(3)(dppe)](+) (L = N-phenylimidazole) and fac-[Mn(L)(CO)(3)(bipy)](+) (L = N-methylbenzimidazole, benzoxazole, benzothiazole) with KO(t)Bu and subsequent protonation of the azolyl intermediates with NH(4)PF(6). Several NHC-manganese(i) complexes bearing an N-H residue of general formula fac-[Mn(NHC)(CO)(3)(dppe)](+) and fac-[Mn(NHC)(CO)(3)(bipy)](+) have been tested as carbene transfer agents to the gold fragments [Au(L)](+) (L = PPh(3), CNPh, CNXylyl), allowing isolation or spectroscopic detection of various Mn(i)/Au(i) heterometallic intermediates containing azolyl bridging ligands, which liberate the gold(i) carbene complexes [Au(NHC)(L)](+) by means of acid hydrolysis. By contrast, when using the silver(i) fragment [Ag(PPh(3))](+) as carbene acceptor no transmetallation process occurred but instead inverse tautomerization of the NHC to the corresponding imidazole ligand was observed.

  11. Mechanism of Action and Clinical Application of Tafamidis in Hereditary Transthyretin Amyloidosis.

    Science.gov (United States)

    Coelho, Teresa; Merlini, Giampaolo; Bulawa, Christine E; Fleming, James A; Judge, Daniel P; Kelly, Jeffery W; Maurer, Mathew S; Planté-Bordeneuve, Violaine; Labaudinière, Richard; Mundayat, Rajiv; Riley, Steve; Lombardo, Ilise; Huertas, Pedro

    2016-06-01

    Transthyretin (TTR) transports the retinol-binding protein-vitamin A complex and is a minor transporter of thyroxine in blood. Its tetrameric structure undergoes rate-limiting dissociation and monomer misfolding, enabling TTR to aggregate or to become amyloidogenic. Mutations in the TTR gene generally destabilize the tetramer and/or accelerate tetramer dissociation, promoting amyloidogenesis. TTR-related amyloidoses are rare, fatal, protein-misfolding disorders, characterized by formation of soluble aggregates of variable structure and tissue deposition of amyloid. The TTR amyloidoses present with a spectrum of manifestations, encompassing progressive neuropathy and/or cardiomyopathy. Until recently, the only accepted treatment to halt progression of hereditary TTR amyloidosis was liver transplantation, which replaces the hepatic source of mutant TTR with the less amyloidogenic wild-type TTR. Tafamidis meglumine is a rationally designed, non-NSAID benzoxazole derivative that binds with high affinity and selectivity to TTR and kinetically stabilizes the tetramer, slowing monomer formation, misfolding, and amyloidogenesis. Tafamidis is the first pharmacotherapy approved to slow the progression of peripheral neurologic impairment in TTR familial amyloid polyneuropathy. Here we describe the mechanism of action of tafamidis and review the clinical data, demonstrating that tafamidis treatment slows neurologic deterioration and preserves nutritional status, as well as quality of life in patients with early-stage Val30Met amyloidosis.

  12. Synthesis, structure, photophysical and catalytic properties of CuI-Iodide complexes of di-imine ligands

    Science.gov (United States)

    Mondal, Jahangir; Ghorai, Anupam; Singh, Sunil K.; Saha, Rajat; Patra, Goutam K.

    2016-03-01

    Two new multifunctional CuII based complexes [CuI(L1)] (1) and [Cu2(μ-I)2(L2)] (2) with bidentate N-N donor ligands L1 and imino-pyridyl ligand L2 have been synthesized and characterized by elemental analysis, IR, UV-Vis, NMR and single crystal X-ray crystallography. The bidentate di-imine ligand (L1) forms monomeric CuI complex (1) whereas the bis-bidentate di-imine ligand (L2) favours the formation of dimeric CuI complex (2) in association with two bridging iodides. Structural analysis reveals that in complex 1 each monomeric units are connected by π⋯π and C-H⋯π interactions to form 3D supramolecular structure whereas in complex 2 each molecules are connected by only π⋯π interactions to form 3D supramolecular structure. The photoluminescence properties of the complexes have been studied at room temperature. Theoretical analysis shows that HOMO is focused on the Cu and iodides while LUMO is focused on di-imine ligands and the luminescence behaviour arises due to metal to ligand charge transfer (MLCT) and halide to ligand charge transfer (XLCT). The complexes 1 and 2 are effective catalysts for the synthesis of 2-substituted benzoxazoles.

  13. Simultaneous detection and differentiation of human rhino- and enteroviruses in clinical specimens by real-time PCR with locked nucleic Acid probes.

    Science.gov (United States)

    Osterback, Riikka; Tevaluoto, Tuire; Ylinen, Tiina; Peltola, Ville; Susi, Petri; Hyypiä, Timo; Waris, Matti

    2013-12-01

    Human rhinoviruses (HRVs) and human enteroviruses (HEVs) are significant respiratory pathogens. While HRV infections are restricted to the respiratory tract, HEV infections may spread to secondary target organs. The method of choice for sensitive specific detection of these viruses is reverse transcription (RT)-PCR with primers targeting the conserved 5' noncoding region of the viral RNA. On the other hand, sequence similarities between HRVs and HEVs complicate their differential detection. In this study, we describe the use of locked nucleic acid (LNA) analogues in short double-dye probes which contained only two selectively HRV- or HEV-specific bases. The double-stranded DNA dye BOXTO (4-[6-(benzoxazole-2-yl-(3-methyl-)-2,3-dihydro-(benzo-1,3-thiazole)-2-methylidene)]-1-methyl-quinolinium chloride) was used with the LNA probes in a tricolor real-time PCR assay to allow specific detection of HRVs (probes labeled with 6-carboxyfluorescein [FAM] [green]) and HEVs (Cy5 [red]) with additional melting curve analysis (BOXTO [yellow]). The functionality of the probes was validated in PCR and RT-PCR assays using plasmids containing viral cDNA, quantified viral RNA transcripts, cultivated rhino- and enterovirus prototypes, and clinical specimens. Of 100 HRV and 63 HEV prototypes, the probes correctly identified all HEVs except one that produced only a BOXTO signal. Among 118 clinical specimens with sequencing results, concordant results were obtained for 116 specimens. Two specimens were reactive with both probes, but sequencing yielded only a single virus. Real-time PCR with LNA probes allowed sensitive group-specific identification of HRVs and HEVs and would enable relative copy number determination. The assay is suitable for rapid and accurate differential detection of HRVs and HEVs in a diagnostic laboratory setting.

  14. Synthesis and light-emitting properties of organic electroluminescent compounds and their metal complexes

    Institute of Scientific and Technical Information of China (English)

    CUI Jianzhong; Kim Sung-Hoon

    2004-01-01

    Several organic electroluminescent (EL) compounds, 2,2′-(1,4-phenylenedivinylene)bis-3,3-dimethyl-in- dolenine (1), 2,2′-(1,4-phenylenedivinylene)bis-benzoxazole (2), 2,2′-(1,4-phenylenedivinylene)bis-benzothiazole (3), 4,4′- (1,4-phenylenedivinylene)bis-quinoline (4), 2,2′-(1,4-phenyle- nedivinylene)bis-quinoline (5), 2,2′-(1,4-phenylenedivinyle- ne)bis-1,3,3-trimethyl-indolenine dichlo ride (6), 2,2′-(1,4- phenylene-divinylene)bis-1-hydro-3,3-dimethyl-indolenine dichloride (7), 2,2′-(1,4-phenylenedivinylene)bis-8-acetoxy- quinoline (8), 2,2′-(1,4-phenylenedivinylene)bis-8-hydroxyq- uinoline (9) and metal complexes of 9, Al(PHQ) (10) and Zn(PHQ) (11), have been synthesized and characterized. The crystal structure of 6 was determined. Light emitting properties of the prepared compounds have been investigated. 1 produces an orange-yellow emission (λmax = 575 nm). The cation, 6, gives a red emission (λmax = 607 nm), which is shifted 32 nm to the red compared to 1. 8 produces a yellow emission (λmax = 567 nm). The metal complex 10 gives a red emission (λmax = 610 nm), which is a red shift of 43 nm compared to 8. The change in structure in the prepared compound caused a change in the electron distribution in the compounds, which induces a large wavelength shift of the emitted-light. Thermal analysis showed that the decomposition temperatures of the metal complexes (10, 11) were higher than those for the smaller organic molecular compounds (1-9). Therefore, metal complexes (10, 11) can be used as EL materials over a larger temperature range.

  15. Steady-state spectroscopy of new biological probes

    Science.gov (United States)

    Abou-Zied, Osama K.

    2007-02-01

    The steady state absorption and fluorescence spectroscopy of 2-(2'-hydroxyphenyl)benzoxazole (HBO) and (2,2'-bipyridine)-3,3'-diol (BP(OH) II) were studied here free in solution and in human serum albumin (HSA) in order to test their applicability as new biological probes. HBO and BP(OH) II are known to undergo intramolecular proton transfers in the excited state. Their absorption and fluorescence spectra are sensitive to environmental change from hydrophilic to hydrophobic, thus allowing the opportunity to use them as environment-sensitive probes. The effect of water on the steady state spectra of the two molecules also shows unique features which may position them as water sensors in biological systems. For HBO in buffer, fluorescence is only due to the syn-keto tautomer, whereas in HSA the fluorescence is due to four species in equilibrium in the excited state (the syn-keto tautomer, the anti-enol tautomer, the solvated syn-enol tautomer, and the anion species of HBO). Analysis of the fluorescence spectra of HBO in HSA indicates that HBO is exposed to less water in the HBO:HSA complex. For the BP(OH) II molecule, unique absorption due to water was observed in the spectral region of 400-450 nm. This absorption decreases in the presence of HSA due to less accessibility to water as a result of binding to HSA. Fluorescence of BP(OH) II is due solely to the di-keto tautomer after double proton transfer in the excited state. The fluorescence peak of BP(OH) II shows a red-shift upon HSA recognition which is attributed to the hydrophobic environment inside the binding site of HSA. We discuss also the effect of probe-inclusion inside well-defined hydrophobic cavities of cyclodextrins.

  16. Efficient and versatile catalysis of N-alkylation of heterocyclic amines with alcohols and one-pot synthesis of 2-aryl substituted benzazoles with newly designed ruthenium(II) complexes of PNS thiosemicarbazones.

    Science.gov (United States)

    Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Ramkumar, Venkatachalam

    2014-06-07

    Ruthenium(II) carbonyl complexes with phosphine-functionalized PNS type thiosemicarbazone ligands [RuCl(CO)(EPh3)(L)] (1-6) (E = P or As, L = 2-(2-(diphenylphosphino)benzylidene) thiosemicarbazone (PNS-H), 2-(2-(diphenylphosphino)benzylidene)-N-methylthiosemicarbazone (PNS-Me), 2-(2-(diphenylphosphino)benzylidene)-N-phenylthiosemicarbazone (PNS-Ph)) have been synthesized and characterized by elemental analysis and spectroscopy (IR, UV-Vis, (1)H, (13)C, (31)P-NMR) as well as ESI mass spectrometry. The molecular structures of complexes 1, 2 and 6 were identified by means of single-crystal X-ray diffraction analysis. The analysis revealed that all the complexes possess a distorted octahedral geometry with the ligand coordinating in a uni-negative tridentate PNS fashion. All the ruthenium complexes (1-6) were tested as catalyst for N-alkylation of heteroaromatic amines with alcohols. Notably, complex 2 was found to be a very efficient and versatile catalyst towards N-alkylation of a wide range of heterocyclic amines with alcohols. Complex 2 can also catalyze the direct amination of 2-nitropyridine with benzyl alcohol to the corresponding secondary amine. Furthermore, a preliminary examination of performance for N,N-dialkylation of diamine showed promising results, giving good conversion and high selectivity. In addition, N-alkylation of ortho-substituted anilines (-NH2, -OH and -SH) led to the one-pot synthesis of 2-aryl substituted benzimidazoles, benzoxazoles and benzothiazoles, also revealing the catalytic activity of complex 2.

  17. Characterization of a novel acetamidobenzoxazolone-based PET ligand for translocator protein (18 kDa) imaging of neuroinflammation in the brain.

    Science.gov (United States)

    Tiwari, Anjani K; Yui, Joji; Fujinaga, Masayuki; Kumata, Katsushi; Shimoda, Yoko; Yamasaki, Tomoteru; Xie, Lin; Hatori, Akiko; Maeda, Jun; Nengaki, Nobuki; Zhang, Ming-Rong

    2014-05-01

    We developed the novel positron emission tomography (PET) ligand 2-[5-(4-[(11)C]methoxyphenyl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-methyl-N-phenylacetamide ([(11)C]MBMP) for translocator protein (18 kDa, TSPO) imaging and evaluated its efficacy in ischemic rat brains. [(11)C]MBMP was synthesized by reacting desmethyl precursor (1) with [(11)C]CH3 I in radiochemical purity of ≥ 98% and specific activity of 85 ± 30 GBq/μmol (n = 18) at the end of synthesis. Biodistribution study on mice showed high accumulation of radioactivity in the TSPO-rich organs, e.g., the lungs, heart, kidneys, and adrenal glands. The metabolite analysis in mice brain homogenate showed 80.1 ± 2.7% intact [(11)C]MBMP at 60 min after injection. To determine the specific binding of [(11)C]MBMP with TSPO in the brain, in vitro autoradiography and PET studies were performed in an ischemic rat model. In vitro autoradiography indicated significantly increased binding on the ipsilateral side compared with that on the contralateral side of ischemic rat brains. This result was supported firmly by the contrast of radioactivity between the ipsilateral and contralateral sides in PET images. Displacement experiments with unlabelled MBMP or PK11195 minimized the difference in uptake between the two sides. In summary, [(11)C]MBMP is a potential PET imaging agent for TSPO and, consequently, for the up-regulation of microglia during neuroinflammation.

  18. Transferable potentials for phase equilibria. 10. Explicit-hydrogen description of substituted benzenes and polycyclic aromatic compounds.

    Science.gov (United States)

    Rai, Neeraj; Siepmann, J Ilja

    2013-01-10

    The explicit-hydrogen version of the transferable potentials for phase equilibria (TraPPE-EH) force field is extended to various substituted benzenes through the parametrization of the exocyclic groups -F, -Cl, -Br, -C≡N, and -OH and to polycyclic aromatic hydrocarbons through the parametrization of the aromatic linker carbon atom for multiple rings. The linker carbon together with the TraPPE-EH parameters for aromatic heterocycles constitutes a force field for fused-ring heterocycles. Configurational-bias Monte Carlo simulations in the Gibbs ensemble were carried out to compute vapor-liquid coexistence curves for fluorobenzene; chlorobenzene; bromobenzene; di-, tri-, and hexachlorobenzene isomers; 2-chlorofuran; 2-chlorothiophene; benzonitrile; phenol; dihydroxybenzene isomers; 1,4-benzoquinone; naphthalene; naphthalene-2-carbonitrile; naphthalen-2-ol; quinoline; benzo[b]thiophene; benzo[c]thiophene; benzoxazole; benzisoxazole; benzimidazole; benzothiazole; indole; isoindole; indazole; purine; anthracene; and phenanthrene. The agreement with the limited experimental data is very satisfactory, with saturated liquid densities and vapor pressures reproduced to within 1.5% and 15%, respectively. The mean unsigned percentage errors in the normal boiling points, critical temperatures, and critical densities are 0.9%, 1.2%, and 1.4%, respectively. Additional simulations were carried out for binary systems of benzene/benzonitrile, benzene/phenol, and naphthalene/methanol to illustrate the transferability of the developed potentials to binary systems containing compounds of different polarity and hydrogen-bonding ability. A detailed analysis of the liquid-phase structures is provided for selected neat systems and binary mixtures.

  19. Synthesis and Crystal Structure of Rctt-1-(2-benzoxazolyl)-2-(4-chlorophenyl)-4-phenyl-3-(4-pyridinyl) cyclobutane

    Institute of Scientific and Technical Information of China (English)

    庄俊鹏; 张文勤

    2003-01-01

    The title compound (C28H21ClN2O, Mr = 436.92) was synthesized by the cross- photodimerization of (E)-2-(2-phenylethenyl)benzoxazole and (E)-4-[2-(4-chlorophenyl)ethenyl]- pyridine in sulfuric acid solution. Its molecular structure has been unequivocally determined by X-ray crystallography. The title compound belongs to triclinic system, space group Pī with cell parameters: a = 9.648(3), b = 10.458(4), c = 12.106(4) A。, r = 89.089(7), a = 75.644(6), B = 68.441(7)o, V = 1096.7(7) A。3, Z = 2, Dc = 1.323 g/cm3, F(000) = 456 and ((MoKa) = 0.198 mm-1. The final R and wR are 0.0627 and 0.1285, respectively for 1737 observed reflections with I > 2((I). S = 0.921 and (Δ/max = 0.001. The cyclobutane ring has a puckered conformation with four different aryl groups substituted on each carbon atom. The dihedral angles of the cyclobutane ring are 20.2 and 20.6o. The bond distances of the cyclobutane ring are 1.541, 1.555, 1.560 and 1.563 A。, respectively, which are slightly longer than that of the normal C-C single bond. The title compound is the only cross-dimer and its two heteroaryl groups are situated at the trans-1,3 position of the cyclobutane ring, revealing that the cross-photodimerization proceeds in a head-to-tail pattern with high stereo-selectivity.

  20. Infrared and Raman spectra of bicyclic molecules using scaled noncorrelated and correlated {ital ab initio} force fields

    Energy Technology Data Exchange (ETDEWEB)

    Collier, W.B. [Department of Chemistry, Oral Roberts University, Tulsa, Oklahoma 74171 (United States); Magdo, I. [Gedeon Richter Ltd., Molecular Design Unit, P.O. Box 27, H-1475, Budapest (Hungary); Klots, T.D. [Bartlesville Thermodynamic Group, BDM Petroleum Technologies, P.O. Box 2543, Bartlesville, Oklahoma 74005 (United States)

    1999-03-01

    This paper reports the application of a scaled {ital ab initio} calculated harmonic force field to predict the frequencies, infrared intensities, Raman intensities, and depolarization ratios of benzofuran, benzothiophene, indole, benzothiazole, and benzoxazole. The theoretical calculations were made using the Hartree{endash}Fock HF/3-21G{sup {asterisk}} and HF/6-31G{sup {asterisk}} basis sets and density-functional theory (DFT)B3-LYP/6-31G{sup {asterisk}} levels. The equilibrium calculated force constants are scaled according to the method of Pulay and compared with the experimentally determined frequencies, intensities, and depolarization ratios to assess the accuracy and fit of the theoretical calculation. Methods for quantitative comparison of intensities were developed. The double numerical differentiation algorithm of Komornicki and McIver was analyzed and used to calculate the Raman intensities for the (DFT)B3-LYP/6-31G{sup {asterisk}} model. The (DFT)B3-LYP/6-31G{sup {asterisk}} model is approaching the harmonic limit in the planar and nonplanar refinement of these bicyclics with wave number fits of 5 and 4 cm{sup {minus}1}, respectively. It reduces the need for scale factors and increases their transfer accuracy, largely because the scale factors values cluster near unity. The Komornicki and McIver algorithm is still a viable method for calculating Raman intensity information for methods that do not have analytic routines programmed. The main shortcoming to this method may lie in the tighter self-consistent field (SCF) convergence criterion possibly needed to calculate Raman intensities for the totally symmetric modes of large molecules. The (DFT)B3-LYP/6-31G{sup {asterisk}} model was superior for calculating the planar intensities, but equal to the HF methods for predicting the nonplanar intensities. {copyright} {ital 1999 American Institute of Physics.}

  1. Synthesis and Crystal Structure of Rctt—1—(2—benzoxaolyl)—2—(4—chlorophenyl)—4—phenyl—3—(4—pyridinyl)cyclobutane

    Institute of Scientific and Technical Information of China (English)

    ZHUANGJun-Peng; ZHANGWen-Qin

    2003-01-01

    The title compound (C28H21C1N2O,Mr=436.92) was synthesized by the cross-photodimerization of (E)-2-(2-phenylethenyl) benzoxazole and (E)-4-[2-(4-cholrophenyl)ethenyl]-pyridine in sulfuric acid solution.Its molecular structure has been unequivocally detemined by X-ray Crystallography,The title compound belongs to triclinic system,space group P-↑1 with cell parameters:a=9.648(3),b=0.458(4),c=12.1064(4)°↑A,α=89.089(7),β=75.644(6),γ=68.441(7)°,V=1096.7(7)°↑A3,Z=2,Dc=1.323 g/cm3,F(000)=456 and μ(Mokα)=0.198mm-1,The final R and wR are 0.0627 and 0.1285,respectively for 1737 observed refections with I>2σ(I),S=0.921 and (△/σ)max=0.001,The cyclobutane ring has a puckered conformation with four different aryl groups substituted on each carbon atom.The dihedral angles of the cyclobutane ring are 20.2 and 20.6°.The bond distances of the cyclobutane ring are 1.541,1.555,1.560 and 1.563°↑A,respectively,which are slightly longer than that of the normal C-C single bond.The title compound is the only cross-dimer and its two heteroaryl groups are situated at the trans-1,3 position of the cyclobutane ring,revealing that the cross-photodimerization proceeds in a head-to-tail pattern with high stereo-selectivity.

  2. C-H and N-H bond dissociation energies of small aromatic hydrocarbons

    Energy Technology Data Exchange (ETDEWEB)

    Barckholtz, C.; Barckholtz, T.A.; Hadad, C.M.

    1999-01-27

    A survey of computational methods was undertaken to calculate the homolytic bond dissociation energies (BDEs) of the C-H and N-H bonds in monocyclic aromatic molecules that are representative of the functionalities present in coal. These include six-membered rings (benzene, pyridine, pyridazine, pyrimidine, pyrazine) and five-membered rings (furan, thiophene, pyrrole, oxazole). By comparison of the calculated C-H BDEs with the available experimental values for these aromatic molecules, the B3LYP/6-31G(d) level of theory was selected to calculate the BDEs of polycyclic aromatic hydrocarbons (PAHs), including carbonaceous PAHs (naphthalene, anthracene, pyrene, coronene) and heteroatomic PAHs (benzofuran, benzothiophene, indole, benzoxazole, quinoline, isoquinoline, dibenzofuran, carbazole). The cleavage of a C-H or a N-H bond generates a {sigma} radical that is, in general, localized at the site from which the hydrogen atom was removed. However, delocalization of the unpaired electron results in {approximately} 7 kcal {center{underscore}dot} mol{sup {minus}1} stabilization of the radical with respect to the formation of phenyl when the C-H bond is adjacent to a nitrogen atom in the azabenzenes. Radicals from five-membered rings are {approximately} 6 kcal {center{underscore}dot} mol{sup {minus}1} less stable than those formed from six-membered rings due to both localization of the spin density and geometric factors. The location of the heteroatoms in the aromatic ring affects the C-H bond strengths more significantly than does the size of the aromatic network. Therefore, in general, the monocyclic aromatic molecules can be used to predict the C-H BDE of the large PAHs within 1 kcal {center{underscore}dot} mol{sup {minus}1}.

  3. 2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

    Science.gov (United States)

    Sayapin, Yury A; Tupaeva, Inna O; Kolodina, Alexandra A; Gusakov, Eugeny A; Komissarov, Vitaly N; Makarova, Nadezhda I; Metelitsa, Anatoly V; Tkachev, Valery V; Aldoshin, Sergey M; Minkin, Vladimir I

    2015-01-01

    Summary A series of derivatives of 2-hetaryl-1,3-tropolone (β-tropolone) was prepared by the acid-catalyzed reaction of 2-methylbenzoxazoles, 2-methylbenzothiazoles and 2,3,3-trimethylindoline with 3,4,5,6-tetrachloro-1,2-benzoquinone. The molecular structures of the three representative compounds were determined by X-ray crystallography. In crystal and (as shown by the DFT PBE0/6-311+G** calculations) in solution, 2-hetaryl-4,5,6,7-tetrachloro- and 2-hetaryl-5,6,7-trichloro-1,3-tropolones exist in the NH-tautomeric form with a strong resonance-assisted intramolecular N–H···O hydrogen bond. The mechanism of the formation of 1,3-tropolones in the reaction of methylene-active five-membered heterocycles with o-chloranil in acetic acid solution has been studied using density functional theory (DFT) methods. The reaction of 2-(2-benzoxa(thia)zolyl)-5,6,7-trichloro(4,5,6,7-tetrachloro)-1,3-tropolones with alcohols leads to the contraction of the seven-membered tropone ring with the formation of 2-(2-benzoxa(thia)zolyl)-6-alkoxycarbonylphenols. The molecular structure of 2-(2-ethoxycarbonyl-6-hydroxy-3,4,5-trichlorophenyl)benzoxazole has been determined by X-ray diffraction. 2-(2-Benzoxa(thia)zolyl)-6-alkoxycarbonylphenols display intense green fluorescence with anomalous Stokes shifts caused by the excited state intramolecular proton transfer (ESIPT) effects. PMID:26664640

  4. Synthesis of a New Fluorescent Brightener and Their Use in Plastic%一种新荧光增白剂的合成及其在塑料中的应用

    Institute of Scientific and Technical Information of China (English)

    胡义娇; 徐会志; 金可刚; 陈昱; 单雅丽; 程德文

    2011-01-01

    A new kind of fluorescent brightener,4,4′-bis(5-tert-butyl-benzoxazol-2-yl)stilbene,has been synthesized from 4-cyanobenzyl chloride and 4-butyl-2-aminophenol by two steps.It was found that the whitening effects of the product on PE(polyethylene),PP(polypropylene),PVC(polyvinylchlorid) and PET(polyethylene terephthalate) were good.The proper concentration for PE was 0.005% to 0.02% by weight.Comparing with other bisbenzoxazole stilbene fluorescent brightener such as OB-1 and OB-2,it presented better whitening effect when whitening PP.%本文介绍了4,4'-双(对叔丁基苯并噁唑-2-基)二苯乙烯的合成方法。以对氰基氯苄和对叔丁基邻氨基苯酚为原料分两步合成而制得。将制得的荧光增白剂用于PE(聚乙烯)、PP(聚丙烯)、PVC(聚氯乙烯)、PET(聚对苯二甲酸乙二醇酯),均有较好的增白效果。通过实验得到在PE上的合适添加量为0.005%~0.02%。与目前市场上常用的其他双苯并噁唑二苯乙烯类荧光增白剂如荧光增白剂OB-1、OB-2相比,在PP上的增白效果更优异。

  5. Antifungal antibiotic CA1189 produced by a Mangrove endophyte Streptomyces sp.A1626%红树林内生链霉菌A1626产生的抗真菌抗生素CA1189

    Institute of Scientific and Technical Information of China (English)

    褚以文; 李进军; 王辂; 余蓉

    2011-01-01

    Objective To purify and to identify an antifungal compound of an endophytic isolate Streptomyces sp. A1626, which was isolated from stems of Kandelia candel(Linn.) Druce, and to determine its antifungal activity. Methods Compound CA 1189 was separated and purified by solvent extraction, silica gel, RP-18 column chromatography. Its structure was elucidated on the basis of extensive spectroscopic analysis including UV, IR, MS,1D and 2D NMR experiments. Its in vitro antifungal activity was determined with micro-broth dilution assay. Results and Conclusion The potent antifungal compound CA 1189 is identical with benzoxazole derivative AJI9561.%目的 研究秋茄内生链霉菌菌株A1626产生的活性代谢产物.方法 发酵液经有机溶剂萃取、正相硅胶柱层析、C18柱制备色谱分离获得单体,通过紫外光谱、红外光谱、质谱、一维和二维核磁共振谱的测定解析,确证单体化合物的结构,采用微量液体稀释法对单体化合物的抗真菌活性进行测定.结果 与结论活性化合物CA1189属于苯并噁唑类,与文献报道的AYI9561结构一致,其抗真菌活性为首次报道.

  6. Mitochondrial aldehyde dehydrogenase obliterates insulin resistance-induced cardiac dysfunction through deacetylation of PGC-1α

    Science.gov (United States)

    Hu, Nan; Ren, Jun; Zhang, Yingmei

    2016-01-01

    Insulin resistance contributes to the high prevalence of type 2 diabetes mellitus, leading to cardiac anomalies. Emerging evidence depicts a pivotal role for mitochondrial injury in oxidative metabolism and insulin resistance. Mitochondrial aldehyde dehydrogenase (ALDH2) is one of metabolic enzymes detoxifying aldehydes although its role in insulin resistance remains elusive. This study was designed to evaluate the impact of ALDH2 overexpression on insulin resistance-induced myocardial damage and mechanisms involved with a focus on autophagy. Wild-type (WT) and transgenic mice overexpressing ALDH2 were fed sucrose or starch diet for 8 weeks and cardiac function and intracellular Ca2+ handling were assessed using echocardiographic and IonOptix systems. Western blot analysis was used to evaluate Akt, heme oxygenase-1 (HO-1), PGC-1α and Sirt-3. Our data revealed that sucrose intake provoked insulin resistance and compromised fractional shortening, cardiomyocyte function and intracellular Ca2+ handling (p 0.05), mitochondrial injury (elevated ROS generation, suppressed NAD+ and aconitase activity, p < 0.05 for all), the effect of which was ablated by ALDH2. In vitro incubation of the ALDH2 activator Alda-1, the Sirt3 activator oroxylin A and the histone acetyltransferase inhibitor CPTH2 rescued insulin resistance-induced changes in aconitase activity and cardiomyocyte function (p < 0.05). Inhibiting Sirt3 deacetylase using 5-amino-2-(4-aminophenyl) benzoxazole negated Alda-1-induced cardioprotective effects. Taken together, our data suggest that ALDH2 serves as an indispensable cardioprotective factor against insulin resistance-induced cardiomyopathy with a mechanism possibly associated with facilitation of the Sirt3-dependent PGC-1α deacetylation. PMID:27634872

  7. Estrogen receptor beta-selective agonists stimulate calcium oscillations in human and mouse embryonic stem cell-derived neurons.

    Directory of Open Access Journals (Sweden)

    Lili Zhang

    Full Text Available Estrogens are used extensively to treat hot flashes in menopausal women. Some of the beneficial effects of estrogens in hormone therapy on the brain might be due to nongenomic effects in neurons such as the rapid stimulation of calcium oscillations. Most studies have examined the nongenomic effects of estrogen receptors (ER in primary neurons or brain slices from the rodent brain. However, these cells can not be maintained continuously in culture because neurons are post-mitotic. Neurons derived from embryonic stem cells could be a potential continuous, cell-based model to study nongenomic actions of estrogens in neurons if they are responsive to estrogens after differentiation. In this study ER-subtype specific estrogens were used to examine the role of ERalpha and ERbeta on calcium oscillations in neurons derived from human (hES and mouse embryonic stem cells. Unlike the undifferentiated hES cells the differentiated cells expressed neuronal markers, ERbeta, but not ERalpha. The non-selective ER agonist 17beta-estradiol (E(2 rapidly increased [Ca2+]i oscillations and synchronizations within a few minutes. No change in calcium oscillations was observed with the selective ERalpha agonist 4,4',4''-(4-Propyl-[1H]-pyrazole-1,3,5-triyltrisphenol (PPT. In contrast, the selective ERbeta agonists, 2,3-bis(4-Hydroxyphenyl-propionitrile (DPN, MF101, and 2-(3-fluoro-4-hydroxyphenyl-7-vinyl-1,3 benzoxazol-5-ol (ERB-041; WAY-202041 stimulated calcium oscillations similar to E(2. The ERbeta agonists also increased calcium oscillations and phosphorylated PKC, AKT and ERK1/2 in neurons derived from mouse ES cells, which was inhibited by nifedipine demonstrating that ERbeta activates L-type voltage gated calcium channels to regulate neuronal activity. Our results demonstrate that ERbeta signaling regulates nongenomic pathways in neurons derived from ES cells, and suggest that these cells might be useful to study the nongenomic mechanisms of estrogenic compounds.

  8. Synthesis and docking studies of novel antitumor benzimidazoles.

    Science.gov (United States)

    Omar, Mohamed A; Shaker, Yasser M; Galal, Shadia A; Ali, Mamdouh M; Kerwin, Sean M; Li, Jing; Tokuda, Harukuni; Ramadan, Raghda A; El Diwani, Hoda I

    2012-12-15

    In this work, the benzimidazole-pyrrole conjugates 6a-h and benzimidazole-tetracycles conjugates 12-14 were prepared. The cytotoxicity of the compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 was tested against lung cancer cell line A549. Compound 6b exhibited higher activity than the bis-benzoxazole natural product (UK-1), the standard. The tested 4g,h, 6a-h, 10 and 12-14 exhibited remarkable cytotoxicity activity against breast cancer cell line MCF-7 with higher activity than tamoxifen. Furthermore, compound 4h was found to be also more potent than doxurubicin. The antitumor promotion activity of synthesized compounds 4g,h, 6a-h, 10 and 12-14 has been estimated by studying their possible inhibitory effects on EBV-EA activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Among the studied compounds, the inhibitory activities of compounds 8, 13 and 14 demonstrated strong inhibitory effects on the Epstein-Barr virus early antigen (EBV-EA) activation without showing any cytotoxicity on the Raji cells and their effects being stronger than that of a representative control, oleanolic acid. Moreover, the molecular docking of the new compounds into plasminogen activator (uPA) receptor has been in correlation with the antitumor activity. All synthesized compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 were docked into same groove of the binding site of the native co-crystalized (4-iodobenzo[b]thiophene-2-carboxamidine) ligand (PDB code:1c5x) for activity explaination. Compounds 4h, 6b and 13, giving the best docking results, were further studied to estimate their effect on the level of uPA using AssayMax human urokinase (uPA) ELISA kit. In case of A549 cell line, compound 6 exhibited similar activity to MMC, and for MCF-7 cell line, compound 4h exhibited similar activity to doxorubicin, in inhibiting the expression of uPA.

  9. Redox induced switching dynamics of a three colour electrochromic metallopolymer film

    Energy Technology Data Exchange (ETDEWEB)

    Zeng, Qiang; McNally, Andrea; Keyes, Tia E.; Forster, Robert J. [National Centre for Sensor Research, Biomedical Diagnostics Institute, School of Chemical Sciences, Dublin City University, Dublin 9 (Ireland)

    2008-10-15

    Thin films of a novel Ru-phenolate based metallopolymer, [Ru(terpy)(box)PVP{sub 20}]PF{sub 6}, in which one in every twenty of the 4-vinyl pyridine monomer units is labelled with the ruthenium complex have been formed on glassy carbon electrodes, terpy is 2,2':6',2''-terpyridine, box is 2-(2-hydroxyphenyl)benzoxazole, and PVP is poly(4-vinylpyridine). Cyclic voltammetry and Raman spectroscopy reveal that the Ru{sup 2+/3+} couple is electrochemically reversible but that the phenolate ligand based oxidation is irreversible. These redox processes are associated with reversible colour changes from wine red (reduced) to red orange (mixed composition) then to light green (oxidized) in the visible region and an irreversible change in the near-IR region, respectively. Scanning electron microscopy reveals that repeated switching in LiClO{sub 4} aqueous solution does not induce any significant structural change within the deposit films. Cyclic voltammetry has been used to determine the electrochromic switching rate under semi-infinite linear diffusion conditions. In aqueous LiClO{sub 4}, the homogeneous charge transport diffusion coefficient, D{sub CT}, decreases from 3.6 {+-} 0.3 x 10{sup -13} to 2.7 {+-} 0.2 x 10{sup -13} cm{sup 2} s{sup -1} as the LiClO{sub 4} concentration increases from 0.1 to 1.0 M. This weak dependence of D{sub CT} on electrolyte concentration suggests that counterion availability is not rate-determining and that the overall rate of charge transport through the metallopolymer film is limited by the rate of segmental polymer chain motion necessary to bring adjacent centres sufficiently close to allow electron transfer to occur. Also the impact of changing the identity of the charge compensating anion of the redox electrochromic switching rate has been investigated. Finally, the electronic conductivity has been determined using interdigitated array electrodes (IDAs). (author)

  10. Redox induced switching dynamics of a three colour electrochromic metallopolymer film

    Energy Technology Data Exchange (ETDEWEB)

    Zeng Qiang; McNally, Andrea; Keyes, Tia E. [National Centre for Sensor Research, Biomedical Diagnostics Institute, School of Chemical Sciences, Dublin City University, Dublin 9 (Ireland); Forster, Robert J. [National Centre for Sensor Research, Biomedical Diagnostics Institute, School of Chemical Sciences, Dublin City University, Dublin 9 (Ireland)], E-mail: robert.forster@dcu.ie

    2008-10-15

    Thin films of a novel Ru-phenolate based metallopolymer, [Ru(terpy)(box)PVP{sub 20}]PF{sub 6}, in which one in every twenty of the 4-vinyl pyridine monomer units is labelled with the ruthenium complex have been formed on glassy carbon electrodes, terpy is 2,2':6',2''-terpyridine, box is 2-(2-hydroxyphenyl)benzoxazole, and PVP is poly(4-vinylpyridine). Cyclic voltammetry and Raman spectroscopy reveal that the Ru{sup 2+/3+} couple is electrochemically reversible but that the phenolate ligand based oxidation is irreversible. These redox processes are associated with reversible colour changes from wine red (reduced) to red orange (mixed composition) then to light green (oxidized) in the visible region and an irreversible change in the near-IR region, respectively. Scanning electron microscopy reveals that repeated switching in LiClO{sub 4} aqueous solution does not induce any significant structural change within the deposit films. Cyclic voltammetry has been used to determine the electrochromic switching rate under semi-infinite linear diffusion conditions. In aqueous LiClO{sub 4}, the homogeneous charge transport diffusion coefficient, D{sub CT}, decreases from 3.6 {+-} 0.3 x 10{sup -13} to 2.7 {+-} 0.2 x 10{sup -13} cm{sup 2} s{sup -1} as the LiClO{sub 4} concentration increases from 0.1 to 1.0 M. This weak dependence of D{sub CT} on electrolyte concentration suggests that counterion availability is not rate-determining and that the overall rate of charge transport through the metallopolymer film is limited by the rate of segmental polymer chain motion necessary to bring adjacent centres sufficiently close to allow electron transfer to occur. Also the impact of changing the identity of the charge compensating anion of the redox electrochromic switching rate has been investigated. Finally, the electronic conductivity has been determined using interdigitated array electrodes (IDAs)

  11. Molecular Design and Electronic Structure Investigation of Novel Nitrogen Heteroatom 2-β-Naphthylbenzoxazoles%新型氮杂2-β-萘基苯并(口恶)唑分子设计及其电子结构

    Institute of Scientific and Technical Information of China (English)

    孙京国; 冯玉玲; 姚国伟

    2002-01-01

    For the aim of finding new available functional materials, a series of nitrogen heteroatom 2-β-naphthylbenzoxazole molecules were designed based on the experiment and theoretical studies of 2-β-naphthylbenzoxazole molecule. Geometry optimization of the 2-β-naphthylbenzoxazole was carried out by using Hyperchem Molecular Mechanics plus MM+. The planar molecular structure was obtained. The quantum chemistry calculating method PPP-SCF-CI, which is specially available to treat electron spectrum, was applied to investigate each novel designed molecules. Their electronic structures were analyzed in detail, it shows that total π-electron energy decreased linearly with the number of replaced nitrogen. Single nitrogen atom located in benzoxazole ring or naphthalene ring results in contrary changes of level difference of FMO; multiple nitrogen atoms located in different molecular positions will lead to polarization of extremum in the level difference of FMO; and 5 nitrogen heteroatoms reach the culmination. Considering other electronic structure information, some favorable designed molecules were identified.%为寻找可能的具有特殊性能的新型苯并(口恶)唑类分子材料,在取得对2-β-萘基苯并唑分子进行实验研究和理论分析结果一致的基础上,设计了一系列新型氮杂目标分子,用Hyperchem程序中的分子力学MM+方法对分子进行了优化,得到平面共轭几何构型. 用PPP-SCF-CI方法,对设计分子的电子结构进行了较为详细的探究. 结果表明,分子体系π电子总能量随氮杂原子引入数量呈线性下降. 在苯并唑环与萘环引入单氮杂原子后,FMO能级差显示相反效应. 多氮杂原子引入不同位置后,FMO能级差极值点两极分化,至5氮杂化达到极限. 结合其它电子结构信息,最终筛选出一些特性材料分子.

  12. Estrogen receptor beta growth-inhibitory effects are repressed through activation of MAPK and PI3K signalling in mammary epithelial and breast cancer cells.

    Science.gov (United States)

    Cotrim, C Z; Fabris, V; Doria, M L; Lindberg, K; Gustafsson, J-Å; Amado, F; Lanari, C; Helguero, L A

    2013-05-09

    Two thirds of breast cancers express estrogen receptors (ER). ER alpha (ERα) mediates breast cancer cell proliferation, and expression of ERα is the standard choice to indicate adjuvant endocrine therapy. ERbeta (ERβ) inhibits growth in vitro; its effects in vivo have been incompletely investigated and its role in breast cancer and potential as alternative target in endocrine therapy needs further study. In this work, mammary epithelial (EpH4 and HC11) and breast cancer (MC4-L2) cells with endogenous ERα and ERβ expression and T47-D human breast cancer cells with recombinant ERβ (T47-DERβ) were used to explore effects exerted in vitro and in vivo by the ERβ agonists 2,3-bis (4-hydroxy-phenyl)-propionitrile (DPN) and 7-bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol (WAY). In vivo, ERβ agonists induced mammary gland hyperplasia and MC4-L2 tumour growth to a similar extent as the ERα agonist 4,4',4''-(4-propyl-(1H)-pyrazole-1,3,5-triyl) trisphenol (PPT) or 17β-estradiol (E2) and correlated with higher number of mitotic and lower number of apoptotic features. In vitro, in MC4-L2, EpH4 or HC11 cells incubated under basal conditions, ERβ agonists induced apoptosis measured as upregulation of p53 and apoptosis-inducible factor protein levels and increased caspase 3 activity, whereas PPT and E2 stimulated proliferation. However, when extracellular signal-regulated kinase 1 and 2 (ERK ½) were activated by co-incubation with basement membrane extract or epidermal growth factor, induction of apoptosis by ERβ agonists was repressed and DPN induced proliferation in a similar way as E2 or PPT. In a context of active ERK ½, phosphatidylinositol-4,5-bisphosphate 3-kinase (PI3K)/RAC-alpha serine/threonine-protein kinase (AKT) signalling was necessary to allow proliferation stimulated by ER agonists. Inhibition of MEK ½ with UO126 completely restored ERβ growth-inhibitory effects, whereas inhibition of PI3K by LY294002 inhibited ERβ-induced proliferation. These

  13. Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease.

    Science.gov (United States)

    Rodríguez-Rodríguez, Cristina; Sánchez de Groot, Natalia; Rimola, Albert; Alvarez-Larena, Angel; Lloveras, Vega; Vidal-Gancedo, José; Ventura, Salvador; Vendrell, Josep; Sodupe, Mariona; González-Duarte, Pilar

    2009-02-01

    Metal chelation is considered a rational therapeutic approach for interdicting Alzheimer's amyloid pathogenesis. At present, enhancing the targeting and efficacy of metal-ion chelating agents through ligand design is a main strategy in the development of the next generation of metal chelators. Inspired by the traditional dye Thioflavin-T, we have designed new multifunctional molecules that contain both amyloid binding and metal chelating properties. In silico techniques have enabled us to identify commercial compounds that enclose the designed molecular framework (M1), include potential antioxidant properties, facilitate the formation of iodine-labeled derivatives, and can be permeable through the blood-brain barrier. Iodination reactions of the selected compounds, 2-(2-hydroxyphenyl)benzoxazole (HBX), 2-(2-hydroxyphenyl)benzothiazole (HBT), and 2-(2-aminophenyl)-1H-benzimidazole (BM), have led to the corresponding iodinated derivatives HBXI, HBTI, and BMI, which have been characterized by X-ray diffraction. The chelating properties of the latter compounds toward Cu(II) and Zn(II) have been examined in the solid phase and in solution. The acidity constants of HBXI, HBTI, and BMI and the formation constants of the corresponding ML and ML2 complexes [M = Cu(II), Zn(II)] have been determined by UV-vis pH titrations. The calculated values for the overall formation constants for the ML2 complexes indicate the suitability of the HBXI, HBTI, and BMI ligands for sequestering Cu(II) and Zn(II) metal ions present in freshly prepared solutions of beta-amyloid (Abeta) peptide. This was confirmed by Abeta aggregation studies showing that these compounds are able to arrest the metal-promoted increase in amyloid fibril buildup. The fluorescence features of HBX, HBT, BM, and the corresponding iodinated derivatives, together with fluorescence microscopy studies on two types of pregrown fibrils, have shown that HBX and HBT compounds could behave as potential markers for the presence

  14. Synthesis of new AB monomers of amino modified PBO%单氨基改性PBO的AB型新单体的合成

    Institute of Scientific and Technical Information of China (English)

    赵德明; 吴锋; 陈中海; 吴纯鑫; 张建庭; 金宁人

    2016-01-01

    Using 4-methoxycarbonyl-2-nitro-benzoic acid (β-MNT) and 4-amino-6- nitroresorcinolhydrochloride (ANR·HCl) as the starting materials,we synthesized the intermediates 4-(5-nitro-6- hydroxybenzoxazole-2-yl)-3-nitro-methyl benzoate (3-NMNC),4-(5-nitro-6-hydroxybenzoxazole- 2-yl)-3-nitrobenzoate (3-NMNB),4-(5-nitro -6-hydroxy benzoxazole-2-yl)-3-aminobenzoic acid (3-NNBA) and the final product 4-(5-amino-6-hydroxy benzoxazole-2-yl)-3-aminobenzoic acid (3-AABA) through a series of reaction,including acylchloride,N-acylation,cyclization,hydrolysis and catalytichydrogenation reduction reaction. The optimal cyclization,hydrolysis and catalytichydrogenation reduction conditions were obtained. The experimental results for the cyclization reaction showed that taking diethyleneglycol dimethyl ether as solvent,the polyphosphoric acid(PPA) as dehydrant and the content of P2O5 in PPA of 84%,w(3-NMNC)∶w(PPA)=1∶9.5,the reaction temperature of 140℃ and the reaction time of 8h,we obtained the yield of 3-NMNB of 73.16% and its purity was 99.10% as determined by HPLC. The experimental results for the hydrolysis reaction showed that using ethanol and water as solvent,n(K2CO3)∶n(3-NMNB) = 1.8:1 and the reaction time of 2h,we got the yield of 3-NNBA of 74.19% and the purity was 98.59% as determined by HPLC. The experimental results for the hydrogenation reduction reaction showed that using methanol as solvent, w(10%Pd/C)∶w(3-NNBA)=1∶20,pressure of hydrogen of 1.0 MPa,reaction temperature of 80℃, reaction time of 5h,we had the yield of 3-AABA of 65.08% based on 3-NNBA and the purity was 99.43% as determined by HPLC.%研究了以4-(甲氧羰基)-2-硝基苯甲酸(β-MNT)与4-氨基-6-硝基间苯二酚盐酸盐(ANR·HCl)为原料经酰氯化、N-酰化、环合、水解和催化加氢还原等一系列反应合成得到中间体4-((2,4-二羟基-5-硝基)氨甲酰基)-3-硝基苯甲酸甲酯(3-NMNC)、4-(5-硝基-6-羟基-2-苯并唑基)-3-

  15. Determination of fluorescent whitening agents in plastic food contact materials by high performance liquid chromatography with fluorescence detector%高效液相色谱-荧光检测法测定食品接触材料塑料制品中荧光增白剂

    Institute of Scientific and Technical Information of China (English)

    焦艳娜; 丁利; 朱绍华; 傅善良; 龚强; 李晖; 王利兵

    2013-01-01

    建立了同时测定食品接触材料塑料制品(食品包装袋)中荧光增白剂的高效液相色谱-荧光检测法.样品用20 mL 三氯甲烷作提取剂,超声提取30 min,提取温度为40℃,用高效液相色谱进行定性定量分析.采用EclipseXDB-C18(250 mm×4.6 mm,5μm)为分析柱,以5 mmol/L乙酸铵溶液和乙腈为流动相,梯度洗脱,荧光激发波长为350 nm,发射波长为430 nm.结果显示,4种荧光增白剂4,4'-双[2-(邻氰苯基)乙烯基]苯(1,4-bis(4-cyanostyryl) benzene,C.I.199)、1,4-双(2-苯并恶唑)萘(1,4-bis (2-benzoxazolyl) naphthalene,C.I.367)、4,4'-双(2-甲氧苯乙烯基)联苯(4,4'-bis(2-methoxystyryl)biphenyl,C.I.378)和2,5-双(5-叔丁基-2-苯并恶唑基)噻吩(2,5-thiophenediylbis(5-tert-butyl-1,3-benzoxazole),C.I.184)可以较好地分离;检出限(S/N=3)分别为0.3、0.1、0.05、0.14 mg/L,定量限(S/N=10)分别为1.0、0.4、0.2、0.5 mg/L,回收率范围为78.9% ~ 101.1%,相对标准偏差小于10%,线性关系良好.该法简便、结果准确、灵敏度高,能够满足进出口食品包装材料塑料制品中荧光增白剂的日常检测.%A method for the determination of fluorescent whitening agents in plastic food contact materials by high performance liquid chromatography (HPLC) with fluorescence detector was developed. The samples were extracted with trichloromethane by sonication for 30 min at 40 ℃. The HPLC method was performed on a column of Eclipse XDB-C18 (250 mm ×4. 6 mm, 5 μm) by gradient elution using 5 mmol/L ammonium acetate and acetonitrile as the mobile phases, and detected by the fluorescence detector at an excitation wavelength of 350 nm and an emission wavelength of 430 nm. The experimental results indicated that the four fluorescent whitening agents were separated well. The limits of detection (LOD) (S/N = 3) were 0. 3 , 0. 1, 0. 05 , 0. 14 mg/L, and the limits of quantification (LOQ) (S/N = 10) were 1.0, 0. 4, 0. 2, 0. 5 mg/L for 1, 4-bis (4-cyanostyryl