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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...

  2. Synthesis and anticancer evaluation of imidazolinone and benzoxazole derivatives

    Directory of Open Access Journals (Sweden)

    Heba A. El-Hady

    2017-05-01

    Full Text Available A series of imidazolinone and benzoxazole derivatives (3 and 5 have been synthesized by the condensation of oxazolinone derivatives (2a–c with aniline and 2-hydroxyaniline. Acetyl derivatives (4, 6 and 7 were prepared via acetylation of compounds 3 and 5 with acetic anhydride and chloroacetyl chloride. The results revealed that imidazolinone and benzoxazole derivatives are potent against the cancer cell lines MCF-7 and HePG2. In particular, benzoxazole derivatives are more potent than imidazolinone derivatives.

  3. Benzoxazole derivatives suppress lipopolysaccharide-induced mast cell activation.

    Science.gov (United States)

    Cho, Kyung-Ah; Park, Minhwa; Kim, Yu-Hee; Choo, Hea-Young Park; Lee, Kyung Ho

    2018-05-01

    Mast cells are central regulators of allergic inflammation that function by releasing various proallergic inflammatory mediators, including histamine, eicosanoids and proinflammatory cytokines. Occasionally, bacterial infections may initiate or worsen allergic inflammation. A number of studies have indicated that activation of lipoxygenase in mast cells positive regulates allergic inflammatory responses by generating leukotrienes and proinflammatory cytokines. In the present study, the effects of benzoxazole derivatives on the lipopolysaccharide (LPS)‑induced expression of proinflammatory cytokines, production of histamine and surface expression of co‑stimulatory molecules on bone marrow-derived mast cells (BMMCs) were studied. The benzoxazole derivatives significantly reduced the expression of interleukin (IL)‑1β, IL‑6, IL‑13, tumor necrosis factor‑α, perilipin (PLIN) 2, and PLIN3 in BMMCs treated with LPS. Furthermore, histamine production was suppressed in BMMCs treated with LPS, or treated with phorbol-12-myristate-13-acetate/ionomycin. Benzoxazole derivatives marginally affected the surface expression of cluster of differentiation (CD)80 and CD86 on BMMCs in the presence of LPS, although LPS alone did not increase the expression of those proteins. Therefore, benzoxazole derivatives inhibited the secretion of proinflammatory cytokines in mast cells and may be potential candidate anti‑allergic agents to suppress mast cell activation.

  4. The thermodynamic properties of benzothiazole and benzoxazole

    Science.gov (United States)

    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.

  5. Dioxouranium(VI) complexes with benzimidazole and benzoxazole derivatives

    International Nuclear Information System (INIS)

    Mansingh, P.S.; Dash, K.C.

    1995-01-01

    UO 2 LηX 2 [X = NO 3 ,NCS and 0.5 SO 4 and when n = 2, L = 2-(2-hydroxyphyenyl) benzimidazole (HPBI) or 2-(2-aminophenyl) benzimidazole(APBI) and for n=1, L = 2-(2-pyridyl) benzoxazole (PBO)] were synthesized and characterized by several physico chemical techniques including molar conductance data, IR, 1 H and 13 C NMR and thermogravimetric analysis. (author). 5 refs

  6. Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors.

    Science.gov (United States)

    Angeli, A; Peat, T S; Bartolucci, G; Nocentini, A; Supuran, C T; Carta, F

    2016-12-28

    A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Mechanistic studies revealed a pH dependent intramolecular oxidative deselenization, with ring closure due to an intramolecular nucleophilic attack of a phenoxide ion. All the benzoxazoles herein reported possessed a primary sulfonamide zinc binding group and showed effective inhibitory action on the enzymes, carbonic anhydrases.

  7. Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes.

    Science.gov (United States)

    Aksenov, Alexander V; Smirnov, Alexander N; Aksenov, Nicolai A; Bijieva, Asiyat S; Aksenova, Inna V; Rubin, Michael

    2015-04-14

    PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to produce N-hydroxyimidamides. The latter undergo sequential acid-promoted cyclocondensation with ortho-OH or ortho-NHR moieties to afford benzoxazoles and benzimidazoles, respectively.

  8. Exploring the biocombinatorial potential of benzoxazoles: generation of novel caboxamycin derivatives.

    Science.gov (United States)

    Losada, Armando A; Méndez, Carmen; Salas, José A; Olano, Carlos

    2017-05-25

    The biosynthesis pathway of benzoxazole compounds caboxamycin and nataxazole have been recently elucidated. Both compounds share one of their precursors, 3-hydroxyanthranilate (two units in the case of nataxazole). In addition, caboxamycin structure includes a salicylate moiety while 6-methylsalycilate is the third scaffold in nataxazole. Pathways cross-talk has been identified in caboxamycin producer Streptomyces sp. NTK937, between caboxamycin and enterobactin pathways, and nataxazole producer Streptomyces sp. Tü6176, between nataxazole and coelibactin pathways. These events represent a natural form of combinatorial biosynthesis. Eleven novel caboxamycin derivatives, and five putative novel derivatives, bearing distinct substitutions in the aryl ring have been generated. These compounds were produced by heterologous expression of several caboxamycin biosynthesis genes in Streptomyces albus J1074 (two compounds), by combinatorial biosynthesis in Streptomyces sp. NTK937 expressing nataxazole iterative polyketide synthase (two compounds) and by mutasynthesis using a nonproducing mutant of Streptomyces sp. NTK937 (12 compounds). Some of the compounds showed improved bioactive properties in comparison with caboxamycin. In addition to the benzoxazoles naturally biosynthesized by the caboxamycin and nataxazole producers, a greater structural diversity can be generated by mutasynthesis and heterologous expression of benzoxazole biosynthesis genes, not only in the respective producer strains but also in non-benzoxazole producers such as S. albus strains. These results show that the production of a wide variety of benzoxazoles could be potentially achieved by the sole expression of cbxBCDE genes (or orthologs thereof), supplying an external source of salicylate-like compounds, or with the concomitant expression of other genes capable of synthesizing salicylates, such as cbxA or natPK.

  9. Discovery of new antitubercular agents by combining pyrazoline and benzoxazole pharmacophores: design, synthesis and insights into the binding interactions

    Czech Academy of Sciences Publication Activity Database

    Rana, D. N.; Chhabria, M. T.; Shah, N. K.; Brahmkshatriya, Pathik

    2014-01-01

    Roč. 23, č. 5 (2014), s. 2218-2228 ISSN 1054-2523 Institutional support: RVO:61388963 Keywords : antitubercular * benzoxazole * interaction energy * molecular docking * pharmacophore * pyrazoline Subject RIV: CC - Organic Chemistry Impact factor: 1.402, year: 2014

  10. 99mTc complexes of benzimidazole and benzoxazole ligands and their biodistribution studies

    International Nuclear Information System (INIS)

    Kothari, K.; Manju, S.; Pillai, M.R.A.; Rath, N.; Dash, K.C.; Sarma, H.D.

    1997-01-01

    Complexation studies of 2 (2' -hydroxyphenyl)benzimidazole (HPBI) and 2(2' -pyridyl)benzoxazole (PBO) with 99m Tc were carried out. The complexes were characterised by TLC, paper electrophoresis and solvent extraction. The ligand HPBI forms complex in high yield (>90%). Biodistribution studies carried out with 99m Tc-HPBI complex in Swiss Albino mice showed rapid clearance of the complex from blood and excretion of the activity through hepatobiliary system. (author). 2 refs., 1 fig., 3 tabs

  11. 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.

  12. Relayed Regioselective Alkynylation/Olefination of Unsymmetrical Cyclic Diaryliodonium Species Catalyzed by Cu and Pd: Affording Fluorescent Cytotoxic Benzoxazoles.

    Science.gov (United States)

    Zhu, Daqian; Liu, Panpan; Lu, Wenhua; Wang, Haiwen; Luo, Bingling; Hu, Yumin; Huang, Peng; Wen, Shijun

    2015-12-21

    Although cyclic diaryliodonium species have the potential to act as valuable synthons for cascade transformations, they still remain largely unexplored. The regioselectivity associated with unsymmetrical cyclic diaryliodonium species has previously been known to pose a challenge. A regioselective relayed alkynylation and olefination of unsymmetrical cyclic diaryliodonium species has been achieved by installation of a directing amido group. These relayed transformations were delayed until an oxazole ring had formed, delivering a series of unique fluorescent benzoxazoles. Moreover, some of these synthetic benzoxazoles showed apparent inhibitory activity against malignant cancer cells. Further confocal visualization revealed that benzoxazoles targeted cell nuclei. These findings might provide a novel structural scaffold to develop desirable anticancer agents. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  13. 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...... with the rate-limiting electrophilic or concerted palladation. A mechanism, proposed on the basis of kinetic and computational studies, includes generation of isocyanophenolate as the key step. The DFT calculations suggest that the overall catalytic cycle is facile and is largely controlled by the C-H acidity...

  14. Gold nanoparticles supported on titanium dioxide: an efficient catalyst for highly selective synthesis of benzoxazoles and benzimidazoles.

    Science.gov (United States)

    Tang, Lin; Guo, Xuefeng; Yang, Yu; Zha, Zhenggen; Wang, Zhiyong

    2014-06-11

    A highly efficient and selective reaction for the synthesis of 2-substituted benzoxazoles and benzimidazoles catalyzed by Au/TiO2 has been developed via two hydrogen-transfer processes. This reaction has a good tolerance to air and water, a wide substrate scope, and represents a new avenue for practical C-N and C-O bond formation. More importantly, no additional additives, oxidants and reductants are required for the reaction and the catalyst can be recovered and reused readily.

  15. 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.

  16. OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature.

    Science.gov (United States)

    Meng, Xu; Wang, Yanmin; Wang, Yuanguang; Chen, Baohua; Jing, Zhenqiang; Chen, Gexin; Zhao, Peiqing

    2017-07-07

    In the presence of manganese oxide octahedral molecular sieve (OMS-2) supported copper hydroxide Cu(OH) x /OMS-2, aerobic synthesis of benzoxazoles from catechols and amines via domino oxidation/cyclization at room temperature is achieved. This heterogeneous benzoxazoles synthesis initiated by the efficient oxidation of catechols over Cu(OH) x /OMS-2 tolerates a variety of substrates, especially amines containing sensitive groups (hydroxyl, cyano, amino, vinyl, ethynyl, ester, and even acetyl groups) and heterocycles, which affords functionalized benzoxazoles in good to excellent yields by employing low catalyst loading (2 mol % Cu). The characterization and plausible catalytic mechanism of Cu(OH) x /OMS-2 are described. The notable features of our catalytic protocol such as the use of air as the benign oxidant and EtOH as the solvent, mild conditions, ease of product separation, being scalable up to the gram level, and superior reusability of catalyst (up to 10 cycles) make it more practical and environmentally friendly for organic synthesis.

  17. Highly efficient water-mediated approach to access benzazoles: metal catalyst and base-free synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles.

    Science.gov (United States)

    Bala, Manju; Verma, Praveen Kumar; Sharma, Deepika; Kumar, Neeraj; Singh, Bikram

    2015-05-01

    An efficient water-catalyzed method has been developed for the synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles in one step. The present method excludes the usage of toxic metal catalysts and bases to produce benzazoles in good to excellent yields. An efficient and versatile water-mediated method has been established for the synthesis of various 2-arylbenzazoles. The present protocol excludes the usage of any catalyst and additive provided excellent selectivities and yields with high functional group tolerance for the synthesis of 2-arylated benzimidazoles, benzoxazoles, and benzothiazoles. Benzazolones were also synthesized using similar reaction protocol.

  18. Synthesis and potential cytotoxic activity of some new benzoxazoles, imidazoles, benzimidazoles and tetrazoles.

    Science.gov (United States)

    Arulmurugan, Subramaniyan; Kavitha, Helen P

    2013-06-01

    2 The present work deals with the synthesis of some novel heterocyclic compounds such as benzoxazoles , 7, 13 and 19, imidazoles 3, 8, 14 and 20, benzimidazoles 4, 9, 15 and 21, and tetrazoles 10, 16, and 22. The synthesized compounds were characterized by IR, 1H NMR, mass spectrometry and elemental analysis. The compounds were evaluated for cytotoxicity against human cancer cell lines such as MCF-7 (breast cancer) and HT-29 (colon cancer) by the MTT assay method. Among the tested compounds, 4,4'-sulfonylbis(N-(2-(1H-benzo[d]imidazol- -2-yl)ethyl)aniline (9), N-bis(2-(benzo[d]oxazol-2-yl)-ethyl)- 6-phenyl-1,3,5-triazine-2,4-diamine (13), N-bis(2-(1H-benzo[ d]imidazol-2-yl)ethyl)-6-phenyl-1,3,5-triazine-2,4-diamine (15) and N-tris(2-1H-benzo[d]imidazol-2-yl)ethyl)- 1,3,5-triazine-2,4,6-triamine (21) showed potent cytotoxicity.

  19. 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)

  20. Modification of benzoxazole derivative by bromine-spectroscopic, antibacterial and reactivity study using experimental and theoretical procedures

    Science.gov (United States)

    Aswathy, V. V.; Alper-Hayta, Sabiha; Yalcin, Gözde; Mary, Y. Sheena; Panicker, C. Yohannan; Jojo, P. J.; Kaynak-Onurdag, Fatma; Armaković, Stevan; Armaković, Sanja J.; Yildiz, Ilkay; Van Alsenoy, C.

    2017-08-01

    N-[2-(2-bromophenyl)-1,3-benzoxazol-5-yl]-2-phenylacetamide (NBBPA) was synthesized in this study as an original compound in order to evaluate its antibacterial activity against representative Gram-negative and Gram-positive bacteria, with their drug-resistant clinical isolate. Microbiological results showed that this compound had moderate antibacterial activity. Study also encompassed detailed FT-IR, FT-Raman and NMR experimental and theoretical spectroscopic characterization and assignation of the ring breathing modes of the mono-, ortho- and tri-substituted phenyl rings is in agreement with the literature data. DFT calculations were also used to identify specific reactivity properties of NBBPA molecule based on the molecular orbital, charge distribution and electron density analysis, which indicated the reactive importance of carbonyl and NH2 groups, together with bromine atom. DFT calculations were also used for investigation of sensitivity of the NBBPA molecules towards the autoxidation mechanism, while molecular dynamics (MD) simulations were used to investigate the influence of water. The molecular docking results suggest that the compound might exhibit inhibitory activity against GyrB complex.

  1. Novel scintillating material 2-(4-styrylphenyl)benzoxazole for the fully digital and MRI compatible J-PET tomograph based on plastic scintillators.

    Science.gov (United States)

    Wieczorek, Anna; Dulski, Kamil; Niedźwiecki, Szymon; Alfs, Dominika; Białas, Piotr; Curceanu, Catalina; Czerwiński, Eryk; Danel, Andrzej; Gajos, Aleksander; Głowacz, Bartosz; Gorgol, Marek; Hiesmayr, Beatrix; Jasińska, Bożena; Kacprzak, Krzysztof; Kamińska, Daria; Kapłon, Łukasz; Kochanowski, Andrzej; Korcyl, Grzegorz; Kowalski, Paweł; Kozik, Tomasz; Krzemień, Wojciech; Kubicz, Ewelina; Kucharek, Mateusz; Mohammed, Muhsin; Pawlik-Niedźwiecka, Monika; Pałka, Marek; Raczyński, Lech; Rudy, Zbigniew; Rundel, Oleksandr; Sharma, Neha G; Silarski, Michał; Uchacz, Tomasz; Wiślicki, Wojciech; Zgardzińska, Bożena; Zieliński, Marcin; Moskal, Paweł

    2017-01-01

    A novel plastic scintillator is developed for the application in the digital positron emission tomography (PET). The novelty of the concept lies in application of the 2-(4-styrylphenyl)benzoxazole as a wavelength shifter. The substance has not been used as scintillator dopant before. A dopant shifts the scintillation spectrum towards longer wavelengths making it more suitable for applications in scintillators of long strips geometry and light detection with digital silicon photomultipliers. These features open perspectives for the construction of the cost-effective and MRI-compatible PET scanner with the large field of view. In this article we present the synthesis method and characterize performance of the elaborated scintillator by determining its light emission spectrum, light emission efficiency, rising and decay time of the scintillation pulses and resulting timing resolution when applied in the positron emission tomography. The optimal concentration of the novel wavelength shifter was established by maximizing the light output and it was found to be 0.05 ‰ for cuboidal scintillator with dimensions of 14 mm x 14 mm x 20 mm.

  2. Novel Triazole linked 2-phenyl benzoxazole derivatives induce apoptosis by inhibiting miR-2, miR-13 and miR-14 function in Drosophila melanogaster.

    Science.gov (United States)

    Mondal, Tanmoy; Lavanya, A V S; Mallick, Akash; Dadmala, Tulshiram L; Kumbhare, Ravindra M; Bhadra, Utpal; Bhadra, Manika Pal

    2017-06-01

    Apoptosis is an important phenomenon in multi cellular organisms for maintaining tissue homeostasis and embryonic development. Defect in apoptosis leads to a number of disorders like- autoimmune disorder, immunodeficiency and cancer. 21-22 nucleotides containing micro RNAs (miRNAs/miRs) function as a crucial regulator of apoptosis alike other cellular pathways. Recently, small molecules have been identified as a potent inducer of apoptosis. In this study, we have identified novel Triazole linked 2-phenyl benzoxazole derivatives (13j and 13h) as a negative regulator of apoptosis inhibiting micro RNAs (miR-2, miR-13 and miR-14) in a well established in vivo model Drosophila melanogaster where the process of apoptosis is very similar to human apoptosis. These compounds inhibit miR-2, miR-13 and miR-14 activity at their target sites, which induce an increased caspase activity, and in turn influence the caspase dependent apoptotic pathway. These two compounds also increase the mitochondrial reactive oxygen species (ROS) level to trigger apoptotic cell death.

  3. BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines: route to C2-alkenylated benzoxazoles and benzimidazoles.

    Science.gov (United States)

    Song, Xian-Rong; Qiu, Yi-Feng; Song, Bo; Hao, Xin-Hua; Han, Ya-Ping; Gao, Pin; Liu, Xue-Yuan; Liang, Yong-Min

    2015-02-20

    A novel BF3·Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a Csp-Csp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.

  4. 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.

  5. 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. Copyright © 2015 John Wiley & Sons, Ltd.

  6. 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

  7. 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

    International Nuclear Information System (INIS)

    Daengngern, Rathawat; Kungwan, Nawee

    2015-01-01

    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

  8. 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.

  9. Benzoxazole and Benzothiazole Antirust Greases. Work Unit Directive (WUD) 51

    National Research Council Canada - National Science Library

    Christian, John

    1980-01-01

    ...) and polytetrafluoroethylene (PTFE) thickeners. Testing has shown that one percent concentrations of the additives in the grease formulations provide inhibition against rusting of ferrous metal components under conditions of high humidity...

  10. 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.

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

    KAUST Repository

    Ming Xu, Yi; Le, Ngoc Lieu; Zuo, Jian; Chung, Neal Tai-Shung

    2015-01-01

    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.

  13. 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.

  14. Preparation of Chemicals and Bulk Drug Substances for the U.S. Army Drug Development Program

    National Research Council Canada - National Science Library

    Blumbergs, Peter

    1997-01-01

    .... Types of compounds delivered include substituted quinolines, pyridines, oxazolidines, N-arylpropenamides, carboxylic acids, disulfides, sulfones, thiols and thiol ethers, benzimidazoles, benzoxazoles...

  15. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Volume 124 Issue 3 May 2012 pp 609-624. Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents · C Praveen A Nandakumar P Dheenkumar D Muralidharan P T Perumal · More Details Abstract Fulltext PDF. Microwave-assisted synthesis of benzothiazole and benzoxazole ...

  16. CCDC 1440984: Experimental Crystal Structure Determination : 4,8-bis(1,3-benzoxazol-2-yl)-2,6-dihexyl[1,3]thiazolo[5,4-f][1,3]benzothiazole

    KAUST Repository

    Conboy, Gary; Spencer, Howard J.; Angioni, Enrico; Kanibolotsky, Alexander L.; Findlay, Neil J.; Coles, Simon J.; Wilson, Claire; Pitak, Mateusz B.; Risko, Chad; Coropceanu, Veaceslav; Bredas, Jean-Luc; Skabara, Peter J.

    2016-01-01

    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  17. Synthesis of Some New 2-(3-Aryl-1-phenyl-4-pyrazolyl-benzoxazoles Using Hypervalent Iodine Mediated Oxidative Cyclization of Schiff’s Bases

    Directory of Open Access Journals (Sweden)

    Ajay Kumar

    2006-01-01

    Full Text Available Ten new 2-(3-aryl-1-phenyl-4-pyrazolylbenzoxazoles have been synthesized by oxidative intramolecular cyclization of the corresponding Schiff’s bases using iodobenzene diacetate in methanol as an oxidant.

  18. Pharmacophore combination as a useful strategy to discover new antitubercular agents

    Czech Academy of Sciences Publication Activity Database

    Rana, D. N.; Chhabria, M. T.; Shah, N. K.; Brahmkshatriya, Pathik

    2014-01-01

    Roč. 23, č. 1 (2014), s. 370-381 ISSN 1054-2523 Institutional support: RVO:61388963 Keywords : antitubercular * benzoxazole * interaction energy * molecular docking * pharmacophore * pyrazoline Subject RIV: CC - Organic Chemistry Impact factor: 1.402, year: 2014

  19. Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions.

    Science.gov (United States)

    Leckie, Stuart M; Harkness, Gavin J; Clarke, Matthew L

    2014-10-09

    As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

  20. Structure elucidation of the new citharoxazole from the Mediterranean deep-sea sponge Latrunculia (Biannulata) citharistae.

    Science.gov (United States)

    Genta-Jouve, Grégory; Francezon, Nellie; Puissant, Alexandre; Auberger, Patrick; Vacelet, Jean; Pérez, Thierry; Fontana, Angelo; Mourabit, Ali Al; Thomas, Olivier P

    2011-08-01

    Citharoxazole (1), a new batzelline derivative featuring a benzoxazole moiety, was isolated from the Mediterranean deep-sea sponge Latrunculia (Biannulata) citharistae Vacelet, 1969, together with the known batzelline C (2). This is the first chemical study of a Mediterranean Latrunculia species and the benzoxazole moiety is unprecedented for this family of marine natural products. The structure was mainly elucidated by the interpretation of NMR spectra and especially HMBC correlations. Copyright © 2011 John Wiley & Sons, Ltd.

  1. Benzoheterocyclic amodiaquine analogues with potent antiplasmodial activity: synthesis and pharmacological evaluation.

    Science.gov (United States)

    Ongarora, Dennis S B; Gut, Jiri; Rosenthal, Philip J; Masimirembwa, Collen M; Chibale, Kelly

    2012-08-01

    The synthesis and evaluation of antiplasmodial activity of benzothiazole, benzimidazole, benzoxazole and pyridine analogues of amodiaquine is hereby reported. Benzothiazole and benzoxazole analogues with a protonatable tertiary nitrogen atom possessed excellent activity against the W2 and K1 chloroquine resistant strains of Plasmodium falciparum, with IC(50)s ranging from 7 to 22 nM. Copyright © 2012 Elsevier Ltd. All rights reserved.

  2. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Home; Journals; Journal of Chemical Sciences. A Nandakumar. Articles written in Journal of Chemical Sciences. Volume 124 Issue 3 May 2012 pp 609-624. Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents · C Praveen A Nandakumar P Dheenkumar D Muralidharan ...

  3. Microwave-assisted one-pot synthesis of benzothiazole and ...

    Indian Academy of Sciences (India)

    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 ...

  4. Microwave assisted one-pot synthesis of benzothiazole and ...

    Indian Academy of Sciences (India)

    Dr.P.T.P

    1. Microwave assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents. C PRAVEEN a. , A NANDAKUMAR a. , P DHEENKUMAR b. , D MURALIDHARAN a and P T. PERUMAL a,. * a. Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600020,. Tamilnadu ...

  5. Fluorescent compounds for plastic scintillation applications

    International Nuclear Information System (INIS)

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

    1994-04-01

    Several 2-(2'-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 60 C source have also been performed

  6. Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst

    International Nuclear Information System (INIS)

    Xiang Gao; Bo Yu; Qingqing Mei; Zhenzhen Yang; Yanfei Zhao; Hongye Zhang; Leiduan Hao, Zhimin Liu

    2016-01-01

    B(C 6 F 5 ) 3 combined with atmospheric CO 2 was found to be highly effective for the cyclization of ortho substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields. (authors)

  7. Synthesis, photophysical property study of novel fluorescent 4-(1,3 ...

    Indian Academy of Sciences (India)

    Some of the benzoxazole derivatives exhibit diverse ... NSC-693638 and antibacterial agents;13 some exam- ples are UK-1, ..... 1H NMR (D2O Exchange of Comp .... test material in 10% (v/v) DMSO (usually a stock con- .... Refractive index of solvent for standard .... synthesis B M Trost, and I Flemming (eds) New York:.

  8. Radiopharmaceuticals

    Energy Technology Data Exchange (ETDEWEB)

    Hunt, F C; Wilson, J G

    1980-03-13

    The claim describes a reducing metal complex of a compound in a suitable form for labelling with technetium-99m for radiopharmaceutical purposes, the compound being a complex derived from an indene heterocycle structure. The indene heterocycle structure is selected from the group consisting of iminodiacetic acid derivates of benzimidazole, benzthiazole and benzoxazole.

  9. Discovery of potent inhibitors of soluble epoxide hydrolase by combinatorial library design and structure-based virtual screening.

    Science.gov (United States)

    Xing, Li; McDonald, Joseph J; Kolodziej, Steve A; Kurumbail, Ravi G; Williams, Jennifer M; Warren, Chad J; O'Neal, Janet M; Skepner, Jill E; Roberds, Steven L

    2011-03-10

    Structure-based virtual screening was applied to design combinatorial libraries to discover novel and potent soluble epoxide hydrolase (sEH) inhibitors. X-ray crystal structures revealed unique interactions for a benzoxazole template in addition to the conserved hydrogen bonds with the catalytic machinery of sEH. By exploitation of the favorable binding elements, two iterations of library design based on amide coupling were employed, guided principally by the docking results of the enumerated virtual products. Biological screening of the libraries demonstrated as high as 90% hit rate, of which over two dozen compounds were single digit nanomolar sEH inhibitors by IC(50) determination. In total the library design and synthesis produced more than 300 submicromolar sEH inhibitors. In cellular systems consistent activities were demonstrated with biochemical measurements. The SAR understanding of the benzoxazole template provides valuable insights into discovery of novel sEH inhibitors as therapeutic agents.

  10. Synthesis and Tuberculostatic Activity Evaluation of Novel Benzazoles with Alkyl, Cycloalkyl or Pyridine Moiety

    Directory of Open Access Journals (Sweden)

    Malwina Krause

    2018-04-01

    Full Text Available Compounds possessing benzimidazole system exhibit significant antituberculous activity. In order to examine how structure modifications affect tuberculostatic activity, a series of benzazole derivatives were synthesized and screened for their antitubercular activity. The compounds 1–20 were obtained by the reaction between o-diamine, o-aminophenol, or o-aminothiophenol with carboxylic acids or thioamides. The newly synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR spectra, and elemental analysis. Synthesized benzazoles were evaluated for their tuberculostatic activity toward Mycobacterium tuberculosis strains. Quantum chemical calculations were performed to study the molecular geometry and the electronic structure of benzimidazoles GK-151B, 4, 6, and benzoxazole 11, using the Gaussian 03W software (Gaussian, Inc., Wallingford, CT, USA. Three-dimensional structure of benzimidazoles 1–3, MC-9, and GK-151B was determined by ab initio calculation using Gamess-US software. The activity of the received benzimidazoles was moderate or good. All of the benzoxazoles and benzothiazoles demonstrated much lower activity. Benzoxazoles were less active by about 50 times, and benzothiazole by 100 times than the benzimidazole analogs. Quantum chemical calculations showed differences in the distribution of electrostatic potential in the benzazole system of benzimidazoles and benzoxazoles. Three-dimensional structure calculations revealed how the parity of the alkyl substituent at the C2 position impacts the activity. Benzimidazole system is essential for the antituberculosis activity that is associated with the presence of the imine nitrogen atom in N-1 position. Its replacement by an oxygen or sulfur atom results in a decrease of the activity. The parity of the alkyl substituent at the C-2 position also modifies the activity.

  11. Polyurea with luminophor fragments in polymer chain: synthesis and spectral properties

    Science.gov (United States)

    Novikova, Tamara S.; Barashkov, Nikolay N.; Sakhno, Tamara V.

    2003-12-01

    A series of aliphatic polyureas with chromophore moieties in the polymer chain, such as 7-amino-2(4"-aminophenyl)benzoxazole, have been prepared. The absorption and fluorescence spectra of these polymers as well as corresponding chromophore-containing model urea (product of condensation of 7-amino-2(4"-amino-2"-hydroxyphenyl)benzoxazole and phenylisocyanate) were studied and compared. It was found that the special feature of the model compound and polyureas is the large value of Stokes shift due to the presence of a hydroxy group in the ortho-position to the nitrogen atom of the benzoxazole ring. The model of the excited-state proton transfer in molecules containing fragments of 2-(2"-hydroxyphenyl)benzoxazole has been used for the description of bathochromic shift in emission spectra of polymer solutions and films. According to this model, the proton remains predominantly on the phenol oxygen while in the ground state (enol form). Upon UV excitation, in the first excited singlet state, the phenol is a considerably stronger acid and the nitrogen is a stronger base. Thus, the proton is transferred from the oxygen site to the nitrogen site, and the isomer formed (S"1*) is more stable than the isomer before proton transfer (S1*) S"1* can be then regarded as a vibrationally excited form of S1*. Then the molecule de-excites to the ground state, emitting a photon. In the ground state the enol form is again the more stable form and the proton will then transfer back to the oxygen. S"o is also a vibrationally excited state of So. Because of this process the absorption and fluorescence spectra of model urea and polyureas do not intersect and the value of Stokes shift is about 6000 cm-1.

  12. 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

  13. 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.

  14. New Palladium-Catalyzed Domino Reaction with Intramolecular Ring Closure of an N-(2-Chloro-3-heteroaryl) arylamide: First Synthesis of Oxazolo[4,5-b] pyrazines

    DEFF Research Database (Denmark)

    Demmer, Charles S.; Hansen, Jacob C.; Kehler, Jan

    2014-01-01

    The synthesis of novel planar heterocycles is at the heart of basic research as such scaffolds constitute key building blocks in important diverse areas of research: drug discovery, material sciences, and pesticides. The well-known benzoxazole is often contained in drug candidates but tweaking its...... lipophilicity and target interaction points are often desired. In this respect, the oxazolo[4,5-b]pyrazine is an attractive heterocyclic scaffold as it possesses increased water solubility as well as two additional hydrogen bonding acceptors. We here report a new Pd(II)-catalyzed domino reaction comprising...... the first Pd(II)-assisted intramolecular cyclization of an N-(2-chloro-3-heteroaryl)arylamide and validate its value by application to the first synthesis of 2-substituted oxazolo[4,5-b]pyrazines. We demonstrate that a bidentate phosphorus ligand as well as the presence of an aromatic nitrogen atom...

  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. An abnormally slow proton transfer reaction in a simple HBO derivative due to ultrafast intramolecular-charge transfer events.

    Science.gov (United States)

    Alarcos, Noemí; Gutierrez, Mario; Liras, Marta; Sánchez, Félix; Douhal, Abderrazzak

    2015-07-07

    We report on the steady-state, picosecond and femtosecond time-resolved studies of a charge and proton transfer dye 6-amino-2-(2'-hydroxyphenyl)benzoxazole (6A-HBO) and its methylated derivative 6-amino-2-(2'-methoxyphenyl)benzoxazole (6A-MBO), in different solvents. With femtosecond resolution and comparison with the photobehaviour of 6A-MBO, we demonstrate for 6A-HBO in solution, the photoproduction of an intramolecular charge-transfer (ICT) process at S1 taking place in ∼140 fs or shorter, followed by solvent relaxation in the charge transferred species. The generated structure (syn-enol charge transfer conformer) experiences an excited-state intramolecular proton-transfer (ESIPT) reaction to produce a keto-type tautomer. This subsequent proton motion occurs in 1.2 ps (n-heptane), 14 ps (DCM) and 35 ps (MeOH). In MeOH, it is assisted by the solvent molecules and occurs through tunneling for which we got a large kinetic isotope effect (KIE) of about 13. For the 6A-DBO (deuterated sample in CD3OD) the global proton-transfer reaction takes place in 200 ps, showing a remarkable slow KIE regime. The slow ESIPT reaction in DCM (14 ps), not through tunnelling as it is not sensitive to OH/OD exchange, has however to overcome an energy barrier using intramolecular as well as solvent coordinates. The rich ESIPT dynamics of 6A-HBO in the used solutions is governed by an ICT reaction, triggered by the amino group, and it is solvent dependent. Thus, the charge injection to a 6A-HBO molecular frame makes the ICT species more stable, and the phenol group less acidic, slowing down the subsequent ESIPT reaction. Our findings bring new insights into the coupling between ICT and ESIPT reactions on the potential-energy surfaces of several barriers.

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

    Science.gov (United States)

    Ito, Hiroshi; Shinotoh, Hitoshi; Shimada, Hitoshi; Miyoshi, Michie; Yanai, Kazuhiko; Okamura, Nobuyuki; Takano, Harumasa; Takahashi, Hidehiko; Arakawa, Ryosuke; Kodaka, Fumitoshi; Ono, Maiko; Eguchi, Yoko; Higuchi, Makoto; Fukumura, Toshimitsu; Suhara, Tetsuya

    2014-04-01

    The characteristic neuropathological changes in Alzheimer's disease (AD) are deposition of amyloid senile plaques and neurofibrillary tangles. The (18)F-labeled amyloid tracer, [(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 [(11)C]Pittsburgh compound B (PIB) and [(18)F]FACT in the same subjects, and the regional uptakes of both radiotracers were directly compared. Two PET scans, one of each with [(11)C]PIB and [(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 [(18)F]FACT studies without partial volume correction, while significant differences were observed in [(11)C]PIB. After partial volume correction, the cerebral cortical uptake was significantly larger in AD patients than in normal control subjects for [(18)F]FACT studies as well as [(11)C]PIB. Relatively lower uptakes of [(11)C]PIB in distribution were observed in the medial side of the temporal cortex and in the occipital cortex as compared with [(18)F]FACT. Relatively higher uptake of [(11)C]PIB in distribution was observed in the frontal and parietal cortices. Since [(18)F]FACT might bind more preferentially to dense-cored amyloid deposition, regional differences in cerebral cortical uptake between [(11)C]PIB and [(18)F]FACT might be due to differences in regional distribution between diffuse and dense-cored amyloid plaque shown in the

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

    International Nuclear Information System (INIS)

    Ito, Hiroshi; Shinotoh, Hitoshi; Shimada, Hitoshi; Miyoshi, Michie; Takano, Harumasa; Takahashi, Hidehiko; Arakawa, Ryosuke; Kodaka, Fumitoshi; Ono, Maiko; Eguchi, Yoko; Higuchi, Makoto; Fukumura, Toshimitsu; Suhara, Tetsuya; Yanai, Kazuhiko; Okamura, Nobuyuki

    2014-01-01

    The characteristic neuropathological changes in Alzheimer's disease (AD) are deposition of amyloid senile plaques and neurofibrillary tangles. The 18 F-labeled amyloid tracer, [ 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 [ 11 C ]Pittsburgh compound B (PIB) and [ 18 F ]FACT in the same subjects, and the regional uptakes of both radiotracers were directly compared. Two PET scans, one of each with [ 11 C ]PIB and [ 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 [ 18 F ]FACT studies without partial volume correction, while significant differences were observed in [ 11 C ]PIB. After partial volume correction, the cerebral cortical uptake was significantly larger in AD patients than in normal control subjects for [ 18 F ]FACT studies as well as [ 11 C ]PIB. Relatively lower uptakes of [ 11 C ]PIB in distribution were observed in the medial side of the temporal cortex and in the occipital cortex as compared with [ 18 F ]FACT. Relatively higher uptake of [ 11 C ]PIB in distribution was observed in the frontal and parietal cortices. Since [ 18 F ]FACT might bind more preferentially to dense-cored amyloid deposition, regional differences in cerebral cortical uptake between [ 11 C ]PIB and [ 18 F ]FACT might be due to differences in regional distribution between diffuse and dense-cored amyloid plaque shown in the

  20. Identification of novel 2-benzoxazolinone derivatives with specific inhibitory activity against the HIV-1 nucleocapsid protein.

    Science.gov (United States)

    Gamba, Elia; Mori, Mattia; Kovalenko, Lesia; Giannini, Alessia; Sosic, Alice; Saladini, Francesco; Fabris, Dan; Mély, Yves; Gatto, Barbara; Botta, Maurizio

    2018-02-10

    In this report, we present a new benzoxazole derivative endowed with inhibitory activity against the HIV-1 nucleocapsid protein (NC). NC is a 55-residue basic protein with nucleic acid chaperone properties, which has emerged as a novel and potential pharmacological target against HIV-1. In the pursuit of novel NC-inhibitor chemotypes, we performed virtual screening and in vitro biological evaluation of a large library of chemical entities. We found that compounds sharing a benzoxazolinone moiety displayed putative inhibitory properties, which we further investigated by considering a series of chemical analogues. This approach provided valuable information on the structure-activity relationships of these compounds and, in the process, demonstrated that their anti-NC activity could be finely tuned by the addition of specific substituents to the initial benzoxazolinone scaffold. This study represents the starting point for the possible development of a new class of antiretroviral agents targeting the HIV-1 NC protein. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  1. Highly efficient blue OLEDs based on diphenylaminofluorenylstyrenes end-capped with heterocyclic aromatics

    Energy Technology Data Exchange (ETDEWEB)

    Oh, Suhyun [Department of Chemistry, Sungkyunkwan University, Suwon 440-746 (Korea, Republic of); Lee, Kum Hee; Kim, Young Kwan [Department of Information Display, Hongik University, Seoul 121-791 (Korea, Republic of); Yoon, Seung Soo, E-mail: ssyoon@skku.edu [Department of Chemistry, Sungkyunkwan University, Suwon 440-746 (Korea, Republic of)

    2012-10-15

    In this paper, we have designed four diphenylaminofluorenylstyrene derivatives end-capped with heterocyclic aromatic groups, such as 9-phenylcabazole, 4-dibenzofuran, 2-benzoxazole, 2-quinoxaline, respectively. These materials showed blue to red fluorescence with maximum emission wavelengths of 476–611 nm, respectively, which were dependent on the structural and electronic nature of end-capping groups. To explore the electroluminescent properties of these materials, multilayer OLEDs were fabricated in the following sequence: ITO/DNTPD (40 nm)/NPB (20 nm)/2% doped in MADN (20 nm)/Alq{sub 3} (40 nm)/Liq. (1 nm)/Al. Among those, a device exhibited a highly efficient blue emission with the maximum luminance of 14,480 cd/m{sup 2} at 9 V, the luminous efficiency of 5.38 cd/A at 20 mA/cm{sup 2}, power efficiency of 2.77 lm/W at 20 mA/cm{sup 2}, and CIE{sub x,y} coordinates of (0.147, 0.152) at 8 V, respectively.

  2. 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

  3. {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.

  4. β - amyloid imaging probes

    International Nuclear Information System (INIS)

    Jeong, Jae Min

    2007-01-01

    Imaging distribution of β - amyloid plaques in Alzheimer's disease is very important for early and accurate diagnosis. Early trial of the β -amyloid plaques includes using radiolabeled peptides which can be only applied for peripheral β - 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 β - amyloid plaques of Alzheimer patient's brain without success due to problem with BBB penetration. Thioflavin T derivatives gave breakthrough for β - 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 β - amyloid imaging agent

  5. Insight into eukaryotic topoisomerase II-inhibiting fused heterocyclic compounds in human cancer cell lines by molecular docking.

    Science.gov (United States)

    Taskin, T; Yilmaz, S; Yildiz, I; Yalcin, I; Aki, E

    2012-01-01

    Etoposide is effective as an anti-tumour drug by inhibiting eukaryotic DNA topoisomerase II via establishing a covalent complex with DNA. Unfortunately, its wide therapeutic application is often hindered by multidrug resistance (MDR), low water solubility and toxicity. In our previous study, new derivatives of benzoxazoles, benzimidazoles and related fused heterocyclic compounds, which exhibited significant eukaryotic DNA topoisomerase II inhibitory activity, were synthesized and exhibited better inhibitory activity compared with the drug etoposide itself. To expose the binding interactions between the eukaryotic topoisomerase II and the active heterocyclic compounds, docking studies were performed, using the software Discovery Studio 2.1, based on the crystal structure of the Topo IIA-bound G-segment DNA (PDB ID: 2RGR). The research was conducted on a selected set of 31 fused heterocyclic compounds with variation in structure and activity. The structural analyses indicate coordinate and hydrogen bonding interactions, van der Waals interactions and hydrophobic interactions between ligands and the protein, as Topo IIA-bound G-segment DNA are responsible for the preference of inhibition and potency. Collectively, the results demonstrate that the compounds 1a, 1c, 3b, 3c, 3e and 4a are significant anti-tumour drug candidates that should be further studied.

  6. 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.

  7. First hyperpolarizability in a new benzimidazole derivative

    International Nuclear Information System (INIS)

    Rodembusch, Fabiano Severo; Buckup, Tiago; Segala, Maximiliano; Tavares, Luciana; Correia, Ricardo Rego Bordalo; Stefani, Valter

    2004-01-01

    A new benzimidazole, 2-(4'-amino-2'-hydroxyphenyl)-6-nitrobenzimidazole (LEN), with promising applications in nonlinear optics were synthesized, purified and characterized by classical techniques. The UV-Vis and steady-state fluorescence of LEN in solution were applied in order to characterize the photophysical behaviour of this new fluorescent dye. The Hyper-Rayleigh Scattering study indicates a remarkable increase in the β absolute value (1197.3 ± 1.2 x 10 -30 esu) of the LEN in acetone at 1064 nm, when comparing with a previously described benzoxazole (BO6). The ratio between the experimental β and the maximum theoretical value using a two-level model was also improved by a factor 6. Ab initio and semi-empirical calculations of the dipole moments and the first hyperpolarizability are also presented. The enhancement in the experimental hyperpolarizability value in relation to BO6 is explained in terms of the benzimidazolic ring basicity and a prototropic effect (annular tautomerism) present in the LEN, identified as a resonance-assisted hydrogen bond, which leads to a stronger electronic delocalization

  8. 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.

  9. White OLED in Hybrid Structure for Enhancing Color Purity.

    Science.gov (United States)

    Kim, Dong-Eun; Kang, Min-Jae; Park, Gwang-Ryeol; Lee, Burm-Jong; Kwon, Young-Soo; Shin, Hoon-Kyu

    2016-06-01

    We synthesized the red emission material, bis(1,4-bis(5-phenyloxazol-2-yl)phenyl) iridium(picolate) [Ir-complexes] and the blue emission material, bis (2-(2-hydroxyphenyl) benzoxazolate)zinc [Zn(HPB)2]. White Organic Light Emitting Diodes were fabricated by using Zn(HPB)2 for a blue emitting layer, Ir-complexes for a red emitting layer and a tris (8-hydroxy quinoline)aluminum [Alq3] for a green emitting layer. The important experimental results obtained, white OLED was fabricated by using double emitting layers of Zn(HPB)2 and Alq3:Ir-complexes, and hole blocking layer of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline[BCP]. We also varied the thickness of BCP. When the thickness of BCP layer was 5 nm, white emission was achieved. We obtained a maximum luminance of 5400 cd/m2 at a current density of 650 mA/cm2. The CIE coordinates was (0.339, 0.323) at voltage of 10 V.

  10. Recent advance in oxazole-based medicinal chemistry.

    Science.gov (United States)

    Zhang, Hui-Zhen; Zhao, Zhi-Long; Zhou, Cheng-He

    2018-01-20

    Oxazole compounds containing nitrogen and oxygen atoms in the five-membered aromatic ring are readily able to bind with a variety of enzymes and receptors in biological systems via diverse non-covalent interactions, and thus display versatile biological activities. The related researches in oxazole-based derivatives including oxazoles, isoxazoles, oxazolines, oxadiazoles, oxazolidones, benzoxazoles and so on, as medicinal drugs have been an extremely active topic, and numerous excellent achievements have been acquired. Noticeably, a large number of oxazole compounds as clinical drugs or candidates have been frequently employed for the treatment of various types of diseases, which have shown their large development value and wide potential as medicinal agents. This work systematically reviewed the recent researches and developments of the whole range of oxazole compounds as medicinal drugs, including antibacterial, antifungal, antiviral, antitubercular, anticancer, anti-inflammatory and analgesic, antidiabetic, antiparasitic, anti-obesitic, anti-neuropathic, antioxidative as well as other biological activities. The perspectives of the foreseeable future in the research and development of oxazole-based compounds as medicinal drugs are also presented. It is hoped that this review will serve as a stimulant for new thoughts in the quest for rational designs of more active and less toxic oxazole medicinal drugs. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  11. Fabrication and characterization of organic light-emitting diodes using zinc complexes as hole-blocking layer.

    Science.gov (United States)

    Kim, Won Sam; You, Jung Min; Lee, Burm-Jong; Jang, Yoon-Ki; Kim, Dong-Eun; Kwon, Young-Soo

    2006-11-01

    2-(2-Hydroxyphenyl)benzoxazole (HPB) was employed as organic ligand and the corresponding zinc complexes (Zn(HPB)2 and Zn(HPB)q) were synthesized. And their EL properties were characterized. The structures of zinc complexes were determined with FT-NMR, FT-IR, UV-Vis, and XPS. The thermal stability showed up to about 300 degrees C under nitrogen flow, which was measured by TGA. The photoluminescence (PL) of zinc complexes were measured from the DMF solution. The PL emitted in blue and yellow region, respectively. The EL devices were fabricated by the vacuum deposition. Two kinds of OLEDs devices were fabricated; ITO/NPB (40 nm)/Zn complexes (60 nm)/LiF/Al and ITO/NPB (40 nm)/Alq3 (60 nm)/Zn complexes (5 nm)/LiF/Al. Both of the EL properties as the emitting and the hole-blocking layer were investigated. The EL emission of Zn(HPB)q exhibited green light centered at 532 nm. The device showed a turn-on voltage at 5 V and a luminance of 6073 cd/m2 at 10 V. Meanwhile, the maximum EL the emission of the Zn(HPB)2 device was found to be at 447 nm. And the device showed a luminance of 2813 cd/m2 at 10 V. The ITO/NPB (40 nm)/Alq3 (60 nm)/Zn(HPB)2 (5 nm)/LiF/Al device showed increased luminance of L=17000 cd/m2 compared to L=12000 cd/m2 for similar device fabricated without the hole-blocking layer. And the turn-on voltage was significantly affected by the existence of the hole-blocking layer.

  12. Redox induced switching dynamics of a three colour electrochromic metallopolymer film

    International Nuclear Information System (INIS)

    Zeng Qiang; McNally, Andrea; Keyes, Tia E.; Forster, Robert J.

    2008-01-01

    Thin films of a novel Ru-phenolate based metallopolymer, [Ru(terpy)(box)PVP 20 ]PF 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 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 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 4 , the homogeneous charge transport diffusion coefficient, D CT , decreases from 3.6 ± 0.3 x 10 -13 to 2.7 ± 0.2 x 10 -13 cm 2 s -1 as the LiClO 4 concentration increases from 0.1 to 1.0 M. This weak dependence of D 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)

  13. Optimization of Aryl Amides that Extend Survival in Prion-Infected Mice.

    Science.gov (United States)

    Giles, Kurt; Berry, David B; Condello, Carlo; Dugger, Brittany N; Li, Zhe; Oehler, Abby; Bhardwaj, Sumita; Elepano, Manuel; Guan, Shenheng; Silber, B Michael; Olson, Steven H; Prusiner, Stanley B

    2016-09-01

    Developing therapeutics for neurodegenerative diseases (NDs) prevalent in the aging population remains a daunting challenge. With the growing understanding that many NDs progress by conformational self-templating of specific proteins, the prototypical prion diseases offer a platform for ND drug discovery. We evaluated high-throughput screening hits with the aryl amide scaffold and explored the structure-activity relationships around three series differing in their N-aryl core: benzoxazole, benzothiazole, and cyano. Potent anti-prion compounds were advanced to pharmacokinetic studies, and the resulting brain-penetrant leads from each series, together with a related N-aryl piperazine lead, were escalated to long-term dosing and efficacy studies. Compounds from each of the four series doubled the survival of mice infected with a mouse-passaged prion strain. Treatment with aryl amides altered prion strain properties, as evidenced by the distinct patterns of neuropathological deposition of prion protein and associated astrocytic gliosis in the brain; however, none of the aryl amide compounds resulted in drug-resistant prion strains, in contrast to previous studies on compounds with the 2-aminothiazole (2-AMT) scaffold. As seen with 2-AMTs and other effective anti-prion compounds reported to date, the novel aryl amides reported here were ineffective in prolonging the survival of transgenic mice infected with human prions. Most encouraging is our discovery that aryl amides show that the development of drug resistance is not an inevitable consequence of efficacious anti-prion therapeutics. Copyright © 2016 by The American Society for Pharmacology and Experimental Therapeutics.

  14. 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

    2010-07-01

    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.

  15. Fluorescent zinc sensor with minimized proton-induced interferences: photophysical mechanism for fluorescence turn-on response and detection of endogenous free zinc ions.

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    Kwon, Ji Eon; Lee, Sumin; You, Youngmin; Baek, Kyung-Hwa; Ohkubo, Kei; Cho, Jaeheung; Fukuzumi, Shunichi; Shin, Injae; Park, Soo Young; Nam, Wonwoo

    2012-08-20

    A new fluorescent zinc sensor (HNBO-DPA) consisting of 2-(2'-hydroxy-3'-naphthyl)benzoxazole (HNBO) chromophore and a di(2-picolyl)amine (DPA) metal chelator has been prepared and examined for zinc bioimaging. The probe exhibits zinc-induced fluorescence turn-on without any spectral shifts. Its crystal structure reveals that HNBO-DPA binds a zinc ion in a pentacoordinative fashion through the DPA and HNBO moieties. Steady-state photophysical studies establish zinc-induced deprotonation of the HNBO group. Nanosecond and femtosecond laser flash photolysis and electrochemical measurements provide evidence for zinc-induced modulation of photoinduced electron transfer (PeT) from DPA to HNBO. Thus, the zinc-responsive fluorescence turn-on is attributed to suppression of PeT exerted by deprotonation of HNBO and occupation of the electron pair of DPA, a conclusion that is further supported by density functional theory and time-dependent density functional theory (DFT/TD-DFT) calculations. Under physiological conditions (pH 7.0), the probe displays a 44-fold fluorescence turn-on in response to zinc ions with a K(d) value of 12 pM. The fluorescent response of the probe to zinc ions is conserved over a broad pH range with its excellent selectivity for zinc ions among biologically relevant metal ions. In particular, its sensing ability is not altered by divalent transition metal ions such as Fe(II), Cu(II), Cd(II), and Hg(II). Cell experiments using HNBO-DPA show its suitability for monitoring intracellular zinc ions. We have also demonstrated applicability of the probe to visualize intact zinc ions released from cells that undergo apoptosis. More interestingly, zinc-rich pools in zebrafish embryos are traced with HNBO-DPA during early developmental stages. The results obtained from the in vitro and in vivo imaging studies demonstrate the practical usefulness of the probe to detect zinc ions.

  16. Nonsteroidal anti-inflammatory drug flufenamic acid is a potent activator of AMP-activated protein kinase.

    Science.gov (United States)

    Chi, Yuan; Li, Kai; Yan, Qiaojing; Koizumi, Schuichi; Shi, Liye; Takahashi, Shuhei; Zhu, Ying; Matsue, Hiroyuki; Takeda, Masayuki; Kitamura, Masanori; Yao, Jian

    2011-10-01

    Flufenamic acid (FFA) is a nonsteroidal anti-inflammatory drug (NSAID). It has anti-inflammatory and antipyretic properties. In addition, it modulates multiple channel activities. The mechanisms underlying the pharmacological actions of FFA are presently unclear. Given that AMP-activated protein kinase (AMPK) has both anti-inflammatory and channel-regulating functions, we examined whether FFA induces AMPK activation. 1) Exposure of several different types of cells to FFA resulted in an elevation of AMPKα phosphorylation at Thr172. This effect of FFA was reproduced by functionally and structurally similar mefenamic acid, tolfenamic acid, niflumic acid, and meclofenamic acid. 2) FFA-induced activation of AMPK was largely abolished by the treatment of cells with 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid tetrakis(acetoxymethyl ester) (an intracellular Ca(2+) chelator) or depletion of extracellular Ca(2+), whereas it was mimicked by stimulation of cells with the Ca(2+) ionophore 5-(methylamino)-2-({(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid (A23187) or ionomycin. 3) FFA triggered a rise in intracellular Ca(2+), which was abolished by cyclosporine, a blocker of mitochondrial permeability transition pore. Cyclosporine also abolished FFA-induced activation of AMPK. 4) Inhibition of Ca(2+)/calmodulin-dependent kinase kinase β (CaMKKβ) with 7-oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid acetate (STO-609) or down-regulation of CaMKKβ with short interfering RNA largely abrogated FFA-induced activation of AMPK. 5) FFA significantly suppressed nuclear factor-κB activity and inducible nitric-oxide synthase expression triggered by interleukin-1β and tumor necrosis factor α. This suppression was also largely abrogated by STO-609. Taken together, we conclude that FFA induces AMPK activation through the Ca(2+)-CaMKKβ pathway

  17. A modified method of 3D-SSP analysis for amyloid PET imaging using [¹¹C]BF-227.

    Science.gov (United States)

    Kaneta, Tomohiro; Okamura, Nobuyuki; Minoshima, Satoshi; Furukawa, Katsutoshi; Tashiro, Manabu; Furumoto, Shozo; Iwata, Ren; Fukuda, Hiroshi; Takahashi, Shoki; Yanai, Kazuhiko; Kudo, Yukitsuka; Arai, Hiroyuki

    2011-12-01

    Three-dimensional stereotactic surface projection (3D-SSP) analyses have been widely used in dementia imaging studies. However, 3D-SSP sometimes shows paradoxical results on amyloid positron emission tomography (PET) analyses. This is thought to be caused by errors in anatomical standardization (AS) based on an (18)F-fluorodeoxyglucose (FDG) template. We developed a new method of 3D-SSP analysis for amyloid PET imaging, and used it to analyze (11)C-labeled 2-(2-[2-dimethylaminothiazol-5-yl]ethenyl)-6-(2-[fluoro]ethoxy)benzoxazole (BF-227) PET images of subjects with mild cognitive impairment (MCI) and Alzheimer's disease (AD). The subjects were 20 with MCI, 19 patients with AD, and 17 healthy controls. Twelve subjects with MCI were followed up for 3 years or more, and conversion to AD was seen in 6 cases. All subjects underwent PET with both FDG and BF-227. For AS and 3D-SSP analyses of PET data, Neurostat (University of Washington, WA, USA) was used. Method 1 involves AS for BF-227 images using an FDG template. In this study, we developed a new method (Method 2) for AS: First, an FDG image was subjected to AS using an FDG template. Then, the BF-227 image of the same patient was registered to the FDG image, and AS was performed using the transformation parameters calculated for AS of the corresponding FDG images. Regional values were normalized by the average value obtained at the cerebellum and values were calculated for the frontal, parietal, temporal, and occipital lobes. For statistical comparison of the 3 groups, we applied one-way analysis of variance followed by the Bonferroni post hoc test. For statistical comparison between converters and non-converters, the t test was applied. Statistical significance was defined as p SSP analysis of amyloid PET imaging possible. This new method of 3D-SSP analysis for BF-227 PET could prove useful for detecting differences between normal groups and AD and MCI groups, and between converters and non-converters.