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Sample records for benzothiazoles

  1. Bioactive thiazole and benzothiazole derivatives.

    Science.gov (United States)

    Rouf, Abdul; Tanyeli, Cihangir

    2015-06-05

    The heterocycles are the versatile compounds existing in almost all natural products and synthetic organic compounds, usually associated with one or the other biological activity. Among the heterocycles the thiazoles and benzothiazoles occupy a prominent position. They possess a broad range of biological activities and are found in many potent biologically active molecules and drugs such as vitamin thiamine, sulfathiazol (antimicrobial drug), ritonavir (antiretroviral drug), abafungin (antifungal drug) and tiazofurin (antineoplastic drug). The thiazole moiety is abundantly found in natural products while benzothiazole moiety is rare. In this review we disclose the literature reports of thiazoles and benzothiazoles possessing different biological activities.

  2. Sedimentary environment indicators: Benzothiazole and its derivatives

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Benzothiazoles distributional characteristics of crude oils and non-hydrocarbon fractions of source rocks in Mangya depression of the Qaidam Basin, Lunnan oil field in the Tarim Basin, Kelamayi oil field in the Junggar Basin and the Tulufan Basin oil field were analyzed. It was found that the distributions of benzothiazole are remarkable diversity in different sedimentary environmental oils. The swamp crude oils contain high quantity of benzothiazole and relatively high quantity of alkylthio-benzothiazole and 2(3H)-benzothiazolone. But the quantity of the 2,2′-dithiobis- ben-zothiazole is relatively low. The abundance of benzothiazole and 2,2′-dithiobis-benzothiazole are relatively high in semi-brackish water lacustrine crude oils, but the quantity of alkylthio-benzothiazole and 2(3H)-benzothiazolone are rela-tively low. The benzothiazoles belong to weak acid and mild base compound, and their stabilization conditions relate to their environmental medium. The nitrogenous bases are in favor of alkalescence environment, while weak acid nitroge-nous compounds are the main stable products under the weak acid environment. Benzothiazoles have great signifi-cance in identifying the oil- and gas-formed environment and the geochemistry study of non-hydrocarbon fraction in the future.

  3. Potent and orally efficacious benzothiazole amides as TRPV1 antagonists.

    Science.gov (United States)

    Besidski, Yevgeni; Brown, William; Bylund, Johan; Dabrowski, Michael; Dautrey, Sophie; Harter, Magali; Horoszok, Lucy; Hu, Yin; Johnson, Dean; Johnstone, Shawn; Jones, Paul; Leclerc, Sandrine; Kolmodin, Karin; Kers, Inger; Labarre, Maryse; Labrecque, Denis; Laird, Jennifer; Lundström, Therese; Martino, John; Maudet, Mickaël; Munro, Alexander; Nylöf, Martin; Penwell, Andrea; Rotticci, Didier; Slaitas, Andis; Sundgren-Andersson, Anna; Svensson, Mats; Terp, Gitte; Villanueva, Huascar; Walpole, Christopher; Zemribo, Ronald; Griffin, Andrew M

    2012-10-01

    Benzothiazole amides were identified as TRPV1 antagonists from high throughput screening using recombinant human TRPV1 receptor and structure-activity relationships were explored to pinpoint key pharmacophore interactions. By increasing aqueous solubility, through the attachment of polar groups to the benzothiazole core, and enhancing metabolic stability, by blocking metabolic sites, the drug-like properties and pharmokinetic profiles of benzothiazole compounds were sufficiently optimized such that their therapeutic potential could be verified in rat pharmacological models of pain.

  4. Synthesis and electroluminescence properties of benzothiazole derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Fu Huiying [Department of Materials Science, Fudan University, Shanghai 200433 (China); Gao Xindong [State Key Laboratory of Applied Surface Physics, Fudan University, Shanghai 200433 (China); Zhong Gaoyu; Zhong Zhiyang [Department of Materials Science, Fudan University, Shanghai 200433 (China); Xiao Fei, E-mail: feixiao@fudan.edu.c [Department of Materials Science, Fudan University, Shanghai 200433 (China); Shao Bingxian [Department of Materials Science, Fudan University, Shanghai 200433 (China)

    2009-10-15

    Benzothiazole-based blue fluorescent materials N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylbenzenamine (BPPA) and N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylnaphthalen-1-amine (BPNA) were synthesized for use in organic light-emitting diodes (OLEDs). Electroluminescent device with a configuration of ITO/NPB/BPPA/BCP/Alq{sub 3}/LiF/Al showed a maximum brightness of 3760 cd/m{sup 2} at 14.4 V with the CIE coordinates of (0.16, 0.16). A current efficiency of 3.01 cd/A and an external quantum efficiency of 2.37% at 20 mA/cm{sup 2} were obtained from this device. Molecules derived from BPPA and BPNA with incorporated dicyanomethylidene, which is a functional group for most red fluorescent molecules, were designed, synthesized and characterized to study the red fluorescence properties of the benzothiazole derivatives.

  5. Medicinal significance of benzothiazole scaffold: an insight view.

    Science.gov (United States)

    Sharma, Prabodh Chander; Sinhmar, Alka; Sharma, Archana; Rajak, Harish; Pathak, Dharam Pal

    2013-04-01

    Heterocycles bearing nitrogen, sulphur and thiazole moieties constitute the core structure of a number of biologically interesting compounds. Benzothiazole, a group of xenobiotic compounds containing a benzene ring fused with a thiazole ring, are used worldwide for a variety of therapeutic applications. Benzothiazole and their heterocyclic derivatives represent an important class of compounds possessing a wide spectrum of biological activities. The myriad spectrum of medicinal properties associated with benzothiazole related drugs has encouraged the medicinal chemists to synthesize a large number of novel therapeutic agents. Several analogues containing benzothiazole ring system exhibit significant antitumour, antimicrobial, antidiabetic, anti-inflammatory, anticonvulsant, antiviral, antioxidant, antitubercular, antimalarial, antiasthmatic, anthelmintic, photosensitizing, diuretic, analgesic and other activities. This article is an attempt to present the research work reported in recent scientific literature on different pharmacological activities of benzothiazole compounds.

  6. Biological Aspects of Emerging Benzothiazoles: A Short Review

    Directory of Open Access Journals (Sweden)

    Ruhi Ali

    2013-01-01

    Full Text Available In recent years heterocyclic compounds analogues and derivatives have attracted wide attention due to their useful biological and pharmacological properties. Benzothiazole is among the usually occurring heterocyclic nuclei in many marine as well as natural plant products. Benzothiazole is a privileged bicyclic ring system with multiple applications. It is known to exhibit a wide range of biological properties including anticancer, antimicrobial, and antidiabetic, anticonvulsant, anti-inflammatory, antiviral, antitubercular activities. A large number of therapeutic agents are synthesized with the help of benzothiazole nucleus. During recent years there have been some interesting developments in the biological activities of benzothiazole derivatives. These compounds have special significance in the field of medicinal chemistry due to their remarkable pharmacological potentialities. This review is mainly an attempt to present the research work reported in the recent scientific literature on different biological activities of benzothiazole compounds.

  7. Mesogenic benzothiazole derivatives with methoxy substituents

    Indian Academy of Sciences (India)

    A K Prajapati; N L Bonde

    2006-03-01

    Two new mesogenic homologous series containing 6-methoxybenzothiazole ring at the terminus of the molecule, viz. 2-(4'--alkoxyphenylazo)-6-methoxybenzothiazoles and 2-[4'-(4"--alkoxybenzoyloxy) phenylazo]-6-methoxybenzothiazoles were synthesized. In series I, -butyloxy to -tetradecyloxy derivatives exhibit nematic mesophase. Smectic A mesophase commences from the -dodecyloxy derivative as a monotropic phase and is retained up to the last member synthesized. All the members of series II exhibit enantiotropic nematic mesophase. The mesomorphic properties of the present series are compared with other structurally related series to evaluate the effect of the benzothiazole ring and the methoxy substituent on mesomorphism.

  8. Synthesis and Antidiabetic Evaluation of Benzothiazole Derivatives

    Energy Technology Data Exchange (ETDEWEB)

    G, Mariappan; P, Prabhat; L, Sutharson; J, Banerjee; U, Patangia; S, Nath [Himalayan Pharmacy Institute, Majhitar (India)

    2012-04-15

    A novel series of benzothiazole derivatives were synthesized and assayed in vivo to investigate their hypogly-cemic activity by streptozotocin-induced diebetic model in rat. These derivatives showed considerable biological efficacy when compared to glibenclamide, a potent and well known antidiabetic agent as a reference drug. All the compounds were effective, amongst them 3d showed more prominent activity at 100 mg/kg p.o. The experimental results are statistically significant at p<0.01 and p<0.05 level.

  9. Functional roles of benzothiazole motif in antiepileptic drug research.

    Science.gov (United States)

    Amir, Mohammad; Hassan, Mohd Zaheen

    2013-12-01

    Benzothiazoles are promising candidates for the design of novel antiepileptic drugs. The endocyclic sulphur and nitrogen functions present in this heterocyclic nucleus have been shown to be critical for the anticonvulsant activity. The present review outlines the rational design and anticonvulsant potential of promising benzothiazole lead molecules. Particular focus has been placed on the structure activity relationship of different benzothiazole derivatives giving selected examples of molecules with significant activity being that these molecules may serve as prototypes for the development of more active antiepileptic drugs.

  10. [Degradation of benzothiazole in electro-assisted microbial reactor].

    Science.gov (United States)

    Liu, Chun-Miao; Ding, Jie; Liu, Xian-Shu; Cheng, Wang-Bin

    2014-11-01

    The oxidative degradation of benzothiazole (BTH) in a single-chamber electro-assisted microbial reactor was investigated. The effects of applied voltage and COD/BTH ratio on the performance of degrading benzothiazole were studied. The research showed that BTH was oxidized to 2-hydroxy-benzothiazole (OHBT), then thiazole ring scission, and BTH translated into 2-methylsulfonylaniline eventually. The degrading of benzothiazole was in conformity with the pseudo first-order kinetic model, and the pseudo first-order kinetic constant can be increased by raising the applied voltage and co-metabolism. When the applied voltage was 0.7 V and COD/BTH ratio was 30, the degradation rate was 96% in 48 h, achieving the detoxification of BTH, and that is advantageous to the biochemical treatment.

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

    Science.gov (United States)

    Singh, Meenakshi; Singh, Sushil K

    2014-01-01

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

  12. Proteomic profile of the Bradysia odoriphaga in response to the microbial secondary metabolite benzothiazole

    OpenAIRE

    Yunhe Zhao; Kaidi Cui; Chunmei Xu; Qiuhong Wang; Yao Wang; Zhengqun Zhang; Feng Liu; Wei Mu

    2016-01-01

    Benzothiazole, a microbial secondary metabolite, has been demonstrated to possess fumigant activity against Sclerotinia sclerotiorum, Ditylenchus destructor and Bradysia odoriphaga. However, to facilitate the development of novel microbial pesticides, the mode of action of benzothiazole needs to be elucidated. Here, we employed iTRAQ-based quantitative proteomics analysis to investigate the effects of benzothiazole on the proteomic expression of B. odoriphaga. In response to benzothiazole, 92...

  13. 40 CFR 180.288 - 2-(Thiocyanomethyl-thio)benzothiazole; tolerances for residues.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 23 2010-07-01 2010-07-01 false 2-(Thiocyanomethyl-thio)benzothiazole... Tolerances § 180.288 2-(Thiocyanomethyl-thio)benzothiazole; tolerances for residues. (a) General. Tolerances are established for residues of the fungicide 2-(thiocyanomethylthio)benzothiazole in or on...

  14. Molecular Modeling and Spectroscopic Studies of Benzothiazole

    Directory of Open Access Journals (Sweden)

    V. Sathyanarayanmoorthi

    2013-01-01

    Full Text Available The Fourier Transform (FT infrared and FT-Raman spectra of benzothiazole (BT have been recorded and analyzed. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated by ab initio and density functional theory (DFT methods. The assignments of the vibrational spectra have been carried out. The computed optimized geometric bond lengths and bond angles show good agreement with experimental data of the title compound. The calculated HOMO and LUMO energies indicate that charge transfer occurs within the molecule. Stability of the molecule due to conjugative interactions arising from charge delocalization has been analyzed using natural bond orbital (NBO analysis. The results show that the electron density (ED in the and antibonding orbital and second-order delocalization energies confirm the occurrence of intramolecular charge transfer (ICT. The calculated results were applied to simulate infrared and Raman spectra BT which show good agreement with recorded spectra.

  15. The thermodynamic properties of benzothiazole and benzoxazole

    Energy Technology Data Exchange (ETDEWEB)

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

    1991-08-01

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

  16. Benzothiazole sulfide compatibilized polypropylene/halloysite nanotubes composites

    Energy Technology Data Exchange (ETDEWEB)

    Liu Mingxian [Department of Polymer Materials and Engineering, South China University of Technology, Guangzhou 510640 (China); Guo Baochun, E-mail: psbcguo@scut.edu.cn [Department of Polymer Materials and Engineering, South China University of Technology, Guangzhou 510640 (China); Lei Yanda; Du Mingliang; Jia Demin [Department of Polymer Materials and Engineering, South China University of Technology, Guangzhou 510640 (China)

    2009-02-15

    Clay-philic benzothiazole sulfide, capable of donating electrons, is grafted onto polypropylene (PP) backbones when N-cyclohexyl-2-benzothiazole sulfonamide (CBS), a commonly used accelerator in the tire industry, is included in the processing of PP/halloysite nanotubes (HNTs) composites. CBS decomposes at elevated temperature and yields benzothiazole sulfide radicals, which react with the PP polymeric free radicals generated during the processing of the composites. On the other hand, the benzothiazole group of CBS is reactive to HNTs via electron transferring. The compatibilization between HNTs and PP is thus realized via interfacial grafting and electron transferring mechanism. The interfacial interactions in the compatibilized systems were fully characterized. Compared with the control sample, the dispersion of HNTs and the interfacial bonding are enhanced substantially in the compatibilized composites. The significantly improved mechanical properties and thermal properties of benzothiazole sulfide compatibilized PP/HNTs composites are correlated to the enhanced interfacial property. The present work demonstrates a novel interfacial design via interfacial grafting/electron transferring for the compatibilization of PP/clay composites.

  17. Dimethyl 3-acetyl-3-(1,3-benzothiazol-2-ylpentanedioate

    Directory of Open Access Journals (Sweden)

    Maher Izaaryene

    2008-12-01

    Full Text Available The title compound, C16H17NO5S, was one of two condensation products from the reaction of 1-(1,3-benzothiazol-2-ylpropan-2-one with methyl chloroacetate. The non-H atoms in each of the four substituent groups on the central quaternary C atom are virtually coplanar. The maximum deviations from the least-squares planes are 0.015 (2 and 0.020 (2 Å for the methyl C atoms in the methyl acetate substituents and 0.033 (1 Å for the linked C atom of the benzothiazole substituent. The S, C and N atoms in the thiazole ring of the benzothiazole substituent lie −0.037 (2, 0.046 (2 and −0.028 (2 Å, respectively, from the mean plane defined by the benzene ring atoms.

  18. New platinum(II complexes with benzothiazole ligands

    Directory of Open Access Journals (Sweden)

    José A. Carmona-Negrón

    2016-03-01

    Full Text Available Four new platinum(II complexes, namely tetraethylammonium tribromido(2-methyl-1,3-benzothiazole-κNplatinate(II, [NEt4][PtBr3(C8H7NS] (1, tetraethylammonium tribromido(6-methoxy-2-methyl-1,3-benzothiazole-κNplatinate(II, [NEt4][PtBr3(C9H9NOS] (2, tetraethylammonium tribromido(2,5,6-trimethyl-1,3-benzothiazole-κNplatinate(II, [NEt4][PtBr3(C10H11NS] (3, and tetraethylammonium tribromido(2-methyl-5-nitro-1,3-benzothiazole-κNplatinate(II, [NEt4][PtBr3(C8H6N2O2S] (4, have been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. These species are precursors of compounds with potential application in cancer chemotherapy. All four platinum(II complexes adopt the expected square-planar coordination geometry, and the benzothiazole ligand is engaged in bonding to the metal atom through the imine N atom (Pt—N. The Pt—N bond lengths are normal: 2.035 (5, 2.025 (4, 2.027 (5 and 2.041 (4 Å for complexes 1, 2, 3 and 4, respectively. The benzothiazole ligands are positioned out of the square plane, with dihedral angles ranging from 76.4 (4 to 88.1 (4°. The NEt4 cation in 3 is disordered with 0.57/0.43 occupancies.

  19. Cytotoxic activities of some benzothiazole-piperazine derivatives.

    Science.gov (United States)

    Gurdal, Enise Ece; Durmaz, Irem; Cetin-Atalay, Rengul; Yarim, Mine

    2015-01-01

    Synthesis, characterization and cytotoxic activities of ten benzothiazole-piperazine derivatives were reported. In vitro cytotoxic activities of compounds were screened against hepatocellular (HUH-7), breast (MCF-7) and colorectal (HCT-116) cancer cell lines by sulphorhodamine B assay. Based on the GI50 values of the compounds, most of the benzothiazole-piperazine derivatives are active against HUH-7, MCF-7 and HCT-116 cancer cell lines. Compound 1d is highly cytotoxic against all tested cancer cell lines. Further investigation of compound 1d by Hoechst Staining and Fluorescence-Activated Cell Sorting Analysis (FACS) revealed that this compound causes apoptosis by cell cycle arrest at subG1 phase.

  20. New potent calcimimetics: II. Discovery of benzothiazole trisubstituted ureas.

    Science.gov (United States)

    Deprez, Pierre; Temal, Taoues; Jary, Hélène; Auberval, Marielle; Lively, Sarah; Guédin, Denis; Vevert, Jean-Paul

    2013-04-15

    Following the identification of trisubstituted ureas as a promising new chemical series of allosteric modulators of the calcium sensing receptor (CaSR), we further explored the SAR around the urea substitution, leading to the discovery of benzothiazole urea compound 13. This compound is a potent calcimimetic with an EC50=20 nM (luciferase assay). Evaluated in an in vivo model of chronic renal failure (short term and long term in 5/6 nephrectomized rats), benzothiazole urea 13 significantly decreased PTH levels after oral administration while keeping calcemia within the normal range.

  1. Ferroelectric nanofibers with an embedded optically nonlinear benzothiazole derivative

    Science.gov (United States)

    Baptista, Rosa M. F.; Isakov, Dmitry; Raposo, M. Manuela M.; Belsley, Michael; Bdikin, Igor; Kholkin, Andrei L.; Costa, Susana P. G.; de Matos Gomes, Etelvina

    2014-07-01

    We report measurements of the molecular first hyperpolarizability, thermal stability, photophysical, piezoelectric, and ferroelectric properties of a benzothiazole derivative bearing an arylthiophene π-conjugated bridge both in solution and when embedded into a poly ( l-lactic acid) matrix in the form of electrospun fibers with an average diameter of roughly 500 nm. The embedded nanocrystalline phenylthienyl-benzothiazole with crystal sizes of about 1.4 nm resulted in a good piezoelectric response from these functionalized electrospun fibers, indicative of a polar crystalline structure.

  2. Synthesis and characterization of azo benzothiazole chromophore based liquid crystal macromers: Effects of substituents on benzothiazole ring and terminal group on mesomorphic, thermal and optical properties

    Energy Technology Data Exchange (ETDEWEB)

    Karim, Md. Rabiul [Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur (Malaysia); Sheikh, Md. Rezaul Karim, E-mail: rksheikh@um.edu.my [Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur (Malaysia); Salleh, Noordini M.; Yahya, Rosiyah; Hassan, Aziz [Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur (Malaysia); Hoque, Md. Asadul [Department of Materials Science and Engineering, University of Rajshahi, Rajshahi 6205 (Bangladesh); Chemical Resources Laboratory, Tokyo Institute of Technology, 4259-R1-25, Nagatsuta-Cho, Midori-Ku, Yokohama 226-8503 (Japan)

    2013-07-15

    A series of azo benzothiazole chromophore based liquid crystalline compounds having different substituents at the sixth position on benzothiazole moiety with methacrylate terminal group were synthesized and characterized by FTIR, {sup 1}H and {sup 13}C NMR. TGA investigations showed synthesized compounds were thermally stable. POM and DSC studies revealed that all the compounds showed liquid crystal behaviors. SAXS analysis exposed that all the investigated compounds exhibited lamellar structure. Compound with H at the sixth position on the benzothiazole ring revealed only smectic liquid crystal phase whereas compounds with CH{sub 3}, OCH{sub 3} and OC{sub 2}H{sub 5} groups showed both nematic and smectic liquid crystal phases. The formation of mesophases as well as temperature ranges of mesophases was greatly influenced by the sixth position electron pushing substituent on benzothiazole ring as well as terminal methacrylate group. The absorption maxima (λ{sub max}) of UV–vis spectra were bathochromically shifted with the replacement of sixth position hydrogen atom by the electron donating groups on benzothiazole chromophore. Macromer with OCH{sub 3} substituent exhibited highest fluorescence emission than other compounds. - Highlights: • Benzothiazole based liquid crystalline macromers were synthesized and characterized. • Sixth position substituents of benzothiazole influenced the mesophase properties. • Terminal methacrylate group also influenced the mesophase formation. • The absorption maxima were red shifted by the electron pushing groups. • OCH{sub 3} at 6th position of benzothiazole exhibited highest fluorescence emission.

  3. Synthesis, structure and photophysical properties of a 2-(1'-hydroxypyrenyl)benzothiazole.

    Science.gov (United States)

    Wang, Kangnan; Lv, Qiang; Chen, Ying; Chen, Hongyu; Liu, Zhiqiang; Cao, Duxia; Fang, Qi

    2016-01-15

    A pyrene-based 2-aryl-benzothiazole derivative, 2-(1'-hydroxypyrenyl)benzothiazole (1H2PBT), was synthesized. Its crystal structure and photophysical properties were investigated. In comparison with the generally studied parent compound, 2-(2'-hydroxyphenyl)benzothiazole (HBT), 1H2PBT exhibited red-shifted absorption and emission in solution, as well as impressive solid state emission with high efficiency (0.35).

  4. Synthesis, structure and photophysical properties of a 2-(1‧-hydroxypyrenyl)benzothiazole

    Science.gov (United States)

    Wang, Kangnan; Lv, Qiang; Chen, Ying; Chen, Hongyu; Liu, Zhiqiang; Cao, Duxia; Fang, Qi

    2016-01-01

    A pyrene-based 2-aryl-benzothiazole derivative, 2-(1‧-hydroxypyrenyl)benzothiazole (1H2PBT), was synthesized. Its crystal structure and photophysical properties were investigated. In comparison with the generally studied parent compound, 2-(2‧-hydroxyphenyl)benzothiazole (HBT), 1H2PBT exhibited red-shifted absorption and emission in solution, as well as impressive solid state emission with high efficiency (0.35).

  5. Proteomic profile of the Bradysia odoriphaga in response to the microbial secondary metabolite benzothiazole.

    Science.gov (United States)

    Zhao, Yunhe; Cui, Kaidi; Xu, Chunmei; Wang, Qiuhong; Wang, Yao; Zhang, Zhengqun; Liu, Feng; Mu, Wei

    2016-11-24

    Benzothiazole, a microbial secondary metabolite, has been demonstrated to possess fumigant activity against Sclerotinia sclerotiorum, Ditylenchus destructor and Bradysia odoriphaga. However, to facilitate the development of novel microbial pesticides, the mode of action of benzothiazole needs to be elucidated. Here, we employed iTRAQ-based quantitative proteomics analysis to investigate the effects of benzothiazole on the proteomic expression of B. odoriphaga. In response to benzothiazole, 92 of 863 identified proteins in B. odoriphaga exhibited altered levels of expression, among which 14 proteins were related to the action mechanism of benzothiazole, 11 proteins were involved in stress responses, and 67 proteins were associated with the adaptation of B. odoriphaga to benzothiazole. Further bioinformatics analysis indicated that the reduction in energy metabolism, inhibition of the detoxification process and interference with DNA and RNA synthesis were potentially associated with the mode of action of benzothiazole. The myosin heavy chain, succinyl-CoA synthetase and Ca(+)-transporting ATPase proteins may be related to the stress response. Increased expression of proteins involved in carbohydrate metabolism, energy production and conversion pathways was responsible for the adaptive response of B. odoriphaga. The results of this study provide novel insight into the molecular mechanisms of benzothiazole at a large-scale translation level and will facilitate the elucidation of the mechanism of action of benzothiazole.

  6. 5-Benzothiazole substituted pyrimidine derivatives as HCV replication (replicase) inhibitors.

    Science.gov (United States)

    Arasappan, Ashok; Bennett, Frank; Girijavallabhan, Vinay; Huang, Yuhua; Huelgas, Regina; Alvarez, Carmen; Chen, Lei; Gavalas, Stephen; Kim, Seong-Heon; Kosinski, Aneta; Pinto, Patrick; Rizvi, Razia; Rossman, Randall; Shankar, Bandarpalle; Tong, Ling; Velazquez, Francisco; Venkatraman, Srikanth; Verma, Vishal A; Kozlowski, Joseph; Shih, Neng-Yang; Piwinski, John J; MacCoss, Malcolm; Kwong, Cecil D; Clark, Jeremy L; Fowler, Anita T; Geng, Feng; Kezar, Hollis S; Roychowdhury, Abhijit; Reynolds, Robert C; Maddry, Joseph A; Ananthan, Subramaniam; Secrist, John A; Li, Cheng; Chase, Robert; Curry, Stephanie; Huang, Hsueh-Cheng; Tong, Xiao; Njoroge, F George

    2012-05-01

    Based on a previously identified HCV replication (replicase) inhibitor 1, SAR efforts were conducted around the pyrimidine core to improve the potency and pharmacokinetic profile of the inhibitors. A benzothiazole moiety was found to be the optimal substituent at the pyrimidine 5-position. Due to potential reactivity concern, the 4-chloro residue was replaced by a methyl group with some loss in potency and enhanced rat in vivo profile. Extensive investigations at the C-2 position resulted in identification of compound 16 that demonstrated very good replicon potency, selectivity and rodent plasma/target organ concentration. Inhibitor 16 also demonstrated good plasma levels and oral bioavailability in dogs, while monkey exposure was rather low. Chemistry optimization towards a practical route to install the benzothiazole moiety resulted in an efficient direct C-H arylation protocol.

  7. Structure-activity relationships of benzothiazole GPR35 antagonists.

    Science.gov (United States)

    Abdalhameed, Manahil M; Zhao, Pingwei; Hurst, Dow P; Reggio, Patricia H; Abood, Mary E; Croatt, Mitchell P

    2017-02-01

    The first structure-activity relationships for a benzothiazole scaffold acting as an antagonist at GPR35 is presented. Analogues were designed based on a lead compound that was previously determined to have selective activity as a GPR35 antagonist. The synthetic route was modular in nature to independently explore the role of the middle and both ends of the scaffold. The activities of the analogues illustrate the importance of all three segments of the compound.

  8. 2-(1,3-Benzothiazol-2-yl-6-ethoxyphenol

    Directory of Open Access Journals (Sweden)

    D. Lakshmanan

    2011-09-01

    Full Text Available In the title compound, C15H13NO2S, the benzothiazole unit is essentially planar [maximum deviation = −0.0099 (5 Å for the S atom] and is oriented at a dihedral angle of 4.8 (5° with respect to the benzene ring. An intramolecular O—H...N hydrogen bond generates an S(6 ring motif. The crystal packing is stabilized by C—H...π interactions.

  9. Fluorescent Properties of Manganese Halide Benzothiazole Inorganic-Organic Hybrids.

    Science.gov (United States)

    Yu, Hui; Mei, YingXuan; Wei, ZhenHong; Mei, GuangQuan; Cai, Hu

    2016-11-01

    The reaction of manganese (II) halides MnX2 and benzothiazole (btz) in the concentrated acids HX (X = Cl, Br) at 80 °C resulted in the formation of two inorganic-organic hybrid complexes: [(btz)2(MnX4)]·2H2O (X = Cl, 1; X = Br, 2). Both compounds showed green luminescence and exhibited moderate quantum yields of 43.17 % for 1 and 26.18 % for 2, which were directly originated from the tetrahedral coordination of Mn(2+) ion. Two organic - inorganic hybrids [(btz)2(MnX4)]·2H2O based on MnCl2, benzothiazole and halide acids emitted green light with the moderate quantum efficiencies when excited by 365 nm light. Graphical abstract Two organic-inorganic hybrids [(btz)2(MnX4)]·2H2O based on MnCl2, benzothiazole and halide acids emitted green light with the moderate quantum efficiencies when excited by 365 nm light.

  10. 40 CFR 721.5340 - Substituted benzothiazole-azo-substituted benzoquinoline nickel complex (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted benzothiazole-azo... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.5340 Substituted benzothiazole-azo... to reporting. (1) The chemical substance identified generically as substituted...

  11. New mesogenic Schiff base esters comprising benzothiazole moiety:Synthesis and mesomorphic properties

    Institute of Scientific and Technical Information of China (English)

    Sie Tiong Ha; Teck Ming Koh; Guan Yeow Yeap; Hong Cheu Lin; Jun Kit Beh; Yip Foo Win; Peng Lim Boey

    2009-01-01

    A homologous series of Schiff base esters,6-methoxy-2-(2-hydroxy-4-alkanoyloxybenzylidenamino)benzothiazoles,comprising a benzothiazole moiety as the core was synthesized.All the members of this series exhibited an enantiotropic nematic phase.The azomethine linkage along with the lateral hydroxyl and terminal methoxyl groups were found to exert an effect on the mesomorphic properties.

  12. Aqueous Synthesis of ZnSe/ZnS-2-R-Benzothiazole Nanocrystals with White Emission

    Directory of Open Access Journals (Sweden)

    Ying-Fan Liu

    2016-01-01

    Full Text Available We prepared water-soluble white light-emitting ZnSe/ZnS-2-R-benzothiazole nanocrystals (NCs, R = 2-hydroxy-5-(2,5-dimethyl-thienyl-phenyl. The penicillamine (Pen capped ZnSe/ZnS NCs were firstly prepared with high photoluminescence quantum yields (PL QY of 40%. Then they bond to 2-R-benzothiazole molecules, resulting in white light-emitting ZnSe/ZnS-2-R-benzothiazole NCs with QY of 75% over a 375 to 650 nm range of emission, which can be applied to white light-emitting diodes. The ZnSe/ZnS-2-R-benzothiazole NCs with two emission bands at around 451 and 557 nm were discussed and the possible mechanism of the interaction of ZnSe/ZnS NCs with 2-R-benzothiazole was also proposed.

  13. A fluorescent benzothiazole probe with efficient two-photon absorption

    Science.gov (United States)

    Echevarria, Lorenzo; Moreno, Iván; Camacho, José; Salazar, Mary Carmen; Hernández, Antonio

    2012-11-01

    In this work, we report the two-photon absorption of 2-[4-(dimethylamino)phenyl]-1,3-benzothiazole-6-carbonitrile (DBC) in DMSO solution pumping at 779 nm with a 10 ns pulse laser-Nd:YAG system. The obtained two-photon absorption cross-section in DBC (407 ± 18 GM) is considerably high. Because DBC is a novel compound and have high values of fluorescence quantum yield, this result is expected to have an impact in biomolecules detection, diagnosis and treatment of cancer. Similar structures have previously been reported to show remarkable antitumour effects.

  14. 1-(1,3-Benzothiazol-2-yl-3-benzoylthiourea

    Directory of Open Access Journals (Sweden)

    Muhammad Kalim Tahir

    2008-01-01

    Full Text Available The title compound, C15H11N3OS2, was synthesized from benzoyl thiocyanate and 2-aminobenzothiazole in dry acetone. The thiourea group is in the thioamide form. The molecules are stabilized by two intermolecular C—H...S and C—H...O hydrogen bonds. Intramolecular N—H...O hydrogen bonding results in a pseudo-S(6 planar ring with dihedral angles of 11.23 and 11.91° with the benzothiazole ring system and the phenyl ring, respectively.

  15. Novel Synthetic Route to a-Aminophosphonates Containing Benzothiazole Moiety

    Institute of Scientific and Technical Information of China (English)

    谷利军; 王锐; 黄相中; 金诚

    2012-01-01

    A novel and efficient synthetic route to a-aminophosphonates containing benzothiazole moiety via a cascade three-component reaction from conveniently available starting materials has been developed. The target compounds 3a-3g, 7 and 8a, 8b were evaluated for their anticancer activities against the cancer cell line HL-60 in vitro by the MTT method. Compound 3g showed good cancer inhibitory activity against the tested cell line. Further study is necessary to find out the potential antitumor activities.

  16. 2-(1,3-Benzothiazol-2-ylsulfanyl-1-phenylethanone

    Directory of Open Access Journals (Sweden)

    Hossein Loghmani-Khouzani

    2009-10-01

    Full Text Available In the molecule of the title compound, C15H11NOS2, the 1,3-benzothiazole ring is oriented at a dihedral angle of 6.61 (6° with respect to the phenyl ring. In the crystal structure, intermolecular C—H...O interactions link the molecules in a herring-bone arrangement along the b axis and π–π contacts between the thiazole and phenyl rings [centroid–centroid distance = 3.851 (1 Å] may further stabilize the structure.

  17. Crystal structure of C-2-benzothiazole-N-methylnitrone

    Directory of Open Access Journals (Sweden)

    Roman Doroschuk

    2015-08-01

    Full Text Available The molecule of the title compound {systematic name: N-[(benzothiazol-2-ylmethylidene]methylamine N-oxide}, C9H8N2OS, is close to planar [maximum deviation from the mean plane = 0.081 (2 Å], its conformation being stabilized by a strong intramolecular attractive S...O interaction [2.6977 (16 Å]. In the crystal, molecules are linked into centrosymmetric dimers by pairs of weak C—H...O hydrogen bonds.

  18. Coumarin benzothiazole derivatives as chemosensors for cyanide anions

    Science.gov (United States)

    Wang, Kangnan; Liu, Zhiqiang; Guan, Ruifang; Cao, Duxia; Chen, Hongyu; Shan, Yanyan; Wu, Qianqian; Xu, Yongxiao

    2015-06-01

    Four coumarin benzothiazole derivatives, N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (1), (Z)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide (2), 7-(diethylamino)-N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (3) and (Z)-7-(diethylamino)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide) (4), have been synthesized. Their crystal structures, photophysical properties in acetonitrile and recognition properties for cyanide anions have been investigated. All the compounds are generally planar, especially compound 1 exhibits perfect planarity with dihedral angle between benzothiazolyl group and coumarin group being only 3.63°. Coumarin benzothiazole compounds 1 and 3 can recognize cyanide anions by Michael addition reaction and compound 3 exhibits color change from yellow to colorless and green fluorescence was quenched completely, which can be observed by naked eye. Coumarin benzothiazolyliden compound 4 can recognize cyanide anions with fluorescence turn-on response based on the copper complex ensemble displacement mechanism.

  19. [Design, synthesis and activities of novel benzothiazole derivatives containing arylpiperazine].

    Science.gov (United States)

    Liu, Wen-Hu; Chang, Jin-Xia; Liu, Yi; Luo, Jie-Wei; Zhang, Jian-Wu

    2013-08-01

    Twenty-four novel benzothiazole derivatives containing arylpiperazine were designed and synthesized by bioisosterism principle. Anti-proliferative effect of these synthesized compounds against four cancer cell and two normal cell lines were evaluated in vitro by the standard MTT assay. Pharmacological test showed that most of the compounds exhibited potent antitumor activity. Some of the compounds (II2, II3, II6, II7) showed strong anti-proliferation activities against HepG2 and HeLa229 cell lines with the IC 50 values of 1.6-4.5 micromol x L(-1) and 2.5-5.3 micromol x L(-1), respectively, and compounds having cyan in p-substituted benzene ring (I4, I8, I12, II4, II8 and II12) were found to have better antitumor activities against AsPC-1 cell lines with the IC50 values of 5.2-11.3 micromol x L(-1). The structure-activity relationship of benzothiazole derivatives containing arylpiperazine was also discussed preliminarily.

  20. Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles

    Directory of Open Access Journals (Sweden)

    Kiran B. Gona

    2015-04-01

    Full Text Available Dicarba-closo-dodecaboranes, commonly known as carboranes, possess unique physico-chemical properties and can be used as hydrophobic moieties during the design of new drugs or radiotracers. In this work, we report the synthesis of two analogues of 2-(4-aminophenylbenzothiazole (a compound that was found to elicit pronounced inhibitory effects against certain breast cancer cell lines in vitro in which the phenyl ring has been substituted by a m-carborane cage. Two different synthetic strategies have been used. For the preparation of 1-(9-amino-1,7-dicarba-closo-dodecaboran-1-yl-benzo-thiazole, the benzothiazole group was first introduced on one of the cluster carbon atoms of m-carborane and the amine group was further attached in three steps. For the synthesis of 1-(9-amino-1,7-dicarba-closo-dodecaboran-1-yl-6-hydroxybenzothiazole, iodination was performed before introducing the benzothiazole group, and the amino group was subsequently introduced in six steps. Both compounds were radiolabelled with carbon-11 using [11C]CH3OTf as the labelling agent. Radiolabelling yields and radiochemical purities achieved should enable subsequent in vitro and in vivo investigations.

  1. Coumarin benzothiazole derivatives as chemosensors for cyanide anions.

    Science.gov (United States)

    Wang, Kangnan; Liu, Zhiqiang; Guan, Ruifang; Cao, Duxia; Chen, Hongyu; Shan, Yanyan; Wu, Qianqian; Xu, Yongxiao

    2015-06-05

    Four coumarin benzothiazole derivatives, N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (1), (Z)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide (2), 7-(diethylamino)-N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (3) and (Z)-7-(diethylamino)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide) (4), have been synthesized. Their crystal structures, photophysical properties in acetonitrile and recognition properties for cyanide anions have been investigated. All the compounds are generally planar, especially compound 1 exhibits perfect planarity with dihedral angle between benzothiazolyl group and coumarin group being only 3.63°. Coumarin benzothiazole compounds 1 and 3 can recognize cyanide anions by Michael addition reaction and compound 3 exhibits color change from yellow to colorless and green fluorescence was quenched completely, which can be observed by naked eye. Coumarin benzothiazolyliden compound 4 can recognize cyanide anions with fluorescence turn-on response based on the copper complex ensemble displacement mechanism.

  2. Second-order Nonlinear Optical Properties of a Series of Benzothiazole Derivatives

    Institute of Scientific and Technical Information of China (English)

    LIU,Xiao-Juan; LENG,Wei-Nan; FENG,Ji-Kang; REN,Ai-Min; ZHOU,Xin

    2003-01-01

    The second- order nonlinear optical ( NLO ) properties of a series of benzothiazole derivatives were studied by use of the ZINDO-SOS method. These chromphores are formed by a donor-π-bridge-acceptor system, based on a nitro group connected with benzothiazole as the acceptor and a hydroxyl-functional amino group as the donor. For the purpose of comparison, we also designed molecules in which nitrobenzene is an acceptor. The calculation results indicate that benzothiazole derivatives exhibit larger second-order polarizabilities than nitrobenzene derivatives. In order to clarify the origin of the NLO response of these chromophores, their electron properties were investigated as well. The benzothiazole derivatives are good candidates for application in electro-optical device due to their high optical nonlinearities, good thermla and photonic stability.

  3. Cure modification of natural rubber containing benzothiazole accelerators by some modified thiocarbamyl sulfenamides

    NARCIS (Netherlands)

    Datta, R.N.; Debnath, S.C.; Noordermeer, J.W.M.

    2003-01-01

    The effects of N-cyclopentamethylene thiocarbamyl-N-(cyclohexyl,thiocyclohexyl)sulfenamide (CPCTS) and N-oxydiethylene thiocarbamyl-N-(cyclohexyl,thiocyclohexyl)sulfenamide (ODCTS) as cure modifiers on the vulcanization of natural rubber (NR) containing benzothiazole accelerators were studied. CPCTS

  4. Tetranuclear zinc(II-oxy (benzothiazole-2-thiolate aggregate and copper(I phenylthiolate aggregate

    Directory of Open Access Journals (Sweden)

    Abir Goswami

    2015-12-01

    Full Text Available A tetranuclear zinc-oxy (benzothiazole-2-thiolate aggregate whose structure has a C3-axis passing through ZnO unit relating three other zinc ions and a tetranuclear copper(I phenylthiolate aggregate having each thiphenolate ligand bridging three copper ions are reported. These aggregates were prepared by hydrothermal reactions of 2,2′-dithiobis-(benzothiazole with zinc nitrate or copper(I iodide, respectively. The reaction of zinc nitrate passed through in situ abstraction of a oxy ligand from moisture to form a Zn4O core holding six 2-benzothiazolethiolate ligands, and during the formation of the aggregate, cleavage of S–S bond of 2,2′-dithiobis-(benzothiazole took place. Whereas, an aggregate formed by self-assembling of copper(I phenylthiolate was formed after extensive degradation of 2,2′-dithiobis-(benzothiazole during solvothermal reaction.

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

    Science.gov (United States)

    1991-02-01

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

  6. Mesomorphic behavior of new benzothiazole liquid crystals having Schiff base linker and terminal methyl group

    Institute of Scientific and Technical Information of China (English)

    Sie Tiong Ha; Kok Leei Foo; Hong Cheu Lin; Masato M.Ito; Kazuma Abe; Kenji Kunbo; S.Sreehari Sastry

    2012-01-01

    A homologous series of heterocycles,6-methyl-2-(4-alkoxybenzylidenamino)benzothiazoles,were synthesized and characterized using FT-IR,1H and 13C NMR and mass spectrometric analysis.Enantiotropic nematic phase was observed for shorter members.Smectic A phase only emerged from octyloxy derivative onwards.The terminal methyl group at the benzothiazole fragment and the Schiff base linkage influenced the mesomorphic behavior of the present series.

  7. Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives.

    Science.gov (United States)

    Gabr, Moustafa T; El-Gohary, Nadia S; El-Bendary, Eman R; El-Kerdawy, Mohamed M

    2014-10-06

    New series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives were synthesized and characterized by analytical and spectrometrical methods (IR, HRMS, (1)H and (13)C NMR). Nineteen of the synthesized compounds were selected by the National Cancer Institute (NCI), USA, to be screened for their antitumor activity at a single dose (10 μM) against a panel of 60 cancer cell lines. The most active compounds, 4, 6, 10, 14, 17 and 20 were selected for further evaluation at five dose level screening. Compounds 17 (GI50 = 0.44 μM, TGI = 1.2 μM and LC50 MG-MID = 6.6 μM) and 4 (GI50 = 0.77 μM, TGI = 2.08 μM and LC50 MG-MID = 11.74 μM) were proved to be the most active members in this study. 3D and 2D pharmacophoric maps for the structural features of both compounds were studied.

  8. Effects of the microbial secondary metabolite benzothiazole on the nutritional physiology and enzyme activities of Bradysia odoriphaga (Diptera: Sciaridae).

    Science.gov (United States)

    Zhao, Yunhe; Xu, Chunmei; Wang, Qiuhong; Wei, Yan; Liu, Feng; Xu, Shuangyu; Zhang, Zhengqun; Mu, Wei

    2016-05-01

    Bradysia odoriphaga (Diptera: Sciaridae) is the major pest that damages Chinese chive production. As a volatile compound derived from microbial secondary metabolites, benzothiazole has been determined to possess fumigant activity against B. odoriphaga. However, the mechanism of action of benzothiazole is not well understood. In the present study, fourth-instar larvae of B. odoriphaga were exposed to LC10 and LC30 of benzothiazole. Sublethal concentrations (LC10 and LC30) of benzothiazole significantly reduced the food consumption of the larvae on the second day after treatment (2 DAT). However, there were no significant changes in pupal weight among the different treatments. We also measured the protein, lipid, carbohydrate, and trehalose contents and the digestive enzyme activities of the larvae, and the results suggest that benzothiazole reduced the nutrient accumulation and decreased the digestive enzyme activities of B. odoriphaga. In addition, the activity of glutathione S-transferase was significantly decreased at 6h after treatment with benzothiazole, whereas general esterase activities were significantly increased at 6 and 24h after treatment. The results of this study indicate that benzothiazole interferes in the normal food consumption and digestion process by decreasing the activities of digestive enzymes. These results provide valuable information for understanding the toxicity of benzothiazole and for exploring volatile compound for the control of this pest.

  9. Imidazo[2,1-b]benzothiazoles. II. Synthesis and antiinflammatory activity of some imidazo[2,1-b]benzothiazoles.

    Science.gov (United States)

    El-Shorbagi, A N; Sakai, S; el-Gendy, M A; Omar, N; Farag, H H

    1989-11-01

    3-[2-[p-(Un)substituted phenyl]imidazo [2,1-b]benzothiazol-3- yl]propionic acid derivatives (2a--e) were prepared via the interaction of the corresponding 2-[p-(un)substituted phenyl]imidazo[2,1-b]benzothiazoles (1a--e) with acrylic acid in the presence of acetic anhydride and acetic acid. Esterification of 2a--e produced methyl esters (3a--e). Upon the interaction of 3a with m-chloroperbenzoic acid, the S-dioxide (4a) was obtained. Compound 5a was prepared from 4a by alkaline hydrolysis. Vilsmeier formylation for 1a--e produced novel [2-[p-(un)substituted phenyl]imidazo[2,1-b]benzothiazol-3- yl]formaldehyde derivatives (6a--e). Derivatives 6a--e reacted with ethyl bromoacetate to give ethyl 3-hydroxy-3-[2-[p-(un)substituted phenyl]imidazo[2,1-b]benzothiazol- 3-yl]propionate esters (7a--e). Compound dl-7a was resolved with l-(+)-tartaric acid. Compounds 2a--e showed weak or no activity in the carrageein-induced paw edema assay. Compound 4a significantly inhibited the leakage of pontamine-sky blue dye into the peritoneal cavity of mice, in the capillary permeability inhibition assay. Compound 5a inhibited the writhing by 62% in the acetic acid-induced writhing assay.

  10. Degradation of benzotriazole and benzothiazole in treatment wetlands and by artificial sunlight.

    Science.gov (United States)

    Felis, Ewa; Sochacki, Adam; Magiera, Sylwia

    2016-11-01

    Laboratory-scale experiments were performed using unsaturated subsurface-flow treatment wetlands and artificial sunlight (with and without TiO2) to study the efficiency of benzotriazole and benzothiazole removal and possible integration of these treatment methods. Transformation products in the effluent from the treatment wetlands and the artificial sunlight reactor were identified by high performance liquid chromatography coupled with tandem mass spectrometry. The removal of benzothiazole in the vegetated treatment wetlands was 99.7%, whereas the removal of benzotriazole was 82.8%. The vegetation positively affected only the removal of benzothiazole. The major transformation products in the effluents from the treatment wetlands were methylated and hydroxylated derivatives of benzotriazole, and hydroxylated derivatives of benzothiazole. Hydroxylation was found to be the main process governing the transformation pathway for both compounds in the artificial sunlight experiment (with and without TiO2). Benzotriazole was not found to be susceptible to photodegradation in the absence of TiO2. The integration of the sunlight-induced processes (with TiO2) with subsurface-flow treatment wetlands caused further elimination of the compounds (42% for benzotriazole and 58% for benzothiazole). This was especially significant for the elimination of benzotriazole, because the removal of this compound was 96% in the coupled processes.

  11. Benzothiazole derivatives bearing amide moiety: potential cytotoxic and apoptosis-inducing agents against cervical cancer.

    Science.gov (United States)

    Singh, Meenakshi; Modi, Arusha; Narayan, Gopeshwar; Singh, Sushil K

    2016-07-01

    Cervical cancer is a major cause of morbidity and mortality in women worldwide. In recent years, benzothiazole analogues have attracted considerable attention in anticancer research. Therefore, in this study, the earlier reported amide series of benzothiazole derivatives were investigated for their antiproliferative activity. The activity of amide derivatives was evaluated using the 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, flow cytometric analysis, apoptosis assay, and DNA fragmentation on two human cervical cancer cell lines: SiHa and C33-A. The data reported from this investigation indicated that benzothiazole derivatives show pronounced cytotoxicity in the HPV16-positive SiHa cells compared with HPV-negative C-33A cells. The in-vitro cytotoxicity of the compounds on the HEK-293 noncancer cell line was evaluated to establish selectivity. Cells treated with benzothiazole derivatives showed prominent morphological features as evidenced by cell shrinkage, membrane blebbing, apoptotic nuclei, and DNA fragmentation. The benzothiazole derivatives show accumulation of cells in the sub-G1 and S-phase of the cell cycle in SiHa and C33-A, respectively. In addition, these derivatives exert their beneficial effect by inducing apoptosis, in the chemoprevention of cervical cancer cells, and were further ascertained using a DNA fragmentation assay. The compounds studied showed potent cytotoxic and apoptotic properties against SiHa and C33-A cancer cell lines and thus represent an excellent starting point for further optimization of therapeutically effective anticancer drugs.

  12. New synthesis and biological evaluation of benzothiazole derivates as antifungal agents.

    Science.gov (United States)

    Herrera Cano, Natividad; Ballari, María S; López, Abel G; Santiago, Ana N

    2015-04-15

    In search of new antifungal agrochemicals that could replace commercially available, aryl-2-mercaptobenzothiazoles were synthesized. They were prepared by two methodologies, using both photostimulated reaction and microwave assisted reaction. These reactions took place without the use of metallic catalyst by a one-pot procedure with excellent yields (70-98%). Synthesized compounds were evaluated for fungal growth inhibition against Botrytis cinerea. Most of the compounds have an excellent antifungal activity, and three of these showed a superior inhibitory effect to commercial fungicide Triadimefon. IC50 values observed for 2-(phenylthio)benzothiazole, 2-(2-chlorophenylthio)benzothiazole, and 2-(3-chlorophenyl thio)benzothiazole were 0.75, 0.69, and 0.65 μg mL(-1), respectively.

  13. Synthesis and in vitro Evaluation of New Benzothiazole Derivatives as Schistosomicidal Agents

    Directory of Open Access Journals (Sweden)

    Mona A Mahran

    2007-03-01

    Full Text Available A series of benzothiazol-2-yl-dithiocarbamates 3a-d along with their copper complexes 4a-c were synthesized via the reaction of suitable alkyl, aralkyl or heteroaryl halides with the sodium salt of benzothiazol-2-yl-dithiocarbamic acid, followed by complexation with copper sulphate. N-(4-Acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl-N-benzothiazol-2-yl-acetamides 7a-c were synthesized by cyclization of the appropriate thiosemicarbazones 6a-c in acetic anhydride. Selected compounds were screened for in vitro schistosomicidal activity against Schistosoma mansoni at three different dosage levels (10, 50 and 100 μg/ mL. Three of these products, 4a-c, showed schistosomicidal activity similar to praziquantel, with 100% worm mortality at 10 μg/mL. These compounds would constitute a new class of potent schistosomicidal agents.

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

    Science.gov (United States)

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

    2014-04-22

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

  15. Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides.

    Science.gov (United States)

    Kamps, Jos J A G; Belle, Roman; Mecinović, Jasmin

    2013-02-21

    Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure-reactivity relationships, oxygen labeling experiments, and (in)direct detection of intermediates and products reveal that the reaction proceeds via oxygen attack, and that oxygen incorporated in the 2-hydroxybenzothiazole product derives from hydroxylamine. The reaction, which is performed under mild conditions, can be used as a deprotection method for cleavage of benzothiazole-2-sulfonyl-protected amino acids.

  16. Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions

    Directory of Open Access Journals (Sweden)

    Antonio Monopoli

    2015-06-01

    Full Text Available The Pd–benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji–Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.

  17. A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling

    KAUST Repository

    Shen, Chao

    2012-01-01

    Sugar-based benzothiazoles are a new class of molecules promising for many biological applications. Here, we have synthesized a wide range of sugar-based benzothiazoles from readily accessible glycosyl thioureas by chemoselective, palladium-catalyzed C-S coupling reactions. Corroborated by theoretical calculations, a mechanistic investigation indicates that the coordination to the palladium by a pivaloyl carbonyl group and the presence of intramolecular hydrogen bonding play important roles in the efficiency and chemoselectivity of reaction. These fluorescent glycoconjugates can be observed to readily enter mammalian tumor cells and exhibit potential in vitro antitumor activity. This journal is © The Royal Society of Chemistry 2012.

  18. Regioselective Synthesis of Some Pyrazole Scaffolds Attached to Benzothiazole and Benzimidazole Moieties

    Directory of Open Access Journals (Sweden)

    Nabila A. Kheder

    2014-01-01

    Full Text Available Condensation of 2-(benzothiazol-2-ylacetonitrile (1 or 2-(1-methyl-1H-benzimidazol-2-ylacetonitrile (2 with thiophene-2-carbaldehyde afforded the corresponding acrylonitrile derivatives 3 or 4, respectively. The 1,3-dipolar cycloaddition reaction of the acrylonitrile 3 or 4 with nitrile-imine 6 gave novel pyrazole derivatives pendant to benzothiazole and benzimidazole. The pyrazoline derivative 7 was converted into the corresponding pyrazole derivative 11 via thermal elimination of hydrogen cyanide upon heating in sodium ethoxide solution. The structures of the synthesized products were confirmed by IR, 1H NMR, and mass spectral techniques.

  19. 1-(6-Chloro-1,3-benzothiazol-2-ylhydrazine

    Directory of Open Access Journals (Sweden)

    B. Narayana

    2012-03-01

    Full Text Available The asymmetric unit of the title compound, C7H6ClN3S, consists of two crystallographically independent molecules (A and B. The dihedral angle between the benzothiazole ring system and the hydrazine group is 8.71 (6° in molecule A and 7.16 (6° in molecule B. The N—N—C—N and N—N—C—S torsion angles involving the hydrazine group are 170.89 (9 and −9.96 (13°, respectively, in molecule A and 172.50 (9 and −7.43 (13°, respectively, in molecule B. In the crystal, neighbouring molecules are connected via pairs of N—H...N hydrogen bonds, generating R22(8 ring motifs, and are connected further by N—H...N hydrogen bonds into sheets lying parallel to the ab plane. The crystal studied was an inversion twin, the refined ratio of the twin components being 0.50 (3:0.50 (3.

  20. Chrysin-benzothiazole conjugates as antioxidant and anticancer agents.

    Science.gov (United States)

    Mistry, Bhupendra M; Patel, Rahul V; Keum, Young-Soo; Kim, Doo Hwan

    2015-12-01

    7-(4-Bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, obtained from chrysin with 1,4-dibromobutane, was combined with a wide range of 6-substituted 2-aminobenzthiazoles, which had been prepared from the corresponding anilines with potassium thiocyanate. Free radical scavenging efficacies of newer analogues were measured using DPPH and ABTS assays, in addition to the assessment of their anticancer activity against cervical cancer cell lines (HeLa and CaSki) and ovarian cancer cell line (SK-OV-3) implementing the SRB assay. Cytotoxicity of titled compounds was checked using Madin-Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-r indicated remarkable antioxidant power as DPPH and ABTS(+) scavengers; particularly the presence of halogen(s) (6g, 6h, 6j-6l) was favourable with IC50 values comparable to the control ascorbic acid. Unsubstituted benzothiazole ring favored the activity of resultant compounds (6a and 6r) against HeLa cell line, whereas presence of chlorine (6g) or a di-fluoro group (6k) was a key to exert strong action against CaSki. Moreover, a mono-fluoro (6j) and a ketonic functionality (6o) were beneficial to display anticipated anticancer effects against ovarian cancer cell line SK-OV-3. The structural assignments of the new products were done on the basis of IR, (1)H NMR, (13)C NMR spectroscopy and elemental analysis.

  1. 2-[3-(1,3-Benzothiazol-2-yl-2,2-dimethylpropyl]-2-methyl-2,3-dihydro-1,3-benzothiazole

    Directory of Open Access Journals (Sweden)

    Sammer Yousuf

    2012-08-01

    Full Text Available In the title compound, C20H22N2S2, the five-membered thiazole ring of the 2-methyl-2,3-dihydro-1,3-benzothiazole unit has an envelope conformation. The dihedral angle between the planar [maximum deviation of 0.014 (1 Å for the S atom] benzothiazole ring system and the benzene ring is 78.37 (12°. Two intramolecular C—H...S hydrogen bonds are observed, forming rings of graph-set motif S(6. In the crystal, the molecules are consolidated in pairs through N—H...N hydrogen bonds and are arranged parallel to the b axis.

  2. In vitro, ex vivo, and in vivo determination of thyroid hormone modulating activity of benzothiazoles

    Science.gov (United States)

    As in vitro assays are increasingly used to screen chemicals for their potential to produce endocrine disrupting adverse effects, it is important to understand their predictive capacity. The potential for a set of six benzothiazoles to affect endpoints related to thyroid hormone ...

  3. Triphenylamine based benzimidazole and benzothiazole: Synthesis and applications in fluorescent chemosensors and laser dyes

    Energy Technology Data Exchange (ETDEWEB)

    Yang, Yang [State Key Laboratory of Luminescence and Applications, Changchun Institute of Optics Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); University of Chinese Academy of Sciences, Beijing 100039 (China); Li, Bin, E-mail: libinteacher@163.com [State Key Laboratory of Luminescence and Applications, Changchun Institute of Optics Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Zhang, Liming; Guan, Yunlong [State Key Laboratory of Luminescence and Applications, Changchun Institute of Optics Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China)

    2014-01-15

    Triphenylamine based fluorescent dyes TPA-benzimidazole and TPA-benzothiazole have been designed and synthesized. The TPA-benzimidazole chemosensor was tested for a number of metal ions and found to exhibit binding affinity for Fe{sup 3+} and Hg{sup 2+} in acetonitrile, and the fluorescence quenching was achieved through a PET process. The appearance of an isosbestic point in absorption titrations and Job's plot analysis supported 1:1 stoichiometries for Fe{sup 3+} and Hg{sup 2+} ions. Laser experiments showed that under transversal pumping with a Q-switched Nd:YAG (355 nm) laser in toluene, TPA-benzothiazole exhibits efficient and stable amplified spontaneous emissions (ASE) at 436 nm. -- Highlights: • Triphenylamine based fluorescent dyes TPA-benzimidazole and TPA-benzothiazole have been designed and synthesized. • The TPA-benzimidazole exhibits binding affinity for Fe{sup 3+} and Hg{sup 2+} in acetonitrile and the fluorescence quenching was achieved through a PET process. • Under transversal pumping at 355 nm in toluene, TPA-benzothiazole exhibits efficient and stable amplified spontaneous emissions (ASE) in 436 nm.

  4. Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

    NARCIS (Netherlands)

    Kamps, J.; Belle, R.; Mecinovic, J.

    2013-01-01

    Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure-reactivity relationships, oxygen labeling experiments, and (in)direct detect

  5. Hybrid Moving Bed Biofilm Reactor for the biodegradation of benzotriazoles and hydroxy-benzothiazole in wastewater

    DEFF Research Database (Denmark)

    Mazioti, Aikaterini A.; Stasinakis, Athanasios S.; Psoma, Aikaterini K.;

    2017-01-01

    A laboratory scale Hybrid Moving Bed Biofilm Reactor (HMBBR) was used to study the removal of five benzotriazoles and one benzothiazole from municipal wastewater. The HMBBR system consisted of two serially connected fully aerated bioreactors that contained activated sludge (AS) and K3-biocarriers...

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

    Indian Academy of Sciences (India)

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

    2012-05-01

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

  7. Antimalarial Activity of Small-Molecule Benzothiazole Hydrazones

    Science.gov (United States)

    Sarkar, Souvik; Siddiqui, Asim A.; Saha, Shubhra J.; De, Rudranil; Mazumder, Somnath; Banerjee, Chinmoy; Iqbal, Mohd S.; Nag, Shiladitya; Adhikari, Susanta

    2016-01-01

    We synthesized a new series of conjugated hydrazones that were found to be active against malaria parasite in vitro, as well as in vivo in a murine model. These hydrazones concentration-dependently chelated free iron and offered antimalarial activity. Upon screening of the synthesized hydrazones, compound 5f was found to be the most active iron chelator, as well as antiplasmodial. Compound 5f also interacted with free heme (KD [equilibrium dissociation constant] = 1.17 ± 0.8 μM), an iron-containing tetrapyrrole released after hemoglobin digestion by the parasite, and inhibited heme polymerization by parasite lysate. Structure-activity relationship studies indicated that a nitrogen- and sulfur-substituted five-membered aromatic ring present within the benzothiazole hydrazones might be responsible for their antimalarial activity. The dose-dependent antimalarial and heme polymerization inhibitory activities of the lead compound 5f were further validated by following [3H]hypoxanthine incorporation and hemozoin formation in parasite, respectively. It is worth mentioning that compound 5f exhibited antiplasmodial activity in vitro against a chloroquine/pyrimethamine-resistant strain of Plasmodium falciparum (K1). We also evaluated in vivo antimalarial activity of compound 5f in a murine model where a lethal multiple-drug-resistant strain of Plasmodium yoelii was used to infect Swiss albino mice. Compound 5f significantly suppressed the growth of parasite, and the infected mice experienced longer life spans upon treatment with this compound. During in vitro and in vivo toxicity assays, compound 5f showed minimal alteration in biochemical and hematological parameters compared to control. In conclusion, we identified a new class of hydrazone with therapeutic potential against malaria. PMID:27139466

  8. The washout effect during laundry on benzothiazole, benzotriazole, quinoline, and their derivatives in clothing textiles.

    Science.gov (United States)

    Luongo, Giovanna; Avagyan, Rozanna; Hongyu, Ren; Östman, Conny

    2016-02-01

    In two previous papers, the authors have shown that benzothiazole, benzotriazole, quinoline, and several of their derivatives are widespread in clothing textile articles. A number of these compounds exhibit allergenic and irritating properties and, due to their octanol-water partition coefficient, are prone to be absorbed by the skin. Moreover, they are slightly soluble in water, which could make washing of clothes a route of emission into the environment. In the present study, the washout effect of benzothiazole, benzotriazole, quinoline, and some of their derivatives has been investigated. Twenty-seven textile samples were analyzed before, as well as after five and ten times of washing. The most abundant analyte was found to be benzothiazole, which was detected in 85 % of the samples with an average concentration of 0.53 μg/g (median 0.44 μg/g), followed by quinoline, detected in 81 % of the samples with an average concentration of 2.42 μg/g (median 0.21 μg/g). The average decrease in concentration for benzothiazoles was 50 % after ten times washing, while it was around 20 % for quinolines. The average emission to household wastewater of benzothiazoles and quinolines during one washing (5 kg of clothes made from polyester materials) was calculated to 0.5 and 0.24 g, respectively. These results strongly indicate that laundering of clothing textiles can be an important source of release of these compounds to household wastewater and in the end to aquatic environments. It also demonstrates a potential source of human exposure to these chemicals since considerable amounts of the compounds remain in the clothes even after ten times of washing.

  9. An analysis on the transmission of electron density through sulphur atoms in the quaternization reactions of benzothiazoles

    Indian Academy of Sciences (India)

    B K Mishra; Sabita Patel

    2002-02-01

    The kinetics of quaternization of a number of 2-substituted benzothiazoles with alkyl iodides and phenacyl bromide have been studied in nitrobenzene. The order of reactivity of different substituted benzothiazoles has been found to be -H > NO2 > Cl. The relative reactivity of 2-amino and 2-methyl derivatives has been ascribed to a solvation phenomenon. The analysis of rho values from the Hammett equation suggests two possible routes for the transmission of electron density.

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

    Science.gov (United States)

    Yurttaş, Leyla; Tay, Funda; Demirayak, Şeref

    2015-06-01

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

  11. Synthesis and evaluation of 18F-fluoroethylated benzothiazole derivatives for in vivo imaging of amyloid plaques in Alzheimer's disease.

    Science.gov (United States)

    Neumaier, B; Deisenhofer, S; Sommer, C; Solbach, C; Reske, S N; Mottaghy, F

    2010-06-01

    Amyloid aggregates play a major role in the development of Alzheimer's disease. Targeting these aggregates by PET probes enables non-invasively the detection and quantification of amyloid deposit distribution in human brains. Based on benzothiazole core structure a series of amyloid imaging agents were developed. Currently [(11)C]2-(4'-(methylamino)phenyl)-6-hydroxybenzothiazole (Pittsburgh Compound-B (PIB) is the most specific and widely used amyloid imaging ligand. But due to the short half life of (11)C, longer lived (18)F-labeled derivatives offer logistic advantages and higher contrast images. In this work, three different [(18)F]fluoroethoxy-substituted benzothiazole derivatives ([(18)F]2-(4'-(methylamino)phenyl)-6-(2-fluoroethoxy)benzothiazole, [(18)F]2-((2'-(2-fluoroethoxy)-4'-amino)phenyl)benzothiazole and [(18)F]2-(3'-((2-fluoroethoxy)-4'-amino)phenyl)benzothiazole) were synthesized via [(18)F]fluoroethylation. The latter two derivatives with fluoroethoxy-substitution on the aromatic amino group showed very low binding affinity for amyloid aggregates. In contrast [(18)F]2-(4'-(methylamino)phenyl)-6-(2-fluoroethoxy)benzothiazole with [(18)F]fluoroethoxy-substitution in 6-position showed excellent amyloid imaging properties with respect to lipophilicity, brain entry and brain clearance in normal SCID mice, amyloid plaque binding affinity and specificity.

  12. Discovery of benzothiazole guanidines as novel inhibitors of thrombin and trypsin IV.

    Science.gov (United States)

    Karle, Michael; Knecht, Wolfgang; Xue, Yafeng

    2012-07-15

    In a project to find novel neutral P1 fragments for the synthesis of thrombin inhibitors with improved pharmacokinetic properties, fragments containing a benzothiazole guanidine scaffold were identified as weak thrombin inhibitors. WaterLOGSY (Water-Ligand Observed via Gradient SpectroscopY) NMR was used to detect fragments binding to thrombin and these fragments were followed up by Biacore A100 affinity measurements and enzyme assays. A crystal structure of the most potent compound with thrombin was obtained and revealed an unexpected binding mode as well as the key interactions of the fragment with the protein. Based on these results, the structure-based design and synthesis of a small series of optimized novel substituted benzothiazole guanidines with comparatively low pK(a) values was accomplished. Testing of these compounds against human trypsin I and human trypsin IV revealed unexpected inhibitory activity and selectivity of some of the compounds, making them attractive starting points for selective trypsin inhibitors.

  13. Synthesis, characterization and carbonic anhydrase inhibitory activity of novel benzothiazole derivatives.

    Science.gov (United States)

    Küçükbay, F Zehra; Buğday, Nesrin; Küçükbay, Hasan; Tanc, Muhammet; Supuran, Claudiu T

    2016-12-01

    N-protected amino acids were reacted with substituted benzothiazoles to give the corresponding N-protected amino acid-benzothiazole conjugates (60-89%). Their structures were confirmed by proton nuclear magnetic resonance ((1)H NMR), carbon-13 nuclear magnetic resonance ((13)C NMR), IR and elemental analysis. Their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activities were determined against two cytosolic human isoforms (hCA I and hCA II), one membrane-associated (hCA IV) and one transmembrane (hCA XII) enzyme by a stopped-flow CO2 hydrase assay method. The new compounds showed rather weak, micromolar inhibitory activity against most of these enzymes.

  14. Structural and spectral comparisons between isomeric benzisothiazole and benzothiazole based aromatic heterocyclic dyes

    Science.gov (United States)

    Wang, Yin-Ge; Wang, Yue-Hua; Tao, Tao; Qian, Hui-Fen; Huang, Wei

    2015-09-01

    A pair of isomeric heterocyclic compounds, namely 3-amino-5-nitro-[2,1]-benzisothiazole and 2-amino-6-nitrobenzothiazole, are used as the diazonium components to couple with two N-substituted 4-aminobenzene derivatives. As a result, two pairs of isomeric aromatic heterocyclic azo dyes have been produced and they are structurally and spectrally characterized and compared including single-crystal structures, electronic spectra, solvatochromism and reversible acid-base discoloration, thermal stability and theoretically calculations. It is concluded that both benzisothiazole and benzothiazole based dyes show planar molecular structures and offset π-π stacking interactions, solvatochromism and reversible acid-base discoloration. Furthermore, benzisothiazole based aromatic heterocyclic dyes exhibit higher thermal stability, larger solvatochromic effects and maximum absorption wavelengths than corresponding benzothiazole based ones, which can be explained successfully by the differences of their calculated isomerization energy, dipole moment and molecular band gaps.

  15. Synthesis and anticancer activity evaluation of some benzothiazole-piperazine derivatives.

    Science.gov (United States)

    Gurdal, Enise Ece; Buclulgan, Ebru; Durmaz, Irem; Cetin-Atalay, Rengul; Yarim, Mine

    2015-01-01

    Synthesis, characterization and cytotoxic activities of ten benzothiazole-piperazine derivatives were reported. In vitro cytotoxic activities of compounds were screened against hepatocellular (HUH-7), breast (MCF-7) and colorectal (HCT-116) cancer cell lines by sulphorhodamine B assay. Based on the GI50 values of the compounds, most of the benzothiazole-piperazine derivatives are active against HUH-7, MCF-7 and HCT-116 cancer cell lines. Aroyl substituted compounds 1h and 1j were found to be the most active derivatives. In addition, further investigation of compounds 1h and 1j by Hoechst staining and FACS revealed that these compounds cause apoptosis by cell cycle arrest at subG1 phase.

  16. Synthesis and antimicrobial activity of novel structural hybrids of benzofuroxan and benzothiazole derivatives.

    Science.gov (United States)

    Chugunova, Elena; Boga, Carla; Sazykin, Ivan; Cino, Silvia; Micheletti, Gabriele; Mazzanti, Andrea; Sazykina, Marina; Burilov, Alexander; Khmelevtsova, Ludmila; Kostina, Natalia

    2015-03-26

    New compounds containing both benzofuroxan and benzothiazole scaffolds were synthesized through electrophile/nucleophile combination of nitrobenzofuroxan derivatives and 2-mercapto- or 2-aminobenzothiazole derivatives and their biological effect on the natural strain Vibrio genus and different bacterial lux-biosensors was studied. Among all the compounds synthesized, that obtained from 2-mercaptobenzothiazole and 7-chloro-4,6-dinitrobenzofuroxan was toxic for bacterial cells, and also able to activated the 1st type Quorum Sensing system. The reaction between 7-chloro-4,6-dinitrobenzofuroxan and 2-aminobenzothiazole derivatives gave two products, one bearing the benzofuroxan moiety linked to the exocyclic amino nitrogen, and the second derived from the attack of two molecules of electrophile to both the nitrogen atoms of the benzothiazole reagent. Their relative ratio is modifiable by tuning the reagents ratio and the reaction time.

  17. A benzothiazole-based fluorescent probe for distinguishing and bioimaging of Hg(2+) and Cu(2).

    Science.gov (United States)

    Gu, Biao; Huang, Liyan; Su, Wei; Duan, Xiaoli; Li, Haitao; Yao, Shouzhuo

    2017-02-15

    A new benzothiazole-based fluorescent probe 2-(benzo[d]thiazol-2-yl)-4-(1,3- dithian-2-yl)phenol (BT) with two different reaction sites, a thioacetal group (site 1 for Hg(2+)), and O and N atoms of the benzothiazole dye (site 2 for Cu(2+)), was designed and synthesized. The probe BT showed ratiometric fluorescent response to Hg(2+) and fluorescence quenching behavior to Cu(2+), which induces naked-eye fluorescent color changes from green to blue and colorless, respectively. Moreover, it displayed highly sensitivity and selectivity toward Hg(2+) and Cu(2+) without interference from other metal ions. The sensing mechanisms were also confirmed by (1)H NMR titration, mass spectrum and Job's plot analyses. Finally, probe BT was successfully used for fluorescent imaging of Hg(2+) and Cu(2+) in living cells, demonstrating its potential applications in biological science.

  18. Synthesis and Biological Evaluation of Novel Benzothiazole-2-thiol Derivatives as Potential Anticancer Agents

    Directory of Open Access Journals (Sweden)

    Luo-Ting Yu

    2012-03-01

    Full Text Available A series of novel benzothiazole-2-thiol derivatives were synthesized and their structures determined by 1H-NMR, 13C-NMR and HRMS (ESI. The effects of all compounds on a panel of different types of human cancer cell lines were investigated. Among them, pyridinyl-2-amine linked benzothiazole-2-thiol compounds 7d, 7e, 7f and 7i exhibited potent and broad-spectrum inhibitory activities. Compound 7e displayed the most potent anticancer activity on SKRB-3 (IC50 = 1.2 nM, SW620 (IC50 = 4.3 nM, A549 (IC50 = 44 nM and HepG2 (IC50 = 48 nM and was found to induce apoptosis in HepG2 cancer cells.

  19. Benzothiazole-containing hydroxamic acids as histone deacetylase inhibitors and antitumor agents.

    Science.gov (United States)

    Oanh, Dao Thi Kim; Hai, Hoang Van; Park, Sang Ho; Kim, Hyun-Jung; Han, Byung-Woo; Kim, Hyung-Sook; Hong, Jin-Tae; Han, Sang-Bae; Hue, Van Thi My; Nam, Nguyen-Hai

    2011-12-15

    Data from clinical studies indicate that inhibitors of Class I and Class II histone deacetylase (HDAC) enzymes show great promise for the treatment of cancer. Zolinza (SAHA, Zolinza) was recently approved by the FDA for the treatment of the cutaneous manifestations of cutaneous T-cell lymphoma. As a part of our ongoing effort to identify novel small molecules to target these important enzymes, we have prepared two series of benzothiazole-containing analogues of SAHA. It was found that several compounds with 6C-bridge linking benzothiazole moiety and hydroxamic functional groups showed good inhibition against HDAC3 and 4 at as low as 1 μg/ml and exhibited potent cytotoxicity against five cancer cell lines with average IC(50) values of as low as 0.81 μg/ml, almost equipotent to SAHA.

  20. 3-[2-(1,3-Benzothiazol-2-ylsulfanylethyl]-1,3-oxazolidin-2-one

    Directory of Open Access Journals (Sweden)

    Yong-Hong Wen

    2010-10-01

    Full Text Available The title compound, C12H12N2S2O2, consists of a benzothiazole group and a oxazolidin-1-one linked via a flexible ethane-1,2-diyl spacer. The benzothiazole group and the oxazolidine ring are each almost planar [with maximum deviations of 0.007 (2 and 0.044 (3 Å, respectively] and make a dihedral angle of 9.35 (10°. In the crystal structure, adjacent molecules were connected through C—H...O and C—H...N hydrogen bonds, and further extended into a three-dimensional network structure through intermolecular aromatic π–π stacking interactions in which the centroid–centroid distance is 3.590 (1 Å.

  1. 1-(1,3-Benzothiazol-2-yl-3-(4-chlorobenzoylthiourea

    Directory of Open Access Journals (Sweden)

    M. Sukeri M. Yusof

    2009-10-01

    Full Text Available The title compound, C15H10ClN3OS2, adopts a cis–trans configuration across the thiourea C—N bonds with respect to the positions of the benzothiazole and 4-chlorobenzoyl groups relative to thiono S atom. An intramolecular N—H...O hydrogen bond is present. In the crystal structure, molecules are linked by a weak intermolecular N—H...S hydrogen bond, forming centrosymmetric dimers.

  2. Mefenacet [2-(1,3-benzothiazol-2-yloxy-N-methyl-N-phenylacetamide

    Directory of Open Access Journals (Sweden)

    Jineun Kim

    2010-12-01

    Full Text Available The title compound, C16H14N2O2S, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the plane of the benzothiazole ring system and the phenyl ring plane are 51.63 (7 and 60.46 (5°. In the crystal structure, weak intermolecular C—H...O hydrogen bonds and C—H...π interactions contribute to the stabilization of the packing.

  3. 1,2-Bis{2-[(1,3-benzothiazol-2-ylsulfanylmethyl]phenoxy}ethane

    Directory of Open Access Journals (Sweden)

    Liang-Wei Zhang

    2010-09-01

    Full Text Available The molecule of the title compound, C30H24N2O2S4, adopts a Z-shaped conformation. The terminal benzothiazole ring systems are oriented at a dihedral angle of 60.81 (8°, while the central benzene rings are twisted to each other by a dihedral angle of 13.56 (14°. Weak intermolecular C—H...π interactions are present in the crystal structure.

  4. 5-Chloro-2-(3,4,5-trimethoxyphenyl-1,3-benzothiazole

    Directory of Open Access Journals (Sweden)

    Sammer Yousuf

    2012-10-01

    Full Text Available In the title compound, C16H14ClNO3S, the dihedral angle between the almost-planar benzothiazole ring system [maximum deviation = 0.012 (3 Å] and the aromatic ring of the trimethoxyphenyl group is 15.56 (6°. In the crystal, the molecules are arranged into layers parallel to the bc plane, held together only by weak van der Waals forces.

  5. 2-Amino-6-nitro-1,3-benzothiazol-3-ium hydrogen sulfate

    Directory of Open Access Journals (Sweden)

    Hui-Fen Qian

    2011-08-01

    Full Text Available In the title molecular salt, C7H6N3O2S+·HSO4−, the 2-amino-6-nitro-1,3-benzothiazole ring system is essentially planar [mean deviation = 0.0605 (4 Å]. In the crystal, N—H...O and O—H...O hydrogen-bonding interactions result in a layer motif.

  6. Substituted benzothiazoles and therapeutic uses thereof for the treatment of human diseases

    OpenAIRE

    Martínez, Ana; Pérez Fernández, Daniel Ignacio; Gil Ayuso-Gontán, Carmen; García Salado, Irene; Redondo, Miriam; Pérez, Concepción

    2013-01-01

    [EN] The invention relates to a family of differently substituted benzothiazoles having an inhibitory activity against the enzyme casein kinase 1 (CK1), as a result of which they are suitable for use in the treatment or prevention of diseases caused by this enzyme, particularly diseases associated with circadian rhythm and inflammatory, autoimmune, psychiatric, neurodegenerative, neurological or ophthalmological diseases, as well as for inducing cell regeneration.

  7. Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by cetyltrimethyl ammonium bromide (CTAB) in water

    OpenAIRE

    Yang, Xiao-Liang; Xu, Chun-Mei; Lin,Shao-Miao; Chen,Jiu-Xi; Ding,Jin-Chang; Wu,Hua-Yue; Su,Wei-Ke

    2010-01-01

    A series of 2-substituted benzothiazoles have been synthesized by the condensation of 2-aminothiophenol with aldehydes (RCHO: R = Alkyl, Aryl, Heteroaryl, 2-Arylformyl) in the presence of a catalytic amount of cetyltrimethyl ammonium bromide (CTAB) "on water" by a one-pot procedure without additional organic solvents and oxidants. Thereinto, 2-alkylbenzothiazoles were synthesized in high yields and 2-arylformylbenzothiazoles were obtained from the condensation of 2-aminothiophenol with arylfo...

  8. 2-{[4-(1,3-Benzothiazol-2-ylphenyl](methylamino}acetic acid

    Directory of Open Access Journals (Sweden)

    Yong Zhang

    2009-11-01

    Full Text Available In the title compound, C16H14N2O2S, the dihedral angle between the benzothiazole ring system and benzene ring is 3.11 (2°. In the crystal structure, intermolecular O—H...N hydrogen bonds link molecules into chains along [100] and these chains are, in turn, linked into a three-dimensional network via weak intermolecular C—H...O hydrogen bonds.

  9. Oxidation of Refractory Benzothiazoles with PMS/CuFe2O4: Kinetics and Transformation Intermediates

    KAUST Repository

    Zhang, Tao

    2016-05-04

    Benzothiazole (BTH) and its derivatives, 2-(methylthio)bezothiazole (MTBT), 2-benzothiazolsulfonate (BTSA) and 2-hydroxybenzothiazole (OHBT), are refractory pollutants ubiquitously existing in urban runoff at relatively high concentrations. Here, we report their oxidation by CuFe2O4-activated peroxomonosulfate (PMS/CuFe2O4), focusing on kinetics and transformation intermediates. These benzothiazoles can be efficiently degraded by this oxidation process which is confirmed to generate mainly sulfate radicals (with negligible hydroxyl-radical formation) under slightly acidic to neutral pH conditions. The molar exposure ratio of sulfate radical to residual PMS (i.e. Rct) of this process is a constant which is related to reaction condition and can be easily determined. Reaction rate constants of these benzothiazoles towards sulfate radical are (3.3 ± 0.3) × 109, (1.4 ± 0.3) × 109, (1.5 ± 0.1) × 109 and (4.7 ± 0.5) × 109 M-1s-1, respectively (pH 7 and 20 oC). Based on Rct and these rate constants, their degradation in the presence of organic matter can be well predicted. A number of transformation products were detected and tentatively identified using triple-quadruple/linear ion trap MS/MS and high-resolution MS. It appears that sulfate radicals attack BTH, MTBT and BTSA on their benzo ring via electron transfer, generating multiple hydroxylated intermediates which are reactive towards common oxidants. For OHBT oxidation, it prefers to break down the thiazole ring. Due to competitions of the transformation intermediates, a minimum PMS/pollutant molar ratio of 10-20 is required for effective degradation. The flexible PMS/CuFe2O4 could be a useful process to remove the benzothiazoles from low DOC waters like urban runoff or polluted groundwater.

  10. Synthesis, DNA cleavage and antimicrobial activity of 4-thiazolidinones-benzothiazole conjugates.

    Science.gov (United States)

    Singh, Meenakshi; Gangwar, Mayank; Nath, Gopal; Singh, Sushil K

    2014-11-01

    Antimicrobial screening of several novel 4-thiazolidinones with benzothiazole moiety has been performed. These compounds were evaluated for antimicrobial activity against a panel of bacterial and fungal strains. The strains were treated with these benzothiazole derivatives at varying concentrations, and MIC's were calculated. Structures of these compounds have been determined by spectroscopic studies viz., FT-IR, 1H NMR, 13C NMR and elemental analysis. Significant antimicrobial activity was observed for some members of the series, and compounds viz. 3-(4-(benzo[d]thiazol-2-yl) phenyl-2-(4-methoxyphenyl)thiazolidin-4-one and 3-(4-(benzo[d]thiazol-2-yl)phenyl)-2-(4-hydroxy phenyl)thiazolidin-4-one were found to be the most active against E.coli and C. albicans with MIC values in the range of 15.6-125 microg/ml. Preliminary study of the structure-activity relationship revealed that electron donating groups associated with thiazolidine bearing benzothiazole rings had a great effect on the antimicrobial activity of these compounds and contributes positively for the action. DNA cleavage experiments gave valuable hints with supporting evidence for describing the mechanism of action and hence showed a good correlation between their calculated MIC's and its lethality.

  11. Spectral study, stability and protein labeling of two Carbazole–Benzothiazole derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Yu, Lu; Li, Ling; Fei, Xuening, E-mail: xueningfei888@163.com

    2014-05-01

    3-benzothiazole-9-ethyl-carbazole (BEC) and 3,6-di-benzothiazole-9-ethyl-carbazole (DBEC) were synthesized by using carbazole as base and then characterized by {sup 1}H NMR. The optical properties of them were investigated and compared with carbazole and 9-ethyl-carbazole. The photostability and thermostability of the compounds were studied and the results indicated they are both very stable. Effects of solvent properties including polarity, viscosity and refractive index on the spectra properties of the compounds were investigated. Quantum yield of the compounds in organic solvent was also determined and it is found the most complex compound has the highest quantum yield up to 0.68. Finally the synthesized compounds were used to label bovine serum albumin (BSA) protein and simultaneously stability constant (K{sub s}) between them is calculated and compared with other similar dyes. The results showed that the fluorescent intensity of the compound is increased significantly after labeling with BSA protein. - Highlights: • Synthesis and optical properties of two carbazole-benzothiazole derivatives. • Photostability and thermostability of the compounds and compared the results with each other. • Quantum yields of the compounds and the relationship with the structure. • Protein labeling properties of the compounds and stability constant.

  12. [Synthesis and antitumor activity of 5-substituted-2-(pyridyl)benzothiazole compounds].

    Science.gov (United States)

    Liu, Wen-Hu; Chang, Jin-Xia; Liu, Yi

    2013-01-01

    Fifteen novel 5-substituted-2-(pyridyl)benzothiazole compounds were designed and synthesized by simple hydrolization and condensation reaction of the 2-amino-5-substituent benzothiazole. Activities of these synthesized compounds were evaluated on Bcap-37, HCT-15 and HepG2 tumor cells in vitro by standard MTT assay. 5-Fluorouracil (5-FU) was used as the positive control. The results revealed that most of the new compounds had potent effects on Bcap-37, HCT-15 and HepG2 tumor cells, and had no or less effect on 293T and L02 normal cells. Particularly, compounds 1c and 2e exhibited better activities on HCT-15 and HepG2 cells with IC50 values of 41.59 and 38.65 micromol x L(-1), and 1i showed excellent activities on Bcap-37 and HepG2 cells with IC50 values of 46.63 and 23.51 micromol x L(-1), respectively. The structure-activity relationship of 5-substituted-2-(pyridyl)benzothiazole compounds were also discussed preliminarily.

  13. Selective Targeting of G-Quadruplex Structures by a Benzothiazole-Based Binding Motif.

    Science.gov (United States)

    Buchholz, Ina; Karg, Beatrice; Dickerhoff, Jonathan; Sievers-Engler, Adrian; Lämmerhofer, Michael; Weisz, Klaus

    2017-03-09

    A benzothiazole derivative was identified as potent ligand for DNA G-quadruplex structures. Fluorescence titrations revealed selective binding to quadruplexes of different topologies including parallel, antiparallel and (3+1) hybrid structures. The parallel c-MYC sequence was found to constitute the preferred target with dissociation constants in the micromolar range. Binding of the benzothiazole-based ligand to c-MYC was structurally and thermodynamically characterized in detail by employing a comprehensive set of spectroscopic and calorimetric techniques. Job plot analyses and mass spectral data indicate non-cooperative ligand binding to form 1:1 and 2:1 complex stoichiometries. Whereas stacking interactions are suggested by optical methods, NMR chemical shift perturbations also indicate significant rearrangements of both 5'- and 3'-flanking sequences upon ligand binding. Additional isothermal calorimetry studies yield a thermodynamic profile of the ligand-quadruplex association and reveal enthalpic contributions to be the major driving force for binding. The structural and thermodynamic information obtained in the present work provides the basis for the rational development of benzothiazole derivatives as promising quadruplex binding agents.

  14. Preparation, thermo-optic property and simulation of optical switch based on azo benzothiazole polymer

    Science.gov (United States)

    Cao, Zhijuan; Qiu, Fengxian; Wang, Qing; Cao, Guorong; Guan, Yijun; Zhuang, Lin; Xu, Xiaolong; Wang, Jie; Chen, Qian; Yang, Dongya

    2013-04-01

    An azo chromophore molecule 4-[(benzothiazole-2-yl)diazenyl]phenyl-1,3-diamine (BTPD) was prepared with 2-amino benzothiazole and m-phenylenediamine by diazo-coupling reaction. Then, the chromophore molecule BTPD was polymerized with NJ-210 and isophorone diisocyanate (IPDI) to obtain novel azo benzothiazole polymer (BTPU). The structures of BTPD and BTPU were characterized using the Fourier transform infrared, UV-visible spectroscopy, DSC and TGA. The physical properties of the obtained BTPU were investigated. The refractive index ( n) of BTPU was demonstrated at different temperature and wavelength (532, 650 and 850 nm) using attenuated total reflection technique. The transmission loss and dispersion characteristic of BTPU film were investigated using the CCD digital imaging devices and Sellmeyer equation. A Y-branch and 2 × 2 Mach-Zehnder interferometer (MZI) polymeric thermo-optic switches based on the thermo-optic effect of prepared BTPU were proposed and the performance of switches was simulated. The results indicated that the power consumption of the Y-branch thermo-optic switch could be only 0.6 mW. The Y-branch and MZI switching rising and falling times obtained were 8.0 and 1.8 ms.

  15. Benzothiazole Amphiphiles Ameliorate Amyloid β-Related Cell Toxicity and Oxidative Stress.

    Science.gov (United States)

    Cifelli, Jessica L; Chung, Tim S; Liu, Haiyan; Prangkio, Panchika; Mayer, Michael; Yang, Jerry

    2016-06-15

    Oxidative stress from the increase of reactive oxygen species in cells is a common part of the normal aging process and is accelerated in patients with Alzheimer's disease (AD). Herein, we report the evaluation of three benzothiazole amphiphiles (BAMs) that exhibit improved biocompatibility without loss of biological activity against amyloid-β induced cell damage compared to a previously reported hexa(ethylene glycol) derivative of benzothiazole aniline (BTA-EG6). The reduced toxicity of these BAM agents compared to BTA-EG6 corresponded with their reduced propensity to induce membrane lysis. In addition, all of the new BAMs were capable of protecting differentiated SH-SY5Y neuroblastoma cells from toxicity and concomitant oxidative stress induced by AD-related aggregated Aβ (1-42) peptides. Binding and microscopy studies support that these BAM agents target Aβ and inhibit the interactions of catalase with Aβ in cells, which, in turn, can account for an observed inhibition of Aβ-induced increases in hydrogen peroxide in cells treated with these compounds. These results support that this family of benzothiazole amphiphiles may have therapeutic potential for treating cellular damage associated with AD and other Aβ-related neurologic diseases.

  16. SYNTHESIS, CHARACTERIZATION AND BIOCIDAL ACTIVITY OF NOVEL HALOGENATED - 4-[(SUBSTITUTED-BENZOTHIAZOL-2-YL HYDRAZONO]-2-(SUBSTITUTED-PHENYL-5-METHYL /ETHOXY -2,4-DIHYDRO-PYRAZOL-3-ONE DERIVATIVES Synthese, Charakterisierung und biozide Aktivität NOVEL HALOGENIERTEN - 4 - [(substituiertes-benzothiazol-2-YL hydrazono] -2 -(Substituiertes Phenyl-5-Methyl / ETHOXY -2,4-DIHYDRO-pyrazol-3-ONE DERIVATE

    Directory of Open Access Journals (Sweden)

    V. Khatri, K. Sharma, V. Sareen, D. Shinde and S. Sareen

    2012-04-01

    Full Text Available Some new 4-[(substituted-benzothiazol-2-ylhydrazono]-2-(substituted-phenyl-5- methyl/ethoxy-2,4-dihydro-pyrazol-3-one(4 have been synthesized by reacting substituted 2- amino benzothiazol (1 with acetoacetic ester and malonic ester (2. 2-[(substituted-benzothiazol- 2-ylhydrazono]-3-oxo-butyric acid ethyl ester and 2-[(substituted-benzothiazol-2- ylhydrazono]- malonic acid diethyl ester (3 react with different hydrazines to give the title compounds(4. These compounds are evaluated for their antifungal and insecticidal activity. The structures of all these compounds have been confirmed by IR, 1H NMR, mass spectra and elemental analysis data.

  17. Tautomeric conversion, vibrational spectra, and density functional studies on peripheral sulfur derivatives of benzothiazole and benzothiazoline isomers

    Science.gov (United States)

    Altun, Ahmet; Kuliyev, Eziz; Aghatabay, Naz M.

    2016-01-01

    The room temperature structural (tautomerism, dimerization, conformational preference, geometry parameters) and vibrational spectral (IR and Raman) analyses have been performed on benzothiazoline (benzothiazoline-2-thione, 3-methyl-benzothiazoline-2-thione) and benzothiazole [2-mercaptobenzothiazole, 2-methylthiobenzothiazole, and bis(benzothiazole-2-ylthio)ethane] derivatives at the B3LYP/6-311++G∗∗ level of theory. Although the keto to enol transition barriers are too high over the most stable benzothiazoline isomers, vibrational spectral analyses reveal some major bands of benzothiazole isomers in the present room temperature experimental FT-IR and FT-Raman specta. Therefore, benzothiazole isomers exist at rare amounts in the powdered samples that are mainly composed of benzothiazoline isomers. The benzothiazole isomers have two stable conformations due to the orientation of their SH and SCH3 moieties. The energetic and vibrational spectral analyses suggest that the benzothiazoline-2-thione molecules can be stabilized further through the NH⋯S intermolecular hydrogen bonds in solid phase. All observed fundamental vibrational bands of the molecules have been assigned based on the calculated mode frequencies and IR/Raman intensities. The mode assignments have been expressed in terms of internal coordinates and their percent potential energy distributions. The effects of substitution at the nitrogen and peripheral sulfur atoms have been analyzed for the geometries and vibrational bands of the molecules.

  18. EGFR tyrosine kinase targeted compounds: in vitro antitumor activity and molecular modeling studies of new benzothiazole and pyrimido[2,1-b]benzothiazole derivatives.

    Science.gov (United States)

    Gabr, Moustafa T; El-Gohary, Nadia S; El-Bendary, Eman R; El-Kerdawy, Mohamed M

    2014-01-01

    In this study, we illustrate computer aided drug design of new benzothiazole and pyrimido[2,1-b]benzothiazole derivatives as epidermal growth factor receptor tyrosine kinase (EGFR-TK) inhibitors. Compounds 1-5 were screened at NCI, USA, for antitumor activity against non-small cell lung cancer (NCI-H522), colon cancer (HCT-116, HCT-15 and HT29) and breast cancer (MDA-MB-468 and MDA-MB-231/ATCC) cell lines in which EGFR is overexpressed in varying levels. Results indicated that these compounds are more potent antitumor agents compared to erlotinib against HT29 and MDA-MB-231/ATCC cell lines. Compound 3 showed GI50 value of 22.3 nM against NCI-H522 cell line, while erlotinib exhibited GI50 value of 1 µM against the same cell line. In addition, these compounds were studied for their EGFR tyrosine kinase inhibitory activity. Virtual screening utilizing molecular modeling and QSAR techniques enabled the understanding of the pharmacophoric requirements for antitumor activity. Docking the designed compounds into the ATP binding site of EGFR-TK domain was done to predict the analogous binding mode of these compounds to the EGFR-TK inhibitors.

  19. Correlation between electronic parameters and corrosion inhibition of benzothiazole derivatives- NMR parameters as important and neglected descriptors

    Science.gov (United States)

    Behzadi, Hadi; Forghani, Ali

    2017-03-01

    The relation between electronic properties and corrosion inhibitive performance of three benzothiazole derivatives 1,3-benzothiazol-2-amine (BTA), 6-methyl-1,3-benzothiazol-2-amine (MBTA) and 2-amino-1,3-benzthiazole-6-thiol (TBTA) has been investigated by density functional theory. The electronic properties including EHOMO, ELUMO and related parameters were calculated at the B3LYP/6-311++G(d,p) level. The chemical shielding CS tensors were introduced as important and neglected descriptors to evaluate inhibitive efficiency of corrosion inhibitors. Nuclear independent chemical shift (NICS) components, as an aromaticity criterion, were also investigated as local descriptor. Polarizability and CS descriptors, as second rank tensors, show the best correlations with inhibition efficiencies of studied inhibitors.

  20. Discovery and in vivo evaluation of alcohol-containing benzothiazoles as potent dual-targeting bacterial DNA supercoiling inhibitors.

    Science.gov (United States)

    Palmer, James T; Axford, Lorraine C; Barker, Stephanie; Bennett, James M; Blair, Michael; Collins, Ian; Davies, David T; Ford, Leigh; Gannon, Carlie T; Lancett, Paul; Logan, Alastair; Lunniss, Christopher J; Morton, Craig J; Offermann, Daniel A; Pitt, Gary R W; Rao, B Narasinga; Singh, Amit K; Shukla, Tarun; Srivastava, Anil; Stokes, Neil R; Thomaides-Brears, Helena B; Yadav, Anju; Haydon, David J

    2014-09-01

    A series of dual-targeting, alcohol-containing benzothiazoles has been identified with superior antibacterial activity and drug-like properties. Early lead benzothiazoles containing carboxylic acid moieties showed efficacy in a well-established in vivo model, but inferior drug-like properties demanded modifications of functionality capable of demonstrating superior efficacy. Eliminating the acid group in favor of hydrophilic alcohol moieties at C(5), as well as incorporating solubilizing groups at the C(7) position of the core ring provided potent, broad-spectrum Gram-positive antibacterial activity, lower protein binding, and markedly improved efficacy in vivo.

  1. Synthesis, physical properties and simulation of thermo-optic switch based on azo benzothiazole heterocyclic polymer

    Science.gov (United States)

    Qiu, Fengxian; Chen, Caihong; Zhou, Qiaolan; Cao, Zhijuan; Cao, Guorong; Guan, Yijun; Yang, Dongya

    2014-05-01

    A chromophore molecule 4-[(benzothiazole-2-yl)diazenyl]phenyl-1,3-diamine (BTPD) was prepared with 2-amino benzothiazole and m-phenylenediamine by diazo-coupling reaction. Then, the BTPD was polymerized with polyether polyol (NJ-220) and isophorone diisocyanate (IPDI) to obtain novel azo benzothiazole polyurethane-urea (BTPUU). The chemical structures of BTPD and BTPUU were characterized by FT-IR and UV-visible spectroscopy. The thermal and mechanical properties of BTPUU film were investigated. The refractive index and transmission loss of BTPUU film were measured at different temperatures and different laser wavelengths (532 nm, 650 nm and 850 nm) by an attenuated total reflection (ATR) technique and CCD digital imaging devices. The thermo-optic coefficients of BTPUU are -4.7086 × 10-4 °C-1 (532 nm), -6.5257 × 10-4 °C-1 (650 nm) and -5.1029 × 10-4 °C-1 (850 nm), respectively. A Y-branch switch and Mach-Zehnder interferometer (MZI) thermo-optic switches based on thermo-optic effect were proposed and the performances of the switches were simulated, respectively. The results show that the power consumption of the Y-branch thermo-optic switch is only 3.28 mW. The response times of Y-branch and MZI switches are 8.0 ms and 2.0 ms, respectively. The results indicate that the prepared BTPUU has high potential for the applications of the Y-branch digital optical switch (DOS), MZI thermo-optic switch, directional coupler (DC) switch and optical modulators.

  2. N-(4,6-Dimethylpyrimidin-2-yl-1,3-benzothiazol-2-amine

    Directory of Open Access Journals (Sweden)

    Shaaban K. Mohamed

    2011-11-01

    Full Text Available In the title compound, C13H12N4S, an amino N atom is connected to a 1,3-benzothiazole fused-ring system and a dimethyl-substituted pyrimidine ring, these components being aligned [interplanar dihedral angle = 1.9 (1°]. The secondary amino N atom forms an intermolecular N—H...N hydrogen bond to an N atom of the fused ring of an adjacent molecule, generating a centrosymmetric cyclic hydrogen-bonded dimer [graph set R22(8].

  3. Ethyl 2-[4-(1,3-benzothiazol-2-ylanilino]acetate

    Directory of Open Access Journals (Sweden)

    Yong Zhang

    2010-08-01

    Full Text Available In the title compound, C17H16N2O2S, the dihedral angle between the benzothiazole ring system and the benzene ring is 1.20 (2°. The substituted amino substituent is in an extended conformation with an N—C—C—O torsion angle of 179.4 (3°. In the crystal structure, pairs of molecules are connected by intermolecular N—H...O and weak C—H...O hydrogen bonds, forming centrosymmetric dimers.

  4. Synthesis and characterization of novel substituted N-benzothiazole-2-yl-acetamides

    Directory of Open Access Journals (Sweden)

    H.C. Sakarya

    2016-11-01

    Full Text Available Schiff base derivatives of benzothiazole 2a–e have been synthesized by reacting with substituted 2-aminobenzothiazole 1a–e and different substituted benzaldehydes 5a–e. The obtained Schiff bases reaction with NaBH4 has afforded the corresponding some novel amines 3a–e. The condensation of amines with chloroacetylchloride leads to novel amide derivatives 4a–e. The structures of the synthesized compounds are characterized by elemental analysis, IR, MS, 1H NMR and 13C NMR.

  5. N-(4-Chloro-1,3-benzothiazol-2-yl-2-(3-methylphenylacetamide monohydrate

    Directory of Open Access Journals (Sweden)

    H. S. Yathirajan

    2011-10-01

    Full Text Available In the title compound, C16H13ClN2OS·H2O, the dihedral angle between the mean planes of the benzothiazole ring system and the methylphenyl ring is 79.3 (6°. The crystal packing features intermolecular O—H...N, O—H...O and N—H...O hydrogen bonds involving the water molecule and weak C—H...O, C—H...Cg and π–π stacking interactions [centroid–centroid distances = 3.8743 (7, 3.7229 (7 and 3.7076 (8 Å].

  6. 2-({[4-(1,3-Benzothiazol-2-ylphenyl]amino}methylphenol

    Directory of Open Access Journals (Sweden)

    Kim Potgieter

    2012-01-01

    Full Text Available In the title compound, C20H16N2OS, the aniline substituent essentially coplanar with the benzothiazole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å. The phenol group is almost perpendicular to the benzothiazolylaniline group, with an interplanar angle of 88.36 (2°. In the crystal, molecules aggregate as centrosymmetric dimers by pairs of O—H...N hydrogen bonds. C—H...O contacts and N—H...π(arene interactions also occur.

  7. {2-[(1,3-Benzothiazol-2-ylmethoxy]-5-bromophenyl}(phenylmethanone

    Directory of Open Access Journals (Sweden)

    K. N. Venugopala

    2013-06-01

    Full Text Available In the title compound, C21H14BrNO2S, the dihedral angle between the planes of the benzothiazole and phenylmethanone groups is 63.4 (2°. In the crystal, pairs of C—H...N hydrogen bonds link the molecules to form inversion dimers, which are further linked by C—H...O interactions into chains along the c axis. C—H...π and π–π interactions [centroid–centroid distance = 3.863 (1 Å] further stabilize the molecular assembly.

  8. 1,1,2,2-Tetrakis(1,3-benzothiazol-2-ylethene chloroform disolvate

    Directory of Open Access Journals (Sweden)

    Tesfamariam K. Hagos

    2010-09-01

    Full Text Available The asymmetric unit of the title solvate, C30H16N4S4·2CHCl3, contains one half-molecule of tetrakis(2-benzothiazolylethene, the complete molecule being generated by inversion symmetry, and one molecule of chloroform. Pairs of the benzothiazole rings attached to the same carbon atom are almost perpendicular to each other, with an angle between planes of 85.74 (4°. In the crystal, weak C—H...N and C—H...Cl interactions generate a three-dimensional network.

  9. 3-Bromo-7-methoxy-2-phenylimidazo[2,1-b][1,3]benzothiazole

    Directory of Open Access Journals (Sweden)

    Alexander S. Bunev

    2013-04-01

    Full Text Available In the title molecule, C16H11BrN2OS, the central imidazo[2,1-b][1,3]benzothiazole tricycle is essentially planar (r.m.s. deviation = 0.021 Å. The terminal phenyl ring is twisted at 36.18 (5° from the mean plane of the tricycle. In the crystal, pairs of eak C—H...O hydrogen bonds link molecules into centrosymmetric dimers, which are further packed into stacks along the a axis.

  10. Structural basis for isoform selectivity in a class of benzothiazole inhibitors of phosphoinositide 3-kinase γ.

    Science.gov (United States)

    Collier, Philip N; Martinez-Botella, Gabriel; Cornebise, Mark; Cottrell, Kevin M; Doran, John D; Griffith, James P; Mahajan, Sudipta; Maltais, François; Moody, Cameron S; Huck, Emilie Porter; Wang, Tiansheng; Aronov, Alex M

    2015-01-08

    Phosphoinositide 3-kinase γ (PI3Kγ) is an attractive target to potentially treat a range of disease states. Herein, we describe the evolution of a reported phenylthiazole pan-PI3K inhibitor into a family of potent and selective benzothiazole inhibitors. Using X-ray crystallography, we discovered that compound 22 occupies a previously unreported hydrophobic binding cleft adjacent to the ATP binding site of PI3Kγ, and achieves its selectivity by exploiting natural sequence differences among PI3K isoforms in this region.

  11. Novel cycloalkylthiophene-imine derivatives bearing benzothiazole scaffold: synthesis, characterization and antiviral activity evaluation.

    Science.gov (United States)

    Ke, Shaoyong; Wei, Yanhong; Yang, Ziwen; Wang, Kaimei; Liang, Ying; Shi, Liqiao

    2013-09-15

    A series of novel cycloalkylthiophene-imine derivatives containing benzothiazole unit were designed, synthesized and evaluated for their anti-viral activities. The bio-evaluation results indicated that some of the target compounds (such as 5g, 5i, 5u) exhibited good to moderate antiviral effect on CVB5, ADV7 and EV71 viruses, however, these compounds did not have inhibition activity against H1N1 virus. Especially, the compounds 4c and 4d also exhibited high antiviral activities, which provide a new and efficient approach to evolve novel multi-functional antiviral agents by rational integration of active pharmacophores.

  12. {2-[(1,3-Benzothiazol-2-ylmethoxy]-5-chlorophenyl}(4-chlorophenylmethanone

    Directory of Open Access Journals (Sweden)

    K. N. Venugopala

    2013-07-01

    Full Text Available In the title compound, C21H13Cl2NO2S, the benzothiazole ring makes dihedral angles of 0.94 (1 and 70.65 (5° with the 4-chlorophenylmethanone unit and the 5-chlorophenyl ring, respectively. The dihedral angle between the 4-chlorophenylmethanone unit and the 5-chlorophenyl ring is 66.20 (5°. The crystal structure consists of dimeric units generated by C—H...N hydrogen bonds, further linked by C—H...O and C—H...π interactions, leading to a three-dimensional network.

  13. Synthesis and mesomorphic evaluation of new calamitic liquid crystals containing benzothiazole core

    Institute of Scientific and Technical Information of China (English)

    Teck Ming Koh; Sie Tiong Ha; Teck Leong Lee; Siew Ling Lee; Guan Yeow Yeap; Hong Cheu Lin; Ramesh T. Subramaniam

    2011-01-01

    The design and synthesis of new calamitic benzothiazole-based liquid crystals, 2- [4-(4-alkyloxybenzoyloxy)-phenyI]ben-zothiazoles are presented. The target compound was characterized using spectroscopic techniques, such as FT-IR, NMR (1H and 13C), microanalysis and EI-MS. The liquid crystalline behaviours of these compounds were thoroughly examined by differential scanning calorimetry and polarizing optical microscope techniques. These materials exhibited enantiotropic nematic phase with high thermal stability (> 168℃). Smectic A phase starts to emerge as monotropic (metastable) phase from C10 member and changes into enantiotropic (stable) phase from C12 and persists up to C16 members.

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

    Science.gov (United States)

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

    2008-01-01

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

  15. Synthesis and herbicidal evaluation of novel benzothiazole derivatives as potential inhibitors of D1 protease.

    Science.gov (United States)

    Huang, Tonghui; Sun, Jie; An, Lin; Zhang, Lixian; Han, Cuiping

    2016-04-01

    D1 protease is a C-terminal processing protease that has been predicted to be an ideal herbicidal target. Three novel series of benzothiazole derivatives were synthesized and evaluated for their herbicidal activities against Brassica napus (rape) and Echinochloa crusgalli (barnyard grass). The preliminary bioassay indicated that most of the synthesized compounds possess promising D1 protease inhibitory activities and considerable herbicidal activities. Molecular docking was performed to position representative compounds into the active site of D1 protease to determine a probable binding model.

  16. Colorimetric and fluorescence detection of G-quadruplex nucleic acids with a coumarin-benzothiazole probe.

    Science.gov (United States)

    Yan, Jin-wu; Tian, Yi-guang; Tan, Jia-heng; Huang, Zhi-shu

    2015-11-01

    A colorimetric and red-emitting fluorescent dual probe for G-quadruplexes was devised with a conjugated coumarin-benzothiazole scaffold. Its significant and distinct changes in both color and fluorescence enable the label-free and visual detection of G-quadruplex structures. In addition, this probe gives a distinct strong emission response to the nucleoli in fixed cells imaging, which might be attributed to the interaction between the probe and rDNA G-quadruplex based on the chromatin immunoprecipitation assay. All these results suggest its promising application prospects in the G-quadruplex research field.

  17. New benzothiazole/thiazole-containing hydroxamic acids as potent histone deacetylase inhibitors and antitumor agents

    DEFF Research Database (Denmark)

    Thanh Tung, Truong; Oanh, Dao Thi Kim; Dung, Phan Thi Phuong;

    2013-01-01

    Results from clinical studies have demonstrated that inhibitors of histone deacetylase (HDAC) enzymes possess promise for the treatment of several types of cancer. Zolinza(®) (widely known as SAHA) has been approved by the FDA for the treatment of T-cell lymphoma. As a continuity of our ongoing...... research to find novel small molecules to target these important enzymes, we synthesized a series of benzothiazole-containing analogues of SAHA and found several compounds with very potent anticancer cytotoxicity. In this study, three more compounds of this type, including N(1)-(6-chlorobenzo[d]thiazol-2...

  18. Synthesis, molecular structures and phase transition studies on benzothiazole-cored Schiff bases with their Cu(II) and Pd(II) complexes: Crystal structure of (E)-6-methoxy-2-(4-octyloxy-2-hydroxybenzylideneamino)benzothiazole

    Science.gov (United States)

    Yeap, Guan-Yeow; Heng, Boon-Teck; Faradiana, Nur; Zulkifly, Raihana; Ito, Masato M.; Tanabe, Makoto; Takeuchi, Daisuke

    2012-03-01

    Two new homologous series of Cu(II) and Pd(II) complexes with benzothiazole-cored Schiff bases have been synthesised with the aim to study the mesomorphic and thermal properties of ligands upon formation of metal complexes. The molecular structure of title compounds were elucidated with the employment of FT-IR, 1D and 2D FT-NMR spectroscopic techniques. Mesomorphic and thermal behaviour of title compounds have been investigated by differential scanning calorimetry and polarising optical microscope. All the ligands are nematogenic but the corresponding Cu(II) and Pd(II) complexes crystallised in ordinary solid. The conformation of 6-methoxy-2-(4-octyloxy-2-hydroxy-benzylideneamino)benzothiazole was determined by single crystal X-ray diffraction analysis of which the title compound favours more stable (E)-6-methoxy-2-(4-octyloxy-2-hydroxybenzylideneamino)benzothiazole. Crystal structure of the title compound also revealed that the bond length of Cdbnd N (1.303 Å) in the benzothiazole rings very close to that in the exocyclic Cdbnd N linkage (1.298 Å).

  19. The Rearrangement of 2-Benzothiazolylthioacetyl Hydrazide in Synthesis of s-Triazolo[3,4-b]benzothiazole-3-thiol

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    The rearrangement reaction of 2-benzothiazolylthioacetyl hydrazide 1 with potassium hydroxide and carbon disulfide in ethanol to produce s-triazolo[3,4-b]benzothiazole-3-thiol 3 was described.3 also can be obtained from 2-benzothiazolylhydazine 2 and the two methods for getting 3 were compared.Mannich reaction of compounds 3 was reported too.

  20. Biodegradation of benzotriazoles and hydroxy-benzothiazole in wastewater by activated sludge and moving bed biofilm reactor systems

    DEFF Research Database (Denmark)

    Mazioti, Aikaterini A.; Stasinakis, Athanasios S.; Pantazi, Ypapanti;

    2015-01-01

    Two laboratory scale fully aerated continuous flow wastewater treatment systems were used to compare the removal of five benzotriazoles and one benzothiazole by suspended and attached growth biomass. The Activated Sludge system was operated under low organic loading conditions. The Moving Bed...

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

    Energy Technology Data Exchange (ETDEWEB)

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

    1984-12-01

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

  2. Heterogeneous catalytic ozonation of benzothiazole aqueous solution promoted by volcanic sand

    Energy Technology Data Exchange (ETDEWEB)

    Valdes, H. [Facultad de Ingenieria, Universidad Catolica de la Santisima Concepcion, Caupolican 491, Concepcion (Chile)], E-mail: hvaldes@ucsc.cl; Murillo, F.A.; Manoli, J.A.; Zaror, C.A. [Departamento de Ingenieria Quimica (F. Ingenieria), Universidad de Concepcion (Chile)

    2008-05-30

    This paper presents experimental results on the catalytic effect of volcanic sands on benzothiazole ozonation. Experiments were assessed at laboratory scale, in a differential circular flow reactor composed of a volcanic sand fixed bed column of 19 cm{sup 3} and a 1 dm{sup 3} storage tank, operated in batch mode at 20 {sup o}C and pH 2-7. Experimental results show that ozone self-decomposition is enhanced by the presence of volcanic sand at all pH. At pH > pH{sub PZC}, the increase in aqueous ozone decay could be related to ozone interaction with strong Lewis acid on metal oxide surface sites of the volcanic sand. Ozone self-decomposition reactions occurring on the volcanic sand are less affected by the presence of radical scavengers. Benzothiazole removal by ozonation is also enhanced by the presence of volcanic sand. Moreover, the inhibitory effect of free radical scavengers is also impaired by volcanic sand, suggesting that strong Lewis acid surface sites play a key role on the reaction mechanism.

  3. Synthesis, photophysical and electrochemical properties of a carbazole dimer-based derivative with benzothiazole units

    Science.gov (United States)

    Shi, He-ping; Dai, Jian-xin; Shi, Li-wen; Xu, Lei; Zhou, Zhao-bin; Zhang, Yan; Zhou, Wen; Dong, Chuan

    A novel A-π-D-π-D-π-A type compound, containing two benzothiazole rings as electron acceptors and two N-ethylcarbazole groups as electron donors, (E)-1,2-bis(3-(benzothiazol-2-yl)-9-ethylcarbazol-6-yl)ethene (BBECE), was synthesized and characterized by elemental analysis, NMR, MS and thermogravimetric analysis. Electrochemical property of compound BBECE was studied by cyclic voltammetry analysis. The absorption and emission spectra of BBECE was experimentally determined in several solvents and simultaneously computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated absorption and emission wavelengths are coincident with the measured data. The lowest-lying absorption spectra can be mainly attributed to intramolecular charge transfer (ICT), and the fluorescence spectra can be mainly described as originating from an excited state with intramolecular charge transfer (ICT) character. The molecular orbitals (HOMO and LUMO), the ionization potential (IP), the electron affinity (EA) and reorganization energy of compound BBECE were also investigated using density functional theory (DFT). The results show that compound BBECE exhibited excellent thermal stability and electrochemical stability as well as high fluorescence quantum yield, indicating its potential applications as an excellent optoelectronic material in optical fields.

  4. N-[(E-Thiophen-2-ylmethylidene]-1,3-benzothiazol-2-amine

    Directory of Open Access Journals (Sweden)

    Irvin N. Booysen

    2012-08-01

    Full Text Available In the title thiophene-derived Schiff base compound, C12H8N2S2, the thiophene ring is slighty rotated from the benzothiazole group mean plane, giving a dihedral angle of 12.87 (6°. The largest displacement of an atom in the molecule from the nine-atom mean plane defined by the non-H atoms of the benzothiazole ring system is 0.572 (1 Å, exhibited by the C atom at the 3-position of the thiophene ring. In the crystal, weak C—H...S hydrogen bonds involving the thiophene group S atom and the 4-position thiophene C—H group of a symmetry-related molecule lead to an infinite one-dimensional chain colinear with the c axis. The structure is further stabilized by π–π interactions; the distance between the thiazole ring centroid and the centroid of an adjacent benzene ring is 3.686 (1 Å. The crystal studied was an inversion twin with the ratio of components 0.73 (3:0.27 (3.

  5. Synthesis and in vivo diuretic activity of some new benzothiazole sulfonamides containing quinoxaline ring system.

    Science.gov (United States)

    Husain, Asif; Madhesia, Diwakar; Rashid, Mohd; Ahmad, Aftab; Khan, Shah Alam

    2016-12-01

    A series of new 6-substituted-N-[3-{2-(substituted phenyl)-ethenyl} quinoxaline-2(1H)-ylidene]-1,3-benzothiazole-2-amine (4a-f) were designed and synthesized by condensing 2-amino-benzothiazole-6-sulfonic acid amide (1) with chalcones of quinoxaline-2-one (3a-f) in a hope to obtain promising and a new class of diuretic agents. Structures of all the newly synthesized compounds were characterized by spectral data and elemental analysis. The pharmacological studies in experimental rats indicates that compound 4c possesses excellent in vivo diuretic activity of 1.13 and appears to be a better diuretic agent than the reference drugs, acetazolamide (1.0) and urea (0.88). Insight of the binding mode of the synthesized compounds (ligand) into the binding sites of carbonic anhydrase enzyme (PDF code: 4KUV) was provided by docking studies, performed with the help of Maestro 9.0 docking software. Further pharmacokinetic and toxicological studies are needed to confirm the safety of compound 4c which emerged as a lead diuretic compound.

  6. Synthesis and in vitro antiproliferative evaluation of some B-norcholesteryl Benzimidazole and Benzothiazole derivatives.

    Science.gov (United States)

    Cui, Jianguo; Qi, Binbin; Gan, Chunfang; Liu, Zhipin; Huang, Hu; Lin, Qifu; Zhao, Dandan; Huang, Yanmin

    2015-04-22

    Taking orostanal (a compound from a Japanese marine sponge, Stelletta hiwasaensis) as a lead compound, some novel B-norcholesteryl benzimidazole and benzothiazole derivatives were synthesized. The antiproliferative activity of the compounds against human cervical carcinoma (HeLa), human lung carcinoma (A549), human liver carcinoma cells (HEPG2) and normal kidney epithelial cells (HEK293T) was assayed. The results revealed that the benzimidazole group was a better substituent than benzothiazole group for increasing the antiproliferative activity of compounds. 2-(3β'-Acetoxy-5β'-hydroxy-6'-B-norcholesteryl)benzimidazole (9b) with the structure of 6-benzimidazole displays the best antiproliferative activity to the cancer cells in all compounds, but is almost inactive to normal kidney epithelial cells (HEK293T). The assay of compound 9b to cancer cell apoptosis by flow cytometry showed that the compound was able to effectively induce cancer cell apoptosis. The research provided a theoretical reference for the exploration of new anti-cancer agents and may be useful for the design of novel chemotherapeutic drugs.

  7. Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules.

    Science.gov (United States)

    Rothweiler, Ulli; Stensen, Wenche; Brandsdal, Bjørn Olav; Isaksson, Johan; Leeson, Frederick Alan; Engh, Richard Alan; Svendsen, John S Mjøen

    2016-11-10

    DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

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

    Science.gov (United States)

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

    2013-07-01

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

  9. Sorption of benzothiazoles onto sandy aquifer material under equilibrium and nonequlibrium conditions

    Directory of Open Access Journals (Sweden)

    Kragulj Marijana M.

    2014-01-01

    Full Text Available In this study, the sorption behaviour of 1,3-benzothiazole (BT and 2-(methylthiobenzothiazole (MTBT was investigated on Danube geosorbent under equilibrium and nonequilibrium conditions. All sorption isotherms fitted well with the Freundlich model (R2=0.932-0.993. The results showed that organic matter of the Danube geosorbent has a higher sorption affinity for the more hydrophobic MTBT compared to BT. However, sorption-desorption experiments showed that MTBT was more easily desorbed than BT molecules, which indicates the importance of absorption relative to adsorption in the overall sorption mechanism of MTBT. In general, molecules of BT and MTBT were more easily desorbed in the lower concentration range, which resulted in an increase in the hysteresis indices with increasing concentrations. Column experiments revealed that retention of the investigated compounds on the aquifer material followed the compound’s hydrophobicity. BT showed a lower retention, in accordance with its lower sorption affinity obtained in the static experiments, while MTBT showed a greater sorption affinity, and thus had a longer retention time on the column. Thus during transport BT represent greater risk for groundwaters than MTBT. These results have increased our understanding of benzothiazoles sorption and desorption process which represent one of the most important factors which influence the behaviour of organic compounds in the environment.

  10. Transition metal-modified polyoxometalates supported on carbon as catalyst in 2-(methylthio)-benzothiazole sulfoxidation

    Indian Academy of Sciences (India)

    Romina A Frenzel; Gustavo P Romanelli; Mirta N Blanco; Luis R Piz

    2015-01-01

    Polyoxometalates with lacunary Keggin structure modified with transition metal ions [PW11O39M(H2O)]5−, where M = Ni2+, Co2+, Cu2+ or Zn2+, were synthesized and supported on activated carbon to obtain the PW11MC catalysts. Using FT-IR and DTA-TGA it was concluded that the [PW11O39M(H2O)]5− species are interacting with the functional groups of the support, and that thermal treatment leads to the loss of the coordinatively bonded water molecules without any noticeable anion degradation. The activity and selectivity of the catalysts in the sulfoxidation reaction of 2-(methylthio)-benzothiazole, an emerging environmental pollutant, were evaluated. The reaction was carried out in acetonitrile as solvent using H2O2 35% p/v as a clean oxidant. The conversion values decreased in the following order: PW11NiC > PW11CuC > PW11CoC > PW11ZnC, with selectivity to sulfoxide higher than 69%. The catalyst could be reused without appreciable loss of the catalytic activity at least three times. The materials were found to be efficient and recyclable catalysts for 2-(methylthio)-benzothiazole sulfoxidation in order to obtain a more biodegradable product than the corresponding substrate.

  11. Benzothiazole, benzotriazole, and their derivates in clothing textiles--a potential source of environmental pollutants and human exposure.

    Science.gov (United States)

    Avagyan, Rozanna; Luongo, Giovanna; Thorsén, Gunnar; Östman, Conny

    2015-04-01

    Textiles play an important role in our daily life, and textile production is one of the oldest industries. In the manufacturing chain from natural and/or synthetic fibers to the final clothing products, the use of many different chemicals is ubiquitous. A lot of research has focused on chemicals in textile wastewater, but the knowledge of the actual content of harmful chemicals in clothes sold on the retail market is limited. In this paper, we have focused on eight benzothiazole and benzotriazole derivatives, compounds rated as high production volume chemicals. Twenty-six clothing samples of various textile materials and colors manufactured in 14 different countries were analyzed in textile clothing using liquid chromatography tandem mass spectrometry. Among the investigated textile products, 11 clothes were for babies, toddlers, and children. Eight of the 11 compounds included in the investigation were detected in the textiles. Benzothiazole was present in 23 of 26 investigated garments in concentrations ranging from 0.45 to 51 μg/g textile. The garment with the highest concentration of benzothiazole contained a total amount of 8.3 mg of the chemical. The third highest concentration of benzothiazole (22 μg/g) was detected in a baby body made from "organic cotton" equipped with the "Nordic Ecolabel" ("Svanenmärkt"). It was also found that concentrations of benzothiazoles in general were much higher than those for benzotriazoles. This study implicates that clothing textiles can be a possible route for human exposure to harmful chemicals by skin contact, as well as being a potential source of environmental pollutants via laundering and release to household wastewater.

  12. Synthesis and evaluation of {sup 18}F-fluoroethylated benzothiazole derivatives for in vivo imaging of amyloid plaques in Alzheimer's disease

    Energy Technology Data Exchange (ETDEWEB)

    Neumaier, B. [Department of Nuclear Medicine, University of Ulm, Ulm (Germany); Max Planck Institute for Neurological Research, Klaus-Joachim-Zuelch Laboratories of the Max Planck Society and the Faculty of Medicine of the University of Cologne, Cologne (Germany)], E-mail: bernd.neumaier@nf.mpg.de; Deisenhofer, S. [Department of Nuclear Medicine, University of Ulm, Ulm (Germany); Sommer, C. [Department of Neuropathology, University of Mainz (Germany); Solbach, C.; Reske, S.N. [Department of Nuclear Medicine, University of Ulm, Ulm (Germany); Mottaghy, F. [Department of Nuclear Medicine, University of Ulm, Ulm (Germany); Department of Nuclear Medicine, RWTH Aachen, Aachen (Germany)

    2010-06-15

    Amyloid aggregates play a major role in the development of Alzheimer's disease. Targeting these aggregates by PET probes enables non-invasively the detection and quantification of amyloid deposit distribution in human brains. Based on benzothiazole core structure a series of amyloid imaging agents were developed. Currently [{sup 11}C]2-(4'-(methylamino)phenyl)-6-hydroxybenzothiazole (Pittsburgh Compound-B (PIB) is the most specific and widely used amyloid imaging ligand. But due to the short half life of {sup 11}C, longer lived {sup 18}F-labeled derivatives offer logistic advantages and higher contrast images. In this work, three different [{sup 18}F]fluoroethoxy-substituted benzothiazole derivatives ([{sup 18}F]2-(4'-(methylamino)phenyl)-6-(2-fluoroethoxy)benzothiazole, [{sup 18}F]2-((2'-(2-fluoroethoxy)-4'-amino)phenyl)benzothiazole and [{sup 18}F]2-(3'-((2-fluoroethoxy)-4'-amino)phenyl)benzothiazole) were synthesized via [{sup 18}F]fluoroethylation. The latter two derivatives with fluoroethoxy-substitution on the aromatic amino group showed very low binding affinity for amyloid aggregates. In contrast [{sup 18}F]2-(4'-(methylamino)phenyl)-6-(2-fluoroethoxy)benzothiazole with [{sup 18}F]fluoroethoxy-substitution in 6-position showed excellent amyloid imaging properties with respect to lipophilicity, brain entry and brain clearance in normal SCID mice, amyloid plaque binding affinity and specificity.

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

    Institute of Scientific and Technical Information of China (English)

    巨修练; 杨诗宏

    2013-01-01

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

  14. Study of y-irradiated benzothiazole-doped polyvinyl chloride by positron annihilation

    Energy Technology Data Exchange (ETDEWEB)

    Misheva, M. [Faculty of Physics, Sofia Univ. (Bulgaria); Djourelov, N. [Inst. of Nuclear Research and Nuclear Energy, Sofia (Bulgaria); Sertova, N.; Petkov, I.; Deligeorgiev, T. [Faculty of Chemistry, Sofia Univ. (Bulgaria)

    2001-07-01

    Poly(vinyl chloride) (PVC) films containing different (0 / 4) weight percentage of 2-aryl substituted benzothiazole (BT) are studied by positron lifetime and Doppler broadening of annihilation line measurements. The effects of gamma-irradiation dose and of BT contents on positron annihilation parameters are studied. The positron lifetimes and intensities depend on irradiation dose only for BT-doped films. The ortho-positronium intensities for pure and doped PVC decrease with dose increasing in a similar way. The influence of doping is significant only at first doping with 0.125 wt% BT and is weak afterwards. Some of the observed changes of the parameters are explained by the protonation of BT and its conversion into [BTH{sup +}.Cl{sup -}] complexes by the interaction with hydrogen chloride - a product of PVC photodegradation. (orig.)

  15. Inhibition of carbonic anhydrase isoforms I, II, IX and XII with secondary sulfonamides incorporating benzothiazole scaffolds.

    Science.gov (United States)

    Petrou, Anthi; Geronikaki, Athina; Terzi, Emine; Guler, Ozen Ozensoy; Tuccinardi, Tiziano; Supuran, Claudiu T

    2016-12-01

    Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the fundamental reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho/physiological conditions. A series of benzothiazole-based sulfonamides were synthesized and tested as possible CA inhibitors. Their inhibitory activity was assessed against the cytosolic human isoforms hCA I and hCA II and the transmembrane hCA IX and hCA XII. Several of the investigated derivatives showed interesting inhibition activity and selectivities for inhibiting hCA IX and hCA XII over the off-target ones hCA I and hCA II. Furthermore, computational procedures were used to investigate the binding mode of this class of compounds, within the active site of hCA IX.

  16. Design of benzothiazole-1,3,4-thiadiazole conjugates: synthesis and anticonvulsant evaluation.

    Science.gov (United States)

    Siddiqui, Nadeem; Ahuja, Priya; Malik, Sachin; Arya, Satish K

    2013-11-01

    Various 2-[(6-substituted-1,3-benzothiazol-2-yl)amino]-N-[5-substituted-phenyl-1,3,4-thiadiazol-2-yl]acetamides were synthesized with a prospective exploration of "lead hopping", using pharmacophoric elements for in vivo anticonvulsant activity. This yielded three potent candidates (5i, 5t, and 5u) in the preliminary screening employing the maximal electroshock seizure (MES) and the subcutaneous pentylenetetrazole (scPTZ) test, showing minimal neurotoxicity. Their quantitative study indicated an increase of nearly 2-10 times for the MES test and 7- to 67-fold for the scPTZ test in the protective index, the keystone in drug discovery for anticonvulsant activity.

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

    Directory of Open Access Journals (Sweden)

    Vikas S. Padalkar

    2016-11-01

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

  18. Emission of white light from 2-(2'-hydroxyphenyl) benzothiazole in polymer electroluminescent devices

    Energy Technology Data Exchange (ETDEWEB)

    Chang, S.M. [Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei, Taiwan (China)]. E-mail: f10914@ntut.edu.tw; Tzeng, Y.J. [Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei, Taiwan (China); Wu, S.Y. [Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei, Taiwan (China); Li, K.Y. [Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei, Taiwan (China); Hsueh, K.L. [Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei, Taiwan (China)

    2005-04-22

    Single-layer polymer devices that emit bright light from dye dispersed in the polymer matrix are fabricated. The active layer consists only of one polymer layer sandwiched between two electrodes-indium tin oxide and Mg:Ag. 2-(2-hydroxyphenyl) benzothiazole (HBT), a UV absorbent, is synthesized and exhibits bright blue-green fluorescence. Bright white emission is observed when the concentration of the dye in poly(N-vinylcarbazole) (PVK) polymer matrix is adjusted appropriately. The single-layered polymer blended electroluminescent (EL) device (ITO/polymer/Mg/Ag) has a relatively low driving voltage of 8 V. The EL spectrum includes three emission peaks at 420, 530 and 600 nm, representing deep blue, green and red light, respectively. The chromaticity coordinates, as specified by the Commission Internationale de l'Eclairage are (0.34, 0.36)

  19. Chiral separation of benzothiazole derivatives of amino acids using capillary zone electrophoresis.

    Science.gov (United States)

    Nováková, Zuzana; Pejchal, Vladimír; Fischer, Jan; Česla, Petr

    2017-02-01

    A method for the separation of enantiomers of leucine and phenylalanine benzothiazole derivatives as potential antimicrobial agents was developed using capillary zone electrophoresis with a dual cyclodextrin (CD) system. The best resolution of enantiomers was achieved in 100 mmol/L phosphate background electrolyte (pH 3.5) with the dual CD system consisting of 10 mmol/L of β-CD with 10 mmol/L of 2-hydroxypropyl-β-cyclodextrin for leucine derivative and 10 mmol/L of 2-hydroxypropyl-γ-cyclodextrin for phenylalanine derivative, respectively. Under the optimal conditions, the highest enantioresolution of 1.25 was achieved in a noncoated-fused silica capillary at 17°C and 24 kV applied voltage.

  20. Benzothiazole-Pyimidine-Based BF2 Complex for Selective Detection of Cysteine.

    Science.gov (United States)

    Liu, Qingsong; Zhang, Changli; Wang, Xiaoqing; Gong, Shuwen; He, Weijiang; Liu, Zhipeng

    2016-01-01

    Due to the similar structure and reactivity of cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), the simultaneous discrimination of Cys over Hcy and GSH by a single fluorescent sensor is still a great challenge. In this work, a benzothiazole-pyimidine-based boron difluoride complex (BPB) was developed as a new fluorescent sensor for Cys. The sensor exhibits a highly selective "turn-on" response to cysteine over Hcy, GSH and other amino acids in aqueous solution at physiological pH. The observed pseudo-first-order rate constant for the reaction of BPB with Cys was calculated to be about 0.062 min(-1) . The detection limit of this sensor for Cys was determined to be 332 nm, and bioimaging of exogenous Cys by this sensor was successfully applied in living cells, thus indicating that this sensor holds great potential for biological applications.

  1. DFT study of conformational and vibrational characteristics of 2-(2-hydroxyphenyl)benzothiazole molecule

    Science.gov (United States)

    Pandey, Urmila; Srivastava, Mayuri; Singh, R. P.; Yadav, R. A.

    2014-08-01

    The conformational and IR and Raman spectral studies of 2-(2-hydroxyphenyl)benzothiazole have been carried out by using the DFT method at the B3LYP/6-311++G** level. The detailed vibrational assignments have been done on the basis of calculated potential energy distributions. Comparative studies of molecular geometries, atomic charges and vibrational fundamentals of all the conformers have been made. There are four possible conformers for this molecule. The optimized geometrical parameters obtained by B3LYP/6-311++G** method showed good agreement with the experimental X-ray data. The atomic polar tensor (APT) charges, Mulliken atomic charges, natural bond orbital (NBO) analysis and HOMO-LUMO energy gap of HBT and its conformers were also computed.

  2. Antiwear and reducing friction performance of (2-sulphurone-benzothiazole)-3-methyl dodecanoate

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    A heterocyclic derivative of (2-sulphurone-benzothiazole)-3-methyl dodecanoate was synthesized. Its tribological performance when added to liquid paraffin was evaluated on a four-ball tester and a ring-on-block machine. Results indicate that compared with the base oil the wear resistance and load-carrying capacities of the oil with novel additive are improved, and the friction coefficient is decreased. There is an optimal content of the novel compound, at which the corresponding oil gives the highest maximum non-seizure load. Above the content, the load carrying capacity of the oil is not increased but decreased. The nature of the film formed on the rubbed surface was investigated by X-ray photoelectron spectroscopy (XPS) analysis, and the action mechanism of the novel compound was discussed.

  3. catena-Poly[lead(II-bis(μ-2-amino-1,3-benzothiazole-6-carboxylato

    Directory of Open Access Journals (Sweden)

    Jun-Dong Wang

    2010-12-01

    Full Text Available The title complex, [Pb(C8H5N2O2S2]n, consists of one PbII ion located on a crystallographic twofold axis and two symmetry-related 2-amino-1,3-benzothiazole-6-carboxylate (ABTC ligands. The central PbII ion has a (4 + 2 coordination by four O atoms of the two ABTC ligands and two weaker Pb—S bonding interactions (Pb—S secondary bonds from S atoms of other two neighbouring ABTC ligands. These bonds link the metal ions into zigzag chains along the c axis, which, in turn, aggregate through π–π interactions [centroid–centroid distance = 3.7436 Å] between ABTC rings and N—H...O and N—H...N hydrogen bonds.

  4. Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers.

    Science.gov (United States)

    Kamal, Ahmed; Ashraf, Md; Vishnu Vardhan, M V P S; Faazil, Shaikh; Nayak, V Lakshma

    2014-01-01

    A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC50 value of 4.01μM. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis.

  5. Clean and Green Synthesis of New Benzothiazole Derivatives via Electrochemical Oxidation of Catechol Derivatives

    Directory of Open Access Journals (Sweden)

    Mansour Arab Chamjangali

    2016-06-01

    Full Text Available Electrochemical oxidation of the catechols 1a and 1b is studied in the presence of 6-methyl-2-thouracil (3b and 6-propyl-2-thiouracil (3a as nucleophiles in a phosphate buffer (0.15 mol L−1, pH = 6.8/DMF (95:5 solution using cyclic voltammetry and controlled-potential coulometry. The results obtained indicate that the quinones derived from the catechols participate in 1,4-Michael-addition reactions with the nucleophiles to form the corresponding new benzothiazole compounds. In this work, we derive a variety of products with good yields using controlled potential at graphite electrodes in an undivided cell. This work is licensed under a Creative Commons Attribution 4.0 International License.

  6. Hybrid benzothiazole analogs as antiurease agent: Synthesis and molecular docking studies.

    Science.gov (United States)

    Taha, Muhammad; Ismail, Nor Hadiani; Imran, Syahrul; Wadood, Abdul; Rahim, Fazal; Khan, Khalid Muhammad; Riaz, Muhammad

    2016-06-01

    Benzothiazole analogs (1-20) have been synthesized, characterized by EI-MS and (1)H NMR, and evaluated for urease inhibition activity. All compounds showed excellent urease inhibitory potential varying from 1.4±0.10 to 34.43±2.10μM when compared with standard thiourea (IC50 19.46±1.20μM). Among the series seventeen (17) analogs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, and 18 showed outstanding urease inhibitory potential. Analogs 15 and 19 also showed good urease inhibition activity. When we compare the activity of N-phenylthiourea 20 with all substituted phenyl derivatives (1-18) we found that compound 15 showed less activity than compound 20 having 3-methoxy substituent. The binding interactions of these active analogs were confirmed through molecular docking.

  7. Synthesis and anticancer evaluation of 2-phenyl thiaolidinone substituted 2-phenyl benzothiazole-6-carboxylic acid derivatives

    Directory of Open Access Journals (Sweden)

    Padmavathi P. Prabhu

    2015-03-01

    Full Text Available A novel series of 2-(3-(4-oxo-2-substituted phenyl thiazolidin-3-ylphenylbenzo[d]thiazole-6-carboxylic acid derivatives PP1–PP8 were synthesized by various benzothiazole Schiff’s bases by reaction with thioglycollic acid. Their structures were established on the basis of IR, 1H-NMR, 13C-NMR, mass spectral data and elemental analysis. All the synthesized compounds were screened for their in vitro anticancer activity by 3-(4,5-dimethyl thiazole-2yl-2,5-diphenyltetrazoliumbromide (MTT assay on human cervical cancer cell line (HeLa cell lines. Among these compound PP2 exhibited most significant activity as compared with PP5, PP7 and PP8. However, the activity was less as compared to the standard drug Cisplatin.

  8. 4-(1,3-Benzothiazol-2-yl-N-(2-pyridylmethylaniline monohydrate

    Directory of Open Access Journals (Sweden)

    Qing-Zhi Wang

    2009-01-01

    Full Text Available In the title compound, C19H15N3S·H2O, the benzothiazole ring system forms a dihedral angle of 7.22 (1° with the benzene ring and the benzene ring forms a dihedral angle of 80.89 (1° with the pyridine ring. An intramolecular N—H...O interaction is present. The crystal structure is stablized by intermolecular O—H...N hydrogen bonds, π–π [centroid–centroid distances = 3.782 (1, 3.946 (1 and 3.913 (1 Å] and C—H...π interactions, forming a three dimensional-network.

  9. [Synthesis and biological evaluation of 2-(3-butynoicamidophenyl) benzothiazole derivatives as antitumor agents].

    Science.gov (United States)

    Yin, Gui-Lin; Li, Yan; Tang, Ke; Jin, Xiao-Feng; Chen, Xiao-Guang; Li, Li; Feng, Zhi-Qiang

    2014-06-01

    A series of 2-(3-butynoicamidophenyl)benzothiazole derivatives were synthesized starting from 4-fluoro-3-nitrobenzoic acid. Structures of all the synthesized compounds were confirmed by 1H NMR and HR-MS. Their antitumor activities against human tumor cells lines (HCT116, Mia-PaCa2, U87-MG, A549, NCI-H1975) were evaluated by MTT assay. The results revealed that most of the synthesized compounds showed potent activities against HCT116, Mia-PaCa2, U87-MG tumor cells lines. Particularly, compounds 14c and 14h exhibited better activity with IC50 values of 1 x 10(-8) mol x L(-1) against U87-MG and HCT116 respectively. The structure-activity relationship of compounds was also discussed preliminarily.

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

    Science.gov (United States)

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

    2013-04-21

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

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

    Science.gov (United States)

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

    2012-08-01

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

  12. 2-(2{prime}-hydroxyphenyl)benzothiazoles, -benzoxazoles, and -benzimidazoles for plastic scintillation applications

    Energy Technology Data Exchange (ETDEWEB)

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

    1995-08-25

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

  13. Benzothiazole incorporated thiazolidin-4-ones and azetidin-2-ones derivatives: Synthesis and in vitro antimicrobial evaluation

    Directory of Open Access Journals (Sweden)

    Sadaf J. Gilani

    2016-11-01

    Full Text Available In this study, a series of novel thiazolidin-4-ones (5a–g and azetidin-2-ones (6a–g were synthesized from N-(6-chlorobenzo[d]thiazol-2-ylhydrazine carboxamide derivatives of the benzothiazole class. Antimicrobial properties of the title compound derivatives were investigated against one Gram (+ bacteria (Staphylococcus aureus, three Gram (− bacteria (Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae and five fungi (Candida albicans, Aspergillus niger, Aspergillus flavus, Monascus purpureus and Penicillium citrinum using serial plate dilution method. The investigation of antibacterial and antifungal screening data revealed that all the tested compounds showed moderate to good inhibition at 12.5–200 μg/mL in DMSO. It has been observed that azetidin-2-ones derivatives are found to be more active than thiazolidin-4-ones derivatives against all pathogenic bacterial and fungal strains.

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

    Institute of Scientific and Technical Information of China (English)

    刘巨艳; 刘倩; 徐玮; 王玮璐

    2011-01-01

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

  15. Nanostructures and Self-Assembly of Organogels via Benzimidazole/Benzothiazole Imide Derivatives with Different Alkyl Substituent Chains

    Directory of Open Access Journals (Sweden)

    Xihai Shen

    2013-01-01

    Full Text Available New benzimidazole/benzothiazole imide derivatives with different alkyl substituent chains were designed and synthesized. Their gelation behaviors in 22 solvents were tested as novel low-molecular-mass organic gelators. The test showed that the alkyl substituent chains and headgroups of benzimidazole/benzothiazole residues in gelators played a crucial role in the gelation behavior of all compounds in various organic solvents. More alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents. SEM and AFM observations revealed that the gelator molecules self-assemble into different aggregates from wrinkle, lamella and belt to dot with change of solvents. Spectral studies indicated that there existed different H-bond formation between imide groups and hydrophobic force of alkyl substituent chains in molecular skeletons. The present work may give some insights into design and character of new organogelators and soft materials with special molecular structures.

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

    Science.gov (United States)

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

    2013-09-01

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

  17. Structure-based design and synthesis of potent benzothiazole inhibitors of interleukin-2 inducible T cell kinase (ITK).

    Science.gov (United States)

    MacKinnon, Colin H; Lau, Kevin; Burch, Jason D; Chen, Yuan; Dines, Jonathon; Ding, Xiao; Eigenbrot, Charles; Heifetz, Alexander; Jaochico, Allan; Johnson, Adam; Kraemer, Joachim; Kruger, Susanne; Krülle, Thomas M; Liimatta, Marya; Ly, Justin; Maghames, Rosemary; Montalbetti, Christian A G N; Ortwine, Daniel F; Pérez-Fuertes, Yolanda; Shia, Steven; Stein, Daniel B; Trani, Giancarlo; Vaidya, Darshan G; Wang, Xiaolu; Bromidge, Steven M; Wu, Lawren C; Pei, Zhonghua

    2013-12-01

    Inhibition of the non-receptor tyrosine kinase ITK, a component of the T-cell receptor signalling cascade, may represent a novel treatment for allergic asthma. Here we report the structure-based optimization of a series of benzothiazole amides that demonstrate sub-nanomolar inhibitory potency against ITK with good cellular activity and kinase selectivity. We also elucidate the binding mode of these inhibitors by solving the X-ray crystal structures of several inhibitor-ITK complexes.

  18. 2-(Nitroaryl)benzothiazole and benzoxazole derivatives as fluorogenic substrates for the detection of nitroreductase activity in clinically important microorganisms.

    Science.gov (United States)

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

    2015-12-15

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

  19. Design, synthesis and biological evaluation of α-substituted isonipecotic acid benzothiazole analogues as potent bacterial type II topoisomerase inhibitors.

    Science.gov (United States)

    Axford, Lorraine C; Agarwal, Piyush K; Anderson, Kelly H; Andrau, Laura N; Atherall, John; Barker, Stephanie; Bennett, James M; Blair, Michael; Collins, Ian; Czaplewski, Lloyd G; Davies, David T; Gannon, Carlie T; Kumar, Dushyant; Lancett, Paul; Logan, Alastair; Lunniss, Christopher J; Mitchell, Dale R; Offermann, Daniel A; Palmer, James T; Palmer, Nicholas; Pitt, Gary R W; Pommier, Stéphanie; Price, Daniel; Narasinga Rao, B; Saxena, Rashmi; Shukla, Tarun; Singh, Amit K; Singh, Mahipal; Srivastava, Anil; Steele, Christopher; Stokes, Neil R; Thomaides-Brears, Helena B; Tyndall, Edward M; Watson, David; Haydon, David J

    2013-12-15

    The discovery and optimisation of a new class of benzothiazole small molecules that inhibit bacterial DNA gyrase and topoisomerase IV are described. Antibacterial properties have been demonstrated by activity against DNA gyrase ATPase and potent activity against Staphylococcus aureus, Enterococcus faecalis, Streptococcus pyogenes and Haemophilus influenzae. Further refinements to the scaffold designed to enhance drug-likeness included analogues bearing an α-substituent to the carboxylic acid group, resulting in excellent solubility and favourable pharmacokinetic properties.

  20. Antiproliferative Activity Evaluation of a Series of N-1,3-Benzothiazol-2-ylbenzamides as Novel Apoptosis Inducers

    Directory of Open Access Journals (Sweden)

    Filomena Corbo

    2016-01-01

    Full Text Available A series of N-1,3-benzothiazol-2-ylbenzamide derivatives were studied for their antiproliferative activity on human liver hepatocellular carcinoma (HepG2 and human breast cancer (MCF-7 cell lines. Most of them were found to show a prominent inhibitory effect on cell growth. Among the most active compounds, 1k emerged for its proapoptotic effect that is particularly evident towards MCF-7 cancer cell lines.

  1. 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.

  2. Benzothiazol-2-amine–3-methoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1/1

    Directory of Open Access Journals (Sweden)

    Jian Li

    2011-01-01

    Full Text Available In the title 1:1 adduct, C7H6N2S·C9H10O5, all non-H atoms of the benzothiazol-2-amine molecule are essentially coplanar, with a maximum deviation of 0.0286 (9 Å for the S atom. In the crystal, intermolecular N—H...O and O—H...N hydrogen bonds connect two molecules of each type into centrosymmetric four-component clusters.

  3. Water and ionic liquid synergy: A novel approach for the synthesis of benzothiazole-2(3H)-one

    OpenAIRE

    Malik A. Waseem; Shireen; Arjita Srivastava; Anjali Srivastava; Rahila; Siddiqui, I. R.

    2015-01-01

    Synergy between water, a green reaction medium and ionic liquid, a green catalyst has opened new vistas in the field of organic transformation. The developed methodology has emerged as an interesting combination for an environmentally benign, facile and efficient synthesis of benzothiazole-2(3H)-one. Product was achieved in excellent yield by the reaction of structurally diverse 2-iodoanilines with potassium thiocyanate. The strategy involves nucleophilic substitution forming NC and SC bond...

  4. Direct Preparation of 2-Benzothiazolylzinc Bromide and its Applications: A Facile Synthetic Route to the Preparation of 2-Substituted Benzothiazole Derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Park, Sooyoul [Korea Research Institute of Chemical Technology, Daejeon (Korea, Republic of); Lee, Kyuhyuk; Kim, Seunghoi [Dankook Univ., Yongin (Korea, Republic of)

    2014-06-15

    We have developed a novel approach for the direct preparation of 2-benzothiazolylzinc bromide and its application in organic synthesis. This protocol is a new tool for the convenient synthesis of 2-substituted benzothiazole derivatives. The resulting products obtained from this work can be utilized for further applications in the synthesis of many biologically active compounds. The benzothiazole moiety has been found in a variety of natural products and pharmaceuticals and demonstrates efficient biological activities. Specifically, 2-substituted benzothiazole derivatives have attracted considerable attention in a wide spectrum of chemical applications due to their unique structural properties. Therefore, the diversity of synthetic protocols has been an extensively discussed topic among scientists involved in organic synthesis for the past decades. In general, to build up the 2-substituted benzothiazole complexes, the strategic tools can be categorized as shown in Scheme 1: cross-coupling of benzothiazolylmetallic complexes (method A), coupling reaction of benzothiazole via direct oxidative C-H activation, cross-coupling of organometallic with halobenzothiazole, and ring-construction of N and S-containing compounds with the appropriate substrates.

  5. Benzothiazole and Perylene Bisimide Derivatives - Synthesis and Opto-Electronic Characterization

    Energy Technology Data Exchange (ETDEWEB)

    Dey, S.

    2012-07-01

    This work investigates the tuning of photophysical properties of two different classes of photoactive molecules, 2-(2'-hydroxyphenyl)benzothiazole (HBT) and perylene bisimide (PBI). The Suzuki coupling reaction was employed to synthesize aryl-substituted derivatives of HBT and PBI. The tuning of the photophysical properties of both HBT and PBI was successfully carried out by attaching either electrondonating (ED) or electron-withdrawing (EW) aryl moieties to the parent compounds. For HBT, a series of 5-substituted derivatives were synthesized to modify the highest occupied molecular orbital (HOMO) energy levels of zinc-benzothiazole (Znb{sub 2}) complexes. Perylene bay substitutions were used to tune the HOMO-LUMO (LUMO: lowest unoccupied molecular orbital) energy gap of the diaryl-PBIs. Spectroscopic and electrochemical techniques were used to determine the effects of substituents on the photophysical properties to the parent compounds. For the Znb{sub 2} complexes, absorption and emission spectra as well as the HOMO energy levels are effectively modified by the aryl-substitution while the LUMO energy level remains largely unaffected. Whereas, for the PBI derivatives, the spectroscopic profiles as well as the HOMO and LUMO energy levels were tuned by the attached aryl groups. These results indicate that inductive effects are more dominant in both Znb{sub 2} and PBI derivatives. All the involved reactions, especially borylation of both the HBT and PBI were studied in detail to achieve maximum yield and simple purification. The separation of a series of 1,7- and 1,6-diaryl-PBIs by normal column chromatography was an important step in perylene chemistry. The individual regioisomers of diaryl-PBIs were unambiguously characterized by observing the chemical shifts of ?- methylene protons using 300 MHz 'H NMR spectroscopy. Obtained results indicate that both 1,7- and 1,6-regioisomers of same diaryl-PBI possess slightly different opto-electronic properties

  6. A novel water-soluble benzothiazole derivative BD926 triggers ROS-mediated B lymphoma cell apoptosis via mitochondrial and endoplasmic reticulum signaling pathways.

    Science.gov (United States)

    Li, Min-Hui; Yang, Ping; Yang, Tai; Zhang, Kun; Liu, Yang; Liu, Jin; Li, Li-Mei; Luo, Xing-Yan; Yang, Shu-Xia; Zou, Qiang; Zhang, Chong-Jie

    2016-11-01

    Benzothiazole derivatives are known for various biological activities, and their potency in cancer therapy have received considerable attention in recent years. However, the poor water solubility of most benzothiazole derivatives has limited their clinical application. We developed BD926, a novel water-soluble benzothiazole derivative and showed here that it could inhibit the proliferation and induce apoptosis of human Ramos B-lymphoma cells. We further showed that BD926 triggered apoptosis through both mitochondria and endoplasmic reticulum pathways. Moreover, BD926 caused cell cycle arrest at G0/G1 stage. Furthermore, accumulation of reactive oxygen species (ROS) were observed after BD926 treatment and ROS inhibitor was able to attenuate BD926-induced apoptosis, which suggested that BD926-induced apoptosis may be due to over-producing ROS. These results demonstrate the anticancer effects of BD926 in cell models and raise the possibility for the application of BD926 in cancer therapy.

  7. Study on the Synthesis and Spectra of a Novel Kind of Carbozole Benzothiazole Indole Styryl Cyanine Dye with a Carbazole Bridged Chain.

    Science.gov (United States)

    Fei, Xuening; Hao, Yachao; Gu, Yingchun; Li, Chao; Yu, Lu

    2014-03-01

    Based on the frequently-used cyanine dye probe thiazole orange (TO) and Cy3, a novel kind of styryl cyanine dye was designed and synthesized. Carbazole was inserted into the structures of two cyanine dyes, TO and Cy3, to act as a bridge to link the benzothiazole and indole. This modification resulted in a novel kind of carbozole benzothiazole indole cyanine dye with a carbazole-bridged chain. The dyes were characterized by HNMR and MS. The spectra of the novel dyes were also studied and the results showed that the fluorescence wavelength of novel carbazole benzothiazole indole cyanine dye shifted red, the Stokes shift and Fluorescence quantum yields increased and the fluorescence intensity was enhanced compared to that of TO. These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.

  8. Determination of benzothiazole and benzotriazole derivates in tire and clothing textile samples by high performance liquid chromatography-electrospray ionization tandem mass spectrometry.

    Science.gov (United States)

    Avagyan, Rozanna; Sadiktsis, Ioannis; Thorsén, Gunnar; Östman, Conny; Westerholm, Roger

    2013-09-13

    A high performance liquid chromatography-tandem mass spectrometry method utilizing electrospray ionization in positive and negative mode has been developed for the separation and detection of benzothiazole and benzotriazole derivates. Ultra-sonication assisted solvent extraction of these compounds has also been developed and the overall method demonstrated on a selected clothing textile and an automobile tire sample. Matrix effects and extraction recoveries, as well as linearity and limits of detection have been evaluated. The calibration curves spanned over more than two orders of magnitude with coefficients of correlation R(2)>0.99 and the limits of detection and the limits of quantification were in the range 1.7-58pg injected and 18-140pg/g, respectively. The extraction recoveries ranged between 69% and 102% and the matrix effects between 75% and 101%. Benzothiazole and benzotriazole derivates were determined in the textile sample and benzothiazole derivatives determined in the tire sample with good analytical performance.

  9. Electrochemical study of FeS corrosion in acid solutions in the presence of benzothiazolic compounds

    Energy Technology Data Exchange (ETDEWEB)

    Chirita, P.; Samide, A.; Ciuciu, A. [Univ Craiova, Fac Chem, Craiova (Romania); Descostes, M.; Schlegel, M.L. [CEA Saclay, DEN, 91 - Gif sur Yvette (France)

    2009-06-15

    Complete text of publication follows: Iron monosulfide (FeS) exposed to acidic solutions containing oxidants can dissolve oxidatively [1, 2]. This corrosion releases toxic elements (heavy metals and arsenic) present in the FeS matrix. However, this corrosion may be altered by interaction with organic molecules. 2-(cyclohexyl-amino-mercapto)-benzothiazole (CMB) and 2-mercapto-benzothiazole (MBT) are known to inhibit corrosion of steel [3]. The present study investigated the effect of these molecules on FeS. The behaviour of synthetic FeS in acid solutions at 25 C in the presence and the absence of CMB or MBT was investigated using electrochemical measurements and microscopic analysis. The corrosion currents (i{sub corr}) were obtained from Tafel polarization plots [3]. The polarization resistance in absence and presence of inhibitors (R{sup 0}{sub p} and R{sub p}, respectively) were determined from electrochemical impedance spectroscopy. It was observed that both CMB and MBT reduce the oxidative (anodic) dissolution of FeS. For example, in 0.1 mol L{sup -1} HCl i{sub corr} decreases from 342 {mu}A cm{sup -2} (in the absence of inhibitors) to 65 {mu}A cm{sup -2} ([CMB] = 5*10{sup -4} mol L{sup -1}) and to 95.8 {mu}A cm{sup -2} ([MBT] = 5*10{sup -4} mol L{sup -1}). Instead R{sub p} increases from 33.4 {Omega} cm{sup 2} in the absence of inhibitors to 175.4 and to 119.3 {Omega} cm{sup 2} in the presence of CMB and MBT, respectively. These results indicate that CMB is a more efficient inhibitor than MBT. It was also found that the FeS surface coverage [{theta} = 1- (R{sup 0}{sub p}/R{sub p})] increases when inhibitor concentration augments from 2*10{sup -4} to 5*10{sup -4} mol L{sup -1}. This is in good agreement with microscopic images that indicate the formation of a protective film on the FeS surfaces corroded in presence of inhibitors. All these findings suggest that FeS corrosion can be substantially reduced by the formation of organic layers that may modify the

  10. FeF(3) catalyzed cascade C-C and C-N bond formation: synthesis of differentially substituted triheterocyclic benzothiazole functionalities under solvent-free condition.

    Science.gov (United States)

    Atar, Amol B; Jeong, Yeon Tae

    2014-05-01

    A series of diverse polyfunctionalized triheterocyclic benzothiazoles were easily prepared in excellent yields via the Biginelli reaction of 2-aminobenzothiazole with substituted benzaldehydes and α-methylene ketones using FeF(3) as an expeditious catalyst under solvent-free conditions. The protocol provides a practical and straightforward approach toward highly functionalized triheterocyclic benzothiazole derivatives in excellent yields. The reaction was conveniently promoted by FeF(3) and the catalyst could be recovered easily after the reaction and reused without any loss of its catalytic activity. The advantageous features of this methodology are high atom economy, operational simplicity, shorter reaction time, convergence, and facile automation.

  11. MICROWAVE ASSISTED SYNTHESIS AND EVALUATION OF SOME FLUORO, CHLORO 2-N (SUBSTITUTED SCHIFF’S BASES AMINO BENZOTHIAZOLES DERIVATIVES FOR THEIR ANTIINFLAMMATORY ACTIVITY

    Directory of Open Access Journals (Sweden)

    Muttu C.T

    2010-12-01

    Full Text Available The present research work is aimed to synthesize a series of various substituted benzothiazole derivatives containing 7-chloro-6-fluoro-N (substituted hydrozones - benzothiazole.Structures of compounds has been established by means of IR, 1H-NMR and elemental analysis. The compounds MIIIc, MIIIf and MIIIJ at dose 5 mg/kg and 10mg/kg body.wt were evaluated for anti-inflammatory activity using carragennan induced paw edema method. The selected compounds have shown significant anti-inflammatory activity as compared to the standard drug. Compound MIIIJ (10 mg/kg body weight has shown more significant result when compared with standard drug.

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

    Science.gov (United States)

    1985-07-01

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

  13. Advanced treatment of benzothiazole contaminated waters: comparison of O3, AC, and O3/AC processes.

    Science.gov (United States)

    Valdés, H; Zaror, C A

    2005-01-01

    Benzothiazole (BT) is a toxic and poorly biodegradable contaminant, usually found in wastewater from rubber related applications. This compound could be effectively eliminated using advanced treatment processes. This paper compares experimental results on detoxification systems based on ozone oxidation, activated carbon adsorption, and simultaneous adsorption-oxidation using ozone in the presence of activated carbon. The effect of pH (2-11), and the presence of radical scavengers (tert-butyl alcohol and sodium carbonate) on process rates and removal efficiencies are assessed at laboratory scale. The experimental system consisted of a 1 L differential circular flow reactor and an ozone generator rated at 5 g O3/h. Results show that ozone oxidation combined with activated carbon adsorption increases the overall BT oxidation rate with respect to the ozonation process and activated carbon adsorption. In the presence of free radical scavenger, only a 44% reduction in BT removal rate is observed in the simultaneous treatment, as compared with 72% when ozonation treatment is used, suggesting that BT oxidation reactions mainly take place on the activated carbon surface.

  14. DFT simulation, quantum chemical electronic structure, spectroscopic and structure-activity investigations of 2-benzothiazole acetonitrile

    Science.gov (United States)

    Arjunan, V.; Thillai Govindaraja, S.; Jose, Sujin P.; Mohan, S.

    2014-07-01

    The Fourier transform infrared and FT-Raman spectra of 2-benzothiazole acetonitrile (BTAN) have been recorded in the range 4000-450 and 4000-100 cm-1 respectively. The conformational analysis of the compound has been carried out to obtain the stable geometry of the compound. The complete vibrational assignment and analysis of the fundamental modes of the compound are carried out using the experimental FTIR and FT-Raman data and quantum chemical studies. The experimental vibrational frequencies are compared with the wavenumbers derived theoretically by B3LYP gradient calculations employing the standard 6-31G**, high level 6-311++G** and cc-pVTZ basis sets. The structural parameters, thermodynamic properties and vibrational frequencies of the normal modes obtained from the B3LYP methods are in good agreement with the experimental data. The 1H (400 MHz; CDCl3) and 13C (100 MHz; CDCl3) nuclear magnetic resonance (NMR) spectra are also recorded. The electronic properties, the energies of the highest occupied and lowest unoccupied molecular orbitals are measured by DFT approach. The kinetic stability of the molecule has been determined from the frontier molecular orbital energy gap. The charges of the atoms and the structure-chemical reactivity relations of the compound are determined by its chemical potential, global hardness, global softness, electronegativity, electrophilicity and local reactivity descriptors by conceptual DFT methods. The non-linear optical properties of the compound have been discussed by measuring the polarisability and hyperpolarisability tensors.

  15. Synthesis and cytotoxic activity of certain benzothiazole derivatives against human MCF-7 cancer cell line.

    Science.gov (United States)

    Mohamed, Lamia W; Taher, Azza T; Rady, Ghada S; Ali, Mamdouh M; Mahmoud, Abeer E

    2016-10-04

    A new series of benzothiazole has been synthesized as cytotoxic agents. The new derivatives were tested for their cytotoxic activity toward the human breast cancer MCF-7 cell line against cisplatin as the reference drug. Many derivatives revealed good cytotoxic effect, whereas four of them, 4, 5c, 5d, and 6b, were more potent than cisplatin, with IC50 values being 8.64, 7.39, 7.56, and 5.15 μm compared to 13.33 μm of cisplatin. The four derivatives' cytotoxic activity was accompanied by regulating free radicals production, by increasing the activity of superoxide dismutase and depletion of intracellular reduced glutathione, catalase, and glutathione peroxidase activities, accordingly, the high production of hydrogen peroxide, nitric oxide, and other free radicals causing tumor cell death as monitored by reduction in the synthesis of protein and nucleic acids. Most of the tested compounds showed potent to moderate growth inhibitory activity; in particular, compound 6b exhibited the highest activity suggesting it is a lead compound in cytotoxic activity.

  16. Experimental and theoretical study of three new benzothiazole-fused carbazole derivatives

    Science.gov (United States)

    Shi, He-ping; Xu, Lei; Cheng, Ying; He, Jing-yuan; Dai, Jian-xin; Xing, Li-wen; Chen, Bai-quan; Fang, Li

    2011-10-01

    Three new D-π-A type compounds, each containing one benzothiazole ring as an electron acceptor and one N-ethylcarbazole group as electron donor, were synthesized and characterized by elemental analysis, NMR, MS and thermogravimetric analysis. The absorption and emission spectra of three compounds were experimentally determined in several solvents and were simultaneously computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated reorganization energy for hole and electron indicates that three compounds are in favor of hole transport than electron transport. The calculated absorption and emission wavelengths are well coincident with the measured data. The calculated lowest-lying absorption spectra can be mainly attributed to intramolecular charge transfer (ICT). And the calculated fluorescence spectra can be mainly described as originating from an excited state with intramolecular charge transfer (ICT) character. The results show that three compounds exhibited excellent thermal stability and high fluorescence quantum yields, indicating their potential applications as excellent optoelectronic material in optical field.

  17. Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents.

    Science.gov (United States)

    Kharbanda, Chetna; Alam, Mohammad Sarwar; Hamid, Hinna; Javed, Kalim; Bano, Sameena; Dhulap, Abhijeet; Ali, Yakub; Nazreen, Syed; Haider, Saqlain

    2014-11-01

    The present study aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two compounds 5a and 5d alleviated inflammation more than the standard drug celecoxib. Eight compounds 5 b, 5 c, 5 e, 5 g, 5 h, 6 b, 6 e and 6 f showed anti-inflammatory activity comparable to celecoxib. To understand the mode of action, COX-2 enzyme assay and TNF-α assay were carried out. All the active compounds were assessed for their cytotoxicity. The ulcerogenic risk evaluation was performed on the active compounds that were not found to be cytotoxic. Out of ten active compounds, two compounds (5 d and 6 f) were finally found to be the most potent anti-inflammatory agents attributing to the suppression of the COX-2 enzyme activity and TNF-α production without being either cytotoxic or ulcerogenic.

  18. New benzothiazole/thiazole-containing hydroxamic acids as potent histone deacetylase inhibitors and antitumor agents.

    Science.gov (United States)

    Tung, Truong Thanh; Oanh, Dao Thi Kim; Dung, Phan Thi Phuong; Hue, Van Thi My; Park, Sang Ho; Han, Byung Woo; Kim, Youngsoo; Hong, Jin-Tae; Han, Sang-Bae; Nam, Nguyen-Hai

    2013-12-01

    Results from clinical studies have demonstrated that inhibitors of histone deacetylase (HDAC) enzymes possess promise for the treatment of several types of cancer. Zolinza(®) (widely known as SAHA) has been approved by the FDA for the treatment of T-cell lymphoma. As a continuity of our ongoing research to find novel small molecules to target these important enzymes, we synthesized a series of benzothiazole-containing analogues of SAHA and found several compounds with very potent anticancer cytotoxicity. In this study, three more compounds of this type, including N(1)-(6-chlorobenzo[d]thiazol-2-yl)-N(8)-hydroxyoctanediamide (3a), N(1)-[6-(trifluoromethyl)benzo[d]thiazol-2-yl]-N(8)-hydroxyoctanediamide (3b) and N(1)-(thiazol-2-yl)-N(8)-hydroxyoctanediamide (6) were synthesized and evaluated for HDAC inhibition and cytotoxic activities. All three compounds showed very potent HDAC inhibitory effects. Docking revealed that both two compounds 3a, 3b showed higher affinities towards HDAC(8) compared to SAHA. In vitro, compound 3a exhibited cytotoxicity equipotent to SAHA against five human cancer cell lines. In term of in vivo activity, compound 3a demonstrated equivalent efficacy to SAHA in mouse xenograft model.

  19. Effect of Co-substrate on Degradation of Benzothiazole in MEC

    Institute of Scientific and Technical Information of China (English)

    Huandi Huang; Jie Ding; Xianshu Liu; Guojun Xie; Dihui Song

    2016-01-01

    Due to its persistence and bio⁃toxicity, benzothiazole ( BTH ) cannot be biodegraded efficiently. Recent work has shown that removal rates of biorefractory organics can be enhanced by the addition of co⁃substrates. In this work, ethanol, acetate, propionate and butyrate were added as co⁃substrates in order to promote the degradation of BTH in microbial electrolysis cell (MEC). By probing the changes in degradation rates of BTH in the presence of different co⁃substrates, it was observed that all the four co⁃substrates can enhance the BTH degradation in MEC, both the efficiency ( EBTH ) and the rate ( RBTH ) . It was also found that acetate is more effective than others, which made the degradation efficiency of BTH up to 90% with acetate⁃C at 350 mg/L ( measuring by the carbon content of co⁃substrate, the same below) ,within 6 h and the degradation rate of BTH arrived 0.001 2/( mg·h) . The microbacteria in MEC have also been influenced by different co⁃substrates. This metabolism of the co⁃substrates enables the microbacteria on anode to generate ATP and thus grow to ensure the microbacteria activity. Therefore, this work showed that the addition of co⁃substrates such as acetate can be a novel and efficient approach for improving the elimination of BTH from wastewaters by MEC system.

  20. The Detoxification and Degradation of Benzothiazole from the Wastewater in Microbial Electrolysis Cells.

    Science.gov (United States)

    Liu, Xianshu; Ding, Jie; Ren, Nanqi; Tong, Qingyue; Zhang, Luyan

    2016-12-20

    In this study, the high-production-volume chemical benzothiazole (BTH) from synthetic water was fully degraded into less toxic intermediates of simple organic acids using an up-flow internal circulation microbial electrolysis reactor (UICMER) under the hydraulic retention time (HRT) of 24 h. The bioelectrochemical system was operated at 25 ± 2 °C and continuous-flow mode. The BTH loading rate varied during experiments from 20 g·m(-3)·day(-1) to 110 g·m(-3)·day(-1). BTH and soluble COD (Chemical Oxygen Demand) removal efficiency reached 80% to 90% under all BTH loading rates. Bioluminescence based Shewanella oneidensis strain MR-1 ecotoxicity testing demonstrated that toxicity was largely decreased compared to the BTH wastewater influent and effluent of two control experiments. The results indicated that MEC (Microbial Electrolysis Cell) was useful and reliable for improving BTH wastewater treatment efficiency, enabling the microbiological reactor to more easily respond to the requirements of higher loading rate, which is meaningful for economic and efficient operation in future scale-up.

  1. 2-Anilino-4-(1,3-benzothiazol-2-yl-5-(4-chlorobenzoylthiophene-3-carbonitrile

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2012-08-01

    Full Text Available In the title compound, C25H14ClN3OS2, the central thiophene ring [maximum deviation = 0.011 (1 Å] makes dihedral angles of 55.72 (5, 13.36 (5 and 46.77 (4° with the adjacent chloro-substituted benzene ring, the benzene ring and the 1,3-benzothiazole ring system [maximum deviation = 0.012 (1 Å], respectively. An intramolecular C—H...S(thienyl hydrogen bond generates an S(6 ring motif in the molecule. In the crystal, molecules are linked by pairs of N—H...N hydrogen bonds into inversion dimers and the dimers are further connected by C—H...O hydrogen bonds into tapes running along [100]. Aromatic π–π stacking interactions are also observed [centroid-to-centroid distances = 3.6116 (6 and 3.7081 (6 Å].

  2. A QSAR study and molecular design of benzothiazole derivatives as potent anticancer agents

    Institute of Scientific and Technical Information of China (English)

    CHEN JinCan; QIAN Li; SHEN Yong; CHEN LanMei; ZHENG KangCheng

    2008-01-01

    A quantitative structure-activity relationship (QSAR) of a series of benzothiazole derivatives showing a potent and selective cytotoxicity against a tumorigenic cell line has been studied by using the density functional theory (DFT), molecular mechanics (MM+) and statistical methods, and the QSAR equation was established via a correlation analysis and a stepwise regression analysis.A new scheme deter-mining outliers by "leave-one-out" (LOO) cross-validation coefficient (q2n-1) was suggested and suc-cessfully used.In the established optimal equation (excluding two outliers), the steric parameter (MRR) and the net charge (QFR) of the first atom of the substituent (R), as well as the square of hydrophobic parameter (IgP)2 of the whole molecule, are the main independent factors contributing to the anticancer activities of the compounds.The fitting correlation coefficient (R2) and the cross-validation coefficient (q2) values are 0.883 and 0.797, respectively.It indicates that this model has a significantly statistical quality and an excellent prediction ability.Based on the QSAR studies, 4 new compounds with high predicted anticancer activities have been theoretically designed and they are expected to be confirmed experimentally.

  3. Design, synthesis, and AChE inhibitory activity of new benzothiazole-piperazines.

    Science.gov (United States)

    Demir Özkay, Ümide; Can, Özgür Devrim; Sağlık, Begüm Nurpelin; Acar Çevik, Ulviye; Levent, Serkan; Özkay, Yusuf; Ilgın, Sinem; Atlı, Özlem

    2016-11-15

    In the current study, 14 new benzothiazole-piperazine compounds were designed to meet the structural requirements of acetylcholine esterase (AChE) inhibitors. The target compounds were synthesised in three steps. Structures of the newly synthesised compounds (7-20) were confirmed using IR, (1)H NMR, (13)C NMR, and HRMS methods. The inhibitory potential of the compounds on AChE (E.C.3.1.1.7, from electric eel) was then investigated. Among the compounds, 19 and 20 showed very good activity on AChE enzyme. Kinetics studies were performed to observe the effects of the most active compounds on the substrate-enzyme relationship. Cytotoxicity studies, genotoxicity studies, and theoretical calculation of pharmacokinetics properties were also carried out. The compounds 19 and 20 were found to be nontoxic in both of the toxicity assays. A good pharmacokinetics profile was predicted for the synthesised compounds. Molecular docking studies were performed for the most active compounds, 19 and 20, and interaction modes with enzyme active sites were determined. Docking studies indicated a strong interaction between the active sites of AChE enzyme and the analysed compounds.

  4. The Detoxification and Degradation of Benzothiazole from the Wastewater in Microbial Electrolysis Cells

    Directory of Open Access Journals (Sweden)

    Xianshu Liu

    2016-12-01

    Full Text Available In this study, the high-production-volume chemical benzothiazole (BTH from synthetic water was fully degraded into less toxic intermediates of simple organic acids using an up-flow internal circulation microbial electrolysis reactor (UICMER under the hydraulic retention time (HRT of 24 h. The bioelectrochemical system was operated at 25 ± 2 °C and continuous-flow mode. The BTH loading rate varied during experiments from 20 g·m−3·day−1 to 110 g·m−3·day−1. BTH and soluble COD (Chemical Oxygen Demand removal efficiency reached 80% to 90% under all BTH loading rates. Bioluminescence based Shewanella oneidensis strain MR-1 ecotoxicity testing demonstrated that toxicity was largely decreased compared to the BTH wastewater influent and effluent of two control experiments. The results indicated that MEC (Microbial Electrolysis Cell was useful and reliable for improving BTH wastewater treatment efficiency, enabling the microbiological reactor to more easily respond to the requirements of higher loading rate, which is meaningful for economic and efficient operation in future scale-up.

  5. Importance of surface chemical properties in catalytic ozonation of benzothiazole promoted by activated carbon

    Energy Technology Data Exchange (ETDEWEB)

    Valdes, H.; Zaror, C.A. [Chemical Eng. Dept., Univ. of Concepcion, Concepcion (Chile)

    2003-07-01

    The combined use of ozone and activated carbon to treat toxic effluents has increased in recent years. Activated carbon has been shown to enhance ozone oxidation of organic compounds. However, little is known about the influence of carbon surface active sites on ozonation of organic pollutants. This paper presents experimental results on the effect of metal oxides and oxygenated surface groups on such reaction. Benzothiazole (BT) was selected as a target organic compound in this study due its environmental concern. Activated carbons with different surface chemical composition were prepared from a filtrasorb-400 activated carbon. Pre-treatment included ozonation, demineralisation and deoxygenation of activated carbon. BT degradation experiments were conducted in a fixed bed reactor loaded with 2 g of carbon samples. The reactor was fed with an O{sub 2}/O{sub 3} mixture (2 dm{sup 3}/min, 5 g O{sub 3}/h), for a given exposure time, in the range 10-120 min, at 298 K and 1 atm. The results suggest that high electron density from the carbon basal planes and surface metal oxides are primarily responsible for increase in the overall BT oxidation rate; whereas high surface concentration of electron withdrawing groups such as carboxylic acids, and carboxylic anhydrides retarded the overall BT oxidation rate. (orig.)

  6. Ozonation of benzothiazole saturated-activated carbons: Influence of carbon chemical surface properties

    Energy Technology Data Exchange (ETDEWEB)

    Valdes, H. [Facultad de Ingenieria, Universidad Catolica de la Santisima Concepcion, Caupolican 491, Concepcion (Chile)]. E-mail: hvaldes@ucsc.cl; Zaror, C.A. [Departamento de Ingenieria Quimica (F. Ingenieria), Universidad de Concepcion, Correo 3, Casilla 160-C, Concepcion (Chile)

    2006-09-21

    The combined or sequential use of ozone and activated carbon to treat toxic effluents has increased in recent years. However, little is known about the influence of carbon surface active sites on ozonation of organic adsorbed pollutants. This paper presents experimental results on the effect of metal oxides and oxygenated surface groups on gaseous ozonation of spent activated carbons. Benzothiazole (BT) was selected as a target organic compound in this study due to its environmental concern. Activated carbons with different chemical surface composition were prepared from a Filtrasorb-400 activated carbon. Pre-treatment included: ozonation, demineralisation, and deoxygenation of activated carbon. Ozonation experiments of BT saturated-activated carbons were conducted in a fixed bed reactor loaded with 2 g of carbon samples. The reactor was fed with an O{sub 2}/O{sub 3} gas mixture (2 dm{sup 3}/min, 5 g O{sub 3}/h), for a given exposure time, in the range 10-120 min, at 298 K and 1 atm. Results show that extended gaseous ozonation of activated carbon saturated with BT led to the effective destruction of the adsorbate by oxidation reactions. Oxidation of BT adsorbed on activated carbon seemed to occur via both direct reaction with ozone molecules, and by oxygen radical species generated by catalytic ozone decomposition on metallic surface sites.

  7. Novel Ru(III) Complexes with Some Benzothiazole Derivatives: Synthesis, Physicochemical and Pharmacological Investigations.

    Science.gov (United States)

    Nikolova, A; Momekov, G; Bakalova, A; Nikolova, K; Ivanov, D

    2015-06-01

    In this work we present 3 new complexes of Ruthenium (III) with a general formula HL[Ru(L)2Cl4], where L=benzothiazole, 2-methylbenzothiazole and 2-mercaptobenzothiazole. The syntheses were carried out in polar medium under argon. The compounds obtained were characterised by IR-, (1)H-NMR- (13)C-NMR-, UV-VIS-spectroscopy and conductivity measurements. The ligands behaved as monodentate, bounding Ru(III) through the nitrogen atoms from the heterocycle. The cytotoxicity of the new complexes was tested against 2 human leukemic cell lines (K-562 and KE-37), using the MTT-dye reduction assay. The Ru(III) coordination compound with 2-methylbenzothiazole displayed superior activity compared to the other novel complexes. Its IC50 values were comparable to that of the reference cytotoxic drug cisplatin. In general, the ligands displayed only marginal inhibitory effects on the human leukemic cell lines. Moreover, the ability of the complexes to trigger apoptosis was evaluated using a commercially available DNA-fragmentation ELISA kit and the obtained data indicated that their proapoptotic effects well correlate to the MTT-bioassay data.

  8. Synthesis, materials characterization and opto(electrical) properties of unsymmetrical azomethines with benzothiazole core

    Science.gov (United States)

    Iwan, Agnieszka; Palewicz, Marcin; Krompiec, Michal; Grucela-Zajac, Marzena; Schab-Balcerzak, Ewa; Sikora, Andrzej

    2012-11-01

    Optical (UV-vis and photoluminescence) properties of two soluble organic molecules based on azomethines with benzothiazole core (BTA1 and BTA2) were reported. The structures of both compounds are characterized by means FTIR, 1H NMR, and 13C NMR spectroscopy and elemental analysis; the results show an agreement with the proposed structure. The investigated compounds emitted blue light. Influence of excitation wavelength and concentration on maximum and intensity of emission of BTA1 and BTA2 was found. Electrochemical properties of the compounds were studied by differential pulse voltammetry. Introduction of fluorine moieties (BTA1) resulted in lower energy band gap (Eg) of approximately ˜0.5 eV, whereas BTA2 showed Eg of ˜2.8 eV. The devices comprised of BTA1 with P3HT:PCBM (1:1:1) showed an open circuit voltage (VOC) of 0.40 V, a short circuit current (JSC) of 1.19 mA/cm2, and a fill factor (FF) of 0.23, giving a power-conversion efficiency (PCE) of 0.10% under AM1.5G irradiation (100 mW/cm2).

  9. A QSAR study and molecular design of benzothiazole derivatives as potent anticancer agents

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    A quantitative structure-activity relationship (QSAR) of a series of benzothiazole derivatives showing a potent and selective cytotoxicity against a tumorigenic cell line has been studied by using the density functional theory (DFT), molecular mechanics (MM+) and statistical methods, and the QSAR equation was established via a correlation analysis and a stepwise regression analysis. A new scheme determining outliers by "leave-one-out" (LOO) cross-validation coefficient (q2n-i) was suggested and successfully used. In the established optimal equation (excluding two outliers), the steric parameter (MRR) and the net charge (QFR) of the first atom of the substituent (R), as well as the square of hydrophobic parameter (lgP)2 of the whole molecule, are the main independent factors contributing to the anticancer activities of the compounds. The fitting correlation coefficient (R2) and the cross-validation coefficient (q2) values are 0.883 and 0.797, respectively. It indicates that this model has a significantly statistical quality and an excellent prediction ability. Based on the QSAR studies, 4 new compounds with high predicted anticancer activities have been theoretically designed and they are expected to be confirmed experimentally.

  10. A novel acidic pH fluorescent probe based on a benzothiazole derivative.

    Science.gov (United States)

    Ma, Qiujuan; Li, Xian; Feng, Suxiang; Liang, Beibei; Zhou, Tiqiang; Xu, Min; Ma, Zhuoyi

    2017-04-15

    A novel acidic pH fluorescent probe 1 based on a benzothiazole derivative has been designed, synthesized and developed. The linear response range covers the acidic pH range from 3.44 to 6.46, which is valuable for pH researches in acidic environment. The evaluated pKa value of the probe 1 is 4.23. The fluorescence enhancement of the studied probe 1 with an increase in hydrogen ions concentration is based on the hindering of enhanced photo-induced electron transfer (PET) process. Moreover, the pH sensor possesses a highly selective response to H(+) in the presence of metal ions, anions and other bioactive small molecules which would be interfere with its fluorescent pH response. Furthermore, the probe 1 responds to acidic pH with short response time that was less than 1min. The probe 1 has been successfully applied to confocal fluorescence imaging in live HeLa cells and can selectively stain lysosomes. All of such good properties prove it can be used to monitoring pH fluctuations in acidic environment with high sensitivity, pH dependence and short response time.

  11. An iminocoumarin benzothiazole-based fluorescent probe for imaging hydrogen sulfide in living cells.

    Science.gov (United States)

    Zhang, Huatang; Xie, Yusheng; Wang, Ping; Chen, Ganchao; Liu, Ruochuan; Lam, Yun-Wah; Hu, Yi; Zhu, Qing; Sun, Hongyan

    2015-04-01

    Hydrogen sulfide (H2S) has recently been identified as the third gaseous signaling molecule that is involved in regulating many important cellular processes. We report herein a novel fluorescent probe for detecting H2S based on iminocoumarin benzothiazole scaffold. The probe displayed high sensitivity and around 80-fold increment in fluorescence signal after reacting with H2S under physiological condition. The fluorescent intensity of the probe was linearly related to H2S concentration in the range of 0-100 μM with a detection limit of 0.15 μM (3σ/slope). The probe also showed excellent selectivity towards H2S over other biologically relevant species, including ROS, RSS and RNS. Its selectivity for H2S is 32 folds higher than other reactive sulfur species. Furthermore, the probe has been applied for imaging H2S in living cells. Cell imaging experiments demonstrated that the probe is cell-permeable and can be used to monitor the alteration of H2S concentrations in living cells. We envisage that this probe can provide useful tools to further elucidate the biological roles of H2S.

  12. Photophysical properties and photostability of novel benzothiazole-based D- π- A- π- D systems

    Science.gov (United States)

    Cigáň, Marek; Gáplovský, Anton; Gajdoš, Peter; Magdolen, Peter; Zahradník, Pavol; Vetríková, Zuzana

    2010-12-01

    The photophysical properties and photochemical stability of two novel D- π- A- π- D systems based on a benzothiazole core and terminal N, N-dimethylaminophenyl and N, N-diphenylaminophenyl groups were investigated. The quantum yield of photoreactions ( Φ) was determined for various oxygen concentrations in the solvent (CH 2Cl 2) and various irradiation wavelengths. Trans- cis photoisomerization is proposed as a photobleaching mechanism during irradiation at longer wavelength due to charge-transfer transitions. Solution deoxygenation led to an unusual decrease in the photostability of the compounds investigated, most likely because of cation radical formation. The population of higher excited states for short-wavelength irradiation opened another degradation pathway and the overall degradation percentage decreased in comparison with long-wavelength irradiation. We assume that photoisomerization of the second double bond and electron transfer to CH 2Cl 2 (and subsequent oxidation reactions) contribute to this slower degradation branch. Singlet oxygen contributes significantly, albeit to the smallest values of Φ, to the overall photodegradation for both types of irradiation.

  13. 6,6 '-Disubstituted benzothiazole trimethine cyanines - new fluorescent dyes for DNA detection

    Science.gov (United States)

    Kovalska, Vladyslava B.; Volkova, Kateryna D.; Losytskyy, Mykhaylo Yu.; Tolmachev, Olexiy I.; Balanda, Anatoliy O.; Yarmoluk, Sergiy M.

    2006-10-01

    The influence of methyl-, 2-hydroxyethyl-, dimethyl-, diethyl- and benzoyl-amino substituents in the 6,6'-positions of benzothiazole heterocycle of trimethine cyanines on their spectral-luminescent properties and behavior in presence of DNA, RNA and BSA was studied. It was shown that incorporation of 6,6'-substituents generally leads to the increase in dyes tendency to aggregation, resulting in the considerable decrease in the emission intensity of the disubstituted dyes as compared to the unsubstituted ones. Emission of the studied 6,6'-disubstited dyes in DNA presence is considerably more intensive than in presence of RNA, that points on the existing of DNA binding preference for the mentioned dyes. Insertion of benzoyl-amino groups into the 6,6'-positions permitted us to design the DNA-sensitive dyes on the basis of symmetric trimethine cyanines with unsubstituted polymethine chain, while typically such dyes slightly respond on the presence of biopolymers. 6,6'-Benzoyl-amino-disubstituted trimethine cyanines are proposed as efficient dyes for DNA detection.

  14. 6,6'-Disubstituted benzothiazole trimethine cyanines--new fluorescent dyes for DNA detection.

    Science.gov (United States)

    Kovalska, Vladyslava B; Volkova, Kateryna D; Losytskyy, Mykhaylo Yu; Tolmachev, Olexiy I; Balanda, Anatoliy O; Yarmoluk, Sergiy M

    2006-10-01

    The influence of methyl-, 2-hydroxyethyl-, dimethyl-, diethyl- and benzoyl-amino substituents in the 6,6'-positions of benzothiazole heterocycle of trimethine cyanines on their spectral-luminescent properties and behavior in presence of DNA, RNA and BSA was studied. It was shown that incorporation of 6,6'-substituents generally leads to the increase in dyes tendency to aggregation, resulting in the considerable decrease in the emission intensity of the disubstituted dyes as compared to the unsubstituted ones. Emission of the studied 6,6'-disubstited dyes in DNA presence is considerably more intensive than in presence of RNA, that points on the existing of DNA binding preference for the mentioned dyes. Insertion of benzoyl-amino groups into the 6,6'-positions permitted us to design the DNA-sensitive dyes on the basis of symmetric trimethine cyanines with unsubstituted polymethine chain, while typically such dyes slightly respond on the presence of biopolymers. 6,6'-Benzoyl-amino-disubstituted trimethine cyanines are proposed as efficient dyes for DNA detection.

  15. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry.

    Science.gov (United States)

    Keri, Rangappa S; Patil, Mahadeo R; Patil, Siddappa A; Budagumpi, Srinivasa

    2015-01-07

    Benzothiazole (BTA) and its derivatives are the most important heterocyclic compounds, which are common and integral feature of a variety of natural products and pharmaceutical agents. BTA shows a variety of pharmacological properties, and its analogs offer a high degree of structural diversity that has proven useful for the search of new therapeutic agents. The broad spectrum of pharmacological activity in individual BTA derivative indicates that, this series of compounds is of an undoubted interest. The related research and developments in BTA-based medicinal chemistry have become a rapidly developing and increasingly active topic. Particularly, numerous BTA-based compounds as clinical drugs have been extensively used in practice to treat various types of diseases with high therapeutic potency. This work systematically gives a comprehensive review in current developments of BTA-based compounds in the whole range of medicinal chemistry as anticancer, antibacterial, antifungal, antiinflammatory, analgesic, anti-HIV, antioxidant, anticonvulsant, antitubercular, antidiabetic, antileishmanial, antihistaminic, antimalarial and other medicinal agents. It is believed that, this review article is helpful for new thoughts in the quest for rational designs of more active and less toxic BTA-based drugs, as well as more effective diagnostic agents and pathologic probes.

  16. Bis(2-amino-1,3-benzothiazole-κN3dichloridozinc(II ethanol hemisolvate

    Directory of Open Access Journals (Sweden)

    Young-Inn Kim

    2012-02-01

    Full Text Available In the title compound, [ZnCl2(C7H6N2S2]·0.5CH3CH2OH, the ZnII atom is coordinated by two N atoms of two 2-aminobenzothiazole ligands and two Cl atoms within a distorted tetrahedral geometry. The dihedral angle between the N/Zn/N and Cl/Zn/Cl planes is 86.22 (7°. The benzothiazole molecules are almost perpendicular to each other, forming a dihedral angle of 80.20 (8°. The molecular structure is stabilized by intramolecular N—H...Cl hydrogen bonds. In the crystal, intermolecular N—H...Cl hydrogen bonds link the molecules into a three-dimensional network. The SQUEEZE procedure in PLATON [Spek (2009. Acta Cryst. D65, 148–155] was used to model a disordered ethanol solvent molecule; the calculated unit-cell data allow for the presence of half of this molecule in the asymmetric unit.

  17. Hybrid Moving Bed Biofilm Reactor for the biodegradation of benzotriazoles and hydroxy-benzothiazole in wastewater.

    Science.gov (United States)

    Mazioti, Aikaterini A; Stasinakis, Athanasios S; Psoma, Aikaterini K; Thomaidis, Nikolaos S; Andersen, Henrik R

    2017-02-05

    A laboratory scale Hybrid Moving Bed Biofilm Reactor (HMBBR) was used to study the removal of five benzotriazoles and one benzothiazole from municipal wastewater. The HMBBR system consisted of two serially connected fully aerated bioreactors that contained activated sludge (AS) and K3-biocarriers and a settling tank. The average removal of target compounds ranged between 41% (4-methyl-1H-benzotriazole; 4TTR) and 88% (2-hydroxybenzothiazole; OHBTH). Except for 4TTR, degradation mainly occurred in the first bioreactor. Calculation of biodegradation constants in batch experiments and application of a model for describing micropollutants removal in the examined system showed that AS is mainly involved in biodegradation of OHBTH, 1H-benzotriazole (BTR) and xylytriazole (XTR), carriers contribute significantly on 4TTR biodegradation, while both types of biomass participate on elimination of 5-chlorobenzotriazole (CBTR) and 5-methyl-1H-benzotriazole (5TTR). Comparison of the HMBBR system with MBBR or AS systems from literature showed that the HMBBR system was more efficient for the biodegradation of the investigated chemicals. Biotransformation products of target compounds were identified using ultra high-performance liquid chromatography, coupled with a quadrupole-time-of-flight high-resolution mass spectrometer (UHPLC-QToF-MS). Twenty two biotransformation products were tentatively identified, while retention time denoted the formation of more polar transformation products than the parent compounds.

  18. The Detoxification and Degradation of Benzothiazole from the Wastewater in Microbial Electrolysis Cells

    Science.gov (United States)

    Liu, Xianshu; Ding, Jie; Ren, Nanqi; Tong, Qingyue; Zhang, Luyan

    2016-01-01

    In this study, the high-production-volume chemical benzothiazole (BTH) from synthetic water was fully degraded into less toxic intermediates of simple organic acids using an up-flow internal circulation microbial electrolysis reactor (UICMER) under the hydraulic retention time (HRT) of 24 h. The bioelectrochemical system was operated at 25 ± 2 °C and continuous-flow mode. The BTH loading rate varied during experiments from 20 g·m−3·day−1 to 110 g·m−3·day−1. BTH and soluble COD (Chemical Oxygen Demand) removal efficiency reached 80% to 90% under all BTH loading rates. Bioluminescence based Shewanella oneidensis strain MR-1 ecotoxicity testing demonstrated that toxicity was largely decreased compared to the BTH wastewater influent and effluent of two control experiments. The results indicated that MEC (Microbial Electrolysis Cell) was useful and reliable for improving BTH wastewater treatment efficiency, enabling the microbiological reactor to more easily respond to the requirements of higher loading rate, which is meaningful for economic and efficient operation in future scale-up. PMID:27999421

  19. Novel fluorene-carzazole-based conjugated copolymers containing pyrazoline and benzothiazole segments for blue light-emitting materials

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A series of novel fluorene-carbazole-based copolymers with pyrazoline and benzothiazole units were synthesized successfully through Suzuki coupling reactions. The molecular structures and thermal properties of these polymers were characterized by FT-IR,1H NMR, DSC and TGA. GPC results indicated that the weight-average molecular weight (Mw) and polydispersity of these polymers were in range (12,000-14,000) and (1.8-2.0), respectively. The two resulting polymers have high photoluminescence quantum efficiency implying that they may be promising candidates for polymer light-emitting diodes (PLEDs).

  20. tert-Butyl N-[6-(N,N-dipropylcarbamoyl-1,3-benzothiazol-2-yl]carbamate

    Directory of Open Access Journals (Sweden)

    Xin Fang

    2010-05-01

    Full Text Available The title compound C19H27N3O3S, crystallizes with two unique molecules in the asymmetric unit. The benzene ring of each benzothiazole unit carries a dipropylcarbamoyl substituent in the 6-position and a tert-butyl carbamate unit on each thiazole ring. In the crystal structure, intermolecular N—H...N and weak C—H...O hydrogen bonds form centrosymmetric dimers. Additional C—H...O contacts construct a three-dimensional network. A very weak C—H...π contact is also present.

  1. The influence of the various central metals on photophysical and photochemical properties of benzothiazole-substituted phthalocyanines

    Science.gov (United States)

    Nas, Asiye; Dilber, Gülsev; Durmuş, Mahmut; Kantekin, Halit

    2015-01-01

    The photophysical (fluorescence quantum yields and lifetimes, fluorescence quenching studies by 1,4-benzoquinone (BQ)) and photochemical (singlet oxygen quantum yields and photodegradation studies under light irradiation) properties of tetra-benzothiazole substituted metal-free (H2Pc, 1), lead (II) (PbPc, 2) and zinc(II) (ZnPc, 3) phthalocyanine compounds were investigated in tetrahydrofuran (THF) solution. All of these compounds did not show any aggregation and they produced good singlet oxygen (especially ZnPc). The influence of the various central metal ions (zinc, lead or without metal) on the photophysical and photochemical parameters was also investigated and compared.

  2. Synergistic Inhibition Effect of Zinc Acetylacetonate and Benzothiazole in Epoxy Coating on the Corrosion of Mild Steel

    Science.gov (United States)

    Amoozadeh, S. M.; Mahdavian, M.

    2015-06-01

    The corrosion inhibition effect of zinc acetylacetonate (ZAA) and benzothiazole (BTH) mixture was evaluated for mild steel in 3.5% NaCl solution. To this end, ZAA:BTH mixtures ranged from 6:1 to 1:6 mol ratios were examined by weight loss and open circuit potential to obtain optimal mole ratio. The optimal mixture of ZAA:BTH at 1:5 mol ratio showed a significant corrosion inhibition efficiency proved by electrochemical impedance spectroscopy and polarization studies. The addition of the optimal mixture of ZAA:BTH to epoxy coating showed a considerable increase of corrosion protection evaluated by salt spray exposure.

  3. Synthesis and antimicrobial evaluation of certain purine, benzothiazole and thiazole systems substituted with dialkylaminoalkyl-o-cresols

    Directory of Open Access Journals (Sweden)

    Khaled R.A. Abdellatif

    2015-03-01

    Full Text Available Novel series of dialkylaminoalkyl-o-cresols incorporated with purine nucleus 2a–b, benzothiazole nucleus 5a–b, 8a–b and thiazole nucleus 11a–d, 13a–d were synthesized through Mannich reaction. Structures of the newly synthesized compounds have been deduced on the basis of elemental analysis and spectral data. Antimicrobial activity evaluation was carried out for all synthesized compounds; most of them exerted comparable activity to ciprofloxacin and flucanazole. The thiazole derivatives 11a, 13c, 13d are the most potent compounds.

  4. 1-(6-Fluoro-1,3-benzothiazol-2-yl-3-phenyl-1H-pyrazole-4-carbaldehyde

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2011-12-01

    Full Text Available The asymmetric unit of the title compound, C17H10FN3OS, consists of two crystallographically independent molecules. In one molecule, the pyrazole ring makes dihedral angles of 6.51 (7 and 34.02 (9°, respectively, with the terminal 1,3-benzothiazole ring system and the phenyl ring, while in the other molecule these values are 6.41 (8 and 23.06 (9°. In the crystal, the molecules are linked by weak π–π [centroid–centroid distance = 3.7069 (10 Å] and C—H...π interactions.

  5. Differential encapsulation of trans-2-[4-(dimethylamino)styryl] benzothiazole in cyclodextrin hosts: Application towards nanotubular suprastructure formation

    Science.gov (United States)

    Purkayastha, Pradipta; Das, Debasmita; Syed Jaffer, S.

    2008-12-01

    The guest size dependent extent of encapsulation by cyclodextrins (CDs) of different sizes ( viz., α-, β-, and γ-) has been studied using cyclic voltammetry and fluorescence spectroscopy. Electrochemical and chemical oxidation methods have been used to understand the extent to which trans-2-[4-(dimethylamino)styryl]benzothiazole (DMASBT) gets encapsulated in the cyclodextrin cavities. The guest molecule can induce the formation of nanocapsules with cyclodextrin hosts due to hydrophobic interaction leading to the formation of nanotubes followed by suprastructures. The electrochemically obtained results were confirmed using chemical method. The differential encapsulation of DMASBT in the CDs may define the architecture of the nanotubes.

  6. Synthesis and Anti-inflammatory Activity of Some Novel 3-(6-Substituted-1, 3-benzothiazole-2-yl-2-[{(4-substituted phenyl amino} methyl] quinazolines-4 (3H-ones

    Directory of Open Access Journals (Sweden)

    Manish Srivastav

    2009-01-01

    Full Text Available A series of novel 3-(6-substituted-1, 3-benzothiazole-2-yl-2-[{(4-substituted phenyl amino} methyl] quinazolines-4(3H-ones were synthesized by treating 2-(chloromethyl-3-(6-substituted-1, 3-benzothiazole-2-yl quinazoline-4-(3H-one (IIa-d with various substituted amine. The compounds (IIa-d prepared by treating 2-[(chloroacetyl amino] benzoic acid with different 2-amino-6-substituted benzothiazole. Elemental analysis, IR, 1HNMR and mass spectral data confirmed the structure of the newly synthesized compounds. Synthesized quinazolines-4-one derivative were investigated for their anti-inflammatory and antibacterial activity.

  7. Piezochromic luminescence behaviors of two new benzothiazole-enamido boron difluoride complexes: intra- and inter-molecular effects induced by hydrostatic compression.

    Science.gov (United States)

    Wang, Xiaoqing; Liu, Qingsong; Yan, Hui; Liu, Zhipeng; Yao, Mingguang; Zhang, Qingfu; Gong, Shuwen; He, Weijiang

    2015-05-01

    Two new propeller-shaped benzothiazole-enamide boron difluoride complexes exhibiting piezochromic luminescence upon mechanical grinding or hydrostatic compression were prepared. The two analogues displayed the red shift in luminescence under high pressure, while compound 2 with ICT effects showed a more sensitive piezochromic response at low pressure (<1.5 GPa). The different piezochromic luminescence behaviors of these compounds were investigated.

  8. Determination of polar 1H-benzotriazoles and benzothiazoles in water by solid-phase extraction and liquid chromatography LTQ FT Orbitrap mass spectrometry

    NARCIS (Netherlands)

    van Leerdam, J.A.; Hogenboom, A.C.; van der Kooi, M.M.E.; de Voogt, P.

    2009-01-01

    A sensitive, reliable and robust method for the trace determination of six polar 1H-benzotriazoles and four benzothiazoles in drinking and surface water was developed. These compounds were extracted from water by solid-phase extraction and analyzed by Liquid Chromatography-Electrospray Mass Spectrom

  9. ZnO-beta zeolite:As an effective and eco-friendly heterogeneous catalyst for the synthesis of benzothiazole derivatives

    Institute of Scientific and Technical Information of China (English)

    Santosh; S.Katkar; Pravinkumar; H.Mohite; Lakshman; S.Gadekar; Kaluram; N.Vidhate; Machhindra; K.Lande

    2010-01-01

    A cheap and recyclable ZnO-beta zeolite was used as catalyst for the synthesis of benzothiazole derivatives.This method provides several advantages such as environmental friendliness,short reaction times,high yields,simple work-up procedure and catalyst was successfully reused for four cycles without significant loss of activity.

  10. Magnetic Ionic Liquid [bmim][FeCl4] as an Efficient Catalyst for the Synthesis of 2-Aryl Benzimidazoles and 2-Aryl Benzothiazoles Derivatives

    Directory of Open Access Journals (Sweden)

    Soheil Sayyahi

    2015-09-01

    Full Text Available The magnetic ionic liquid (MIL 1-butyl-3-methylimidazolium tetrachloro ferrate(III ([bmim][FeCl4] sufficiently catalyzes the one-pot condensation of 1,2 diaminobenzene or 2-aminobenzenethiol with different aromatic aldehydes producing benzimidazoles and benzothiazoles drivatives, respectively. The MIL showed high performance resulting great yields with appropriate reaction time.

  11. Identification of selected microorganisms from activated sludge capable of benzothiazole and benzotriazole transformation.

    Science.gov (United States)

    Kowalska, Katarzyna; Felis, Ewa

    2015-01-01

    Benzothiazole (BT) and benzotriazole (BTA) are present in the environment - especially in urban and industrial areas, usually as anthropogenic micropollutants. BT and BTA have been found in the municipal and industrial wastewater, rivers, soil, groundwater, sediments and sludge. The origins of those substances' presence in the environment are various industry branches (food, chemical, metallurgical, electrical), households and surface runoff from industrial areas. Increasingly strict regulations on water quality and the fact that the discussed compounds are poorly biodegradable, make them a serious problem in the environment. Considering this, it is important to look for environmentally friendly and socially acceptable ways to remove BT and BTA. The aim of this study was to identify microorganisms capable of BT and BTA transformation or/and degradation in aquatic environment. Selected microorganisms were isolated from activated sludge. The identification of microorganisms capable of BT and BTA removal was possible using molecular biology techniques (PCR, DNA sequencing). Among isolated microorganisms of activated sludge are bacteria potentially capable of BT and BTA biotransformation and/or removal. The most common bacteria capable of BT and BTA transformation were Rhodococcus sp., Enterobacter sp., Arthrobacter sp. They can grow in a medium with BT and BTA as the only carbon source. Microorganisms previously adapted to the presence of the studied substances at a concentration of 10 mg/l, showed a greater rate of growth of colonies on media than microorganisms unconditioned to the presence of such compounds. Results of the biodegradation test suggest that BT was degraded to a greater extent than BTA, 98-100% and 11-19%, respectively.

  12. Properties, theoretical study and crystal structure of 3-benzothiazole-9-ethyl carbazole.

    Science.gov (United States)

    Gu, Yingchun; Lin, Dayong; Fei, Xuening; Wang, Cuihong; Li, Ling; Tang, Yalin; Zhou, Jianguo

    2016-09-01

    The title compound of 3-benzothiazole-9-ethyl carbazole was synthesized by the reaction of 3-aldehyde-9-ethyl carbazole and 2-aminothiophenol. The compound was characterized by (1) H nuclear magnetic resonance (NMR) and mass spectrometry (MS). Its crystal structure was obtained and determined by single crystal X-ray diffraction. The results showed that the crystal belongs to the orthorhombic crystal system and the cell parameters of space group P2(1)2(1)2(1) were a = 5.6626 (12) Å, b = 12.606 (3) Å, c = 22.639 (5) Å, α = 90°, β = 90°, γ = 90°, V = 1616.0 (6) Å(3) , Z = 4, Dc = 1.350 mg/m(3) . The UV-vis and fluorescence spectra were also studied preliminarily. The fluorescence spectra of the title compound with bovine serum albumin (BSA) showed that BSA could be marked with the compound and the stability constant between them was 0.82 × 10(7)  M(-1) . Meanwhile, the crystal and molecule were theoretically surveyed by density functional tight-binding (DFTB). The results showed that there was an orbital overlap for lowest unoccupied molecular orbital (LUMO) between the neighbouring molecules for the crystal, which is different from the molecule structure. It was also showed that the crystal structure is a non-conductor. Copyright © 2016 John Wiley & Sons, Ltd.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2004-04-01

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

  14. Heterogeneous and homogeneous catalytic ozonation of benzothiazole promoted by activated carbon: kinetic approach.

    Science.gov (United States)

    Valdés, Héctor; Zaror, Claudio A

    2006-11-01

    Ozone oxidation combined with activated carbon adsorption (O(3)/AC) has recently started to be developed as a single process for water and wastewater treatment. While a number of aspects of aqueous ozone decomposition are well understood, the importance and relationship between aqueous ozone decomposition and organic contaminant degradation in the presence of activated carbon is still not clear. This study focuses on determining the contribution of homogeneous and heterogeneous reactions to organic contaminants removal in O(3)/AC system. Benzothiazole (BT) was selected as a target organic pollutant due to its environmental concern. A reactor system based on a differential circular flow reactor composed by a 19 cm(3) activated carbon fixed bed column and 1 dm(3) storage tank was used. Ozone was produced from pure and dry oxygen using an Ozocav ozone generator rated at 5 g O(3)h(-1). Experimental results show that BT removal rate was proportional to activated carbon dosage. Activated carbon surface contribution to BT oxidation reactions with ozone, increased with pH in absence of radical scavengers. The radical reaction contribution within the pH range 2-11 accounted for 67-83% for BT removal in O(3)/AC simultaneous treatment. Results suggest that at pH higher than the pH of the point of zero charge of the activated carbon dissociated acid groups such as carboxylic acid anhydrides and carboxylic acids present on activated carbon surface could be responsible for the observed increase in the ozone decomposition reaction rate. A simplified mechanism and a kinetic scheme representing the contribution of homogeneous and heterogeneous reactions on BT ozonation in the presence of activated carbon is proposed.

  15. Benzotriazole, benzothiazole, and benzophenone compounds in indoor dust from the United States and East Asian countries.

    Science.gov (United States)

    Wang, Lei; Asimakopoulos, Alexandros G; Moon, Hyo-Bang; Nakata, Haruhiko; Kannan, Kurunthachalam

    2013-05-07

    Organic corrosion inhibitors (OCIs), including ultraviolet light filters, are widely used in plastics, rubbers, colorants, and coatings to increase the performance of products. Derivatives of benzotriazole (BTR), benzothiazole (BTH), and benzophenone (BP) are high-production volume OCIs that have been detected in the environment and human tissues. However, knowledge of their occurrence in indoor environments, as well as human exposure to them, is still lacking. In this study, BTR, BTH, BP and their 12 derivatives were determined in indoor dust for the first time. All three groups of OCIs were found in all 158 indoor dust samples from the U.S. and three East Asian countries (China, Japan, and Korea). The geometric mean (GM) concentration of the sum of six BTRs (GM CΣBTRs) ranged from 20 to 90 ng/g among the four countries studied, with a maximum CΣBTRs of ∼2000 ng/g found in a dust sample from China. Tolyltriazole was the major derivative of BTR measured in dust. GM CΣBTHs in indoor dust from the four countries ranged from 600 to 2000 ng/g. 2-OH-BTH was the predominant BTH in dust from the U.S., Japan, and Korea. GM CΣBPs in dust ranged from 80 to 600 ng/g, with 2-OH-4-MeO-BP and 2,4-2OH-BP, contributing to the majority of ∑BP concentrations. Based on the concentrations of three types of OCIs in indoor dust, human exposure through dust ingestion was calculated. Daily intake of OCIs through dust ingestion was higher for people in the U.S., Japan, and Korea than in China; the residents in urban China are exposed to higher levels of OCIs via dust ingestion than are those in rural China.

  16. White Organic Light-Emitting Devices Based on 2-(2-Hydroxyphenyl) Benzothiazole and Its Chelate Metal Complex

    Institute of Scientific and Technical Information of China (English)

    WU Xiao-Ming; HUA Yu-Lin; WANG Zhao-Qi; ZHENG Jia-Jin; FENG Xiu-Lan; SUN Yuan-Yuan

    2005-01-01

    @@ We present three kinds of organic light-emitting devices (OLED) fabricated to achieve the emission of bright and pure white light. Device A, with a double-layered structure using 2-(2-hydroxyphenyl) benzothiazole (HBT) and poly (N-vinylcarbazole) (PVK) as the emitting layer (EML) and the hole transport layer (HTL) respectively,could realize the blue-green light emission. Bis-(2-(2-hydroxyphenyl) benzothiazole)zinc (Zn(BTZ)2), synthesized with zinc acetate dihydrate and HBT to form a complex, is used as main EMLs in a similar structure to fabricate devices B and C. Bright and pure white light emissions can be obtained from device C which was fabricated with a green-white emitting host Zn(BTZ)2 and red dopant 5,6,11,12-tetraphenylnaphthacene (rubrene). The maximum quantum efficiency of device C could reach 0.63%, and the corresponding brightness and CIE coordinates were 4000cd/m2 and (x = 0.341, y = 0.334) at the driving voltage of 20 V.

  17. Quantitative investigations of cation complexation of photochromic 8-benzothiazole-substituted benzopyran: towards metal-ion sensors.

    Science.gov (United States)

    Zakharova, Marianna I; Coudret, Christophe; Pimienta, Véronique; Micheau, Jean Claude; Delbaere, Stéphanie; Vermeersch, Gaston; Metelitsa, Anatoly V; Voloshin, Nikolai; Minkin, Vladimir I

    2010-02-01

    The photochromic, thermochromic and metallochromic behaviour of a series of three spiro[indoline-8-(benzothiazol-2-yl)-benzopyrans] has been investigated. The thermodynamic and kinetic parameters of their thermal equilibrium between the ring-closed (spiro) and ring-opened (merocyanine) isomeric forms have been determined using UV-Vis absorption and (1)H NMR spectroscopies. By adding Co(ii) and Ni(ii) ions in acetonitrile solution, 1 : 1 and 1 : 2 metal : merocyanine complexes are formed simultaneously. Using appropriate numerical methods, the kinetic analysis of the complexation allowed us to determine accurately key thermodynamic and spectroscopic parameters of the metal complexes. Results showed that the complexation strength is very sensitive to the size of the indoline nitrogen substituent. Complexation can be reversed by shining white light on the coloured complexes which regenerates the inactive spiropyran form, and releases the metallic ion; hence, these systems display fully reversible negative photochromism. The Zn(ii) complexes exhibit intense fluorescence in the 600-800 nm wavelength range. All these behaviours make these spiropyrans bearing benzothiazole heterocycles promising building blocks for the future construction of photodynamic chemosensors for transition metal ions.

  18. Corrosion inhibition efficiency and surface activity of benzothiazol-3-ium cationic Schiff base derivatives in hydrochloric acid

    Energy Technology Data Exchange (ETDEWEB)

    Negm, N.A., E-mail: nabelnegm@hotmail.co [Petrochemicals Department, Egyptian Petroleum Research Institute, Nasr City, Cairo (Egypt); Elkholy, Y.M.; Zahran, M.K. [Chemistry Department, Faculty of Science, Helwan University, Helwan (Egypt); Tawfik, S.M. [Petrochemicals Department, Egyptian Petroleum Research Institute, Nasr City, Cairo (Egypt)

    2010-10-15

    Research highlights: {yields} Benzothiazolium inhibitors show high corrosion inhibition for carbon steel. {yields} Weight loss and corrosion rates decrease by increasing inhibitor dose. {yields} Inhibition mechanism suggested as physisorption mechanism supported by adsorption free energy values. {yields} The adsorption of the inhibitors obeys Langmuir isotherm. {yields} Side chains have ascending order on the corrosion inhibition of the different inhibitors. - Abstract: Two series of cationic Schiff base surfactants namely: 2-(benzylideneamino)-3-(2-oxo-2-alkoxyethyl)-1,3-benzothiazol-3-ium bromide and 2-[(4-methoxybenzylidene)amino]-3-(2-oxo-2-alkoxyethyl)-1, 3-benzothiazol-3-ium bromide were prepared and confirmed using elemental analysis, FTIR, and {sup 1}H NMR spectra. The surface activity of the synthesized Schiff bases showed their tendency towards adsorption at the interfaces. The prepared compounds were evaluated as corrosion inhibitors for carbon steel in 0.5 M HCl solution using gravimetric and polarization measurements. By fitting the gravimetric data, some thermodynamic and kinetic parameters were estimated. The adsorption of the inhibitors on the carbon steel surface obeyed Langmuir adsorption isotherm and had a physical mechanism. Polarization measurements showed that the synthesized inhibitors act as mixed inhibitors for carbon steel in the acidic media. The results of the corrosion inhibition using two different methods showed narrow differences in the obtained values between the two methods within 5%.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2006-05-15

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

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

    Science.gov (United States)

    1987-07-01

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

  1. The Synthesis of Benzothiazole Derivate and Its Nature of Mould Proofing%苯并噻唑衍生物的合成及皮革防霉性能研究

    Institute of Scientific and Technical Information of China (English)

    海鹏; 万力; 徐兵; 张忠林; 王应红

    2009-01-01

    苯并噻唑与水合肼反应生成2-肼基苯并噻唑,再溴代合成6-溴-2-肼基苯并噻唑.用6-溴-2-肼基苯并噻唑与水杨醛反应合成邻-(6-溴-苯并噻唑2-亚肼甲基)苯酚.研究了合成的苯并噻唑衍生物对皮革黑曲霉的防霉效果.结果表明:合成的苯并噻唑衍生物对黑曲霉均表现较好的防霉效果;溴代和生成希夫碱能改善防霉效果,表明溴代和生成希夫碱用于皮革防霉有活性结构叠加的效应.%2-hydrazino-benzothiazole was synthesized by the benzothiazole and hydrazine hydrate and 6-bromo-2-hydrazino-benzothiazole was synthesized by brom(o)-. 0-[(6 bromo-2-benzothiazole hydrazono) methyl] phenol was also synthesized by 6-bromo-2-hydrazino-benzothiazole and salicylide .the different modified benzothiazole also was synthesized. The effects of mould proofing of different benzothiazole derivate to leather were investigated. The results shows there are good effects that benzothiazole derivate to leather, that the effect of mildewproof was better by brom (o)- and form of Schiff's base .this show there is effective of structure stratum of activity by brom(o)- and form of Schiff's base.

  2. Comparative Studies on Conventional and Microwave Synthesis of Some Benzimidazole, Benzothiazole and Indole Derivatives and Testing on Inhibition of Hyaluronidase

    Directory of Open Access Journals (Sweden)

    Joachim Jose

    2008-03-01

    Full Text Available We have synthesized twelve 2-substituted benzimidazole, benzothiazole andindole derivatives using on both microwave irradiation and conventional heating methods.The microwave method was observed to be more beneficial as it provides an increase ofyield from 3% to 113% and a 95 to 98 % reduction in time. All compounds were tested bya stains-all assay at pH 7 and by a Morgan-Elson assay at pH 3.5 for hyaluronidaseinhibitory activity at a concentration of 100 μM. The most potent compound was 2-(4-hydroxyphenyl-3-phenylindole (12 with an IC50 value of 107 μM at both pH 7 and 3.5.

  3. Biodegradation of benzotriazoles and hydroxy-benzothiazole in wastewater by activated sludge and moving bed biofilm reactor systems.

    Science.gov (United States)

    Mazioti, Aikaterini A; Stasinakis, Athanasios S; Pantazi, Ypapanti; Andersen, Henrik R

    2015-09-01

    Two laboratory scale fully aerated continuous flow wastewater treatment systems were used to compare the removal of five benzotriazoles and one benzothiazole by suspended and attached growth biomass. The activated sludge system was operated under low organic loading conditions. The moving bed biofilm reactor (MBBR) system consisted of two serially connected reactors filled with K3-biocarriers. It was either operated under low or high organic loading conditions. Target compounds were removed partially and with different rates in tested systems. For MBBR, increased loading resulted in significantly lower biodegradation for 4 out of 6 examined compounds. Calculation of specific removal rates (normalized to biomass) revealed that attached biomass had higher biodegradation potential for target compounds comparing to suspended biomass. Clear differences in the biodegradation ability of attached biomass grown in different bioreactors of MBBR systems were also observed. Batch experiments showed that micropollutants biodegradation by both types of biomass is co-metabolic.

  4. Design and synthesis of Quinazolinone, Benzothiazole derivatives bearing guanidinopropanoic acid moiety and their Schiff bases as cytotoxic and antimicrobial agents

    Directory of Open Access Journals (Sweden)

    Palani Venkatesh

    2016-09-01

    Full Text Available Two series of Benzothiazole, Quinazolinone derivatives bearing guanidinopropanoic acid (38 compounds including 27 intermediates and one series of Schiff base derivatives (14 compounds were synthesized, characterized then evaluated for their cytotoxicity against human cervix cell line (HeLa by MTT assay; antimicrobial activity against 11 pathogenic bacteria, 10 pathogenic fungus using standard of ciprofloxacin and Clotrimazole respectively. Compounds 13–18 showed significant activity against HeLa with IC50 range of 2–550 μM. Compound 3-(3-(6-hydroxybenzo[d]thiazol-2-ylguanidinopropanoic acid (18 showed potent activity against human HeLa cell line with the half maximal inhibitory concentration (IC50 values of 1.8 μM which was close to the value of the positive control, doxorubicin. Antimicrobial result indicated that, compounds showed differential activity against the tested fungus and bacteria. Compounds 11, 14, 38 and 49 exhibited potent antibacterial and antifungal activity.

  5. On the self-assembly of a highly selective benzothiazole-based TIM inhibitor in aqueous solution.

    Science.gov (United States)

    Hassan, Natalia; Gárate, M Pilar; Sandoval, Tania; Espinoza, Luis; Piñeiro, Ángel; Ruso, Juan M

    2010-11-16

    Benzothiazole is a common scaffold on which many bioactive structures, including protein inhibitors and biosensors, are based. The potential self-aggregation of such molecules to form nanoparticles is relevant for a number of practical applications. 3-(2-Benzothiazolylthio)-propanesulfonic acid (BTS) has been reported as a powerful and selective inhibitor of triosephosphate isomerase from Trypanosoma cruzi, the parasite that causes the Chagas' disease. Electrical conductivity, sound velocity, density, and nuclear magnetic resonance experiments as a function of temperature and of NaCl concentration have been performed in the present work to provide a comprehensive physicochemical description of this compound in aqueous solution. Molecular dynamics simulations of the same system were also performed to characterize the structure and dynamic behavior of the corresponding aggregates at several concentrations of BTS.

  6. Water and ionic liquid synergy: A novel approach for the synthesis of benzothiazole-2(3H-one

    Directory of Open Access Journals (Sweden)

    Malik A. Waseem

    2015-05-01

    Full Text Available Synergy between water, a green reaction medium and ionic liquid, a green catalyst has opened new vistas in the field of organic transformation. The developed methodology has emerged as an interesting combination for an environmentally benign, facile and efficient synthesis of benzothiazole-2(3H-one. Product was achieved in excellent yield by the reaction of structurally diverse 2-iodoanilines with potassium thiocyanate. The strategy involves nucleophilic substitution forming NC and SC bonds resulting in the desired heterocyclic scaffold. This novel approach is also helpful for the synthesis of other related heterocycles for the development of an important drug like library. The reaction proceeded smoothly at an ambient temperature.

  7. 苯并噻唑类杂环合成最新进展%Recent Advance in the Synthesis of Benzothiazoles

    Institute of Scientific and Technical Information of China (English)

    李鹏宇; 李江胜; 刘卫东; 李志伟; 付薪菱; 陈文奇

    2011-01-01

    苯并噻唑类杂环广泛应用于医药、农药、材料等领域,也是优良的有机合成分子构建切块.综述了近年来苯并噻唑类杂环合成方法的最近研究成果,特别是分子内氧化环合、金属催化环合等有效新方法.%Benzothiazoles have been widely used in pharmaceuticals,pesticides and engineering materials etc. They are also excellent organic molecular building blocks. The recent achievements in the synthesis of benzothiazoles were reviewed, especially the routes including effective intramolecular oxidative cyclization and metal-catalyzed cyclization.

  8. Anchoring of Cu(II) onto surface of porous metal-organic framework through post-synthesis modification for the synthesis of benzimidazoles and benzothiazoles

    Science.gov (United States)

    Kardanpour, Reihaneh; Tangestaninejad, Shahram; Mirkhani, Valiollah; Moghadam, Majid; Mohammadpoor-Baltork, Iraj; Zadehahmadi, Farnaz

    2016-03-01

    Efficient synthesis of various benzimidazoles and benzothiazoles under mild conditions catalyzed by Cu(II) anchored onto UiO-66-NH2 metal organic framework is reported. In this manner, first, the aminated UiO-66 was modified with thiophene-2-carbaldehyde and then the prepared Schiff base was reacted with CuCl2. The prepared catalyst was characterized by FT-IR, UV-vis, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), N2 adsorption, inductively coupled plasma atomic emission spectroscopy (ICP-AES) and field emission scanning electron microscopy (FE-SEM). The UiO-66-NH2-TC-Cu was applied as a highly efficient catalyst for synthesis of benzimidazole and benzothiazole derivatives by the reaction of aldehydes with 1,2-diaminobenzene or 2-aminothiophenol. The Cu(II)-containing MOF was reused several times without any appreciable loss of its efficiency.

  9. A polyamide receptor based benzothiazole derivative: highly selective and sensitive fluorescent sensor for Hg{sup 2+} ion in aqueous medium

    Energy Technology Data Exchange (ETDEWEB)

    Maity, Shubhra Bikash; Bharadwaj, Parimal K., E-mail: pkb@iitk.ac.in

    2015-05-15

    A water soluble benzothiazole derivative having polyamide arms has been designed and synthesized. The sensor selectively detects Hg{sup 2+} ion in aqueous medium in presence of alkali, alkaline earth, first row transition metal and heavy metal ions. The reversible behaviour of the sensor can be achieved in presence of iodide ion. - Highlights: • A benzothiazole derivative having polyamide arms has been designed and synthesized. • It selectively detects Hg{sup 2+} ion in presence of host of monovalent, divalent and trivalent ions in aqueous medium. • It works through a reversible way. • The detection limit for Hg{sup 2+} ion was found to be 7.15×10{sup −7} M.

  10. Rearrangement of 2-Benzothiazolylthioacetyl Hydrazide in Ethanol Solution of Potassium Hydroxide: Synthesis of s-Triazolo[3,4-b]benzothiazol-3-thiol and Its Derivatives

    Institute of Scientific and Technical Information of China (English)

    ZHANG,Yan(张艳); HUI,Xin-Ping(惠新平); DAI,Chao-Feng(戴朝峰); ZHANG,Zi-Yi(张自义); XU,Peng-Fei(许鹏飞)

    2002-01-01

    A novel rearrangement reaction about 2-benzothiazolylthioacetyl hydrazide (1) to produce s-triazolo[3,4-b]benzothiazol-3-thiol (3) in the presence of KOH and CS2 was described. Other way to synthesize 3 from 2-benzothiazolylhydrazine (2) under the same condition was compared and the Mannich reaction of compound 3 was reported too. Their structures were established by elemental analyses, IR, 1H NMR and MS spectra.

  11. Synthesis and X-ray diffraction study of palladium(II) 1,3-diphenyl-5-(benzothiazol-2-yl)formazanate

    Science.gov (United States)

    Zaĭdman, A. V.; Pervova, I. G.; Rezinskikh, Z. G.; Lipunov, I. N.; Slepukhin, P. A.

    2010-05-01

    The behavior of 1,3-diphenyl-5-(benzothiazol-2-yl)formazan as a bidentate ligand in the synthesis of the mononuclear palladium complex was investigated using slow diffusion. According to the X-ray diffraction study, the PdN4 coordination unit has a distorted square structure. The ligands form two six-membered chelate rings formed through the N1 and N4 atoms of the formazan fragment.

  12. Synthesis and X-ray diffraction study of palladium(II) 1,3-diphenyl-5-(benzothiazol-2-yl)formazanate

    Energy Technology Data Exchange (ETDEWEB)

    Zaidman, A. V., E-mail: biosphera@usfeu.ru; Pervova, I. G.; Rezinskikh, Z. G.; Lipunov, I. N. [Ural State Forest Engineering University (Russian Federation); Slepukhin, P. A., E-mail: slepukhin@ios.uran.ru [Russian Academy of Sciences, Postovsky Institute of Organic Synthesis, Ural Division (Russian Federation)

    2010-05-15

    The behavior of 1,3-diphenyl-5-(benzothiazol-2-yl)formazan as a bidentate ligand in the synthesis of the mononuclear palladium complex was investigated using slow diffusion. According to the X-ray diffraction study, the PdN4 coordination unit has a distorted square structure. The ligands form two six-membered chelate rings formed through the N1 and N4 atoms of the formazan fragment.

  13. Application of the SOS/umu test and high-content in vitro micronucleus test to determine genotoxicity and cytotoxicity of nine benzothiazoles.

    Science.gov (United States)

    Ye, Yan; Weiwei, Jiang; Na, Li; Mei, Ma; Kaifeng, Rao; Zijian, Wang

    2014-12-01

    Benzothiazole and benzothiazole derivatives (BTs) have been detected in various environmental matrices as well as in human beings, but little is currently available regarding their toxicities. In our study, genotoxicities of nine BTs (benzothiazole [BT], 2-chlorobenzothiazole [CBT], 2-bromobenzothiazole [BrBT], 2-fluorobenzothiazole [FBT], 2-methylbenzothiazole [MeBT], 2-mercaptobenzothiazole [MBT], 2-aminobenzothiazole [ABT], 2-hydroxy-benzothiazole [OHBT] and 2-methythiobenzothiazole [MTBT]) are comprehensively evaluated by the SOS/umu test using the bacterial Salmonella typhimurium TA1535/pSK1002 for DNA-damaging effect and the high content in vitro micronucleus test using two human carcinoma cells (MGC-803 and A549) for chromosome-damaging effect. The cytotoxicity of BTs on both bacteria and two human cells was also evaluated. Except for the cytotoxic effect of MBT on MGC-803 and A549, the other tested BTs showed more than 50% cytotoxicity at their highest concentrations in a dose-dependent manner, and their LC50s ranged from 19 (MBT in bacteria) to 270 mg l(-1) (CBT in A549). Activation and inactivation were observed for specific BTs after metabolism. On the other hand, no evidence of genotoxicity was obtained for BT, FBT and MBT, and DNA damage was induced by ABT, OHBT, BrBT and MTBT in MGC-803, by MeBT in A549 and by CBT in both cells. Through quantitative structure-activity relationship analysis, two structure alerts for chemical genotoxicity, including heterocyclic amine and hacceptor-path3-hacceptor are present in ABT and OHBT respectively; however, the underlying mechanisms still need further evaluation.

  14. Fate of linear alkylbenzenes and benzothiazoles of anthropogenic origin and their potential as environmental molecular markers in the Pearl River Delta, South China

    Energy Technology Data Exchange (ETDEWEB)

    Ni Honggang [State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640 (China); Graduate School, Chinese Academy of Sciences, Beijing 100049 (China); Shen Rulang [State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640 (China); Zeng Hui [Key Laboratory for Environmental and Urban Sciences, Shenzhen Graduate School, Peking University, Shenzhen 518055 (China); Zeng, Eddy Y., E-mail: eddyzeng@gig.ac.c [State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640 (China)

    2009-12-15

    The mass emissions of linear alkylbenzenes (LABs), benzothiazole (BT), and 2-[4-morpholinyl]benzothiazole (24MoBT) from anthropogenic activities within one year were estimated according to the population and the number of automobiles in the Pearl River Delta (PRD), South China. Based on the estimation, the distribution of these compounds among various environmental media was simulated with a mass balance box model established in the present study. The results showed that 79% of LABs generated in the PRD was stored in sediment while only 1.3% of LABs was presumably transported to the adjacent South China Sea (SCS). On the contrary, 47% of BT and 77% of 24MoBT generated in the region were carried with riverine runoff to the coastal ocean. The results from the present study suggest that hydrophobic compounds tend to stay in the watershed of the PRD, whereas hydrophilic ones mainly outflow to the coastal ocean. - A simple mass balance box model examines the fate of linear alkylbenzenes and benzothiazoles in the Pearl River Delta, South China.

  15. Synthesis and phase transition studies on non-symmetric liquid crystal dimers: N-(4-(n-(4-(benzothiazol-2-yl)phenoxy)alkyloxy)-benzylidene)-4-chloroanilines

    Science.gov (United States)

    Yeap, Guan-Yeow; Al-Taifi, Elham A.; Ong, Chin-Hin; Kamil Mahmood, Wan Ahmad; Takeuchi, Daisuke; Ito, Masato M.

    2012-06-01

    A new series of non-symmetric liquid crystal dimers N-(4-(n-(4-(benzothiazol-2-yl)phenoxy)alkyloxy)benzylidene)-4-chloroaniline containing benzothiazole and benzylideneimine units connected by a flexible alkyl spacer, -(CH2) n -, with n ranging from 4 to 12 in even parity have been prepared. All five members of this homologous series exhibit an enantiotropic nematic phase. The compounds with greater n of 8-12 exhibit both nematic and smectic phases upon cooling. A notable feature among this series is that for the member with n = 10, the smectic-nematic transition is also present. The nematic-isotropic transition temperatures and associated entropy changes with respect to all compounds in this series exhibit a dramatic dependence on the length of the flexible spacer. A comparison of the transitional properties of this series with those of α-(4-benzylidenechloroaniline-4‧-oxy)-ω-[4-(thiophene-2-carboxyl)benzylideneaniline-4‧-oxy]alkanes reveals that replacing benzothiazole moiety at one side of the flexible alkyl spacer reduces the nematic-isotropic transition temperature.

  16. In vitro DNA binding, pBR322 plasmid cleavage and molecular modeling study of chiral benzothiazole Schiff-base-valine Cu(II) and Zn(II) complexes to evaluate their enantiomeric biological disposition for molecular target DNA

    Science.gov (United States)

    Alizadeh, Rahman; Afzal, Mohd; Arjmand, Farukh

    2014-10-01

    Bicyclic heterocyclic compounds viz. benzothiazoles are key components of deoxyribonucleic acid (DNA) molecules and participate directly in the encoding of genetic information. Benzothiazoles, therefore, represent a potent and selective class of antitumor compounds. The design and synthesis of chiral antitumor chemotherapeutic agents of Cu(II) and Zn(II), L- and -D benzothiazole Schiff base-valine complexes 1a &b and 2a &b, respectively were carried out and thoroughly characterized by spectroscopic and analytical techniques. Interaction of 1a and b and 2a and b with CT DNA by employing UV-vis, florescence, circular dichroic methods and cleavage studies of 1a with pBR322 plasmid, molecular docking were done in order to demonstrate their enantiomeric disposition toward the molecular drug target DNA. Interestingly, these studies unambiguously demonstrated the greater potency of L-enantiomer in comparison to D-enantiomer.

  17. In vitro DNA binding, pBR322 plasmid cleavage and molecular modeling study of chiral benzothiazole Schiff-base-valine Cu(II) and Zn(II) complexes to evaluate their enantiomeric biological disposition for molecular target DNA.

    Science.gov (United States)

    Alizadeh, Rahman; Afzal, Mohd; Arjmand, Farukh

    2014-10-15

    Bicyclic heterocyclic compounds viz. benzothiazoles are key components of deoxyribonucleic acid (DNA) molecules and participate directly in the encoding of genetic information. Benzothiazoles, therefore, represent a potent and selective class of antitumor compounds. The design and synthesis of chiral antitumor chemotherapeutic agents of Cu(II) and Zn(II), L- and -D benzothiazole Schiff base-valine complexes 1a &b and 2a &b, respectively were carried out and thoroughly characterized by spectroscopic and analytical techniques. Interaction of 1a and b and 2a and b with CT DNA by employing UV-vis, florescence, circular dichroic methods and cleavage studies of 1a with pBR322 plasmid, molecular docking were done in order to demonstrate their enantiomeric disposition toward the molecular drug target DNA. Interestingly, these studies unambiguously demonstrated the greater potency of L-enantiomer in comparison to D-enantiomer.

  18. Synthesis and E/Z Configuration Determination of Novel Derivatives of 3-Aryl-2-(benzothiazol-2'-ylthio Acrylonitrile, 3-(Benzothiazol-2'-ylthio-4-(furan-2''-yl-3-buten-2-one and 2-(1-(Furan-2''-yl-3'-oxobut-1''-en-2-ylthio-3-phenylquinazolin-4(3H-one

    Directory of Open Access Journals (Sweden)

    Adel Abou El-Khair

    2011-07-01

    Full Text Available Knoevenagel condensation of 2-(benzothiazol-2-ylthio acetonitrile (2 with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a–b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c–e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a with either 1-(benzothiazol-2'-ylthio propan-2-one (5 or 2-(2'-oxo propylthio-3-phenyl-quinazolin-4(3H-one (9 leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, 1H-NMR and 13C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.

  19. A Comparative Study of the Inclusion Complexes of 2-[5'-benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole and 2-[5'-(p-N,N-dimethylamino- benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole withβ-Cyclodextrin

    Directory of Open Access Journals (Sweden)

    S. Panda

    2011-01-01

    Full Text Available The compounds 2-[5'-benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole and 2-[5'-(p-N,N-dimethylamino- benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole have been synthesized in their purest forms starting from 2-aminobenzothiazole. The inclusion complexes of the above compounds have been prepared with β-cyclodextrin to increase their solubility and bioaccessibility in polar medium. The formation of inclusion complexes have been ascertained by study of spectral characteristic before and after inclusion complex formation. The stability of inclusion complexes and nature of interaction between the host and guest are known from the determination of thermodynamic parameters. Further the antibacterial and antifungal activities of the compounds are determined which is found to increase significantly after inclusion complex formation

  20. Third-Order Optical Nonlinearities of Squarylium Dyes with Benzothiazole Donor Groups Measured Using the Picosecond Z-Scan Technique

    Science.gov (United States)

    Li, Zhong-Yu; Xu, Song; Chen, Zi-Hui; Zhang, Fu-Shi; Kasatani, Kazuo

    2011-08-01

    Third-order optical nonlinearities of two squarylium dyes with benzothiazole donor groups (BSQ1 and BSQ2) in chloroform solution are measured by a picosecond Z-scan technique at 532 nm. It is found that the two compounds show the saturation absorption and nonlinear self-focus refraction effect. The molecular second hyperpolarizabilities are calculated to be 7.46 × 10-31 esu and 5.01 × 10-30 esu for BSQ1 and BSQ2, respectively. The large optical nonlinearities of squarylium dyes can be attributed to their rigid and intramolecular charge transfer structure. The difference in γ values is attributed to the chloro group of benzene rings of BSQ2 and the one-photon resonance effect. It is found that the third-order nonlinear susceptibilities of two squarylium dyes are mainly determined by the real parts of χ(3), and the large optical nonlinearities of studied squarylium dyes can be attributed to the nonlinear refraction.

  1. TD-DFT Study of Absorption and Emission Spectra of 2-(2'-Aminophenyl)benzothiazole Derivatives in Water.

    Science.gov (United States)

    Manojai, Natthaporn; Daengngern, Rathawat; Kerdpol, Khanittha; Kungwan, Nawee; Ngaojampa, Chanisorn

    2017-03-01

    Reduction of aromatic azides to amines is an important property of hydrogen sulphide (H2S) which is useful in fluorescence microscopy and H2S probing in cells. The aim of this work is to study the substituent effect on the absorption and emission spectra of 2-(2'-aminophenyl)benzothiazole (APBT) in order to design APBT derivatives for the use of H2S detection. Absorption and emission spectra of APBT derivatives in aqueous environment were calculated using density functional theory (DFT) and time-dependent DFT (TD-DFT) at B3LYP/6-311+G(d,p) level. The computed results favoured the substitution of strong electron-donating group on the phenyl ring opposite to the amino group for their large Stokes' shifts and emission wavelengths of over 600 nm. Also, three designed compounds were suggested as potential candidates for the fluorescent probes. Such generalised guideline learnt from this work can also be useful in further designs of other fluorescent probes of H2S in water.

  2. Third-Order Optical Nonlinearities of Squarylium Dyes with Benzothiazole Donor Groups Measured Using the Picosecond Z-Scan Technique

    Institute of Scientific and Technical Information of China (English)

    LI Zhong-Yu; XU Song; CHEN Zi-Hui; ZHANG Fu-Shi; KASATANI Kazuo

    2011-01-01

    @@ Third-order optical nonlinearities of two squarylium dyes with benzothiazole donor groups (BSQ1 and BSQ2)in chloroform solution are measured by a picosecond Z-scan technique at 532 nm.It is found that the two compounds show the saturation absorption and nonlinear self-focus refraction effect.The molecular second hyperpolarizabilities are calculated to be 7.46×10-31 esu and 5.01×10-30 esu for BSQ1 and BSQ2, respectively.The large optical nonlinearities of squarylium dyes can be attributed to their rigid and intramolecular charge transfer structure.The difference in γvalues is attributed to the chloro group of benzene rings of BSQ2 and the one-photon resonance effect.It is found that the third-order nonlinear susceptibilities of two squarylium dyes are mainly determined by the real parts of X(3), and the large optical nonlinearities of studied squarylium dyes can be attributed to the nonlinear refraction.

  3. Antitumor and antimetastatic activities of a novel benzothiazole-2-thiol derivative in a murine model of breast cancer.

    Science.gov (United States)

    Hu, XiaoLin; Li, Sen; He, Yan; Ai, Ping; Wu, Shaoyong; Su, Yonglin; Li, Xiaolin; Cai, Lei; Peng, Xingchen

    2017-01-02

    The prognosis of metastatic breast cancer is always very poor. Thus, it is urgent to develop novel drugs with less toxicity against metastatic breast cancer. A new drug (XC-591) derived from benzothiazole-2-thiol was designed and synthesized in our lab. In this study, we tried to assess effects of XC-591 treatment on primary breast cancer and pulmonary metastasis in 4T1 mice model. Furthermore, we tried to discover its possible molecular mechanism of action. MTT experiment showed XC-591 had significant anti-cancer activity on diverse cancer cells. Furthermore, XC-591 significantly suppressed the proliferation of 4T1 cells by colony formation assay. The in vivo results displayed that XC-591 could inhibit the growth and metastasis in 4T1 model. Moreover, histological analysis revealed that XC-591 treatment increased apoptosis, inhibited proliferation and angiogenesis in vivo. In addition, XC-591 did not contribute to obvious drug associated toxicity during the whole study. Molecular mechanism showed XC-591 could inhibit RhoGDI, activate caspase-3 and decrease phosphorylated Akt. The present data may be important to further explore this kind of new small-molecule inhibitor.

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

    Science.gov (United States)

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

    2012-05-01

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

  5. Synthesis and anticancer activity of novel benzimidazole and benzothiazole derivatives against HepG2 liver cancer cells.

    Science.gov (United States)

    Youssef, Amal M; Malki, Ahmed; Badr, Mona H; Elbayaa, Rasha Y; Sultan, Ahmed S

    2012-03-01

    Most of cancer chemotherapeutics and chemopreventives exert their effects by triggering apoptotic cell death. In this study, novel benzimidazole and benzothiazole derivatives have been synthesized to investigate their effects on HepG2 liver cancer cell lines after initial screening study. A dose response curve was constructed and the most active derivatives were further studied for apoptotic analysis. Six active benzimidazole derivatives (8, 9, 10, 12, 13 and 14) significantly induced apoptosis compared to control group. Two compounds 10 and 12 induced apoptosis by arresting cells in G1 phase of cell cycle which is confirmed by increased expression level of p21. The activity of caspase-3 which is well known as one of the key executioners of apoptosis was determined in the presence and absence of the tested derivatives. Our results indicated that compounds 10 and 12 significantly increased caspase-3 activity compared to control group. Moreover, a docked pose of compounds 10 and 12 was obtained bound to caspase-3 active site using Molecular Operating Environment module. This study demonstrated that benzimidazole derivatives 10 and 12 provoke cytotoxicity and induced apoptosis in liver cancer cells HepG2.

  6. Pharmacophore modeling and 3D-QSAR studies on substituted benzothiazole / benzimidazole analogues as DHFR inhibitors with antimycobacterial activity

    Directory of Open Access Journals (Sweden)

    R. Priyadarsini

    2012-08-01

    Full Text Available The resurgence of tuberculosis and the emergence of multidrug-resistant strains of Mycobacteria drugs has propelled the development of new structural classes of antitubercular agents. The present study was undertaken to investigate the opportunities which the enzyme dihydrofolate reductase, a promising drug target for treatmentof Mycobacterial infections offers for the development of new TB drugs. Pharmacophore models were established by using the HipHop and HypoGen algorithms implemented in the Catalyst software package. Thebest quantitative pharmacophore model, consisted of two hydrogen bond acceptor, a hydrophobic aliphatic, and a ring aromatic feature which has the highest correlation coefficient (0.93, as well as enrichment factor of 1.75 and Goodness of hit score of 0.73. Based on the pharmacophore model some leads were optimized and some of its derivatives were synthesized and analysed by following QSAR studies. About 25 compounds of substituted benzothiazole/ benzimidazole derivatives were synthesized as potent DHFR inhibitors and screened for antimycobacterial activity. To further explore the structure-activity relationships of all newly synthesized compounds, 3D-QSAR analyses were developed. MFA studies were performed with the QSAR module of Cerius2 using genetic partial least squares (G/PLS algorithm. The predictive ability of the developed model was assessed using a training set of 25 and a test set of 5 compounds (r2pred = 0.924.The analyzed MF

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

    Directory of Open Access Journals (Sweden)

    Li Yang

    2012-01-01

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

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

    Science.gov (United States)

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

    2012-01-17

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

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

    Institute of Scientific and Technical Information of China (English)

    周晓玉; 陈霞; 杨发旺; 刘义龙; 令狐克美

    2016-01-01

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

  10. Combined drug action of 2-phenylimidazo[2,1-b]benzothiazole derivatives on cancer cells according to their oncogenic molecular signatures.

    Directory of Open Access Journals (Sweden)

    Alessandro Furlan

    Full Text Available The development of targeted molecular therapies has provided remarkable advances into the treatment of human cancers. However, in most tumors the selective pressure triggered by anticancer agents encourages cancer cells to acquire resistance mechanisms. The generation of new rationally designed targeting agents acting on the oncogenic path(s at multiple levels is a promising approach for molecular therapies. 2-phenylimidazo[2,1-b]benzothiazole derivatives have been highlighted for their properties of targeting oncogenic Met receptor tyrosine kinase (RTK signaling. In this study, we evaluated the mechanism of action of one of the most active imidazo[2,1-b]benzothiazol-2-ylphenyl moiety-based agents, Triflorcas, on a panel of cancer cells with distinct features. We show that Triflorcas impairs in vitro and in vivo tumorigenesis of cancer cells carrying Met mutations. Moreover, Triflorcas hampers survival and anchorage-independent growth of cancer cells characterized by "RTK swapping" by interfering with PDGFRβ phosphorylation. A restrained effect of Triflorcas on metabolic genes correlates with the absence of major side effects in vivo. Mechanistically, in addition to targeting Met, Triflorcas alters phosphorylation levels of the PI3K-Akt pathway, mediating oncogenic dependency to Met, in addition to Retinoblastoma and nucleophosmin/B23, resulting in altered cell cycle progression and mitotic failure. Our findings show how the unusual binding plasticity of the Met active site towards structurally different inhibitors can be exploited to generate drugs able to target Met oncogenic dependency at distinct levels. Moreover, the disease-oriented NCI Anticancer Drug Screen revealed that Triflorcas elicits a unique profile of growth inhibitory-responses on cancer cell lines, indicating a novel mechanism of drug action. The anti-tumor activity elicited by 2-phenylimidazo[2,1-b]benzothiazole derivatives through combined inhibition of distinct effectors in

  11. Insight into the Amino-Type Excited-State Intramolecular Proton Transfer Cycle Using N-Tosyl Derivatives of 2-(2'-Aminophenyl)benzothiazole.

    Science.gov (United States)

    Chen, Chi-Lin; Tseng, Huan-Wei; Chen, Yi-An; Liu, Jun-Qi; Chao, Chi-Min; Liu, Kuan-Miao; Lin, Tzu-Chieh; Hung, Cheng-Hsien; Chou, Yen-Lin; Lin, Ta-Chun; Chou, Pi-Tai

    2016-02-25

    Studies have been carried out to gain insight in to an overall excited-state proton transfer cycle for a series of N-tosyl derivatives of 2-(2'-aminophenyl)benzothiazole. The results indicate that followed by ultrafast (benzothiazole (PBT-NHTs) the subsequent cis-trans isomerization process in both triplet and ground states are probed by nanosecond transient absorption (TA) and two-step laser-induced fluorescence (TSLIF) spectroscopy. Both TA and TSLIF results indicate the existence of a long-lived trans-tautomer species in the ground state with a lifetime of few microseconds. The experimental results correlate well with the theoretical approach, which suggests that PBT-NHTs proton transfer tautomer generated in the excited state undergoes intramolecular C1-C1' rotation to ∼100° between benzothiazole and phenyl moieties in which the energetics for the S1 and T1 states are nearly identical. As a result, the intersystem crossing between S1 and T1 states serves as a fast deactivation pathway for the excited-state cis-tautomer to channel into both cis- and trans-tautomer in their respective T1 states, followed by the dominant T1-S0 radiationless deactivation to populate the trans-tautomer in the ground state. The trans-tautomer species in the S0 state proceeds with intermolecular double proton transfer to regenerate the cis-normal form. An overall proton-transfer cycle describing the amino-type ESIPT and the subsequent isomerization processes is thus depicted in detail.

  12. A 2-(2'-hydroxyphenyl)benzothiazole (HBT)-quinoline conjugate: a highly specific fluorescent probe for Hg(2+) based on ESIPT and its application in bioimaging.

    Science.gov (United States)

    Sahana, Sunanda; Mishra, Gargi; Sivakumar, Sri; Bharadwaj, Parimal K

    2015-12-14

    A benzothiazole derived chemosensor L has been designed based on the excited-state intramolecular proton transfer (ESIPT) mechanism to afford a fluorescence turn-on response specifically in the presence of Hg(2+) ions over a host of biologically relevant metal ions as well as toxic heavy metal ions. The chemosensor exhibits high sensitivity with the detection limit down to 0.11 μM. The metal binding is supported by (1)H NMR titrations, ESI-MS spectral analysis and substantiated by theoretical calculations using the density functional theory. The probe shows cell membrane permeability and efficiency for the detection of Hg(2+) in HeLa cells.

  13. S-1,3-Benzothiazol-2-yl (2Z-2-(2-amino-1,3-thiazol-4-yl-2-(methoxyiminoethanethioate

    Directory of Open Access Journals (Sweden)

    Shahzad Sharif

    2009-08-01

    Full Text Available The title compound, C13H10N4O2S3, is an acylating agent which belongs to the thiazole class of organic compounds. The dihedral angle between the benzene and thiazole rings, which are fused to each other, is 1.2 (2° so the overall benzothiazole system is almost planar. Intermolecular N—H...N interactions and weak C—H...O interactions between symmetry-related molecules stabilize the crystal structure, forming three different ring motifs [R22(8, R22(10 and R22(16] in three dimensions.

  14. Lipophilicity determination of N-( benzothiazol-2-yl )-α-amino alkyl phosphonic diesters by RP-HPLC and RP-HPTLC

    Institute of Scientific and Technical Information of China (English)

    张玲; 李在国; 黄润秋; 王琴孙

    2000-01-01

    Using methanol-water mixtures as the mobile phase, the chromatographic retebtion parameters k' and R1 were determ1ined by reversed-phase high-perfor mance liquid chromatography (RP-HPLC) and reversed-phase high-performance thin-layer chromatograhy (RP-HPILC) for N-(benzothiazol-2-yl)-α-amino alkyl phosphonic diesters and the correlation with lipophilicity parameter (ClogP) was established. Logk wues obtained from RP-HPLC and Rmo values obtained from RP-HPTLC can be used to evaluate the lipophilicity of this kind of compounds. Chromatographic method is a good alternaive for lipophilicity measurement.

  15. Crystal structure of ethyl 4-(2-chlorophenyl-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Balbir Kumar

    2015-09-01

    Full Text Available In the title compound, C20H17ClN2O2S, the dihedral angle between the planes of the benzothiazole fused ring system (r.m.s. deviation = 0.024 Å and the chlorobenzene ring is 89.62 (12°. The ester C—O—C—C side chain has an anti orientation [torsion angle = −155.2 (3°]. In the crystal, weak aromatic π–π stacking interactions are observed between the phenyl and pyrimidine rings [centroid–centroid seperation = 3.666 (2 Å].

  16. A rhodamine-benzothiazole conjugated sensor for colorimetric, ratiometric and sequential recognition of copper(II) and sulfide in aqueous media

    Science.gov (United States)

    Tang, Lijun; Dai, Xin; Wen, Xin; Wu, Di; Zhang, Qiang

    2015-03-01

    A new rhodamine-benzothiazole conjugated colorimetric sensor 1 that exhibits sequential recognition to Cu2+ and S2- in CH3CN/HEPES buffer (v/v = 1:1, HEPES 10 mM, pH = 7.0) solution has been developed. Sensor 1 displays highly selective and sensitive recognition to Cu2+ with a ratiometric behavior, and the resultant 1-Cu2+ complex can act as a highly selective S2- sensor via Cu2+ displacement approach. The Cu2+ and S2- recognition processes are rapid and reversible, and the Cu2+ and S2- inputs can result in an INHIBIT logic gate.

  17. 2-取代苯并噻唑类衍生物合成方法研究的新进展%New Progress in the Synthesis of 2-Substituent-Benzothiazole Derivatives

    Institute of Scientific and Technical Information of China (English)

    竺宁; 张志伟; 高敏; 韩利民; 索全伶; 洪海龙

    2013-01-01

    2-取代苯并噻唑类衍生物在工业、农业、医药等领域有广泛的应用前景,因此这类衍生物合成的新方法备受关注.笔者以邻氨基苯硫酚、芳香邻氨基二硫化物、硫代酰胺、硫脲与邻卤苯胺等反应原料为基础,从引入硫原子的方法及反应机理的角度综述了近几年合成2-取代苯并噻唑类衍生物的新方法.%2-Substituent-benzothiazole derivatives could be widely used in the field of industry,agriculture and medicine.So much attention to the synthetic methods for the synthesis of the benzothiazole derivatives has been attracted and many novel synthetic methods have been developed in recent years.In this review,based on the starting material of 2-aminobenzenethiol,aromatic disulfides,thioformanilides,N-arylthiourea and o-haloaniline,the new synthetic methods for the preparation of the benzothiazole derivatives have been summarized from the introducing methods of the sulfur atom and the reaction mechanism for the formation of benzothiazole derivatives.

  18. Solvent-dependent excited-state hydrogen transfer and intersystem crossing in 2-(2′-hydroxyphenyl)-benzothiazole

    KAUST Repository

    Aly, Shawkat Mohammede

    2015-02-12

    The excited-state intramolecular hydrogen transfer (ESIHT) of 2-(2′-hydroxyphenyl) benzothiazole (HBT) has been investigated in a series of nonpolar, polar aprotic, and polar protic solvents. A variety of state-of-the-art experimental methods were employed, including femto- and nanosecond transient absorption and fluorescence upconversion spectroscopy with broadband capabilities. We show that the dynamics and mechanism of ESIHT of the singlet excited HBT are strongly solvent-dependent. In nonpolar solvents, the data demonstrate that HBT molecules adopt a closed form stabilized by O-H⋯N chelated hydrogen bonds with no twisting angle, and the photoinduced H transfer occurs within 120 fs, leading to the formation of a keto tautomer. In polar solvents, owing to dipole-dipole cross talk and hydrogen bonding interactions, the H transfer process is followed by ultrafast nonradiative deactivation channels, including ultrafast internal conversion (IC) and intersystem crossing (ISC). This is likely to be driven by the twisting motion around the C-C bond between the hydroxyphenyl and thiazole moieties, facilitating the IC back to the enol ground state or to the keto triplet state. In addition, our femtosecond time-resolved fluorescence experiments indicate, for the first time, that the lifetime of the enol form in ACN is approximately 280 fs. This observation indicates that the solvent plays a crucial role in breaking the H bond and deactivating the excited state of the HBT. Interestingly, the broadband transient absorption and fluorescence up-conversion data clearly demonstrate that the intermolecular proton transfer from the excited HBT to the DMSO solvent is about 190 fs, forming the HBT anion excited state.

  19. Design, Synthesis and Biological Evaluation of Novel Rapamycin Benzothiazole Hybrids as mTOR Targeted Anti-cancer Agents.

    Science.gov (United States)

    Xie, Lijun; Huang, Jie; Chen, Xiaoming; Yu, Hui; Li, Kualiang; Yang, Dan; Chen, Xiaqin; Ying, Jiayin; Pan, Fusheng; Lv, Youbing; Cheng, Yuanrong

    2016-01-01

    The immunosuppressant drug rapamycin, was firstly identified as a mammalian target of rapamycin (mTOR) allosteric inhibitor, and its derivatives have been successfully developed as anti-cancer drugs. Therefore, finding rapamycin derivatives with better anti-cancer activity has been proved to be an effective way to discover new targeted anti-cancer drugs. In this paper, structure modification was performed at the C-43 position of rapamycin using bioisosterism and a hybrid approach: a series of novel rapamycin-benzothiazole hybrids 4a-e, 5a-c, and 9a, b have been designed, synthesized and evaluated for their anti-cancer activity against Caski, CNE-2, SGC-7901, PC-3, SK-NEP-1 and A-375 human cancer cell lines. Some of these compounds (4a-e, 9a, b) displayed good to excellent potency against the Caski and SK-NEP-1 cell line as compared with rapamycin. Compound 9b as the most active compound showed IC50 values of 8.3 (Caski) and 9.6 μM (SK-NEP-1), respectively. In addition, research on the mechanism showed that 9b was able to cause G1 phase arrest and induce apoptosis in the Caski cell line. Most importantly, it significantly decreased the phosphorylation of S6 ribosomal protein, p70S6K1 and 4EBP1, which indicated that 9b inhibited the cancer cell growth by blocking the mTOR pathway and may have the potential to become a new mTOR inhibitor.

  20. 一种合成苯并噻唑类衍生物的新方法%A New Approach to Prepare Benzothiazoles

    Institute of Scientific and Technical Information of China (English)

    余永强; 倪沛洲; 陆涛

    2007-01-01

    Benzothiazole derivatives have been drawing great attention due to their antimalarial and antitumor properties. We reported a new approach to prepare benzothiazoles: condensation of thioethylbenzoate with 2-aminothiophenols. The operation is convenient and the reaction proceeds in mild condition. Six compounds in good yields were synthesized by this method.%苯并噻唑及其衍生物由于其独特的抗感染和抗肿瘤的特性,近年来引起广泛关注.本文报导了一种新的合成苯并噻唑类衍生物的方法:硫代苯甲酸乙酯与邻氨基疏基取代苯的缩合.这种方法操作简便,反应条件温和.尤其适合于底物有活泼官能团的情况.应用此方法,高收率合成了六个化合物.

  1. Discovery of a selective kinase inhibitor (TAK-632) targeting pan-RAF inhibition: design, synthesis, and biological evaluation of C-7-substituted 1,3-benzothiazole derivatives.

    Science.gov (United States)

    Okaniwa, Masanori; Hirose, Masaaki; Arita, Takeo; Yabuki, Masato; Nakamura, Akito; Takagi, Terufumi; Kawamoto, Tomohiro; Uchiyama, Noriko; Sumita, Akihiko; Tsutsumi, Shunichirou; Tottori, Tsuneaki; Inui, Yoshitaka; Sang, Bi-Ching; Yano, Jason; Aertgeerts, Kathleen; Yoshida, Sei; Ishikawa, Tomoyasu

    2013-08-22

    With the aim of discovering a selective kinase inhibitor targeting pan-RAF kinase inhibition, we designed novel 1,3-benzothiazole derivatives based on our thiazolo[5,4-b]pyridine class RAF/VEGFR2 inhibitor 1 and developed a regioselective cyclization methodology for the C-7-substituted 1,3-benzothiazole scaffold utilizing meta-substituted anilines. Eventually, we selected 7-cyano derivative 8B (TAK-632) as a development candidate and confirmed its binding mode by cocrystal structure with BRAF. Accommodation of the 7-cyano group into the BRAF-selectivity pocket and the 3-(trifluoromethyl)phenyl acetamide moiety into the hydrophobic back pocket of BRAF in the DFG-out conformation contributed to enhanced RAF potency and selectivity vs VEGFR2. Reflecting its potent pan-RAF inhibition and slow off-rate profile, 8B demonstrated significant cellular activity against mutated BRAF or mutated NRAS cancer cell lines. Furthermore, in both A375 (BRAF(V600E)) and HMVII (NRAS(Q61K)) xenograft models in rats, 8B demonstrated regressive antitumor efficacy by twice daily, 14-day repetitive administration without significant body weight loss.

  2. Removal of cations using ion-binding terpolymer involving 2-amino-6-nitro-benzothiazole and thiosemicarbazide with formaldehyde by batch equilibrium technique

    Energy Technology Data Exchange (ETDEWEB)

    Ahamed, Mohamed A. Riswan [Department of Chemistry, Oxford Engineering College, Tiruchirappalli 620 009, Tamil Nadu (India); Jeyakumar, Duraisamy [Functional Materials Division, Central Electrochemical Research Institute, Karaikudi 630 006, Tamil Nadu (India); Burkanudeen, Abdul R., E-mail: a_deen@rediffmail.com [PG and Research Department of Chemistry, Jamal Mohamed College, Tiruchirappalli 620 020, Tamil Nadu (India)

    2013-03-15

    Graphical abstract: Effect of (a) NaCl, (b) NaNO{sub 3}, (c) NaClO{sub 4} and (d) Na{sub 2}SO{sub 4} electrolytes on metal ion uptake. Display Omitted Highlights: ► A novel [(2-amino-6-nitro-benzothiazole)–thiosemicarbazide–formaldehyde] terpolymer has been synthesized. ► SEM images show high porosity in the surface of the resin evidences the effective adsorption of various metal ions. ► BTF terpolymer is a well recyclable cation-exchange resin for industrial waste water treatment. -- Abstract: 2-Amino-6-nitro-benzothiazole and thiosemicarbazide with formaldehyde (BTF) terpolymer was synthesized by the condensation polymerization technique. The elemental analysis and physico-chemical parameters of the terpolymer were measured. This chelation terpolymer was characterized by infrared, electronic and nuclear magnetic resonance ({sup 1}H and {sup 13}C NMR) spectral studies. The molecular weight of the terpolymer was determined by gel permeation chromatography (GPC). Surface analysis of the terpolymer was analyzed by scanning electron microscopy (SEM) and X-ray diffraction (XRD) method. The thermal stability of the terpolymer was analyzed by thermogravimetric analysis (TGA). The cation-exchange property of the terpolymer was determined by batch equilibrium method with the effect of pH, contact time and electrolytes. The reusability of the resin was also studied to estimate the effectiveness of the terpolymer resin.

  3. A novel benzothiazole derivative YLT322 induces apoptosis via the mitochondrial apoptosis pathway in vitro with anti-tumor activity in solid malignancies.

    Science.gov (United States)

    Xuejiao, Song; Yong, Xia; Ningyu, Wang; Lidan, Zhang; Xuanhong, Shi; Youzhi, Xu; Tinghong, Ye; Yaojie, Shi; Yongxia, Zhu; Luoting, Yu

    2013-01-01

    Benzothiazole derivatives are known for various biological activities, and their potency in cancer therapy has received considerable attention in recent years. YLT322, a novel synthesized benzothiazole derivative, exhibits potent anti-tumor activity via inducing apoptosis both in vitro and in vivo. In this study, we found that YLT322 showed growth inhibition against a broad spectrum of human cancer cells and induced apoptosis of HepG2 cells in a dose- and time-dependent manner. The occurrence of its apoptosis was associated with activation of caspases-3 and -9, but not caspase-8. YLT322 increased the expression of Bax, decreased the expression of Bcl-2, and induced the release of cytochrome c which activates the mitochondrial apoptotic pathway. The down-regulation of phosphorylated p42/44 MAPK and phosphorylated Akt was also observed. Moreover, YLT322 suppressed the growth of established tumors in xenograft models in mice without obvious side effects. Histological and immunohistochemical analyses revealed an increase in TUNEL and caspase-3-positive cells and a decrease in Ki67-positive cells upon YLT322. These results suggest that YLT322 may be a potential candidate for cancer therapy.

  4. Synthesis, Characterization and Antibacterial Studies of N-(Benzothiazol-2-yl-4-chlorobenzenesulphonamide and Its Neodymium(III and Thallium(III Complexes

    Directory of Open Access Journals (Sweden)

    Lawrence Nnamdi Obasi

    2017-02-01

    Full Text Available N-(Benzothiazol-2-yl-4-chlorobenzenesulphonamide (NBTCS was synthesized by condensation reaction of 4-chlorobenzenesulphonyl chloride and 2-aminobenzothiazole in acetone under reflux. Neodymium(III and thallium(III complexes of the ligand were also synthesized. Both ligand and metal complexes were characterized using UV-Vis, IR, 1H- and 13C-NMR spectroscopies, elemental analysis and molar conductance measurement. IR studies revealed that the ligand is tridentate and coordinates to the metal ions through nitrogen and oxygen atoms of the sulphonamide group and nitrogen atom attached to benzothiazole ring. The neodymium(III complex displays a coordination number of eight while thallium(III complex displays a coordination number of six. The ligand and its complexes were screened in vitro for their antibacterial activities against Escherichia coli strains (E. coli 6 and E. coli 13, Proteus species, Staphylococcus aureus and Pseudomonas aeruginosa using the agar well diffusion technique. The synthesized compounds were found to be more active against the microorganisms screened relative to ciprofloxacin, gentamicin and co-trimoxazole.

  5. Inhibition of TNF-{alpha}-mediated inflammatory responses by a benzodioxolylacetylamino-linked benzothiazole analog in human fibroblast-like synoviocytes

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Young-Rae [Department of Biochemistry, Research Institute for Endocrine Sciences and Diabetes Research Center, Chonbuk National University Medical School, Jeonju, Jeonbuk 561-756 (Korea, Republic of); Jin, Guo Hua [College of Pharmacy, Sookmyung Women' s University, 52 Hyochangwon-gil, Yongsan-gu, Seoul 140-742 (Korea, Republic of); Lee, Sang-Myeong [Division of Biotechnology, College of Environmental and Bioresource Sciences, Chonbuk National University, Iksan, Jeonbuk 570-752 (Korea, Republic of); Park, Jin-Woo [Department of Biochemistry, Research Institute for Endocrine Sciences and Diabetes Research Center, Chonbuk National University Medical School, Jeonju, Jeonbuk 561-756 (Korea, Republic of); Ryu, Jae-Ha [College of Pharmacy, Sookmyung Women' s University, 52 Hyochangwon-gil, Yongsan-gu, Seoul 140-742 (Korea, Republic of); Jeon, Raok, E-mail: rjeon@sm.ac.kr [College of Pharmacy, Sookmyung Women' s University, 52 Hyochangwon-gil, Yongsan-gu, Seoul 140-742 (Korea, Republic of); Park, Byung-Hyun, E-mail: bhpark@jbnu.ac.kr [Department of Biochemistry, Research Institute for Endocrine Sciences and Diabetes Research Center, Chonbuk National University Medical School, Jeonju, Jeonbuk 561-756 (Korea, Republic of)

    2011-05-20

    Highlights: {yields} We synthesized SPA0537, a benzothiazole analog. {yields} SPA0537 is a potent NF-{kappa}B inhibitor. {yields} SPA0537 suppresses the production of proinflammatory mediators in human rheumatoid fibroblast-like synoviocytes. {yields} SPA0537 is effective at suppressing osteoclast differentiation. -- Abstract: The pathologic processes of rheumatoid arthritis are mediated by a number of cytokines, chemokines, and matrix metalloproteinases, the expressions of which are controlled by NF-{kappa}B. This study was performed to explore the effects of a benzothiazole analog, SPA0537, on the control of the NF-{kappa}B activation pathway. We also investigated whether SPA0537 had any anti-inflammatory effects in human rheumatoid fibroblast-like synoviocytes (FLS). SPA0537 inhibited the nuclear translocation and the DNA binding of NF-{kappa}B subunits, which correlated with the inhibitory effects on IKK phosphorylation and I{kappa}B{alpha} degradation in TNF-{alpha}-stimulated rheumatoid FLS. These events further suppressed chemokine production, matrix metalloproteinase secretion, and TNF-{alpha}-induced cell proliferation. In addition, SPA0537 inhibited the osteoclast differentiation induced by macrophage colony-stimulating factor (MCSF) and receptor activator of the NF-{kappa}B ligand (RANKL) in bone marrow macrophages. These findings suggest that SPA0537 exerts anti-inflammatory effects in rheumatoid FLS through the inhibition of the NF-{kappa}B pathway. Therefore, it may have therapeutic value for the treatment of rheumatoid arthritis.

  6. catena-Poly[bis(1,3-benzothiazol-3-ium [[dichloridoantimonate(III]-di-μ-chlorido-μ-oxido-[chloridoantimonate(III]-μ-chlorido

    Directory of Open Access Journals (Sweden)

    Oussama Chebout

    2016-02-01

    Full Text Available The title compound, {(C7H6NS2[Sb2Cl6O]}n, contains two benzothiazolidium cations and one tri-μ-chlorido-trichlorido-μ-oxido-diantimonate(III anion. The structure of the inorganic cation may be described as as being built up from two polyhedra, i.e. a square-pyramidal SbCl4O and a distorted octahedral SbOCl5 unit, sharing a common face (comprising the O atom and two Cl atoms. The two benzothiazole cations are quasi-planar and subtend a dihedral angle of 19.93 (5°. The crystal packing can be described by alternating (100 layers and [001] chains of the organic cations and inorganic anions connected through an extensive three-dimensional network of N—H...Cl, C—H...O and C—H...Cl hydrogen bonds. This is consolidated by slipped π–π stacking, with centroid-to-centroid distances between the benzothiazole rings of 3.7111 (18–3.8452 (16 Å. These interactions link the molecules within the layers and also link the layers together and reinforce the cohesion of the ionic structure.

  7. Micro-Raman, Mid-IR, Far-IR and DFT studies on 2-[4-(4-Fluorobenzamido)phenyl]benzothiazole

    Science.gov (United States)

    Unsalan, O.; Sert, Y.; Ari, H.; Simão, A.; Yilmaz, A.; Boyukata, M.; Bolukbasi, O.; Bolelli, K.; Yalcin, I.

    Molecular structure of 2-[4-(4-Fluorobenzamido)phenyl]benzothiazole was determined by quantum chemical calculations. MidIR and FarIR spectra were recorded at room temperature, with 4 cm-1 resolution in the 4000-400 cm-1 and 700-30 cm-1 regions, respectively for the first time. Raman spectrum was recorded in the 4000-100 cm-1 range. Optimized molecular structure and vibrational wavenumbers of the compound in its ground state have been calculated by using Density Functional Theory using B3LYP functional with 6-311++G(d,p) basis set. Vibrational wavenumbers were seen to be in good agreement with the experimental IR data. Furthermore, assignments of each vibrational mode were interpreted in terms of potential energy distributions in detail.

  8. Designing, synthesis of selective and high-affinity chalcone-benzothiazole hybrids as Brugia malayi thymidylate kinase inhibitors: In vitro validation and docking studies.

    Science.gov (United States)

    Sashidhara, Koneni V; Avula, Srinivasa Rao; Doharey, Pawan Kumar; Singh, L Ravithej; Balaramnavar, Vishal M; Gupta, Jyoti; Misra-Bhattacharya, Shailja; Rathaur, Sushma; Saxena, Anil K; Saxena, Jitendra Kumar

    2015-10-20

    In our continuing search for safe and efficacious antifilarials, a series of novel chalcone-benzothiazole hybrids have been synthesized and evaluated for their Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition activity. Their selectivity towards BmTMK was studied and compared to the human TMK (HsTMK) by an in silico method. Out of seventeen derivatives, compounds 34 and 42 showed higher interactions with the BmTMK active site. MolDock docking model revealed the interactions of these two derivatives and the results corroborated well with their in vitro antifilarial activities. Our studies suggest that these hybrids are selective towards the BmTMK enzyme and may serve as potential therapeutic agents against filariasis.

  9. SKLB-163, a new benzothiazole-2-thiol derivative, exhibits potent anticancer activity by affecting RhoGDI/JNK-1 signaling pathway.

    Science.gov (United States)

    Peng, X; Xie, G; Wang, Z; Lin, H; Zhou, T; Xiang, P; Jiang, Y; Yang, S; Wei, Y; Yu, L; Zhao, Y

    2014-03-27

    Small-molecule inhibitors are an attractive therapeutic approach for most types of human cancers. SKLB-163, a novel benzothiazole-2-thiol derivative, was developed via computer-aided drug design and de novo synthesis. MTT assay showed it had potent anti-proliferative activity on various human cancer cells. Treatment of cancer cells with SKLB-163 induced obvious apoptosis and inhibited proliferation in vitro. SKLB-163 administered p.o. showed a marked antitumor activity in vivo. Proteomic techniques were employed to identify possible drug target proteins. The data showed molecular mechanism of action might be involved in downregulation of RhoGDI, which finally contributed to increased apoptosis and inhibited proliferation. These findings provided the potential value of SKLB-163 as a novel candidate antitumor drug.

  10. Removal of cations using ion-binding terpolymer involving 2-amino-6-nitro-benzothiazole and thiosemicarbazide with formaldehyde by batch equilibrium technique.

    Science.gov (United States)

    Ahamed, Mohamed A Riswan; Jeyakumar, Duraisamy; Burkanudeen, Abdul R

    2013-03-15

    2-Amino-6-nitro-benzothiazole and thiosemicarbazide with formaldehyde (BTF) terpolymer was synthesized by the condensation polymerization technique. The elemental analysis and physico-chemical parameters of the terpolymer were measured. This chelation terpolymer was characterized by infrared, electronic and nuclear magnetic resonance ((1)H &(13)C NMR) spectral studies. The molecular weight of the terpolymer was determined by gel permeation chromatography (GPC). Surface analysis of the terpolymer was analyzed by scanning electron microscopy (SEM) and X-ray diffraction (XRD) method. The thermal stability of the terpolymer was analyzed by thermogravimetric analysis (TGA). The cation-exchange property of the terpolymer was determined by batch equilibrium method with the effect of pH, contact time and electrolytes. The reusability of the resin was also studied to estimate the effectiveness of the terpolymer resin.

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

    Science.gov (United States)

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

    2014-04-01

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

  12. Synthesis and characterization of thermally stable second-order nonlinear optical side-chain polyimides containing thiazole and benzothiazole push-pull chromophores

    Science.gov (United States)

    Tambe, S. M.; Kittur, A. A.; Inamdar, S. R.; Mitchell, G. R.; Kariduraganavar, M. Y.

    2009-04-01

    Push-pull nonlinear optical (NLO) chromophores containing thiazole and benzothiazole acceptors were synthesized and characterized. Using these chromophores a series of second-order NLO polyimides were successfully prepared from 4,4'-(hexafluoroisopropylidene) diphthalic anhydride (6FDA), pyromellitic dianhydride (PMDA) and 3,3'4,4'-benzophenone tetracarboxylic dianhydride (BTDA) by a standard condensation polymerization technique. These polyimides exhibit high glass transition temperatures ranging from 160 to 188 °C. UV-vis spectrum of polyimide exhibited a slight blue shift and decreases in absorption due to birefringence. From the order parameters, it was found that chromophores were aligned effectively. Using in situ poling and temperature ramping technique, the optical temperatures for corona poling were obtained. It was found that the optimal temperatures of polyimides approach their glass transition temperatures. These polyimides demonstrate relatively large d33 values range between 35.15 and 45.20 pm/V at 532 nm.

  13. Benzothiazoles with tunable electron-withdrawing strength and reverse polarity: a route to triphenylamine-based chromophores with enhanced two-photon absorption.

    Science.gov (United States)

    Hrobárik, Peter; Hrobáriková, Veronika; Sigmundová, Ivica; Zahradník, Pavol; Fakis, Mihalis; Polyzos, Ioannis; Persephonis, Peter

    2011-11-01

    A series of dipolar and octupolar triphenylamine-derived dyes containing a benzothiazole positioned in the matched or mismatched fashion have been designed and synthesized via palladium-catalyzed Sonogashira cross-coupling reactions. Linear and nonlinear optical properties of the designed molecules were tuned by an additional electron-withdrawing group (EWG) and by changing the relative positions of the donor and acceptor substituents on the heterocyclic ring. This allowed us to examine the effect of positional isomerism and extend the structure-property relationships useful in the engineering of novel heteroaromatic-based systems with enhanced two-photon absorption (TPA). The TPA cross-sections (δ(TPA)) in the target compounds dramatically increased with the branching of the triphenylamine core and with the strength of the auxiliary acceptor. In addition, a change from the commonly used polarity in push-pull benzothiazoles to a reverse one has been revealed as a particularly useful strategy (regioisomeric control) for enhancing TPA cross-sections and shifting the absorption and emission maxima to longer wavelengths. The maximum TPA cross-sections of the star-shaped three-branched triphenylamines are ∼500-2300 GM in the near-infrared region (740-810 nm); thereby the molecular weight normalized δ(TPA)/MW values of the best performing dyes within the series (2.0-2.4 GM·g(-1)·mol) are comparable to those of the most efficient TPA chromophores reported to date. The large TPA cross-sections combined with high emission quantum yields and large Stokes shifts make these compounds excellent candidates for various TPA applications, including two-photon fluorescence microscopy.

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

    Science.gov (United States)

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

    2010-06-01

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

  15. A trinuclear palladium(II) complex containing N,S-coordinating 2-(benzylsulfanyl)anilinide and 1,3-benzothiazole-2-thiolate ligands with a central square-planar PdN4 motif.

    Science.gov (United States)

    Cross, Edward D; MacDonald, Kristen L; McDonald, Robert; Bierenstiel, Matthias

    2014-01-01

    The reaction of dichlorido(cod)palladium(II) (cod = 1,5-cyclooctadiene) with 2-(benzylsulfanyl)aniline followed by heating in N,N-dimethylformamide (DMF) produces the linear trinuclear Pd3 complex bis(μ2-1,3-benzothiazole-2-thiolato)bis[μ2-2-(benzylsulfanyl)anilinido]dichloridotripalladium(II) N,N-dimethylformamide disolvate, [Pd3(C7H4NS2)2(C13H12NS)2Cl2]·2C3H7NO. The molecule has -1 symmetry and a Pd...Pd separation of 3.2012 (4) Å. The outer Pd(II) atoms have a square-planar geometry formed by an N,S-chelating 2-(benzylsulfanyl)anilinide ligand, a chloride ligand and the thiolate S atom of a bridging 1,3-benzothiazole-2-thiolate ligand, while the central Pd(II) core shows an all N-coordinated square-planar geometry. The geometry is perfectly planar within the PdN4 core and the N-Pd-N bond angles differ significantly [84.72 (15)° for the N atoms of ligands coordinated to the same outer Pd atom and 95.28 (15)° for the N atoms of ligands coordinated to different outer Pd atoms]. This trinuclear Pd3 complex is the first example of one in which 1,3-benzothiazole-2-thiolate ligands are only N-coordinated to one Pd centre. The 1,3-benzothiazole-2-thiolate ligands were formed in situ from 2-(benzylsulfanyl)aniline.

  16. cis-Bis[2-(1,3-benzothia-zol-2-yl)-1-(4-fluoro-phen-yl)ethen-yl](pentane-2,4-dionato-κO,O')iridium(III).

    Science.gov (United States)

    Xiao, Guo-Yong; Lei, Peng; Chi, Hai-Jun; Hu, Zhi-Zhi; Li, Xiao

    2009-03-25

    In the title compound, [Ir(C(15)H(9)FNS)(2)(C(5)H(7)O(2))], the Ir atom is hexa-coordinated by three chelating ligands, with two cyclo-metalated 2-(1,3-benzothia-zol-2-yl)-1-(4-fluoro-phen-yl)ethenyl ligands showing N,C-bidentate coordination and an O,O'-bidenate pentane-2,4-dionate anion, thereby forming a distorted octa-hedral enviroment.

  17. INFLUENCIA DE LA COMPOSICIÓN QUÍMICA SUPERFICIAL DEL CARBÓN ACTIVADO EN LA ADSORCIÓN DE BENZOTIAZOLES INFLUENCE OF ACTIVATED CARBON CHEMICAL SURFACE COMPOSITION ON THE ADSORPTION OF BENZOTHIAZOLES

    Directory of Open Access Journals (Sweden)

    Héctor Valdés

    2010-04-01

    Full Text Available Los benzotiazoles están esparcidos en el ambiente debido a su gran variedad de aplicaciones. Dentro de ellos, el benzotiazol (BT, el 2-hidroxibenzotiazol (OHBT, y el 2-metilbenzotiazol (MeBT son conocidos como agentes tóxicos y poco biodegradables. La adsorción con carbón activado se plantea como una opción atractiva para la remoción de estos contaminantes. Sin embargo, existen dudas acerca del efecto de las propiedades químicas superficiales del carbón activado sobre la capacidad de adsorción de estos compuestos. Para el estudio se utilizó carbón activado granular Filtrasorb-400 modificado con el objetivo de obtener carbones con diferentes propiedades químicas superficiales. Las series de carbones activados fueron obtenidas por pretratamiento por desoxigenación y por oxidación con ozono a diferentes tiempos de contacto. El incremento en la concentración de los grupos oxigenados superficiales produce una disminución en la capacidad de adsorción de los tres contaminantes ensayados. Los resultados sugieren que el mecanismo de adsorción transcurre principalmente a través de las interacciones de dispersión π-π entre los electrones del plano basal del carbón y el anillo aromático de los benzotiazoles. A valores de pH mayores al valor del pH de carga cero de la superficie del carbón activado (pH PZC, la capacidad de adsorción del carbón activado disminuye debido a la aparición de interacciones electrostáticas repulsivas entre los grupos superficiales oxigenados ionizados y las moléculas ionizadas de los benzotiazoles.Benzothiazoles, such as benzothiazole (BT, 2-hydroxybenzothiazole (OHBT, and 2-methylbenzothiazole (MeBT are toxic and poorly biodegradable organic compounds, frequently present in wastewater from rubber related applications. Activated carbon adsorption has been identified as an attractive treatment to removing those contaminants. This paper presents experimental results on the effect of chemical surface

  18. Electronic Structures and Spectroscopic Properties of a Novel Iridium (Ⅲ) Complex with an Ancillary Ligand 2- (4-Trifluoromethyl -2-Hydroxylphenyl)Benzothiazole

    Institute of Scientific and Technical Information of China (English)

    LEI Li-Ping; HAO Yu-Ying; FAN Wen-Hao; XU Sing-She

    2011-01-01

    Iridium (W) complexes with 2-phenylpyridine (ppy) have been demonstrated as a type of promising phosphorescence dopant in emitting layers of organic light emitting diodes (OLKDs). In most iridium (M) complexes, there exist the strong spin-orbit coupling between it-orbiteds of cyclometalated ligands and 5d orbitals of the centric iridium. We study a novel iridium (M) complex (ppy)2lr(4-TfmBTZ) with ppy as cyclometalated ligands and 2-(4-trifluoromcthyl-2-hydroxyIphenyl)benzothiazole (4-TfmBTZ) as an ancillary ligand using the Gaussian 03 program. The geometries, electronic structures and spectroscopic properties of this iridium (M) complex are investigated by density functional theory (DFT) and time-dependent density functional theory (TD-DFT). The results show that the spin-orbit coupling occurs not only between ppy and iridium atom but also between 4-TfmBTZ and iridium atom in this complex. The highest occupied molecular orbital is dominantly localized on the Ir atom and 4-TfmBTZ ligand, while the lowest unoccupied molecular orbital on 4-TfmBTZ ligand. The triplet lowest-lying transition is attributed to the Ir-to-4-TfmBTZ charge-transfer ^MLCT) transition while the sub-low-lying transitions are assigned to the AMLCT transitions oflr(ppy)I. The nature of the lowest unoccupied orbital changes from ppy-localizcd to 4-TfmBTZ-locaIized and reveals that phosphorescent color oflr(M) complex can be controlled by the ancillary ligand and substitucnt.%@@ Iridium (Ⅲ) complexes with 2-phenylpyridine (ppy) have been demonstrated as a type of promising phospho- rescence dopant in emitting layers of organic light emitting diodes (OLEI)s).In most iridium (Ⅲ) complexes, there exist the strong spin-orbit coupling between π-orbitals of cyclometalated ligands anti 5d orbitals of the ccntric iridium.We study a novel iridium (Ⅲ) complex (ppy)2Ir(4-TfmBTZ) with ppy as cyclometalated ligands and 2-(4-trifluoromethyl-2-hydroxylphenyl)benzothiazole (4-TfmBTZ) as an ancillary ligand

  19. Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers.

    Science.gov (United States)

    Subba Rao, A V; Swapna, Konderu; Shaik, Siddiq Pasha; Lakshma Nayak, V; Srinivasa Reddy, T; Sunkari, Satish; Shaik, Thokhir Basha; Bagul, Chandrakant; Kamal, Ahmed

    2017-02-01

    A series of colchicine site binding tubulin inhibitors were synthesized by the modification of the combretastatin pharmacophore. The ring B was replaced by the pharmacologically relevant benzothiazole scaffolds, and the cis configuration of the olefinic bond was restricted by the incorporation of a triazole and tetrazole rings which is envisaged by the structural resemblance to a tubulin inhibitor like combretastatin (CA-4). These compounds were evaluated for their antiproliferative activity on selected cancer cell lines and an insight in the structure activity relationship was developed. The most potent compounds (9a and 9b) demonstrated an antiproliferative effect comparable to that of CA-4. Mitotic cell cycle arrest in G2/M phase revealed the disruption of microtubule dynamics that was confirmed by tubulin polymerization assays and immunocytochemistry studies at the cellular level. Western blot analysis revealed that these compounds accumulate more tubulin in the soluble fraction. The colchicine competitive binding assay and the molecular docking studies suggested that the binding of these mimics at the colchicine site of the tubulin is similar to that of CA-4. Moreover, the triggering of apoptotic cell death after mitotic arrest was investigated by studying their effect by Hoechst staining, Annexin-V-FITC assay, mitochondrial membrane potential, ROS generation and caspase-3 activation.

  20. An electro-optical and electron injection study of benzothiazole-based squaraine dyes as efficient dye-sensitized solar cell materials: a first principles study.

    Science.gov (United States)

    Al-Fahdan, Najat Saeed; Asiri, Abdullah M; Irfan, Ahmad; Basaif, Salem A; El-Shishtawy, Reda M

    2014-12-01

    Squaraine dyes have attracted significant attention in many areas of daily life from biomedical imaging to semiconducting materials. Moreover, these dyes are used as photoactive materials in the field of solar cells. In the present study, we investigated the structural, electronic, photophysical, and charge transport properties of six benzothiazole-based squaraine dyes (Cis-SQ1-Cis-SQ3 and Trans-SQ1-Trans-SQ3). The effect of electron donating (-OCH3) and electron withdrawing (-COOH) groups was investigated intensively. Ground state geometry and frequency calculations were performed by applying density functional theory (DFT) at B3LYP/6-31G** level of theory. Absorption spectra were computed in chloroform at the time-dependent DFT/B3LYP/6-31G** level of theory. The driving force of electron injection (ΔG (inject)), relative driving force of electron injection (ΔG r (inject)), electronic coupling constants (|VRP|) and light harvesting efficiency (LHE) of all six compounds were calculated and compared with previously studied sensitizers. The ΔG (inject), ΔG r (inject) and |VRP| of all six compounds revealed that these sensitizers would be efficient dye-sensitized solar cell materials. Cis/Trans-SQ3 exhibited superior LHE as compared to other derivatives. The Cis/Trans geometric effect was studied and discussed with regard to electro-optical and charge transport properties.

  1. Design and synthesis of cis-restricted benzimidazole and benzothiazole mimics of combretastatin A-4 as antimitotic agents with apoptosis inducing ability.

    Science.gov (United States)

    Ashraf, Md; Shaik, Thokhir B; Malik, M Shaheer; Syed, Riyaz; Mallipeddi, Prema L; Vardhan, M V P S Vishnu; Kamal, Ahmed

    2016-09-15

    A series of colchicine site binding tubulin inhibitors were designed and synthesized by the modification of the combretastatin A-4 (CA4) pharmacophore. The ring B was replaced by the pharmacologically relevant benzimidazole or benzothiazole scaffolds, and the cis-configuration of the olefinic bond was restricted by the incorporation of a pyridine ring which is envisaged by the structural resemblance to a tubulin inhibitor like E7010. These compounds were evaluated for their antiproliferative activity on selected cancer cell lines and an insight in the structure activity relationship was developed. The most potent compounds (6c and 6l) demonstrated an antiproliferative effect comparable and superior to that of CA4 (GI50 up to 40nM). Mitotic cell cycle arrest in G2/M phase revealed the disruption of microtubule dynamics that was confirmed by tubulin polymerization assays and immunocytochemistry studies at the cellular level. The molecular docking studies suggested that the binding of these mimics at the colchicine site of the tubulin is similar to that of combretastatin A-4.

  2. Conformational structure of the unsymmetrical monomethine cyanine bearing 2-azaazulene and 2-benzothiazole residues as terminal groups: Experimental and quantum-chemical investigation

    Science.gov (United States)

    Ryabitskii, Aleksey B.; Bricks, Julia L.; Kachkovskii, Aleksey D.; Chernega, Alexander N.; Vlasenko, Yurii G.

    2010-10-01

    Conformational features of unsymmetrical monomethine cyanine dye 2-[(2-butyl-1,3-dimethylcyclohepta[ c]pyrrol-6(2 H)-ylidene)methyl]-3-ethyl-1,3-benzothiazol-3-ium iodide-perchlorate have been investigated in solution by means of NMR spectroscopy and in the solid state by X-ray diffraction. The possibility of molecule conformational transformations was proved by scanning of potential energy surface along torsion angels. The corresponding energy barriers values have been calculated by means of DFT (B3LYP and M05-2X) methods. A comparison of structural parameters obtained by means of both methods was reported. The isomerization process was investigated by dynamic NMR spectroscopy. A comparison of 1H NMR spectra recorded in different solvents was performed. It was shown that in solution, intramolecular rotation around the bond С(6) аzaazulene-С methyne decelerated in NMR time scale took place. The data on dynamic behavior of dye molecules have been compared with the experimental X-ray data. Quantum-chemical calculation results are in agreement with the experimental data.

  3. Molecular, spectroscopic and thermal studies on catechol, 4,5-dibromocatechol, resorcinol, hydroquinone and 4-4‧-dihydroxybiphenyl derivatives armed with benzothiazole moieties

    Science.gov (United States)

    Alshargabi, Arwa; Yeap, Guan-Yeow; Mahmood, Wan Ahmad Kamil; Samikannu, Rakesh

    2013-05-01

    A new series of catechol, 4,5-dibromocatechol, resorcinol, hydroquinone and 4-4'-dihydroxybiphenyl derivatives possessing two benzothiazole moieties at respective positions of 1,2, 1,3, 1,4 and/or 4,4' has successfully been synthesized. The molecular structures were fully elucidated by spectroscopic techniques (1H NMR, 13C NMR and two dimensional COSY, HMBC, HMQC, DEPT-135 and DEPT-90). The connectivity study between the cause of using different core systems in the target compounds and the anisotropic behavior as inferred from phase transition temperature and relevant morphology studies has led to some unique features arising from this series. Compounds with ortho substituent exhibit enantiotropic N and SmA phases. The analogues containing resorcinol and 4,4'-disubstituentbiphenyl show enanotiotropic nematic behavior while the hydroquinone derivative induces the formation of monotropic nematogen. An extensive study to further substantiate the relationship between the stability of the nematic phase and associated transition temperatures due to different core systems is also reported.

  4. Assessment of 2-(4-morpholinyl) benzothiazole (24MoBT) and N-cyclohexyl-2-benzothiazolamine (NCBA) as traffic tracers in metropolitan cities of China and India

    Science.gov (United States)

    Pan, Suhong; Sun, Yali; Zhang, Gan; Li, Jun; Xie, Qilai; Chakraborty, Paromita

    2012-09-01

    2-(4-Morpholinyl) benzothiazole (24MoBT) and N-cyclohexyl-2-benzothiazolamine (NCBA), which are present in automobile tires, are impurities of the vulcanisation accelerators OBS and CBS, respectively, as defined by the Japan Industrial Standard. To assess 24MoBT and NCBA as markers to trace the usage patterns of OBS and CBS in developing countries, urban dusts were collected from five representative cities of China and India for the analysis of 24MoBT and NCBA. The concentrations in these dust samples were found to be within the range of 3.40-151 ng g-1 for 24MoBT and nd-56.9 ng g-1 for NCBA. The higher levels of 24MoBT may indicate that the traditional accelerator OBS is still used in vehicle tires, whereas the relatively lower contents of NCBA are mainly related to the lesser use of CBS tires. The individual fractions of 24MoBT and NCBA in BTs (24MoBT + NCBA) are compared among cities, and the results show that the fraction sequence is consistent with the number of vehicles and the cities' economic development. This study indicates not only that 24MoBT is presently more suitable for tracing tire wear emissions than NCBA in China but also that there is a potential to assess the impact of traffic sources on urban environments using BTs.

  5. Synthesis, photophysical and charge-transporting properties of a novel asymmetric indolo [3,2-b]carbazole derivative containing benzothiazole and diphenylamino moieties

    Science.gov (United States)

    Shi, Heping; Yuan, Jiandong; Dong, Xiuqing; Cheng, Fangqin

    2014-12-01

    A novel asymmetric donor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-diphenylamino-5,11-dihexylindolo[3,2-b]carbazole (BDDAICZ), has been successfully synthesized by introducing a benzothiazole moiety (as an electron-acceptor) and a diphenylamino moiety (as an electron-donor) to 2-position and 8-position of indolo[3,2-b]carbazole moiety (as a skeleton and an electron-donor), and characterized by elemental analysis, 1H NMR, 13C NMR and MS. The thermal, electrochemical properties of BDDAICZ were characterized by thermogravimetric analysis combined with electrochemistry. The absorption and emission spectra of BDDAICZ was experimentally determined in several solvents and computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated absorption and emission wavelengths are coincident with the measured data. The ionization potential (IP), the electron affinity (EA) and reorganization energy of BDDAICZ were also investigated using density functional theory (DFT). Charge-transporting properties of BDDAICZ were characterized by OLEDs devices fabricated by using it as charge-transport layers. The results show that BDDAICZ has excellent thermal stability, electrochemical stability and hole-transporting properties, indicating its potential application as a hole-transporting material in OLEDs devices.

  6. Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells.

    Science.gov (United States)

    Kamal, Ahmed; Faazil, Shaikh; Ramaiah, M Janaki; Ashraf, Md; Balakrishna, M; Pushpavalli, S N C V L; Patel, Nibedita; Pal-Bhadra, Manika

    2013-10-15

    By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 μM as well as 4 μM concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers.

  7. 99mTc(CO)3-Labeled Benzothiazole Derivatives Preferentially Bind Cerebrovascular Amyloid: Potential Use as Imaging Agents for Cerebral Amyloid Angiopathy.

    Science.gov (United States)

    Jia, Jianhua; Cui, Mengchao; Dai, Jiapei; Liu, Boli

    2015-08-03

    Cerebral amyloid angiopathy (CAA) is a disorder affecting the elderly that is characterized by amyloid-β (Aβ) deposition in blood vessel walls of the brain. A series of 99mTc(CO)3-labeled benzothiazole derivatives as potential SPECT imaging probes for cerebrovascular Aβ deposition is reported. Rhenium surrogate displayed high affinities to Aβ aggregates with Ki values ranging from 106 to 42 nM, and they strongly stained Aβ deposits in transgenic mice (Tg) and Alzheimer's disease (AD) patients. In vitro autoradiography on brain sections of Tg and AD patients confirmed that [99mTc]24 possessed sufficient affinity for Aβ plaques, and [99mTc]24 could only label Aβ deposition in blood vessels but not Aβ plaques in the parenchyma of the brain of AD patients. Moreover, [99mTc]24 possessed favorable initial uptake (1.21% ID/g) and fast blood washout (blood2 min/blood60 min=23) in normal mice. These preliminary results suggest that [99mTc]24 may be used as an Aβ imaging probe for the detection of CAA.

  8. Design, synthesis, and structure-activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents.

    Science.gov (United States)

    Ma, Junjie; Chen, Dong; Lu, Kuan; Wang, Lihui; Han, Xiaoqi; Zhao, Yanfang; Gong, Ping

    2014-10-30

    A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity against all the tested cell lines. Among them, compounds 15g (procaspase-3 EC50 = 1.42 μM) and 16b (procaspase-3 EC50 = 0.25 μM) exhibited excellent antitumor activity with IC50 values ranging from 0.14 μM to 0.98 μM against all cancer cell lines, which were 1.8-8.7 times more active than the first procaspase activating compound (PAC-1) (procaspase-3 EC50 = 4.08 μM). The structure-activity relationship (SAR) analyses indicated that the introduction of a lipophilic group (a benzyloxy or heteroaryloxy group) at the 4-position of the 2-hydroxy phenyl ring was beneficial to antitumor activity, and the presence of substituents containing nitrogen that are positively charged at physiological pH could also improve antitumor activity. It was also confirmed that the steric effect of the 4-position substituent of the benzyloxy group had a significant influence on cytotoxic activity.

  9. Design, synthesis, biological evaluation and preliminary mechanism study of novel benzothiazole derivatives bearing indole-based moiety as potent antitumor agents.

    Science.gov (United States)

    Ma, Junjie; Bao, Guanglong; Wang, Limei; Li, Wanting; Xu, Boxuan; Du, Baoquan; Lv, Jie; Zhai, Xin; Gong, Ping

    2015-01-01

    Through a structure-based molecular hybridization approach, a series of novel benzothiazole derivatives bearing indole-based moiety were designed, synthesized and screened for in vitro antitumor activity against four cancer cell lines (HT29, H460, A549 and MDA-MB-231). Most of them showed moderate to excellent activity against all the tested cell lines. Among them, compounds 20a-w with substituted benzyl-1H-indole moiety showed better selectivity against HT29 cancer cell line than other compounds. Compound 20d exhibited excellent antitumor activity with IC50 values of 0.024, 0.29, 0.84 and 0.88 μM against HT29, H460, A549 and MDA-MB-231, respectively. Further mechanism studies indicated that the marked pharmacological activity of compound 20d might be ascribed to activation of procaspase-3 (apoptosis-inducing) and cell cycle arrest, which had emerged as a lead for further structural modifications. Furthermore, 3D-QSAR model (training set: q(2) = 0.850, r(2) = 0.987, test set: r(2) = 0.811) was built to provide a comprehensive guide for further structural modification and optimization.

  10. A pressurised hot water extraction and liquid chromatography-high resolution mass spectrometry method to determine polar benzotriazole, benzothiazole and benzenesulfonamide derivates in sewage sludge.

    Science.gov (United States)

    Herrero, P; Borrull, F; Marcé, R M; Pocurull, E

    2014-08-15

    Benzothiazole, benzotriazole and benzenesulfonamide derivates are well-known aquatic contaminants, although very few studies have been published about their occurrence in sewage sludge samples. In this paper, a pressurised hot water extraction (PHWE) method has been developed for the simultaneous determination of these families of compounds. The compounds were determined by LC-Orbitrap-HRMS and several clean-up strategies such as in-cell PHWE and solid-phase extraction (SPE) were tested to reduce the high matrix effect that occurs when sludge samples are analysed. Absolute recoveries using the whole method were above 80% and the matrix effect was under -20% for most of the compounds studied. Repeatability and reproducibility were usually under 10% (%RSD, 50 and 250ngg(-1) (d.w.), n=5), while LODs and LOQs were between 0.25 and 25ngg(-1) (d.w.) and 0.5 and 50ngg(-1) (d.w.), respectively. The PHWE/SPE/LC-HRMS method developed was used to analyse several sludge samples collected from five sewage treatment plants (STPs) in Catalonia that use different sewage treatments. The most frequently determined compounds were benzotriazole derivates and the most abundant compound found was 2-hydroxybenzothiazole.

  11. Synthesis of novel inhibitors of α-glucosidase based on the benzothiazole skeleton containing benzohydrazide moiety and their molecular docking studies.

    Science.gov (United States)

    Taha, Muhammad; Ismail, Nor Hadiani; Lalani, Salima; Fatmi, Muhammad Qaiser; Atia-Tul-Wahab; Siddiqui, Salman; Khan, Khalid Mohammed; Imran, Syahrul; Choudhary, Muhammad Iqbal

    2015-03-06

    In an effort to design and synthesize a new class of α-glucosidase inhibitor, we synthesized benzothiazole hybrid having benzohydrazide moiety (5). Compound 5 was reacted with various substituted aryl aldehyde to generate a small library of compounds 6-35. Synthesis of compounds was confirmed by the spectral information. These compounds were screened for their α-glucosidase activity. They showed a varying degree of α-glucosidase inhibition with IC50 values ranging between 5.31 and 53.34 μM. Compounds 6, 7, 9-16, 19, 21-30, 32-35 showed superior activity as compared to standard acarbose (IC50 = 906 ± 6.3 μM). This has identified a new class of α-glucosidase inhibitors. The predicted physico-chemical properties indicated the drug appropriateness for most of these compounds, as they obey Lipinski's rule of five (RO5). A hybrid B3LYP density functional theory (DFT) was employed for energy, minimization of 3D structures for all synthetic compounds using 6-311 + G(d,p) basis sets followed by molecular docking to explore their interactions with human intestinal C- and N-terminal domains of α-glucosidase. All compounds bind to the prospective allosteric site of the C- terminal domain, and consequently, may be considered as mixed inhibitors. It was hypothesized that both the dipole moment and H-bond interactions govern the biological activation of these compounds.

  12. 水相中微波辐射下铜催化合成苯并噻唑衍生物%Copper-catalyzed Microwave-assisted Synthesis of Benzothiazoles Derivatives in Water

    Institute of Scientific and Technical Information of China (English)

    柯方; 林晨; 李鹏

    2013-01-01

    Objective Benzothiazoles were synthesized under microwave irradiation in water . Methods A variety of 2-iodoanilines and aldehydes could be reacted with sodium sulfide to give the desired corresponding products in high yields in 100 ℃ water for 30 min using copper catalysts under microwave ir-radiation . Results We have developed an efficient protocol for benzothiazoles ,9 target compounds can be synthesized in good to excellent yields up to 94% , and all of them were further characterized by 1 H NMR ,13C NMR and MS analysis . Conclusion Synthesis of target benzothiazoles compounds under microwave irradiation in water has an advantage of short reaction time and higher the yields compared to the conventional method .%目的:用微波辐射催化法在水相中合成苯并噻唑化合物。方法在150 W微波辐射条件下,以CuCl2和菲啰啉为催化剂,2-碘芳烃、芳醛和硫化钠在100℃水相中反应30 min得到目标苯并噻唑化合物。结果合成得到9个相应的苯并噻唑化合物,均通过1 H NMR、13C NMR和质谱确认结构,最高收率为94%。结论使用微波辐射法水相中合成目标产物,与传统方法相比,避免使用大量有机溶剂对环境造成污染,且具有时间短、收率高的优点。

  13. Degradation of Benzothiazole in Electro-Assisted Microbial Reactor%电辅助微生物反应器降解苯并噻唑效能的研究

    Institute of Scientific and Technical Information of China (English)

    刘春苗; 丁杰; 刘先树; 程旺斌

    2014-01-01

    本研究采用单室电辅助微生物反应器(EAMR)氧化苯并噻唑(BTH),考察了外加电压和 COD/ BTH 对 BTH 降解效能的影响.结果发现,BTH 在阳极氧化降解为2-羟基苯并噻唑(OHBT)后,噻唑环断裂,最终转化为2-甲磺酰基苯胺; BTH 的降解过程符合表观一级动力学规律,并且提高外加电压和引入共基质代谢作用均能提高 BTH 的降解反应速率常数;在外加电压0.7 V 和 COD/ BTH 值为30:1时,48 h 后 BTH 的降解率可以达到96%,实现了 BTH 类废水的高效脱毒,为后续生物处理创造了有利的条件.%The oxidative degradation of benzothiazole (BTH) in a single-chamber electro-assisted microbial reactor was investigated. The effects of applied voltage and COD/ BTH ratio on the performance of degrading benzothiazole were studied. The research showed that BTH was oxidized to 2-hydroxy-benzothiazole ( OHBT ), then thiazole ring scission, and BTH translated into 2-methylsulfonylaniline eventually. The degrading of benzothiazole was in conformity with the pseudo first-order kinetic model, and the pseudo first-order kinetic constant can be increased by raising the applied voltage and co-metabolism. When the applied voltage was 0. 7 V and COD/ BTH ratio was 30, the degradation rate was 96% in 48 h, achieving the detoxification of BTH, and that is advantageous to the biochemical treatment.

  14. A highly selective fluorescent 'turn-on' chemosensor for Zn(2+) based on a benzothiazole conjugate: their applicability in live cell imaging and use of the resultant complex as a secondary sensor of CN(-).

    Science.gov (United States)

    Khairnar, Nilesh; Tayade, Kundan; Sahoo, Suban K; Bondhopadhyay, Banashree; Basu, Anupam; Singh, Jasminder; Singh, Narinder; Gite, Vikas; Kuwar, Anil

    2015-02-07

    A benzothiazole derivative linked "off-on" multi-responsive and selective chemosensor has been synthesized and evaluated for cation recognition properties. The receptor shows a high sensitivity and selectivity for Zn(2+) through a 'turn-on' fluorescence response over the other tested cations with a detection limit as low as 0.67 μM. The receptor was successfully applied for the detection of Zn(2+) in live HeLa cells. Then, the Zn(2+) complex of receptor was also used for cyanide detection and recognition.

  15. 一种苯并噻唑类稳定烯醇的合成及晶体结构%Synthesis and Crystal Structure of Stable Benzothiazole Enol

    Institute of Scientific and Technical Information of China (English)

    霍宝龙; 薛灵伟; 杨运旭; 杨超; 李大芝; 王爱志; 禹菲菲; 胡碧玮

    2014-01-01

    以2-甲基苯并噻唑和1,3-丙磺酸内酯为起始原料,合成了一种菁染料中间体2-(2-乙氧基-1-丁烯基)-1-(3-磺酸丙基)苯并噻唑(3).该染料中间体极易水解,对其水解产物(4e)采用红外光谱、核磁共振、质谱、元素分析和X射线单晶衍射分析等方法进行了表征. MS结果显示水解产物4e的分子量为327;在13 C NMR谱图中,烯醇结构中与羟基相连的碳的化学位移为194.05,与之相连的另一个双键碳的化学位移为δ92.52;在IR谱图中,1618 cm-1处存在烯醇的特征吸收峰;通过X射线单晶衍射分析测定了水解产物的结构,进一步证实该水解产物是一种存在共轭芳基结构的稳定烯醇.%As an important organic functional compound, 2-methylbenzothiazole derivatives has been widely used in sensitizing dyes. In the process of sythesis of dyes, the dye intermediates could be hydrolyzed to form another substance easily. In order to determine the structure of the new substance, a dye intermediate, named 2-(2-ethoxy-1-butenyl)-1-( 3-sulfopropyl ) benzothiazole ( 3 ) , was synthesized using 2-methyl benzothiazole and 1,3-propane sultone as the starting material, then hydrolyzed in water to form the new substance(4e), which was characterized by IR, 1 H NMR, 13 C NMR, MS, elemental analysis and X-ray diffraction methods. The MS spectrum showed the molecular weight of the product was 327 , which was corresponding to the target compound 4e. The 13 C NMR spectrum showed the chemical shift of the carbon that connected to the enol hy-droxyl group was δ194.05 , and the chemical shift of the carbon that connected to the double bond was 92.52, which implied the existence of enol structure. The IR spectrum also showed the enol hydroxyl charac-teristic absorption peak at 1618 cm-1 . X-Ray diffraction displayed the structure of the target compound intui-tively. Through the characterizations of the compound, the new substance was comfirmed to be a stable enol that

  16. Preconcentration and determination of trace silver ion using benzothiazole calix[4]arene modified silica by flow injection flame atomic absorption spectrometry.

    Science.gov (United States)

    Waluvanaruk, Jitwilai; Aeungmaitrepirom, Wanlapa; Tuntulani, Thawatchai; Ngamukot, Passapol

    2014-01-01

    The silica gel modified with benzothiazole calix[4]arene (APS-L1) via Schiff's base reaction was applied as a sorbent in an online system for preconcentration and determination of silver ion by flame atomic absorption spectrometry (FAAS). APS-L1 was used as an effective sorbent for solid phase extraction (SPE) of silver(I) ion in both batch and column methods. The optimum experimental parameters such as pH, eluent type, sample flow rate, eluent volume and eluent flow rate including the effect of interfering ions were investigated. Silver(I) ion was determined at pH 6-7. The capacity of APS-L1 sorbent was found to be 12.2 mg/g of sorbent. The high affinity was obtained without interference from the interfering ions. The optimum conditions of the online flow injection preconcentration coupled with the FAAS (FI-FAAS system) were evaluated. The sample flow rate was 3.0 mL min(-1) using sample volume of 5-10 mL. Elution was performed with 250 μL of 0.1 mol L(-1) thiosulfate at the flow rate of 1.5 mL min(-1). The analytical characteristics and performance of the FI-FAAS system were studied under optimum conditions using a solution spiked with standard silver(I) ion at 20 and 50 μg L(-1). The detection limit of 0.44 μg L(-1) was obtained. The accuracy of the proposed method was evaluated and percentages of recovery at 20 and 50 μg L(-1) were 100.2 and 99.5%, respectively. The percent relative standard deviations (%RSD) at 20 and 50 μg L(-1) were 6.1 and 3.3%, respectively. The developed method was successfully applied to determine trace silver(I) ion in drinking and tap water samples.

  17. Efficient tandem solid-phase extraction and liquid chromatography-triple quadrupole mass spectrometry method to determine polar benzotriazole, benzothiazole and benzenesulfonamide contaminants in environmental water samples.

    Science.gov (United States)

    Herrero, P; Borrull, F; Pocurull, E; Marcé, R M

    2013-09-27

    An analytical method has been developed that allows the simultaneous determination of five benzotriazole (BTRs), four benzothiazole (BTs) and five benzenesulfonamide (BSAs) derivates. The method is based on tandem solid-phase extraction (SPE) with Oasis HLB followed by a clean-up step with Florisil. The chromatographic analysis was performed in less than 15min and detection was carried out with a triple quadrupole mass analyser operating in multiple reaction monitoring (MRM) mode. A comparison was performed between Oasis HLB and Oasis MAX sorbents for the solid-phase extraction, with Oasis HLB being the sorbent that gave the highest recoveries, ranging between 75% and 106%, depending on the compound and the matrix analysed. The proposed clean-up with Florisil sorbent reduced the matrix effect to below 20%. The repeatability (%RSD, 50-3000ng/L, n=3) of the method was less than 15% for all of the compounds in all of the matrices. The limits of detection (LODs) achieved ranged from 1ng/L for BTR in river water up to 100ng/L for BT in influent sewage. All of the compounds were determined in environmental waters such as river water and sewage. The highest concentrations determined corresponded to influent sewage samples in which the sum of concentrations for all compounds were between 4.6μg/L and 8.0μg/L. These concentrations were slightly reduced in secondary effluent and tertiary effluent sewage. Moreover, samples from tertiary effluent sewage based on ultra-filtration membrane treatments were also analysed and preliminary results seem to indicate that these treatments may be most effective for removing BTR, BT and BSA derivates.

  18. Electronic Structures and Spectroscopic Properties of a Novel Iridium (III) Complex with an Ancillary Ligand 2-(4-Trifluoromethyl -2-Hydroxylphenyl) Benzothiazole

    Science.gov (United States)

    Lei, Li-Ping; Hao, Yu-Ying; Fan, Wen-Hao; Xu, Bing-She

    2011-06-01

    Iridium (III) complexes with 2-phenylpyridine (ppy) have been demonstrated as a type of promising phosphorescence dopant in emitting layers of organic light emitting diodes (OLEDs). In most iridium (III) complexes, there exist the strong spin-orbit coupling between π-orbitals of cyclometalated ligands and 5d orbitals of the centric iridium. We study a novel iridium (III) complex (ppy)2Ir(4-TfmBTZ) with ppy as cyclometalated ligands and 2-(4-trifluoromethyl-2-hydroxylphenyl)benzothiazole (4-TfmBTZ) as an ancillary ligand using the Gaussian 03 program. The geometries, electronic structures and spectroscopic properties of this iridium (III) complex are investigated by density functional theory (DFT) and time-dependent density functional theory (TD-DFT). The results show that the spin-orbit coupling occurs not only between ppy and iridium atom but also between 4-TfmBTZ and iridium atom in this complex. The highest occupied molecular orbital is dominantly localized on the Ir atom and 4-TfmBTZ ligand, while the lowest unoccupied molecular orbital on 4-TfmBTZ ligand. The triplet lowest-lying transition is attributed to the Ir-to-4-TfmBTZ charge-transfer (3MLCT) transition while the sub-low-lying transitions are assigned to the 3MLCT transitions of Ir(ppy)2. The nature of the lowest unoccupied orbital changes from ppy-localized to 4-TfmBTZ-localized and reveals that phosphorescent color of Ir(III) complex can be controlled by the ancillary ligand and substituent.

  19. Highly efficient orange and red organic light-emitting diodes with iridium(III) complexes bearing benzothiazole cyclometallate ligands as emitters

    Energy Technology Data Exchange (ETDEWEB)

    Li, Ming [College of Chemistry, Sichuan University, Chengdu, 610064 (China); Wang, Qi [State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu, 610054 (China); Dai, Jun [College of Chemistry, Sichuan University, Chengdu, 610064 (China); Lu, Zhi-yun, E-mail: luzhiyun@scu.edu.cn [College of Chemistry, Sichuan University, Chengdu, 610064 (China); Huang, Yan [College of Chemistry, Sichuan University, Chengdu, 610064 (China); Yu, Jun-sheng, E-mail: jsyu@uestc.edu.cn [State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu, 610054 (China); Luo, Shuai [College of Chemistry, Sichuan University, Chengdu, 610064 (China); Su, Shi-jian, E-mail: mssjsu@scut.edu.cn [State Key Laboratory of Luminescent Materials and Devices and Institute of Polymer Optoelectronic Materials and Devices, South China University of Technology, Guangzhou, 510640 (China)

    2012-12-30

    Two iridium complexes bearing benzothiazole cyclometallate ligands, bis[2-(3 Prime ,5 Prime -di-tert-butylbiphenyl-4-yl)benzothiazolato-N,C{sup 2 Prime }]iridium(III) (acetylacetonate) [(tbpbt){sub 2}Ir(acac)] and bis[2-(9,9-dimethyl-9H-fluoren-2-yl)benzothiazolato-N,C{sup 2 Prime }]iridium(III) (acetylacetonate) [(fbt){sub 2}Ir(acac)], have been evaluated as orange and red electrophosphorescent materials. Both X-ray crystallographic analysis and photophysical results indicate that they possess alleviated self-quenching characteristics due to the existence of steric bulky ligands. As a result, phosphorescent organic light-emitting diodes (PhOLEDs) based on them show high performance even in heavily-doped level ({>=} 15 wt.%). The (tbpbt){sub 2}Ir(acac)-based PhOLED gives efficient orange emission with peak current efficiency of 26.9 cd/A (1280 cd/m{sup 2}) at doping ratio of 15 wt.%, while the 15 wt.% (fbt){sub 2}Ir(acac)-doped device emits efficient red light with Commission Internationale de l'Eclairage coordinates of (0.63, 0.36), and peak current and external quantum efficiency of 28.5 cd/A (1210 cd/m{sup 2}) and 15.6%, respectively. Moreover, all these heavily-doped PhOLEDs exhibit low efficiency roll-off at relatively high current density. - Highlights: Black-Right-Pointing-Pointer Two iridium complexes with bulky ligands are developed as orange/red emitter. Black-Right-Pointing-Pointer Organic light-emitting diodes using these phosphors show low efficiency roll-off. Black-Right-Pointing-Pointer High performance devices could be achieved under high doping ratio of {>=} 15 wt.%. Black-Right-Pointing-Pointer The high device efficiencies arise from the reduced self-quenching of the phosphors.

  20. Design and synthesis of new potent anticancer benzothiazole amides and ureas featuring pyridylamide moiety and possessing dual B-Raf(V600E) and C-Raf kinase inhibitory activities.

    Science.gov (United States)

    El-Damasy, Ashraf Kareem; Lee, Ju-Hyeon; Seo, Seon Hee; Cho, Nam-Chul; Pae, Ae Nim; Keum, Gyochang

    2016-06-10

    A new series of benzothiazole amide and urea derivatives tethered with the privileged pyridylamide moiety by ether linkage at the 6-position of benzothiazole (22 final compounds) has been designed and synthesized as potent anticancer sorafenib analogs. A selected group of twelve derivatives was appraised for its antiproliferative activity over a panel of 60 human cancer cell lines at a single dose concentration of 10 μM at National Cancer Institute (NCI, USA). Compounds 4b, 5a, 5b and 5d exhibited promising growth inhibitions and thus were further tested in advanced 5-dose testing assay to determine their GI50 values. The cellular based assay results revealed that 3,5-bis-trifluoromethylphenyl (5b) urea member is the best derivative with superior potency and efficacy compared to sorafenib as well as notable extended spectrum activity covering 57 human cancer cell lines. Kinase screening of compound 5b showed its kinase inhibitory effect against both B-Raf(V600E) and C-Raf. Moreover, the most potent derivatives in cells were investigated for their RAF inhibitory activities, and the results were rationalized with the molecular docking study. Profiling of CYP450 and hERG channel inhibitory effects for the active compounds revealed their low possibilities to exhibit undesirable drug-drug interactions and cardiac side effects.

  1. 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.

  2. Synthesis, Antibacterial Activities and Nuclease Properties of Ternary Copper(II) Complex Containing 2-(2'-Pyridyl)benzothiazole and Glycinate%Synthesis, Antibacterial Activities and Nuclease Properties of Ternary Copper(II) Complex Containing 2-(2'-Pyridyl)benzothiazole and Glycinate

    Institute of Scientific and Technical Information of China (English)

    Lu, Yanmei; Chen, Yongheng; ou, Zhibin; Chen, Shi; Zhuang, Chuxiong; Le, Xueyi

    2012-01-01

    A new ternary complex [Cu(PBT)(Gly)(H2O)]ClO4 (PBT=2-(2'-pyridyl)benzothiazole, and Gly=glycinate) has been synthesized and characterized by elemental analysis, molar conductivity, and IR methods. The complex, structurally characterized by single-crystal X-ray crystallography, shows a slightly distorted square-pyramidal coordination geometry in which two nitrogen atoms of PBT and the carboxylate oxygen atom O and the amino nitrogen atom N of Gly bind at the basal plane, a water molecule is coordinated at the apical position. The complex, Cu(ClO4)2 and flee PBT were each tested for their ability to inhibit the growth of two Gram(--) (Escherichia coil, Salmonella) and two Gram(+) (Bacillus subtilis, Staphylococcus aureus) microorganisms. The complex showed good antibacterial activities against the microorganisms compared with free PBT and Cu(C104)2. The interaction between the complex and calf thymus DNA in aqueous solution was investigated using electronic spectroscopy, fluorescence spectroscopy, circular dichroic spectroscopy, and viscosity measurements. Results suggest that the complex could bind to DNA by an intercalative mode. In addition, the result of agarose gel electrophoresis showed that the complex can cleave the plasmid DNA by hydroxyl radicals and singlet oxygen-like species under the condition of physiological pH and room temperature.

  3. Exploration of twisted intramolecular charge transfer fluorescence properties of trans-2-[4-(dimethylamino)styryl]benzothiazole to characterize the protein-surfactant aggregates

    Energy Technology Data Exchange (ETDEWEB)

    Muthusubramanian, Sowmiya [Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan (India); Saha, Subit Kumar, E-mail: sksaha@bits-pilani.ac.in [Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan (India)

    2012-08-15

    The characterization of aggregates of an anionic surfactant, sodium dodecyl sulphate (SDS) with bovine serum albumin (BSA) in various regions of binding isotherm of SDS to BSA with increasing concentration of the former have been done by exploring the twisted intramolecular charge transfer (TICT) fluorescence properties of a probe, trans-2-[4-(dimethylamino)styryl] benzothiazole (DMASBT). The TICT fluorescence, steady-state fluorescence anisotropy and time-resolved fluorescence of DMASBT, and the fluorescence resonance energy transfer (FRET) study reveal the characteristics of the native protein as well as the protein-surfactant aggregates viz., micropolarity, microviscosity, locations of probe, denaturation of protein in various regions of binding isotherm, and also the validation of necklace-bead model. The changes in the polarity and the viscosity of the microenvironment around the probe from one binding region of SDS to other have been reflected in the highly sensitive fluorescence properties of DMASBT. The study of FRET between the DMASBT and the tryptophan residue (Trp) of BSA has identified the locations of the probe molecule in the native protein as well as that in various BSA-SDS aggregates. The energy transfer efficiency decreases, whereas the distance between the DMASBT and the Trp residue increases with increasing concentration of SDS. The significant change in the conformations of protein molecules during the non-cooperative binding region of SDS is evidenced by the fluorescence anisotropic behavior of DMASBT in the same region. - Highlights: Black-Right-Pointing-Pointer Micropolarity and microviscosity of environment around the probe in BSA-SDS aggregates is reported. Black-Right-Pointing-Pointer Denaturation of protein is demonstrated by the TCSPC of DMASBT and FRET study. Black-Right-Pointing-Pointer Location of the probe in the native protein and BSA-SDS aggregates is identified using FRET study. Black-Right-Pointing-Pointer During unfolding of BSA

  4. APPLICATION OF BENZOTHIAZOLE AND THEIR IODIDES IN DYE SENSITIZED SOLAR CELLS%苯并噻唑及其碘盐在染料敏化太阳电池中的应用

    Institute of Scientific and Technical Information of China (English)

    杨燕珍; 桃李; 吴玉程; 史成武; 张元元

    2012-01-01

    Influence of the heterocyclic structure and heteroatom N/S of additives, benzothiazole (BT) , 2-methyl benzothiazole (MBT), 3-methyl benzothiazolium iodide (MBTI) , 2,3-dimethyl benzothiazolium iodide (DMBTI) and 4-tert-butylpyridine (TBP), on I3-/I- redox behavior and the Pt electrode/solution interface reaction was in-vestigated by cyclic voltammetry using a Pt disk ultramicroelectrode and electrochemical impedance spectroscopy. The results revealed that the apparent diffusion coefficient of I3- and I- in solution decreased with additives being added. The charge transfer resistance at the Pt electrode I electrolyte interface increased by adding BT, MBT, TBP and decreased by adding MBTI, DMBT. From the photovoltaic performance of these DSCs, it was concluded that pyridine cycle was better than benzothiazole cycle and basic N atom was better than basic S atom in these additives.%分别以苯并噻唑(BT)、2-甲基苯并噻唑(MBT)、3-甲基苯并噻唑碘(MBTI)、2,3-二甲基苯并噻唑碘(DMBTI)及4-叔丁基吡啶(TBP)作为染料敏化太阳电池(DSCs)电解质溶液中的添加剂,使用超微电极通过循环伏安法和电化学阻抗谱研究上述5种添加剂的杂环结构及杂原子N和S对电解质中I3-和I-氧化还原行为和对铂黑电极|电解质界面的影响.结果表明,随着添加剂的加入,溶液中I3-和I-扩散系数均减小;添加BT、MBT和TBP,铂黑电极|电解质的界面传输电阻Rct增大,添加MBTI和DMBTI,Rct减小.电池的光伏性能测试结果表明,添加剂中含有吡啶环的结构优于苯并噻唑环,含有碱性N原子优于碱性S原子.

  5. Effect of 2-Amino-Benzothiazole Zinc Complex on the Growth and Development of Cotton Bollworm%2-氨基苯并噻唑锌配合物对棉铃虫生长发育的影响

    Institute of Scientific and Technical Information of China (English)

    张海玲; 王树芳; 张优优; 王玉平; 柴连琴

    2012-01-01

    选取数百条正常三龄棉铃虫,分成5组,分别饲喂含不同剂量的2-氨基苯并噻唑锌配合物的人工配制饲料,期间测量每条虫的体重,直至生长到六龄使用血细胞计数板对血细胞进行计数,再测定血浆中的T-SOD活性.结果显示:与对照组相比,饲喂含低剂量2-氨基苯并噻唑锌配合物饲料的棉铃虫的血细胞数目较多,T-SOD活力较强;饲喂含高剂量配合物饲料的棉铃虫受到严重抑制,几乎处于不生长状态.以上结果表明低剂量2-氨基苯并噻唑锌配合物对棉铃虫生长发育有促进作用,而高剂量的则有抑制作用.%Hundreds of normal third instar cotton bollworms were selected and divided into five groups. They were fed with the artificial feed with different doses of 2-amino benzothiazole zinc complex solution. During the period, the weight of each cotton bollworm was measured. The number of the blood cells was calculated, using the blood cell counting plate. Then the activity of the T-SOD was determinated. Compared with the control group, the cotton bollworms fed with low dose of 2-amino benzothiazole zinc complex feed have more blood cells and a higher activity of T-SOD. Cotton bollworms fed with high dose of the complex were seriously inhibited and almost no growth in the state was shown. It suggested that low dose of 2-amino benzothiazole zinc complex promoted the growth and development of cotton bollworms, while high dose inhibited that.

  6. Competitive bulk liquid membrane transport of Co(Ⅱ),Ni(Ⅱ),Zn(Ⅱ),Cd(Ⅱ),Ag(Ⅰ),Cu(Ⅱ)and Mn(Ⅱ),cations using 2,2'-dithio(bis)benzothiazole as carrier

    Institute of Scientific and Technical Information of China (English)

    A.Nezhadali; N.Rabani

    2011-01-01

    A series of competitive metal-ion transport experiments has been performed.Each involved transport from an aqueous source phase across an organic membrane phase into an aqueous receiving phase.The source phase contained equimolar concentration of Co(Ⅱ),Ni(Ⅱ),Zn(Ⅱ),Cd(Ⅱ),Ag(Ⅰ),Cu(Ⅱ)and Mn(Ⅱ)metal cations.The transport experiments of metal cations were carried out by2,2'-dithio(bis)benzothiazole(DTB)in chloroform(CHCl3).The source phase being buffered at range pH of 4-6.5 and receiving phase being buffered at pH 3.The obtained results show that the selectivity and the efficiency of Ag(Ⅰ)transport from aqueous solutions are observed in this investigation.The effect of concentration of palmitic acid in the transport efficiency of Ag(Ⅰ)ion was also conformed.

  7. "一锅煮"合成新型含吡唑与苯并噻唑环的α-氨基膦酸酯衍生物%One-pot Synthesis of Novel α-Aminophosphonate Derivatives Containing Pyrazole and Benzothiazole

    Institute of Scientific and Technical Information of China (English)

    李建平; 仇记宽; 李会娟

    2011-01-01

    A series of novel α-aminophosphonates derivatives containing pyrazole and benzothiazole were synthesized from substituted pyrazole aldehyde, 2-aminobenzothiazole and diethylphosphone under microwave-assisted without catalyst and solvent. The structures were characterized by 1H NMR,13C NMR and MS.%在微波辅助、无溶剂、无催化剂条件下,以取代吡唑甲醛,2-氨基苯并噻唑和亚磷酸二乙酯为原料,"一锅煮"合成了6个新型含吡唑与苯并噻唑环的α-氨基膦酸酯衍生物,其结构经1H NMR,13C NMR和MS表征.

  8. Poly[[μ2-(1Z,N′E-2-(1,3-benzothiazol-2-ylsulfanyl-N′-(2-oxidobenzylidene-κ2O:Oacetohydrazidato-κ2O,N′](pyridine-κNcopper(II

    Directory of Open Access Journals (Sweden)

    Vasily I. Pekhnyo

    2011-01-01

    Full Text Available In the title compound, [Cu(C16H11N3O2S2(C5H5N]n, the CuII atom displays a square-pyramidal CuN2O3 coordination geometry with strong elongation in the vertex direction. The hydrazone molecule is coordinated to the CuII atom in a tridentate manner in the enolic form, creating five- and six-membered chelate metallarings. The pyridine molecule completes the square-planar base of the copper coordination environment. The crystal structure displays zigzag polymeric Cu—O—Cu chains along [001]. Several weak π–π interactions between benzothiazole rings were found in the same direction [centroid–centroid distances = 3.7484 (16, 3.7483 (16, 3.6731 (17 and 3.7649 (17 Å].

  9. 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.

  10. 苯并噻唑希夫碱类化合物的合成及其与β-淀粉样蛋白结合性能的研究%Synthesis of benzothiazole derivatives and their binding characteristics with β-amyloid

    Institute of Scientific and Technical Information of China (English)

    周琳; 甘昌胜; 汪昊曙; 赵珍珍; 潘见

    2012-01-01

    Alzheimer's disease (AD) is a progressive neurodegenerative disease endangering human health seriously. Recent reports have revealed that β-amyloid aggregates play a key role in the pathogenesis of AD. Thus, targeting the Aβ plaques benzothiazole derivatives were synthesized with the scaffold of the most promising imaging agent PIB ([11C]-6-OH-BTA-l, ["C]-2-(4-(raethylamino)phenyl)-6-hydroxybenzothiazole) and C=N as linker to study the binding characteristics with the target protein through surface plasmon resonance (SPR) technique. These derivatives were synthesized through simple yet effective method with high yields and characterized by 'H NMR and FUR. The binding properties {KD} were determined with Biacore X-100 instrument according to the fitting-plot curve. Compounds 3a and 3f showed high binding affinity for Aβ1-40. The results suggest that benzothiazole derivatives could be served as a scaffold to develop novel β-amyloid imaging agents for the diagnosis of AD.

  11. Investigation on Synthesis and Photostabilities of Novel Asymmetric Benzothiazole Trimethine Cyanine Dyes%新型不对称苯并噻唑三次甲基菁染料的合成及光稳定性研究

    Institute of Scientific and Technical Information of China (English)

    陈秀英; 郭琳; 郑昌戈; 高海燕; 王海军; 张丹

    2012-01-01

    合成了系列杂环氮原子具有不同取代基的不对称苯并噻唑三次甲基菁染料,染料结构经过质谱、1H NMR表征,测试了染料在乙醇中的吸收和荧光发射光谱,染料的最大吸收值和荧光发射值分别在628~631和662~666 nm之间.染料在溶剂中几乎无荧光,可以极大的降低染料自身的荧光背景干扰.染料的光降解实验表明:喹啉环 上辛烷基取代和噻唑环上苄基取代时,染料的光稳定性最强.染料8a~8d的光降解速率常数分别为6.38×10-4,12.5×10-4,2.68×10-4和6.30×10-4 mol·min-1.循环伏安实验法测试了染料的氧化电位.%Novel asymmetric trimethine benzothiazole cyanine dyes with different N-substituents were synthesized and characterized by MS and 'H NMR techniques. The maximums of absorption and emission spectra of the dyes in ethanol were in the range of 628~631 and 662~666 nm, respectively. The dyes were almost non-fluorescent in solvents, which can reduce the background interference greatly. The photodegradation experiment showed that the octyl group on quinoline ring and benzyl group on benzothiazole ring improved the photostabilites of the dyes obviously. The rate constants of photoreaction of the dyes 8a~8d were 6.38× 10-4, 12.5× 10-4, 2.68×10-4 and 6.30×10 4 mol·min-1, respectively. Oxidation potentials were determined by cyclic voltammetry.

  12. The characterization of electroplex generated from the interface between 2-(4-trifluoromethyl-2-hydroxyphenyl)benzothiazole] zinc and N,N'-diphenyl-N,N'- bis(1-naphthyl)-(1,1'-biphenyl)-4,4'-diamine

    Science.gov (United States)

    Zhang, Ye; Hao, Yuying; Meng, Weixin; Xu, Huixia; Wang, Hua; Xu, Bingshe

    2012-03-01

    The electroplex between (2-(4-trifluoromethyl-2-hydroxyphenyl)benzothiazole) zinc [Zn(4-TfmBTZ)2] as an electron-acceptor and N,N'-diphenyl-N,N'-bis(1-naphthyl)-(1,1'-biphenyl)-4,4'-diamine (NPB) as an electron-donor was characterized by bilayer, blend, and multilayer quantum-well (MQW) device, respectively. The blend composition and quantum-well number are effective parameters for tuning electroluminescence color. White light with high color purity and color rendering index (CRI) was observed from these devices based on Zn(4-TfmBTZ)2/NPB. Moreover, the blend and MQW devices all exhibit high operation stability, hence excellent color stability. For the device with 5 mol% NPB in blend layer, its Commission International Del'Eclairage (CIE) coordinate region is x=0.28-0.31, y=0.33-0.35 and CRI is 83.3-91.2 at 5-9 V. For MQW structure device with NPB of 60 nm thickness, its CIE coordinate region is x=0.29-0.32, y=0.31-0.34 and CRI=87.9-92.5 at 10-15 V. Such high color stability and purity and CRI, being close to ideal white light, are of current important for white OLED.

  13. A quick, easy, cheap, effective, rugged and safe extraction method followed by liquid chromatography-(Orbitrap) high resolution mass spectrometry to determine benzotriazole, benzothiazole and benzenesulfonamide derivates in sewage sludge.

    Science.gov (United States)

    Herrero, Pol; Borrull, Francesc; Pocurull, Eva; Marcé, Rosa M

    2014-04-25

    A Quick, Easy, Cheap, Effective, Rugged and Safe (QuEChERS) extraction method followed by liquid chromatography-(Orbitrap) high resolution mass spectrometry was developed for the simultaneous determination of five benzotriazole, four benzothiazole and five benzenesulfonamide derivates in sewage sludge. While the method was being developed, several buffers and dispersive solid-phase extraction clean-up (dSPE) sorbents were tested. Citrate buffer and Z-sep+ (zirconium-based sorbent) were the most effective extraction buffer and dSPE clean-up material. The absolute recoveries were higher than 80% for all compounds (100ng/g (d.w.)) and the matrix effect was less than -20% for most compounds. The limits of detection were between 0.5 and 10ng/g (d.w.) and the limits of quantification (LOQ) were between 1 and 25ng/g (d.w.). Repeatability and reproducibility were lower than 15% (%RSD, n=5). Several sludge samples from five sewage treatment plants in Catalonia were analysed and the most abundant compounds were 2-hydroxybenzothiazole (

  14. Synthesis and Anti-inflammatory Activity of Novel Benzimidazole (Benzothiazole) Phenylursolate%新型熊果酸苯并咪(噻)唑连苯酯合成及抗炎活性测定

    Institute of Scientific and Technical Information of China (English)

    李财虎; 杨聪玲; 张宽; 石万棋; 李剑忠; 李颖; 尹述凡

    2012-01-01

    以熊果酸、取代苯甲醛和邻苯二胺或邻氨基苯硫酚为原料,合成了一系列熊果酸苯并咪(噻)唑连苯酯衍生物4a~4h,8个新化合物均未见文献报道,其结构经1H NMR,IR和HRMS加以确认,并对4a~4h进行药理活性筛选,结果表明,化合物4d (150 mg·kg-1),4g (150 mg·kg-1)等具有良好抗炎活性.%A novel series of the benzimidazole or benzothiazole phenyl ester derivatives of ursolic acid 4a~4h were prepared via ursolic acid, substituted benzaldehyde, and o-phenylendiamine or 2-aminothiophenol. The compounds were structurally confirmed by 'H NMR, 1R and HRMS techniques. The preliminary bioassay test demonstrated that compounds 4d and 4g had potent anti-inflammatory activity.

  15. 含均三嗪结构苯并噻唑类化合物的合成和晶体结构%Synthesis of Benzothiazole Compound Containing s-Triazine Structure and the Crystal Structure

    Institute of Scientific and Technical Information of China (English)

    韩燕

    2014-01-01

    以三聚氯氰等为原料合成了一种含均三嗪结构苯并噻唑类化合物(HY),并通过X射线单晶衍射对其结构进行了表征。结果表明:H Y属于单斜晶体,空间群为 P2(1)/n。晶胞参数为:Z=4,a=1.4278(17) nm ,b=1.6690(2)nm ,c=1.44842(17) nm ,α=90°,β=102.707(2)°,γ=90°,V =3.3655(7) nm3;R1=0.0755;w R2=0.2161。%A benzothiazole compound containing s-triazine structure(HY) was synthesized with the materials of cya-nuric chloride and others .The crystal structure was represented by single-crystal X-ray diffraction .The results showed that HY belonged to monoclinic system ,and its space group is P2(1)/n .The cell parameters were Z=4 ,a=1.427 18(17) nm ,b=1.669 0(2) nm ,c=1.448 42(17) nm ,α=90° ,β=102.707(2)° ,γ=90° ,V=3.365 5(7) nm3 ;R1 =0.075 5 , w R2 =0.216 1 .

  16. Syntheses, Characterization, and Antimicrobial Screening of N-(benzothiazol-2-ylbenzenesulphonamide and its Cu(I, Ni(II, Mn(II, Co(II, and Zn(II Complexes

    Directory of Open Access Journals (Sweden)

    N. L. Obasi

    2012-01-01

    Full Text Available N-(benzothiazol-2-ylbenzenesulphonamide (BS2ABT was synthesized by the condensation (by refluxing of 2-aminobenzothiazole and benzenesulphonylchloride in acetone at 140ºC. The resulting crude precipitates were recrystallized from dimethylformamide (DMF. Five metal complexes of copper(I, nickel(II, manganese(II, cobalt(II and zinc(II of the ligands were synthesized. The compounds were characterized using magnetic susceptibility measurements, UV/VIS spectrophotometry, infra red, proton and 13C nmr spectroscopies. The antimicrobial tests of the ligands and its metal complexes were carried out on both multi-resistant bacterial strains isolated under clinical conditions and cultured species using agar-well diffusion method. The multi-resistant bacterial strains used were Escherichia coli, Proteus species, Pseudomonas aeroginosa and Staphylococcus aureus which were isolated from dogs. The culture species were Pseudomonas aeruginosa (ATCC 27853, Escherichia Coli (ATCC 25922 Staphylococcus aureus (ATCC 25923, and the fungi, Candida krusei (ATCC 6258 and Candida albicans (ATCC 90028. The tests were both in vitro and in vivo. Thus the Inhibition Zone Diameter (IZD, the Minimum Inhibitory Concentration (MIC, and the Lethal and Effective Concentrations (LC50 and EC50 were determined. The antimicrobial activities of the compounds were compared with those of Ciprofloxacin and trimethoprim-sulphamethoxazole as antibacterial agents and Fluconazole as an antifungal drug. All the compounds showed varying activities against the cultured typed bacteria and fungi used. However, they were less active than the standard drugs used except Fluconazole which did not show any activity against Candida krusei (ATCC 6258 but most of the compounds synthesized were very active against it. The Lethal Concentration (LC50 ranged from 26.25±4.9-1833.88±186.92 ppm. These are within the permissible concentrations.

  17. Crystal structure of the salt bis(triethanolamine-κ4N,O,O′,O′′cadmium bis[2-(2-oxo-2,3-dihydro-1,3-benzothiazol-3-ylacetate

    Directory of Open Access Journals (Sweden)

    Jamshid Mengnorovich Ashurov

    2016-04-01

    Full Text Available The reaction of 2-(2-oxo-2,3-dihydro-1,3-benzothiazol-3-ylacetic acid (NBTA and triethanolamine (TEA with Cd(CH3OO2 resulted in the formation of the title salt, [Cd(C6H15NO32](C9H6NO3S2. In its crystal structure, the complex cation [Cd(TEA2]2+ and two independent NBTA− units with essentially similar geometries and conformations are present. In the complex cation, each TEA molecule behaves as an N,O,O′,O′′-tetradentate ligand, giving rise to an eight-coordinate CdII ion with a bicapped trigonal–prismatic configuration. All ethanol groups of each TEA molecule form three five-membered chelate rings around the CdII ion. The Cd—O and Cd—N distances are in the ranges 2.392 (2–2.478 (2 and 2.465 (2–2.475 (3 Å, respectively. O—H...O hydrogen bonds between the TEA hydroxy groups and carboxylate O atoms connect cationic and anionic moieties into chains parallel to [110]. Each NBTA− anion is additionally linked to a symmetry-related anion through π–π stacking interactions between the benzene and thiazoline rings [minimum centroid-to-centroid separation = 3.604 (2 Å]. Together with additional C—H...O interactions, these establish a double-layer polymeric network parallel to (001.

  18. Ethylene glycol modified 2-(2‧-aminophenyl)benzothiazoles at the amino site: the excited-state N-H proton transfer reactions in aqueous solution, micelles and potential application in live-cell imaging

    Science.gov (United States)

    Liu, Bo-Qing; Chen, Yi-Ting; Chen, Yu-Wei; Chung, Kun-You; Tsai, Yi-Hsuan; Li, Yi-Jhen; Chao, Chi-Min; Liu, Kuan-Miao; Tseng, Huan-Wei; Chou, Pi-Tai

    2016-03-01

    Triethylene glycol monomethyl ether and poly(ethylene glycol) monomethyl ether modified 2-(2‧-aminophenyl)benzothiazoles, namely ABT-P3EG, ABT-P7EG and ABT-P12EG varied by different chain length of poly(ethylene glycol) at the amino site, were synthesized to probe their photophysical and bio-imaging properties. In polar, aprotic solvents such as CH2Cl2 ultrafast excited-state intramolecular proton transfer (ESIPT) takes place, resulting in a large Stokes shifted tautomer emission in the green-yellow (550 nm) region. In neutral water, ABT-P12EG forms micelles with diameters of 15  ±  3 nm under a critical micelle concentration (CMC) of ~80 μM, in which the tautomer emission is greatly enhanced free from water perturbation. Cytotoxicity experiments showed that all ABT-PnEGs have negligible cytotoxicity against HeLa cells even at doses as high as 1 mM. Live-cell imaging experiments were also performed, the results indicate that all ABT-PnEGs are able to enter HeLa cells. While the two-photon excitation emission of ABT-P3EG in cells cytoplasm shows concentration independence and is dominated by the anion blue fluorescence, ABT-P7EG and ABT-P12EG exhibit prominent green tautomer emission at  >  CMC and in part penetrate to the nuclei, adding an additional advantage for the cell imaging.

  19. Discovery of 7-methoxy-6-[4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-5-yl]-1,3-benzothiazole (TASP0382088): a potent and selective transforming growth factor-β type I receptor inhibitor as a topical drug for alopecia.

    Science.gov (United States)

    Amada, Hideaki; Asanuma, Hajime; Koami, Takeshi; Okada, Atsushi; Endo, Mayumi; Ueda, Yasuji; Naruse, Takumi; Ikeda, Akiko

    2013-01-01

    7-Methoxy-6-[4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-5-yl]-1,3-benzothiazole 11 (TASP0382088) was synthesized and evaluated as transforming growth factor-β (TGF-β) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitor. Compound 11, a potent and selective ALK5 inhibitor, exhibited good enzyme inhibitory activity (IC50=4.8 nM) as well as inhibitory activity against TGF-β-induced Smad2/3 phosphorylation at a cellular level (IC50=17 nM). The introduction of a methoxy group to the benzothiazole ring in 1 and the break up of the planarity between the imidazole ring and the thiazole ring improved the solubility in the lotion base of 11. Furthermore, the topical application of 3% 11 lotion significantly inhibited Smad2 phosphorylation in mouse skin at 8 h after application (71% inhibition, compared with vehicle-treated animals).

  20. 苯并噻唑类核酸分子荧光探针的合成及光谱性质%Synthesis and Spectral Properties of Benzothiazole Cyanine Dyes for Nucleic Acid Fluorescence Probe

    Institute of Scientific and Technical Information of China (English)

    陈秀英; 郭琳; 郑昌戈; 高海燕; 安文

    2012-01-01

    设计合成了3种两端杂环氮原子上具有不同取代基的苯并噻唑类不对称三甲川菁染料,并对染料的结构进行了表征.测试了染料在乙醇中的吸收和荧光发射光谱,染料的最大吸收值和荧光发射值分别在629 ~635 nm和656 ~672nm之间.染料8、9和10的斯托克斯位移分别为23、37和27nm.染料在溶剂中基本无荧光,荧光量子产率小于0.021,可以极大的降低染料自身的荧光背景干扰.染料的光降解实验表明,两端杂环氮原子苄基取代后可以明显增强染料的光稳定性.测试循环伏安曲线得到染料的氧化电位分别为0.535、0.456和0.399 V,氧化电位越大,光降解速率常数越小,与光降解实验得到的降解速率常数结果一致.%Three novel asymmetric trimethine benzothiazole cyanine dyes with different iV-substituents were designed and synthesized. The structures of the dyes were characterized, and the maximums of the spectral absorption and emission of the dyes in ethanol were found in the range of 629 ~ 635 nm and 656 ~ 672 nm. The Stokes shift values for dyes 8, 9 and 10 were 23, 37 and 27 nm, respectively. The dyes were almost non-fluorescent in solvents with a low fluorescent quantum yield of less than 0. 021 in ethanol, which could reduce the background interference greatly. The photodegradation experiment showed that the introduction of benzyl group on the heteroaromatic rings improved the photostabilites of the dyes obviously.' The oxidizing potentials for the dyes 8, 9 and 10 were at 0. 535, 0.456 and 0. 399 V ts SCE, which was consistent with the data of photodegradation experiment.

  1. CHITOSAN AND BENZOTHIAZOLE COMPOUND AGENTS PROMOTE BROWN SPOT DISEASE-RESISTANCE AND MASS GROWTH OF CUT Chrysanthemum morifolium 'Jinba'%壳聚糖与苯并噻唑复配剂对切花菊‘神马’生长与抗病性的影响

    Institute of Scientific and Technical Information of China (English)

    李江文; 李俊香; 曾海鹏; 马男; 赵梁军

    2012-01-01

    以切花菊‘神马’为材料,喷施不同复配比例的诱抗剂(壳聚糖和苯并噻唑)和蔗糖、KH2PO4,观测各处理对菊花的生长量、相关防御酶活性及褐斑病抗性的影响。结果表明:与对照相比,分别用诱抗剂300mg.L-1壳聚糖或100mg.L-1苯并噻唑,与3%蔗糖、0.3%KH2PO4复配后喷施菊花植株,能显著增加‘神马’的株高与茎粗,提高叶片的POD、PPO与PAL酶活性,降低褐斑病病情指数,提高诱抗效果,且壳聚糖与苯并噻唑的作用效果相似,二者均可作为防治菊花褐斑病的药剂。%Two self-defense inducers of chitosan and benzothiazole with sucrose and KH2PO4 were applied to evaluate the effects of compound agents on the growth of cut Chrysanthemum morifolium 'Jinba',and mass growth,activities of related defensive enzymes and disease-resistance to brown spot were measured.Results showed that,when the compound agents of 300mg﹒L-1 chitosan or 100 mg﹒L-1 benzothiazole compounding with 3% of sucrose and 0.3% of KH2PO4 were sprayed on chrysanthemum,plant height,stem diameter,activities of POD,PPO and PAL in leaves,and effects of induced resistance were significantly promoted,and brown spot disease indexes were significantly reduced.The effects of chitosan were observed similar to that of benzothiazole.

  2. Theoretical studies of molecular structure, electronic structure, spectroscopic properties and the ancillary ligand effect: A comparison of tris-chelate ML 3-type and ML 2X-type species for gallium(III) complexes with N, O-donor phenolic ligand, 2-(2-hydroxyphenyl)benzothiazole

    Science.gov (United States)

    Tong, Yi-Ping; Lin, Yan-Wen

    2011-02-01

    Two Ga(III) complexes with main ligand, 2-(2-hydroxyphenyl)benzothiazole (HL'), namely mixed-ligand ML 2X-type [GaL' 2X'] ( 1) (HX' = acetic acid, as ancillary ligand) and the meridianal tris-chelate [GaL' 3] ( 2) have been investigated by the density functional theory (DFT/TDDFT) level calculations. Both 1 and 2 can be presented as a similar "mixed-ligand ML 2X-type" species. The molecular geometries, electronic structures, metal-ligand bonding property of Ga-O (N) (main ligand), Ga-O (N) (ancillary ligand) interactions, and the ancillary ligand effect on their HOMO-LUMO gap, their absorption/emission property, and their absorption/emission wavelengths/colors for them have been discussed in detail based on the orbital interactions, the partial density of states (PDOS), and so on. The current investigation also indicates that it is quite probable that by introduction of different ancillary ligands, a series of new mixed-ligand ML 2X-type complexes for group 13 metals can be designed with their absorption/emission property and the absorption/emission wavelengths and colors being tuned.

  3. Analysis of the Intermediate of 2-Hydrazino-4-methyl-1,3-benzothiazole of Tricyclazole by HPLC%三环唑中间体4-甲基-2-肼基苯并噻唑的液相色谱分析

    Institute of Scientific and Technical Information of China (English)

    陆学云; 唐勤桂

    2014-01-01

    A method was described for quantitative analysis of 2-hydrazino-4-methyl-1,3-benzothiazole by HPLC using methanol, water and phosphoric acid (volume ratio of 35︰65︰0.026, pH=2.85) as mobile phase, C 18 column and UV detector at 231. The results showed that the linear correlation coefficient of the method was 0.999 2, the standard deviation was 0.15, the variation coefficient was 0.16%, and the average recovery was 98.3%.%采用高效液相色谱法,使用C 18柱和紫外检测器,以甲醇+水+磷酸(体积比35∶65∶0.026,pH=2.85)为流动相,在231 nm波长下,对4-甲基-2-肼基苯并噻唑进行外标法定量测定。方法的线性相关系数为0.9992,标准偏差为0.15,变异系数为0.16%,平均回收率为98.3%。

  4. Evaluation of 6-chloro-N-[3,4-disubstituted-1,3-thiazol-2(3H)-ylidene]-1,3-benzothiazol-2-amine Using Drug Design Concept for Their Targeted Activity Against Colon Cancer Cell Lines HCT-116, HCT15, and HT29

    Science.gov (United States)

    Zhu, Ming-Li; Wang, Cui-Yue; Xu, Cheng-Mian; Bi, Wei-Ping; Zhou, Xiu-Ying

    2017-01-01

    Background Colorectal adenocarcinoma is the second leading cause of cancer-related death in the world. The stage of the disease is related to the survival of the patient, and in early phases surgery is the main modality of treatment. The main aim of modern medicinal chemistry is to synthesize small molecules via drug designing, especially by targeting tumor cells. Material/Methods A new series of 19 compounds containing benzothiazole and thiazole were designed. Molecular docking studies were performed on the designed series of molecules. Compounds showing good binding affinity towards the EGFR receptor were selected for synthetic studies. Characterization of the synthesized compounds was done by FTIR, 1HNMR, Mass and C, H, N, analysis. Results The anticancer evaluation of the synthesized compounds was done at NIC, USA at a single dose against colon cancer cell lines HCT 116, HCT15, and HC 29. The active compounds were further evaluated for the 5-dose testing. Compounds were designed by using docking analysis. To ascertain the interaction of EGFR tyrosine kinase binding, energy calculation was used. Conclusions The results of the present study indicate that the designed compounds show good activity against colon cancer cell lines, which may be further studied to design new potential molecules. PMID:28259893

  5. Tris(2-hydroxyethylammonium 1,3-benzothiazole-2-thiolate

    Directory of Open Access Journals (Sweden)

    Ji-Qin Zhu

    2009-07-01

    Full Text Available In the title compound, C6H16NO3+·C7H4NS2−, the cations and anions are connected by O—H...N and O—H...S hydrogen bonding. Weak C—H...O hydrogen bonding between adjacent cations helps to stabilize the crystal structure.

  6. Synthesis and herbicidal activities of benzothiazole N,O-acetals.

    Science.gov (United States)

    Ji, Zhiqin; Zhou, Fengxing; Wei, Shaopeng

    2015-10-01

    A new series of N,O-acetals were prepared via a simple one-pot reaction by the condensation of 2-amino-methybenzothiazole with aldehydes and alcohols. The title compounds were obtained in moderate to good yields in the presence of acid catalyst. Bioassay results indicated that some synthesized compounds had good herbicidal activity against both dicotyledon and monocotyledon weeds. This investigation provided a new type of herbicidal lead compounds, as well as its facile preparation method.

  7. 2-[(2-Hydroxy-1-naphthylmethyleneamino]-1,3-benzothiazole

    Directory of Open Access Journals (Sweden)

    Daqi Wang

    2008-10-01

    Full Text Available In the title compound, C18H12N2OS, the dihedral angle between the mean planes of the aromatic ring systems is 7.26 (8°. There is an intramolecular O—H...N hydrogen bond, forming a six-membered ring. In the crystal structure, intermolecular C—H...N hydrogen bonds link the molecules into a one-dimensional chain.

  8. New Conjugated Benzothiazole-N-oxides: Synthesis and Biological Activity

    Directory of Open Access Journals (Sweden)

    Pavlína Foltínová

    2009-12-01

    Full Text Available Eleven new 2-styrylbenzothiazole-N-oxides have been prepared by aldol – type condensation reactions between 2-methylbenzothiazole–N-oxide and para-substituted benzaldehydes. Compounds with cyclic amino substituents showed typical push-pull molecule properties. Four compounds were tested against various bacterial strains as well as the protozoan Euglena gracilis as model microorganisms. Unlike previously prepared analogous benzothiazolium salts, only weak activity was recorded.

  9. Propyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-carboxylate

    Directory of Open Access Journals (Sweden)

    Xiang-hui Wang

    2011-09-01

    Full Text Available The title compound, C11H11NO3S, was synthesized by the reaction of benzo[d]isothiazol-3(2H-one with propyl carbonochloridate in toluene. The benzoisothiazolone ring system is approximately planar with a maximum deviation from the mean plane of 0.0226 (14 Å for the N atom. Weak intermolecular C—H...O hydrogen bonding occurs in the crystal structure.

  10. A new hydroxynaphthyl benzothiazole derived fluorescent probe for highly selective and sensitive Cu2 + detection

    Science.gov (United States)

    Tang, Lijun; He, Ping; Zhong, Keli; Hou, Shuhua; Bian, Yanjiang

    2016-12-01

    A new reactive probe, 1-(benzo[d]thiazol-2-yl)naphthalen-2-yl-picolinate (BTNP), was designed and synthesized. BTNP acts as a highly selective probe to Cu2 + in DMSO/H2O (7/3, v/v, Tris-HCl 10 mM, pH = 7.4) solution based on Cu2 + catalyzed hydrolysis of the picolinate ester moiety in BTNP, which leads to the formation of an ESIPT active product with dual wavelength emission enhancement. The probe also possesses the advantages of simple synthesis, rapid response and high sensitivity. The pseudo-first-order reaction rate constant was calculated to be 0.205 min- 1. Moreover, application of BTNP to Cu2 + detection in living cells and real water samples was also explored.

  11. 6-Nitro-1,3-benzothiazole-2(3H-thione

    Directory of Open Access Journals (Sweden)

    Qi-Ming Qiu

    2013-02-01

    Full Text Available In the title molecule, C7H4N2O2S2, the nitro group is twisted by 5.5 (1° from the plane of the attached benzene ring. In the crystal, N—H...S hydrogen bonds link pairs of molecules into inversion dimers, which are linked by weak C—H...O interactions into sheets parallel to (101. The crystal packing exhibits short intermolecular S...O contacts of 3.054 (4 Å and π–π interactions of 3.588 (5 Å between the centroids of the five- and six-membered rings of neighbouring molecules.

  12. Ethyl 2-(tert-butoxycarbonylamino-1,3-benzothiazole-6-carboxylate

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    Can Lei

    2010-04-01

    Full Text Available In the crystal of the title compound, C15H18N2O4S, inversion dimers are formed by intermolecular N—H...N hydrogen bonds and weak C—H...O contacts. These dimers stack up along [100] through inversion-related π–π interactions between thiazole rings [centroid–centroid distance = 3.790 (2 Å] and the thiazole and benzene rings [centroid–centroid distance = 3.845 (2 Å] and C—H...π contacts.

  13. Synthesis and Inhibition Effects on 5-HT{sub 6} Receptor of Benzothiazole Derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Hayat, Faisal; Yoo, Euna; Choo, Heayoung Park [Ewha Womans Univ., Seoul (Korea, Republic of); Rhim, Hyewhon [Korea Institute of Science and Technology, Seoul (Korea, Republic of)

    2013-02-15

    A novel series of aryl sulfonylpiperazine derivatives (5-15) were synthesized as 5-HT{sub 6} ligands. In vitro assay was evaluated by measuring the 5-HT-induced Ca{sup 2+} increases using HeLa cell line expressing the cloned human 5-HT{sub 6} receptor, and the compound 13 showed potent 5-HT{sub 6} receptor antagonistic effect with IC{sub 50} value of 3.9 μM. Compound 13 also showed good selectivity on the 5-HT{sub 6} over 5-HT{sub 4} and 5-HT{sub 7} receptors.

  14. Methyl 2-[2-(tert-butoxycarbonylamino-1,3-benzothiazole-6-carboxamido]acetate

    Directory of Open Access Journals (Sweden)

    Dan Gao

    2012-01-01

    Full Text Available In the title compound, C16H19N3O5S, the dihedral angle between the benzene ring and the carbonylamino group is 18.18 (2°. In the crystal, molecules form centrosymmetric dimers via pairs of N—H...N hydrogen bonds. The dimers are connected via N—H...O hydrogen bonds into a three-dimensional network..

  15. Assessment of interactions between four proteins and benzothiazole derivatives by DSC and CD

    Energy Technology Data Exchange (ETDEWEB)

    Hassan, Natalia [Soft Matter and Molecular Biophysics Group, Department of Applied Physics, Faculty of Physics, Campus Vida, University of Santiago de Compostela, E-15782 Santiago de Compostela (Spain); Verdes, Pedro V., E-mail: pedro.vazquez@usc.e [Soft Matter and Molecular Biophysics Group, Department of Applied Physics, Faculty of Physics, Campus Vida, University of Santiago de Compostela, E-15782 Santiago de Compostela (Spain); Ruso, Juan M. [Soft Matter and Molecular Biophysics Group, Department of Applied Physics, Faculty of Physics, Campus Vida, University of Santiago de Compostela, E-15782 Santiago de Compostela (Spain)

    2011-03-15

    The thermal denaturation of ovalbumin, lysozyme, myoglobin and fibrinogen at different BTS concentrations have been investigated using differential scanning calorimetry (DSC) and circular dichroism (CD) spectroscopy. Thermodynamic parameters: melting temperatures (T{sub m}), calorimetric enthalpy ({Delta}H), van't Hoff enthalpy ({Delta}H{sub v}) were obtained for all the systems under study. Thermal denaturation of the four proteins was completely irreversible. Changes in the protein conformation due to the adsorption of BTS molecules have been monitored by using UV-CD spectra. Greater changes in {alpha}-helical contents correspond with the BTS higher concentrations. The lysozyme denaturation temperature increases at low concentrations BTS indicating that BTS acts as a structure stabilizer; meanwhile it acts as a destabilizer at higher concentrations in all the proteins studied. The major effect is observed in the case of myoglobin, the protein with the highest {alpha}-helical secondary structure (75%).

  16. Synthesis and Biological Evaluation of Novel Benzothiazole Derivatives as Potential Anticonvulsant Agents

    Directory of Open Access Journals (Sweden)

    Da-Chuan Liu

    2016-02-01

    Full Text Available New benztriazoles with a mercapto-triazole and other heterocycle substituents were synthesized and evaluated for their anticonvulsant activity and neurotoxicity by using the maximal electroshock (MES, subcutaneous pentylenetetrazole (scPTZ, and rotarod neurotoxicity (TOX tests. Among the compounds studied, compound 2-((1H-1,2,4-triazol-3-ylthio-N-(6-((3-fluorobenzyl oxybenzo[d]thiazol-2-ylacetamide (5i and 2-((1H-1,2,4-triazol-3-ylthio-N-(6-((4-fluorobenzyloxy benzo[d] thiazol-2-ylacetmide (5j were the most potent, with an ED50 value of 50.8 mg/kg and 54.8 mg/kg in the MES test and 76.0 mg/kg and 52.8 mg/kg in the scPTZ seizures test, respectively. They also showed lower neurotoxicity and, therefore a higher protective index. In particular, compound 5j showed high protective index (PI values of 8.96 in the MES test and 9.30 in the scPTZ test, which were better than those of the standard drugs used as positive controls in this study.

  17. 2-Mercapto Benzothiazole%2-巯基苯并噻唑

    Institute of Scientific and Technical Information of China (English)

    李斌; 陈元春

    2005-01-01

    介绍橡胶硫化促进剂2-巯基苯并噻唑的物理性质和主要的制备方法.简要评述了2-巯基苯并噻唑在我国和日本的生产及需求现状,同时概述了2-巯基苯并噻唑作为促进剂的应用范围及其国内外价格.

  18. 3-(Propan-2-yloxy-1,2-benzothiazole 1,1-dioxide

    Directory of Open Access Journals (Sweden)

    Muneeb Hayat Khan

    2012-02-01

    Full Text Available In the title compound, C10H11NO3S, the benzisothiazole ring system is almost planar [maximum deviation = 0.030 (1 Å for the S atom]. The isopropoxy group is almost in the plane of the benzisothiazole ring system [N—C—O—C = 4.5 (2°] with one of its methyl groups in an antiperiplanar orientation relative to the benzisothiazole ring system [C—C—O—C = −162.0 (2°].

  19. Synthesis of New Benzimidazole and Benzothiazole Disulfide Metal Complexes as G-quadruplex Binding Ligands.

    Science.gov (United States)

    Saour, Kawkab; Lafta, Dunya

    2016-01-01

    Compounds that can bind and stabilize non-canonical DNA structures are named quadruplex and are of interest in anticancer drug design due to their selective inhibitions of telomerase and consequent effects on cell proliferation. In this study, we report novel Co/Cu [II] complex compounds as G-quadruplex DNA binding ligands. The results from the preliminary assay indicated that the introduction of a positively charged 6-membered tail to the aromatic terminal group of benzimidazole significantly enhanced the binding affinity with the quadruplex and exhibited anti-telomerase activity. These derivatives showed significant selectivities for the telomeric quadruplex over duplex nucleic acids. The stabilization of non-canonical forms estimated with the FRET DNA technology using different sequences, such as F21T, c-kit1 and c-kit2, in cancer cell lines were assessed. Three members of this family showed to be very selective in stabilizing one particular G-quadruplex.

  20. {2-[(1,3-Benzothiazol-2-ylmethoxy]-5-fluorophenyl}(4-chlorophenylmethanone

    Directory of Open Access Journals (Sweden)

    K. N. Venugopala

    2013-07-01

    Full Text Available The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent molecules with similar conformations. In the molecules, the thiazole ring is essentially planar [maximum atomic deviations = 0.014 (4 and 0.023 (5 Å] and is oriented with respect to the fluorophenyl ring and chlorophenyl rings at 9.96 (18 and 70.39 (18° in one molecule and at 7.50 (18 and 68.43 (18° in the other; the dihedral angles between the fluorophenyl and chlorophenyl rings are 64.9 (2 and 64.6 (2°, respectively. Intermolecular C—H...O and C—H...F hydrogen bonds stabilize the three-dimensional supramolecular architecture. Weak C—H...π and π–π interactions [centroid–centroid distance = 3.877 (3 Å] lead to a criss-cross molecular packing along the c axis.

  1. 3-(4-Hexyloxyphenyl-1,2,4-triazolo[3,4-b]benzothiazole

    Directory of Open Access Journals (Sweden)

    Dieter Schollmeyer

    2014-03-01

    Full Text Available The title compound, C20H21N3OS, was prepared by Huisgen reaction of 5-(4-hexyloxyphenyltetrazole and chlorobenzothiazole. The essentially planar benzothiazolotriazole framework [maximum deviation from the mean plane of 0.077 (1 Å for the bridgehead N atom] and the phenyl ring form a dihedral angle of 53.34 (5°. The hexyloxy chain adopts a gauche–all-anti conformation. The intracentroid separation of 3.7258 (8 Å between the triazole and benzene rings is the closest contact between individual molecules in the crystal.

  2. 76 FR 81496 - Product Cancellation Order for Certain Pesticide Registrations

    Science.gov (United States)

    2011-12-28

    ...- (Thiocyanomethylthi o)benzothiazole. 039967-00067 Preventol TC 60..... 2- (Thiocyanomethylthi o)benzothiazole. 039967-00072 TCMTB 30 G 2- (Thiocyanomethylthi o)benzothiazole. 039967-00078 TCMTB 30 WB......... 2- (Thiocyanomethylthi o)benzothiazole. 053883-00098 Prometon 25E........ Prometon. 053883-00099 Prometon...

  3. 76 FR 23588 - Notice of Receipt of Requests To Voluntarily Cancel Certain Pesticide Registrations

    Science.gov (United States)

    2011-04-27

    .......... Deltamethrin. 039967-00060 Tcmtb 80 2-(Thiocyanomethylthio)benzothiazole. 039967-00067 Preventol TC 60 2-(Thiocyanomethylthio)benzothiazole. 039967-00072 Tcmtb 30 G 2-(Thiocyanomethylthio)benzothiazole. 039967-00078 Tcmtb 30 WB 2-(Thiocyanomethylthio)benzothiazole. 051036-00421 Basagran AG...

  4. DNA interaction, antimicrobial studies of newly synthesized copper (II) complexes with 2-amino-6-(trifluoromethoxy)benzothiazole Schiff base ligands.

    Science.gov (United States)

    Rambabu, Aveli; Pradeep Kumar, Marri; Tejaswi, Somapangu; Vamsikrishna, Narendrula; Shivaraj

    2016-12-01

    Four novel Schiff base ligands, L(1) (1-((E)-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylimino)methyl)naphthalen-2-ol, C19H11F3N2O2S), L(2) (3-((E)-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylimino)methyl)benzene-1,2-diol, C15H9F3N2O3S), L(3) (2-((E)-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylimino)methyl)-5-methoxyphenol, C16H11F3N2O3S) and L(4) (2-((E)-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylimino)methyl)-4-bromophenol, C15H8BrF3N2O2S) and their binary copper(II) complexes 1 [Cu(L(1))2], 2 [Cu(L(2))2], 3 [Cu(L(3))2] and 4 [Cu(L(4))2] have been synthesized and characterized by elemental analysis, (1)H NMR, (13)C NMR, ESI mass, FT-IR, ESR, UV-Visible, magnetic susceptibility, TGA, SEM and powder XRD studies. Based on spectral and analytical data, a square planar geometry is assigned for all Cu(II) complexes. The ligands and their Cu(II) complexes have been screened for antimicrobial activity against bacterial species E. coli, P. aeruginosa, B. amyloliquefaciens and S. aureus and fungal species S. rolfsii and M. phaseolina and it is observed that all Cu(II) complexes are more potent than corresponding ligands. DNA binding (UV absorption, fluorescence and viscosity titrations) and cleavage (oxidative and photo cleavage) studies of Cu(II) complexes have also been investigated against calf thymus DNA (CT-DNA) and supercoiled pBR322 DNA respectively. From the experimental results, it is found that the complexes bound effectively to CT-DNA through an intercalative mode and also cleaved pBR322 DNA in an efficient manner. The DNA binding and cleavage affinities of newly synthesized Cu(II) complexes are in the order of 2>1>3>4.

  5. Chiral Separation of Novel a-Aminophosphonates Containing a Benzothiazole Moiety by Liquid Chromatography Using an Amylose Stationary Phase

    Institute of Scientific and Technical Information of China (English)

    LU Ping; ZHANG Yu-Ping; SONG Bao-An; YANG Song; BHADURY Shankar Pinaki; HU De-Yu; XUE Wei; CHEN Zhuo; JIN Lin-Hong

    2008-01-01

    The present report describes a chiral HPLC method for the enantiomeric separation of a-aminophosphonate derivatives using two new coated and immobilized amylose-based chiral stationary phases (CSP,Chiralpak IA and Chiralpak AD-H).The chromatographic parameters such as retention factor (k),separation factor (a),and resolution (Rs) of the solutes were investigated on these two CSPs.Reasonably good baseline separation for these compounds was achieved using Chiralpak IA column.The influences of temperature,content of ethanol modifier and the structure of analyte were also studied.THF,EtOAc and CH2Cl2 were used as ehients on analytical and semi-preparative columns.Highly enriched enantiomers with purities of up to 96.4%--100% (ee) and yields of 90.2%--95.5% were obtained,respectively.The proposed methods were found to be suitable and accurate for rapid separation and semi-preparation of enantiomeric a-aminophosphonate derivatives available.

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

    Science.gov (United States)

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

    2016-06-21

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

  7. A one-pot reaction to synthesize two types of fluorescent materials containing benzothiazolyl moiety.

    Science.gov (United States)

    Yu, Tianzhi; Zhang, Chengcheng; Zhao, Yuling; Chai, Haifang; Fan, Duowang; Ma, Ying; Yao, Shanglei; Li, Wentao

    2013-05-01

    Two different types of fluorescent materials containing benzothiazolyl moiety, 2-(benzothiazol-2-yl)phenol derivatives and 3-(benzothiazol-2-yl)coumarin derivatives, were synthesized synchronously using ethyl cyanoacetate, appropriate aromatic aldehyde and 2-aminothiophenol as the starting materials under the catalysis of benzoic acid by one-pot reaction. This method has the advantages of mild reaction conditions, easy processing and low waste. All synthesized compounds were characterized by elemental analysis, IR, (1)H NMR spectra. The structures of 2-(benzothiazol-2-yl)phenol derivatives, 2-(benzothiazol-2-yl)phenol (BTP) and 2-(benzothiazol-2-yl)naphthol (BTN), were determined by X-ray single crystal analysis. The UV-vis absorption and photoluminescence spectra of all synthesized compounds were investigated. The 2-(benzothiazol-2-yl)phenol derivatives exhibit bright green emissions and 3-(benzothiazol-2-yl)coumarin derivatives emit bright blue light in solutions.

  8. A Green Ultrasound Synthesis, Characterization and Antibacterial Evaluation of 1,4-Disubstituted 1,2,3-Triazoles Tethering Bioactive Benzothiazole Nucleus.

    Science.gov (United States)

    Rezki, Nadjet

    2016-04-18

    The synthesis of N-(benzo[d]thiazol-2-yl)-2-(4-substituted-1H-1,2,3-triazol-1-yl)acetamides 5a-r via the 1,3-dipolar cycloaddition reaction between 2-azido-N-(benzo[d]thiazol-2-yl)acetamide derivatives 3a-c and different alkynes were performed in the presence and absence of ultrasound irradiation. The synthesis was carried out using t-BuOH/H₂O (1:1, v/v) as reaction solvents and CuSO₄·5H₂O/sodium ascorbate as the catalyst. The copper catalyst was implemented to provide the regioselective 1,4-disubstituted 1,2,3-triazoles 5a-r. Significant reductions in reaction times with comparably higher yields were observed when the reactions were carried out under ultrasound irradiation. The structures of the newly synthesized 1,2,3-triazoles were elucidated by IR, NMR, MS, and elemental analyses. They were also screened for their antimicrobial activity against three gram-positive (Streptococcus pneumonia, Bacillus subtilis, and Staphylococcus aureus), three gram-negative (Pseudomonas aeuroginosa, Escherichia coli, and Klebsiella pneumonia), and two fungal strains (Aspergillus fumigates and Candida albicans). Most of the tested compounds displayed promising antimicrobial activities at a Minimum Inhibition Concentration (MIC) of 4-16 μg/mL.

  9. Biosynthesis of firefly luciferin in adult lantern: decarboxylation of L-cysteine is a key step for benzothiazole ring formation in firefly luciferin synthesis.

    Directory of Open Access Journals (Sweden)

    Yuichi Oba

    Full Text Available BACKGROUND: Bioluminescence in fireflies and click beetles is produced by a luciferase-luciferin reaction. The luminescence property and protein structure of firefly luciferase have been investigated, and its cDNA has been used for various assay systems. The chemical structure of firefly luciferin was identified as the D-form in 1963 and studies on the biosynthesis of firefly luciferin began early in the 1970's. Incorporation experiments using (14C-labeled compounds were performed, and cysteine and benzoquinone/hydroquinone were proposed to be biosynthetic component for firefly luciferin. However, there have been no clear conclusions regarding the biosynthetic components of firefly luciferin over 30 years. METHODOLOGY/PRINCIPAL FINDINGS: Incorporation studies were performed by injecting stable isotope-labeled compounds, including L-[U-(13C3]-cysteine, L-[1-(13C]-cysteine, L-[3-(13C]-cysteine, 1,4-[D6]-hydroquinone, and p-[2,3,5,6-D]-benzoquinone, into the adult lantern of the living Japanese firefly Luciola lateralis. After extracting firefly luciferin from the lantern, the incorporation of stable isotope-labeled compounds into firefly luciferin was identified by LC/ESI-TOF-MS. The positions of the stable isotope atoms in firefly luciferin were determined by the mass fragmentation of firefly luciferin. CONCLUSIONS: We demonstrated for the first time that D- and L-firefly luciferins are biosynthesized in the lantern of the adult firefly from two L-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of L-cysteine.

  10. Comparison of in vitro and ex vivo thyroid hormone synthesis inhibition results and in vivo outcomes for a series of benzothiazoles

    Science.gov (United States)

    Assessing how in vitro data may be used to predict adverse effects in vivo is critical as efforts are advanced to incorporate in vitro assays into a risk assessment framework. Within the context of a thyroid hormone (TH) synthesis inhibition adverse outcome pathway (AOP), in vitr...

  11. Synthesis of some new 4-oxo-thiazolidines, tetrazole and triazole derived from 2-SH-benzothiazole and antimicrobial screening of some synthesized

    Directory of Open Access Journals (Sweden)

    Suaad M.H. Al-Majidi

    2014-12-01

    Triazole moieties reported condensation (MBT with ethylbromo acetate and potassium hydroxide by the fusion method and resulted in ester-2-mercaptobenzothiazole (7, which was treated with hydrazine hydrate to give a hydrazine derivative (8, then converting these compounds (8 to phenyl semicarbazide (9 and phenyl thiosemicarbazide (10 derivatives. Cyclization compounds (9,10 in alkaline media (4 N·NaOH gave triazoles compounds (11,12. Furthermore the compound (8 was converted to the dithiocarbazate salt (13 which was then cyclized with hydrazine hydrate to give substituted triazole (14. The prepared compounds were identified by spectral methods (FTIR, 1H NMR, 13C NMR and some of its physical properties were measured and furthermore the effects of the preparing compounds on some strains of bacteria were studied.

  12. 2-[5-(4-Methoxyphenyl-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothiazole

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2011-09-01

    Full Text Available In the title compound, C24H21N3OS, the pyrazole ring makes dihedral angles of 5.40 (7 and 6.72 (8° with the benzo[d]thiazole ring system and the benzene ring, respectively, and a dihedral angle of 85.72 (8° with the methoxy-substituted benzene ring. In the crystal structure, the molecules are linked by C—H...π interactions.

  13. The use of new modified poly(acrylamide chelating resin with pendent benzothiazole groups containing donor atoms in the removal of heavy metal ions from aqueous solutions

    Directory of Open Access Journals (Sweden)

    Semmedu Selvaraj Kalaivani

    2014-03-01

    Full Text Available The adsorption studies of poly(6-(ethoxybenzothiazole acrylamide (PEBTA, for Cu(II and Zn(II metal ions removal from an aqueous solution have been investigated, as a function of solution pH, adsorbent dose, contact time, initial metal ion concentration and temperature. The chemical and structural characteristics of the adsorbent were determined by the FT-IR, 1H-NMR, TGA, SEM, and EDAX analysis. The maximum adsorption capacities of the adsorbent for Cu(II and Zn(II ions, as calculated from the Langmuir isotherm model, were 273.5 and 216.4 mg/g, respectively. The adsorption kinetic studies show that the adsorption of Cu(II and Zn(II ions onto PEBTA follows the pseudo second order kinetic model. Thermodynamic parameters such as ΔG°, ΔH° and ΔS° were also evaluated, and it has been found that the adsorption process is feasible, spontaneous and exothermic in nature. Desorption studies were carried out using 0.3 N HCl, and it revealed that the adsorbed Cu(II and Zn(II ions can be easily removed. The adsorption–desorption process is reversible, and this indicates that PEBTA is an effective adsorbent for the removal of heavy metal ions from an aqueous medium.

  14. Peripherally and non-peripherally tetra-benzothiazole substituted metal-free zinc (II) and lead (II) phthalocyanines: Synthesis, characterization, and investigation of photophysical and photochemical properties

    Science.gov (United States)

    Demirbaş, Ümit; Göl, Cem; Barut, Burak; Bayrak, Rıza; Durmuş, Mahmut; Kantekin, Halit; Değirmencioğlu, İsmail

    2017-02-01

    In this study, novel phthalonitrile compounds bearing 2-methylbenzo[d]thiazol-5-yloxy groups (4 and 5) and their peripherally and non-peripherally tetra-substituted metal-free (6 and 7), zinc (II) (8 and 9), and lead (II) (10 and 11) phthalocyanine derivatives were synthesized and characterized for the first time. These novel compounds showed extremely good solubility in most common organic solvents. The novel phthalocyanine compounds presented excellent results from photophysical and photochemical examinations in DMF solution. Especially, the singlet oxygen quantum yield (ΦΔ) values of the substituted zinc (II) phthalocyanines indicate that these compounds have significant potential as photosensitizers in cancer treatment by the photodynamic therapy (PDT) technique. The fluorescence quenching behaviour of these novel phthalocyanine compounds by 1,4-benzoquinone (BQ) was also examined in DMF solution.

  15. Nature of the lowest electron transitions in styryl bases benzothiazole derivatives and analogues bearing para-methoxy and -trifluoromethyl substituents in phenylyne moiety

    Science.gov (United States)

    Navozenko, O. M.; Naumenko, A. P.; Yashchuk, V. M.; Bricks, J. L.; Slominskii, Yu. L.; Ryabitskii, A. B.; Kachkovsky, O. D.

    2016-06-01

    Combined quantum-chemical and spectral investigation of cyanine bases derivatives of thiastyryls as well as their analogues with dimethylamino, metoxy and trifluorine-methyl substituents has been fulfilled. The calculations have shown that going from cationic styryl/metoxystyryl to the corresponding neutral bases is accompanied by substantial change of the equilibrium molecular geometry and charge distribution at atoms, while the experimental absorption band undergoes the essential hypsochromic shift. It is established that introducing on the donor groups in the bases causes negligible change of the carbon-carbon bond and atomic charges in the main chromophore, in contrast to the substantial changes of the magnitude and direction state dipole moments in both ground and excited states. It is found that the bases with the donor groups in benzthiazole moiety and with acceptor CF3 substituent demonstrate the inversion of the direction of the dipole moment. Based on the spectral and quantum-chemical study, one has proposed that some widening of the spectral bands is connected with the vibronic interaction, not with the second electron transition.

  16. Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII.

    Science.gov (United States)

    Ibrahim, Diaa A; Lasheen, Deena S; Zaky, Maysoun Y; Ibrahim, Amany W; Vullo, Daniela; Ceruso, Mariangela; Supuran, Claudiu T; Abou El Ella, Dalal A

    2015-08-01

    A series of novel 2-aminobenzothiazole derivatives bearing sulfonamide at position 6 was designed, synthesized and investigated as inhibitors of four isoforms of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), the cytosolic CA I and II, and the tumor-associated isozymes CA IX and XII. Docking and binding energy studies were carried out to reveal details regarding the favorable interactions between the scaffolds of these new inhibitors and the active sites of the investigated CA isoforms. Most of the novel compounds were acting as highly potent inhibitors of the tumor-associated hCA IX and hCA XII with KIs in the nanomolar range. The ubiquitous and dominant rapid cytosolic isozyme hCA II was also inhibited with KIs ranging from 3.5 to 45.4 nM. The favorable interactions between some of the new compounds and the active site of different CA isoforms were delineated by using molecular docking which may be useful for designing compounds with high affinity and selectivity for some CAs with biomedical applications.

  17. (Z)-3-Methyl-N-(7-nitroacridin-3-yl)-2,3-dihydro-1,3-benzothiazol-2-imine from laboratory powder diffraction data.

    Science.gov (United States)

    Vallcorba, Oriol; Latorre, Sonia; Alcobé, Xavier; Miravitlles, Carles; Rius, Jordi

    2011-11-01

    The title compound, C(21)H(14)N(4)O(2)S, belongs to a family of molecules possessing nonlinear optical properties in solution. Its structure has been solved from laboratory X-ray powder diffraction data using a new direct-space structure solution method, where the atomic coordinates are directly used as parameters and the molecular geometry is described by restraints. The molecular packing is controlled by two systems of π-π interactions and one weak edge-to-face interaction.

  18. Propan-2-yl 2-(1,1,3-trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-ylacetate

    Directory of Open Access Journals (Sweden)

    Muhammad Zia-ur-Rehman

    2012-09-01

    Full Text Available In the title molecule, C12H13NO5S, the benzisothiazole ring system is essentially planar (r.m.s. deviation = 0.0169 Å as is the –C—C(=O—O—C– sequence of atoms in the vicinity of the acetate group (r.m.s. deviation = 0.0044 Å. The mean plane of these atoms forms a dihedral angle of 88.41 (7° with the benzisothiazole ring system. In the crystal, weak C—H...O hydrogen bonds involving methylene and methyne H atoms form R43(20 graph-set motifs.

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

    Science.gov (United States)

    Parham, Hooshang; Khoshnam, Farzaneh

    2013-09-30

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

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

    Institute of Scientific and Technical Information of China (English)

    张英俊; 谭小华; 邵光; 彭志鸿; 安德烈

    2005-01-01

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

  1. {μ-2-[4-(1,3-Benzothiazol-2-ylphenyl]-2-azapropane-1,3-dithiolato-κ4S,S′:S,S′}bis[tricarbonyliron(I

    Directory of Open Access Journals (Sweden)

    Da-yong Jiang

    2012-03-01

    Full Text Available The title compound, [Fe2(C15H12N2S3(CO6], was prepared as an azadithiolatodiiron model for the active site of [FeFe]-hydrogenase. The Fe2S2 core adopts a butterfly shape, with each metal having a pseudo square-pyramidal geometry. The N-substituted azadithiolate is μ2-κ4S,S′:S,S′-coordinated to the Fe(CO3 moieties to form two fused six-membered rings with different conformations. The sum of the C—N—C angles around the N atom [356.85 (15°] indicates a flattening of the trigonal–pyramidal geometry about the N atom and an increase in the degree of sp2-hybridization.

  2. Benzothiazole Derivatives. 48. Synthesis of 3-Alkoxycarbonylmethyl-6-bromo-2-benzothiazolones and 3-Alkoxycarbonylmethyl-6-nitro-2-benzothiazolones as Potential Plant Growth Regulators

    Directory of Open Access Journals (Sweden)

    Viktor Sutoris

    1999-03-01

    Full Text Available 3-Alkoxycarbonylmethyl-6-bromo- and 3-alkoxycarbonylmethyl-6-nitro-2-benzothiazolones were synthesized by reaction of alkylesters of halogenoacetic acids with 6-bromo-2-benzothiazolones and 6-nitro-2-benzothiazolones respectively. The compounds were tested for plant growth stimulating activity on wheat (Triticum aestivum. The bromo derivatives manifested 25.4 % average stimulating activity in comparison with the control. The stimulation activity of the nitro derivatives was not significant. Optimal structures of the compounds were obtained by a MMPI method, atomic charges and dipole moments were calculated by a semiempirical AM1 method. On the basis of molecular electrostatic potential it has been found that the biological activity of synthesized compounds depends on charge distribution in the molecules.

  3. Nanocomposites Derived from Carbon Nanofibers and a Hyperbranched Poly(Ether-Ketone): In Situ Polymerization, Chain-End Modification, and Properties (Preprint)

    Science.gov (United States)

    2007-05-01

    benzothiazole , dodecyl ester and amine endgroups. For example, the dodecyl-terminated nanocomposite displayed an excellent solubility in chloroform and a much...converted to benzothiazole , dodecyl ester and amine endgroups. For example, the dodecyl-terminated nanocomposite displayed an excellent solubility in... Benzothiazole -terminated (HBP-PEK)-g-VGCNF (4): Into a 250 mL resin flask equipped with a high torque mechanical stirrer, and nitrogen inlet and outlet

  4. Cyanine dye–protein interactions: Looking for fluorescent probes for amyloid structures

    NARCIS (Netherlands)

    Volkova, K.D.; Kovalska, V.B.; Balanda, A.O.; Vermeij, R.J.; Subramaniam, V.; Slominskii, Yu.L.; Yarmoluk, S.M.

    2007-01-01

    We ascertained the ability to detect fibrillar β-lactoglobulin (BLG) of a series of mono-, tri-, penta-, and heptamethinecyanines based on benzothiazole and benzimidazole heterocycles, and of benzothiazole squaraine. Fluorescence properties of these cyanine dyes were measured in the unbound state an

  5. Polystyrene-supported Palladium(Ⅱ) Ethylenediamine Complex:A Recyclable Catalyst for the Syntheses of 2-Benzyl-imidazo[2,1-b][1,3]benzothiazoles by Sonogashira Reaction

    Institute of Scientific and Technical Information of China (English)

    BAKHERAD Mohammad; BAHRAMIAN Bahram; NASR-ISFAHANI Hossein; KEIVANLOO Ali; SANG Golnaz

    2009-01-01

    The polymer-supported palladium(Ⅱ) ethylenediamine complex was used as a catalyst for the heterocyclization during Sonogashira reaction between a substituted phenyl iodide and 2-amino-3-(2-propynyl)-1,3-benzothiazolium bromide, which could readily be recovered from the reaction medium by a simple filtration, and reused without a significant loss in its activity.

  6. Advanced Multi-Photon Chromophores for Broad-Band Ultra-Fast Optical Limiting

    Science.gov (United States)

    2014-11-04

    benzothiazole (BT) and NO2, represent a range of electron-donating (ED) and electron-withdrawing (EW) strengths, while the Pt-core acts as a weak ED...different substituents, R = N(phenyl)2 (NPh2), NH2, OCH3, t-butyl, CH3, H, F, CF3, CN, benzothiazole (BT) and NO2, represent a range of electron...variation in electron donating (ED) and electron withdrawing (EW) strengths R = NPh2, NH2, OCH3, t-Butyl, CH3, H, F, CF3, CN, Benzothiazole (BT) and

  7. Demand for Cyclohexylamine Increases Rapidly

    Institute of Scientific and Technical Information of China (English)

    Meng Hui

    2007-01-01

    @@ Cyclohexylamine is mainly used to synthesize sodium cyclamate and rubber accelerator CBS (N-cyclohexy-2-benzothiazole sulfenamide), The capacity of cyclohexylamine in China was 36 thousand t/a and the output was around 29 thousand tons in 2006.

  8. Synthesis and Microbial Studies of New Pyridine Derivatives-Ⅲ

    Institute of Scientific and Technical Information of China (English)

    PATEL,N.B.; AGRAVAT,S. N.

    2007-01-01

    2-Amino substituted benzothiazole 4a-41 and p-acetamidobenzenesulfonyl chloride 2 were used to prepare 2-(p-aminophenylsulfonamido) substituted benzothiazole 6a-61 using mixture of pyridine and acetic anhydride which formed an electrophilic complex (N-acetyl pyridinium) to facilitate condensation to give desired product by removal of HCl. 2-{p-[(3-Carboxypyrid-2-yl)amino]phenylsulfonamido}benzothiazoles 8a-81 were synthesized from 2-chloropyridine-3-carboxylic acid 7 and 6a-61 in 2-ethoxy ethanol using Cu-powder and K2CO3. Acid chlorides 9a-91 were condensed with 2-hydroxyethyl piperazine 10 and 2,3-dichloropiperazine 11 for amide derivatives 2-(p-((3-(4-(2-hydroxyethyl)piperazin-1-ylcarbonyl)pyrid-2-yl)amino)phenylsulfonamido)benzothiazoles 12a -121 and 2-{p-[3-(2,3-dichloropiperazin-1-ylcarbonyl)pyrid-2-ylamino]phenylsulfonamido}benzothiazoles 13a-131 respectively. The structures of the new compounds have been established on the basis of their chemical analysis and spectral data (IR, 1H NMR and mass). All the compounds have been screened for their antibacterial and antifungal activities.

  9. The underlying proantiarrhythmic mechanism of 5-HT_4 receptor agonist and 5-HT_3 receptor antagonist 2-[1-(4-piperonyl)piperazinyl]benzothiazole%5-HT_4受体激动剂兼5-HT_3 受体阻断剂2-[1-(4-piperonyl)piperazinyl]-benzothiazole致心律失常机制探析

    Institute of Scientific and Technical Information of China (English)

    刘清华; 张杨; 林媛媛; 吴博威

    2010-01-01

    目的 观察5-HT_4受体激动剂兼5-HT_3受体阻断剂2-[1-(4-piperonyl)piperazinyl]benzothiazole对大鼠离体心脏心律的影响,并探析其电生理学机制.方法 采用成年健康SD大鼠建立离体心脏Langendorff主动脉逆行灌流系统,观察0.1~10 μmol · L~(-1) 2-[1-(4-piperonyl)piperazinyl]benzothiazole对离体心脏节律的影响,全程记录心电图的变化.应用全细胞膜片钳技术观察2-[1-(4-piperonyl)piperazinyl]benzothiazole对胶原酶分解的大鼠心室肌细胞膜内向整流钾电流(I_(K1))、瞬时外向钾电流(I_(to))、静息膜电位(RMP)及动作电位(AP)的影响.结果 在大鼠离体心脏,0.1~10 μmol·L~(-1) 2-[1-(4-piperonyl)piperazinyl]benzothiazole可诱发明显的心律失常.给药15 min内,药物(10 μmol·L~(-1))诱发期前收缩(PVB)236±37个,室速(VT)和室颤(VF)发生率分别达到87.5%和62.5%(n=8,P<0.01).膜片钳记录结果显示,0.1~10 μmol·L~(-1) 2-[1-(4-piperonyl)piperazinyl]benzothiazole可浓度依赖性抑制大鼠心室肌IK1(EC50=0.74 μmol·L~(-1))和I_(to)(EC_(50)=2.16 μmol·L~(-1)),降低膜电位,并明显延长动作电位时程(n=6,P<0.01).结论 作为5-HT_4受体激动剂和5-HT_3受体阻断剂2-[1-(4-pipero-nyl)piperazinyl]benzothiazole致大鼠心律失常风险的电生理学机制为抑制I_(K1)和I_(to),降低膜电位,延长动作电位时程.

  10. Discovery and Pharmacokinetic and Pharmacological Properties of the Potent and Selective MET Kinase Inhibitor 1-{6-[6-(4-Fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]benzothiazol-2-yl}-3-(2-morpholin-4-ylethyl)urea (SAR125844).

    Science.gov (United States)

    Ugolini, Antonio; Kenigsberg, Mireille; Rak, Alexey; Vallée, Francois; Houtmann, Jacques; Lowinski, Maryse; Capdevila, Cécile; Khider, Jean; Albert, Eva; Martinet, Nathalie; Nemecek, Conception; Grapinet, Sandrine; Bacqué, Eric; Roesner, Manfred; Delaisi, Christine; Calvet, Loreley; Bonche, Fabrice; Semiond, Dorothée; Egile, Coumaran; Goulaouic, Hélène; Schio, Laurent

    2016-08-11

    The HGF/MET pathway is frequently activated in a variety of cancer types. Several selective small molecule inhibitors of the MET kinase are currently in clinical evaluation, in particular for NSCLC, liver, and gastric cancer patients. We report herein the discovery of a series of triazolopyridazines that are selective inhibitors of wild-type (WT) MET kinase and several clinically relevant mutants. We provide insight into their mode of binding and report unprecedented crystal structures of the Y1230H variant. A multiparametric chemical optimization approach allowed the identification of compound 12 (SAR125844) as a development candidate. In this chemical series, absence of CYP3A4 inhibition was obtained at the expense of satisfactory oral absorption. Compound 12, a promising parenteral agent for the treatment of MET-dependent cancers, promoted sustained target engagement at tolerated doses in a human xenograft tumor model. Preclinical pharmacokinetics conducted in several species were predictive for the observed pharmacokinetic behavior of 12 in cancer patients.

  11. Dimethyl [(4-fluorophenyl(6-methoxybenzothiazol-2-ylaminomethyl]phosphonate

    Directory of Open Access Journals (Sweden)

    Yan-Ping Hong

    2009-06-01

    Full Text Available In the molecule of title compound, C17H18FN2O4PS, both the benzene ring with its conjunction C atom and the benzothiazole ring with its conjunction N atom are close to planar (the maximum deviations are 0.0267 and 0.0427 Å for the benzene and benzothiazole rings, respectively, the dihedral angle between the planes of the benzothiazole and benzene rings is 119.05 (3°. The molecular packing is stabilized by intermolecular N—H...O, C—H...N and C—H...F hydrogen bonding, and by C—H...π and π–π stacking interactions [centroid–centroid distances = 2.99 (2, 2.96 (3, 2.88 (2 and 3.773 (4 Å].

  12. Single & Two-photon Excited Fluorescence of Two New Compounds with 2-Benzothiazolyl as Electron Acceptor

    Institute of Scientific and Technical Information of China (English)

    2003-01-01

    Two new D-π-A type compounds, where electron-donor D is tertiary amino group, electron-acceptor A is 2-benzothiazolyl and π is two conjugated styryl units, have been synthesized.They are named as trans, trans-2-{4-[4-(N, N-diethylamino)styryl]styryl}-1, 3-benzothiazole and trans, trans-2-{4-[4-(N, N-diphenylamino)styryl]styryl}-1, 3-benzothiazole.Both compounds show strong two-photon excited fluorescence in yellow-orange region when excited by a femtosecond laser at 800 nm.

  13. Synthesis of Novel Heterocyclic 4-Thiazolidinone Derivatives and their Antibacterial Activity

    Directory of Open Access Journals (Sweden)

    K. M. Mistry

    2004-01-01

    Full Text Available 4-Thiazolidinones have been prepared by the reaction of various substituted Schiff bases 3 with Thioglycolic acid and Thiolactic acid. The intermediate Schiff bases 3 were synthesized by the condensation of various substituted 2-amino benzothiazole 1 with 1-(4'-methyl Phenyl-3-methyl-5-pyrazolone 2. The starting compound substituted 2-amino benzothiazoles were prepared from various substituted amines via substituted phenyl thiourea. The structures of the compounds have been confirmed by elemental analysis and spectral analysis. The antibacterial activity of the compounds has also been screened against Staphylococcus aureus and Escherichia coli.

  14. Utility of 4-formylantipyrine in heterocyclic synthesis

    Directory of Open Access Journals (Sweden)

    Abdou O. Abdelhamid

    2010-04-01

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

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

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

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

  16. Design, Synthesis and Anti-HIV Integrase Evaluation of 4-Oxo-4H-quinolizine-3-carboxylic Acid Derivatives

    Directory of Open Access Journals (Sweden)

    Li-Ming Hu

    2009-02-01

    Full Text Available 4-Oxo-4H-quinolizine-3-carboxylic acid derivatives bearing sulfamido, carboxylamido, benzimidazole and benzothiazole substituents have been designed and synthesized. The structures of these new compounds were confirmed by 1H-NMR, 13C- NMR, IR and ESI (or HRMS spectra. Compounds were screened for possible HIV integrase inhibitory activity.

  17. Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil

    NARCIS (Netherlands)

    Li, Zhipeng; Li, Xiufeng; Zhang, Yawen; Ren, T.; Zhao, Yidong; Zeng, X.; Heide, van der E.

    2014-01-01

    A novel long chain alkyl phenylboronic acid ester containing heterocyclic compound, bis (1-(benzothiazol-2-ylthio) propan-2-yl)-4-dodecylphenylboronic acid ester (DBBMT), was synthesized and characterized. The hydrolytic stability of the DBBMT was evaluated and the results show that DBBMT is of outs

  18. Manufacturing Methods and Technology Project Summary Reports

    Science.gov (United States)

    1984-06-01

    methyl pyrrolidinone, benezaldehyde, nitroguanyl hydrazone, melamine , formaldehyde , and methyl cellulose. None appeared to be adequately effective...and other by-products. However, addi- tional analysis using gas chromatography/mass spectrometry identified other compounds such as dimethyl- sulfone ...additional analysis, as stated earlier, led to the detection of three additional compounds: dimethyl sulfone , benzothiazole and diacetone alcohol. Both

  19. Specific fluorescent detection of fibrillar α-synuclein using mono- and trimethine cyanine dyes

    NARCIS (Netherlands)

    Volkova, K.D.; Kovalska, V.B.; Balanda, A.O.; Losytskyy, M.Yu; Golub, A.G.; Vermeij, R.J.; Subramaniam, V.; Tolmachev, O.I.; Yarmoluk, S.M.

    2008-01-01

    With the aim of searching of novel amyloid-specific fluorescent probes the ability of series of mono- and trimethine cyanines based on benzothiazole, pyridine and quinoline heterocycle end groups to recognize fibrillar formations of α-synuclein (ASN) was studied. For the first time it was revealed t

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

    OpenAIRE

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

    2002-01-01

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

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

    Directory of Open Access Journals (Sweden)

    P. Almeida

    2002-03-01

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

  2. Fluorescent compounds for plastic scintillation applications

    Energy Technology Data Exchange (ETDEWEB)

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

    1994-04-01

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

  3. N-Acetonylsaccharin

    Directory of Open Access Journals (Sweden)

    Matloob Ahmad

    2009-09-01

    Full Text Available In the title compound [systematic name: 2-(2-oxopropyl-1,2-benzothiazol-3(2H-one 1,1-dioxide], C10H9NO4S, the benzothiazole unit is essentially planar [maximum deviation = 0.0490 (9 Å for the S atom] and the oxopropyl group is inclined at an angle 75.61 (8° with respect to its mean plane. In the crystal, molecules are held together by weak intermolecular C—H...O non-classical hydrogen bonds, resulting in centrosymmetric dimeric units, forming 14-membered ring systems which may be described as R22(14 ring motifs. Moreover, molecules lying about inversion centers show π–π interactions, with centroid–centroid separations between the benzene rings of 3.676 (2 Å.

  4. The interplay of skeletal deformations and ultrafast excited-state intramolecular proton transfer: Experimental and theoretical investigation of 10-hydroxybenzo[h]quinoline

    Energy Technology Data Exchange (ETDEWEB)

    Schriever, Christian [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany)], E-mail: christian.schriever@physik.uni-muenchen.de; Barbatti, Mario [Institute for Theoretical Chemistry - University of Vienna, Waehringer Strasse 17, 1090 Vienna (Austria)], E-mail: mario.barbatti@univie.ac.at; Stock, Kai [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany); Aquino, Adelia J.A.; Tunega, Daniel [Institute for Theoretical Chemistry - University of Vienna, Waehringer Strasse 17, 1090 Vienna (Austria); Lochbrunner, Stefan [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany); Riedle, Eberhard [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany)], E-mail: eberhard.riedle@physik.uni-muenchen.de; Vivie-Riedle, Regina de [Department Chemie - Ludwig-Maximilians-Universitaet (LMU), Butenandt-Strasse 11, 81377 Muenchen (Germany)], E-mail: regina.de_vivie@cup.uni-muenchen.de; Lischka, Hans [Institute for Theoretical Chemistry - University of Vienna, Waehringer Strasse 17, 1090 Vienna (Austria)], E-mail: hans.lischka@univie.ac.at

    2008-05-23

    The excited-state intramolecular proton transfer in the aromatic polycycle 10-hydroxybenzo[h]quinoline is investigated by means of transient absorption experiments with 30 fs time resolution, classical dynamics and wavepacket dynamics. The experiments establish the ultrafast transfer after UV excitation and show signatures of coherent vibrational motion in the keto product. To elucidate details of the proton transfer mechanism, the classical dynamics is also performed for 2-(2'-hydroxyphenyl)benzothiazole and the results are compared. For both systems the proton transfer takes place on the ultrafast scale of 30-40 fs, with good agreement between the theoretical investigations and the measurements. The dynamics simulations show that for both molecules the proton is handed over by means of skeletal deformation of the molecule. Due to the more rigid structure of 10-hydroxybenzo[h]quinoline the hydrogen migration mode participates more actively than in 2-(2'-hydroxyphenyl)benzothiazole.

  5. Preparation and fluorescent properties of a complex probe based on inorganic QDs and organic dye

    Energy Technology Data Exchange (ETDEWEB)

    Fei Xuening, E-mail: xueningfei@126.co [Department of Material Science and Engineering, TianJin Institute of Urban Construction, No. 26, Jinjing Road, Tianjin 300384 (China) and School of Chemical Engineering and Technology, TianJin University, Tianjin 300072 (China); Gu Yingchun [School of Chemical Engineering and Technology, TianJin University, Tianjin 300072 (China); Department of Material Science and Engineering, TianJin Institute of Urban Construction, No. 26, Jinjing Road, Tianjin 300384 (China); Wang Jun; Jia Guozhi; Liu Zhijun [Department of Material Science and Engineering, TianJin Institute of Urban Construction, No. 26, Jinjing Road, Tianjin 300384 (China)

    2011-02-15

    A novel complex fluorescent probe based on quantum dots and organic dye (QDs-TO) was designed and prepared by incorporating a benzothiazole derivative into QDs-1-(3-amidepropyl)-4-methylquinoline. The complex probe was characterized by FT-IR and TG/DTA. The emission wavelength of QDs-1-(3-amidepropyl)-4-methylquinoline was found at 475 nm and a new peak corresponding to QDs-TO appeared at 550 nm, indicating that benzothiazole derivative can react with QDs-1-(3-amidepropyl)-4-methylquinoline to afford QDs-TO. Furthermore, the emission wavelength of QDs shifted blue while the characteristic peak of TO shifted red during the reaction. This suggests that the probe may be useful for biological labeling in offering an efficient method to study the interrelation between quantum dots and organic dyes.

  6. (E-4-(Benzo[d]thiazol-2-yl-N-(pyridin-3-ylmethylideneaniline hemihydrate

    Directory of Open Access Journals (Sweden)

    Li Hong

    2016-10-01

    Full Text Available The title compound, C19H13N3S·0.5H2O, is a benzothiazole derivative that crystallized as a hemihydrate, the water O atom being situated on a twofold rotation axis. The dihedral angles between the central benzene ring and the benzothiazole (r.m.s. deviation = 0.012 Å and pyridine rings are 3.57 (6 and 10.12 (8°, respectively, indicating that the molecule is nearly planar. The conformation about the N=C bond is E. In the crystal, molecules are linked by Owater—H...Npyridine hydrogen bonds, forming dimers, which in turn are linked by C—H...O hydrogen bonds into layers parallel to the ab plane. The layers are linked by offset π–π interactions, forming a three-dimensional network [shortest intercentroid distance = 3.721 (2 Å].

  7. 2-Arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria.

    Science.gov (United States)

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

    2011-05-01

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

  8. One-pot non-enzymatic formation of firefly luciferin in a neutral buffer from p-benzoquinone and cysteine.

    Science.gov (United States)

    Kanie, Shusei; Nishikawa, Toshio; Ojika, Makoto; Oba, Yuichi

    2016-04-21

    Firefly luciferin, the substrate for the bioluminescence reaction of luminous beetles, possesses a benzothiazole ring, which is rare in nature. Here, we demonstrate a novel one-pot reaction to give firefly luciferin in a neutral buffer from p-benzoquinone and cysteine without any synthetic reagents or enzymes. The formation of firefly luciferin was low in yield in various neutral buffers, whereas it was inhibited or completely prevented in acidic or basic buffers, in organic solvents, or under a nitrogen atmosphere. Labelling analysis of the firefly luciferin using stable isotopic cysteines showed that the benzothiazole ring was formed via the decarboxylation and carbon-sulfur bond rearrangement of cysteine. These findings imply that the biosynthesis of firefly luciferin can be developed/evolved from the non-enzymatic production of firefly luciferin using common primary biosynthetic units, p-benzoquinone and cysteine.

  9. 2-[2-(3-Chlorophenyl-2-oxoethyl]-1,2-benzisothiazol-3(2H-one 1,1-dioxide

    Directory of Open Access Journals (Sweden)

    Masood Parvez

    2010-03-01

    Full Text Available In the title compound, C15H10ClNO4S, the benzothiazole ring system is essentially planar [maximum deviation = 0.0382 (13 Å for the N atom] and forms a dihedral angle of 74.43 (6° with the chloro-substituted benzene ring. In the crystal structure, weak intermolecular C—H...O hydrogen bonds form R22(10 and R22(16 ring motifs

  10. Antimicrobial evaluation of diaminothiazoloylbenzothiazoles

    Directory of Open Access Journals (Sweden)

    A. Yardily

    2016-05-01

    Full Text Available A series of 2-(4-amino-2-aryl/alkylaminothiazol-5-oyl benzothiazole derivatives were synthesized from amidinothioureas and 2-(2-bromoacetylbenzothiazole with triethylamine. Their structures were established on the basis of IR, 1H NMR, 13C NMR and mass spectral analyses. All the synthesized compounds were screened for their antibacterial, antifungal and antimycobacterial potential. All the compounds showed significant activity against the microorganisms tested.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2007-12-15

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

  12. 2-Amino-6-methyl-1,3-benzothiazole–octanedioic acid (2/1

    Directory of Open Access Journals (Sweden)

    Yao-Geng Wang

    2009-11-01

    Full Text Available Cocrystallization of 2-amino-6-methy-1,3-benzothiazole with octanedioic acid in a mixed methanol–water medium afforded the title 2:1 cocrystal, 2C8H8N2S·C8H14O4. The octanedioic acid molecule is located on an inversion centre. In the crystal, intermolecular N—H...O and O—H...O hydrogen bonds connect the components into a three-dimensional network.

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

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

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

  14. Rearrangement of 2—Benzothiazolylthioacetyl hidrazide in Ethanol Solution of Potassium Hydroxide:Synthesis of s—Triazolo[3,4—b] benzothiazol—3—thiol and Its Derivatives

    Institute of Scientific and Technical Information of China (English)

    ZHANG,Yan; HUI,Xin-Ping; 等

    2002-01-01

    A novel rearrangement reaction about 2-benzothiazolylthioacetyl hydrazide (1) to produce s-triazolo[3,4-b] benzothiazol-3-thiol (3) in the presence of KOH and CS2 was described.Other way to synthesize 3 from 2-benzothiazolyl-hydrazine (2) under the same condition was compared and the Mannich reaction of compound 3 was reported too.Their structures were established by elemental analyses,IR,1H nmr and MS spectra.

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

    Institute of Scientific and Technical Information of China (English)

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

    2009-01-01

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

  16. Theoretical insight into the excited-state intramolecular proton transfer mechanisms of three amino-type hydrogen-bonding molecules

    Science.gov (United States)

    An, Beibei; Yuan, Huijuan; Zhu, Qiuling; Li, Yuanyuan; Guo, Xugeng; Zhang, Jinglai

    2017-03-01

    Excited-state intramolecular proton transfer (ESIPT) dynamics of the amino-type hydrogen-bonding compound 2-(2‧-aminophenyl)benzothiazole (PBT-NH2) as well as its two derivatives 2-(5‧-cyano-2‧-aminophenyl)benzothiazole (CN-PBT-NH2) and 2-(5‧-cyano-2‧-tosylaminophenyl)benzothiazole (CN-PBT-NHTs) were studied by the time-dependent density functional theory (TD-DFT) approach with the B3LYP density functional, and their absorption and emission spectra were also explored at the same level of theory. A good agreement is observed between the theoretical simulations and experimental spectra, indicating that the present calculations are reasonably reliable. In addition, it is also found that the energy barriers of the first excited singlet state of the three targeted molecules along the ESIPT reaction are computed to be 0.38, 0.34 and 0.12 eV, respectively, showing the trend of gradual decrease, which implies that the introduction of the electron-withdrawing cyano or tosyl group can facilitate the occurrence of the ESIPT reaction of these amino-type H-bonding systems. Following the ESIPT, both CN-PBT-NH2 and CN-PBT-NHTs dye molecules can undergo the cis-trans isomerization reactions in the ground-state and excited-state potential energy curves along the C2-C3 bond between benzothiazole and phenyl moieties, where the energy barriers of the trans-tautomer → cis-tautomer isomerizations in the ground states are calculated to be 0.83 and 0.34 eV, respectively. According to our calculations, it is plausible that there may exist the long-lived trans-tautomer species in the ground states of CN-PBT-NH2 and CN-PBT-NHTs.

  17. What Is Its Real Existing Form? ---Theoretical and Experimental Studies on 2-Mercaptobenzothiazole

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    The geometry of 2-mercaptobenzothiazole (MBT) and its tautomeric form of benzo- thiazole-2-thione are optimized at B3LYP/6-311G** and HF/6-311G** levels, respectively. The crystal structure of benzothiazole-2-thione and its FTIR spectra are also obtained. From the calcu- lated and experimental data, it can be concluded that in gas-phase and solid-state, the real existing form of 2-mercaptobenzothiazole is the thione-form of MBT.

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

    OpenAIRE

    Eduardo Soriano; Cory Holder; Andrew Levitz; Maged Henary

    2015-01-01

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

  19. Antimicrobial Evaluation and Synthesis of Some Phenylpyrazolo benzothiazolo quinoxaline Derivatives

    OpenAIRE

    2009-01-01

    2,3-Diphenyl quinoxaline (SI) was fused with 2-amino benzothiazoles (SII) by a methylene bridge, which was then allowed for acetylation. The acetylated product (SIV) was made to react with different aromatic aldehydes to give chalcones (SV1-SV5). Chalcones refluxed with substituted acid hydrazides to afford different phenyl pyrazolo benzothiazolo quinoxaline derivatives (SVI1-SVI15). The structure of chalcones and phenyl pyrazolo benzothiazolo quinoxaline derivatives were confirmed by M.P, TL...

  20. A Multidisciplinary Investigation to Determine the Structure and Source of Dimeric Impurities in AMG 517 Drug Substance

    Directory of Open Access Journals (Sweden)

    Maria Victoria Silva Elipe

    2009-01-01

    Full Text Available In the initial scale-up batches of the experimental drug substance AMG 517, a pair of unexpected impurities was observed by HPLC. Analysis of data from initial LC-MS experiments indicated the presence of two dimer-like molecules. One impurity had an additional sulfur atom incorporated into its structure relative to the other impurity. Isolation of the impurities was performed, and further structural elucidation experiments were conducted with high-resolution LC-MS and 2D NMR. The dimeric structures were confirmed, with one of the impurities having an unexpected C-S-C linkage. Based on the synthetic route of AMG 517, it was unlikely that these impurities were generated during the last two steps of the process. Stress studies on the enriched impurities were carried out to further confirm the existence of the C-S-C linkage in the benzothiazole portion of AMG 517. Further investigation revealed that these two dimeric impurities originated from existing impurities in the AMG 517 starting material, N-acetyl benzothiazole. The characterization of these two dimeric impurities allowed for better quality control of new batches of the N-acetyl benzothiazole starting material. As a result, subsequent batches of AMG 517 contained no reportable levels of these two impurities

  1. Adsorption of N/S heterocycles in the flexible metal-organic framework MIL-53(Fe(III)) studied by in situ energy dispersive X-ray diffraction.

    Science.gov (United States)

    Van de Voorde, Ben; Munn, Alexis S; Guillou, Nathalie; Millange, Franck; De Vos, Dirk E; Walton, Richard I

    2013-06-14

    The adsorption of N/S-containing heterocyclic organic molecules in the flexible iron(III) terephthalate MIL-53, Fe(III)(OH)(0.6)F(0.4)(O2C-C6H4-CO2)·(H2O), from the liquid phase was studied with in situ energy dispersive X-ray diffraction (EDXRD), in order to follow the adsorption-induced expansion of the structure. For comparison with the diffraction data, liquid phase adsorption isotherms were recorded for uptake of benzothiophene, benzothiazole and indole in isopropanol and in heptane. The solvent not only influences pore opening but is also a competing guest. The in situ EDXRD experiments allow the kinetics of guest uptake and the competition with solvent to be monitored directly. Indole uptake is limited; this adsorbate is barely capable of opening the closed, either hydrated or dehydrated, MIL-53(Fe) structure, or of penetrating the isopropanol-containing material in the concentration range under study. When isopropanol is used as a solvent, the guest molecules benzothiophene and benzothiazole must be present at a certain threshold concentration before substantial adsorption into the metal-organic framework takes place, eventually resulting in full opening of the structure. The fully expanded structures of benzothiophene or benzothiazole loaded MIL-53(Fe) materials have Imcm symmetry and a unit cell volume of ca. 1600 Å(3), and upon uptake of the guest molecules by the closed form (unit cell volume ~1000 Å(3)) no intermediate crystalline phases are seen. Successful uptake by MIL-53(Fe) requires that the adsorbate is primarily a good hydrogen bond acceptor; additionally, based on UV-visible spectroscopy, a charge-transfer interaction between the S atoms of benzothiophene and the aromatic rings in the MOF pore wall is proposed.

  2. Structures of hydrazones, (E)-2-(1,3-benzothiazolyl)-NHsbnd Ndbnd CHsbnd Ar, [Ar = 4-(pyridin-2-yl)phenyl, pyrrol-2-yl, thien-2-yl and furan-2-yl]: Difference in conformations and intermolecular hydrogen bonding

    Science.gov (United States)

    Lindgren, Eric B.; Yoneda, Julliane D.; Leal, Katia Z.; Nogueira, Antônio F.; Vasconcelos, Thatyana R. A.; Wardell, James L.; Wardell, Solange M. S. V.

    2013-03-01

    Structures of hydrazones, (E)-2-(1,3-benzothiazolyl)-NHsbnd Ndbnd CHsbnd Ar(Ar = pyridine-2-yl (1), pyrrol-2-yl (2), thien-2-yl (3) and furan-2-yl (4), prepared from 2-hydrazinyl-1,3-benzothiazole and ArCHO, followed by recrystallisation from alcohol solutions, are reported. No significant intramolecular hydrogen bonds are present in any of the four molecules. Different conformations were found between 2 and 3, on one hand and for 4, on the other. Thus for 4, the oxygen atom of the furanyl ring is on the same side of the molecule as is the sulfur atom of the benzothiazole unit, while in contrast, each of the heteroatoms of the thienyl and pyrrole rings lies on opposite sides to the benzothiazole sulphur atom. In addition to the conformational variations, differences are noted in the connections between molecules. Despite the presence in each case of N(hydrazono)sbnd H---N(benzothiazolo) intermolecular hydrogen bonds, molecules of 4 are linked into spiral chains, while molecules of 2 and 3 (and indeed all compounds having Ar = substituted phenyl) form symmetric dimers. Further intermolecular interactions, albeit weaker ones, are found in 2 [Csbnd H··N and Nsbnd H··π], 3 [Csbnd H··π] and 4 [π··π], while dimers of 1 remain essentially free. Calculations carried out using the DFT(B3LYP)/6-311++G(d,p) method indicated that the conformations determined by crystallography for 2-4 were the more stable.

  3. Thin Film Electrodeposition of Ir(III Cyclometallated Complexes

    Directory of Open Access Journals (Sweden)

    Andreea Ionescu

    2016-01-01

    Full Text Available Novel electropolymerizable Ir(III cyclometallated complexes have been synthesized and characterized. In these complexes the cyclometallated ligands are either 2-phenylpyridine H(PhPy or benzothiazole-triphenylamine H(BzTh-tpa, while the Ir(III coordination sphere is completed by a Schiff base substituted with a triphenylamine fragment. A complete electrochemical study has been conducted on all complexes, in order to verify the feasibility of electropolymerization and to elucidate the role of the specific position of the triphenylamine moiety in the molecular structure. Homogeneous thin films of Ir(III metallopolymers have been successfully obtained through electropolymerization process.

  4. Synthesis and Anti-TMV Activity of Dialkyl/dibenzyl 2-((6-Substituted-benzo[d]thiazol-2-ylamino(benzofuran-2-ylmethyl Malonates

    Directory of Open Access Journals (Sweden)

    Meichuan Li

    2013-11-01

    Full Text Available Starting from benzofuran-2-methanal, 6-substituted benzothiazole-2-amines and malonic esters, sixteen title compounds were designed and synthesized seeking to introduce anti-TMV activity. The structures of the newly synthesized compounds were confirmed by 1H-NMR, 13C-NMR, IR spectra, and MS (HREI analysis. The bioassays identified some of these new compounds as having moderate to good anti-TMV activity. The compounds 5i and 5m have good antiviral activity against TMV with a curative rate of 52.23% and 54.41%, respectively, at a concentration of 0.5 mg/mL.

  5. (E-2-[(6-Ethoxybenzothiazol-2-yliminomethyl]-6-methoxyphenol

    Directory of Open Access Journals (Sweden)

    Ling-Qian Kong

    2009-04-01

    Full Text Available In the title molecule, C17H16N2O3S, the benzothiazole fragment and the benzene ring form a dihedral angle of 13.8 (4°, and an intramolecular O—H...N hydrogen bond occurs. In the crystal structure, pairs of weak intermolecular O—H...S and C—H...(O,O hydrogen bonds link molecules into centrosymmetric dimers. These dimers are related by translation along the a axis and form stacks via π–π interactions, with a short intermolecular distance of 3.766 (5 Å between the centroids of the benzene and thiazole rings.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2014-10-06

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

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

    Directory of Open Access Journals (Sweden)

    Hamdi Ali Elagab

    2016-03-01

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

  8. Bench-Scale Synthetic Optimization of 1,2-bis(2-aminophenylthio)ethane (APO-Link) Used in the Production of APO-BMI Resin

    Energy Technology Data Exchange (ETDEWEB)

    Hilary Wheeler; Crystal Densmore

    2007-07-31

    The diamine reagent 1,2-bis(2-aminophenylthio)ethane is no longer commercially available but still required for the synthesis of the bismaleimide resin, APO-BMI, used in syntactic foams. In this work, we examined the hydrolysis of benzothiazole followed the by reaction with dichloroethane or dibromoethane. We also studied the deprotonation of 2-aminothiophenol followed by the reaction with dibromoethane. We optimized the latter for scale-up by scrutinizing all aspects of the reaction conditions, work-up and recrystallization. On bench-scale, our optimized procedure consistently produced a 75-80% overall yield of finely divided, high purity product (>95%).

  9. Structure-spectroscopic property relationships in a series of platinum acetylides

    Science.gov (United States)

    Cooper, Thomas M.; Haley, Joy E.; Krein, Douglas M.; Burke, Aaron R.; Slagle, Jonathan E.

    2016-09-01

    In order to understand electronic and conformational effects on structure-spectroscopic property relationships in platinum acetylides, we synthesized a model series of chromophores trans-Pt(PBu3)2(C-CPhenyl-X)2, where X = NH2, OCH3, diphenylamino, t-Bu, methyl, H, F, benzothiazole, trifluoromethyl, CN and nitro. We collected linear spectra, including ground state absorption, phosphorescence and phosphorescence excitation spectra. We also performed DFT and TDDFT calculations on the ground and excited state properties of these compounds. The calculations and experimental data show the excited state properties are a function of the electronic properties of the substituents and the molecular conformation.

  10. Synthesis and Analytical Application of Bis(2-diazoaminobenzothiazoyl)-benzidine to Determination of Mercury Ion by Fluorimetry

    Institute of Scientific and Technical Information of China (English)

    JIANG Run-sheng; FENG Feng; CHEN Ze-zhong; BAI Yun-feng; LIN Sen; FU Guo-liang

    2009-01-01

    A new fluorescent reagent bis(2-diazoaminobenzothiazoyl)-benzidine(BDABTB) was synthesized by combining benzothiazole with benzidine and triazene reagent. The product was confirmed by elemental analysis, 1HNMR and FTIR. The excitation and emission wavelengths of BDABTB were 214 and 338 nm in a basic medium, respectively. The fluorescence was quenched by Hg~(2+) selectively and sensitively. The linear range of Hg~(2+) was 1.0×10~(-8)-1.0×10~(-5) mol/L with a detection limit of 5.0×10~(-10) mol/L. It has been used to determine trace Hg~(2+) in water sample with satisfactory results.

  11. 发光材料、荧光材料

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    O482.31 2000064215苯并噻唑衍生物用作EL器件中发光材料的研究=Study of benzothiazolate derivative as novelemitting materials in blue organic electroluminescentdevices[刊,中]/张晓宏,吴世康(中科院感光化学所.北京(100101)),李振声,邝海伦,李述汤(香港城市大学物理与材料系.香港)//感光科学与光化学.—1999,17(3).—199-202

  12. 2-[2-(3-Methoxyphenyl-2-oxoethyl]-1,2-benzisothiazol-3(2H-one 1,1-dioxide

    Directory of Open Access Journals (Sweden)

    Masood Parvez

    2010-03-01

    Full Text Available In the title compound, C16H13NO5S, the benzothiazole unit is essentially planar [maximum deviation = 0.0501 (10 Å for the S atom] and is oriented at a dihedral angle of 67.85 (5° with respect to the methoxy-substituted benzene ring. The mean plane of the methoxy group is oriented at 14.3 (3° with respect to the benzene ring to which it is attached. In the crystal structure, weak C—H...O hydrogen bonds form macrocyclic rings with R22(10 and R22(12 motifs.

  13. Antimicrobial Evaluation and Synthesis of Some Phenylpyrazolo benzothiazolo quinoxaline Derivatives

    Directory of Open Access Journals (Sweden)

    CH. Sridevi

    2009-01-01

    Full Text Available 2,3-Diphenyl quinoxaline (SI was fused with 2-amino benzothiazoles (SII by a methylene bridge, which was then allowed for acetylation. The acetylated product (SIV was made to react with different aromatic aldehydes to give chalcones (SV1-SV5. Chalcones refluxed with substituted acid hydrazides to afford different phenyl pyrazolo benzothiazolo quinoxaline derivatives (SVI1-SVI15. The structure of chalcones and phenyl pyrazolo benzothiazolo quinoxaline derivatives were confirmed by M.P, TLC and spectral data. All the synthesized compounds were screened for their antimicrobial activities.

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

    Science.gov (United States)

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

    2016-08-10

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

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

    Science.gov (United States)

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

    2011-05-15

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

  16. Synthesis and antiulcer activity studies of 2-(1′-iminothioimido substituted-1′-substituted phenylbenzoic acids

    Directory of Open Access Journals (Sweden)

    Subudhi B

    2008-01-01

    Full Text Available Certain 2-(1′-iminothioimido substituted-1′-substituted phenybenzoic acids (P 1-9 were synthesized by reaction of phthalic anhydride with benzotriazole, 2-mercapto benzothiazole and 2-p-amino phenyl benzimidazole, respectively (A 1-3 followed by imine formation with Schiff bases of thiourea with salicylaldehyde, furfuraldehyde and 1-phenyl-3-methyl-5-pyrazolone. Antiulcer activity was evaluated using reduction in total acidity, free acidity and ulcer index as parameters. Compounds P 3 , P 6 , P 7 and P 9 (100 mg/kg showed significant (P< 0.001 antiulcer action compared to control and omeprazole (40 mg/kg.

  17. Plant-plant-microbe mechanisms involved in soil-borne disease suppression on a maize and pepper intercropping system.

    Directory of Open Access Journals (Sweden)

    Min Yang

    Full Text Available BACKGROUND: Intercropping systems could increase crop diversity and avoid vulnerability to biotic stresses. Most studies have shown that intercropping can provide relief to crops against wind-dispersed pathogens. However, there was limited data on how the practice of intercropping help crops against soil-borne Phytophthora disease. PRINCIPAL FINDINGS: Compared to pepper monoculture, a large scale intercropping study of maize grown between pepper rows reduced disease levels of the soil-borne pepper Phytophthora blight. These reduced disease levels of Phytophthora in the intercropping system were correlated with the ability of maize plants to form a "root wall" that restricted the movement of Phytophthora capsici across rows. Experimentally, it was found that maize roots attracted the zoospores of P. capsici and then inhibited their growth. When maize plants were grown in close proximity to each other, the roots produced and secreted larger quantities of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H-one (DIMBOA and 6-methoxy-2-benzoxazolinone (MBOA. Furthermore, MBOA, benzothiazole (BZO, and 2-(methylthio-benzothiazole (MBZO were identified in root exudates of maize and showed antimicrobial activity against P. capsici. CONCLUSIONS: Maize could form a "root wall" to restrict the spread of P. capsici across rows in maize and pepper intercropping systems. Antimicrobe compounds secreted by maize root were one of the factors that resulted in the inhibition of P. capsici. These results provide new insights into plant-plant-microbe mechanisms involved in intercropping systems.

  18. {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.

  19. Synthesis and Antimicrobial Studies of Novel Billogical Heterocycles

    Institute of Scientific and Technical Information of China (English)

    PATEL,Navin B.; RATHOD,Rahul D.

    2008-01-01

    The synthetic route of sildenafil promoted us to synthesize new object molecules. New analogues containing a 4-thiazolidinone ring bonded to the phenyl moiety at the 2-position, 7-(substituted anilino)-6-fluoro-2-(p-meth-oxy-m- {[2-(p-hydroxyphenyl)-4-oxo- 1,3-thiazolidin-3-yl]aminocarbonyl} phenylsulfonamido)benzothiazoles (4a-41) have been synthesized by cyclization with thioglycollic acid of Schiff bases 3a-31 from corresponding 7-(substituted anilino)-6-fluoro-2-(p-methoxy-m-hydrazinocarbonyl phenylsulfonamido)benzothiazoles (2a-21). Compounds 2a-21 in tum were prepared by dehydroxyhalogenation followed by condensation with hydrazine hy-drates of acids 1a-11. Compounds 1a-11 in turn were prepared by chlorosulfonation of o-methoxy benzoic acid followed by condensation with 6-fluoro-7-(substituted anilino)-2-aminobenzothiazoles. Final compounds have been characterized by their elemental analysis, IR, NMR and mass spectra. All the synthesized compounds have been screened for their antimicrobial activities. Some of them showed good activities.

  20. An insight into the photophysical properties of amide hydrogen bonded N-(benzo[d]thiazol-2-yl) acetamide crystals

    Science.gov (United States)

    Balijapalli, Umamahesh; Udayadasan, Sathiskumar; Panyam Muralidharan, Vivek; Sukumarapillai, Dileep Kumar; Shanmugam, Easwaramoorthi; Paduthapillai Gopal, Aravindan; S. Rathore, Ravindranath; Kulathu Iyer, Sathiyanarayanan

    2017-02-01

    Three distinct, hydrogen bond associated N-(benzo[d]thiazol-2-yl) acetamides were synthesized by refluxing benzothiazoles with acetic acid. The nature of the assemblies was characteristic to the substituent in the benzothiazole moiety. In N-(benzo[d]thiazol-2-yl)acetamide, water acts as a bridge for forming three hydrogen bonds, as an acceptor to amide Nsbnd H, and donors to carbonyl of amide and thiazole nitrogen assembles of three different N-(benzo[d]thiazol-2-yl)acetamide molecules. The N-(6-methylbenzo[d]thiazol-2-yl)acetamide formed a (amide) N-H…N (thiazole) bonded R22(8) molecular dimers by two homo-intermolecular hydrogen bonding interactions. N-(6-methoxybenzo[d]thiazol-2-yl)acetamide formed (amide)N-H…O (acid) & (acid)O-H…N (thiazole) interactions with the acetic acid, forming a R22(8) hydrogen-bonded ring by two hetero-intermolecular hydrogen bonding interactions.

  1. Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil

    Energy Technology Data Exchange (ETDEWEB)

    Li, Zhipeng [School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of the Ministry of Education, Shanghai Jiao Tong University, 200240 (China); Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000 (China); Li, Xiufeng; Zhang, Yawen [School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of the Ministry of Education, Shanghai Jiao Tong University, 200240 (China); Ren, Tianhui, E-mail: thren@sjtu.edu.cn [School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of the Ministry of Education, Shanghai Jiao Tong University, 200240 (China); Zhao, Yidong [Beijing Synchrotron Radiation Facility, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing 100039 (China); Zeng, Xiangqiong; Heide, E. van der [Laboratory for Surface Technology and Tribology, University of Twente, Drienerlolaan 5, 7522 NB Enschede (Netherlands)

    2014-07-01

    A novel long chain alkyl phenylboronic acid ester containing heterocyclic compound, bis (1-(benzothiazol-2-ylthio) propan-2-yl)-4-dodecylphenylboronic acid ester (DBBMT), was synthesized and characterized. The hydrolytic stability of the DBBMT was evaluated and the results show that DBBMT is of outstanding hydrolytic stability compared with normal borate esters, which indicates that the designed molecular structure, by introducing benzene ring to conjugate with the electron-deficient boron and the benzothiazole as a hinder group, is effective on obtaining a hydrolytically stable long chain alkyl phenylboronic acid ester. The tribological properties of DBBMT and ZDDP in mineral base oil were evaluated using a four-ball tribometer, which suggests that the DBBMT possesses comprehensive tribological properties and could be a potential candidate for the replacement of ZDDP. Furthermore, in order to understand the tribological behaviors, the worn surface was analyzed by X-ray photoelectron spectroscopy (XPS) and X-ray absorption near edge structure (XANES) spectroscopy. The results indicate that the elements S, B, O and Fe perform complicated tribochemical reactions to form the compact tribological film composed of B{sub 2}O{sub 3}, FeS, Fe{sub 3}O{sub 4} and FeSO{sub 4}.

  2. Riluzole′s Neuroprotective Effect and the Mechanisms%利鲁唑的神经保护作用及其机制的研究进展

    Institute of Scientific and Technical Information of China (English)

    韩国英; 李春燕(综述); 时海波; 殷善开(审校)

    2015-01-01

    Riluzole(2-p-aminophenyl-6-substituent-benzothiazole) is a benzothiazole compound,which has definite neuroprotective effect.The main mechanisms underlying this effect are likely to be multifaceted , involving suppressing glutamate neurotransmission and neuronal hyperexcitation,promoting the expressing of nerve growth factors via the function of a variety of receptors and related ion channel ,protecting neurons from toxicological damage.Here is to make a review of neuroprotective effect and mechanisms of riluzole to pro-vide a basis for further study.%利鲁唑(2-氨基-6-三氟甲氧基-苯并噻唑)属苯并噻唑类化合物,具有明确的神经保护药理作用。它的主要作用是抑制多种受体和离子通道介导的谷氨酸突触传导和神经元超兴奋性,提高神经营养因子的表达量,保护神经元免受兴奋毒性损伤,促进神经元的存活。该文就利鲁唑神经保护作用及其机制的相关研究进展进行综述。

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

    Science.gov (United States)

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

    2012-04-12

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

  4. Removal of the 2-Mercaptobenotiazole from Model Wastewater by Ozonation

    Directory of Open Access Journals (Sweden)

    Jan Derco

    2014-01-01

    Full Text Available The feasibility of ozonation process for 2-mercaptobenzothiazole (2-MBT removal follows from results of ozonation of the model wastewater. Total removal of 2-MBT was observed after 20 minutes of ozonation. Very good reproducibility of repeated ozonation trials including sampling and analysis was observed. However, the majority of dissolved organic carbon (DOC and chemical oxygen demand (COD remained in the reaction mixture. Benzothiazole (BT and 2-hydroxybenzothiazole (OBT intermediates were identified during degradation of 2-MBT with ozone. In addition to the above benzothiazole derivatives, the creation of some other organic compounds follows from results of mass balance. The best fits of experimental data were obtained using the first kinetic model for 2-MBT and zero-order kinetic model for COD and DOC. The reaction time of 60 minutes can be considered as effective with regard to controlled oxidation in order to increase a portion of partially oxidized substances. Higher biodegradability and lower toxicity of ozonation products on respiration activity of activated sludge microorganisms was observed at higher ozonation time.

  5. Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs.

    Science.gov (United States)

    Maeda, Chihiro; Todaka, Takumi; Ueda, Tomomi; Ema, Tadashi

    2016-05-23

    Several carbazole-based boron dipyrromethene (BODIPY) dyes were synthesized by organometallic approaches. Thiazole, benzothiazole, imidazole, benzimidazole, triazole, and indolone substituents were introduced at the 1-position of the carbazole moiety, and boron complexation of each dipyrrin generated the corresponding compounds 1, 2 a, and 3-6. The properties of these products were investigated by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography, and DFT calculations. These compounds exhibited large Stokes shifts, and compounds 1, 2 a, and 3-5 fluoresced both in solution and in the solid state. Complex 2 a showed the highest fluorescence quantum yield (ΦF ) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2 b-f, which had several different substituents, were prepared and the effects of the substituents on the photophysical properties of the compounds were examined. The fluorescence properties showed good correlation with the results of crystal-packing analyses, and the dyes exhibited color-tunable solid-state fluorescence.

  6. Specific fluorescent detection of fibrillar alpha-synuclein using mono- and trimethine cyanine dyes.

    Science.gov (United States)

    Volkova, K D; Kovalska, V B; Balanda, A O; Losytskyy, M Yu; Golub, A G; Vermeij, R J; Subramaniam, V; Tolmachev, O I; Yarmoluk, S M

    2008-02-01

    With the aim of searching of novel amyloid-specific fluorescent probes the ability of series of mono- and trimethine cyanines based on benzothiazole, pyridine and quinoline heterocycle end groups to recognize fibrillar formations of alpha-synuclein (ASN) was studied. For the first time it was revealed that monomethine cyanines can specifically increase their fluorescence in aggregated ASN presence. Dialkylamino-substituted monomethine cyanine T-284 and meso-ethyl-substituted trimethine cyanine SH-516 demonstrated the higher emission intensity and selectivity to aggregated ASN than classic amyloid stain Thioflavin T, and could be proposed as novel efficient fluorescent probes for fibrillar ASN detection. Studies of structure-function dependences have shown that incorporation of amino- or diethylamino- substituents into the 6-position of the benzothiazole heterocycle yields in a appearance of a selective fluorescent response to fibrillar alpha-synuclein presence. Performed calculations of molecular dimensions of studied cyanine dyes gave us the possibility to presume, that dyes bind with their long axes parallel to the fibril axis via insertion into the neat rows (so called 'channels') running along fibril.

  7. Environmental impact of highway construction and repair materials on surface and ground waters. Case study: crumb rubber asphalt concrete.

    Science.gov (United States)

    Azizian, Mohammad F; Nelson, Peter O; Thayumanavan, Pugazhendhi; Williamson, Kenneth J

    2003-01-01

    The practice of incorporating certain waste products into highway construction and repair materials (CRMs) has become more popular. These practices have prompted the National Academy of Science, National Cooperative Highway Research Program (NCHRP) to research the possible impacts of these CRMs on the quality of surface and ground waters. State department of transportations (DOTs) are currently experimenting with use of ground tire rubber ( crumb rubber) in bituminous construction and as a crack sealer. Crumb rubber asphalt concrete (CR-AC) leachates contain a mixture of organic and metallic contaminants. Benzothiazole and 2(3H)-benzothiazolone (organic compounds used in tire rubber manufacturing) and the metals mercury and aluminum were leached in potentially harmful concentrations (exceeding toxic concentrations for aquatic toxicity tests). CR-AC leachate exhibited moderate to high toxicity for algae ( Selenastrum capriconutum) and moderate toxicity for water fleas ( Daphnia magna). Benzothiazole was readily removed from CR-AC leachate by the environmental processes of soil sorption, volatilization, and biodegradation. Metals, which do not volatilize or photochemically or biologically degrade, were removed from the leachate by soil sorption. Contaminants from CR-AC leachates are thus degraded or retarded in their transport through nearby soils and ground waters.

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

    Energy Technology Data Exchange (ETDEWEB)

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

    1996-12-12

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

  9. Measurement of tire tread in urban air by pyrolysis-gas chromatography with flame photometric detection

    Science.gov (United States)

    Kim, Man Goo; Yagawa, Kazuo; Inoue, Hidenari; Lee, Yong Keun; Shirai, Tsuneo

    The concentration of tire tread in suspended particulate matter (SPM) was measured by a new method based on benzothiazole generated by pyrolysis of vulcanization accelerator. The variation of production yields of benzothiazole was examined for 24 kinds of tire treads currently used in Japan Pyrolysis was carried out at 670°C using a Curie-point pyrolyzer. The vertical profile and diurnal pattern of tire tread were investigated with 4-h samples continuously collected for 24 h at a heavy traffic density area in Tokyo. The diurnal percentage of tire tread in SPM at the sampling site of 86 m height showed two peaks following the trend of traffic density throughout the day. The concentration of tire tread collected at the 86 m level was about 30% of that at the 0 m level during the daytime. The seasonal variation of concentration of tire tread in SPM was measured at the sampling site located 20 km SW of Tokyo. The weight percentage of tire tread in SPM varied between 1.3 and 3% in winter with NE-NW wind and varied between 0.5 and 1.5% in spring with SE-SW wind.

  10. 1,3-Substituted Imidazolidine-2,4,5-triones: Synthesis and Inhibition of Cholinergic Enzymes

    Directory of Open Access Journals (Sweden)

    Josef Jampilek

    2011-09-01

    Full Text Available A series of novel and highly active acetylcholinesterase and butyrylcholinesterase inhibitors derived from substituted benzothiazoles containing an imidazolidine-2,4,5-trione moiety were synthesized and characterized. The molecular structure of 1-(2,6-diisopropyl-phenyl-3-[(1R-1-(6-fluoro-1,3-benzothiazol-2-ylethyl]-imidazolidine-2,4,5-trione (3g was determined by single-crystal X-ray diffraction. Both optical isomers are present as two independent molecules in the triclinic crystal system. The lipophilicity of the compounds was determined as the partition coefficient log Kow using the traditional shake-flask method. The in vitro inhibitory activity on acetylcholinesterase from electric eel and butyrylcholinesterase isolated from equine serum was determined. The inhibitory activity on acetylcholinesterase was significantly higher than that of the standard drug rivastigmine. The discussed compounds are also promising inhibitors of butyrylcholinesterase, as some of the prepared compounds inhibit butyrylcholinesterase better than the internal standards rivastigmine and galanthamine. The highest inhibitory activity (IC50 = 1.66 μmol/L corresponds to the compound 1-(4-isopropylphenyl-3-[(R-1-(6-fluorobenzo[d]thiazol-2-ylethyl]imidazolidine-2,4,5-trione (3d. For all the studied compounds, the relationships between the lipophilicity and the chemical structure as well as their structure-activity relationships are discussed.

  11. Diaquabis(dimethyl sulfoxide-κOdisaccharinatocadmium

    Directory of Open Access Journals (Sweden)

    Fezile S. W. Potwana

    2011-11-01

    Full Text Available The title compound, [Cd(C7H4NO3S2(C2H6OS2(H2O2], contains a Cd2+ cation in an octahedral coordination environment. The metal atom is surrounded by the two different neutral ligands dimethyl sulfoxide (DMSO and water, each coordinating through the O atom. The anionic saccharinate (sac; 1,1,3-trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-ide ligand coordinates through the N atom. Each of the three similar ligand pairs is in a trans configuration with respect to each other. The Cd atom lies on a crystallographic center of symmetry. The DMSO ligand coordinates through the lone pair of electrons on the O atom, as can be seen from the Cd—O—S bond angle of 123.96 (9°.

  12. Corrosion protection of copper by a self-assembled monolayer of alkanethiol

    Energy Technology Data Exchange (ETDEWEB)

    Feng, Y.; Teo, W.K.; Siow, K.S.; Gao, Z.; Tan, K.L.; Hsieh, A.K. [National Univ. of Singapore (Singapore)

    1997-01-01

    A self-assembled monolayer of 1-dodecanethiol (DT) was formed on a copper surface pretreated using different methods. The corrosion protection abilities of the monolayer were evaluated in an air-saturated 0.51 M NaCl solution using various techniques including electrochemical impedance spectroscopy, polarization, coulometry, weight loss, and X-ray photoelectron spectroscopy. It was found that the corrosion resistance of the monolayer was improved markedly by using a nitric acid etching method. A minimum concentration of 10{sup {minus}4} M DT was needed to form a protective monolayer. The DT-monolayer retarded the reduction of dissolved oxygen and inhibited the growth of copper oxide in the NaCl solution. In comparison with other inhibitors, such as benzotriazole (BTA) and mercapto-benzothiazole (MBT), the DT-monolayer showed much better corrosion resistance in aqueous solution.

  13. Analysis of electrochemical noise (ECN) data in time and frequency domain for comparison corrosion inhibition of some azole compounds on Cu in 1.0 M H2SO4 solution

    Science.gov (United States)

    Ramezanzadeh, B.; Arman, S. Y.; Mehdipour, M.; Markhali, B. P.

    2014-01-01

    In this study, the corrosion inhibition properties of two similar heterocyclic compounds namely benzotriazole (BTA) and benzothiazole (BNS) inhibitors on copper in 1.0 M H2SO4 solution were studied by electrochemical techniques as well as surface analysis. The results showed that corrosion inhibition of copper largely depends on the molecular structure and concentration of the inhibitors. The effect of DC trend on the interpretation of electrochemical noise (ECN) results in time domain was evaluated by moving average removal (MAR) method. Accordingly, the impact of square and Hanning window functions as drift removal methods in frequency domain was studied. After DC trend removal, a good trend was observed between electrochemical noise (ECN) data and the results obtained from EIS and potentiodynamic polarization. Furthermore, the shot noise theory in frequency domain was applied to approach the charge of each electrochemical event (q) from the potential and current noise signals.

  14. Discovery of New Anti-Schistosomal Hits by Integration of QSAR-Based Virtual Screening and High Content Screening.

    Science.gov (United States)

    Neves, Bruno J; Dantas, Rafael F; Senger, Mario R; Melo-Filho, Cleber C; Valente, Walter C G; de Almeida, Ana C M; Rezende-Neto, João M; Lima, Elid F C; Paveley, Ross; Furnham, Nicholas; Muratov, Eugene; Kamentsky, Lee; Carpenter, Anne E; Braga, Rodolpho C; Silva-Junior, Floriano P; Andrade, Carolina Horta

    2016-08-11

    Schistosomiasis is a debilitating neglected tropical disease, caused by flatworms of Schistosoma genus. The treatment relies on a single drug, praziquantel (PZQ), making the discovery of new compounds extremely urgent. In this work, we integrated QSAR-based virtual screening (VS) of Schistosoma mansoni thioredoxin glutathione reductase (SmTGR) inhibitors and high content screening (HCS) aiming to discover new antischistosomal agents. Initially, binary QSAR models for inhibition of SmTGR were developed and validated using the Organization for Economic Co-operation and Development (OECD) guidance. Using these models, we prioritized 29 compounds for further testing in two HCS platforms based on image analysis of assay plates. Among them, 2-[2-(3-methyl-4-nitro-5-isoxazolyl)vinyl]pyridine and 2-(benzylsulfonyl)-1,3-benzothiazole, two compounds representing new chemical scaffolds have activity against schistosomula and adult worms at low micromolar concentrations and therefore represent promising antischistosomal hits for further hit-to-lead optimization.

  15. Liberation of copper from amyloid plaques: making a risk factor useful for Alzheimer's disease treatment.

    Science.gov (United States)

    Geng, Jie; Li, Meng; Wu, Li; Ren, Jinsong; Qu, Xiaogang

    2012-11-01

    Alzheimer's disease (AD) is a complex multifactorial syndrome. Metal chelator and Aβ inhibitor are showing promise against AD. In this report, three small hybrid compounds (1, 2, and 3) have been designed and synthesized utilizing salicylaldehyde (SA) based Schiff bases as the chelators and benzothiazole (BT) as the recognition moiety for AD treatment. These conjugates can capture Cu(2+) from Aβ and become dimers upon Cu(2+) coordination and show high efficiency for both Cu(2+) elimination and Aβ assembly inhibition. Besides, the complexes have superoxide dismutase (SOD) activity and significant antioxidant capacity and are capable of decreasing intracellular reactive oxygen species (ROS) and increasing cell viability. All these results indicate that the multifunctional metal complexes which have Aβ specific recognition moiety and metal ion chelating elements show the potential for AD treatment. Therefore, our work will provide new insights into exploration of more potent amyloid inhibitors.

  16. Molecular Design of Near-IR Harvesting Unsymmetrical Squaraine Dyes

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Sanghoon; Mor, Gopal K.; Paulose, Maggie; Varghese, Oomman K.; Baik, Chul; Grimes, Craig A.

    2010-08-17

    The functionalized unsymmetrical benzothiazole squaraine organic sensitizers 5-carboxy-2-({3-[(3-hexylbenzothiazol-2(3H)-ylidene)methyl]-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene}methyl)-1-hexyl-3,3-dimethyl-3H-indolium (hereafter named as SK-11) and 5-carboxy-2-({3-[(3-hexyl-5-methoxybenzothiazol-2(3H)-ylidene)methyl]-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene}methyl)-1-hexyl-3,3-dimethyl-3H-indolium (coded as SK-12) are designed and developed to observe an intense and wider absorption band in the red/NIR wavelength region. DFT/TDDFT calculations have been performed on the two unsymmetrical squaraine sensitizers to gain insight into their electronic and optical properties. The utility of these dyes in solid state dye sensitized solar cells (SS-DSSCs) is demonstrated.

  17. Application of electrochemical frequency modulation for monitoring corrosion and corrosion inhibition of iron by some indole derivatives in molar hydrochloric acid

    Energy Technology Data Exchange (ETDEWEB)

    Khaled, K.F. [Electrochemistry Research Laboratory, Chemistry Department, Faculty of Education, Ain Shams University, Roxy, Cairo (Egypt)], E-mail: khaled@asunet.shams.edu.eg

    2008-11-15

    The corrosion inhibition effect of four indole derivatives, namely indole (IND), benzotriazole (BTA), benzothiazole (BSA) and benzoimidazole (BIA), have been used as possible corrosion inhibitors for pure iron in 1 M HCl. In this study, electrochemical frequency modulation, EFM was used as an effective method for corrosion rate determination in corrosion inhibition studies. By using EFM measurements, corrosion current density was determined without prior knowledge of Tafel slopes. Corrosion rates obtained using EFM, were compared to that obtained from other chemical and electrochemical techniques. The results obtained from EFM, EIS, Tafel and weight loss measurements were in good agreement. Tafel polarization measurements show that indole derivatives are cathodic-type inhibitors. Molecular simulation studies were applied to optimize the adsorption structures of indole derivatives. The inhibitor/iron/solvent interfaces were simulated and the adsorption energies of these inhibitors were calculated. Quantum chemical calculations have been performed and several quantum chemical indices were calculated and correlated with the corresponding inhibition efficiencies.

  18. Electrospray Ionization Mass Spectra of Dipeptide Derivatives

    Institute of Scientific and Technical Information of China (English)

    LUO, Zaigang; ZENG, Chengchu; YANG, Daoshan; HUANG, Yali; WANG, Fang; DU, Hongguang; HU, Liming

    2009-01-01

    Based on the structure of the HIV integrase core domain, dipeptide derivatives, as a type of HIV integrase in- hibitor, were synthesized, and their fragmentation pathways were investigated by electrospray ionization mass spec- trometry (ESI-MSN) in conjunction with tandem mass spectrometry (MS/MS). In order to better understand the fragmentation pathways, the MS2 and MS3 spectra of the title compound were obtained. The main fragmentation pathways occur by the cleavage of the C-CO bonds between N-(benzothiazol-2-yl)aminocarbonyl and methylene, NH-CO bonds between the NH groups and carbonyl groups. Electrospray ionization was proven to be a good method for the structural characterization and identification of this kind of compound.

  19. An excited state intramolecular proton transfer dye based fluorescence turn-on probe for fast detection of thiols and its applications in bioimaging

    Science.gov (United States)

    Zhao, Yun; Xue, Yuanyuan; Li, Haoyang; Zhu, Ruitao; Ren, Yuehong; Shi, Qinghua; Wang, Song; Guo, Wei

    2017-03-01

    In this study, a new fluorescent probe 2-(2‧-hydroxy-5‧-N-maleimide phenyl)-benzothiazole (probe 1), was designed and synthesized by linking the excited state intramolecular proton transfer (ESIPT) fluorophore to the maleimide group for selective detection of thiols in aqueous solution. The fluorescence of probe 1 is strongly quenched by maleimide group through the photo-induced electron transfer (PET) mechanism, but after reaction with thiol, the fluorescence of ESIPT fluorophore is restored, affording a large Stokes shifts. Upon addition of cysteine (Cys), probe 1 exhibited a fast response time (complete within 30 s) and a high signal-to-noise ratio (up to 23-fold). It showed a high selectivity and excellent sensitivity to thiols over other relevant biological species, with a detection limit of 3.78 × 10- 8 M (S/N = 3). Moreover, the probe was successfully applied to the imaging of thiols in living cells.

  20. Pure RGB Emissions Based on a White OLED Combined with Optical Colour Filters

    Institute of Scientific and Technical Information of China (English)

    WU Xiao-Ming; HUA Yu-Lin; WANG Zhao-Qi; YIN Shou-Gen; ZHENG Jia-Jin; DENG Jia-Chun; M. C. Petty

    2006-01-01

    @@ We report on a white organic light emitting device (OLED) with a single light emitting layer consisting of a greenish-white emitting host bis-(2-(2-hydroxyphenyl) benzothiazole)zinc (Zn(BTZ)2) and an orange-red dopant 5,6,11,12-tetraphenylnaphthacene (rubrene). The Commission Internationale De L'Eclairage (CIE) coordinates, external quantum efficiency, and brightness of the white OLED are (0.341, 0.334), 0.63% and 4000 Cd/m2 at the bias of 20 V, respectively. Pure red-green-blue (RGB) emissions have been successfully achieved from the white OLED combined well with several built-in optical colour filters (CFs). The CIE coordinates of the white mixture calculated in theory are very close to the coordinates of the white mixture which recorded with spectrophotometer in practice.

  1. Reaction of 2,3-Dihydro-1,5-benzothiazepines and Phenylacetyl Chloride in the Presence of Triethylamine:A New Aspect on the Formation Mechanism of Dihydro-1,3-oxazin-4-one Derivatives

    Institute of Scientific and Technical Information of China (English)

    XU Jia-Xi许家喜; WANG Chao王超; ZHANG Qi-Han张奇涵

    2004-01-01

    2a,4-Disubstituted 2,2a,3,4-tetrahydro-2-phenyl-1H-azeto[2,1-d][1,5]benzothiazepin-1-ones, as well as 2-substituted 2,3-dihydro-3-phenylacetyl-2-styryl-benzothiazoles and 4a,6-disubstituted 3-benzyl-4a,5-dihydro-2-phenyl1H,6H-[1,3]oxazino[2,3-d][1,5]benzothiazepin-1-ones, were obtained from the reaction of 2,4-disubstituted 2,3-dihydro-1,5-benzothiazepines with phenylacetyl chloride in the presence of triethylamine. The mechanism for the formation of 4a,5-dihydro-1H,6H-[1,3]oxazino[2,3-d][1,5]benzothiazepin-1.-ones, 2,3-dihydro-1,3-oxazin-4-one derivatives, was suggested..

  2. Nucleophilic fluorination of aromatic compounds

    Energy Technology Data Exchange (ETDEWEB)

    Satyamurthy, Nagichettiar; Barrio, Jorge R

    2014-03-18

    Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO.sub.2) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18]fluoride ion derived from anhydrous [F-18](F/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me.sub.4NF, Et.sub.4NF, n-Bu.sub.4NF, (PhCH.sub.2).sub.4NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F-18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.

  3. Synthesis and Spectral Study of Novel Norfloxacin Derivatives

    Directory of Open Access Journals (Sweden)

    Pradeep Yadav

    2008-01-01

    Full Text Available Reaction of [1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl-quinolone-3-carboxylic acid (norfloxacin with thiazole / benzothiazole diazonium chloride to get new piperazine substituted norfloxacin derivative. These norfloxacin derivatives were further condensed with various β-diketone to get novel acid derivatives of 1-Ethyl-6-fluoro-4-oxo-7- [4 (thiazol-2-yldiazenyl-piperzin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid (6a-e and 7-(4-(benzo[d]thiazol-2-yldiazenylpiperazin-1-yl-1-ethyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (6 f-j. Structures of these compounds were established on the basis of spectral studies viz. IR, 1H NMR etc.

  4. Molecular, crystal, and electronic structure of the cobalt(II) complex with 10-(2-benzothiazolylazo)-9-phenanthrol

    Energy Technology Data Exchange (ETDEWEB)

    Linko, R. V., E-mail: rlinko@mail.ru [Peoples' Friendship University of Russia (Russian Federation); Sokol, V. I. [Russian Academy of Sciences, Kurnakov Institute of General and Inorganic Chemistry (Russian Federation); Polyanskaya, N. A.; Ryabov, M. A.; Strashnov, P. V.; Davydov, V. V. [Peoples' Friendship University of Russia (Russian Federation); Sergienko, V. S. [Russian Academy of Sciences, Kurnakov Institute of General and Inorganic Chemistry (Russian Federation)

    2013-05-15

    The reaction of 10-(2-benzothiazolylazo)-9-phenanthrol (HL) with cobalt(II) acetate gives the coordination compound [CoL{sub 2}] {center_dot} CHCl{sub 3} (I). The molecular and crystal structure of I is determined by X-ray diffraction. The coordination polyhedron of the Co atom in complex I is an octahedron. The anion L acts as a tridentate chelating ligand and is coordinated to the Co atom through the phenanthrenequinone O1 atom and the benzothiazole N1 atom of the moieties L and the N3 atom of the azo group to form two five-membered metallocycles. The molecular and electronic structures of the compounds HL, L, and CoL{sub 2} are studied at the density functional theory level. The results of the quantum-chemical calculations are in good agreement with the values determined by X-ray diffraction.

  5. Optical and Thermal Properties of Nickel-Azo Dyes for Digital Versatile Disc-Recordable

    Institute of Scientific and Technical Information of China (English)

    魏斌; 吴谊群; 顾冬红; 干福熹

    2003-01-01

    We investigate the absorption spectra, optical constants and thermal decomposition as well as red-light (650 nm)static recording properties of three novel nickel-azo dye filrns based on 4-methylthiazole, benzothiazole and 6-methylbenzothiazole. Particularly, we obtain the nickel-azo complex film based on 4-methylthiazole, peaking at 562nm and 613nm, with higher refractive index (n = 2.46) and lower extinction coefficient (k = 0.18) at the wavelength 650nm and a sharp threshold of thermal decomposition at 330℃. The results of the static optical recording test of this dye film indicate that high reflectivity contrast of 51% can be observed at a laser writing power of 5.9mW and pulse width of 350ns. These results imply that the nickel-azo complex based on 4-methylthiazole is a promising candidate for a recording medium of digital versatile disc-recordable.

  6. Estimation of optical chemical shift in nuclear spin optical rotation

    Energy Technology Data Exchange (ETDEWEB)

    Chen, Fang [Department of Chemical Physics, University of Science and Technology of China, Hefei, Anhui 230026 (China); Yao, Guo-hua [Key Laboratory of Ion Beam Bio-engineering, Institute of Technical Biology and Agriculture Engineering, Hefei Institutes of Physical Science, Chinese Academy of Sciences, Hefei 230031 (China); He, Tian-jing [Department of Chemical Physics, University of Science and Technology of China, Hefei, Anhui 230026 (China); Chen, Dong-ming, E-mail: dmchen@ustc.edu.cn [Department of Chemical Physics, University of Science and Technology of China, Hefei, Anhui 230026 (China); Liu, Fan-chen, E-mail: fcliu@ustc.edu.cn [Department of Chemical Physics, University of Science and Technology of China, Hefei, Anhui 230026 (China)

    2014-05-19

    Highlights: • Analytical theory of nuclear spin optical rotation (NSOR) is further developed. • Derive formula of NSOR ratio R between different nuclei in a same molecule. • Calculated results of R agree with the experiments. • Analyze influence factors on R and chemical distinction by NSOR. - Abstract: A recently proposed optical chemical shift in nuclear spin optical rotation (NSOR) is studied by theoretical comparison of NSOR magnitude between chemically non-equivalent or different element nuclei in the same molecule. Theoretical expressions of the ratio R between their NSOR magnitudes are derived by using a known semi-empirical formula of NSOR. Taking methanol, tri-ethyl-phosphite and 2-methyl-benzothiazole as examples, the ratios R are calculated and the results approximately agree with the experiments. Based on those, the important influence factors on R and chemical distinction by NSOR are discussed.

  7. Evaluation of impedance measurements on mild steel corrosion in acid media in the presence of heterocyclic compounds

    Energy Technology Data Exchange (ETDEWEB)

    Popova, A. [Department of Physical Chemistry, University of Chemical Technology and Metallurgy, 8 Kl. Ohridski Street, 1756 Sofia (Bulgaria)]. E-mail: chr@uctm.edu; Christov, M. [Department of Physical Chemistry, University of Chemical Technology and Metallurgy, 8 Kl. Ohridski Street, 1756 Sofia (Bulgaria)

    2006-10-15

    Five heterocyclic compounds, having a five atom ring, fused with the benzene ring (indole, benzimidazole, benzotriazole, benzothiazole and benzothiadiazole) were investigated as corrosion inhibitors of mild steel in 1 N HCl using impedance and polarisation resistance methods. Four of these compounds exhibit inhibition properties, while one of them, benzothiadiazole, stimulates the corrosion process. Adequate structure models of the interface are offered. The experimental data show a frequency distribution and therefore a modelling element with frequency dispersion behaviour, a constant phase element (CPE) has been used. At high inhibitor concentrations a second time constant is observed in the impedance spectra. The values of the polarisation resistance determined by the polarisation resistance method are well correlated with the sum of the separate resistances from the impedance measurements.

  8. Cinchona Alkaloid Derivative-Catalyzed Enantioselective Synthesis via a Mannich-Type Reaction and Antifungal Activity of β-Amino Esters Bearing Benzoheterocycle Moieties

    Directory of Open Access Journals (Sweden)

    Han Xiao

    2014-04-01

    Full Text Available An efficient synthesis of highly functionalized chiral β-amino ester derivatives containing benzothiophene and benzothiazole moieties is developed by a Mannich-type reaction using a cinchona alkaloid-derived thiourea catalyst. The desired products were obtained in good yields and high enantioselectivities (~86% yield, >99% ee using to the optimized reaction conditions. The synthesized compounds were characterized by 1H-NMR, 13C-NMR, IR, and HREI-MS analyses. The bioassays identified that compound 5dr has excellent antifungal activity, with a 60.53% inhibition rate against F. oxysporum, higher than that of the commercial agricultural fungicide hymexazol, whose inhibition rate was 56.12%.

  9. Synthesis and evaluation of new organic and phosphorous derivatives against ionizing radiation: study of the in vitro mechanism of action; Synthese et evaluation de nouveaux composes organiques et phosphores contre les effets des rayonnements ionisants. Etude de leur mecanisme d'action in vitro

    Energy Technology Data Exchange (ETDEWEB)

    Prouillac, C

    2006-10-15

    This work falls under a research program. The aim was to synthesize new organic phosphorylated compounds having an interesting radio pharmacological activity without toxicity. That is why, we carried out the synthesis of new benzothiazole and thiadiazole N-substituted derivatives as thiols, amino thiols, acids thio-sulfonic and phosphoro thioates. All these compounds were characterized by NMR (proton, carbon, phosphorus, 2D), by mass spectrometry, elementary analyzes and for some of them by diffraction of x-rays. The activity of the majority of them was evaluated by in vitro tests. The experimental results were confirmed by theoretical study: the aim of D.F.T. calculation was the study of the mechanism of capture of the free radicals by our compounds. In addition, a study of relation structure activity (Q.S.A.R.) was carried out. Our results allow us to create a model making it possible to establish structure-activity relationship. (author)

  10. Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles.

    Science.gov (United States)

    Kojima, Masahiro; Kanai, Motomu

    2016-09-26

    Catalytic acceptorless dehydrogenation is an environmentally benign way to desaturate organic compounds. This process is traditionally accomplished with transition-metal-based catalysts. Herein, a borane-catalyzed, metal-free acceptorless dehydrogenation of saturated N-heterocycles is disclosed. Tris(pentafluorophenyl)borane was identified as a versatile catalyst, which afforded several synthetically important N-heteroarenes in up to quantitative yield. Specifically, the present metal-free catalytic system exhibited a uniquely high tolerance toward sulfur functionalities, and demonstrated superior reactivity in the synthesis of benzothiazoles compared to conventional metal-catalyzed systems. This protocol can thus be regarded as the first example of metal-free acceptorless dehydrogenation in synthetic organic chemistry.

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

    Science.gov (United States)

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

    2015-12-24

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

  12. Spectral Fine Tuning of Cyanine Dyes: Electron Donor-Acceptor Substituted Analogues of Thiazole Orange†

    Science.gov (United States)

    Rastede, Elizabeth E.; Tanha, Matteus; Yaron, David; Watkins, Simon C.; Waggoner, Alan S.; Armitage, Bruce A.

    2015-01-01

    The introduction of electron donor and acceptor groups at strategic locations on a fluorogenic cyanine dye allows fine-tuning of the absorption and emission spectra while preserving the ability of the dye to bind to biomolecular hosts such as double-stranded DNA and a single-chain antibody fragment originally selected for binding to the parent unsubstituted dye, thiazole orange (TO). The observed spectral shifts are consistent with calculated HOMO-LUMO energy gaps and reflect electron density localization on the quinoline half of TO in the LUMO. A dye bearing donating methoxy and withdrawing trifluoromethyl groups on the benzothiazole and quinoline rings, respectively, shifts the absorption spectrum to sufficiently longer wavelengths to allow excitation at green wavelengths as opposed to the parent dye, which is optimally excited in the blue. PMID:26171668

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

    Directory of Open Access Journals (Sweden)

    Eduardo Soriano

    2015-12-01

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

  14. All-optical switching and nonlinear optical properties of HBT in ethanol solution

    Institute of Scientific and Technical Information of China (English)

    Zheng Jia-Jin; Zhang Gui-Lan; Guo Yang-Xue; Li Xiang-Ping; Chen Wen-Ju

    2007-01-01

    This paper demonstrates an all-optical switching model system comprising a single pulsed pump beam at 355 nm and a CW He-Ne signal beam at 632.8 nm with 2-(2'-hydroxyphenyl)benzothiazole (HBT) in ethanol solution. The origins of the optical switching effect were discussed. By the study of nonlinear optical properties for HBT in ethanol solvent, this paper verified that the excited-state intramolecular proton transfer (ESIPT) effect of HBT and the thermal effect of solvent worked on quite different time scales and together induced the change of the refractive index of HBT solution, leading to the signal beam deflection. The results indicated that the HBT molecule could be an excellent candidate for high-speed and high-sensitive optical switching devices.

  15. Efficient synthesis of 2-amino-6-arylbenzothiazoles via Pd(0) Suzuki cross coupling reactions: potent urease enzyme inhibition and nitric oxide scavenging activities of the products.

    Science.gov (United States)

    Gull, Yasmeen; Rasool, Nasir; Noreen, Mnaza; Nasim, Faiz-Ul-Hassan; Yaqoob, Asma; Kousar, Shazia; Rasheed, Umer; Bukhari, Iftikhar Hussain; Zubair, Muhammad; Islam, Md Saiful

    2013-07-25

    In general, benzothiazole derivatives have attracted great interest due to thier pharmaceutical and biological importance. New 2-amino-6-arylbenzothiazoles were synthesized in moderate to excellent yields via Suzuki cross coupling reactions using various aryl boronic acids and aryl boronic acid pinacol esters and the antiurease and nitric oxide (NO) scavenging activity of the products were also examined. The most active compound concerning urease enzyme inhibition was 6-phenylbenzo[d]thiazole-2-amine 3e, with an IC₅₀ value of 26.35 µg/mL. Compound 3c, 6-(4-methoxyphenyl) benzo[d]thiazole-2-amine, exhibited the highest nitric oxide percentage scavenging at 100 µg/mL.

  16. Efficient Synthesis of 2-Amino-6-Arylbenzothiazoles via Pd(0 Suzuki Cross Coupling Reactions: Potent Urease Enzyme Inhibition and Nitric Oxide Scavenging Activities of the Products

    Directory of Open Access Journals (Sweden)

    Md. Saiful Islam

    2013-07-01

    Full Text Available In general, benzothiazole derivatives have attracted great interest due to thier pharmaceutical and biological importance. New 2-amino-6-arylbenzothiazoles were synthesized in moderate to excellent yields via Suzuki cross coupling reactions using various aryl boronic acids and aryl boronic acid pinacol esters and the antiurease and nitric oxide (NO scavenging activity of the products were also examined. The most active compound concerning urease enzyme inhibition was 6-phenylbenzo[d]thiazole-2-amine 3e, with an IC50 value of 26.35 µg/mL. Compound 3c, 6-(4-methoxyphenyl benzo[d]thiazole-2-amine, exhibited the highest nitric oxide percentage scavenging at 100µg/mL.

  17. Experimental chemotherapy of filariasis: comparative evaluation of the efficacy of filaricidal compounds in Mastomys coucha infected with Litomosoides carinii, Acanthocheilonema viteae, Brugia malayi and B. pahangi.

    Science.gov (United States)

    Zahner, H; Schares, G

    1993-01-01

    Eleven types/classes of compound with antifilarial activity were comparatively evaluated in Mastomys coucha infected with Litomosoides carinii, Acanthocheilonema viteae, Brugia malayi or B. pahangi. The paper deals with the efficacy of (i) predominantly microfilaricidal compounds [diethylcarbamazine, levamisole, avermectins (ivermectin, milbemycin), nitrofurans (nitrofurantoin, hydroxymethylnitrofurantoin, nifurtimox, furazolidone, furapyrimidone), organophosphorals (metrifonate, haloxon), and aminophenyl-amidines], (ii) predominantly macrofilaricidal compounds [suramin, benzimidazoles (flubendazole, mebendazole, oxfendazole, ciclobendazole, albendazole, cambendazole, fenbendazole), and arsenicals (thiacetarsamide, Mel PH, R7/45)], and (iii) micro- and macrofilaricidal compounds [benzazole derivatives (CGP 20376 and other benzothiazoles) and nitrophenylamines (amoscanate, CGP 6140)]. Minimum effective doses against microfilariae and minimum curative doses against adult filariae as well as detailed data on dose-efficacy relationships are reported for the various drugs. The results obtained in M. coucha are compared with those published for other experimental in vivo filarial systems, thus attempting to describe a general status of in vivo antifilarial activity of the compounds.

  18. Patch Testing With Shoe Series In Suspected Cases Of Footwear Dermatitis

    Directory of Open Access Journals (Sweden)

    Eapen Bell Raj

    2001-01-01

    Full Text Available One hundred fifty nine patients with clinically suspected footwear dermatitis were patch tested to determine the frequency of positivity of common footwear antigens. Patch testing was done with 22 allergens of Shoe series (Chemotechnique Diagnostics AB Sweden extended with neomycin, gentamycin, soframycin, paraben, cresol and lanolin. Forty- two percent of patients was sensitive to footwear allergen(s whereas the overall positivity was 62%. Potassium dichromate. 2 mercapto- benzothiazole (MBT and nickel sulphate were the frequent sensitizers followed by gentamycin, neomycin, gluteraldehyde, formaldehyde, diphenyl guanidine, diphenyl thiourea, dibutyl thiourea, para-tertiary butyl phenol and 4 aminoazobenzene. Dorsa of feet was the commonest site. potassium dichromate sensitivity was higher in males and the history was not always helpful in incriminating the antigen.

  19. Novel fluoroquinolone derivatives bearing N-thiomide linkage with 6-substituted-2-aminobenzothiazoles: Synthesis and antibacterial evaluation

    Directory of Open Access Journals (Sweden)

    Prabodh Chander Sharma

    2017-02-01

    Full Text Available A series of novel fluoroquinolone derivatives bearing N-thiomide linkage with 6-substituted-2-aminobenzothiazole substituents at the C-7 position were synthesized to obtain potent analogs active against bacterial strains. Some compounds exhibited excellent antibacterial activity against Staphylococcus auerus, Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa bacterial strains. Among all the synthesized compounds 6-nitro substituted benzothiazole along with norfloxacin (4b and gatifloxacin (4l showed MIC 05 μg/ml when tested against S. auerus. Moreover, compounds 4d, 4f and 4l showed superior MIC (15, 10, and 15 μg/ml respectively against B. subtilis. The results of the present study reveal that the compounds have significant antibacterial potential and are suitable candidates for further exploration.

  20. 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.

  1. Molecular indicators for pollution source identification in marine and terrestrial water of the industrial area of Kavala city, North Greece

    Energy Technology Data Exchange (ETDEWEB)

    Grigoriadou, A. [Department of Mineralogy-Petrology-Economic Geology, School of Geology, Aristotle University of Thessaloniki, 54124 Thessaloniki (Greece)], E-mail: grigoriadou@lek.rwth-aachen.de; Schwarzbauer, J. [Institute of Geology and Geochemistry of Petroleum and Coal, Aachen University of Technology, Lochnerstrasse 4-20, 52056 Aachen (Germany)], E-mail: schwarzbauer@lek.rwth-aachen.de; Georgakopoulos, A. [Department of Mineralogy-Petrology-Economic Geology, School of Geology, Aristotle University of Thessaloniki, 54124 Thessaloniki (Greece)], E-mail: ageorgak@geo.auth.gr

    2008-01-15

    Eight terrestrial and four marine water samples were collected from the industrial section of the city of Kavala in northern Greece to determine the occurrence and distribution of organic contaminants, as well as to identify the molecular markers of different emission sources. The samples were analyzed by means of non-target screening analyses. The analytical procedure included a sequential extraction of the samples, GC-FID, GC/MS analyses, and additional quantitative analyses of selected pollutants. The results show a wide variety of compounds including halogenated compounds, technical additives and metabolites, phosphates, phthalates, benzothiazoles, etc. A close relationship between many of the contaminants and their emission sources was determined based on their molecular structures and information on technical applications. - Organic contaminants were used to estimate the state of the pollution and to identify sources in an area impacted by numerous anthropogenic activities.

  2. Determination of sulfur and nitrogen compounds during the processing of dry fermented sausages and their relation to amino acid generation.

    Science.gov (United States)

    Corral, Sara; Leitner, Erich; Siegmund, Barbara; Flores, Mónica

    2016-01-01

    The identification of odor-active sulfur and nitrogen compounds formed during the processing of dry fermented sausages was the objective of this study. In order to elucidate their possible origin, free amino acids (FAAs) were also determined. The volatile compounds present in the dry sausages were extracted using solvent assisted flavor evaporation (SAFE) and monitored by one and two-dimensional gas chromatography with different detectors: mass spectrometry (MS), nitrogen phosphorous (NPD), flame photometric (FPD) detectors, as well as gas chromatography-olfactometry. A total of seventeen sulfur and nitrogen compounds were identified and quantified. Among them, 2-acetyl-1-pyrroline was the most potent odor active compound, followed by methional, ethylpyrazine and 2,3-dihydrothiophene characterized by toasted, cooked potato, and nutty notes. The degradation of FAAs, generated during processing, was related to the production of aroma compounds, such as methionine forming methional and benzothiazole while ornithine was the precursor compound for 2-acetyl-1-pyrroline and glycine for ethylpyrazine.

  3. Adsorption and sub-nanomolar sensing of thioflavin T on colloidal gold nanoparticles, silver nanoparticles and silver-coated films studied using surface-enhanced Raman scattering.

    Science.gov (United States)

    Maiti, Nandita; Chadha, Ridhima; Das, Abhishek; Kapoor, Sudhir

    2015-01-01

    Raman and surface-enhanced Raman scattering (SERS) studies of thioflavin T (ThT) in solid, solution, gold nanoparticles (GNPs), silver nanoparticles (SNPs) and silver-coated films (SCFs) were investigated. Concentration-dependent SERS spectrum of ThT in GNPs and SNPs indicated the existence of two possible structures, one with the torsional angle (φ) between benzothiazole and dimethylaminobenzene rings being 37° and the other with φ=90°. The SERS spectrum of ThT in SCFs were similar to the Raman spectrum of solid and solution that suggests φ=37°. In this paper, the high sensitivity of the SERS technique was employed for sub-nanomolar (picomolar) sensing of ThT.

  4. Azobenzene liquid crystalline materials for efficient optical switching with pulsed and/or continuous wave laser beams.

    Science.gov (United States)

    Hrozhyk, Uladzimir A; Serak, Svetlana V; Tabiryan, Nelson V; Hoke, Landa; Steeves, Diane M; Kimball, Brian R

    2010-04-12

    This study compares optical switching capabilities of liquid crystal (LC) materials based on different classes of azobenzene dyes. LCs based on molecules containing benzene rings with nearly symmetrical pi-pi conjugation respond more efficiently to a cw beam than to a nanosecond laser pulse and maintain the changes induced by the beam for tens of hours. Using azo dye molecules containing two benzene rings with push-pull pi-pi conjugation we demonstrate high photosensitivity to both a cw beam as well as nanosecond laser pulse with only 1 s relaxation of light-induced changes in material properties. Even faster, 1 ms restoration time is obtained for azo dye molecules containing hetaryl (benzothiazole) ring with enhanced push-pull pi-pi conjugation. These materials respond most efficiently to pulsed excitation while discriminating cw radiation.

  5. Syntheses and Crystal Structures of Pyrazoline Derivants

    Institute of Scientific and Technical Information of China (English)

    SHI Hai-Bin; JI Shun-Jun; ZHANG Yong

    2005-01-01

    Two pyrazoline derivants 1-(2-benzothiazole)-3-phenyl-5-(3-thiophene)-2- pyrazoline (BPTP) and 1-(2-benzothiazole)-3-(2-thiophene)-5-phenyl-2-pyrazoline (BTPP) have been synthe- sized and their crystal structures were determined by X-ray single-crystal diffraction.Crystal of BPTP belongs to triclinic, space group P with a = 9.4430(11), b = 9.9384(13), c = 9.9394(13) (A), α = 83.107(10), β = 79.947(10), γ = 70.221(7)o, V = 862.42(19) (A)3, Z = 2, Dc = 1.392 g/cm3, μ(MoKα) = 0.316 mm-1, F(000) = 376, λ = 0.71070 (A), (Δρ)max = 0.348, (Δρ)min = -0.481 e/(A)3, the final R = 0.0407 and wR = 0.1055 for 2844 observed reflections with I > 2σ(I).Crystal of BTPP is of monoclinic, space group P21/c with a = 11.6158(17), b = 11.2796(18), c = 13.082(2) (A), α = 90, β = 91.087(4), γ = 90o, V = 1713.7(5) (A)3, Z = 4, Dc = 1.401 g/cm3, μ(MoKα) = 0.318 mm-1, Mr = 361.07, F(000) = 752, λ = 0.71070 (A), (Δρ)max = 0.322, (Δρ)min = -0.330 e/(A)3, the final R = 0.0563 and wR = 0.1058 for 3434 observed reflections with I > 2σ(I).

  6. Radiation dosimetry and biodistribution of the beta-amyloid plaque imaging tracer {sup 11}C-BTA-1 in humans

    Energy Technology Data Exchange (ETDEWEB)

    Thees, S. [Ulm Univ. (Germany). Klinik fuer Nuklearmedizin; Leipzig Univ. (Germany). Klinik und Poliklinik fuer Diagnostische und Interventionelle Radiologie; Neumaier, B.; Glatting, G.; Deisenhofer, S.; Reske, S.N.; Mottaghy, F.M. [Ulm Univ. (Germany). Klinik fuer Nuklearmedizin; Arnim, C.A.F. von [Ulm Univ. (Germany). Abt. fuer Neurologie

    2007-07-01

    Aim: [N-methyl-{sup 11}C]2-(4'-(methylaminophenyl)-benzothiazole({sup 11}C-BTA-1)) is a thioflavin-T derivative that has been one of the promising PET tracers for imaging of amyloid plaque distribution in the Alzheimer patients brain in vivo. The biodistribution and dosimetry of this tracer in humans is presented and compared to the results of a previous dosimetry and biodistribution study of another thioflavin-T derivative [N-methyl-{sup 11}C]2-hydroxy-(4'-(methylaminophenyl)-benzothiazole ({sup 11}C-OH-BTA-1)) in baboons. Methods: Five subjects underwent 2D dynamic PET imaging. Source organs were segmented using a semiautomatic algorithm based on clustering. Residence times for each source organ were determined by analytical integration of an exponential fit of the time activity curves. Finally organ doses were estimated using the software OLINDA/EXM. Results: The administration of 286 {+-} 93 MBq {sup 11}C-BTA-1 was well tolerated by all subjects. Effective radiation dose was 4.3 {mu}Sv/MBq, range 3.6-5.0 {mu}Sv/MBq. In four ofthe five subjects the liver, in one of the subjects the gallbladder was the critical organ. Conclusion: The radiation burden of a single dose of 300 MBq {sup 11}C-BTA-1 is within the accepted limits for research purpose. In contrast to the previous non-human primate study revealing the gallbladder as the critical organ for {sup 11}C-6-OH-BTA-1, we found the liver as the critical organ in humans using {sup 11}C-BTA-1. Possible explanations may be (1) a reduced bile concentration of {sup 11}C-BTA-1 due to the absent OH-group or (2) a different hepatic metabolism of thioflavin derivatives in human and baboon. (orig.)

  7. Study of Synthetic Process of Novel of Fungicides Benthiavalicarb%苯噻菌胺的合成研究

    Institute of Scientific and Technical Information of China (English)

    刘安昌; 贺晓璐; 冯佳丽; 陈露; 邹晓东

    2014-01-01

    对氟苯胺在盐酸的作用下与硫氰酸铵反应得到对氟苯基硫脲,然后在溴的作用下环化得到2-氨基-6-氟苯并噻唑;2-氨基-6-氟苯并噻唑水解并与氯化锌反应得2-氨基-5-氟苯硫酚锌盐;2-氨基-5-氟苯硫酚锌盐与D-丙氨酸-N-羰酐反应得到(R)-1-(6-氟-2-苯噻唑)乙胺。最后,(R)-1-(6-氟-2-苯噻唑)乙胺与L-缬氨酸和氯甲酸异丙酯反应得到目的产物苯噻菌胺,总收率51.2%(以对氟苯胺计)。%P-fluoroaniline reacted with ammonium thiocyanate in the present of hydrochloric acid to give 4-fluoro-phenylthioureas, then 4-fluoro-phenylthioureas reacted with bromine in the solution of chloroform to give the 2-amino-6-fluorol-benzothiazoles. In the present of NaOH, 2-amino-6-fluorol-benzothiazoles hydrolyzed and reacted with ZnCl2 to give the bis(5-fluoro-2-aminothiophenol) zinc salt. (R)-1-(6-fluoro-2-benzothiazoly)ethylamine was prepared by the reaction of bis(5-fluoro-2-aminothiophenol) zinc salt with D-alanine-N-carboxy anhydride. Under the catalytic of NaOH, (R)-1-(6-fluoro-2-benzothiazoly) ethylamine reacted with L-valine and isopropyl chlorocarbonate to give the target production of benthiavalicarb. The total yield is 51.2%(calculation on p-fluoroaniline).

  8. Radiosynthesis and evaluation of [{sup 11}C]BTA-1 and [{sup 11}C]3'-Me-BTA-1 as potential radiotracers for in vivo imaging of {beta}-amyloid plaques

    Energy Technology Data Exchange (ETDEWEB)

    Neumaier, B.; Deisenhofer, S.; Fuerst, D.; Thees, S.; Buck, A.K.; Glatting, G.; Landwehrmeyer, G.B.; Krause, B.J.; Reske, S.N.; Mottaghy, F.M. [Dept. of Nuclear Medicine, Univ. Hospital Ulm (Germany); Arnim, C.A.F. von [Dept. of Neurology, Univ. Hospital Ulm (Germany); Mueller, H.D.; Sommer, C. [Dept. of Neuropathology, Univ. of Mainz (Germany)

    2007-07-01

    Aim: To evaluate the in vitro and in vivo characteristics of [N-methyl-{sup 11}C]2-(4'-(methylaminophenyl))-benzothiazole ([{sup 11}C]BTA-1) as well as [N-methyl-{sup 11}C]2-(3'-methyl-4'-(methylamino)phenyl)-benzothiazole ([{sup 11}C]3'-Me-BTA-1) as diagnostic markers of amyloid-{beta} (A{beta}) in Alzheimer's disease (AD). Material, methods: Brain uptake and clearance was determined in wild-type mice. Binding affinities (K{sub i}) of [{sup 11}C]BTA-1 and [{sup 11}C]3'-Me-BTA-1 for aggregated A{beta}(1-40) fibrils were assessed. Autoradiography was performed on brain sections of AD patients. To demonstrate binding specificity in vivo BTA-1 was injected i.p. in transgenic mice (Tg2576). Brain sections were analysed consecutively. Additionally, a [{sup 11}C]BTA-1 PET study of an AD patient and a healthy control was performed. Results: In mice brain uptake and clearance of [{sup 11}C]BTA-1 is compatible with the half life of {sup 11}C (2 min: 12.7% ID/g; 30 min: 4.6% ID/g). In contrast clearance rate of [{sup 11}C]3'-Me-BTA-1 is too slow (2 mm 4% ID/g; 30 min 12% ID/g) to achieve sufficient clearance of free and non specifically bound radioactivity. K{sub i} of [{sup 11}C]BTA-1 is 11 nmol/l and that of [{sup 11}C]3'-Me-BTA-1 27 nmol/l. Both radioligands label A{beta} selectively and specifically in AD patients and transgenic mice in vitro. The in vivo stained brain sections show a labelling of A{beta} plaques. The AD patient has a higher pre-frontal, parietal and striatal [{sup 11}C]BTA-1 accumulation than the healthy control. Metabolite analysis revealed approximately 75% intact [{sup 11}C]BTA-1 after 30min in plasma. [{sup 11}C]BTA-1 is favourable for in vivo imaging of A{beta} due to its rapid brain entry, sufficient clearance and good binding affinity for A{beta}. Conclusion: The ability to label A{beta} plaques in vivo in human subjects supports the suitability of [{sup 11}C]BTA-1 as a plaque imaging agent. (orig.)

  9. 新型查尔酮衍生物的合成及酪氨酸酶活性%Synthesis and Activity on Tyrosinase of Novel Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    牛超; 李根; 买迪娜; 阿吉艾克拜尔·艾萨

    2014-01-01

    合成了8个新型含苯并噻唑环的查尔酮衍生物及8个酰胺查尔酮,并对化合物的结构进行了表征.生物活性测试结果表明,化合物4d,4h,5d,7b 和7d 表现出一定的酪氨酸酶激动活性,其中化合物7d 对酪氨酸酶的活性最好,其 EC50=9.6μmol/ L,优于阳性对照药8-MOP(EC50=14.8μmol/ L).%Ver-nohia anthelmintica L was endemic plant in Xinjiang, which was often used in the treatment of Vitiligo. It was believed that the chalcone compounds of Ver-nohia anthelmintica L played an important role in this treatment. Since it may activate tyrosinase and improve the melanin production, many chalcone com-pounds and derivatives were described as potential inhibitor on tyrosinase which may act as skin lightening and whitening agents. However, chalcones which showed activator effect were seldom reported. In order to search for chalcones with high activities on tyrosinase, eight novel chalcone derivatives containing benzothiazole and eight amide-derived chalcones were synthesized in this work. All the compounds were identified by 1 H NMR, 13 C NMR, IR, HRMS and evaluated their activator effect on tyrosinase by measuring the oxidation rate of L-dopa. Compared with the reference drug 8-methoxypsoralen, compounds 4d, 4h, 5d, 7b and 7d showed some activator effect on tyrosinase. Amomg them, compound 7d demonstrated more potent activity with EC50 =9. 6 μmol/ L than 8-methoxypsoralen, which EC50 value was 14. 8 μmol/ L. Further structural modification of this novel chalcones containing benzothiazole will be required for improving the solubility of them.

  10. Accumulation of 19 environmental phenolic and xenobiotic heterocyclic aromatic compounds in human adipose tissue.

    Science.gov (United States)

    Wang, Lei; Asimakopoulos, Alexandros G; Kannan, Kurunthachalam

    2015-05-01

    The extensive use of environmental phenols (e.g., bisphenol A) and heterocyclic aromatic compounds (e.g., benzothiazole) in consumer products as well as widespread exposure of humans to these compounds have been well documented. Biomonitoring studies have used urinary measurements to assess exposures, based on the assumption that these chemicals are metabolized and eliminated in urine. Despite the fact that some of these chemicals are moderately lipophilic, the extent of their accumulation in adipose fat tissues has not been convincingly demonstrated. In this study, human adipose fat samples (N=20) collected from New York City, USA, were analyzed for the presence of environmental phenols, including bisphenol A (BPA), benzophenone-3 (BP-3), triclosan (TCS), and parabens, as well as heterocyclic aromatic compounds, including benzotriazole (BTR), benzothiazole (BTH), and their derivatives. BPA and TCS were frequently detected in adipose tissues at concentrations (geometric mean [GM]: 3.95ng/g wet wt for BPA and 7.21ng/g wet wt for TCS) similar to or below the values reported for human urine. High concentrations of BP-3 were found in human adipose tissues (GM: 43.4; maximum: 4940ng/g wet wt) and a positive correlation between BP-3 concentrations and donor's age was observed. The metabolite of parabens, p-hydroxybenzoic acid (p-HB), also was found at elevated levels (GM: 4160; max.: 17,400ng/g wet wt) and a positive correlation between donor's age and sum concentration of parabens and p-HB were found. The GM concentrations of BTR and BTH in human adipose tissues were below 1ng/g, although the methylated forms of BTR (i.e., TTR and XTR) and the hydrated form of BTH (i.e., 2-OH-BTH) were frequently detected in adipose samples, indicating widespread exposure to these compounds. Our results suggest that adipose tissue is an important repository for BP-3 and parabens, including p-HB, in the human body.

  11. Synthesis, characterization and studies on antioxidant and molecular docking of metal complexes of 1-(benzo[d]thiazol-2-yl)thiourea

    Indian Academy of Sciences (India)

    Harinath Yapati; Subba Rao Devineni; Suresh Chirumamilla; Seshaiah Kalluru

    2016-01-01

    In the present study, a new thiourea derivative bearing benzothiazole ligand, 1-(benzo[d]thiazol-2-yl)thiourea (btt) and its ternary metal (Cu(II), Co(II) and Ni(II)) complexes were synthesized. The structural characterization was carried out by micro analysis, IR, 1H-NMR, EPR, UV-Visible spectral analyses, molar conductance and thermal analysis studies. Spectral studies of complexes revealed that the metal complexes have distorted octahedral geometry. Molecular modelling study was performed to evaluate the recognition of target compounds at the 3MNG binding pocket. The docking results revealed that copper complex selectively binds to the crucial amino acid residues in the active site of 3MNG. The in vitro antioxidant activity of the ligand and its metal complexes was assayed by radical scavenging activity (DPPH, H2O2 and NO) and ferric reducing antioxidant power (FRAP) methods. The ligand showed moderate antioxidant activity whereas the metal complexes exhibited better antioxidant activity than that of the ligand. The results of the four methods proved that the copper complex is the most potent antioxidant among all the tested compounds.

  12. Bis(propane-1,3-diaminedisaccharinatonickel(II

    Directory of Open Access Journals (Sweden)

    Gökhan Kaştaş

    2012-04-01

    Full Text Available In the title complex, [Ni(C7H4NO3S2(C3H10N22] or [Ni(sac2(pen2] (sac = saccharinate or 1,1,3-trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-ide and pen = propane-1,3-diamine, the NiII ion sits on an inversion center, being coordinated by two N atoms of the sac ligands, which occupy trans positions, and four N atoms of the bidentate pen ligands to define a distorted octahedral geometry. The pen ligands chelate the metal ion, forming a six-membered ring which adopts a half-chair conformation, while the sac ligands adopt the most common coordination mode. The crystal packing is stabilized by N—H...O hydrogen bonds, which form a one-dimensional network along [010]. It is also supported by an N—H...S hydrogen bond between the amine group of the pen ligand and the sulfonyl group of the sac ligand.

  13. Bis(dimethyl sulfoxide-κObis(saccharinato-κNzinc(II

    Directory of Open Access Journals (Sweden)

    Fezile S. W. Potwana

    2011-12-01

    Full Text Available The title compound, [Zn(C7H4N2O3S2(C2H6OS2], is a neutral four-coordinate complex with a tetrahedral geometry. The metal atom is surrounded by the two dimethyl sulfoxide (DMSO ligands, each coordinating through the O atom, and two anionic saccharinate (1,1,3-trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-ide ligands coordinating through the N atom. The tetrahedral geometry is slightly distorted as is evident from the N—Zn—N bond angle of 113.85 (6°, the O—Zn—O bond angle of 98.92 (6° and O—Zn—N bond angles of 116.96 (6 and 103.93 (6°. The Zn—N bond lengths are 1.9742 (15 and 2.0025 (16 Å. The Zn—O bond lengths are 1.9806 (14 Å and 1.9468 (14 Å. The DMSO ligand coordinates through the lone pair of electrons on the O atom, as can be seen from the Zn—O—S bond angle of 131.30 (8°.

  14. Synthesis of Some New Heterocycles Derived from Phenylacetyl Isothiocyanate

    Institute of Scientific and Technical Information of China (English)

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

    2008-01-01

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

  15. DC- and RF-GD-OES measurements of adsorbed organic monolayers on copper.

    Science.gov (United States)

    Klemm, Denis; Hoffmann, Volker; Wetzig, Klaus; Eckert, Jürgen

    2009-11-01

    Our direct current (DC)- and radiofrequency glow discharge optical emission spectroscopy (RF-GD-OES) measurements of adsorbed organic monolayers were inspired by the work of Shimizu et al., who presented the first example of depth profile analysis of an adsorbed monolayer by RF-GD-OES in 2004. The great potential of RF-GD-OES for analyses of layers with thicknesses in the subnanometer range was surprising. Shimizu et al. discussed not only the qualitative detection of atoms of the organic monolayer (C, H, N, S), but also the determination of the different orientation of the molecules relative to the surface due to a significant peak sequence. This latter assumption was questioned in the analytical community. We intend to demonstrate the potential of the GD-OES technique for surface analysis in terms of reliability and reproducibility by using an advanced vacuum instrumentation and presputtering with silicon. It will be shown that comparable measurements can be reproduced not only with RF-GD-OES but, above all, also with DC-GD-OES. The experimental steps to adsorb thiourea molecules on a copper substrate are described in detail. Further experiments with other organic molecules, e.g. benzotriazole (BTA) or benzothiazole (BTH), disprove the predicted correlation between the orientation of the molecules relative to the surface and the occurrence of peak separation. Ultimately, a quantification of compounds of the organic monolayer in the case of adsorbed thiourea is achieved.

  16. Self-assembled organic thin films on electroplated copper for prevention of corrosion

    Science.gov (United States)

    Tan, Y. S.; Srinivasan, M. P.; Pehkonen, S. O.; Chooi, Simon Y. M.

    2004-07-01

    Self-assembled organic thin films of dodecanethiol (DT), mercaptobenzothiazole (MBT), benzotriazole (BTA), imidazole (IMD) and benzothiazole (BT) are formed by adsorption on the surface of copper thin film used in ultralarge-scale integrated circuits. The films are characterized by x-ray photoelectron spectroscopy. The inhibition of corrosion of these organic thin films is investigated in aerated 0.5 M H2SO4 solutions by electrochemical impedance spectroscopy and potentiodynamic polarization techniques. The presence of these films reduced corrosion by blocking the copper surface from the oxygen dissolved in the acid medium. The relative inhibition efficiencies of these inhibiting agents in preventing copper oxidation are found to be in the order of DT>MBT>BT>BTA>IMD. The effectiveness of the inhibitors increased with the temperature, concentration of the inhibitors, and duration of immersion in the solution. An adsorption model is proposed on the basis of variation of the impedance according to the inhibitor concentration. The stability and packing of the inhibitors on the surface appear to be the most important factors in determining the inhibitive efficiency of the inhibitors. .

  17. 1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity.

    Science.gov (United States)

    Maračić, Silvija; Kraljević, Tatjana Gazivoda; Paljetak, Hana Čipčić; Perić, Mihaela; Matijašić, Mario; Verbanac, Donatella; Cetina, Mario; Raić-Malić, Silvana

    2015-12-01

    Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic (9-17 and 25-28), 7-substituted coumarin (18-23 and 29-30) or penciclovir-like subunit (31a,b-38a) were designed and synthesized to evaluate their antibacterial activities against selected Gram-positive and Gram-negative bacteria. Hybridization approach using environmentally friendly Cu(I)-catalyzed click reaction under microwave irradiation was adopted in the synthesis of regioselective 1,4-disubstituted 1,2,3-triazole tethered heterocycles (9-23 and 25-30), while post-N-alkylation of NH-1,2,3-triazoles afforded both 2,4- (31a-38a) and 1,4-disubstituted (31b-33b, 35b-37b) 1,2,3-triazole regioisomers. The compounds 18-23 and 25-30 revealed fluorescence in the violet region of the visible spectrum with a strong influence of phenyl spacer in 25-30 on both wavelength and emission intensity. Fusion of selected subunits led to new hybrid architecture, benzothiazole-1,2,3-triazole-coumarin 29 that demonstrated extremely narrow spectrum activity towards fastidious Gram-negative bacteria Moraxella catarrhalis. Selected hybrid showed the potency against Moraxella catarrhalis (MIC⩽0.25μg/mL) comparable to that of reference antibiotic azithromycin, which suggested that further investigations are necessary to optimize this potential hit compound as a new anti-Moraxella catarrhalis agent.

  18. Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents.

    Science.gov (United States)

    Agarwal, Devesh S; Anantaraju, Hasitha Shilpa; Sriram, Dharmarajan; Yogeeswari, Perumal; Nanjegowda, Shankara H; Mallu, P; Sakhuja, Rajeev

    2016-03-01

    A series of bile acid (Cholic acid and Deoxycholic acid) aryl/heteroaryl amides linked via α-amino acid were synthesized and tested against 3 human cancer cell-lines (HT29, MDAMB231, U87MG) and 1 human normal cell line (HEK293T). Some of the conjugates showed promising results to be new anticancer agents with good in vitro results. More specifically, Cholic acid derivatives 6a (1.35 μM), 6c (1.41 μM) and 6m (4.52 μM) possessing phenyl, benzothiazole and 4-methylphenyl groups showed fairly good activity against the breast cancer cell line with respect to Cisplatin (7.21 μM) and comparable with respect to Doxorubicin (1 μM), while 6e (2.49μM), 6i (2.46 μM) and 6m (1.62 μM) showed better activity against glioblastoma cancer cell line with respect to both Cisplatin (2.60 μM) and Doxorubicin (3.78 μM) drugs used as standards. Greater than 65% of the compounds were found to be safer on human normal cell line.

  19. In vitro anticancer activities of Schiff base and its lanthanum complex.

    Science.gov (United States)

    Neelima; Poonia, Kavita; Siddiqui, Sahabjada; Arshad, Md; Kumar, Dinesh

    2016-02-15

    Schiff base metal complexes are well-known to intercalate DNA. The La(III) complexes have been synthesized such that they hinder with the role of the topoisomerases, which control the topology of DNA during the cell-division cycle. Although several promising chemotherapeutics have been developed, on the basis of Schiff base metal complex DNA intercalating system they did not proceed past clinical trials due to their dose-limiting toxicity. Herein, we discuss an alternative compound, the La(III) complex, [La(L(1))2Cl3]·7H2O based on a Schiff base ligand 2,3-dihydro-1H-indolo-[2,3-b]-phenazin-4(5H)-ylidene)benzothiazole-2-amine (L(1)), and report in vitro cell studies. Results of antitumor activity using cell viability assay, reactive oxygen species (ROS) generation and nuclear condensation in PC-3 (Human, prostate carcinoma) cells show that the metal complex is more potent than ligand. La(III) complexes have been synthesized by reaction of lanthanum(III) salt in 1:2M ratio with ligands L(1) and 3-(ethoxymethylene)-2,3-dihydro-1H-indolo[2,3-b]-phenazin-4(5H)-ylidene)benzathiazole-2-amine (L(2)) in methanol. The ligands and their La(III) complexes were characterized by molar conductance, magnetic susceptibility, elemental analyses, FT-IR, UV-Vis, (1)H/(13)C NMR, thermogravimetric, XRD, and SEM analysis.

  20. Kinetika vulkanisasi campuran NR/EPDM dengan pendekatan model Deng-Isayev dan Kamal-Sorour

    Directory of Open Access Journals (Sweden)

    Ihda Novia Indrajati

    2014-12-01

    Full Text Available Curing kinetics of natural rubber/ethylene propylene diene monomer (NR/EPDM blends at different ratios of 2,2’-dithiobis(benzothiazole (MBTS and zinc diethyl dithiocarbamate (ZDEC were studied. NR/EPDM blends were prepared using curative migration control technique. Kinetics studies employ Deng-Isayev and Kamal-Sorour models and kinetics parameters were evaluated using measured data from Moving Die Rheometer. Rate constant (k and orders of reaction (n and m were estimated through multivariable optimization using Matlab and activation energy (E was determined using Arrhenius relationship. From the results, it is evident that the experimental data were in a good agreement with Kamal-Sorour model. It is also found that autocatalytic mechanism was more controlling than the others as indicated by k2>k1. Results also shows that rate constants were greatly influenced by temperature and the types of accelerator, while orders of reaction were dependent on temperature and independent on the types and amounts of accelerator. Combination of MBTS and ZDEC reduces energy activation of autocatalytic reaction. For desirable rate of curing, its ratio of 1.4 to 0.2 gave the lowest activation energy.

  1. 3-D QSAR CoMFA study of nitrogen mustards possessing new chemical entities as possible anticancer agents

    Directory of Open Access Journals (Sweden)

    Anand R

    2006-01-01

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

  2. Discovery of gramine derivatives that inhibit the early stage of EV71 replication in vitro.

    Science.gov (United States)

    Wei, Yanhong; Shi, Liqiao; Wang, Kaimei; Liu, Manli; Yang, Qingyu; Yang, Ziwen; Ke, Shaoyong

    2014-01-01

    Enterovirus 71 (EV71) is a notable causative agent of hand, foot, and mouth disease in children, which is associated with an increased incidence of severe neurological disease and death, yet there is no specific treatment or vaccine for EV71 infections. In this study, the antiviral activity of gramine and 21 gramine derivatives against EV71 was investigated in cell-based assays. Eighteen derivatives displayed some degree of inhibitory effects against EV71, in that they could effectively inhibit virus-induced cytopathic effects (CPEs), but the anti-EV71 activity of the lead compound gramine was not observed. Studies on the preliminary modes of action showed that these compounds functioned by targeting the early stage of the EV71 lifecycle after viral entry, rather than inactivating the virus directly, inhibiting virus adsorption or affecting viral release from the cells. Among these derivatives, one (compound 4s) containing pyridine and benzothiazole units showed the most potency against EV71. Further studies demonstrated that derivative 4s could profoundly inhibit viral RNA replication, protein synthesis, and virus-induced apoptosis in RD cells. These results indicate that derivative 4s might be a feasible therapeutic agent against EV71 infection and that these gramine derivatives may provide promising lead scaffolds for the further design and synthesis of potential antiviral agents.

  3. Synthesis and evaluation of {sup 18}f-labeled benzylideneaniline derivatives as new biomarkers for {beta}-amyloid imaging in Alzheimer's disease

    Energy Technology Data Exchange (ETDEWEB)

    B, Rai Ganeaha; Jeong, Jae Min; Lee, Yun Sang; Chang, Young Soo; Kim, Young Ju; Kim, Hyung Woo; Lee, Dong Soo; Chung, June Key; Lee, Myung Chul [Seoul National University College of Medicine, Seoul (Korea, Republic of)

    2005-07-01

    Noninvasive early detection of the A{beta} plaques in Alzheimer's disease (AD) brain may be useful tool for the treatment of AD patients. We herein describe the synthesis of {sup 18}F-labeled benzylideneaniline derivatives utilizing a novel labeling approach for imaging A{beta} plaques in AD patients. Condensation of [{sup 18}F] 4-fluorobenzaldehyde with various aromatic amines afforded {sup 18}F-labeled benzylideneaniline derivatives. The biodistribution of 18F-Iabeled benzylideneaniline derivatives was studied with ICR male mice. The binding affinities of the cold compounds to A{beta} (1-40) were determined using [{sup 125}I] 2-(3'-iodo-4-methylaminophenyl) benzothiazole as a reference standard. The radiochemical yields were 32-44% and radiochemical purities were above 99% after purification. Log P values of the compounds were 1.56-1.58. Some of the benzylideneaniline derivatives showed relatively high binding affinity to A{beta} (1-40) aggregates (Ki 149-304 nM). The {sup 18}F-labeled benzylideneaniline derivatives displayed high brain uptake ratio in normal mice (2.9-24.93). The study suggests that these {sup 18}F-labeled compounds may be suitable for A{beta} plaque imaging in AD patients.

  4. 5-Chlorobenzothiazole-2-spiro-3′-indolin-2′-one

    Directory of Open Access Journals (Sweden)

    Mehmet Akkurt

    2010-02-01

    Full Text Available The title compound, C14H9ClN2OS, crystallizes with two unique molecules, A and B, in the asymmetric unit. The five-membered rings of the benzothiazole groups in both molecules adopt an envelope conformation [puckering parameters: q2 = 0.242 (1 Å and ϕ2 = 217.5 (4° for A, and q2 = 0.234 (1 Å and ϕ2 = 37.7 (4° for B]. The five-membered rings of the indolinone groups in both molecules are also not planar, with a twisted conformation [puckering parameters are q2 = 0.112 (2 Å and ϕ2 = 126.3 (8° for A, and q2 = 0.108 (2 Å and ϕ2 = 306.4 (9° for B]. In the crystal structure, there are intermolecular N—H...O, N—H...S and C—H...O hydrogen-bonding interactions, forming the layers propagating normal to c.

  5. 2-Benzazolyl-4-Piperazin-1-Ylsulfonylbenzenecarbohydroxamic Acids as Novel Selective Histone Deacetylase-6 Inhibitors with Antiproliferative Activity.

    Directory of Open Access Journals (Sweden)

    Lei Wang

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

  6. Biyosid Uygulamalı Giysilik Deri Üretiminde Tabaklama ve Sonrası Yaş İşlemlerde Mikrobiyal Yükün Tespiti Üzerine Bir Araştırma

    Directory of Open Access Journals (Sweden)

    Derya DOĞANAY

    2014-07-01

    Full Text Available In the present research, it was aimed to determine the numbers of total fungi (yeast and mold, proteolytic fungi and lipolytic fungi; total aerobic mesophilic bacteria, proteolytic bacteria, lipolytic bacteria and aerobic sporeforming bacteria that are likely to grow in the floats of chrome tanning, neutralization and post-tanning operations (retanning – fatliquoring - dying in different concentrations of NaCl (0, 5, 10 %. Raw domestic sheep skins were used in the study. While the skins were being processed in soaking and chrome tanning, a commercial bactericide composed of quaternized ammonium compounds and benzothiazole-based fungicide were added respectively. For control, the skins were processed without addition of any bactericide or fungicide. According to results, no bacterial growth was detected in the floats investigated, while some amount of fungal growth was determined. The numbers of total fungi in the chrome tanning and neutralization processes were determined to be between 1,1x101 and 7,0x101 cfu/mL. No total fungi weredetected in retanning – dyeing fatliquoring float; besides, proteolytic and lipolytic fungi were detected in all process steps including retanning – dyeing - fatliquoring. The numbers of the proteolytic fungi were determined to be between the values 1,0x101 and 8,0x101 cfu/mL and those of lipolytic fungi to be between the values 1,0x101 and 7,0x101 cfu/mL

  7. SYNTHESIS, CHARACTERIZATION AND RING-OPENING POLYMERIZATION OF CYCLIC (ARYLENE PHOSPHONATE) OLIGOMERS

    Institute of Scientific and Technical Information of China (English)

    Hong-ming Zhang; Qing-zhong Guo; Tian-lu Chen

    2004-01-01

    A series of cyclic (arylene phosphonate) oligomers were prepared by reaction of phenylphosphonic dichloride (PPD) with various bisphenols under pseudo-high dilution conditions via interfacial polycondensation. The yield of cyclic (arylenc phosphonate) oligomers is over 85% by using hexadecyltrimethylammonium bromide as phase transfer catalyst (PTC) at 0 ℃. The structures of the cyclic oligomers were confirmed by a combination of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) and IR analysis. These cyclic oligomers undergo facile ring-opening polymerization in the melt by using potassium 4,4'-biphenoxide as the initiator to give linear polyphosphonate. Free-radical ring-opening polymerization of cyclic(arylene phosphonate) oligomers containing sulfur linkages was also performed in the melt using 2,2'-dithiobis(benzothiazole) (DTB) as the initiator at 270℃ and the resulting polymer had a Mw of 8 × 103 with a molecular weight distribution of 4. Ring-opening copolymerization of these cyclic oligomers with cyclic carbonate oligomers was also achieved. The average molecular weight of the resulting copolymer is higher than the corresponding homopolymer and the thermal stability of the copolymer is better than the corresponding homopolymer.

  8. The role of local environment on the electronic properties of a novel blue-emitting donor-acceptor compound

    Science.gov (United States)

    Legaspi, Christian M.; Stubbs, Regan E.; Yaron, David J.; Peteanu, Linda A.; Kemboi, Abraham; Picker, Jesse; Fossum, Eric

    2016-09-01

    With the rising popularity of organic light-emitting diodes (OLEDs) in display applications, demand for more efficient blue emitters has increased. We have recently synthesized a novel blue-emitting, donor-acceptor system employing carbazole as the donor and a benzothiazole derivative as the acceptor, BTZ-CBZ. We find that the solution-phase emission of BTZ-CBZ is highly dependent on solvent polarity, both in lineshape and emission maximum, showing a Stokes shift of 50 nm in methylcyclohexane and 150 nm in acetonitrile. This is expected behavior for donor-acceptor compounds due to the presence of a charge-transfer excited state. However, the solid state properties are more important for OLED devices. Using time-dependent density functional theory calculations employing the linear-response (LR) and state-specific (SS) polarizable continuum model (PCM), we explore the effects of solvent reorganization on the emission properties of BTZ-CBZ. SS-PCM reproduces the solvatochromism behavior of BTZ-CBZ in solution, but LR-PCM shows effectively no shift with solvent polarity. We surmise that this is because solvent reorganization is necessary for the solvatochromic effect to occur. The effect of rigid matrices on the emission of BTZ-CBZ has direct implications on its viability as a blue emitter in solid-state OLEDs and which molecular environments will be ideal for devices.

  9. Crystal Structure and Spectroscopic Properties of the Donor-acceptor Complex of 2-Amino-1,3-benzo- thiazole with Ethyl-5,6-benzocoumarin-3-carboxylate

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    The donor-acceptor complex derived from 2-amino-1,3-benzothiazole (ABT) and ethyl 5,6-benzocoumarin-3-carboxylate (EBCC) has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c, with a = 8.6485(3), b = 7.7743(3), c = 29.1963(10) (A), β = 92.0460(10)°, Z = 4, Mr = 418.45, V = 1961.79(12)(A)3, Dc = 1.417 g/cm3, μ = 0.199 mm-1, F(000) = 872, the final R = 0.0350 and wR = 0.1226. The complex is an A…D…D'…A' H-bonded tetramer. The intermolecular N-H…O and N-H…N hydrogen bonds, together with π-π stacking interactions, stabilize the crystal structure by forming a supramolecular architecture. It is found that, in solid state, the fluorescence emission of the complex is quenched significantly while the UV-vis spectrum exhibits a broad band at 346 nm with shoulder, which can be attributed to the donor-acceptor complex formed.

  10. Synthesis of Two Novel Additives and Study of Their Tribological Properties in Rapeseed Oil

    Institute of Scientific and Technical Information of China (English)

    Zhou Maolin; Li Fenfang; Zeng Xiaojun; Fan Chengkai

    2007-01-01

    Two novel ashless additives-benzothiazole derivatives containing boron and chlorine,OBC and BBC,were synthesized.The tribological performances of OBC and BBC at different mass ratios as additives in rapeseed oil(RO)were examined on a four-ball machine.The worn surfaces of the lower steel balls lubricated by oil samples were analyzed by means of scanning electron microscopy (SEM).The test results showed that OBC and BBC had good solubility in the base oil,and could effectively increase the load-carrying capacity of the base Oil.The maximum non-seizure load of oil sample containing 1.5 m% BBCwas 1117N.which was 2.3 times as much as that of the base oil.Both OBC and BBC could improve the anti-wear and corrosion inhibiting performance and thermal stability of the base oil,whose initial decomposition temperatures was above 350℃.However,OBC and BBC at different concentrations could increase the friction coefficient of the base oil.The SEM morphology of steel balls lubricated by oil samples containing 1.5 m%additives seemed to be more uniform and smoother than that of the base oil,and the scars formed were very shallow.

  11. Corrosion inhibitors: Correlation between chemical structure and efficiency

    Energy Technology Data Exchange (ETDEWEB)

    Lukovits, I.; Koszto, T. [Hungarian Academy of Sciences (Hungary). Inst. of Chemistry

    1999-11-01

    Corrosion inhibition efficiencies of heterocyclic aromatic or partially saturated aromatic compounds (pyrimidines, benzothiazole derivatives, amino-acids containing an aromatic part, pyridines and quinolines) were correlated with quan chemical indices of the respective molecules. Inhibition efficiencies measured in acidic solutions containing 0.001 and 0.01 mol/L of the inhibitor, respectively, were collected. The quantum chemical calculations were done by using the simple Hueckel method. Comparison of inhibition efficiencies and the differences between energies of the highest occupied and the lowest unoccupied molecular orbitals {Delta} indicated that if {Delta} is lower than 1.3 (in beta units) then the compound will not be active, whereas if {Delta} > 1.3 beta, the compound may be efficient in 0.001 mole/L concentration. The critical value of {Delta} may be lower in solution with 0.01 mole/L inhibitor concentration. Although {Delta} alone is not sufficient to account for the variation in the experimental inhibition efficiencies, the present result indicates that compounds which may be easily excited will be inefficient inhibitors because they maybe altered or decomposed after the excitation takes place.

  12. A High Affinity Red Fluorescence and Colorimetric Probe for Amyloid β Aggregates

    Science.gov (United States)

    Rajasekhar, K.; Narayanaswamy, Nagarjun; Murugan, N. Arul; Kuang, Guanglin; Ågren, Hans; Govindaraju, T.

    2016-04-01

    A major challenge in the Alzheimer’s disease (AD) is its timely diagnosis. Amyloid β (Aβ) aggregates have been proposed as the most viable biomarker for the diagnosis of AD. Here, we demonstrate hemicyanine-based benzothiazole-coumarin (TC) as a potential probe for the detection of highly toxic Aβ42 aggregates through switch-on, enhanced (~30 fold) red fluorescence (Emax = 654 nm) and characteristic colorimetric (light red to purple) optical outputs. Interestingly, TC exhibits selectivity towards Aβ42 fibrils compared to other abnormal protein aggregates. TC probe show nanomolar binding affinity (Ka = 1.72 × 107 M‑1) towards Aβ42 aggregates and also displace ThT bound to Aβ42 fibrils due to its high binding affinity. The Aβ42 fibril-specific red-shift in the absorption spectra of TC responsible for the observed colorimetric optical output has been attributed to micro-environment change around the probe from hydrophilic-like to hydrophobic-like nature. The binding site, binding energy and changes in optical properties observed for TC upon interaction with Aβ42 fibrils have been further validated by molecular docking and time dependent density functional theory studies.

  13. Highly efficient and concentration-insensitive organic light-emitting devices based on self-quenching-resistant orange–red iridium complex

    Energy Technology Data Exchange (ETDEWEB)

    Qi, Yige; Wang, Xu [State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China); Li, Ming [College of Chemistry, Sichuan University, Chengdu 610064 (China); Lu, Zhiyun, E-mail: luzhiyun@scu.edu.cn [College of Chemistry, Sichuan University, Chengdu 610064 (China); Yu, Junsheng, E-mail: jsyu@uestc.edu.cn [State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)

    2014-11-15

    Orange–red phosphorescent organic light-emitting devices (PHOLEDs) with high efficiency and concentration insensitivity based on a novel iridium complex, bis[2-(biphenyl-4-yl)benzothiazole-N,C{sup 2}′]iridium(III) (acetylacetonate) [(4Phbt){sub 2}Ir(acac)], were fabricated. With the heavily doped emissive layer (EML) of 4,4′-N,N′-dicarbazolylbiphenyl (CBP): (4Phbt){sub 2}Ir(acac) in a wide and easily controlled dopant concentration range from 12 wt% to 24 wt%, a maximum power efficiency of 29 lm/W and an external quantum efficiency of >16% of the PHOLEDs were obtained, implying the insensitivity of electroluminescence (EL) properties to doping concentration. Meanwhile, a maximum power efficiency of 5.0 lm/W was achieved from a non-doped device with neat (4Phbt){sub 2}Ir(acac) as the EML, indicating a superior property of self-quenching resistance. The mechanism of direct exciton formation, in which exciton-formation regions are distributed throughout the EML, is responsible for the significant alleviation of triplet–triplet annihilation and superior EL performance. - Highlights: • Highly efficient and concentration-insensitive PHOLEDs were obtained. • The high efficiency of non-doped PHOLEDs indicated a quenching-resistant property. • The independence of EL spectra on doping concentration was observed. • The heavily doped devices were dominated by mechanism of direct exciton formation.

  14. Effect of inserting of thin Rubrene layer on performance of Organic Light-Emitting Diodes based on Zn(BTz){sub 2}

    Energy Technology Data Exchange (ETDEWEB)

    Tomova, R L; Petrova, P K; Stoycheva-Topalova, R T, E-mail: reni@clf.bas.b [Institute of optical materials and technologies ' Acad. J. Malinowski' , Bulgarian Academy of Sciences, ' Acad. G. Bonchev' str. bl. 109, 1113 Sofia (Bulgaria)

    2010-11-01

    Organic light-emitting diodes (OLEDs) with improved performances are fabricated using a thin (1 nm) yellow-emitting layer of 5,6,11,12-tetraphenylnaphthacene (Rubrene) inserted at different position in green emitting electroluminescent (EL) layer of bis-(2-(2-hydroxyphenyl) benzothiazole)zinc (Zn(BTz){sub 2}) in configuration: ITO/PVK:TPD/ Zn(BTz){sub 2} (x nm)/ Rubrene (1 nm)/ Zn(BTz){sub 2} (75-x nm)/Al, where PVK:TPD is a hole transporting layer of N, N'-bis(3-methylphenyl)-N, N'-diphenylbenzidine (TPD) incorporated in poly(N-vinylcarbazole) (PVK) matrix and Al is a cathode. EL spectra predominantly influenced by Rubrene emission when the doping layer is close to (PVK:TPD)/ Zn(BTz){sub 2} (x{yields} 0-15 nm) and to Zn(BTz){sub 2}/Al (x{yields} 70-75 nm) interfaces and shift toward emission of Zn(BTz){sub 2} increasing the distance of Rubrene from both interfaces (x{yields}35 nm). The same dependence of the EL efficiency on the position of the doping Rubrene layer in the OLED structure was found.

  15. Triplet States of Thioflavin T in Fluorescent Molecular Rotor Model

    Science.gov (United States)

    Kuz‧mitskii, V. A.; Stepuro, V. I.

    2017-01-01

    Quantum-chemical INDO/S calculations of Thiofl avin T have been carried out taking account of variation of the angle φ between the planes of the benzothiazole (BTZ) and dimethylaniline (DMA) rings. It was found that when the angle φ changes from 40° to 90° the energy of the triplet state increases by 4000 cm-1, whereas the energy of the singlet state S 1 decreases by 1900 cm-1 and reaches a minimum. The function {E}_{T_1}(φ) has a minimum at φ = 30°, which is 300 cm-1 less than at φ = 40°. The calculated T 1 S 0 interval at φ = 30-40° amounts to 15,600-16,000 cm-1, which agrees well with the phosphorescence data (17,100-17,400 cm-1). For φ = 80-90° the T 1, T 2 , and T 3 levels ( T 1 and T 2 are lower than S 1 ) are close to the S 1 level. The S 1 and T 3 levels intersect at φ 85°, and at φ = 90° the interval Δ {E}_{S_1{T}_3} amounts to only 100 cm-1 due to the small value of the exchange integral corresponding to electron transfer DMA → BTZ.

  16. 车间空气中6-氯-2-氨基苯骈噻唑的高效液相色谱测定法

    Institute of Scientific and Technical Information of China (English)

    金米聪; 王立; 符展明

    2001-01-01

    @@ 6-氯-2-氨基苯骈噻唑(6-chloro-2-amino-benzothiazole,CABT)是一种重要的偶氮型分散染料中间体,常温下为白色或淡黄色粉状固体,有一定的毒性,特别在烘干、粉碎、包装等生产车间,其粉末易漂浮于空气中,严重危害作业工人的身体健康.目前国内未见空气中CABT测定方法的报道,如按(GB5748-85)[1]测定,则准确度差,灵敏度低,严重制约了CABT空气浮尘的准确监测.我们采用高效液相色谱法(HPLC),以甲醇-水作流动相,C18反相色谱柱分离,225nm波长检测,测定空气中的CABT,报道如下.

  17. Study of thioflavin-T immobilized in porous silicon and the effect of different organic vapors on the fluorescence lifetime.

    Science.gov (United States)

    Hutter, Tanya; Amdursky, Nadav; Gepshtein, Rinat; Elliott, Stephen R; Huppert, Dan

    2011-06-21

    Steady-state and time-resolved emission techniques have been employed to study the fluorescence properties of thioflavin-T (ThT) adsorbed on oxidized porous silicon (PSi) surfaces, with an average pore size of ∼10 nm. We found that the average fluorescence decay time of ThT, when it is adsorbed on the PSi surface, is rather long, τ(av) = 1.3 ns. We attribute this relatively long emission lifetime to the effect of the immobilization of ThT on the PSi surface, which inhibit the rotation of the aniline with respect to the benzothiazole moieties of ThT. We also measured the fluorescence properties of ThT in PSi samples in equilibrium with vapors of several liquids, such as methanol, acetonitrile, and water. We found that the fluorescence intensity drops by a factor of 10, and the average decay time, measured by a time-correlated single-photon counting technique, decreases by a factor of 3. We explain these results in terms of liquid condensation of the vapors in the PSi pores, which leads to partial dissolution of the ThT molecules in the liquid pools.

  18. Competitive binding of a benzimidazole to the histone-binding pocket of the Pygo PHD finger.

    Science.gov (United States)

    Miller, Thomas C R; Rutherford, Trevor J; Birchall, Kristian; Chugh, Jasveen; Fiedler, Marc; Bienz, Mariann

    2014-12-19

    The Pygo-BCL9 complex is a chromatin reader, facilitating β-catenin-mediated oncogenesis, and is thus emerging as a potential therapeutic target for cancer. Its function relies on two ligand-binding surfaces of Pygo's PHD finger that anchor the histone H3 tail methylated at lysine 4 (H3K4me) with assistance from the BCL9 HD1 domain. Here, we report the first use of fragment-based screening by NMR to identify small molecules that block protein-protein interactions by a PHD finger. This led to the discovery of a set of benzothiazoles that bind to a cleft emanating from the PHD-HD1 interface, as defined by X-ray crystallography. Furthermore, we discovered a benzimidazole that docks into the H3K4me specificity pocket and displaces the native H3K4me peptide from the PHD finger. Our study demonstrates the ligandability of the Pygo-BCL9 complex and uncovers a privileged scaffold as a template for future development of lead inhibitors of oncogenesis.

  19. 2-Benzazolyl-4-Piperazin-1-Ylsulfonylbenzenecarbohydroxamic Acids as Novel Selective Histone Deacetylase-6 Inhibitors with Antiproliferative Activity.

    Science.gov (United States)

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

    2015-01-01

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

  20. New benzo[d]thiazol-2-yl-aminoacetamides as potential anticonvulsants: synthesis, activity and prediction of molecular properties.

    Science.gov (United States)

    Ali, Ruhi; Siddiqui, Nadeem

    2015-04-01

    A series of N-(substituted-2-oxo-4-phenylazetidin-1-yl)-2-((6-substitutedbenzo[d]thiazol-2-yl)amino)acetamide derivatives were synthesized using pharmacophoric features with aromatic hydrophobic aryl ring (A), NH-C=O as hydrogen bonding domain, the nitrogen atom as electron donor (D), and phenyl as distal aryl ring (C). The synthesized molecules were initially screened for anticonvulsant activity using the maximal electroshock seizure (MES) test and the subcutaneous pentylenetetrazole test in albino mice. An acute neurotoxicity study on the synthesized molecules was also carried out using the rotarod test. The results of these tests revealed that two compounds, 5b and 5q, showed promising activity with ED50 values of 15.4 and 18.6 mg/kg and protective indices of 20.7 and 34.9 in the MES test, respectively, which are found to be approximately fourfold higher than those of the standard drugs phenytoin (6.9) and carbamazepine (8.1). These molecules may act as lead of the designed scheme. The pharmacokinetic profiles of all the synthesized compounds were estimated using Molinspiration software. None of the compounds violated Lipinski's "rule of five". The possible structure-activity relationship was discussed. In conclusion, this manuscript shows that the developed model has a highly prognostic power for the further investigation of better benzothiazole derivatives for future discovery and development.