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Sample records for benzimidazoles

  1. Recyclization reactions leading to benzimidazoles

    Energy Technology Data Exchange (ETDEWEB)

    Mamedov, Vakhid A; Murtazina, Anna M [A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Centre of the Russian Academy of Sciences, Kazan (Russian Federation)

    2011-05-31

    The published data on the recyclization reactions that afford benzimidazoles are generalized and systematized. Both classical and new methods of benzimidazole synthesis are considered. Attention is focused on the publications over the recent 10-15 years; of the earlier publications, only those unknown to the wide circle of chemists are analyzed.

  2. Di(hydroxyphenyl)- benzimidazole monomers

    Science.gov (United States)

    Connell, John W. (Inventor); Hergenrother, Paul M. (Inventor); Smith, Joseph G. (Inventor)

    1993-01-01

    Di(hydroxyphenyl)benzimidazole monomers were prepared from phenyl-hydroxybenzoate and aromatic bis(o-diamine)s. These monomers were used in the synthesis of soluble polybenzimidazoles. The reaction involved the aromatic nucleophilic displacement of various di(hydroxyphenyl)benzimidazole monomers with activated aromatic dihalides or activated aromatic dinitro compounds in the presence of an alkali metal base. These polymers exhibited lower glass transition temperatures, improved solubility, and better compression moldability over their commercial counterparts.

  3. BENZIMIDAZOLES: THE LATEST INFORMATION ON BIOLOGICAL ACTIVITIES

    OpenAIRE

    Singh Gurvinder; Kaur Maninderjit; Chander Mohan

    2013-01-01

    Benzimidazole is a heterocyclic aromatic organic compound. It is an important pharmacophore and a privileged structure in medicinal chemistry. Benzimidazole and its derivatives play an important role in medical field with large number of Pharmacological activities such as antimicrobial, antiviral, antidiabetic and anticancer activity. This review is summarized to know about the chemistry of different derivatives of benzimidazoles along with their biological actions such as antioxidant, antimi...

  4. Ionic conducting poly-benzimidazoles

    International Nuclear Information System (INIS)

    Over the last years, many research works have been focused on new clean energy systems. Hydrogen fuel cell seems to be the most promising one. However, the large scale development of this technology is still limited by some key elements. One of them is the polymer electrolyte membrane 'Nafion' currently used, for which the ratio performance/cost is too low. The investigations we carried out during this thesis work are related to a new class of ionic conducting polymer, the sulfonated poly-benzimidazoles (sPBI). Poly-benzimidazoles (PBI) are aromatic heterocyclic polymers well-known for their excellent thermal and chemical stability. Ionic conduction properties are obtained by having strong acid groups (sulfonic acid SO3H) on the macromolecular structure. For that purpose, we first synthesized sulfonated monomers. Their poly-condensation with an appropriate non-sulfonated co-monomer yields to sPBI with sulfonation range from 0 to 100 per cent. Three different sPBI structures were obtained, and verified by appropriate analytical techniques. We also showed that the protocol used for the synthesis resulted in high molecular weights polymers. We prepared ionic conducting membrane by casting sPBI solutions on glass plates. Their properties of stability, water swelling and ionic conductivity were investigated. Surprisingly, the behaviour of sPBI was quite different from the other sulfonated aromatic polymers with same amount of SO3H, their stability was much higher, but their water swelling and ionic conductivity were quite low. We attributed these differences to strong ionic interactions between the sulfonic acid groups and the basic benzimidazole groups of our polymers. However, we managed to solve this problem synthesizing very highly sulfonated PBI, obtaining membranes with a good balance between all the properties necessary. (author)

  5. Synthesis of Mono-and Di-fluorinated Benzimidazoles

    Institute of Scientific and Technical Information of China (English)

    Liang Wu; Liu Gang

    2011-01-01

    Three efficient methods to synthesize mono-and di-fluofinated benzimidazoles are reported. These methods provide 5-amino-6-fluoro-benzimidazoles (5), 5,7-difluoro-benzimidazoles (10), and 6-fluoro-benzimidazoles (13) starting from commercially available 1,5-difluoro-2,4-dinitrobenzene (DFDNB), 2,3,4,5-tetrafluoro-6-nitrobenzoic acid (TFNBA), and 2,4-difluoro-l-aitrobenzene (DFNB), respectively.

  6. 40 CFR 721.10015 - Halogenated benzimidazole (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Halogenated benzimidazole (generic... Specific Chemical Substances § 721.10015 Halogenated benzimidazole (generic). (a) Chemical substance and... benzimidazole (PMN P-01-110) is subject to reporting under this section for the significant new uses...

  7. Cyclic Benzimidazole Derivatives and Their Antitumor Activity

    Directory of Open Access Journals (Sweden)

    Karminski-Zamola, G.

    2008-06-01

    Full Text Available Over the past years benzimidazole derivatives are one of the most extensively studied classes of heterocyclic compounds, and have received much attention from synthetic organic as well as medicinal chemists, because of their well known biological activities and their applications in several areas as materials in electronics, in electrochemistry as anticorrosive agents, as polymers or optical materials and fluorescent tags in DNA sequencing. The structure of vitamin B12, as an example, contains a benzimidazole group. Compounds containing benzimidazole nuclei show anticancer, antineoplastic, antiinfective, antibacterial, antifungal and many others activities. Due to the structural similarity of benzimidazole nuclei with some naturally occurring compounds such as purine, they can easily interact with biomolecules of the living systems. The introduction of an additional substituent on the benzimidazole nuclei has been increasing attention in the expectation that such changes could potentially affect the interaction of the molecules with biological targets. Fused cyclic benzimidazole derivatives, as benzimidazo[1,2-a]quinolines,benzimidazo[1,2-c]quinazolines, benzimidazo[2,1-b]isoquinolines and many others, have also interesting biological activities and most of them are very good anticancer agents.DNA is the molecular target of many anticancer drugs in clinical use and development. Compounds which can bind to DNA with intercalative or non-intercalative mechanism play a major role in biological processes such as gene transcription or DNA replication. Benzoannulated benzimidazole analogues contain a planar chromophore and have the ability to become inserted between adjacent base pairs of DNA double helix. Intercalators are recognized as one of the most important classes of anticancer agents. So an understanding of the drug-DNA interactions is a promising approach to developing novel reagents and plays a key role in pharmacology today.

  8. Benzimidazole resistance in equine cyathostomins in India.

    Science.gov (United States)

    Kumar, Sunil; Garg, Rajat; Kumar, Saroj; Banerjee, P S; Ram, Hira; Prasad, A

    2016-03-15

    Benzimidazole resistance is a major hindrance to the control of equine cyathostominosis throughout the world. There is a paucity of knowledge on the level of benzimidazole resistance in small strongyles of horses in India. In the present study, allele-specific PCR (AS-PCR) that detects F200Y mutation of the isotype 1 β-tubulin gene and faecal egg count reduction test (FECRT) were used for detecting benzimidazole resistance in equine cyathostomin populations in different agro-climatic zones of Uttar Pradesh, India. Results of the FECRT revealed prevalence of benzimidazole resistance in cyathostomins in an intensively managed equine farm in the mid-western plain (FECR=27.5%, LCI=0) and in working horses (extensively managed) at three locations in central plains of Uttar Pradesh (FECR=75.7-83.6%, LCI=29-57%). Post-treatment larval cultures revealed the presence of exclusively cyathostomin larvae. Genotyping of cyathostomin larvae by AS-PCR revealed that the frequency of homozygous resistant (rr) individuals and the resistant allele frequency was significantly higher (pIndia, necessitates immediate replacement of the drugs of benzimidazole group with other unrelated effective anthelmintics for management and control of equine cyathostomins.

  9. SYNTHESIS AND ANTIFUNGAL ACTIVITY OF SOME SUBSTITUTED BENZIMIDAZOLE ANALOGUES

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    Mehendale Nitin P

    2012-07-01

    Full Text Available In the present scheme, we have an attempt to synthesize some novel benzimidazole derivatives by substituting triazole moiety at N-1 position of benzimidazole by fusion reaction of benzimidazole-1-acetic acid with thiocarbohydrazide. The substituted triazole was refluxed with different aromatic carboxylic acid in the presence of POCl3 yield different benzimidazole derivatives, respectively. The synthesized compounds were characterized by IR, 1H-NMR and Mass spectroscopy. The compounds were screened for antifungal (Candida albicans and Aspergillus niger activities.

  10. ANTIBACTERIAL ACTIVITY OF BENZIMIDAZOLES 2-THIO, 2-AMINODERIVATIVES AND COMPLEXES OF BENZIMIDAZOLES WITH TRANSITIONAL METALS

    Directory of Open Access Journals (Sweden)

    E. I. Mayboroda

    2014-01-01

    Full Text Available The literature data about antibacterial properties of benzimidazole 2-thio-, 2-aminoderivatives and benzimidazole complexes have been generalized and systematized in the review. Today prevention and treatment of diseases caused by microorganisms is an actual problem of modern therapy. Therefore, the search for active molecules, the based on them development of some new, more effective antimicrobial agents is an important task of modern pharmaceutical chemistry. Promising compounds for solving these problems are benzimidazole derivatives. They are available, functionally capable, stable and have a wide spectrum of biological activities (antiviral, anthelmintic, antibacterial, anticancer, antidiabetic.The purpose of this paper is to generalize and systematize information about the antimicrobial action of 2-thio-, 2-amino-substituted benzimidazoles and benzimidazole derivatives complexes with transition metals.These compounds and their complexes with transition metals are active against pathogenic strains Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhimurium, Proteus vulgaris, Bacillus cereus, Micrococcus luteus, Helicobacter рylori and others.

  11. Simple, mild, and highly efficient synthesis of 2-substituted benzimidazoles and bis-benzimidazoles

    Energy Technology Data Exchange (ETDEWEB)

    Eren, Bilge, E-mail: bilge.eren@bilecik.edu.tr [Faculty of Science and Arts, Department of Chemistry, Bilecik Seyh Edebali University, (Turkey); Bekdemir, Yunus [Faculty of Science and Arts, Canik Basari University, Samsun (Turkey)

    2014-07-01

    A new convenient method for preparation of 2-substituted benzimidazoles and bis-benzimidazoles is presented. In this method, o-phenylenediamines were condensed with bisulfite adducts of various aldehydes and di-aldehydes under neat conditions by microwave heating. The results were also compared with results of synthesis by conventional heating under reflux. Structures of the products were confirmed by infrared, {sup 1}H- and {sup 13}C-NMR spectroscopy. Short reaction times, good yields, easy purification of products, and mild reaction conditions are the main advantages of this method. (author)

  12. Derivatives of benzimidazole: vasodilator activity of 2-(p-chloro-alpha-hydroxybenzyl)-benzimidazole hydrochloride. Preliminary study.

    Science.gov (United States)

    Demenge, P; Carraz, G; Luu Duc, C; Silice, C

    1979-01-01

    The effects of 2-(p-chloro-alpha-hydroxybenzyl)-benzimidazole hydrochloride (HBBPC) have been studied in the rabbit and rat. Most of these studies were performed comparatively with reference vasodilators and papaverine. HBBPC vasodilator activity is nearly the same as that of papaverine in the isolated rabbit ear. The characteristic of the vasoactive action of HBBPC seems to reside in its duration. The mechanism of action of HBBPC seems of peripheral type, that is to say it acts on the vascular smooth muscle.

  13. Screening of Trichoderma strains tolerant to benzimidazole

    Institute of Scientific and Technical Information of China (English)

    LIU Kai-qi; XIANG Mei-mei; LIU Ren; ZENG Yong-san; ZHOU Hong-zi; YU Jin-feng; JIANG Xin-yin; ZHANG Yue-li

    2004-01-01

    @@ The screening of isolates and the assay of biocontrol mechanisms of Trichoderma were studied systematically in laboratory and greenhouse in vivo. The proteins tolerant to benzimidazole in Trichoderma strains were purified, and their physical and chemical properties were detected. Compared their biological activities in vitro and vivo in greenhouse, nine biocontrol strains (including Ty- 10-2, LTR-2, Tj-5-1, Tj-5-4, Ty- 11-1, Tj-11-3, Ty- 11-3, Tj-3-3-2, Tj-3-3-4) were screened. These biocontrol strains had faster rates of growth and higher inhibition to gray mould (Bortrytis cinerea),and the inhibition was stable. The effects of controlling gray mould in greenhouse with the screened Trichoderma strains were 70 % and 50 % in vivo.

  14. Detection of benzimidazole carbamates and amino metabolites in liver by surface plasmon resonance-biosensor

    Science.gov (United States)

    Two surface plasmon resonance (SPR) biosensor screening assays were developed and validated to detect 11 benzimidazole carbamate (BZT) and four amino-benzimidazole veterinary drug residues in liver tissue. The assays used polyclonal antibodies, raised in sheep, to detect BZTs and amino-benzimidazole...

  15. [Benzimidazole and its derivatives--from fungicides to designer drugs. A new occupational and environmental hazards].

    Science.gov (United States)

    Lutz, Piotr

    2012-01-01

    Benzimidazole and benzimidazole derivatives play an important role in controlling various fungal pathogens. The benzimidazoles are also used to treat nematode and trematode infections in humans and animals. It acts by binding to the microtubules and stopping hyphal growth. It also binds to the spindle microtubules and blocks nuclear division. The most popular fungicide is carbendazim. The fungicide is used to control plant diseases in cereals and fruits. Laboratory studies have shown that carbendazim cause infertility and destroy the testicles of laboratory animals. Other benzimidazole derivatives are used as a preservative in paint, textile, papermaking, leather industry, and warehousing practices, as well as a preservative of fruits. Occupational exposure to benzimidazole may occur through inhalation and dermal contact with those compounds at workplaces where benzimidazole is used or produced. Some of the benzimidazoles are common environmental pollutants. They are often found in food and fruit products. Some of the benzimidazoles, like a astemizole or esomeprazole have found applications in diverse therapeutical areas. Despite of the clear advantages afforded by the use of benzimidazole derivatives, they share a danger potential. The most hazardous, however, are new illegally synthesed psychoactive drugs known as designer drugs. Some of them, like nitazene, etonitazene or clonitazene belong to benzimidazole derivatives. Laboratory animal studies revealed that etonitazene produced very similar effects in central nervous system as those observed after morphine administration. Considering etonitazene's properties, it seems reasonable to expected that long-term exposure to other benzimidazole derivatives may result in drug abuse and development of drug dependence. PMID:22994080

  16. Growth and properties of benzil doped benzimidazole (BMZ) single crystals

    Energy Technology Data Exchange (ETDEWEB)

    Babu, R. Ramesh, E-mail: rampap2k@yahoo.co.in [Crystal Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli 620 024 (India); Crystal Growth and Crystallography Section, National Physical Laboratory, Krishnan Marg, New Delhi 110 012 (India); Sukumar, M. [Crystal Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli 620 024 (India); Vasudevan, V. [Crystal Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli 620 024 (India); Crystal Growth and Crystallography Section, National Physical Laboratory, Krishnan Marg, New Delhi 110 012 (India); Shakir, Mohd. [Crystal Growth and Crystallography Section, National Physical Laboratory, Krishnan Marg, New Delhi 110 012 (India); Ramamurthi, K. [Crystal Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli 620 024 (India); Bhagavannarayana, G. [Crystal Growth and Crystallography Section, National Physical Laboratory, Krishnan Marg, New Delhi 110 012 (India)

    2010-09-15

    In the present work, we have made an attempt to study the effect of benzil doping on the properties of benzimidazole single crystals. For this purpose we have grown pure and benzil doped benzimidazole single crystals by vertical Bridgman technique. The grown crystals were characterized by various characterization techniques. The presence of dopants confirmed by powder X-ray diffraction (XRD). Crystalline perfection of the grown crystals has been analysed by high-resolution X-ray diffraction (HRXRD). The transmittance, electrical property and mechanical strength have been analysed using UV-vis-NIR spectroscopic, dielectric and Vicker's hardness studies. The relative second harmonic generation efficiency of pure and doped benzimidazole crystals measured using Kurtz powder test.

  17. Benzimidazole resistance in equine cyathostomes in Slovakia.

    Science.gov (United States)

    Várady, M; Königová, A; Corba, J

    2000-12-20

    The present study included 19 stud farms, including 243 horses, that were investigated for the occurrence of anthelmintic resistant cyathostomes. The number of horses on the farms varied from nine to more than 100, and horses of all ages were included. A minimum of seven horses were used for faecal egg count reduction (FECR) tests. The anthelmintics included were: fenbendazole (paste formulation), ivermectin (paste formulation) and pyrantel (powder). Resistance to benzimidazoles was detected on 14 farms, with FECR values ranging from 65.1 to 86.3%. Larval cultures after fenbendazole treatment revealed exclusively cyathostome larvae. Ivermectin was tested on eight farms and proved to be effective on all. Pyrantel was tested on two farms and FECR test indicated high efficacy (92-97%). Egg hatch assay (EHA) results showed that mean concentrations of thiabendazole that inhibited hatching in 50% of the eggs (ED(50)) in resistant populations were over 0.1 microg ml(-1). The results of our study suggest widespread resistance to fenbendazole in equine cyathostomes in Slovakia, and possible strategies to delay anthelmintic resistance are discussed briefly.

  18. Benzimidazole resistance in helminths: From problem to diagnosis.

    Science.gov (United States)

    Furtado, Luis Fernando Viana; de Paiva Bello, Ana Cristina Passos; Rabelo, Élida Mara Leite

    2016-10-01

    Helminth parasites cause significant morbidity and mortality in endemic countries. Given the severity of symptoms that helminths may elicit in the host, intervention with prophylactic and therapeutic measures is imperative. Treatment with benzimidazoles is the most widely used means of combatting these parasites. However, widespread use of these drugs can select for drug-resistant parasite strains. In this review, we approach the problem of benzimidazole resistance in helminths in both humans and animals, focusing on the properties of the drug, the molecular mechanisms of drug resistance and how resistance is diagnosed. PMID:27338184

  19. 2-(3,4-Difluorophenyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    M. S. Krishnamurthy

    2013-11-01

    Full Text Available In the title molecule, C13H8F2N2, the dihedral angle between the benzimidazole ring system and the difluoro-substituted benzene ring is 30.0 (1°. In the crystal, molecules are linked by N—H...N hydrogen bonds, forming chains along [010]. In addition, weak C—H...F hydrogen bonds connect chains into a two-dimensional network parallel to (001. A weak C—H...π interaction is observed between an H atom of the benzimidazole ring sytem and the π system of the difluoro-substituted benzene ring.

  20. 1,4-Bis(1H-benzimidazol-1-ylbenzene

    Directory of Open Access Journals (Sweden)

    Guo-Feng Sun

    2011-09-01

    Full Text Available In the title compound, C20H14N4, the dihedral angles between the central benzene ring and the pendant benzimidazole ring systems are 46.60 (15 and 47.89 (16°. The dihedral angle between the benzimidazole ring systems is 85.62 (12° and the N atoms lie to the same side of the molecule. In the crystal, molecules are linked by C—H...N interactions and weak aromatic π–π stacking [shortest centroid–centroid separation = 3.770 (2 Å] is observed.

  1. Uptake of benzimidazoles by Trichuris suis in vivo in pigs

    DEFF Research Database (Denmark)

    Hansen, Tina Vicky Alstrup; Friis, Christian; Nejsum, Peter;

    2014-01-01

    It is recognized that the clinical efficacy of single dose benzimidazoles (BZs) against the nematode, Trichuris suis of pigs and the closely related Trichuris trichiura in humans is only poor to moderate. Recent in vitro studies have indicated that a low uptake of fenbendazole (FBZ) in T. suis may...

  2. 3-[(1H-Benzimidazol-2-ylsulfanylmethyl]benzonitrile

    Directory of Open Access Journals (Sweden)

    Jin Rui Lin

    2009-06-01

    Full Text Available In the title compound, C15H11N3S, the dihedral angle between the benzimidazole ring system and the benzene ring is 51.8 (2°. The crystal structure exhibits intermolecular N—H...N hydrogen bonds which lead to the formation of C(4 chains along the [001] direction.

  3. Systemic study on fluorescent switching systems composed of naphthopyran and benzimidazole in solution and film forms

    Science.gov (United States)

    He, Yi; Wang, Guang; Wang, Mingxin

    2016-07-01

    The fluorescent photo-switching systems were prepared based on fluorescent benzimidazole and photochromic naphthopyran. Naphthopyran in this systems displayed excellent photochromic performance in tetrahydrofuran solutions and in PMMA films. The fluorescent emission of benzimidazole was modulated between "on" and "off" via the photoisomerization of naphthopyran in high-contrast due to the photoinduced energy transfer from benzimidazole to the open-form naphthopyran. Both the fluorescent photoswitching and the photochromism of benzimidazole-naphthopyran dyads in solutions and films displayed excellent fatigue resistance. The spaces between benzimidazole and naphthopyran affect the absorbance and fluorescence spectra of benzimidazole-naphthopyran dyads. The non-destructive readout ability of synthesized dyads in doped PMMA film was achieved.

  4. Synthesis, Characterization and Biological Evaluation of 1, 2-Disubstituted Benzimidazole Derivatives using Mannich Bases

    OpenAIRE

    Reddy, B. Anil

    2010-01-01

    The ring system in which a benzene ring is fused to the 4,5-positions of imidazole is designated as benzimidazole. Condensations of 2-substituted benzimidazole derivatives were synthesized by different carboxylic acids using Mannich base and anti-inflammatory activity. The various positions on the benzimidazole ring are numbered in the manner indicated with the imino function as number one. The formations of the product were conformed by the analytical and spectral data.

  5. The Target of Benzimidazole Carbamate Against Cysticerci cellulosae

    Institute of Scientific and Technical Information of China (English)

    LI Qing-zhang; HAO Yan-hong; GAO Xue-jun; GAO Wen-xue; ZHAO Bing

    2007-01-01

    To study the target of benzimidazole carbamate drugs against Cysticerci cellulosae and give a theoretical basis for type evolution and new drug design, the changes of key enzyme activities and metabolite contents in the pathway of energy metabolism in C. cellulosae in vitro and in vivo were tested with albendazole and oxfendazole, respectively. Both albendazole and oxfendazole inhibited the pathways of anaerobic glycolysis, partial inversed tricarboxylic acid cycle of Taenia Solium oncosphere, immature and mature Cysticerci in vitro, and immature and mature Cysticerci in vivo to a certain degree, and enhanced fat decomposing, amino acid decomposing, xanthine decomposing metabolism, and on the other hand, the absorption of glucose was hindered; furthermore, both albendazole and oxfendazole inhibited the activities of the fumaric reductase (FR) complex noncompetently in vitro. Benzimidazole carbamate drugs could inhibit the activities of FR complex noncompetently and hinder the absorption of glucose.

  6. Benzimidazole grafted polybenzimidazoles for proton exchange membrane fuel cells

    DEFF Research Database (Denmark)

    Yang, Jingshuai; Aili, David; Li, Qingfeng;

    2013-01-01

    High molecular weight polybenzimidazole (PBI) was synthesized and grafted with benzimidazole pendant groups. The high molecular weight of PBI resulted in good film-forming properties and superior tensile strength. With a phosphoric acid doping level (ADL) of 13.1, a tensile strength of 16 MPa...... was achieved at room temperature. Grafting of benzimidazole moieties onto the PBI macromolecular chain introduced additional basic sites which allowed the membrane to achieve higher phosphoric acid uptakes. A molar acid conductivity, defined as the specific conductivity of each mole of doping acid......, was proposed to evaluate the effective conductivity contributed from the doping acids. With a grafting degree of 5.3% and an ADL of 13.1, the PBI membranes exhibited a total conductivity of 0.15 S cm-1. A H2-air fuel cell based on this membrane showed a peak power density of 378 mW cm-2 at 180 °C without...

  7. Synthesis and crystal structure of ethyl benzimidazole-2-yl phosphonate

    Institute of Scientific and Technical Information of China (English)

    HU, Fang-Zhong; WENG, Lin-Hong; YANG, Hua-Zheng; ZOU, Xiao-Mao

    2000-01-01

    When N-cyanoimido- ( O, O-diethyl ) phosphonyl/ S-methyl thiocarbonate (1) was treated with o-phenylenediamine in the presence of Et3N in ethanol, diethyl benzimidazole-2-yl recrys phonate(2) was obtained and hydrolyzed during the recrys tallization in MeOH/H2O, generating ethyl benzimidazole-2-yl phosphonate(3). The crystal structure of compound 3 was determined by X-ray diffraction method. The crystals belong to monoclinic, space rgoup C2/c, a=1.78408(18), b=O. 83725(9), c=1.67401(18) nm, β= 118.997(2)°, v=2. 1870(4) nm3, z=8, Dc=1.374g/cm3, F(000)=944.The final R and wR are 0.0499 and 0.1436, respectively. The mechanism of the above reaction is also discussed.

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

    OpenAIRE

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

    1981-01-01

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

  9. 1-(1-Benzyl-1H-benzimidazol-2-ylethanone

    Directory of Open Access Journals (Sweden)

    Chuan-Jing Zhang

    2012-12-01

    Full Text Available In the title compound, C16H14N2O, the benzimidazole ring system is essentially planar. The planes of the benzene rings make a dihedral angle of 85.92 (8°. In the crystal, neighbouring molecule are connected into paris along the c axis by weak C—H...O interactions and the connected pairs are expanded through C—H...N hydrogen bonds and C—H...π interactions along the b axis.

  10. 1,3,5-Trimethylpyrazolium chloride based ionogel as an efficient and reusable heterogeneous catalyst for the synthesis of benzimidazoles

    Indian Academy of Sciences (India)

    Pankaj Sharma; Monika Gupta

    2016-01-01

    A new approach for the synthesis of benzimidazoles using ionogel under solvent-free conditions is reported. Catalytic activity of ionogel was compared with silica coated with ionic liquid (silica-IL) and it was found that ionogel is highly active compared to silica-IL for the synthesis of benzimidazoles. Moreover, ionogel was recyclable for the synthesis of benzimidazoles.

  11. Copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles from imidoyl chlorides

    Institute of Scientific and Technical Information of China (English)

    Hui Yu; Mei Shu Zhang; Li Ren Cui

    2012-01-01

    A strategy for the synthesis of 1,2-disubstituted benzimidazoles has been developed and a variety of 1,2-disubstituted benzimidazoles were obtained from imidoyl chlorides and o-haloanilines via copper(I)-catalyzed reaction in moderate yields.

  12. Ionic conducting poly-benzimidazoles; Polybenzimidazoles conducteurs ioniques

    Energy Technology Data Exchange (ETDEWEB)

    Jouanneau, J

    2006-11-15

    Over the last years, many research works have been focused on new clean energy systems. Hydrogen fuel cell seems to be the most promising one. However, the large scale development of this technology is still limited by some key elements. One of them is the polymer electrolyte membrane 'Nafion' currently used, for which the ratio performance/cost is too low. The investigations we carried out during this thesis work are related to a new class of ionic conducting polymer, the sulfonated poly-benzimidazoles (sPBI). Poly-benzimidazoles (PBI) are aromatic heterocyclic polymers well-known for their excellent thermal and chemical stability. Ionic conduction properties are obtained by having strong acid groups (sulfonic acid SO{sub 3}H) on the macromolecular structure. For that purpose, we first synthesized sulfonated monomers. Their poly-condensation with an appropriate non-sulfonated co-monomer yields to sPBI with sulfonation range from 0 to 100 per cent. Three different sPBI structures were obtained, and verified by appropriate analytical techniques. We also showed that the protocol used for the synthesis resulted in high molecular weights polymers. We prepared ionic conducting membrane by casting sPBI solutions on glass plates. Their properties of stability, water swelling and ionic conductivity were investigated. Surprisingly, the behaviour of sPBI was quite different from the other sulfonated aromatic polymers with same amount of SO{sub 3}H, their stability was much higher, but their water swelling and ionic conductivity were quite low. We attributed these differences to strong ionic interactions between the sulfonic acid groups and the basic benzimidazole groups of our polymers. However, we managed to solve this problem synthesizing very highly sulfonated PBI, obtaining membranes with a good balance between all the properties necessary. (author)

  13. 2-(1H-Benzimidazol-2-yl-4-nitrophenol

    Directory of Open Access Journals (Sweden)

    Jingya Sun

    2011-02-01

    Full Text Available The title compound, C13H9N3O3, was prepared by the reaction of 5-nitrosalicylaldehyde with 1,2-diaminobenzene in methanol. The whole molecule is approximately planar, with a mean deviation from the plane defined by the non-H atoms of 0.0311 (4 Å, and with a dihedral angle between the benzene ring and the benzimidazole ring system of 1.1 (3°. An intramolecular O—H...N hydrogen bond occurs. In the crystal, adjacent molecules are linked through intermolecular N—H...O hydrogen bonds, forming centrosymmetric dimers.

  14. 1-(2,6-Diisopropylphenyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Hongwei Wu

    2013-08-01

    Full Text Available In the title compound, C19H22N2, both the benzimidazole unit and the 2,6-diisopropylphenyl group are essentially planar [maximum deviations from the least-squares planes of 0.005 (1 and 0.009 (1 Å, respectively]. The dihedral angle between the two planes is 79.6 (7°. In the crystal, molecules are linked into chains along the a-axis direction by weak C—H...N interactions. The crystal structure also features C—H...π interactions, which link the chains into a three-dimensional network.

  15. Synthesis and trypanocidal activity of novel benzimidazole derivatives.

    Science.gov (United States)

    Velázquez-López, José Miguel; Hernández-Campos, Alicia; Yépez-Mulia, Lilián; Téllez-Valencia, Alfredo; Flores-Carrillo, Paulina; Nieto-Meneses, Rocío; Castillo, Rafael

    2016-09-01

    The present work reports the synthesis and biological activity of a series of 14 benzimidazole derivatives designed to act on the enzyme triosephosphate isomerase of Trypanosoma cruzi (TcTIM). This enzyme is involved in the metabolism of glucose, the only source of energy for the parasite. In this study, we found four compounds that inhibit TcTIM moderately and lack inhibitory activity against human TIM (HsTIM). In vitro studies against T. cruzi epimastigotes showed two compounds that were more active than the reference drug nifurtimox, and these presented a low cytotoxic effect in mouse macrophages (J744 cell line). PMID:27503677

  16. Benzimidazole as corrosion inhibitor for heat treated 6061 Al- SiCp composite in acetic acid

    Science.gov (United States)

    Chacko, Melby; Nayak, Jagannath

    2015-06-01

    6061 Al-SiCpcomposite was solutionizedat 350 °C for 30 minutes and water quenched. It was then underaged at 140 °C (T6 treatment). The aging behaviour of the composite was studied using Rockwell B hardness measurement. Corrosion behaviour of the underaged sample was studied in different concentrations of acetic acid and at different temperatures. Benzimidazole at different concentrations was used for the inhibition studies. Inhibition efficiency of benzimidazole was calculated for different experimental conditions. Thermodynamic parameters were found out which suggested benzimidazole is an efficient inhibitor and it adsorbed on to the surface of composite by mixed adsorption where chemisorption is predominant.

  17. Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives

    OpenAIRE

    Gaballah, Samir T.; El-Nezhawy, Ahmed O. H.; Amer, Hassan; Ali, Mamdouh Moawad; Mahmoud, Abeer Essam El-Din; Hofinger-Horvath, Andreas

    2015-01-01

    The design, synthesis, and in vitro antiproliferative activity of a novel series of sulfide (4a–i) and sulfoxide (5a–h) derivatives of benzimidazole, in which different aromatic and heteroaromatic acetamides are linked to benzimidazole via sulfide (4a–i) and sulfoxide (5a–h) linker, are reported and the structure-activity relationship is discussed. The new derivatives were prepared by coupling 2-(mercaptomethyl)benzimidazole with 2-bromo-N-(substituted) acetamides in dry acetone in the presen...

  18. Synthesis, spectral correlation and insect antifeedant activities of some 2-benzimidazole chalcones

    Directory of Open Access Journals (Sweden)

    P. Janaki

    2016-01-01

    Full Text Available Some substituted styryl 2-benzimidazole ketones have been synthesised by fly-ash:H2SO4 catalysed aldol condensation of 2-benzimidazole methyl ketone and various substituted benzaldehydes in microwave oven. The yields of these chalcones are more than 70%. The purities of synthesised benzimidazole chalcones were checked by their physical constants and spectral data earlier published in the literature. The spectral frequencies of these chalcones have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses the effects of substituent on the group frequencies were discussed. The insect antifeedant activities of these chalcones have been studied using Dethler’s method.

  19. 1-[2,2-Bis(1,3-benzimidazol-1-ylmethyl-3-bromopropyl]-1,3-benzimidazole

    Directory of Open Access Journals (Sweden)

    Tai-Bao Wei

    2011-07-01

    Full Text Available The title compound, C26H23BrN6, has been synthesized as a potential ligand for the construction of metal–organic frameworks. The three benzimidazolyl groups present three potential coordination nodes. The dihedral angles between the benzimidazole ring systems are 74.03 (10, 66.49 (9 and 74.09 (9°. The structure contains large voids, which contain highly disordered solvent molecules that may be CH3CH2OH. Since the solvent molecules could not be located, the PLATON/SQUEEZE procedure [Spek (2009. Acta Cryst. D65, 148–155] was used.

  20. Synthesis and Characterization of Poly (Arylene Ether Benzimidazole) Oligomers

    Science.gov (United States)

    Leonard, Michael J.

    1995-01-01

    Several poly(arylene ether benzimidazole) oligomers were prepared by the nucleophilic aromatic substitution reaction of a bisphenol benzimidazole and various alkyl-substituted aromatic bisphenols with an activated aromatic dihalide in N, N-dimethylacetarnide. Moderate to high molecular weight terpolymers were obtained in all cases, as shown by their inherent viscosities, which ranged from 0.50 to 0.87 dL g(sup -1). Glass transition temperatures (T(sub g)s) of polymer powders ranged from 267-280 C. Air-dried unoriented thin film T(sub g)s were markedly lower than those of the powders, whereas T(sub g)s of films dried in a nitrogen atmosphere were identical to those of the corresponding powders. In addition, air-dried films were dark amber and brittle, whereas nitrogen-dried films were yellow and creasable. Nitrogen-dried films showed slightly higher thin-film tensile properties than the air-dried films, as well.

  1. Syntheses of Binuclear Copper(Ⅰ)Complexes Containing Benzimidazole

    Institute of Scientific and Technical Information of China (English)

    LIU Ying-Fan; ZHAO Dong; GUO Li-Bing; ZHENG Xin; SUN Yu-An

    2005-01-01

    A binuclear copper(Ⅰ) complex [Cu2(dppm)2(C7H6N2)2](NO3)2 (C7H6N2 = benzimidazole, dppm = Ph2PCH2PPh2) has been synthesized and characterized by X-ray crystallography.The crystal belongs to monoclinic, space group C2/c with a = 14.167(3), b = 21.209(4), c =20.680(4) A, β = 103.93(3)°, C32H28CuN3O3P2, Mr = 628.05, Z = 8,μ = 0.868 mm-1, V = 6031 (2)(。A)3,F(000) = 2592, Dc= 1.383 g/cm3, R = 0.0593 and wR = 0.1736.A total of 5297 independent reflec tions were collected, of which 3503 were observed with I > 2σ(I).The central copper atom is tri-coordinated by phosphorus atoms from bridging dppm and nitrogen atom from benzimidazole.In the coordination sphere, the bond lengths of Cu-P(1) and Cu-P(2) are 2.2607(17) and 2.2503(16)(。A),respectively and the P-Cu-P bond angle is 127.26(6)°.

  2. Benzimidazole resistance in Haemonchus contortus recovered from farmed red deer.

    Science.gov (United States)

    Nagy, Gábor; Csivincsik, Ágnes; Zsolnai, Attila; Sugár, László

    2016-09-01

    Thirty Haemonchus contortus male worms were collected from farmed red deer yearlings in order to determine whether routine administration of albendazole for a long-term period (17 years) could select anthelmintic resistance. PCR-RFLP method based on single-nucleotide polymorphism of codon 200 in isotype 1 ß-tubulin gene (Phe200Tyr) was applied. The results showed a significant frequency of either the resistant allele (85 %) or the homozygous resistant genotype (70 %). By chi-square test, Hardy-Weinberg equilibrium of the population was accepted (p = 0.334, power of test 0.01). True prevalence of the resistant genotype (RR) was estimated to be 46.5-87.2 % (confidence interval 95 %) calculated by Sterne's exact method. These results confirmed that long-term use of benzimidazoles could change the relative allele frequency of genes associated with drug resistance and may cause a large-scale spread of the resistant allele. To our knowledge, this study supported benzimidazole resistance in Haemonchus contortus in red deer for the first time. PMID:27249966

  3. Metabolic pathways of benzimidazole anthelmintics in harebell (Campanula rotundifolia).

    Science.gov (United States)

    Stuchlíková, Lucie; Jirásko, Robert; Skálová, Lenka; Pavlík, František; Szotáková, Barbora; Holčapek, Michal; Vaněk, Tomáš; Podlipná, Radka

    2016-08-01

    Benzimidazoles anthelmintics, which enter into environment primarily through excretion in the feces or urine of treated animals, can affect various organisms and disrupt ecosystem balance. The present study was designed to test the phytotoxicity and biotransformation of the three benzimidazole anthelmintics albendazole (ABZ), fenbendazole (FBZ) and flubendazole (FLU) in the harebell (Campanula rotundifolia). This meadow plant commonly grows in pastures and comes into contact with anthelmintics through the excrements of treated animals. Suspensions of harebell cells in culture medium were used as an in vitro model system. ABZ, FLU and FBZ were not found to be toxic for harebell cells, which were able to metabolize ABZ, FLU and FBZ via the formation of a wide scale of metabolites. Ultrahigh-performance liquid chromatography coupled with high mass accuracy tandem mass spectrometry (UHPLC-MS/MS) led to the identification of 24, 18 and 29 metabolites of ABZ, FLU and FBZ, respectively. Several novel metabolites were identified for the first time. Based on the obtained results, the schemes of the metabolic pathways of these anthelmintics were proposed. Most of these metabolites can be considered deactivation products, but a substantial portion of them may readily be decomposed to biologically active substances which could negatively affect ecosystems. PMID:27208642

  4. Benzimidazole Derivatives as Potent JAK1-Selective Inhibitors.

    Science.gov (United States)

    Kim, Mi Kyoung; Shin, Heerim; Park, Kwang-su; Kim, Hyungmi; Park, Jiseon; Kim, Kangjeon; Nam, Joonwoo; Choo, Hyunah; Chong, Youhoon

    2015-09-24

    The Janus kinase (JAK) family comprises four members (JAK1, JAK2, JAK3, and Tyk2) that play a key role in mediating cytokine receptor signaling. JAK inhibition thus modulates cytokine-mediated effects. In particular, selective inhibition of JAK1 or JAK3 may provide an efficient therapeutic agent for the treatment of inflammatory diseases, with minimized side effects. In this study, as part of our continued efforts to develop a selective JAK1 inhibitor, a series of 1,2-disubstituted benzimidazole-5-carboxamide derivatives was prepared and their inhibitory activities against all four JAK isozymes were evaluated. A clear structure-activity relationship was observed with respect to JAK1 selectivity; this highlighted the importance of hydrogen bond donors at both N(1) and R2 positions located within a specific distance from the benzimidazole core. One of the synthesized compounds, 1-(2-aminoethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide (5c), showed remarkable JAK1 selectivity (63-fold vs JAK2, 25-fold vs JAK3, and 74-fold vs Tyk2). Molecular docking revealed that the 2-aminoethyl and piperidin-4-yl substituents of 5c function as probes to differentiate the ATP-binding site of JAK1 from that of JAK2, resulting in preferential JAK1 binding. A kinase panel assay confirmed the JAK1 selectivity of 5c, which showed no appreciable inhibitory activity against 26 other protein kinases at 10 μM. PMID:26351728

  5. Molecular mechanism of resistance of Fusarium fujikuroi to benzimidazole fungicides.

    Science.gov (United States)

    Chen, Zihao; Gao, Tao; Liang, Shuping; Liu, Kexue; Zhou, Mingguo; Chen, Changjun

    2014-08-01

    Although carbendazim (MBC) and other benzimidazole fungicides have effectively controlled bakanae disease of rice (which is caused by Fusarium fujikuroi, F. proliferatum, and F. verticillioides) in the past, MBC resistance has become common. Previous research has shown that MBC resistance results from a mutation in the β1 -tubulin (β1 tub) gene in F. verticillioides. However, MBC resistance in F. fujikuroi, a predominant species in China, does not result from a mutation in the β1 tub. The molecular mechanism of F. fujikuroi resistance against benzimidazole fungicides is poorly understood. In this study, we determined that although β1 tub and β2 -tubulin (β2 tub) in F. fujikuroi have high homology with β1 tub and β2 tub in F. verticillioides, MBC resistance in F. fujikuroi results from mutations in β2 tub [GAG(Glu)→GTG(Val) at codon 198, TTC(Phe)→TAC(Tyr) at codon 200, and GGC(Gly)→GGT(Gly) at codon 235] but not in β1 tub. Δβ2 tub (β2 tub deletion) mutants were highly sensitive to MBC, produced fewer conidia and were less virulent than parental strains. Complementation of the Δβ2 tub mutants with a copy of the whole β2 tub locus from their parental strains restored the level of MBC resistance (or sensitivity) to that of the parental strain.

  6. 2-Methyl-6-(6-methyl-1H-benzimidazol-2-ylphenol–2-methyl-6-(5-methyl-1H-benzimidazol-2-ylphenol (3/1

    Directory of Open Access Journals (Sweden)

    Suchada Chantrapromma

    2009-12-01

    Full Text Available The title compound, 0.75C15H14N2O·0.25C15H14N2O, is a co-crystal of 2-methyl-6-(6-methyl-1H-benzimidazol-2-ylphenol as the major component and 2-methyl-6-(5-methyl-1H-benzimidazol-2-ylphenol as the minor component. The refined site-occupancy ratio is 0.746 (4/0.254 (4. The conformations of both components are identical except for that of the methyl substituent on the benzene ring of the benzimidazole unit which is positionally disordered over two positions. The molecule is essentially planar, the dihedral angle between the benzimidazole plane and the benzene ring being 3.49 (4°. An intramolecular O—H...N hydrogen bond generates an S(6 ring motif. In the crystal packing, molecules are linked through N—H...O hydrogen bonds into chains along [201]. These chains are stacked approximately along the a-axis direction. The crystal packing is further stabilized by weak N—H...O and O...H...N hydrogen bonds, together with weak intermolecular C—H...π interactions. A π–π interaction with a centroid–centroid distance of 3.6241 (6 Å is also observed between the substituted phenyl ring and that of the benzimidazole system.

  7. BF3·OEt2 Promoted Solvent-free Synthesis of Benzimidazole Derivatives

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    Differently substituted benzimidazoles have been synthesized in very good yields in catalyst. The method is applicable to aromatic, unsaturated and aliphatic aldehydes and to substituted o-phenylenediamines without significant differences.

  8. Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine.

    Science.gov (United States)

    Ajani, Olayinka O; Aderohunmu, Damilola V; Ikpo, Chinwe O; Adedapo, Adebusayo E; Olanrewaju, Ifedolapo O

    2016-07-01

    Benzimidazole derivatives are crucial structural scaffolds found in diverse libraries of biologically active compounds which are therapeutically useful agents in drug discovery and medicinal research. They are structural isosteres of naturally occurring nucleotides, which allows them to interact with the biopolymers of living systems. Hence, there is a need to couple the latest information with the earlier documentations to understand the current status of the benzimidazole nucleus in medicinal chemistry research. This present work unveils the benzimidazole core as a multifunctional nucleus that serves as a resourceful tool of information for synthetic modifications of old existing candidates in order to tackle drug resistance bottlenecks in therapeutic medicine. This manuscript deals with the recent advances in the synthesis of benzimidazole derivatives, the widespread biological activities as well as pharmacokinetic reports. These present them as a toolbox for fighting infectious diseases and also make them excellent candidates for future drug design. PMID:27213292

  9. Transport of anthelmintic benzimidazole drugs by breast cancer resistance protein (BCRP/ABCG2)

    NARCIS (Netherlands)

    Merino, G; Jonker, JW; Wagenaar, E; Pulido, MM; Molina, AJ; Alvarez, AI; Schinkel, AH

    2005-01-01

    Methylcarbamate benzimidazoles [albendazole (ABZ), fenbendazole (FBZ), and their respective sulfoxide derivatives, albendazole sulfoxide (ABZSO) and oxfendazole (OXF)] are therapeutically important anthelmintic agents with low bioavailability. We studied their in vitro interaction with the apical AT

  10. Antidiabetic effect of 2 nitro benzimidazole in alloxan induced diabetic rats

    Directory of Open Access Journals (Sweden)

    Prapthi Bathini

    2013-12-01

    Conclusion: 2 nitro benzimidazole exhibited significant antihyperglycemic activity in alloxan-induced diabetic rats comparable to that of the standard drug glibenclamide. [Int J Basic Clin Pharmacol 2013; 2(6.000: 814-818

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

    Institute of Scientific and Technical Information of China (English)

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

    2011-01-01

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

  12. 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.

  13. Synthesis and in Vitro Antiproliferative Evaluation of Some B-norcholesteryl Benzimidazole and Benzothiazole Derivatives

    OpenAIRE

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

    2015-01-01

    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 benzothiazol...

  14. Polyethylene glycol: A recyclable solvent system for the synthesis of benzimidazole derivatives using CAN as catalyst

    Indian Academy of Sciences (India)

    Mazaahir Kidwai; Anwar Jahan; Divya Bhatnagar

    2010-07-01

    Ceric ammonium nitrate (CAN) efficiently catalysed the synthesis of benzimidazole derivatives from -phenylenediamine and aldehydes in PEG. This method provides a novel route for the synthesis of benzimidazoles in good yields with little catalyst loading. The recovery and the successful reutilization of the solvent system are also presented. Moreover, the easy set-up and purification tasks of this sustainable method make it appealing for bulk industry applications.

  15. Crystal structure of a complex of human chymase with its benzimidazole derived inhibitor

    Energy Technology Data Exchange (ETDEWEB)

    Matsumoto, Yoshiyuki; Kakuda, Shinji; Koizumi, Masahiro; Mizuno, Tsuyoshi; Muroga, Yumiko; Kawamura, Takashi; Takimoto-Kamimura, Midori, E-mail: m.kamimura@teijin.co.jp [Teijin Institute for Bio-medical Research, 4-3-2 Asahigaoka, Hino, Tokyo 191-8512 (Japan)

    2013-11-01

    The crystal structure of human chymase complexed with a novel benzimidazole inhibitor, TJK002, was determined at 2.8 Å resolution. The present study shows that the benzimidazole ring of the inhibitor takes the stable stacking interaction with the protonated His57 in the catalytic domain of human chymase. The crystal structure of human chymase complexed with a novel benzimidazole inhibitor, TJK002, was determined at 2.8 Å resolution. The X-ray crystallographic study shows that the benzimidazole inhibitor forms a non-covalent interaction with the catalytic domain of human chymase. The hydrophobic fragment of the inhibitor occupies the S1 pocket. The carboxylic acid group of the inhibitor forms hydrogen bonds with the imidazole N(∊) atom of His57 and/or the O(γ) atom of Ser195 which are members of the catalytic triad. This imidazole ring of His57 induces π–π stacking to the benzene ring of the benzimidazole scaffold as P2 moiety. Fragment molecular orbital calculation of the atomic coordinates by X-ray crystallography shows that this imidazole ring of His57 could be protonated with the carboxyl group of Asp102 or hydroxyl group of Ser195 and the stacking interaction is stabilized. A new drug design strategy is proposed where the stacking to the protonated imidazole of the drug target protein with the benzimidazole scaffold inhibitor causes unpredicted potent inhibitory activity for some enzymes.

  16. Antituberculosis: Synthesis and Antimycobacterial Activity of Novel Benzimidazole Derivatives

    Directory of Open Access Journals (Sweden)

    Yeong Keng Yoon

    2013-01-01

    Full Text Available A total of seven novel benzimidazoles were synthesized by a 4-step reaction starting from 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The synthesized compounds were screened for their antimycobacterial activity against M. tuberculosis H37Rv (MTB-H37Rv and INH-resistant M. tuberculosis (INHR-MTB strains using agar dilution method. Three of them displayed good activity with MIC of less than 0.2 μM. Compound ethyl 1-(2-(4-(4-(ethoxycarbonyl-2-aminophenylpiperazin-1-ylethyl-2-(4-(5-(4-fluorophenylpyridin-3-ylphenyl-1H-benzo[d]imidazole-5-carboxylate (5g was found to be the most active with MIC of 0.112 μM against MTB-H37Rv and 6.12 μM against INHR-MTB, respectively.

  17. Spectrophotometric Determination of Certain Benzimidazole Proton Pump Inhibitors

    Science.gov (United States)

    Syed, A. A.; Syeda, Ayesha

    2008-01-01

    Spectrophotometric method for the determination of certain proton pump inhibitors belonging to the benzimidazole class of compounds has been developed. The method is based on the reaction of omeprazole, lansoprazole, pantoprazole, rabeprazole and esomeprazole with iron (III) and subsequent reaction with ferricyanide under neutral condition which yields Prussian blue product with maximum absorption at 720–730 nm. The commonly encountered excipients and additives that often accompany pharmaceutical preparations did not interfere with the determination. The method was applied for the determination of omeprazole, lansoprazole, pantoprazole, rabeprazole and esomeprazole in pharmaceutical preparations and no difference was found statistically. Thus, the spectrophotometric method can be applied as inexpensive, rapid, easy, accurate and precise method for the routine analysis of the five proton pump inhibitors in pharmaceutical preparations. PMID:20046782

  18. Novel JAK1-selective benzimidazole inhibitors with enhanced membrane permeability.

    Science.gov (United States)

    Kim, Hyungmi; Kim, Mi Kyoung; Choo, Hyunah; Chong, Youhoon

    2016-07-15

    The previously identified Janus kinase 1 (JAK1)-selective inhibitor, 1-(2-aminoethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide (2), suffered from low cell permeability, which resulted in poor pharmacokinetic properties. In this study, by introducing less polar hydrogen bond donors at N(1) (a hydroxyalkyl or a methylaminoalkyl group) and C2 (a cyclohexanol group) positions, a series of novel benzimidazole derivatives were prepared, which exhibited selective JAK1 inhibitory activity (IC50 against JAK1=0.08-0.15μM; JAK1-selectivity=26-40 fold vs JAK2, 12-23 fold vs JAK3, and 38-54 fold vs Tyk2) along with significantly increased lipophilicity (3.3-15.8 times) as well as membrane permeability (6.3-12 times). PMID:27261178

  19. Benzimidazole based ratiometric and colourimetric chemosensor for Ni(II)

    Science.gov (United States)

    Sarkar, Deblina; Pramanik, Ajoy Kumar; Mondal, Tapan Kumar

    2016-01-01

    A highly sensitive and selective benzimidazole based colourimetric chemosensor (HL) for the efficient detection of Ni2 + has been reported. The synthesized chemosensor HL is highly efficient in detecting Ni2 + over other metal ions that commonly coexist with Ni2 + in physiological and environmental samples. HL also shows distinct color change from orange yellow to blue visible under the naked eye due to specific binding with Ni2 +. This color change corresponds to a large red shift of the UV-Vis spectrum from 403 nm to 600 nm with a distinct isosbestic point at around 500 nm. The cation sensing property of the receptor HL has been examined by UV-Vis spectroscopy. Electronic structure of the HL-Ni2 + complex and sensing mechanism has been interpreted by DFT and TDDFT calculations.

  20. 1-Phenyl-2-[4-(trifluoromethylphenyl]-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    K. Jayamoorthy

    2013-02-01

    Full Text Available In the title molecule, C20H13F3N2, the benzimidazole unit is close to being planar [maximum deviation = 0.012 (1 Å] and forms dihedral angles of 31.43 (7 and 61.45 (9° with the 4-(trifluoromethylphenyl and 1-phenyl rings, respectively; the dihedral angle between these rings is 60.94 (10°. In the crystal, C—H...F hydrogen bonds link the molecules into chains along the c-axis direction. The CF3 group is rotationally disordered with an occupancy ratio of 0.557 (8:0.443 (8 for the F atoms.

  1. 5-Amino-1-methyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Jan Lokaj

    2009-08-01

    Full Text Available The structure of the title compound, C8H9N3, a potential antitumour drug, was determined in order to give more insight into its structure–function relationships. The benzimidazole core of the molecule was found to be exactly planar, while the substituents are displaced slightly from the molecular plane [C—C—N—C and C—C—C—N torsion angles of 0.8 (3 and 179.0 (1° for the methyl and amino groups, respectively]. The bond lengths are analysed in detail and compared with those of the parent unsubstituted analogues. The results show that the lone-pair electrons on the amino N atom are involved in conjugation with the adjacent π system and hence affect the charge distribution in the heterocycle. Two intermolecular N—H...N and C—H...N hydrogen bonds have been identified.

  2. Spectrophotometric determination of certain benzimidazole proton pump inhibitors

    Directory of Open Access Journals (Sweden)

    Syed A

    2008-01-01

    Full Text Available Spectrophotometric method for the determination of certain proton pump inhibitors belonging to the benzimidazole class of compounds has been developed. The method is based on the reaction of omeprazole, lansoprazole, pantoprazole, rabeprazole and esomeprazole with iron (III and subsequent reaction with ferricyanide under neutral condition which yields Prussian blue product with maximum absorption at 720-730 nm. The commonly encountered excipients and additives that often accompany pharmaceutical preparations did not interfere with the determination. The method was applied for the determination of omeprazole, lansoprazole, pantoprazole, rabeprazole and esomeprazole in pharmaceutical preparations and no difference was found statistically. Thus, the spectrophotometric method can be applied as inexpensive, rapid, easy, accurate and precise method for the routine analysis of the five proton pump inhibitors in pharmaceutical preparations.

  3. 2-(1-Phenyl-1H-benzimidazol-2-ylphenol

    Directory of Open Access Journals (Sweden)

    Sema Öztürk Yildirim

    2013-01-01

    Full Text Available In the title molecule, C19H14N2O, the benzimidazole unit is close to being planar [maximum deviation = 0.0253 (11 Å] and forms dihedral angles of 68.98 (6 and 20.38 (7° with the adjacent phenyl and benzene rings; the dihedral angle between the latter two planes is 64.30 (7°. An intramolecular O—H...N hydrogen bond generates an S(6 ring motif. In the crystal, molecules are linked by C—H...N and C—H...O hydrogen bonds, and consolidated into a three-dimensional architecture by π–π stacking interactions, with a centroid–centroid distance of 3.8428 (12 Å.

  4. Nanostructured poly(benzimidazole membranes by N-alkylation

    Directory of Open Access Journals (Sweden)

    J. Weber

    2014-01-01

    Full Text Available Modification of poly(benzimidazole (PBI by N-alkylation leads to polymers capable of undergoing microphase separation. Polymers with different amounts of C18 alkyl chains have been prepared. The polymers were analyzed by spectroscopy, thermal analysis, electron microscopy and X-ray scattering. The impact of the amount of alkyl chains on the observed microphase separation was analyzed. Membranes prepared from the polymers do show microphase separation, as evidenced by scattering experiments. While no clear morphology could be derived for the domains in the native state, evidence for the formation of lamellar morphologies upon doping with phosphoric acid is provided. Finally, the proton conductivity of alkyl-modified PBI is compared with that of pure PBI, showing that the introduction of alkyl side chains does not result in significant conductivity changes.

  5. QSAR MODELING OF ANTIBACTERIAL ACTIVITY OF SOME BENZIMIDAZOLE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    SANJA O. PODUNAVAC-KUZMANOVIĆ

    2011-03-01

    Full Text Available A quantitative structure-activity relationship (QSAR study has been carried out for a training set of 12 benzimidazole derivatives to correlate and predict the antibacterial activity of studied compounds against Gram-negative bacteria Pseudomonas aeruginosa. Multiple linear regression was used to select the descriptors and to generate the best prediction model that relates the structural features to inhibitory activity. The predictivity of the model was estimated by cross-validation with the leave-one-out method. Our results suggest a QSAR model based on the following descriptors: parameter of lipophilicity (logP and hydration energy (HE. Good agreement between experimental and predicted inhibitory values, obtained in the validation procedure, indicated the good quality of the generated QSAR model.

  6. Anion directed supramolecular architecture of benzimidazole-based receptor

    Science.gov (United States)

    Singh, Udai P.; Maurya, Radha Raman; Kashyap, Sujata

    2015-02-01

    The reaction of N,N,N‧,N‧-tetrakis-(1H,benzimidazol-2ylmethyl)ethane-1,2-diamine (L) with different inorganic as well as organic acid afford salts viz., LH44+·4ClO4-·4H2O (1), LH44+·4Br-·4(CH3)2SO (2), 2LH33+·3SiF62-·14H2O (3), LH44+·4H2PO4-·2H3PO4 (4) and L·2CH3COOH (5) with different structures. The X-ray crystallographic studies revealed that these compounds are all ionic in nature due to proton transfer except 5 and are stabilized in the solid state by networks of hydrogen bonds between their respective components as well as solvent molecules. It also demonstrates that different types of hydrogen bond between protonated ligand and the anions are responsible for the extensive supramolecular frame work. The three dimensional packing is mainly guided by well-balanced primary N-H⋯O, O-H⋯N, O-H⋯O hydrogen bonds and secondary C-H⋯O interactions between benzimidazole and acids. Moreover, the hydrogen bonds, π⋯π and C-H⋯π stacking interactions appear to be effective in stabilizing the crystal structures. The colorimetric test showed color change upon the addition of acids in solution of the ligand. The photo-physical experiments suggest that the ligand shows fluorescence properties in the presence of acids.

  7. A rapid diagnostic tool for detecting benzimidazole resistance in Cercospora beticola, the causal agent of Cercospora leaf spot in sugarbeet

    Science.gov (United States)

    Resistance in Cercospora beticola to benzimidazole fungicides was selected in many sugar beet regions of the world due to extensive use of this fungicide class. Practical resistance to benzimidazole in populations of C. beticola was first reported in Greece in 1973. Resistance has subsequently been ...

  8. Benzimidazole Carbamate Residues in Milk: Detection by SPR Biosensor; using a Modified QuEChERS Method for Extraction

    Science.gov (United States)

    A surface plasmon resonance (SPR) biosensor screening assay was developed and validated to detect 11 benzimidazole carbamate (BZT) veterinary drug residues in milk. The polyclonal antibody used was raised in sheep against a methyl 5 (6)-[(carboxypentyl)-thio]-2-benzimidazole carbamate protein conjug...

  9. Effect of the physicochemical parameters of benzimidazole molecules on their retention by a nonpolar sorbent from an aqueous acetonitrile solution

    Science.gov (United States)

    Shafigulin, R. V.; Safonova, I. A.; Bulanova, A. V.

    2015-09-01

    The effect of the structure of benzimidazoles on their chromatographic retention on octadecyl silica gel from an aqueous acetonitrile eluent was studied. One- and many-parameter correlation equations were obtained by linear regression analysis, and their prognostic potential in determining the retention factors of benzimidazoles under study was analyzed.

  10. Penta-substituted benzimidazoles as potent antagonists of the calcium-sensing receptor (CaSR-antagonists).

    Science.gov (United States)

    Gerspacher, Marc; Altmann, Eva; Beerli, René; Buhl, Thomas; Endres, Ralf; Gamse, Rainer; Kameni-Tcheudji, Jacques; Kneissel, Michaela; Krawinkler, Karl Heinz; Missbach, Martin; Schmidt, Alfred; Seuwen, Klaus; Weiler, Sven; Widler, Leo

    2010-09-01

    A series of novel benzimidazole derivatives has been designed via a scaffold morphing approach based on known calcilytics chemotypes. Subsequent lead optimisation led to the discovery of penta-substituted benzimidazoles that exhibit attractive in vitro and in vivo calcium-sensing receptor (CaSR) inhibitory profiles. In addition, synthesis and structure-activity relationship data are provided.

  11. Synthesis and biological evaluation of some novel-3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines

    Institute of Scientific and Technical Information of China (English)

    Vanga Malla Reddy; Kunduru Ravinder Reddy

    2010-01-01

    The synthesis of a new series of 3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines (6a-h) was achieved in excellent yields by the condensation of 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones (5a-h) with hydroxylamine at room temperature. These 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones (5a-h) were obtained by the condensation of 2-acetyl benzimidazoles (4a-d) with different aromatic aldehydes, which in turn were obtained by the oxidation of 2-(α-hydroxy)ethyl benzimidazoles (3a-d) prepared by the reaction of o-phenylenediamines (1a-d) with α-hydroxy propionic acid 2, The synthesized compounds were characterized by their IR, 1H NMR and MS analyses. These compounds were screened for their antibacterial and antifungal activity by standard methods and found some of them active.

  12. Substitution of benzimidazole-resistant nematodes for susceptible nematodes in grazing lambs.

    Science.gov (United States)

    Moussavou-Boussougou, M-N; Silvestre, A; Cortet, J; Sauve, C; Cabaret, J

    2007-04-01

    Multi-drug-resistant gastrointestinal nematode parasite populations are becoming more and more prevalent. Since anthelmintic treatments are of limited effectiveness, one solution could be to replace the anthelmintic-resistant population by a susceptible population, in order to re-establish the possibility of drug-based anthelmintic control. We investigated this substitution strategy in 4 paddocks of 0.7 ha, each of which was seeded with a benzimidazole-resistant Teladorsagia circumcincta population. The proportion of benzimidazole-resistant worms in these paddocks ranged from 20% to 89%. A 2-step replacement was performed: first, the paddocks were not grazed for 6 months (from December to July), and then the grass was cut to eliminate any residual infective larvae, before contaminating each of the paddocks with 10 seeder lambs experimentally infected with a benzimidazole-susceptible strain of T. circumcincta (from July to November). At the end of the experiment, all the populations on the 4 paddocks were phenotypically benzimidazole-susceptible, but genotyping indicated that 2 populations harboured 1% and 3% resistant worms respectively. This study demonstrates that nematode replacement is feasible in temperate areas, using semi-intensive stock management, even when the initial levels of benzimidazole-resistance are very high. Further research should next assess replacing the whole community to cope with the species diversity observed under field conditions. PMID:17096872

  13. 2-(4-Methylsulfanylphenyl-1H-benzimidazol-3-ium bromide

    Directory of Open Access Journals (Sweden)

    Mohamed Ziaulla

    2011-02-01

    Full Text Available In the cation of the title compound, C14H13N2S+·Br−, the essentially planar benzimidazole system (r.m.s. deviation = 0.0082 Å is substituted with a 4-methylsulfanylphenyl ring. The dihedral angle between the benzimidazole system and the 4-methylsulfanylphenyl ring is 2.133 (2°. The crystal structure is characterized by strong and highly directional intermolecular N—H...Br hydrogen bonds involving the bromide ion. Moreover, C—H...S interactions result in chains of molecules along the c axis. The supramolecular assembly is further stabilized by π–π stacking interactions between the benzimidazole system and 4-methylsulfanylphenyl rings [centroid–centroid distance = 3.477 (4 Å].

  14. Crystal structures and intermolecular interactions of two novel antioxidant triazolyl-benzimidazole compounds

    Science.gov (United States)

    Karayel, A.; Özbey, S.; Ayhan-Kılcıgil, G.; Kuş, C.

    2015-12-01

    The crystal structures of 5-(2-( p-chlorophenylbenzimidazol-1-yl-methyl)-4-(3-fluorophenyl)-2,4-dihydro-[1,2,4]-triazole-3-thione (G6C) and 5-(2-( p-chlorophenylbenzimidazol-1-yl-methyl)-4-(2-methylphenyl)-2,4-dihydro-[1,2,4]-triazole-3-thione (G4C) have been determined by single-crystal X-ray diffraction. Benzimidazole ring systems in both molecules are planar. The triazole part is almost perpendicular to the phenyl and the benzimidazole parts of the molecules in order to avoid steric interactions between the rings. The crystal structures are stabilized by intermolecular hydrogen bonds between the amino group of the triazole and the nitrogen atom of benzimidazole of a neighboring molecule.

  15. Effect of substituents on polarizability and hyperpolarizability values of benzimidazole metal complexes

    Science.gov (United States)

    Praveen, P. A.; Babu, R. Ramesh

    2016-05-01

    In this report, the polarizability and first and second order hyperpolarizability values of bis benzimidazole Zn(II)-2R and bis benzimidazole Cd(II)-2R complexes, with different electron donating moieties R (R= Cl, Br, I, Acetate) were calculated using time dependent Hartree-Fock (TDHF) formalism embedded in MOPAC2012 package. Further the role of substituents on polarizability and hyperpolarizability values is investigated for the first time by analyzing the frontier molecular orbitals of the complexes with respect to the electronegativity of the substituents. It is found that the increase in electronegativity of the substituents correspondingly increases the energy gap of the molecules, which in turn reduces the polarizability values of both Zn and Cd benzimidazole complexes. Similarly, increase in electronegativity reduces the electric quadrupole moments of both the metal complexes, which in turn reduces the hyperpolarizability values.

  16. Crystal structures and intermolecular interactions of two novel antioxidant triazolyl-benzimidazole compounds

    Energy Technology Data Exchange (ETDEWEB)

    Karayel, A., E-mail: matchlessjimmy@163.com, E-mail: yccaoh@hotmail.com; Özbey, S. [Hacettepe University, Physics Engineering Department (Turkey); Ayhan-Kılcıgil, G.; Kuş, C. [Ankara University, Department of Pharmaceutical Chemistry, Faculty of Pharmacy (Turkey)

    2015-12-15

    The crystal structures of 5-(2-(p-chlorophenylbenzimidazol-1-yl-methyl)-4-(3-fluorophenyl)-2, 4-dihydro-[1,2,4]-triazole-3-thione (G6C) and 5-(2-(p-chlorophenylbenzimidazol-1-yl-methyl)-4-(2-methylphenyl)-2, 4-dihydro-[1,2,4]-triazole-3-thione (G4C) have been determined by single-crystal X-ray diffraction. Benzimidazole ring systems in both molecules are planar. The triazole part is almost perpendicular to the phenyl and the benzimidazole parts of the molecules in order to avoid steric interactions between the rings. The crystal structures are stabilized by intermolecular hydrogen bonds between the amino group of the triazole and the nitrogen atom of benzimidazole of a neighboring molecule.

  17. JVG9, a benzimidazole derivative, alters the surface and cytoskeleton of Trypanosoma cruzi bloodstream trypomastigotes

    Science.gov (United States)

    Díaz-Chiguer, Dylan L; Hernández-Luis, Francisco; Nogueda-Torres, Benjamín; Castillo, Rafael; Reynoso-Ducoing, Olivia; Hernández-Campos, Alicia; Ambrosio, Javier R

    2014-01-01

    Trypanosoma cruzi has a particular cytoskeleton that consists of a subpellicular network of microtubules and actin microfilaments. Therefore, it is an excellent target for the development of new anti-parasitic drugs. Benzimidazole 2-carbamates, a class of well-known broad-spectrum anthelmintics, have been shown to inhibit the in vitro growth of many protozoa. Therefore, to find efficient anti-trypanosomal (trypanocidal) drugs, our group has designed and synthesised several benzimidazole derivatives. One, named JVG9 (5-chloro-1H-benzimidazole-2-thiol), has been found to be effective against T. cruzi bloodstream trypomastigotes under both in vitro and in vivo conditions. Here, we present the in vitro effects observed by laser scanning confocal and scanning electron microscopy on T. cruzi trypomastigotes. Changes in the surface and the distribution of the cytoskeletal proteins are consistent with the hypothesis that the trypanocidal activity of JVG9 involves the cytoskeleton as a target. PMID:25317703

  18. Lipase-Catalyzed Kinetic Resolution of Novel Antifungal N-Substituted Benzimidazole Derivatives.

    Science.gov (United States)

    Łukowska-Chojnacka, Edyta; Staniszewska, Monika; Bondaryk, Małgorzata; Maurin, Jan K; Bretner, Maria

    2016-04-01

    A series of new N-substituted benzimidazole derivatives was synthesized and their antifungal activity against Candida albicans was evaluated. The chemical step included synthesis of appropriate ketones containing benzimidazole ring, reduction of ketones to the racemic alcohols, and acetylation of alcohols to the esters. All benzimidazole derivatives were obtained with satisfactory yields and in relatively short times. All synthesized compounds exhibit significant antifungal activity against Candida albicans 900028 ATCC (% cell inhibition at 0.25 μg concentration > 98%). Additionally, racemic mixtures of alcohols were separated by lipase-catalyzed kinetic resolution. In the enzymatic step a transesterification reaction was applied and the influence of a lipase type and solvent on the enantioselectivity of the reaction was studied. The most selective enzymes were Novozyme SP 435 and lipase Amano AK from Pseudomonas fluorescens (E > 100). PMID:26922853

  19. Synthesis, Anti-Inflammatory and Anti-oxidant activity of some substituted Benzimidazole Derivatives

    Directory of Open Access Journals (Sweden)

    Rajasekaran S

    2012-09-01

    Full Text Available Benzimidazoles are an important class of compounds with a wide spectrum of biological activity ranging from anti-hypertensive, anti-viral, anti-fungal, antitumor and anthelmintic activity. In addition, few N-substituted benzimidazole derivatives have shown to exhibit significant activity against several viruses, including HIV, herpes simplex (HSV-1, influenza, picorna, human cytomegalovirus (HCMV and hepatitis C virus. The five membered heterocyclic moiety 1,3,4-oxadiazole also confers for various biological activity. Hence a series of benzimidazole derivatives fused with oxadiazole ring system have been synthesized, characterized by UV, IR and 1H NMR spectral data and evaluated for their in vitro and in vivo anti-inflammatory and antioxidant activity.

  20. Benzimidazole and imidazole lithium salts for battery electrolytes

    Energy Technology Data Exchange (ETDEWEB)

    Scheers, Johan; Johansson, Patrik; Jacobsson, Per [Department of Applied Physics, Chalmers University of Technology, SE-412 96 Goeteborg (Sweden); Szczecinski, Przemyslaw; Wieczorek, Wladyslaw [Polymer Ionics Research Group, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, PL-00664 Warsaw (Poland); Armand, Michel [Laboratoire de Reactivite et de Chimie des Solides, Universite de Picardie Jules Verne, 33 rue St. Leu, 80089 Amiens (France)

    2010-09-15

    The intrinsic anion oxidation potential ({delta}E{sub v}) and lithium ion pair dissociation energy ({delta}E{sub d}) are two important properties for predicting the potential use of new lithium salts for battery electrolytes. In this work several cyano substituted fluoroalkylated benzimidazole and imidazole anions have been investigated computationally to obtain {delta}E{sub v} and {delta}E{sub d}. Varying the number and position of cyano substituents results in large effects on the electrochemical stability of the anion and on the possible lithium ion pair configurations. The lengthening of the fluoroalkyl group introduces several new stable ion pair configurations and a small increase in anion oxidation stability. The most promising fluoroalkylated anions in the present work are the 4,5,6,7-tetracyano-2-fluoroalkylated benzimidazolides (TTB and PTB), with oxidation potentials suitable for high voltage Li-ion battery applications (<4.2 V) and much improved {delta}E{sub d} compared to PF{sub 6}{sup -} - a benchmark for commercially available anions. Further improvements in {delta}E{sub d}, with maintained stability towards oxidation, are obtainable by replacing the fluoroalkyl group by an additional cyano group, but possibly demanding increased synthesis efforts. (author)

  1. Cyanide detection using a benzimidazole derivative in aqueous media

    Science.gov (United States)

    Li, Jian-Bin; Hu, Jing-Han; Chen, Juan-Juan; Qi, Jing

    2014-12-01

    A novel cyanide selective fluorescent chemosensor S1 based on benzimidazole group and naphthalene group as the fluorescence signal group had been designed and synthesized. The receptor could instantly detect CN- anion over other anions such as F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4-, SCN- and ClO4- by fluorescence spectroscopy changes in aqueous solution (H2O/DMSO, 8:2, v/v) with specific selectivity and high sensitivity. The fluorescence color of the solution containing sensor S1 induced a remarkable color change from pale blue to mazarine only after the addition of CN- in aqueous solution while other anions did not cause obvious color change. Moreover, further study demonstrates the detection limit on fluorescence response of the sensor to CN- is down to 8.8 × 10-8 M, which is far lower than the WHO guideline of 1.9 × 10-6 M. Test strips based on S1 were fabricated, which could act as a convenient and efficient CN- test kit to detect CN- in pure water for “in-the-field” measurement. Thus, the probe should be potential applications in an aqueous environment for the monitoring of cyanide.

  2. DTPA: Bis benzimidazole as multi model imaging agent

    International Nuclear Information System (INIS)

    Full text: The DTPA bis benzimidazole analogue has been tested for radiopharmaceutical efficacy. The radiolabelling was found more then 98% after 8 hrs and blood kinetics was fast. The compound was also tested for optical imaging agent. The Eu3+ ion has an absorption band in the visible spectrum (578-582 nm) whose wavelength is very sensitive to even small changes in the coordination environment. Although the intensity of this 7F0 → 5D0 transition is low, the bands are relatively narrow, which allows distinguishing different coordination states of the metal. For Eu3+ complexes which have two differently hydrated forms in aqueous solution, one observes two absorption bands belonging to the two species. High-resolution UV-visible spectra were recorded in aqueous solutions which show a temperature invariant absorption with two distinct, temperature-dependent absorption bands. The intensity ratio of these two bands changes with temperature: the band at shorter wavelengths is decreasing very slightly, while that at longer wavelengths is increasing with the temperature. The ratio of the integrals of the two bands is related to the equilibrium constant, and its temperature dependence yields the reaction enthalpy and entropy

  3. Radiation effects on the stability of benzimidazole, which directly affects the stability of human DNA

    International Nuclear Information System (INIS)

    As all of us know that DNA is the genetic material and that is therefore stood at the very center of the study of life. Among the four important nitrogenous bases found in DNA one is purine which is nothing but a benzimidazole structure substituted by two nitrogens at 1 and 3 positions. Denaturation and renaturation duo to radiation are the two important incidents in DNA life which are the reason of many diseases and also the remedy of many diseases. These two incidents occur due to environmental effect on the parent part of DNA such as purine or we may say that benzimidazole structure. Since benzimidazole is an important part of human DNA structure so its response on different environment causes e huge effect on human gen. To study such response different types of benzimidazole molecules have been studied and two of such benzimidazole molecules are 2-Acetyl Benzomidazole (2ABI) and 2-Benzoyl Benzimidazole (2BBI). Usually these molecules show excited state proton transfer characteristics in polar and nonpolar environment. Proton transfer effect is very important behavior in DNA bases which is the fundamental phenomenon of different drug designing. To control such effect or to produce the effect as much as we want we have tried to restrict the molecule in different nano cavities. Michroheterogeneous media such as micelles as usual has enormous environmental effect on charge transfer phenomenon. The specialty of this media is that they have an ability to concentrate guest molecules into relatively small effective volumes and then to promote the re-encounter of such molecules. This property also makes micelles a good device for inducing efficient electrostatic interactions between the micelle head groups and the guest molecules. This electrostatic interaction has a direct effect on the stability of 2ABI and 2BBI molecule in ground state as well as in excited state due to micellization and this stability has enormous effect on human gene stability. (authors)

  4. Biological Activity and Molecular Structures of Bis(benzimidazole and Trithiocyanurate Complexes

    Directory of Open Access Journals (Sweden)

    Pavel Kopel

    2015-06-01

    Full Text Available 1-(1H-Benzimidazol-2-yl-N-(1H-benzimidazol-2-ylmethylmethanamine (abb and 2-(1H-benzimidazol-2-ylmethylsulfanylmethyl-1H-benzimidazole (tbb have been prepared and characterized by elemental analysis. These bis(benzimidazoles have been further used in combination with trithiocyanuric acid for the preparation of complexes. The crystal and molecular structures of two of them have been solved. Each nickel atom in the structure of trinuclear complex [Ni3(abb3(H2O3(μ-ttc](ClO43·3H2O·EtOH (1, where ttcH3 = trithiocyanuric acid, is coordinated with three N atoms of abb, the N,S donor set of ttc anion and an oxygen of a water molecule. The crystal of [(tbbH2(ttcH22(ttcH3(H2O] (2 is composed of a protonated bis(benzimidazole, two ttcH2 anions, ttcH3 and water. The structure is stabilized by a network of hydrogen bonds. These compounds were primarily synthesized for their potential antimicrobial activity and hence their possible use in the treatment of infections caused by bacteria or yeasts (fungi. The antimicrobial and antifungal activity of the prepared compounds have been evaluated on a wide spectrum of bacterial and yeast strains and clinical specimens isolated from patients with infectious wounds and the best antimicrobial properties were observed in strains after the use of ligand abb and complex 1, when at least 80% growth inhibition was achieved.

  5. 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.

  6. Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives.

    Science.gov (United States)

    El-Sayed, Taghreed H; Aboelnaga, Asmaa; Hagar, Mohamed

    2016-01-01

    Benzoic acid and o-phenylenediamine efficiently reacted under the green solvent-free Ball Milling method. Several reaction parameters were investigated such as rotation frequency; milling balls weight and milling time. The optimum reaction condition was milling with 56.6 g weight of balls at 20 Hz frequency for one hour milling time. The study was extended for synthesis of a series of benzimidazol-2-one or benzimidazol-2-thione using different aldehydes; carboxylic acids; urea; thiourea or ammonium thiocyanate with o-phenylenediamine. Moreover; the alkylation of benzimidazolone or benzimidazolthione using ethyl chloroacetate was also studied. PMID:27563861

  7. Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives

    Directory of Open Access Journals (Sweden)

    Taghreed H. EL-Sayed

    2016-08-01

    Full Text Available Benzoic acid and o-phenylenediamine efficiently reacted under the green solvent-free Ball Milling method. Several reaction parameters were investigated such as rotation frequency; milling balls weight and milling time. The optimum reaction condition was milling with 56.6 g weight of balls at 20 Hz frequency for one hour milling time. The study was extended for synthesis of a series of benzimidazol-2-one or benzimidazol-2-thione using different aldehydes; carboxylic acids; urea; thiourea or ammonium thiocyanate with o-phenylenediamine. Moreover; the alkylation of benzimidazolone or benzimidazolthione using ethyl chloroacetate was also studied.

  8. Polybenzimidazole Membranes Containing Benzimidazole Side Groups for High Temprature Polymer Electrolyte Membrane Fuel Cells

    DEFF Research Database (Denmark)

    Yang, Jingshuai; Li, Xueyuan; Xu, Yizin;

    2013-01-01

    Polybenzimidazole (PBI) with a high molecular weight of 69,000 was first synthesized. It was afterwards grafted with benzimidazole pendant groups on the backbones. The acid doped benzimidaozle grafted PBI membranes were investigated and characterized including fuel cell tests at elevated...... temperatures without humidification. At an acid doping level of 13.1 mol H3PO4 per average molar repeat unit, the PBI membranes with a benzimidazole grafting degree of 10.6% demonstrated a conductivity of 0.15 S cm-1 and a H2-air fuel cell peak power density of 378 mW cm-2 at 180 oC at ambient pressure without...

  9. 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.

  10. Synthesis, biological evaluation and SAR studies of benzimidazole derivatives as H1-antihistamine agents

    Institute of Scientific and Technical Information of China (English)

    Xiao Jian Wang; Mei Yang Xi; Ji Hua Fu; Fu Rong Zhang; Gui Fang Cheng; Da Li Yin; Qi Dong You

    2012-01-01

    A series of benzimidazole derivatives have been designed,synthesized and evaluated for H1 antihtistamine activity.Six compounds have showed potent antihistamine H1 activity.The primary SAR analysis indicated that benzyl or benzylidinyl substituted on the exo-nitrogen atom and C2 of the benzimidazole were significant.Further experiments indicated that compound 17d displayed excellent activity to reduce mast cell degranulation,moderate anti-PAF activity and decreased potency on hERG compared to astermizole.Hence compound 17d could serve as anti-altergic agent for further development.

  11. Solvent-free Rapid Synthesis of Styryl Dyes with Benzimidazole Nucleus Using Microwave Irradiation

    Institute of Scientific and Technical Information of China (English)

    Lan Ying WANG; Xiao Gang ZHANG; Ying Qi JIA; Zu Xun ZHANG

    2003-01-01

    The reactions of 2-methylbenzimidazole or 2-methylbenzimidazolium iodide with aromatic aldehydes are accelerated under microwave irradiation by using Ac2O or piperidine as dehydrant or catalyst in the absence of any solvent. The approach provides an attractive and environmentally friendly pathway to several useful styryl dyes with benzimidazole nucleus.

  12. 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.

  13. Eco-friendly synthesis of benzimidazole derivatives using solid acid scolecite catalyst

    Institute of Scientific and Technical Information of China (English)

    Lakshman S.Gadekar; Balasaheb R.Arbad; Machhindra K.Lande

    2010-01-01

    A series of benzimidazole derivatives were synthesized expeditiously in good yields by condensation of 1,2-diaminobenzene and aromatic aldehydes in the presence of modified scolecite catalyst.The world wide availability,easy handling and reusability of catalyst,higher yields and shorter reaction times are the advantages of the present method.

  14. Silica Sulfuric Acid: An Eco-Friendly and Reusable Catalyst for Synthesis of Benzimidazole Derivatives

    Directory of Open Access Journals (Sweden)

    Bahareh Sadeghi

    2013-01-01

    Full Text Available Silica sulfuric acid (SiO2-OSO3H as an eco-friendly, readily available, and reusable catalyst is applied to benzimidazole derivatives synthesis under reflux in ethanol. The procedure is very simple and the products are isolated with an easy workup in good-to-excellent yields.

  15. Standardization of the egg hatch test for the detection of benzimidazole resistance in parasitic nematodes

    NARCIS (Netherlands)

    Samson-Himmelstjerna, von G.; Coles, G.; Jackson, F.; Bauer, C.; Borgsteede, F.H.M.; Cirak, V.; Demeler, J.; Donnan, A.; Dorny, P.; Epe, C.; Harder, A.; Hoglund, J.; Kaminsky, R.; Kerboeuf, D.; Kuttler, U.; Papadopoulos, E.; Posedi, J.; Small, J.; Varady, M.; Verscruysse, J.; Wirtherle, N.

    2009-01-01

    The ability to reliably detect anthelmintic resistance is a crucial part of resistance management. If data between countries are to be compared, the same test should give the same results in each laboratory. As the egg hatch test for benzimidazole resistance is used for both research and surveys, th

  16. Recognition of HIV-TAR RNA using neomycin-benzimidazole conjugates.

    Science.gov (United States)

    Ranjan, Nihar; Kumar, Sunil; Watkins, Derrick; Wang, Deyun; Appella, Daniel H; Arya, Dev P

    2013-10-15

    Synthesis of a novel class of compounds and their biophysical studies with TAR-RNA are presented. The synthesis of these compounds was achieved by conjugating neomycin, an aminoglycoside, with benzimidazoles modeled from a B-DNA minor groove binder, Hoechst 33258. The neomycin-benzimidazole conjugates have varying linkers that connect the benzimidazole and neomycin units. The linkers of varying length (5-23 atoms) in these conjugates contain one to three triazole units. The UV thermal denaturation experiments showed that the conjugates resulted in greater stabilization of the TAR-RNA than either neomycin or benzimidazole used in the synthesis of conjugates. These results were corroborated by the FID displacement and tat-TAR inhibition assays. The binding of ligands to the TAR-RNA is affected by the length and composition of the linker. Our results show that increasing the number of triazole groups and the linker length in these compounds have diminishing effect on the binding to TAR-RNA. Compounds that have shorter linker length and fewer triazole units in the linker displayed increased affinity towards the TAR RNA.

  17. Aminosilanes derived from 1H-benzimidazole-2(3H)-thione

    Energy Technology Data Exchange (ETDEWEB)

    Palomo-Molina, Juliana [Facultad de Ciencias Químicas, Universidad de Colima, Carretera Coquimatlán-Colima, Coquimatlán Colima 28400 (Mexico); García-Báez, Efrén V. [Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Avenida Acueducto s/n, Barrio La Laguna Ticomán, México DF 07340 (Mexico); Contreras, Rosalinda [Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, Apartado Postal 14-740, México DF 07000 (Mexico); Barrio La Laguna Ticomán, México DF 07340 (Mexico); Pineda-Urbina, Kayim; Ramos-Organillo, Angel, E-mail: aaramos@ucol.mx [Facultad de Ciencias Químicas, Universidad de Colima, Carretera Coquimatlán-Colima, Coquimatlán Colima 28400 (Mexico)

    2015-08-12

    In two trimethylsilyl-substituted 1H-benzimidazole-2(3H)-thiones, noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe{sub 3} groups form helicoidal arrangements in one, and dimerization results in the formation of R{sub s} {sup 2}(8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings, in the second compound. Two new molecular structures, namely 1,3-bis(trimethylsilyl)-1H-benzimidazole-2(3H)-thione, C{sub 13}H{sub 22}N{sub 2}SSi{sub 2}, (2), and 1-trimethylsilyl-1H-benzimidazole-2(3H)-thione, C{sub 10}H{sub 14}N{sub 2}SSi, (3), are reported. Both systems were derived from 1H-benzimidazole-2(3H)-thione. Noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe{sub 3} groups form helicoidal arrangements in (2). Dimerization of (3) results in the formation of R{sub 2}{sup 2}(8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings.

  18. Aminosilanes derived from 1H-benzimidazole-2(3H)-thione

    International Nuclear Information System (INIS)

    In two trimethylsilyl-substituted 1H-benzimidazole-2(3H)-thiones, noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe3 groups form helicoidal arrangements in one, and dimerization results in the formation of Rs 2(8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings, in the second compound. Two new molecular structures, namely 1,3-bis(trimethylsilyl)-1H-benzimidazole-2(3H)-thione, C13H22N2SSi2, (2), and 1-trimethylsilyl-1H-benzimidazole-2(3H)-thione, C10H14N2SSi, (3), are reported. Both systems were derived from 1H-benzimidazole-2(3H)-thione. Noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe3 groups form helicoidal arrangements in (2). Dimerization of (3) results in the formation of R22(8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings

  19. Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles

    OpenAIRE

    Ying Chen; Dan-Wen Zhuang; Dong-Mei Cui; Chen Zhang

    2011-01-01

    A gold-catalyzed oxidation of arylallenes to form α-diketones and aldehydes in good yields is presented. Further directed synthesis of quinoxalines and benzimidazoles, via the condensation of the resulting α-diketones and aldehydes with benzene-1,2-diamine, was achieved in high yields.

  20. 3-[(1H-Benzimidazol-2-yl)sulfanylmethyl]benzonitrile

    OpenAIRE

    Jin Rui Lin; Jia He; Yang Qian; Hong Zhao

    2009-01-01

    In the title compound, C15H11N3S, the dihedral angle between the benzimidazole ring system and the benzene ring is 51.8 (2)°. The crystal structure exhibits intermolecular N—H...N hydrogen bonds which lead to the formation of C(4) chains along the [001] direction.

  1. Ammonium metavanadate: A novel catalyst for synthesis of 2-substituted benzimidazole derivatives

    Institute of Scientific and Technical Information of China (English)

    Ganesh R. Jadhav; Mohammad U. Shaikh; Rajesh P. Kale; Charansingh H. Gill

    2009-01-01

    Ammonium metavanadate (10 tool%) was found to be a useful catalyst for the synthesis of various 2-substituted aryl benzimidazoles. It was used as an oxidizing agent for the condensation of o-pbenylenediamine with different substituted aryl aldehydes at room temperature in ethanol. The method was proved to be simple, convenient and the product was isolated with good yields (79-91%).

  2. Benzimidazoles diminish ERE transcriptional activity and cell growth in breast cancer cells

    Energy Technology Data Exchange (ETDEWEB)

    Payton-Stewart, Florastina [Department of Chemistry, College of Arts and Sciences, Xavier University of Louisiana, New Orleans, LA (United States); Tilghman, Syreeta L. [Division of Basic Pharmaceutical Sciences, College of Pharmacy, Xavier University of Louisiana, New Orleans, LA (United States); Williams, LaKeisha G. [Division of Clinical and Administrative Sciences, College of Pharmacy Xavier University of Louisiana, New Orleans, LA (United States); Winfield, Leyte L., E-mail: lwinfield@spelman.edu [Department of Chemistry, Spelman College, Atlanta, GA (United States)

    2014-08-08

    Highlights: • The methyl-substituted benzimidazole was more effective at inhibiting growth in MDA-MB 231 cells. • The naphthyl-substituted benzimidazole was more effective at inhibiting growth in MCF-7 cells than ICI. • The benzimidazole molecules demonstrated a dose-dependent reduction in ERE transcriptional activity. • The benzimidazole molecules had binding mode in ERα and ERβ comparable to that of the co-crystallized ligand. - Abstract: Estrogen receptors (ERα and ERβ) are members of the nuclear receptor superfamily. They regulate the transcription of estrogen-responsive genes and mediate numerous estrogen related diseases (i.e., fertility, osteoporosis, cancer, etc.). As such, ERs are potentially useful targets for developing therapies and diagnostic tools for hormonally responsive human breast cancers. In this work, two benzimidazole-based sulfonamides originally designed to reduce proliferation in prostate cancer, have been evaluated for their ability to modulate growth in estrogen dependent and independent cell lines (MCF-7 and MDA-MB 231) using cell viability assays. The molecules reduced growth in MCF-7 cells, but differed in their impact on the growth of MDA-MB 231 cells. Although both molecules reduced estrogen response element (ERE) transcriptional activity in a dose dependent manner, the contrasting activity in the MDA-MB-231 cells seems to suggest that the molecules may act through alternate ER-mediated pathways. Further, the methyl analog showed modest selectivity for the ERβ receptor in an ER gene expression array panel, while the naphthyl analog did not significantly alter gene expression. The molecules were docked in the ligand binding domains of the ERα-antagonist and ERβ-agonist crystal structures to evaluate the potential of the molecules to interact with the receptors. The computational analysis complimented the results obtained in the assay of transcriptional activity and gene expression suggesting that the molecules

  3. 苯并咪唑衍生物的合成及表征%Synthesis and Characterization of Benzimidazole Derivatives

    Institute of Scientific and Technical Information of China (English)

    刘博; 杨晓峰; 靳强; 陈志萍

    2014-01-01

    氧气作为氧化剂,邻苯二胺与芳醛为原料,甲醇为溶剂,反应合成了2种苯并咪唑类衍生物:2-(4-甲基苯基)苯并咪唑,2-(4-溴苯基)苯并咪唑,应用傅里叶红外光谱仪、核磁共振仪和元素分析仪分析和表征了目标化合物的结构。%Oxygen as the oxidant, two benzimidazole derivatives were synthesized with aromatic aldehydes and 1,2-diaminobenzene as raw materials in methanol. Two kinds of benzimidazole derivatives were 2-(4-methylphenyl)benzimidazole and 2-(4-bromophenyl)-benzimidazole. The product was characterized by FTIR, 1H-NMR and elemental analysis.

  4. Synthesis and Structure of Zinc Complex of N, N-bis ( benzimidazol-2-yl-methyl ) amine

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    The Zinc complex of N, N-bis (benzimidazol-2-yl-methyl)amine has been synthesized and its crystal structure determined by X-ray diffraction method. The structure features of the complex are described.

  5. Fluorescent silica hybrid materials containing benzimidazole dyes obtained by sol-gel method and high pressure processing

    Energy Technology Data Exchange (ETDEWEB)

    Hoffmann, Helena Sofia; Stefani, Valter; Benvenutti, Edilson Valmir [Instituto de Quimica, Universidade Federal do Rio Grande do Sul, Av. Bento Goncalves, 9500, CP 15003 CEP 91501-970, Porto Alegre (Brazil); Costa, Tania Maria Haas, E-mail: taniaha@iq.ufrgs.br [Instituto de Quimica, Universidade Federal do Rio Grande do Sul, Av. Bento Goncalves, 9500, CP 15003 CEP 91501-970, Porto Alegre (Brazil); Gallas, Marcia Russman [Instituto de Fisica, Universidade Federal do Rio Grande do Sul, Av. Bento Goncalves, 9500, CP 15051 CEP 91501-970, Porto Alegre (Brazil)

    2011-03-15

    Research highlights: {yields} Sol-gel technique was used to obtain silica based hybrid materials containing benzimidazole dyes. {yields} The sol-gel catalysts, HF and NaF, produce xerogels with different optical and textural characteristics. {yields} High pressure technique (6.0 GPa) was used to produce fluorescent and transparent silica compacts with the dyes entrapped in closed pores, maintaining their optical properties. {yields} The excited state intramolecular proton transfer (ESIPT) mechanism of benzimidazole dyes was studied by steady-state fluorescence spectroscopy for the monoliths, powders, and compacts. - Abstract: New silica hybrid materials were obtained by incorporation of two benzimidazole dyes in the silica network by sol-gel technique, using tetraethylorthosilicate (TEOS) as inorganic precursor. Several syntheses were performed with two catalysts (HF and NaF) producing powders and monoliths with different characteristics. The dye 2-(2'-hydroxy-5'-aminophenyl)benzimidazole was dispersed and physically adsorbed in the matrix, and the dye 2'(5'-N-(3-triethoxysilyl)propylurea-2'-hydroxyphenyl)benzimidazole was silylated, becoming chemically bonded to the silica network. High pressure technique was used to produce fluorescent and transparent silica compacts with the silylated and incorporated dye, at 6.0 GPa and room temperature. The excited state intramolecular proton transfer (ESIPT) mechanism of benzimidazole dyes was studied by steady-state fluorescence spectroscopy for the monoliths, powders, and compacts. The influence of the syntheses conditions was investigated by textural analysis using nitrogen adsorption isotherms.

  6. Crystal structure of bis[2-(1H-benzimidazol-2-ylaniline]silver(I nitrate

    Directory of Open Access Journals (Sweden)

    Yongtae Kim

    2015-09-01

    Full Text Available In the cation of the title salt, [Ag(C13H11N32]NO3, the AgI atom lies on a crystallographic inversion center and is coordinated by four N atoms from two bidentate 2-(1H-benzimidazol-2-ylaniline ligands in a distorted square-planar geometry. The Ag—N(aniline bond [2.729 (2 Å] is significantly longer than the Ag—N(imidazole bond [2.165 (1 Å]. In the ligand, the aniline ring is twisted by 37.87 (6° from the mean plane of the benzimidazole ring system. The nitrate anion lies on a crystallographic twofold rotation axis which passes through the N atom and one of the O atoms. In the crystal, N—H...O hydrogen bonds link the components, forming a layer parallel to the bc plane.

  7. Benzimidazole Based 'Turn on' Fluorescent Chemodosimeter for Zinc Ions in Mixed Aqueous Medium.

    Science.gov (United States)

    Sharma, Shilpa; Pradeep, Chullikkattil P; Dhir, Abhimanew

    2016-07-01

    Benzimidazole based compound 3 is designed and synthesized. The compound 3 is evaluated as fluorogenic sensor for metal ions in mixed aqueous solutions. Among all the metal ions tested, the compound 3 selectively senses Zn(2+) ions. The imine bond of 3 gets cleaved by Zn(2+) ions. Thus, 3 behave as 'turn on' fluorescent chemodosimeter for Zn(2+) ions with limit of detction in micromolar range. Furthurmore, we demonstated that 3 can detect Zn(2+) ions in cells of Allium cepa. Graphical Abstract Benzimidazole based ligand 3 is designed and synthesized which behave as chemodosimeter for Zn(2+) ions. We further demonstrated that 3 can detect Zn(2+) ions in cells of Allium cepa. PMID:27262442

  8. A Mild and Efficient Synthesis of Benzimidazole by Using Zinc Chloride under Solvent Free Condition

    Directory of Open Access Journals (Sweden)

    Mahajan Tushar

    2013-02-01

    Full Text Available A straightforward, efficient and more sustainable solvent-free method has been developed for the synthesis of benzimidazole derivatives to achieve yields that were comparable to or better than, those in conventional media. It is noteworthy that the reaction was exclusively carried out in Zinc chloride catalysis system, rendering the methodology highly valuable from both environment and economic points of view. The various benzimidazoles were synthesized by the reaction of o-phenylenediamine with different types of aldehydes and characterized by their Physical constant, FT-IR Spectra, 1H NMR Spectra and LCMS. The excellent chemo selectivity, mild reaction condition, short reaction times and excellent yield made the best method then other methods.

  9. Orthorhombic polymorph of 4-[(1H-benzimidazol-1-ylmethyl]benzoic acid

    Directory of Open Access Journals (Sweden)

    Hai-Wei Kuai

    2011-11-01

    Full Text Available We reported recently the first polymorph of the title compound [Kuai & Cheng (2011a. Acta Cryst., E67, o2787]. A second polymorph of the title compound, C15H12N2O2, was unexpectedly obtained by the hydrothermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.015 (2 Å. The benzimidazole and benzene rings are inclined at a dihedral angle of 79.00 (1°. In the crystal, adjacent molecules are connected through O—H...N hydrogen bonds into a one-dimensional chain along the [001] direction.

  10. Synthesis and anti-Plasmodium activity of benzimidazole analogues structurally related to astemizole.

    Science.gov (United States)

    Roman, Gheorghe; Crandall, Ian E; Szarek, Walter A

    2013-11-01

    A series of compounds structurally related to astemizole were designed and synthesized with the goal of determining their anti-Plasmodium activity. Several modifications of the astemizole structure, namely the removal of the 4-fluorobenzyl and/or 4-methoxyphenethyl moieties, substitution of the benzene ring of the benzimidazole scaffold, replacement of the fluorine atom in the 4-fluorobenzyl group, and variation of the 4-aminopiperidine moiety, were explored. In vitro evaluation of the anti-Plasmodium activity of these compounds using the ItG strain showed that astemizole and some of its structurally similar derivatives have IC50 values in the nanomolar range and exhibit toxicity towards the parasite over Chinese ovarian hamster (CHO) cells with a selectivity as high as 200. The presence of a secondary cyclic amine at position 2 and substitution with chlorine at positions 4 and 5 in the benzimidazole moiety are two modifications that resulted in potent and selective antimalarials based on astemizole. PMID:24022991

  11. Synthesis of 2-Substituted Benzimidazoles and 1,5-Disubstituted Benzodiazepines on Alumina and Zirconia Catalysts

    Institute of Scientific and Technical Information of China (English)

    M. REKH; A. HAMZA; B. R. VENUGOPAE; N. NAGARAJU

    2012-01-01

    In this study, alumina, zirconia, manganese oxide/alumina, and manganese oxide/zirconia have been investigated for their catalytic activity in the condensation reaction between o-phenylenediamine and an aldehyde or a ketone to synthesise 2-substituted benzimidazoles and 1,5-disubstituted benzodiazepines respectively. Surface area, surface acidity, and morphology of the catalysts have been analysed and correlated with their catalytic activity. The isolated yields of 2-substituted benzimidazoles and 1,5-disubstituted benzodiazepines are in the range of 30% to 95%. A good correlation between the amount of surface acid sites as well as the surface morphology of the catalysts and the catalytic activity has been observed. This method has been found to be simple and economical. The solid supports could be regenerated and reused without much loss in their activity. Further, the solid supports have been also found to be effective as general catalysts in the condensation of o-phenylenediamine with other substituted aldehydes and ketones.

  12. 1,3-Dibenzyl-1H-benzimidazol-2(3H-one

    Directory of Open Access Journals (Sweden)

    Youssef Kandri Rodi

    2011-12-01

    Full Text Available In the molecular structure of the title compound, C21H18N2O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0121 (9 Å. The O atom and adjacent C atom are located in Wyckoff position 4e on a twofold axis (0, y, 1/4. The two benzyl groups are almost perpendicular to the benzimidazole plane, but point in opposite directions. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 81.95 (5°, whereas that between the two benzyl groups is 60.96 (7°.

  13. Syntheses of Nickel (II Complexes from Novel Semicarbazone Ligands with Chloroformylarylhydrazine, Benzimidazole and Salicylaldehyde Moieties

    Directory of Open Access Journals (Sweden)

    Mei-Hsiu Shih

    2015-03-01

    Full Text Available This study addressed the design and syntheses of diverse ligands, which were then successfully treated with Ni (II ion to afford a series of nickel complexes. α-Chloroformylarylhydrazine hydrochlorides 6 contain two different functional groups. One is a strong nucleophile, and the other is a good electrophile. Therefore, it can be designed to react with several reagents to obtain diverse derivatives which can be used as ligands for metal complexes. Furthermore, benzimidazole and salicylaldehyde can provide electron donor sites, N and O electron donors, separately. Hence, the starting materials α-chloroformylarylhydrazine hydrochlorides 6 were first treated with 2-(aminomethyl-benzimidazole (7 to give the corresponding semicarbazides 8. Then, the semicarbazides 8 reacted with various substituted salicylaldehydes 9–11 to afford the desired substituted-salicylaldehyde 2-aryl-4-substituted semicarbazones 12–14, which could coordinate with nickel (II ion to give the corresponding nickel complexes 15–17.

  14. New Route to 3-Alkylthiazolo[3,2-a]benzimidazole Derivatives

    Directory of Open Access Journals (Sweden)

    Nicolas Vanthuyne

    2005-02-01

    Full Text Available 3-Alkyl-thiazolo[3,2-a]benzimidazole derivatives are obtained in high yieldsvia the corresponding 4-alkyl-N-3-(2-aminophenyl-thiazoline-2-thiones which are easilyprepared from 1,2-diaminobenzene, CS2 and halogenoketones. This new route comparesadvantageously with the classical mercaptobenzimidazole routes in term of simplicity,isolated yields and availability of the starting materials.

  15. A Rapid Access to Novel and Known Benzimidazole Derivatives Using Silica Chloride as a Reusable Catalyst

    Institute of Scientific and Technical Information of China (English)

    Karami, Bahador; Ghashghaee, Vahideh; Khodabakhshi, Saeed

    2012-01-01

    A new application of silica chloride as an easily available and reusable solid acid catalyst for the synthesis of benzimidazole and its derivatives through the condensation of o-phenylenediamines and orthoesters under thermal and solvent-free conditions is described. This novel and eco-friendly method is very cheap and has many advan- tages including excellent yields, short reaction time, and simple work-up procedure.

  16. A new benzimidazole based covalent organic polymer having high energy storage capacity.

    Science.gov (United States)

    Patra, Bidhan C; Khilari, Santimoy; Satyanarayana, Lanka; Pradhan, Debabrata; Bhaumik, Asim

    2016-06-18

    We report the synthesis of a new benzimidazole-based covalent organic polymer (TpDAB) via solvothermal Schiff base condensation between 1,3,5-triformylphloroglucinol (Tp) and 3,3'-diaminobenzidine (DAB). TpDAB showed high energy storage capacity with a specific capacitance of 335 F g(-1) at 2 mV s(-1) scan rate and good cyclic stability with 93% retention of its initial specific capacitance after 1000 cycles. PMID:27222226

  17. Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene fused by benzimidazole.

    Science.gov (United States)

    Sakai, Hayato; Kubota, Takako; Yuasa, Junpei; Araki, Yasuyuki; Sakanoue, Tomo; Takenobu, Taishi; Wada, Takehiko; Kawai, Tsuyoshi; Hasobe, Taku

    2016-07-12

    Benzimidazole-fused [5]carbohelicene ([5]HeliBI) was newly synthesized to examine the spectroscopic and chiroptical properties. The reversible protonation and deprotonation processes of [5]HeliBI were successfully investigated using (1)H NMR, absorption and fluorescence spectral measurements. We also confirmed the circularly polarized luminescence of protonated [5]HeliBI (H(+)-[5]HeliBI). This is the first observation of red-coloured CPL of a helicene derivative. PMID:27319321

  18. 4-Methyl-N-(2-phenylethyl-2-propyl-1H-benzimidazole-6-carboxamide

    Directory of Open Access Journals (Sweden)

    Jin-Liang Wang

    2012-10-01

    Full Text Available There are two independent molecules in the asymmetric unit of the title compound, C20H23N3O, in which the dihedral angles between the phenyl ring of the phenylethylamino group and the benzimidazole system are 73.98 (15 and 15.93 (16°. The crystal packing features N—H...O and N—H...N hydrogen bonds.

  19. Structure of adducts of isoindolo[2,1-a]benzimidazole derivatives with maleimides

    Science.gov (United States)

    Korolev, Oleksandr; Yegorova, Tatyana; Levkov, Igor; Malytskyy, Volodymyr; Shishkin, Oleg; Zubatyuk, Roman; Palamarchuk, Genadiy; Vedrenne, Marc; Baltas, Michel; Voitenko, Zoia

    2015-03-01

    The selectivity of formation and some mechanistic insights during the synthesis of substituted isoindolo[2,1-a]benzimidazoles are discussed. Furthermore, the reactions of the obtained products with maleimides were carried out. Two types rearrangement adducts together with intermediate Michael type adducts were isolated. The influence of the reaction conditions and reagents ratio is discussed. Specific spectral criteria for the identification of the Michael type adducts are indicated.

  20. Specific fluorescent sensing of aluminium using naphthalene benzimidazole derivative in aqueous media

    Science.gov (United States)

    Velmurugan, K.; Mathankumar, S.; Santoshkumar, S.; Amudha, S.; Nandhakumar, R.

    2015-03-01

    Naphthalene benzimidazole conjugate bearing a hydroxyl group was synthesized. Its binding properties towards various metal ions were examined and it showed a high selectivity and sensitivity towards Al3+ ions in aqueous media. The recognition processes follows a photo induced electron transfer (PET) mechanism assisted with the restricted intramolecular C-C single bond rotation and are scarcely influenced by other coexisting metal ions. In addition, determination of Al3+ in a variety of sewage water samples was also determined.

  1. 1-(2,3,4,5,6-Pentamethylbenzyl)-2-(pyridin-2-yl)-1H-benzimidazole

    OpenAIRE

    Fırat Anĝay; Ömer Çelik; Orhan Barlık; Mahmut Ulusoy

    2014-01-01

    In the title compound, C24H25N3, the benzimidazole ring system is essentially planar, with an r.m.s. deviation of 0.017 Å, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the pyridine and benzene rings, respectively. An intramolecular C—H...N hydrogen bond is observed. In the crystal, molecules are stacked along the a axis by weak C—H...π interactions.

  2. Design, synthesis, and antiviral properties of 2-aryl-lH-benzimidazole-4-carboxamide derivatives

    Institute of Scientific and Technical Information of China (English)

    Xianjin LUO; Zhonglü ZHANG; Yutian YANG; Fei XUE; Naiyun XIU; Yuanbin SHE

    2009-01-01

    A series of new benzimidazole derivatives were designed and synthesized. Their chemical structures were testified by 1H NMR, infrared spectroscopy (IR), mass spectrography (MS), and elemental analysis. Their potent antiviral properties indicated the prospect of new drugs. Compound 13, 16, 18, 19, 21, 22, and 23 were identified as novel antivirus with much better selective activity and inhibitory activity than the comparable ribavirin against Coxsackie virus B3 in VERO cells.

  3. Design, synthesis, α-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives

    Science.gov (United States)

    Dinparast, Leila; Valizadeh, Hassan; Bahadori, Mir Babak; Soltani, Somaieh; Asghari, Behvar; Rashidi, Mohammad-Reza

    2016-06-01

    In this study the green, one-pot, solvent-free and selective synthesis of benzimidazole derivatives is reported. The reactions were catalyzed by ZnO/MgO containing ZnO nanoparticles as a highly effective, non-toxic and environmentally friendly catalyst. The structure of synthesized benzimidazoles was characterized using spectroscopic technics (FT-IR, 1HNMR, 13CNMR). Synthesized compounds were evaluated for their α-glucosidase inhibitory potential. Compounds 3c, 3e, 3l and 4n were potent inhibitors with IC50 values ranging from 60.7 to 168.4 μM. In silico studies were performed to explore the binding modes and interactions between enzyme and synthesized benzimidazoles. Developed linear QSAR model based on density and molecular weight could predict bioactivity of newly synthesized compounds well. Molecular docking studies revealed the availability of some hydrophobic interactions. In addition, the bioactivity of most potent compounds had good correlation with estimated free energy of binding (ΔGbinding) which was calculated according to docked best conformations.

  4. Novel organic dyes based on phenyl-substituted benzimidazole for dye sensitized solar cells

    Energy Technology Data Exchange (ETDEWEB)

    Saltan, Gözde Murat [Department of Chemistry, Faculty of Arts and Science, Celal Bayar University, Yunus Emre, 45140 Manisa (Turkey); Dinçalp, Haluk, E-mail: haluk.dincalp@cbu.edu.tr [Department of Chemistry, Faculty of Arts and Science, Celal Bayar University, Yunus Emre, 45140 Manisa (Turkey); Kıran, Merve; Zafer, Ceylan [Solar Energy Institute, Ege University, Bornova, 35100 Izmir (Turkey); Erbaş, Seçil Çelik [Celal Bayar University, Materials Engineering Department, Faculty of Engineering, Yunus Emre, 45140 Manisa (Turkey)

    2015-08-01

    Two new sensitizers derived from benzimidazole core for dye-sensitized solar cell (DSSC) applications were designed and synthesized as D–π–A structures, in which two phenyl-substituted benzimidazole group, a phenyl ring and a cyanoacrylic acid were used as the electron donor, π-conjugated linkage and the electron acceptor, respectively. Effect of methoxy- and N,N-dimetylamino- moieties attached to the phenyl groups of benzimidazole were investigated by means of optical and photovoltaic measurements. The compounds exhibit broad absorption maximum at 387 nm with the tail extending up to 500 nm on TiO{sub 2}-coated thin film. The longer wavelength absorption band around 360 nm and the much longer decay components could be attributed to the existence of charge transfer state of the dyes in solutions. DSSC device fabricated by using methoxy substituted dye (BI5a) as a sensitizer shows much better incident photon-to-current conversion efficiency (IPCE) of 64% giving cell efficiency of 2.68%. - Graphical abstract: Display Omitted - Highlights: • Long decay times suggest the delayed fluorescence caused by the existence of ICT. • The best solar energy conversion efficiency was obtained for BI5a dye (2.68%). • More fluorescent BI5a dye gives higher photocurrent generation.

  5. Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-1ong carbon chain alkyl benzimidazole

    Institute of Scientific and Technical Information of China (English)

    Junzhen ZHANG; Bingqin YANG; Yating YANG; Binglin ZHANG

    2009-01-01

    Six new 1-ferrocenesulfonyl-2-benzimidazole derivatives were prepared by the reaction of ferrocene-sulfonyl chloride with benzimidazole derivatives in the presence of dichloromethane and n-tetrabutylammonia bromide. The yields of these six new ferrocenesulfonyl benzimidazole derivatives were about 80%. The structures characteristic were confirmed by IR, 1H-NMR, Elemental analysis and MS. The crystal structure of compound a2 was determined via X-ray single crystal diffraction and it belongs to monoclinic system with space group C2/c,and the unit cell parameters are a=2.8252(2)nm, b=0.97696(7)nm, c=1.64828(12)nm, a=90°, β=92.053(2)°,y = 90°, V= 4.5466(6) nm3, Z= 8, F(000) =2024, Mr=481.40, Dc=l.407g/cm3, μ=0.784mm-1,R1=0.0495, wR2=0.1517. The results show that the reactions of 2-alkylbenzimidazoles containing active hydrogen with ferrocenesulfonyl chloride gave 1-ferrocenesulfonyl-2-alkylbenzimidazoles in good yields.

  6. Benzimidazole-Branched Isomeric Dyes: Effect of Molecular Constitution on Photophysical, Electrochemical, and Photovoltaic Properties.

    Science.gov (United States)

    Bodedla, Govardhana Babu; Justin Thomas, K R; Fan, Miao-Syuan; Ho, Kuo-Chuan

    2016-01-15

    Three benzimidazole-based isomeric organic dyes possessing two triphenylamine donors and a cyanoacrylic acid acceptor are prepared by stoichiometrically controlled Stille or Suzuki-Miyaura coupling reaction which predominantly occurs on the N-butyl side of benzimidazole due to electronic preferences. Combined with the steric effect of the N-butyl substituent, placement of the acceptor segment at various nuclear positions of benzimidazole such as C2, C4, and C7 led to remarkable variations in intramolecular charge transfer absorption, electron injection efficiency, and charge recombination kinetics. The substitution of acceptor on the C4 led to red-shifted absorption, while that on C7 retarded the charge transfer due to twisting in the structure caused by the butyl group. Because of the cross-conjugation nature and poor electronic interaction between the donor and acceptor, the dye containing triphenylamine units on C4 and C7 and the acceptor unit on C2 showed the low oxidation potential. Thus, this dye possesses favorable HOMO and LUMO energy levels to render efficient sensitizing action in solar cells. Consequently, it results in high power conversion efficiency (5.01%) in the series with high photocurrent density and open circuit voltage. The high photocurrent generation by this dye is reasoned to it exceptional charge collection efficiency as determined from the electron impedance spectroscopy. PMID:26679036

  7. 2-(4-Hydroxyphenyl-1H-benzimidazol-3-ium chloride monohydrate

    Directory of Open Access Journals (Sweden)

    Jazmin E. González-Padilla

    2013-09-01

    Full Text Available The title molecular salt, C13H11N2O+·Cl−·H2O, crystallizes as a monohydrate. In the cation, the phenol and benzimidazole rings are almost coplanar, making a dihedral angle of 3.18 (4°. The chloride anion and benzimidazole cation are linked by two N+—H...Cl− hydrogen bonds, forming chains propagating along [010]. These chains are linked through O—H...Cl hydrogen bonds involving the water molecule and the chloride anion, which form a diamond core, giving rise to the formation of two-dimensional networks lying parallel to (10-2. Two π–π interactions involving the imidazolium ring with the benzene and phenol rings [centroid–centroid distances = 3.859 (3 and 3.602 (3 Å, respectively], contribute to this second dimension. A strong O—H...O hydrogen bond involving the water molecule and the phenol substituent on the benzimidazole unit links the networks, forming a three-dimensional structure.

  8. A trisubstituted benzimidazole cell division inhibitor with efficacy against Mycobacterium tuberculosis.

    Directory of Open Access Journals (Sweden)

    Susan E Knudson

    Full Text Available Trisubstituted benzimidazoles have demonstrated potency against Gram-positive and Gram-negative bacterial pathogens. Previously, a library of novel trisubstituted benzimidazoles was constructed for high throughput screening, and compounds were identified that exhibited potency against M. tuberculosis H37Rv and clinical isolates, and were not toxic to Vero cells. A new series of 2-cyclohexyl-5-acylamino-6-N, N-dimethylaminobenzimidazoles derivatives has been developed based on SAR studies. Screening identified compounds with potency against M. tuberculosis. A lead compound from this series, SB-P17G-A20, was discovered to have an MIC of 0.16 µg/mL and demonstrated efficacy in the TB murine acute model of infection based on the reduction of bacterial load in the lungs and spleen by 1.73 ± 0.24 Log10 CFU and 2.68 ± Log10 CFU, respectively, when delivered at 50 mg/kg by intraperitoneal injection (IP twice daily (bid. The activity of SB-P17G-A20 was determined to be concentration dependent and to have excellent stability in mouse and human plasma, and liver microsomes. Together, these studies demonstrate that SB-P17G-A20 has potency against M. tuberculosis clinical strains with varying susceptibility and efficacy in animal models of infection, and that trisubstituted benzimidazoles continue to be a platform for the development of novel inhibitors with efficacy.

  9. Synthesis, antimicrobial and cytotoxic activity of novel azetidine-2-one derivatives of 1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Malleshappa Noolvi

    2014-04-01

    Full Text Available A series of 1-methyl-N-[(substituted-phenylmethylidene-1H-benzimidazol-2-amines (4a–4g were prepared via the formation of 1-methyl-1H-benzimidazol-2-amine (3, which was prepared by the cycloaddition of o-phenylenediamine (1 with cyanogen bromide in the presence of aqueous base followed by N-methylation with methyl iodide in the presence of anhydrous potassium carbonate in dry acetonitrile. Moreover, the four-membered β-lactam ring was introduced by the cycloaddition of 4a–4g and chloroacetyl chloride in the presence of triethylamine catalyst to give 3-chloro-1-(1-methyl-1H-benzimidazol-2-yl-(4′-substituted-phenylazetidin-2-one 5a–5g. A total of 14 compounds were synthesized and characterized by IR, 1H NMR, 13C NMR and Mass spectral technique, in addition they were evaluated for anti-bacterial and cytotoxic properties. Among the chemicals tested 4a, 4b, 5a, 5b, 5g exhibited good antibacterial activity and 5f, 5g shown good cytotoxic activity in vitro.

  10. Novel coumarin-benzimidazole derivatives as antioxidants and safer anti-inflammatory agents.

    Science.gov (United States)

    Arora, Radha Krishan; Kaur, Navneet; Bansal, Yogita; Bansal, Gulshan

    2014-10-01

    Inspired from occurrence of anti-inflammatory activity of 3-substituted coumarins and antiulcer activity of various 2-substituted benzimidazoles, novel compounds have been designed by coupling coumarin derivatives at 3-position directly or through amide linkage with benzimidazole nucleus at 2-position. The resultant compounds are expected to exhibit both anti-inflammatory and antioxidant activities along with less gastric toxicity profile. Two series of coumarin-benzimidazole derivatives (4a-e and 5a-e) were synthesized and evaluated for anti-inflammatory activity and antioxidant activity. Compounds 4c, 4d and 5a displayed good anti-inflammatory (45.45%, 46.75% and 42.85% inhibition, respectively, versus 54.54% inhibition by indomethacin) and antioxidant (IC50 of 19.7, 13.9 and 1.2 µmol/L, respectively, versus 23.4 µmol/L for butylatedhydroxytoluene) activities. Evaluation of ulcer index and in vivo biochemical estimations for oxidative stress revealed that compounds 4d and 5a remain safe on gastric mucosa and did not induce oxidative stress in tissues. Calculation of various molecular properties suggests the compounds to be sufficiently bioavailable. PMID:26579406

  11. (1H-1,3-Benzimidazole-5,6-dicarboxylic acid(5-carboxylato-1H-1,3-benzimidazole-6-carboxylic acidsilver(I monohydrate

    Directory of Open Access Journals (Sweden)

    Hong Zhai

    2009-11-01

    Full Text Available The title compound, [Ag(C9H5N2O4(C9H6N2O4]·H2O, contains one independent Ag atom, a neutral 1H-benzimidazole-5,6-dicarboxylic acid (bdcH, its monodeprotonated form, i.e. 5-carboxylato-1H-1,3-benzimidazole-6-carboxylic acid (bdc, and one solvent water molecule, the latter being disordered over three sites with site occupancy factors of 0.375 (× 2 and 0.25. In addition, the H atom on one carboxylic acid residue is disordered, being connected to each of the O atoms 50% of the time. The Ag atom is in a virtually linear geometry defined by two N atoms derived from the bdc and bdcH ligands. The three-dimensional supramolecular structure is stablized by extensive O—H...O and N—H...O hydrogen bonds. An intramolecular O—H...O hydrogen bond is also present.

  12. Mating type idiomorphs distribution and their correlation to benzimidazole-resistance in Cercospora beticola from the Central High Plains Region, USA

    Science.gov (United States)

    Cercospora leaf spot (CLS) of sugarbeet is caused by Cercospora beticola Sacc., and is one of the most destructive foliar diseases worldwide. Fungicides used for disease suppression include benzimidazoles. Resistance to benzimidazoles can develop quickly, and was first reported in C. beticola in 197...

  13. A genetic algorithm based determination of the ground and excited (L-1(b)) state structure and the orientation of the transition dipole moment of benzimidazole

    NARCIS (Netherlands)

    Schmitt, M.; Krugler, D.; Bohm, M.; Ratzer, C.; Bednarska, V.A.; Kalkman, I.M.; Meerts, W.L.

    2006-01-01

    The structure of benzimidazole has been determined in the electronic ground and excited states using rotationally resolved electronic spectroscopy. The rovibronic spectra of four isotopomers and subsequently the structure of benzimidazole have been automatically assigned and fitted using a genetic a

  14. Conjugation of benzylvanillin and benzimidazole structure improves DNA binding with enhanced antileukemic properties.

    Directory of Open Access Journals (Sweden)

    Zena A Al-Mudaris

    Full Text Available Benzyl-o-vanillin and benzimidazole nucleus serve as important pharmacophore in drug discovery. The benzyl vanillin (2-(benzyloxy-3-methoxybenzaldehyde compound shows anti-proliferative activity in HL60 leukemia cancer cells and can effect cell cycle progression at G2/M phase. Its apoptosis activity was due to disruption of mitochondrial functioning. In this study, we have studied a series of compounds consisting of benzyl vanillin and benzimidazole structures. We hypothesize that by fusing these two structures we can produce compounds that have better anticancer activity with improved specificity particularly towards the leukemia cell line. Here we explored the anticancer activity of three compounds namely 2-(2-benzyloxy-3-methoxyphenyl-1H-benzimidazole, 2MP, N-1-(2-benzyloxy-3-methoxybenzyl-2-(2-benzyloxy-3-methoxyphenyl-1H-benzimidazole, 2XP, and (R and (S-1-(2-benzyloxy-3-methoxyphenyl-2, 2, 2-trichloroethyl benzenesulfonate, 3BS and compared their activity to 2-benzyloxy-3-methoxybenzaldehyde, (Bn1, the parent compound. 2XP and 3BS induces cell death of U937 leukemic cell line through DNA fragmentation that lead to the intrinsic caspase 9 activation. DNA binding study primarily by the equilibrium binding titration assay followed by the Viscosity study reveal the DNA binding through groove region with intrinsic binding constant 7.39 µM/bp and 6.86 µM/bp for 3BS and 2XP respectively. 2XP and 3BS showed strong DNA binding activity by the UV titration method with the computational drug modeling showed that both 2XP and 3BS failed to form any electrostatic linkages except via hydrophobic interaction through the minor groove region of the nucleic acid. The benzylvanillin alone (Bn1 has weak anticancer activity even after it was combined with the benzimidazole (2MP, but after addition of another benzylvanillin structure (2XP, stronger activity was observed. Also, the combination of benzylvanillin with benzenesulfonate (3BS significantly improved

  15. Thermostability and photophysical properties of mixed-ligand carboxylate/benzimidazole Zn(II)-coordination polymers

    Energy Technology Data Exchange (ETDEWEB)

    Barros, Bráulio Silva, E-mail: brauliobarros@ect.ufrn.br [School of Science and Technology, Federal University of Rio Grande do Norte (UFRN), Campus Universitário Lagoa Nova, 59078-970 Natal, RN (Brazil); Chojnacki, Jaroslaw [Department of Inorganic Chemistry, Chemical Faculty, Gdansk University of Technology, G. Narutowicza 11/12, 80-233 Gdansk (Poland); Macêdo Soares, Antonia Alice; Kulesza, Joanna; Lourenço da Luz, Leonis; Júnior, Severino Alves [Department of Fundamental Chemistry, Federal University of Pernambuco (UFPE), Av. Prof. Moraes Rego, 1235 – Cidade Universitária, 50670-901 Recife, PE (Brazil)

    2015-07-15

    The reaction between Zn(NO{sub 3}){sub 2}·6H{sub 2}O or Zn(CH{sub 3}COO){sub 2}·2H{sub 2}O and isophthalic acid (1,3-H{sub 2}bdc) in the presence of benzimidazole (Hbzim) in dimethylformamide (DMF)/ethanol (EtOH)/H{sub 2}O solvent mixture at room temperature yielded two structurally different coordination polymers: [Zn{sub 2}(1,3-bdc){sub 2}(Hbzim){sub 2}] (1) and [Zn{sub 2}(1,3-bdc)(bzim){sub 2}] (2). (1) is a 2D-layered framework with a molecule of benzimidazole coordinated to the Zn center, whereas (2) is a 3D framework with benzimidazolate species acting as a co-ligand and bridging two Zn(II) ions. Reactions performed at 90 °C led to the formation of coordination polymers structurally similar to (2), independently of the Zn(II) source used. In the absence of benzimidazole, the reaction between ZnAc{sub 2}.2H{sub 2}O and 1,3-H{sub 2}bdc at 90 °C resulted in the formation of (3), a 3D coordination polymer Zn(HCOO){sub 3}(Me{sub 2}NH{sub 2}{sup +}). It was observed that the thermostability and the photophysical properties of (1) and (2) are strongly dependent on the coordination modes and packing of benzimidazole in the solid state. These materials present photoluminescence in the wide range of the spectrum, from UV to IR. A full understanding of a physical process occurring in these intriguing systems, including complete energy level diagrams with possible transitions were provided. - Graphical abstract: Display Omitted - Highlights: • Structurally different Zn(II)-coordination polymers were prepared. • The formation of frameworks was counter anion and temperature dependent. • Photoluminescence in the wide range of the spectrum, from UV to IR was observed. • Thermostability and luminescence depended on bzim packing in the structure.

  16. Development and application of loop-mediated isothermal amplification for detecting the highly benzimidazole-resistant isolates in Sclerotinia sclerotiorum.

    Science.gov (United States)

    Duan, Ya Bing; Yang, Ying; Wang, Jian Xin; Liu, Cong Chao; He, Ling Ling; Zhou, Ming Guo

    2015-01-01

    Resistance of benzimidazole fungicides is related to the point mutation of the β-tubulin gene in Sclerotinia sclerotiorum. The point mutation at codon 198 (GAG → GCG, E198A) occurs in more than 90% of field resistant populations in China. Traditional detection methods of benzimidazole-resistant mutants of S. sclerotiorum are time-consuming, tedious and inefficient. To establish a suitable and rapid detection of benzimidazole-resistant mutants of S. sclerotiorum, an efficient and simple method with high specificity was developed based on loop-mediated isothermal amplification (LAMP). Eight sets of LAMP primers were designed and four sets were optimized to specially distinguish benzimidazole-resistant mutants of S. sclerotiorum. With the optimal LAMP primers, the concentration of LAMP components was optimized and the reaction conditions were set as 60-64 °C for 60 min. This method had a good specificity, sensitivity, stability and repeatability. In the 1491 sclerotia, 614 (41.18%) were positive by LAMP, and 629 (42.19%) positive by MIC. Therefore, the LAMP assay is more feasible to detect benzimidazole-resistant mutants of S. sclerotiorum than traditional detection methods. PMID:26606972

  17. Synthesis and Characterization of 2-[1h- Benzimidazole- 2yl-Sulfanyl]-N-[(E-Furan-2-Yl- Methylidene] Aceto Hydrazide

    Directory of Open Access Journals (Sweden)

    Ramesh Dhani

    2012-10-01

    Full Text Available Heterocyclic chemistry comprises at least half of all organic chemistry research worldwide. In particular, heterocyclic structures form the basis of many pharmaceutical, agrochemical and veterinary products. The benzimidazole contains a phenyl ring fused to an imidazole ring, as indicated in the structure of benzimidazole. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. By using different synthetic methods new benzimidazole derivatives were synthesized and further Melting points were determined by using Precision melting point apparatus in open capillaries and are uncorrected. The purity of the compounds was checked by TLC on silica gel G plates using n-Hexane, ethyl acetate (1:3 and methanol: chloroform (1:9 solvent system. The synthesized benzimidazole derivatives were characterized by IR, 1H NMR spectral analysis. Benzimidazole is a lead nucleus for future developments to get effective compounds.

  18. Ethyl 1-[2-(morpholin-4-ylethyl]-2-[4-(trifluoromethylphenyl]-1H-benzimidazole-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Yeong Keng Yoon

    2011-05-01

    Full Text Available In the title compound, C23H24F3N3O3, the morpholine ring adopts a chair conformation. The benzimidazole ring is approximately planar, with a maximum deviation of 0.028 (1 Å for one of the unsubstituted C atoms. The benzimidazole ring makes dihedral angles of 35.66 (4 and 75.45 (5° with the attached phenyl and morpholine rings, respectively. In the crystal structure, adjacent molecules are linked via C—H...F and C—H...O hydrogen bonds to form a two-dimensional network.

  19. Bis(benzimidazole-κN3bis(2-benzoylbenzoato-κOcopper(II

    Directory of Open Access Journals (Sweden)

    M. Hakkı Yıldırım

    2009-06-01

    Full Text Available In the title centrosymmetric mononuclear copper(II compound, [Cu(C14H9O32(C7H6N22], the central CuII ion is coordinated by two N atoms from two symmetry-related benzimidazole (bim ligands and two O atoms from two symmetry-related 2-benzoylbenzoate (2-byba ligands in a square-planar geometry. The molecules are linked into chains running along the b axis by N—H...O hydrogen bonds and the chains are cross-linked by C—H...π interactions.

  20. Crystal assembly based on 3,5-bis(2'-benzimidazole) pyridine and its complexes

    Science.gov (United States)

    Tong, Shan Ling; Tian, Zhao Yong; Wu, Ya Hong; Yan, Yan; Hu, Sheng; Yu, Jian

    2013-03-01

    Imdazole, pyridine and their derivatives have been considered as excellent ligands in supramolecular self-assembly. In this paper, a ligand molecule 3,5-bis (2'-benzimidazole) pyridine (BBP) was prepared, and two different crystal architectures based on the ligand molecule were self-assembled by diffusion/solvothermal ways. Furthermore, several crystal architectures of several relative complexes were also successfully assembled. These crystal structures were well defined by X-ray diffractions. Structural resolutions indicated that, as building blocks, this bibenzimidazole pyridine molecules exhibited coordination varieties in constructing the crystal architectures based on its related complexes.

  1. 2-[4-(1H-1,2,4-Triazol-1-ylphenyl]-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Long-Huai Cheng

    2012-10-01

    Full Text Available In the title compound, C15H11N5, the benzimidazole ring system is nearly planar [maximum deviation = 0.039 (2 Å], and is oriented at a dihedral angle of 28.85 (10° with respect to the benzene ring; the dihedral angle between the triazole and benzene rings is 17.30 (15°. In the crystal N—H...N hydrogen bonds link the molecules into chains. Weak C—H...N interactions are also present.

  2. 2-Heteroaryl Benzimidazole Derivatives as Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists

    Energy Technology Data Exchange (ETDEWEB)

    Lim, Chae Jo; Kim, Jeong Young; Lee, Byung Ho; Oh, Kwangseok; Yi, Kyu Yang [Korea Research Institute of Chemical Technology, Daejeon (Korea, Republic of)

    2013-08-15

    A novel series of 2-heteroaryl substituted benzimidazole derivatives, containing the piperidinylphenyl acetamide group at the 1-position, were synthesized and evaluated as MCH-R1 antagonists. Extensive SAR investigation probing the effects of C-2 heteroaryl group led to the identification of 2-[2-(pyridin-3-yl)ethyl] analog 3o, which exhibits highly potent MCH-R1 binding activity with an IC{sub 50} value of 1 nM. This substance 3o also has low hERG binding activity, good metabolic stability, and favorable pharmacokinetic properties.

  3. 2-sec-Butyl-1-(2-hydroxyethyl-1H-benzimidazole-5-carboxylic acid

    Directory of Open Access Journals (Sweden)

    Nurasyikin Hamzah

    2012-07-01

    Full Text Available In the title compound, C14H18N2O3, the carboxylic group is tilted by 12.00 (4° with respect to the mean plane throught the benzimidazole ring system. The alcohol and carboxyl hydroxy groups are involved in intermolecular O—H...O and O—H...N hydrogen bonds, forming a two-dimensional network extending parallel the ab plane. The network is further stabilized by weak C—H...O interactions. The sec-butyl group is disordered over two sets of sites with refined occupancies of 0.484 (4 and 0.516 (4.

  4. Glycerol Containing Triacetylborate Mediated Syntheses of Novel 2-Heterostyryl Benzimidazole Derivatives: A Green Approach

    Directory of Open Access Journals (Sweden)

    Ashok Kumar Taduri

    2014-01-01

    Full Text Available A very simple, mild, efficient, and novel green methodology has been developed for the syntheses of some 2-hetero/styryl-benzimidazoles. Title compounds were synthesized by the condensation of o-phenylenediamine with cinnamic acids at 150–180°C for 5-6 h using glycerol containing triacetylborate (10–20 mol% as the reaction medium. In an alternative approach, condensation of 2-methylbenzimidazole derivatives with aromatic aldehydes was done using glycerol containing triacetylborate (10–20 mol% as the reaction medium.

  5. (S-2-(2-Pyrrolidinio-1H-benzimidazol-3-ium dichloride monohydrate

    Directory of Open Access Journals (Sweden)

    Dai Jing

    2009-06-01

    Full Text Available In the title compound, C11H15N32+·2Cl−·H2O, one N atom of the imidazole ring and the N atom of the pyrrolidine ring are protonated. The crystal structure is stabilized by aromatic π–π interactions between the benzene rings of neighbouring benzimidazole systems [centroid–centroid duistance = 3.712 (2 Å]. The crystal structure is further stabilized by intermolecular N—H...Cl, O—H...Cl and N—H...O hydrogen bonds.

  6. Synthesis, crystal structure and spectroscopic studies of bismuth(III) complex with 2-substituted benzimidazole ligands

    Science.gov (United States)

    Li, Chuan-Hua; Tao, Xu; Jiang, Jian-Hong; Li, Xu; Xiao, Sheng-Xiong; Tao, Li-Ming; Zhou, Ju-Feng; Zhang, Hui; Xie, Ming-An; Zhu, Yi; Xia, Zi; Tang, Si-Min; Yuan, Han-Meng; Li, Qiang-Guo

    2016-09-01

    Reaction of BiCl3 with 2-(2-hydroxy-3-methoxyphenyl)benzimidazole (HL) in tetrahydrofuran (THF) under reflux gave mononuclear complex of formula [Bi(HL)2Cl3·H2O]. The binding interaction of the complex with bovine serum albumin (BSA) was investigated using the fluorescence quenching method. The experimental results showed that the complex could bind to BSA in the proportion of about 1:1. The binding reaction was spontaneous and hydrophobic force played major role in the reaction. The binding of the complex to BSA could change the microenvironment and conformation of BSA.

  7. Resistance to benzimidazoles and levamisole in nematode parasites of sheep in Nyandarua district of Kenya

    DEFF Research Database (Denmark)

    Maingi, N.; Bjørn, H.; Gichohi, V.M.;

    1998-01-01

    The occurrence of anthelmintic resistance on 25 sheep farms in the Nyandarua District of Kenya was investigated, using the faecal egg count reduction test (FECRT), the egg hatch assay (EHA) and a larval development assay (LDA). In the FECRT, resistance to both benzimidazoles (BZs) and levamisole....... The LD50 values for TBZ in the LDA for four of the six isolates with BZ resistance in the FECRT were higher than 0.5 mu M (0.59-2.07) TBZ. There were disagreements in ascribing resistance for various farms, between methods of calculating and interpreting the faecal egg count reduction percentages (FECR...

  8. Efficient Synthesis of Functionalized Benzimidazoles and Perimidines: Ytterbium Chloride Catalyzed CmC Bond Cleavage%Efficient Synthesis of Functionalized Benzimidazoles and Perimidines: Ytterbium Chloride Catalyzed CmC Bond Cleavage

    Institute of Scientific and Technical Information of China (English)

    Cai, Lijian; Ji, Xiaofeng; Yao, Zhigang; Xu, Fan; Shen, Qi

    2011-01-01

    An efficient method is developed for the synthesis of functionalized benzimidazoles and perimidines by the condensation of aryl diamines with β-carbonyl compounds catalyzed by ytterbium chloride. The reactions give good yields under mild conditions. A mechanism involving a lanthanide activated C--C bond cleavage is proposed.

  9. Synthesis and structural studies of amino amide salts derived from 2-(aminomethyl)benzimidazole and α-amino acids

    Science.gov (United States)

    Avila-Montiel, Concepción; Tapia-Benavides, Antonio R.; Falcón-León, Martha; Ariza-Castolo, Armando; Tlahuext, Hugo; Tlahuextl, Margarita

    2015-11-01

    2-{[(Ammoniumacetyl)amino]methyl}-1H-benzimidazol-3-ium dichloride 4, 2-{[(2-ammoniumpropanoyl)amino]methyl}-1H-benzimidazol-3-ium dichloride 5, and 2-{[(2-ammonium-3-phenylpropanoyl)amino]methyl}-1H-benzimidazol-3-ium dichloride 6 amino amides were synthesized via condensation of 2AMBZ dihydrochloride with the corresponding amino acid. Compounds 7-12 were obtained by replacing chloride ions (in salts 4-6) with nitrate or tetrachlorozincate ions. The results of X-ray diffraction crystallographic studies indicated that the geometries, charges and sizes of the anions are essential for the formation of the strong hydrogen bond interactions of compounds 4, 5, 9-12. Moreover, in most cases, the presence of water and solvent molecules stabilizes the supramolecular structures of these compounds. Nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy indicated that the presence of chloride or tetrachlorozincate anions increases the acidity of the benzimidazolic and amide groups more significantly than the presence of nitrate anions. However, Quantum Theory of Atoms in Molecules (QTAIM) computations of the crystal structures demonstrate that amino amides interact more strongly with NO3- than with Cl- and ZnCl42- anions; this difference explains the spectroscopic results.

  10. Synthesis and optical properties of novel pyrido[1,2-a]benzimidazole-containing 1,3,4-oxadiazole derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Yang He; Ge Yanqing; Jia Jiong [Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan, Shandong 250100 (China); Wang Jianwu, E-mail: jwwang@sdu.edu.c [Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan, Shandong 250100 (China)

    2011-04-15

    A series of novel substituted 1,3,4-oxadiazole derivatives containing pyrido[1,2-a]benzimidazole moiety were synthesized and characterized using FTIR, {sup 1}H NMR, {sup 13}C NMR, and HRMS. An efficient tandem reaction was employed as a key step in constructing the pyrido[1,2-a]benzimidazole moiety under very mild condition. The structure of compound 4a was established by X-ray crystallography. The UV-vis absorption and fluorescence spectral characteristics of these compounds were investigated in several solvents. Compounds 4a-i display similar absorptions, with absorption peaks ranging from 330 to 339 nm in acetonitrile, while the absorption maxima of compound 4j bearing a diphenylamino group on the benzene ring is red-shifted distinctly to 377 nm due to the strong electron-donating property of its substituent and extended {pi}-conjugated system. All these target heterocyclic compounds present blue-green emissions (461-487 nm) in dilute solutions and show high quantum yields of fluorescence ({phi}{sub PL}=0.65-0.99) in dichloromethane. - Research Highlights: The first report about the unique optical properties of pyrido[1,2-a]benzimidazole heteroaromatic compounds containing 1,3,4-oxadiazole unit. Synthesis of pyrido[1,2-a]benzimidazole moiety via a novel efficient tandem reaction. The target heterocyclic compounds showing high quantum yields of fluorescence, with great potential for use as fluorescent pigments and in optical/electro devices.

  11. Synthesis of novel chelating benzimidazole-based carbenes and their nickel(II) complexes: activity in the Kumada coupling reaction

    NARCIS (Netherlands)

    Berding, J.; Lutz, M.; Spek, A.L.; Bouwman, E.

    2009-01-01

    Nickel(II) halide complexes of novel chelating bidentate benzimidazole-based N-heterocyclic carbenes have been prepared from Ni(OAc)2 and bisbenzimidazolium salts. Single-crystal X-ray structure determination on four complexes revealed a cis-geometry on a square-planar nickel center. The complexes a

  12. An Efficient and Convenient Synthesis of Imidazolines and Benzimidazoles via Oxidation of Carbon-Nitrogen Bond in Water Media

    Institute of Scientific and Technical Information of China (English)

    Shaikh, Kabeer A.; Patil, Vishal A.; Shaikh, Parveen A.

    2012-01-01

    The metal coordination complex K4[Fe(CN)6] is an efficient and environmentally benign catalyst for the syn- thesis of imidazolines and benzimidazoles from various aldehydes and 1,2-diamines in aqueous medium at room temperature. This protocol gives excellent yield of product with desired purity.

  13. Design, synthesis, molecular docking and biological evaluation of new dithiocarbamates substituted benzimidazole and chalcones as possible chemotherapeutic agents.

    Science.gov (United States)

    Bacharaju, Keerthana; Jambula, Swathi Reddy; Sivan, Sreekanth; Jyostnatangeda, Saritha; Manga, Vijjulatha

    2012-05-01

    A series of novel dithiocarbamates with benzimidazole and chalcone scaffold have been designed synthesised and evaluated for their antimitotic activity. Compounds 4c and 9d display the most promising antimitotic activity with IC(50) of 1.66 μM and 1.52 μM respectively. PMID:22460028

  14. Design, synthesis, molecular docking and biological evaluation of new dithiocarbamates substituted benzimidazole and chalcones as possible chemotherapeutic agents.

    Science.gov (United States)

    Bacharaju, Keerthana; Jambula, Swathi Reddy; Sivan, Sreekanth; Jyostnatangeda, Saritha; Manga, Vijjulatha

    2012-05-01

    A series of novel dithiocarbamates with benzimidazole and chalcone scaffold have been designed synthesised and evaluated for their antimitotic activity. Compounds 4c and 9d display the most promising antimitotic activity with IC(50) of 1.66 μM and 1.52 μM respectively.

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

    Science.gov (United States)

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

    2012-02-01

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

  16. Antiproliferative activity of bicyclic benzimidazole nucleosides: synthesis, DNA-binding and cell cycle analysis.

    Science.gov (United States)

    Sontakke, Vyankat A; Lawande, Pravin P; Kate, Anup N; Khan, Ayesha; Joshi, Rakesh; Kumbhar, Anupa A; Shinde, Vaishali S

    2016-04-26

    An efficient route was developed for synthesis of bicyclic benzimidazole nucleosides from readily available d-glucose. The key reactions were Vörbruggen glycosylation and ring closing metathesis (RCM). Primarily, to understand the mode of DNA binding, we performed a molecular docking study and the binding was found to be in the minor groove region. Based on the proposed binding model, UV-visible and fluorescence spectroscopic techniques using calf thymus DNA (CT-DNA) demonstrated a non-intercalative mode of binding. Antiproliferative activity of nucleosides was tested against MCF-7 and MDA-MB-231 breast cancer cell lines and found to be active at low micromolar concentrations. Compounds and displayed significant antiproliferative activity as compared to and with the reference anticancer drug, doxorubicin. Cell cycle analysis showed that nucleoside induced cell cycle arrest at the S-phase. Confocal microscopy has been performed to validate the induction of cellular apoptosis. Based on these findings, such modified bicyclic benzimidazole nucleosides will make a significant contribution to the development of anticancer drugs. PMID:27074628

  17. Structure of eight molecular salts assembled from noncovalent bonding between carboxylic acids, imidazole, and benzimidazole

    Science.gov (United States)

    Jin, Shouwen; Zhang, Huan; Liu, Hui; Wen, Xianhong; Li, Minghui; Wang, Daqi

    2015-09-01

    Eight organic salts of imidazole/benzimidazole have been prepared with carboxylic acids as 2-methyl-2-phenoxypropanoic acid, α-ketoglutaric acid, 5-nitrosalicylic acid, isophthalic acid, 4-nitro-phthalic acid, and 3,5-dinitrosalicylic acid. The eight crystalline forms reported are proton-transfer compounds of which the crystals and compounds were characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. These structures adopted hetero supramolecular synthons, with the most common R22(7) motif observed at salts 2, 3, 5, 6 and 8. Analysis of the crystal packing of 1-8 suggests that there are extensive strong Nsbnd H⋯O, and Osbnd H⋯O hydrogen bonds (charge assisted or neutral) between acid and imidazolyl components in all of the salts. Except the classical hydrogen bonding interactions, the secondary propagating interactions also play important roles in structure extension. This variety, coupled with the varying geometries and number of acidic groups of the acids utilized, has led to the creation of eight supramolecular arrays with 1D-3D structure. The role of weak and strong noncovalent interactions in the crystal packing is analyzed. The results presented herein indicate that the strength and directionality of the Nsbnd H⋯O, and Osbnd H⋯O hydrogen bonds between acids and imidazole/benzimidazole are sufficient to bring about the formation of organic salts.

  18. Synthesis and activity of benzimidazole-1,3-dioxide inhibitors of separase.

    Science.gov (United States)

    Do, Ha T; Zhang, Nenggang; Pati, Debananda; Gilbertson, Scott R

    2016-09-15

    Due to the oncogenic activity of cohesin protease, separase in human cancer cells, modulation of separase enzymatic activity could constitute a new therapeutic strategy for targeting resistant, separase-overexpressing aneuploid tumors. Herein, we report the synthesis, structural information, and structure-activity relationship (SAR) of separase inhibitors based on modification of the lead molecule 2,2-dimethyl-5-nitro-2H-benzimidazole-1,3-dioxide, named Sepin-1, (1) identified from a high-throughput-screen. Replacement of -NO2 at C5 with other functional groups reduce the inhibitory activity in separase enzymatic assay. Substitution of the two methyl groups with other alkyl chains at the C2 moderately improves the effects on the inhibitory activity of those compounds. Modifications on 2H-benzimidazole-1,3-dioxide or the skeleton have variable effect on inhibition of separase enzymatic activity. Density-functional theory (DFT) calculations suggest there may be a correlation between the charges on the oxide moieties on these compounds and their activity in inhibiting separase enzyme. PMID:27530289

  19. Experimental and Theoretical Study of the Reactivity of Gold Nanoparticles Towards Benzimidazole-2-ylidene Ligands.

    Science.gov (United States)

    Rodríguez-Castillo, María; Lugo-Preciado, Gustavo; Laurencin, Danielle; Tielens, Frederik; van der Lee, Arie; Clément, Sébastien; Guari, Yannick; López-de-Luzuriaga, José M; Monge, Miguel; Remacle, Françoise; Richeter, Sébastien

    2016-07-18

    The reactivity of benzimidazol-2-ylidenes with respect to gold nanoparticles (AuNPs) has been investigated using a combined experimental and computational approach. First, the grafting of benzimidazol-2-ylidenes bearing benzyl groups on the nitrogen atoms is described, and comparisons are made with structurally similar N-heterocyclic carbenes (NHCs) bearing other N-groups. Similar reactivity was observed for all NHCs, with 1) the erosion of the AuNPs under the effect of the NHC and 2) the formation of bis(NHC) gold complexes. DFT calculations were performed to investigate the modes of grafting of such ligands, to determine adsorption energies, and to rationalize the spectroscopic data. Two types of computational models were developed to describe the grafting onto large or small AuNPs, with either periodic or cluster-type DFT calculations. Calculations of NMR parameters were performed on some of these models, and discussed in light of the experimental data. PMID:27344993

  20. Enhanced Carbon Dioxide Capture from Landfill Gas Using Bifunctionalized Benzimidazole-Linked Polymers.

    Science.gov (United States)

    Islamoglu, Timur; Behera, Swayamprabha; Kahveci, Zafer; Tessema, Tsemre-Dingel; Jena, Puru; El-Kaderi, Hani M

    2016-06-15

    Tuning the binding affinity of small gases and their selective uptake by porous adsorbents are vital for effective CO2 removal from gas mixtures for environmental protection and fuel upgrading. In this study, an amine-functionalized benzimidazole-linked polymer (BILP-6-NH2) was synthesized by a combination of pre- and postsynthetic modification techniques in two steps. Presynthetic incorporation of nitro groups resulted in stoichiometric functionalization (1 nitro/phenyl) in addition to noninvasive functionalization, where more than 80% of the surface area maintained compared to BILP-6. Experimental studies presented enhanced CO2 uptake and CO2/CH4 selectivity in BILP-6-NH2 compared to BILP-6, which are governed by the synergetic effect of benzimidazole and amine moieties. DFT calculations were used to understand the interaction modes of CO2 with BILP-6-NH2 and confirmed the efficacy of amine groups. Encouraged by the enhanced uptake and selectivity in BILP-6-NH2, we have evaluated its performance in landfill gas separation under vacuum swing adsorption (VSA) settings, which resulted in very promising working capacity and sorbent selection parameters outperforming most of the best solid adsorbent in the literature. PMID:27228220

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

    Science.gov (United States)

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

    2011-09-01

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

  2. Sequence variation in the Trichuris trichiura beta-tubulin locus: implications for the development of benzimidazole resistance.

    Science.gov (United States)

    Bennett, A B; Anderson, T J C; Barker, G C; Michael, E; Bundy, D A P

    2002-11-01

    Benzimidazole resistance has evolved in a variety of organisms and typically results from mutations in the beta-tubulin locus at specific amino acid sites. Despite widespread treatment of human intestinal nematodes with benzimidazole drugs, there have been no unambiguous reports of resistance. However, since beta-tubulin mutations conferring resistance are generally recessive, frequencies of resistance alleles less than 30% would be difficult to detect on the basis of drug treatment failures. Here we investigate sequence variation in a 1079 bp segment of the beta-tubulin locus in the human whipworm Trichuris trichiura from 72 individual nematodes from seven countries. We did not observe any alleles with amino acid mutations indicative of resistance, and of 40 point mutations there were only four non-synonymous mutations all of which were singletons. Estimated effective population sizes are an order of magnitude lower than those from another nematode species in which benzimidazole resistance has developed (Haemonchus contortus). Both the lower diversity and reduced population sizes suggest that benzimidazole resistance is likely to evolve less rapidly in Trichuris than in trichostrongyle parasites of livestock. We observed moderate levels of population subdivision (Phi(ST)=0.26) comparable with that previously observed in Ascaris lumbricoides, and identical alleles were frequently found in parasites from different continents, suggestive of recent admixture. A particularly interesting feature of the data is the high nucleotide diversities observed in nematodes from the Caribbean. This genetic complexity may be a direct result of extensive admixture and complex history of human populations in this region of the world. These data should encourage (but not make complacent) those involved in large-scale benzimidazole treatment of human intestinal nematodes.

  3. VO(acac)2 catalyzed condensation of o-phenylenediamine with aromatic carboxylic acids/aldehydes under microwave radiation affording benzimidazoles

    Institute of Scientific and Technical Information of China (English)

    Madhudeepa Dey; Krishnajyoti Deb; Siddhartha Sankar Dhar

    2011-01-01

    Vanadyl acetylacetonate, VO(acac)2, has been found to be very effective catalyst for synthesis of a variety of benzimidazoles under solvent-free condition. The methodology involves the exposure of a mixture of o-phenylenediamine and a selected aromatic carboxylic acid/aldehyde to microwave radiation without the use of any solvent or supporting agents. The benzimidazoles were obtained in quick time with high yields.

  4. 3-[1-(3-Hydroxybenzyl-1H-benzimidazol-2-yl]phenol dimethyl sulfoxide monosolvate

    Directory of Open Access Journals (Sweden)

    Magdalena Quezada-Miriel

    2012-10-01

    Full Text Available Crystals of the title compound were obtained as a 1:1 dimethyl sulfoxide solvate, C20H16N2O2·C2H6O. The molecular conformation of the organic molecule is similar to that in the previously reported unsolvated structure [Eltayeb et al. (2009. Acta Cryst. E65, o1374–o1375]. Thus, the dihedral angles formed by the benzimidazole moiety with the two benzene rings are 57.54 (4 and 76.22 (5°, and the dihedral angle between the benzene rings is 89.23 (5°. In the crystal, a three-dimensional network features O—H...O, O—H...N and O—H...S hydrogen bonds, as well as C—H...O and C—H...π interactions.

  5. Discovery and Optimization of Potent, Selective, and in Vivo Efficacious 2-Aryl Benzimidazole BCATm Inhibitors.

    Science.gov (United States)

    Deng, Hongfeng; Zhou, Jingye; Sundersingh, Flora; Messer, Jeffrey A; Somers, Donald O; Ajakane, Myriam; Arico-Muendel, Christopher C; Beljean, Arthur; Belyanskaya, Svetlana L; Bingham, Ryan; Blazensky, Emily; Boullay, Anne-Benedicte; Boursier, Eric; Chai, Jing; Carter, Paul; Chung, Chun-Wa; Daugan, Alain; Ding, Yun; Herry, Kenny; Hobbs, Clare; Humphries, Eric; Kollmann, Christopher; Nguyen, Van Loc; Nicodeme, Edwige; Smith, Sarah E; Dodic, Nerina; Ancellin, Nicolas

    2016-04-14

    To identify BCATm inhibitors suitable for in vivo study, Encoded Library Technology (ELT) was used to affinity screen a 117 million member benzimidazole based DNA encoded library, which identified an inhibitor series with both biochemical and cellular activities. Subsequent SAR studies led to the discovery of a highly potent and selective compound, 1-(3-(5-bromothiophene-2-carboxamido)cyclohexyl)-N-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamide (8b) with much improved PK properties. X-ray structure revealed that 8b binds to the active site of BACTm in a unique mode via multiple H-bond and van der Waals interactions. After oral administration, 8b raised mouse blood levels of all three branched chain amino acids as a consequence of BCATm inhibition. PMID:27096045

  6. 2-(Thiophen-2-yl-1-(thiophen-2-ylmethyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    David K. Geiger

    2012-02-01

    Full Text Available In the title compound, C16H12N2S2, the thiophene groups are rotationally disordered over two sets of sites, by approximately 180°, with occupancy ratios of 0.916 (2:0.084 (2 and 0.903 (2:0.097 (2. The major components of the thiophene and methylene substituted thiophene rings are canted by 24.06 (12 and 85.07 (10°, respectively, from the benzimidazole ring system plane and the dihedral angle between the major component thiophene ring planes is 84.90 (14°. In the crystal, there is a weak C—H...N hydrogen bond which links molecules into chains.

  7. Crystal structure of 2-(4-chloro-3-fluorophenyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    M. S. Krishnamurthy

    2015-06-01

    Full Text Available In the title compound, C13H8ClFN2, the dihedral angle between the plane of the benzimidazole ring system (r.m.s. deviation = 0.022 Å and the benzene ring is 26.90 (8°. The F atom at the meta position of the benzene ring is disordered over two sites in a 0.843 (4:0.157 (4 ratio. In the crystal, molecules are linked by N—H...N hydrogen bonds, forming infinite C(4 chains propagating along [010]. In addition, weak C—H...π and π–π interactions [shortest centroid–centroid separation = 3.6838 (12 Å] are observed, which link the chains into a three-dimensional network.

  8. 4-(1H-Benzimidazol-2-ylmethoxy-3-methoxybenzaldehyde tetrahydrate

    Directory of Open Access Journals (Sweden)

    Jerry P. Jasinski

    2011-08-01

    Full Text Available In the title compound, C16H14N2O3·4H2O, the dihedral angle between the mean planes of the benzimidazole ring system and benzene ring is 2.9 (1°. The aldehyde group is disordered over two sets of sites with refined occupancies of 0.559 (4 and 0.441 (4. In the crystal, extensive intermolecular O—H...O, O—H...N and N—H...O hydrogen bonds in concert with weak π–π stacking interactions [centroid–centroid distances = 3.6104 (9, 3.6288 (9 and 3.9167 (10 Å] create a three-dimensional network.

  9. Composite membranes based on a novel benzimidazole grafted PEEK and SPEEK for fuel cells

    Energy Technology Data Exchange (ETDEWEB)

    Li, Hongtao; Zhang, Gang; Ma, Wenjia; Zhao, Chengji; Zhang, Yang; Han, Miaomiao; Zhu, Jing; Liu, Zhongguo; Wu, Jing; Na, Hui [Alan G MacDiarmid Institute, College of Chemistry, Jilin University, Changchun 130012 (China)

    2010-10-15

    Poly(ether ether ketone) (PEEK) and sulfonated poly(ether ether ketone) (SPEEK, IEC = 2.07 mequiv.g{sup -1}) have been synthesized via nucleophilic aromatic substitution reaction. Bromomethylated poly(ether ether ketone) (PEEK-Br) is then prepared and reacted with 2-benzimidazolethiol to obtain the benzimidazole grafted poly(ether ether ketone) (PEEK-BI). The structures of PEEK-Br and PEEK-BI are characterized by {sup 1}H NMR spectra. Composite membranes based on SPEEK and PEEK-BI are prepared and their properties used for fuel cells are studied in detail. The results show that the composite membranes exhibit greatly improved mechanical properties as well as reduced water uptake and methanol permeability compared with the pristine SPEEK membrane. The increased oxidative stability and selectivity indicate that the composite membranes are promising to be used as proton exchange membranes. (author)

  10. Aggregation induced enhanced emission of 2-(2'-hydroxyphenyl)benzimidazole.

    Science.gov (United States)

    Malakar, Ashim; Kumar, Manishekhar; Reddy, Anki; Biswal, Himadree T; Mandal, Biman B; Krishnamoorthy, G

    2016-07-01

    In this study, the aggregation induced emission enhancement (AIEE) of 2-(2'-hydroxyphenyl)benzimidazole (HPBI) is reported. To investigate the AIEE process of HPBI, absorption/fluorescence spectroscopy, fluorescence imaging and field emission scanning electron microscopy were employed. A comparative study with 2-phenylbenzimidazole (PBI) divulges the significance of the hydroxyl group in the AIEE process. Further, molecular dynamics simulations have been carried out with explicit solvent molecules to follow the aggregation process of HPBI with time. The obtained molecular dynamics simulation results not only predicted the formation of aggregates but also provided detailed insight and information on the molecular interactions. The cellular studies showed aggregates yield higher fluorescence in the visible region inside HeLa cells in comparison to monomeric compounds which failed to exhibit any visible fluorescence inside the cell. The obtained aggregates were further found to be biocompatible and therefore can be used for bio-imaging applications. PMID:27334264

  11. 2-Methyl-5-nitro-1H-benzimidazol-6-amine dihydrate

    Directory of Open Access Journals (Sweden)

    Sebla Dinçer

    2011-09-01

    Full Text Available The title benzimidazole molecule, C8H8N4O2·2H2O, is planar with a maximum deviation of 0.079 (2 Å (for one of the O atoms in the nitro group. It crystallized as a dihydrate and intermolecular O—H...O and N—H...O hydrogen bonds link the uncoordinated water molecules, and the nitro and amine groups, respectively. In the crystal, N—H...O, O—H...N, O—H...O and C—H...O hydrogen bonds link the molecules to form a three-dimensional network. A π–π contact between the benzene rings, [centroid–centroid distance = 3.588 (1 Å] may further stabilize the crystal structure.

  12. Crystal structure, thermal and optical properties of Benzimidazole benzimidazolium picrate crystal

    Science.gov (United States)

    Jagadesan, A.; Peramaiyan, G.; Srinivasan, T.; Kumar, R. Mohan; Arjunan, S.

    2016-02-01

    A new organic framework of benzimidazole with picric acid has been synthesized. A single crystal with a size of 38×10×4 mm3 was grown by a slow evaporation solution growth technique. X-ray diffraction study revealed that the BZP crystal belongs to triclinic system with space group P-1. High resolution X-ray diffraction study shows the absence of grain boundaries without any defects. The thermal stability and specific heat capacity of BZP were investigated by TG/DT and TG/DSC analyses. From the UV-vis-NIR spectral study, optical transmission window and band gap of BZP were found out. The nonlinear refractive index (n2) and third order susceptibility Re(χ(3)) values of BZP crystal are estimated to be 1.73×10-7 cm2/W and 1.26×10-5 esu, respectively using a Z-scan technique.

  13. Efficient fluorescent deep-blue and hybrid white emitting devices based on carbazole/benzimidazole compound

    KAUST Repository

    Yang, Xiaohui

    2011-07-28

    We report the synthesis, photophysics, and electrochemical characterization of carbazole/benzimidazole-based compound (Cz-2pbb) and efficient fluorescent deep-blue light emitting devices based on Cz-2pbb with the peak external quantum efficiency of 4.1% and Commission Internationale dÉnclairage coordinates of (0.16, 0.05). Efficient deep-blue emission as well as high triplet state energy of Cz-2pbb enables fabrication of hybrid white organic light emitting diodes with a single emissive layer. Hybrid white emitting devices based on Cz-2pbb show the peak external quantum efficiency exceeding 10% and power efficiency of 14.8 lm/W at a luminance of 500 cd/m2. © 2011 American Chemical Society.

  14. A general method for tritium labelling of benzimidazole carbamates by catalytic exchange in dioxane solutions

    Energy Technology Data Exchange (ETDEWEB)

    Lacey, E. (Commonwealth Scientific and Industrial Research Organization, Glebe, NSW (Australia). Div. of Animal Health, McMaster Lab.); Dawson, M. (Sydney Univ. (Australia). Dept. of Pharmacy); Long, M.A.; Than, C. (New South Wales Univ., Kensington (Australia). School of Chemistry)

    1989-12-01

    Benzimidazole carbamates (BZCs) act as inhibitors of the tubulin-microtubule equilibria in eukaryotic organisms. Recently drug resistance to this class of compounds in helminth parasites has been shown to be due to a reduced ability of resistant tubulin to bind BZCs. In order to quantitate the nature of the tubulin-BZC interaction a general method for the specific tritium labelling of BZCs has been developed. The BZCs: mebendazole, oxfendazole, parbendazole, oxibendazole, albendazole and fenbendazole were labelled by catalytic exchange using palladium on calcium carbonate in pure dioxane at 60{sup 0}C under tritium gas. The position of label incorporation for tritiated albendazole was determined by tritium-NMR as the 4-position of benzimadazole nucleus. The yields for individual BZCs varied from 8 to 68% for a range of specific activity of 0.44 to 13.4 Ci/mmole. (author).

  15. 1-(4-Bromobenzyl-2-(4-bromophenyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Hua-Jun Ma

    2014-05-01

    Full Text Available There are two molecules in the asymmetric unit of the title compound, C20H14Br2N2. In the first, the dihedral angles between the mean plane of the benzimidazole group and those of the 4-bromobenzyl and 4-chlorophenyl groups are 50.72 (17 and 71.29 (16°, respectively, while the corresponding angles in the second molecule are 42.09 (16 and 89.05 (17°. The 4-bromobenzyl and 4-bromophenyl groups make an angle of 68.1 (2 and 85.1 (21° with each other in the two molecules. In the crystal, weak C—H...N and C—H...Br hydrogen bonds link the molecules along the c-axis direction. Br...Br interactions [3.5733 (9Å] are also observed.

  16. HPLC method for identification and quantification of benzimidazole derivatives in antiparasitic drugs.

    Science.gov (United States)

    Kulik, Anna; Białecka, Wanda; Podolska, Marzena; Kwiatkowska-Puchniarz, Barbara; Mazurek, Aleksander

    2011-01-01

    The subject of the study was to develop a versatile HPLC system for identification and determination of four benzimidazole derivatives in the antiparasitic drugs. The tests covered: Zentel, Panacur, Vermox tablets and Systamex suspension. A satisfactory separation was obtained using the Nucleosil C8 column in the gradient system composed of mobile phase A: 85% orthophosphoric acid / water / acetonitrile in 0.05:75:25, v/v/v ratio, and mobile phase B: 85% orthophosphoric acid / water / acetonitrile in 0.05:50:50, v/v/v ratio. Both phases were adjusted to pH = 4.5 with 15% sodium hydroxide solution. A detection at 288 nm for oxfendazole and 254 nm for albendazole, fenbendazole and mebendazole was applied. The correlation coefficients in the range 0,9997 - 0,9999 proved that the calibration curves were linear. The method was validated in terms of selectivity, accuracy and precision. PMID:22125945

  17. Synthesis and biological activity of some heterocyclic compounds containing benzimidazole and beta-lactam moiety

    Indian Academy of Sciences (India)

    K F Ansari; C Lal

    2009-11-01

    A number of 1-substituted-2-methyl benzimidazole derivatives have been synthesized and tested for their antibacterial activities. The chemical structures of the newly synthesized compounds were verified on the basis of spectral and elemental methods of analyses. Investigation of antimicrobial activity of the compounds was done by disc diffusion method using Gram-positive (S. aureus, S. mutans and B. subtilis), Gram-negative (E. coli, S. typhi and P. aeruginosa) bacteria and fungi (C. albicans, A. flavus and A. niger). Among the compounds tested 5a, 5b, 5d, 5i, 5j and 5k exhibited good antibacterial activities against Gram positive bacteria, while 5d and 5i also showed notable antifungal activity. Specially compounds 5a and 5b exhibited appreciable activity against S. aureus and B. subtilis comparable to reference drugs.

  18. Solubility improvement of an anthelmintic benzimidazole carbamate by association with dendrimers

    Energy Technology Data Exchange (ETDEWEB)

    Fernandez, L.; Sigal, E.; Santo, M., E-mail: msanto@exa.unrc.edu.ar [Departamento de Fisica, Facultad de Ciencias Exactas Fisicoquimicas y Naturales, Universidad Nacional de Rio Cuarto (Argentina); Otero, L.; Silber, J. J. [Departamento de Quimica. Facultad de Ciencias Exactas Fisicoquimicas y Naturales, Universidad Nacional de Rio Cuarto, Rio Cuarto (Argentina)

    2011-10-15

    The improvement of aqueous solubility of methyl (5-[propylthio]-1H-benzimidazole-2-yl) carbamate, albendazole (ABZ) using polyamidoamine (PAMAM) dendrimers as solubility enhancers was investigated. Full generation PAMAM dendrimers with amine terminal groups, (G3), with hydroxyl terminal groups (G3OH) and half generation PAMAM dendrimers with carboxylate terminal groups (G2.5 and G3.5), were chosen for this study. The nature of dendrimer-ABZ association was investigated by UV absorption, fluorescence emission measurements and by {sup 1}H-NMR spectroscopy. The results obtained show that these polymeric structures have the capacity to enhance the solubility of ABZ, both lipophilic and specific hydrogen bond interactions contributing to the guest-host association. Although all studied dendrimers have hydrophobic internal nanoenvironments with similar dimensions, their surfaces differ significantly and the nature and the localization of the interactions involved in ABZ-dendrimer association depend on the type of terminal groups. (author)

  19. Crystal structures of HIV-1 nonnucleoside reverse transcriptase inhibitors: N-benzyl-4-methyl-benzimidazoles

    Science.gov (United States)

    Ziółkowska, Natasza E.; Michejda, Christopher J.; Bujacz, Grzegorz D.

    2009-07-01

    HIV-1 nonnucleoside reverse transcriptase inhibitors are potentially specific and effective drugs in AIDS therapy. The presence of two aromatic systems with an angled orientation in the molecule of the inhibitor is crucial for interactions with HIV-1 RT. The inhibitor drives like a wedge into the cluster of aromatic residues of RT HIV-1 and restrains the enzyme in a conformation that blocks the chemical step of nucleotide incorporation. Structural studies provide useful information for designing new, more active inhibitors. The crystal structures of four NNRTIs are presented here. The investigated compounds are derivatives of N-benzyl-4-methyl-benzimidazole with various aliphatic and aromatic substituents at carbon 2 positions and a 2,6-dihalogeno-substituted N-benzyl moiety. Structural data reported here show that the conformation of the investigated compounds is relatively rigid. Such feature is important for the nonnucleoside inhibitor binding to HIV-1 reverse transcriptase.

  20. 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.

  1. The effectiveness of benzimidazole derivatives for the treatment and prevention of histomonosis (blackhead) in turkeys.

    Science.gov (United States)

    Hegngi, F N; Doerr, J; Cummings, T S; Schwartz, R D; Saunders, G; Zajac, A; Larsen, C T; Pierson, F W

    1999-02-01

    The benzimidazole derivatives, albendazole and fenbendazole were evaluated for their effectiveness in the treatment and prevention of histomonosis (blackhead) in turkeys. Histomonosis was produced in 5 week-old birds by placing them on broiler breeder litter known to be contaminated with Heterakis gallinae ova and the protozoan Histomonas meleagridis. In the first trial, at the onset of confirmed clinical disease, birds were treated orally with metronidazole, a compound known to be effective against Histomonas. Those receiving metronidazole had significantly greater mean body weight gains during the treatment period and the 2 weeks following treatment than untreated controls. Treated birds also had significantly lower caecal and liver lesion scores. These findings served to validate the method of disease reproduction and establish its suitability for testing the benzimidazoles. Similar trials were conducted to determine the therapeutic value of albendazole at 100.0 mg/kg of body weight and fenbendazole at 10.0 mg/kg body weight, administered orally twice a day for 5 consecutive days. Under these conditions, both drugs were found to be ineffective as treatments. A final trial was conducted to assess the prophylactic value of albendazole and fenbendazole administration. At the time of placement on contaminated litter, birds were medicated as previously described with the exception that treatment was continued for 14 consecutive days, the approximate incubation period for histomonosis. The trial was terminated on the 16th day. In the case of both albendazole and fenbendazole, treatment was associated with a significant increase in mean body weight gain and lower caecal and liver lesion scores. It is believed that the observed prophylactic effect may be attributed to the destruction of the transport vector e.g., Heterakis larvae, or to direct killing of the flagellated form of Histomonas which is normally found in the caecal lumen and is considered to be more sensitive

  2. Activation of peroxyl and molecular oxygen using bis-benzimidazole diamide copper (II) compounds

    Indian Academy of Sciences (India)

    Pavan Mathur

    2006-11-01

    New tetradentate bis-benzimidazole ligands have been synthesized and utilized to prepare copper (II) complexes. Some of these copper (II) complexes have been characterized structurally. The copper (II) in these complexes is found to possess varying geometries. A distorted octahedral geometry is found with a highly unsymmetrical bidentate nitrate group. An unusual polymeric one-dimensional structure is observed where copper (II) is in a distorted square pyramidal geometry with a monodentate nitrate ion, having long Cu-O bond, while a distorted triagonal bipyramidal geometry is found with two carbonyl O atoms and a Cl atom in the equatorial plane, and two benzimidazole imine N atoms occupy the axial position. These compounds are found to activate the cumylperoxyl group, and this has been utilized in the facile oxidation of aromatic alcohols to aldehydes, where they act as catalysts with large turnovers. The yields of the respective products vary from 32 to 65%. The role of molecular oxygen has been studied and an attempt has been made to identify the "active copper species”. Activation of molecular oxygen has also been observed and has been used for oxidative dealkylation of a hindered phenol, producing di-butyl quinones with yields of 20-25% and 10-12 fold catalytic turnover. Dihydroxybenzenes and substituted catechols are also readily oxidized to the corresponding quinones, in oxygen-saturated solvents. Yields of 84% have been observed with 34-fold catalyst turnover, with di--butylcatechol. The activity of these copper (II) - bis-benzmidazolediamide compounds is reminiscent of the functioning of copper centres in galactose oxidase, tyrosinase and catechol oxidase.

  3. 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.

  4. 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.

  5. Synthesis and Biological Evaluation of Novel Benzimidazole Derivatives Bearing a Heterocyclic Ring at 4/5 Position

    Energy Technology Data Exchange (ETDEWEB)

    Wubulikasimu, Reyila; Yang, Yanbing; Xue, Fei; Luo, Xianjin; Shao, Dongping [Shanghai Jiaotong Univ., Shanghai (China); Li, Yuhuan; Gao, Rongmei [Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing (China); Ye, Weidong [Zhejiang Medicine Co. Ltd., Zhejiang (China)

    2013-08-15

    A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 (IC{sub 50} = 1.08 μg/mL, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.

  6. Synthesis of some benzimidazole derivatives endowed with 1,2,3-triazole as potential inhibitors of hepatitis C virus.

    Science.gov (United States)

    Youssif, Bahaa G M; Mohamed, Yaseen A M; Salim, Mohammed T A; Inagaki, Fuyuhiko; Mukai, Chisato; Abdu-Allah, Hajjaj H M

    2016-06-01

    New derivatives of 2-thiobenzimidazole incorporating triazole moiety were synthesized, characterized and tested in vitro for antiviral activity against hepatitis C virus (HCV) and hepatitis B virus (HBV). Their cytotoxicity was determined by the reduction in the number of viable cell. All of the synthesized compounds are inactive against HBV and some showed activity against HCV. In particular, two compounds showed significant activity, 2-{4-[(1-benzoylbenzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitro-phenyl)-acetamide (13) and 2-(4-{[1-(p-chlorobenzoyl)-benzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitrophenyl)-acetamide (17). The results give an insight into the importance of the substituent at position 2 of benzimidazole for the inhibition of HCV. PMID:27279065

  7. One step synthesis of pyrido[1,2-α]benzimidazole derivatives of aryloxypyrazole and their antimicrobial evaluation

    Institute of Scientific and Technical Information of China (English)

    Hardik H.Jardosh; Chetan B.Sangani; Manish P.Patel; Ranjan G.Patel

    2013-01-01

    A new series of pyrido[1,2-α]benzimidazole derivatives bearing the aryloxypyrazole nucleus have been synthesized by base-catalyzed cyclocondensation reaction through multi-component reaction (MCR) approach.All the synthesized compounds were investigated against a representative panel of pathogenic strains using broth microdilution minimum inhibitory concentration (MIC) method for their in vitro antimicrobial activity.Reviewing the data,majority of the compounds were found to be active against employed pathogens.SAR study explores that antimicrobial activity is strongly depends on the nature of the substituents at the ether linked aryl ring attached to the pyrazole unit,together with the substituent present on the C5 of the benzimidazole unit.

  8. A spectrophotometric study of the protonation processes of some N-[1-(benzimidazol-1-yl]methylbenzamide derivatives

    Directory of Open Access Journals (Sweden)

    NADA U. PERISIC-JANJIC

    2000-01-01

    Full Text Available The protonation of N-[1-(benzimidazol-1-yl]methylbenzamide derivatives in aqueous acids (H2SO4 media was investigated, using a spectrophotometric method. The investigated compounds have two protonation processes. The first protonation process occurs in weakly acidic aqueous solutions (pH range and refers to the protonation of the benzimidazole part of the molecule. The second protonation process occurs in concentrated sulfuric acid solutions and refers to protonation of the amide group. The protonation constants of the second process were calculated by the Hammett and Cox-Yates method. The effect of chemical structure on the ionisation constants is discussed. A correlation between the protonation constants and antimicrobial activity was established.

  9. Synthesis of benzimidazole based thiadiazole and carbohydrazide conjugates as glycogen synthase kinase-3β inhibitors with anti-depressant activity.

    Science.gov (United States)

    Khan, Imran; Tantray, Mushtaq A; Hamid, Hinna; Alam, Mohammad Sarwar; Kalam, Abul; Dhulap, Abhijeet

    2016-08-15

    A series of benzimidazole based thiadiazole and carbohydrazide conjugates have been synthesized and evaluated for inhibition of glycogen synthase kinase-3β and anti-depressant effect. Compounds 4f, 4j, 5b, 5g and 5i were found to be the most potent inhibitors of GSK-3β in vitro amongst the twenty-five benzimidazole based thiadiazole and carbohydrazide conjugates synthesized. Compound 5i was also found to exhibit significant antidepressant activity in vivo at 50mg/kg, when compared to fluoxetine, a known antidepressant drug. The molecular docking studies revealed multiple hydrogen bond interactions by the synthesized compounds with various amino acid residues, viz, ASP-133, LYS-183, PRO-136, VAL-135, TYR-134, or LYS-60 at the GSK-3β receptor site. PMID:27406796

  10. Design, synthesis and biological evaluation of 5-fluorouracil-derived benzimidazoles as novel type of potential antimicrobial agents.

    Science.gov (United States)

    Fang, Xue-Jie; Jeyakkumar, Ponmani; Avula, Srinivasa Rao; Zhou, Qian; Zhou, Cheng-He

    2016-06-01

    A series of 5-fluorouracil benzimidazoles as novel type of potential antimicrobial agents were designed and synthesized for the first time. Bioactive assay manifested that some of the prepared compounds exhibited good or even stronger antibacterial and antifungal activities against the tested strains in comparison with reference drugs norfloxacin, chloromycin and fluconazole. Noticeably, 3-fluorobenzyl benzimidazole derivative 5c gave remarkable antimicrobial activities against Saccharomyces cerevisiae, MRSA and Bacillus proteus with MIC values of 1, 2 and 4μg/mL, respectively. Experimental research revealed that compound 5c could effectively intercalate into calf thymus DNA to form compound 5c-DNA complex which might block DNA replication and thus exert antimicrobial activities. Molecular docking indicated that compound 5c should bind with DNA topoisomerase IA through three hydrogen bonds by the use of fluorine atom and oxygen atoms in 5-fluorouracil with the residue Lys 423. PMID:27117429

  11. 1-Benzyl-2-Phenylbenzimidazole (BPB, a Benzimidazole Derivative, Induces Cell Apoptosis in Human Chondrosarcoma through Intrinsic and Extrinsic Pathways

    Directory of Open Access Journals (Sweden)

    Ju-Fang Liu

    2012-12-01

    Full Text Available In this study, we investigated the anticancer effects of a new benzimidazole derivative, 1-benzyl-2-phenyl -benzimidazole (BPB, in human chondrosarcoma cells. BPB-mediated apoptosis was assessed by the MTT assay and flow cytometry analysis. The in vivo efficacy was examined in a JJ012 xenograft model. Here we found that BPB induced apoptosis in human chondrosarcoma cell lines (JJ012 and SW1353 but not in primary chondrocytes. BPB induced upregulation of Bax, Bad and Bak, downregulation of Bcl-2, Bid and Bcl-XL and dysfunction of mitochondria in chondrosarcoma. In addition, BPB also promoted cytosolic releases AIF and Endo G. Furthermore, it triggered extrinsic death receptor-dependent pathway, which was characterized by activating Fas, FADD and caspase-8. Most importantly, animal studies revealed a dramatic 40% reduction in tumor volume after 21 days of treatment. Thus, BPB may be a novel anticancer agent for the treatment of chondrosarcoma.

  12. Structure of HIV-1 nonnucleoside reverse transcriptase inhibitors derivatives of N-benzyl-benzimidazole with different substituents in position 4

    Science.gov (United States)

    Ziółkowska, Natasza E.; Michejda, Christopher J.; Bujacz, Grzegorz D.

    2010-01-01

    The constant development of new drugs against HIV-1 is necessary due to global expansion of AIDS and HIV-1 drug resistance. Nonnucleoside reverse transcriptase inhibitors of HIV-1 (NNRTIs) are potentially effective and nontoxic drugs in AIDS therapy. The crystal structures of six nonnucleoside inhibitors of HIV-1 reverse transcriptase (RT) derivatives of N-benzyl-benzimidazole are reported here. The investigated compounds belong to the group of so called "butterfly like" inhibitors with characteristic two π-electron moieties with an angled orientation. The structural data show the influence of the substituents of the benzimidazole ring on the geometry of the molecule and correlation between the structure of the inhibitor and its biological activity.

  13. 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)].

  14. Synthesis and properties of poly(aryl sulfone benzimidazole) and its copolymers for high temperature membrane electrolytes for fuel cells

    DEFF Research Database (Denmark)

    Yang, Jingshuai; Li, Qingfeng; Cleemann, Lars Nilausen;

    2012-01-01

    Poly(aryl sulfone benzimidazole) (SO2PBI) and its copolymers with poly[2,2′-p-(phenylene)-5,5′-bibenzimidazole] (pPBI), termed as Co-SO2PBI, were synthesized with varied feeding ratios of 4,4′-sulfonyldibenzoic acid (SDBA) to terephthalic acid (TPA). Incorporation of the stiff para-phenylene and ......Poly(aryl sulfone benzimidazole) (SO2PBI) and its copolymers with poly[2,2′-p-(phenylene)-5,5′-bibenzimidazole] (pPBI), termed as Co-SO2PBI, were synthesized with varied feeding ratios of 4,4′-sulfonyldibenzoic acid (SDBA) to terephthalic acid (TPA). Incorporation of the stiff para...

  15. Two thiazolylindoles and a benzimidazole: novel compounds on the designer drug market with potential cannabinoid receptor activity.

    Science.gov (United States)

    Westphal, Folker; Sönnichsen, Frank D; Knecht, Siegfried; Auwärter, Volker; Huppertz, Laura

    2015-04-01

    In a seizure of German customauthorities two 3-([1,3]-thiazol-2-yl)indoles (N-(2-methoxyethyl),N-iso-propyl-2-(1-pentyl-1H-indol-3-yl)-4-thiazolemethanamine (1) and N,N-diethyl-2-(1-pentyl-1H-indol-3-yl)-4-thiazolemethanamine (2)) and one benzimidazole (1-(cyclohexylmethyl)-2-[(4-ethoxyphenyl)methyl]-N,N-diethyl-1H-benzimidazole-5-carboxamide (6)) were seized as pure compounds. The compounds have been detected in Germany for the first time, and no analytical data had been previously published. Mass spectrometric (MS), infrared (IR) spectroscopic, and nuclear magnetic resonance (NMR) spectroscopic data are presented and the way of the structure elucidation of these rather uncommon compounds is discussed.

  16. Two proton-conductive hybrids based on 2-(3-pyridyl)benzimidazole molecules and Keggin-type heteropolyacids

    Energy Technology Data Exchange (ETDEWEB)

    Wei, Mei-Lin, E-mail: weimeilinhd@163.com; Wang, Yu-Xia; Wang, Xin-Jun

    2014-01-15

    Two proton-conductive organic/inorganic complexes were constructed by Keggin-type heteropolyacids and 2-(3-pyridyl)benzimidazole molecules. Single-crystal X-ray diffraction analyses revealed that two complexes crystallized in the monoclinic space group P2{sub 1}/c, exhibited different unit cell parameters, and presented different hydrogen-bonded networks constructed by 2-(3-pyridyl)benzimidazole molecules, [PMo{sub 12}O{sub 40}]{sup 3−} anions and solvent molecules. The results of thermogravimetric analyses suggest that two supramolecular complexes have different thermal stability based on the different hydrogen-bonded networks. Two complexes at 100 °C under 35–98% relative humidity showed a good proton conductivity of about 10{sup −3} S cm{sup −1}. The proton conductivities of two complexes under 98% relative humidity both increase on a logarithmic scale with temperature range from 25 to 100 °C. At 100 °C, both complexes showed poor proton conductivities of 10{sup −8}–10{sup −9} S cm{sup −1} under acetonitrile or methanol vapor. - Graphical abstract: Two molecular hybrids constructed by Keggin-type heteropolyacids and 2-(3-pyridyl)benzimidazole molecules showed good proton conductivities of 10{sup −3} S cm{sup −1} at 100 °C under 35–98% relative humidity. Display Omitted - Highlights: • 2-(3-Pyridyl)benzimidazole could form hydrogen bonds via the N–H groups. • Heteropolyacids have suitable characteristics to be used excellent proton conductors. • Two proton-conductive hybrids based on Keggin HPAs and 3-PyBim were constructed. • The structures were determined by using single-crystal X-ray diffraction data. • They showed good proton conductivities of 10{sup −3} S cm{sup −1} at 100 °C under 35–98% RH.

  17. Glyoxylic acid as catalyst: A simple selective synthesis of 1,2-disubstituted benzimidazoles in aqueous media

    Institute of Scientific and Technical Information of China (English)

    Shivaji S. Pawar; Deepak V. Dekhane; Murlidhar S. Shingare; Shivaji N. Thore

    2008-01-01

    Glyoxylic acid (5 tool%) performs as a novel highly water-soluble catalyst for the synthesis of 2-aryl-l-arylmethyl-lH-benzimidazoles from a wide range of substituted o-phenylenediamines and various substituted aldehydes in good to excellent isolated yields (85-95%) using water as solvent at ambient temperature. The remarkable advantages offered by this method are easily and inexpensive available catalyst, simple procedure, mild conditions, much faster (20-40 min) reactions and excellent yields of products.

  18. Effect of two formulations of benzimidazole carbamates on the viability of cysts of Echinococcus granulosus in vivo

    OpenAIRE

    Daniel-Mwuambete K.; Ponce-Gordo F.; Torrado J.; Torrado S.; Cuesta-Bandera C.

    2003-01-01

    Two different preparations, solution and suspension, of three benzimidazole carbamate drugs, mebendazole, albendazole and ricobendazole, were compared by analyzing their in vivo activity against Echinococcus granulosus cysts in a mouse model. Polyvinylpyrrolidone was used for the elaboration of drug solutions and these formulations manifested better results in terms of reduction of number of viable hydatid cysts in mice than the reference drug suspensions. The effect was more prominent on meb...

  19. 3D QSAR AND PHARMACOPHORE IDENTIFICATION OF ISOQUINOLINE AND BENZIMIDAZOLE ANALOGS AS POTENT C-RAF INHIBITORS

    OpenAIRE

    Blessy Christina N*, Manoj Kumar Mahto, Uday Kumar Dasari and Matcha Bhaskar

    2013-01-01

    The C-Raf inhibitors obstruct the activity of other signaling pathways which are implicated in many tumors. Hence C-RAF inhibition has emerged as a promising therapeutic target for many cancers. A series of 33 novel Isoquinoline and benzimidazole derivatives has been reported as C-RAF inhibitors. A combined study of pharmacophore prediction, atom based 3d QSAR and molecular docking explored the structural insights of these inhibitors. A Five point pharmacophore hypothesis AADHR.  719 yielded ...

  20. 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.

  1. Improvement of surface wettability and interfacial adhesion of poly-(p-phenylene terephthalamide) by incorporation of the polyamide benzimidazole segment

    Energy Technology Data Exchange (ETDEWEB)

    Cai Renqin [State key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065 (China); Peng Tao [State key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065 (China); China Blue Star Chengrand Chemical Co. Ltd., Chengdu, 610041 (China); Wang Fengde [China Blue Star Chengrand Chemical Co. Ltd., Chengdu, 610041 (China); Ye Guangdou [State key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065 (China); Xu Jianjun, E-mail: xujj@scu.edu.cn [State key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065 (China)

    2011-09-01

    In order to investigate the effect of the polyamide benzimidazole group on the surface wettability and interfacial adhesion of fiber/matrix composites, surface features of two kinds of aramid fibers, poly (p-phenylene terephthalamide) fiber (Kevlar-49) and poly-(polyamide benzimidazole-co-p-phenylene terephthalamide) (DAFIII), have been analyzed by X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM) and contact angle analysis (CAA) system, respectively. The results show that with the incorporation of the polyamide benzimidazole segment, more polar functional groups exist on DAFIII surface. The contact angles of water and diiodomethane on DAFIII surface get smaller. The surface free energy of DAFIII increases to 36.5 mJ/m{sup 2}, which is 2.3% higher than that of Kevlar-49. In addition, DAFIII has a larger rough surface compared with that of Kevlar-49 due to different spinning processes. The interfacial shear strength (IFSS) of DAFIII/matrix composite is 25.7% higher than that of Kevlar-49/matrix composite, in agreement with the observed results from surface feature tests. SEM micrographs of failed micro-droplet specimens reveal a strong correlation between the fracture features and the observed test data.

  2. Organic-inorganic hybrid proton exchange membrane based on polyhedral oligomeric silsesquioxanes and sulfonated polyimides containing benzimidazole

    Science.gov (United States)

    Pan, Haiyan; Zhang, Yuanyuan; Pu, Hongting; Chang, Zhihong

    2014-10-01

    A new series of organic-inorganic hybrid proton exchange membranes (PEMs) were prepared using sulfonated polyimides containing benzimidazole (SPIBIs) and glycidyl ether of polyhedral oligomeric silsesquioxanes (G-POSS). SPIBIs were synthesized using 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTDA), 5-amino-2-(4-aminophenyl) benzimidazole (APBIA) and 4,4‧-diaminodiphenyl ether-2,2‧-disulfonic acid (ODADS). The organic-inorganic cross-linked membranes can be prepared by SPIBIs with G-POSS by a thermal treatment process. The cross-linking density of the membranes was evaluated by gel fractions. The water uptake, swelling ratio, mechanical property, thermal behavior, proton conductivity, oxidative and hydrolytic stability of the cross-linked organic-inorganic membranes were intensively investigated. All the cross-linked membranes exhibit high cross-linking density for the gel fraction higher than 70%. Compared to pristine membranes (SPIBIs) and membranes without benzimidazole groups (SPI), the anti-free-radical oxidative and hydrolytic stabilities of cross-linked membranes are significantly higher. The anti-free-oxidative stability of SPIBI-100-P (cross-linked SPIBI membrane with 100% degree of sulfonation) is nearly four-fold higher than that of SPIBI-100. The proton conductivity of the cross-linked membranes ranges from 10-3 S cm-1 to 10-2 S cm-1 depending both on the degree of sulfonation (DS) of the SPIBI and temperature.

  3. Alternative energy production pathways in Taenia crassiceps cysticerci in vitro exposed to a benzimidazole derivative (RCB20).

    Science.gov (United States)

    Fraga, Carolina Miguel; Da Costa, Tatiane Luiza; De Castro, Ana Maria; Reynoso-Ducoing, Olivia; Ambrosio, Javier; Hernández-Campos, Alicia; Castillo, Rafael; Vinaud, Marina Clare

    2016-04-01

    Biochemical studies of benzimidazole derivatives are important to determine their mode of action and activity against parasites. The lack of antihelminthic alternatives to treat parasitic infections and albendazole resistance cases make the search for new antiparasitary drugs of utmost importance. The 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole (RCB20) is a benzimidazole derivative with promising effect. This study evaluated the effect of different concentrations of RCB20 in the alternative energetic pathway of in vitro Taenia crassiceps cysticerci. The parasites were in vitro exposed to 6.5 and 13 µM of RCB20 and albendazole sulfoxide (ABZSO). The quantification of acetate, acetoacetate, β-hydroxybutyrate, fumarate and propionate was performed by high-performance liquid chromatography. The quantification of urea, creatinine and total proteins was performed by spectrophotometry. The increase in β-hydroxybutyrate reflects the enhancement of the fatty acid oxidation in the treated groups. Volatile fatty acids secretion, acetate and propionate, was increased in the treated groups. The secretion mechanisms of the treated parasites were impaired due to organic acids increased concentrations in the cysticerci. It is possible to conclude that the metabolic effect on alternative energetic pathways is slightly increased in the parasites treated with RCB20 than the ones treated with ABZSO.

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

    Science.gov (United States)

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

    2011-03-21

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

  5. Improvement of surface wettability and interfacial adhesion of poly-(p-phenylene terephthalamide) by incorporation of the polyamide benzimidazole segment

    Science.gov (United States)

    Cai, Ren-Qin; Peng, Tao; Wang, Feng-De; Ye, Guang-Dou; Xu, Jian-Jun

    2011-09-01

    In order to investigate the effect of the polyamide benzimidazole group on the surface wettability and interfacial adhesion of fiber/matrix composites, surface features of two kinds of aramid fibers, poly (p-phenylene terephthalamide) fiber (Kevlar-49) and poly-(polyamide benzimidazole-co-p-phenylene terephthalamide) (DAFIII), have been analyzed by X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM) and contact angle analysis (CAA) system, respectively. The results show that with the incorporation of the polyamide benzimidazole segment, more polar functional groups exist on DAFIII surface. The contact angles of water and diiodomethane on DAFIII surface get smaller. The surface free energy of DAFIII increases to 36.5 mJ/m 2, which is 2.3% higher than that of Kevlar-49. In addition, DAFIII has a larger rough surface compared with that of Kevlar-49 due to different spinning processes. The interfacial shear strength (IFSS) of DAFIII/matrix composite is 25.7% higher than that of Kevlar-49/matrix composite, in agreement with the observed results from surface feature tests. SEM micrographs of failed micro-droplet specimens reveal a strong correlation between the fracture features and the observed test data.

  6. Electrochemical and theoretical studies on the synergistic interaction and corrosion inhibition of alkyl benzimidazoles and thiosemicarbazide pair on mild steel in hydrochloric acid

    Energy Technology Data Exchange (ETDEWEB)

    Ramya, K.; Mohan, Revathi; Anupama, K.K.; Joseph, Abraham, E-mail: drabrahamj@gmail.com

    2015-01-15

    Synergistic hydrogen bonded interaction of alkyl benzimidazoles and thiosemicarbazide (TSC) and its corrosion protection properties on mild steel in hydrochloric acid at different temperatures have been studied using polarization, EIS, adsorption, surface studies and computational methods. The extent of synergistic interaction increases with temperature. Quantum chemical approach used to calculate some electronic properties of the molecules and to ascertain the synergistic interaction, inhibitive effect and molecular structures. The corrosion inhibition efficiencies and the global chemical reactivity relate to some parameters, such as total energy, E{sub HOMO}, E{sub LUMO} and gap energy (ΔE) thiosemicarbazide (TSC) interacts with benzimidazoles derivatives up to a bond length of approximately 1.99Å. This interaction represents the formation of a hydrogen bond between the thiosemicarbazide (TSC) and benzimidazoles. This synergistic interaction of thiosemicarbazide (TSC) and benzimidazole derivatives offer extended inhibition efficiency towards mild steel in hydrochloric acid. - Highlights: • Synergistic interaction between alkyl benzimidazoles and TSC has been studied. • Mechanism involves combination of physisorption and chemisorption. • The adsorption phenomenon obeys Langmuir isotherm. • Inhibition efficiency increases with temperature.

  7. Activity of benzimidazoles against Dientamoeba fragilis (Trichomonadida, Monocercomonadidae in vitro and correlation of beta-tubulin sequences as an indicator of resistance

    Directory of Open Access Journals (Sweden)

    Stark Damien

    2014-01-01

    Full Text Available Recently, Dientamoeba fragilis has emerged as a significant and common enteropathogen. The majority of patients with dientamoebiasis present with gastrointestinal complaints and chronic symptoms are common. Numerous studies have successfully demonstrated parasite clearance, coupled with complete resolution of clinical symptoms following treatment with various antiparasitic compounds. Despite this, there is very little in vitro susceptibility data available for the organism. Benzimidazoles are a class of antiparasitic drugs that are commonly used for the treatment of protozoan and helminthic infections. Susceptibility testing was undertaken on four D. fragilis clinical isolates against the following benzimidazoles: albendazole, flubendazole, mebendazole, nocodazole, triclabendazole and thiabendazole. The activities of the antiprotozoal compounds at concentrations ranging from 2 μg/mL to 500 μg/mL were determined via cell counts of D. fragilis grown in xenic culture. All tested drugs showed no efficacy. The beta-tubulin transcript was sequenced from two of the D. fragilis isolates and amino acid sequences predicted a susceptibility to benzimidazoles. This is the first study to report susceptibility profiles for benzimidazoles against D. fragilis, all of which were not active against the organism. This study also found that beta-tubulin sequences cannot be used as a reliable marker for resistance of benzimidazoles in D. fragilis.

  8. The Recent Progresses in the Synthesis of Benzimidazoles%苯并眯唑衍生物的合成研究进展

    Institute of Scientific and Technical Information of China (English)

    叶佳; 许孝良

    2012-01-01

    Benzimidazole is a heterocyclic aromatic organic compound,which consists of the fusion of benzene and imidazole. The benzimidazole ring plays a substaintial roal in modern drug progress for its unique pharmaeophore. Benzimidazole derivatives as anti-microbial and antitumor have been proved highly effectual medicament. As an important organic intermediate, benzimidazoles were used as transition metal ligands,metal surface treatment agents. Research of benzimidazoles was presented in the paper,which provided a theoretical basis for the further valuable research.%苯并咪唑类分子是含有苯环和咪唑环的杂环芳香族有机化合物,具有抗肿瘤、抗菌等多种生物活性,在药学和医学等领域有广泛的使用。同时由于其特殊的环结构和电子效应,该类衍生物是一类重要的有机合成中间体,也可用作过渡金属的配体,金属表面处理剂等。本文综述了苯并咪唑衍生物的合成方法,对国内外最新的合成工作进行讨论,为今后的研究提供帮助。

  9. Innovative restriction site created PCR-RFLP for detection of benzimidazole resistance in Teladorsagia circumcincta.

    Science.gov (United States)

    Shayan, Parviz; Eslami, Ali; Borji, Hassan

    2007-04-01

    Benzimidazole compounds, especially albendazole, are the most commonly used anthelmintics for deworming of small ruminants in Iran. It is believed that the therapeutic effects of the benzimidazoles (BZs) come through their binding capacity to the beta-tubulin isotype 1. Substitution of phenylalanine to tyrosine at position 200 of this polypeptide confers resistance to BZs. Several investigators developed different biological- and molecular-based techniques to demonstrate the occurrence of resistance in helminthes against BZs. To address the determination of resistance at position 200 of beta-tubulin isotype 1, we developed an innovative restriction site created polymerase chain reaction-restriction fragment length polymorphism, in which nucleotide A at the position of 637 upstream flanked by the first two coding sequences of the phenylalanine (TT) triplet was substituted through the nucleotide G. The introduced modification in forward primer (UTvet MF-primer) leads to the creation of restriction site (AACGTT) for PSP1. Therefore, in the case of normal allele only, PSP1 can cut the corresponding PCR product. In the first step, the genomic DNA was isolated from each single Teladorsagia circumcincta collected either from the abomasa of untreated (n = 35) or of 5 mg/kg BW 2.5% albendazole suspension-treated (n = 40) sheep. It was amplified with the primer pair, creating PCR product of 403 bp in length. In the second step, the PCR product was extracted from agarose gel and amplified with the modified forward primer (UTvet MF-primer) and the same reverse primer as in step 1, creating a PCR product of 222 bp. The PCR product was then cut with PSP1 to obtain in the case of normal allele two DNA products (183 and 39 bp). Eight of the 35 worms collected from the untreated sheep were BZ(SS) homozygotes, and the rest (27) were BZ(RS) heterozygotes. In our preliminary experiment, we could not find a BZ(RR) homozygote form within the examined samples. Five out of 40 worms

  10. Catalytic transfer hydrogenation of azobenzene by low-valent nickel complexes: a route to 1,2-disubstituted benzimidazoles and 2,4,5-trisubstituted imidazolines.

    Science.gov (United States)

    Zurita, Daniel A; Flores-Alamo, Marcos; García, Juventino J

    2016-06-21

    The one-pot synthesis of 1,2-disubstituted benzimidazoles by the transfer hydrogenation of azobenzene, using benzylamine as a hydrogen donor, sequential rearrangement of hydrazobenzene to semidine and further condensation with N-benzylideneamine is reported, catalyzed by 2 mol% of [Ni(COD)2] : dippe. The N2 substitution on benzimidazole can be controlled by the selection of different azobenzenes and C2 substitution will only depend on the chosen benzylamine. The current methodology avoids the addition of external oxidants, which are needed in the classical benzimidazole synthesis. In addition, the byproduct, N-benzylideneamine, obtained from dehydrogenation of benzylamine produced 2,4,5-trisubstituted imidazolines by cyclization and C-H functionalization, and this route was optimized with the use of 2 mol% of [Ni(COD)2] : 2PPh3. PMID:27254530

  11. Immunohistochemical expression of budding uninhibited by benzimidazole related 1 in leukoplakia and oral squamous cell carcinoma

    Directory of Open Access Journals (Sweden)

    Taneeru Sravya

    2016-01-01

    Full Text Available Background: Budding uninhibited by benzimidazole related 1 (BUBR1 is an important protein in the mitotic spindle assembly checkpoint. Alterations in expression of BUBR1 have been reported in many premalignant and malignant lesions. Aim: To compare the expression of BUBR1 with respect to the normal mucosa and degree of dysplasia in oral leukoplakia (OL and also with respect to different histopathological grades of oral squamous cell carcinoma (OSCC. Materials and Methods: Neutral buffered formalin-fixed and paraffin-embedded biopsy specimens 30 each of normal, OL and OSCC tissue were included in this study. The expression of BUBR1 was detected using immunohistochemistry (IHC. The scores obtained were subjected to ANOVA test. Results: Significant correlation was found in immunostaining between normal, dysplasia and OSCC groups with a P value of 0.00001. The expression of BUBR1 was significant when compared with different degrees of dysplasia and in different histopathological grades of OSCC with a P value of 0.00001. Conclusion: Higher IHC scores were obtained with increased histopathological grades of OL and OSCC suggesting its role as a prognostic indicator.

  12. Porous poly(benzimidazole) membrane for all vanadium redox flow battery

    Science.gov (United States)

    Luo, Tao; David, Oana; Gendel, Youri; Wessling, Matthias

    2016-04-01

    Porous poly(benzimidazole) (PBI) membranes of low vanadium ions permeability are described for an all vanadium redox flow battery (VRFB). The PBI membrane was prepared by a water vapour induced phase inversion process of a PBI polymer solution. The membrane has a symmetrical cross-sectional morphology. A low water permeability of 16.5 L (m2 h bar)-1 indicates the high hydraulic resistance stemming from a closed cell morphology with nanoporous characteristics. The PBI membrane doped with 2.5 M H2SO4 shows a proton conductivity of 16.6 mS cm-1 and VO2+ permeability as low as 4.5 × 10-8 cm2 min-1. The stability test of dense PBI membrane in VO2+ solution indicates good chemical stability. An all vanadium redox flow battery (VRFB) operated with the porous PBI membrane shows 98% coulombic efficiency and more than 10% higher energy efficiency compared to VRFB operated with Nafion 112 at applied current densities of 20-40 mA cm-2. High in situ stability of the porous PBI membrane was confirmed by about 50 cycles of continuous charge and discharge operation of the battery.

  13. Novel benzimidazole salts for lithium ion battery electrolytes: effects of substituents.

    Science.gov (United States)

    Sriana, T; Leggesse, E G; Jiang, J C

    2015-07-01

    In this paper, we report on our effort to design a novel lithium salt derived from bis(trifluoroborane)benzimidazolide by using density functional theory (DFT) calculations. The effects of different substituents are investigated with respect to ion pair dissociation energies and intrinsic anion oxidation potential of the molecules. Based on our calculations, we have found that ion pair dissociation energies and intrinsic anion oxidation potentials of the anions are mainly affected by the position and the type of substituents introduced into the parent structure. Compared to -CH3, substitution at the C2 position of the parent bis(trifluoroborane)benzimidazole (BTB(-)) by -CF3 results in an increase in anion oxidation stability. However, we observed a negligible change in the intrinsic anion oxidation potential as the length of the fluoroalkyl group increased to -C2F5. The most promising anions are generated by considering double-substitution at C2 and C5 positions. Among the possible anions, bis(trifluoroborane)-5-nitro-2-(trifluoromethyl) benzimidazolide (BTNTB(-)), with the calculated intrinsic anion oxidation potential of 5.50 V vs. Li(+)/Li, can be considered as a potential candidate for high voltage Li-ion batteries. PMID:26051990

  14. Synthesis of benzimidazole-grafted graphene oxide/multi-walled carbon nanotubes composite for supercapacitance application

    Energy Technology Data Exchange (ETDEWEB)

    Srivastava, Rajesh Kr., E-mail: r05bhu@gmail.com [Division of Physics and Applied Physics, School of Physical and Mathematical Sciences, Nanyang Technological University, 637371 Singapore (Singapore); Xingjue, Wang [Division of Physics and Applied Physics, School of Physical and Mathematical Sciences, Nanyang Technological University, 637371 Singapore (Singapore); Kumar, Vinod [Department of Zoology, Banaras Hindu University, Varanasi (India); Srivastava, Anchal [Department of Physics, Banaras Hindu University, Varanasi (India); Singh, Vidya Nand [CSIR-National Physical Laboratory, New Delhi (India)

    2014-11-05

    Highlights: • We are reporting supercapacitance performance of BI-GO/MWCNTs composite. • The specific capacitance of BI-GO/MWCNTs is 275 and 460 F/g at 200 and 5 mV/s scan rate. • This composite has shown 224 F/g capacitance after 1300 cycles at 200 mV/s scan rate. - Abstract: We are reporting the fabrication, characterizations and supercapacitance performance of benzimidazole-grafted graphene oxide/multi-walled carbon nanotubes (BI-GO/MWCNTs) composite. The synthesis of BI-GO materials involves cyclization reaction of carboxylic groups on GO among the hydroxyl and amino groups on o-phenylenediamine. The BI-GO/MWCNTs composite has been fabricated via in situ reduction of BI-GO using hydrazine in presence of MWCNTs. Scanning electron microscopy (SEM), Transmission electron microscopy (TEM), Raman spectroscopy, X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FTIR) have been used to characterize its surface and elemental composition. The uniform dispersion of MWCNTs with BI-GO helps to improve the charge transfer reaction during electrochemical process. The specific capacitance of BI-GO/MWCNTs composite is 275 and 460 F/g at 200 and 5 mV/s scan rate in 1 mol/L aqueous solution of H{sub 2}SO{sub 4}. This BI-GO/MWCNTs composite has shown 224 F/g capacitance after 1300 cycles at 200 mV/s scan rate, which represents its good electrochemical stability.

  15. A Two-dimensional Coordination Polymer of Manganese(II) and Benzimidazole-5,6-dicarboxylate

    Institute of Scientific and Technical Information of China (English)

    BI Cheng-Lu; SUN Jian-Hua

    2011-01-01

    A new two-dimensional (2D) manganese(II) coordination polymer {[Mn(bidc)(H2O)2]· 2H2O}n (H2bidc = benzimidazole-5,6-dicarboxylic acid) was synthesized, and characterized by X-ray crystallography and other measurements. The complex crystallizes in the orthorhombic system, space group Pbca with a = 7.0218(7), b = 17.9701(18), c = 19.0697(19), V = 2406.3(4)3, Z = 8, Dc = 1.823 g/cm3, Mr = 330.14, F(000) = 1344, μ(MoKα) = 1.140 mm-1, S = 1.055, R = 0.0305 and wR = 0.1012 for 2130 observed reflections (I 2σ(I)). The title complex consists of a novel 2D network with a topology of short symbol (4.82)(4.82).

  16. Photovoltaic properties of benzimidazole-derived perylene imides as an n-type material

    Energy Technology Data Exchange (ETDEWEB)

    Sim, Bo Ram [Department of Polymer Science and Engineering, Pusan National University, 30 Jangjeon-dong, Geumjeong-gu, Busan, 609-735 (Korea, Republic of); Kim, Bong-Gun [Department of Chemistry Education, Pusan National University, 30 Jangjeon-dong, Geumjeong-gu, Busan, 609-735 (Korea, Republic of); Lee, Jin Kook [Department of Polymer Science and Engineering, Pusan National University, 30 Jangjeon-dong, Geumjeong-gu, Busan, 609-735 (Korea, Republic of); Do, Jung Yun, E-mail: jydo@pusan.ac.kr [Department of Chemistry Education, Pusan National University, 30 Jangjeon-dong, Geumjeong-gu, Busan, 609-735 (Korea, Republic of)

    2011-09-01

    Perylene imide derivatives were considered as an n-type material for a bulk-heterojunction solar cell. A perylene was modified to imide-imidazole derivatives comprised of a benzimidazole moiety with several polar substituents and a long alkyl chain for favorable electronic energy levels and solubility. The electron mobility of methoxy-derived imide-imidazole was measured to be 4.0 x 10{sup -3} cm/V s under an electric field of 320 V/cm, being nearly comparable to the hole mobility of poly(3-hexylthiophene) (P3HT). The hole and electron mobilities of a blend film made of P3HT and the methoxy derivative were closely balanced at ca. 3 x 10{sup -4} cm/V s. The power conversion efficiency of a photovoltaic cell using the blend film was improved with the increase in perylene content and reached 0.20%. The methoxy substitution at the imid-imidazole resulted in better power conversion efficiency than unsubstitution. On the contrary, an alkyl ester substitution provided a low conversion efficiency of less than 0.01% due to a small current from severe crystallization in a polymer blend film.

  17. Synthesis and Photovoltaic Properties of Polymers Based on Cyclopentadithiophene and Benzimidazole Units

    Energy Technology Data Exchange (ETDEWEB)

    Song, Su Hee; Park, Sei Jung; Shim, Joo Young; Kim, Il; Suh, Hong Suk [Pusan National University, Busan (Korea, Republic of); Kwon, Soon Cheol; Lee, Kwang Hee [Gwangju Institute of Science and Technology, Gwangju (Korea, Republic of); Jin, Young Eup; Park, Sung Heum [Pukyong National University, Busan (Korea, Republic of)

    2012-06-15

    The new semiconducting copolymers with 4,4-dialkyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene and 2,2-dimethyl- 2H-benzimidazole units were synthesized. The fused aromatic rings, such as cyclopentadithiophene (CPDT) unit, can make the polymer backbone more rigid and coplanar, which induces long conjugation length, narrow band gap, and strong intermolecular {pi}-{pi} interaction. The stacking ability was controlled through attaching of linear or branched alkyl side chains. The spectra of PEHCPDTMBI and PHCPDTMBI in the solid films show absorption bands with maximum peaks at 401, 759 and 407, 768 nm, and the absorption onsets at 925 and 954 nm, corresponding to band gaps of 1.34 and 1.30 eV, respectively. The devices comprising PHCPDTMBI with TiO{sub X} showed a V{sub OC} of 0.39 V, a J{sub SC} of 1.14 mA/cm{sup 2}, and a FF of 0.34, giving a power conversion efficiency of 0.15%. The PHCPDTMBI with linear alkyl chain on CPDT shows good solubility in organic solvent with higher PCE value than that of PEHCPDTMBI

  18. Linear and nonlinear optical properties of Mn doped benzimidazole thin films

    Science.gov (United States)

    Praveen, P. A.; Babu, R. Ramesh; Prabhakaran, S. P.; Ramamurthi, K.

    2014-04-01

    In the present work, the Mn doped benzimidazole (BMZ) thin films were prepared by simple chemical bath deposition technique. The material was directly deposited as thin film on glass substrates and the metal concentration in the solution was varied in weight percentage in order to investigate the dopant effect on the properties of thin films. Similarly, the Mn doped BMZ films were deposited in different solution temperature to study the effect of deposition temperature on the properties of thin films. The PXRD and FT-IR spectroscopy are used to study the structural and the presence of functional groups in the BMZ medium. Depending upon the solution temperature, thickness of the films varying from 0.6 to 1.2 μm and the optical transparency of the samples increases with the increasing temperature up to 50 °C. Second Harmonic Generation (SHG) efficiency of the films is measured for all the films. Third order nonlinear optical properties of the films were analyzed using Z-scan technique. The experimental results show that Mn doped BMZ films exhibits saturation absorption and negative nonlinearity.

  19. Crystal Structure and Electronic Structure of a Luminescent Compound 2-(2-Pyridyl) Benzimidazole

    Institute of Scientific and Technical Information of China (English)

    岳淑美; 苏忠民; 马建方; 廖奕; 阚玉和; 张恒君

    2003-01-01

    The crystal structure of 2-(2-pyridyl) benzimidazole was determined by singlecrystal X-ray diffraction at 193(2) K. It crystallizes in orthorhombic system, space group Pbca with unit cell constants a = 10.6204(7), b = 10.1407(4), c = 18.6327(8) A, Z= 8, V= 2006.7(2) A3, Dc. =1.292 g/cm3, F(000) = 816 andμ(MoKα) = 0.081 mm-1. The structure was refined to R = 0.0317 and wR = 0.0454 for 795 observed reflections with Ⅰ> 2σ(Ⅰ). In the solid state, it has an emission maximum at 369 nm, while in solution (DMSO), the maximum excitation is at 372 nm. Quantum chemistry calculation was performed by the method of density functional theory. Theoretical results show that atom N is the reactive site when coordinating with a metal, and the electronic structure of the title compound presents excellent carrier transport properties.

  20. The 2D Selfassembly of Benzimidazole and its Co-crystallization

    Science.gov (United States)

    Costa, Paulo; Teeter, Jacob; Kunkel, Donna; Sinitskii, Alexander; Enders, Axel

    Benzimidazoles (BI) are organic molecules that form ferroelectric crystals. Key to their ferroelectric behavior are the switchable N . . . HN type bonds and how they couple to the electron system of the molecules. We attempted to crystallize BI on various metal surfaces and studied them using STM. We observed that on Au and Ag, BI joins into zipper chains characteristic of its bulk structure that can pack into a continuous 2D layer. Because the dipole of BI lies in the direction of its switchable hydrogen bond, these zippers should in principle have reversible polarizations that point along the direction they run. BI's crystallization is reminiscent to how croconic acid (CA) crystallizes in 2D using O . . . HO bonding, suggesting that these molecules may be able to co-crystallize through OH . . . N bonds. This would present the opportunity to modify BI's properties, such as the energy needed to switch a hydrogen from a donor to acceptor site. When co-deposited, CA and BI successfully combine into a co-crystal formed by building blocks consisting of 2 CA and 2 BI molecules. These findings demonstrate the usefulness of using STM as a preliminary check to verify if two molecules are compatible with each other without having to attempt crystallization with multiple solvents and mixing methods.

  1. Correlation between the molecular structure and the inhibiting effect of some benzimidazole derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Niamien, P.M., E-mail: niamienfr@yahoo.fr [Laboratoire de chimie physique, Universite de Cocody-Abidjan, 22 BP 582 Abidjan (Cote d' Ivoire); Essy, F.K.; Trokourey, A.; Yapi, A.; Aka, H.K. [Laboratoire de chimie physique, Universite de Cocody-Abidjan, 22 BP 582 Abidjan (Cote d' Ivoire); Diabate, D. [Laboratoire de chimie physique, Universite de Cocody-Abidjan, 22 BP 582 Abidjan (Cote d' Ivoire); Institut UTINAM-UMR CNRS 6213 Equipe capteurs et membranes 25013 Besancon cedex, 22 BP 582 Abidjan 22 (Cote d' Ivoire)

    2012-09-14

    Quantum chemical parameters of 2-thiobenzylbenzimidazole (TBBI), 2-thiomethylbenzimidazole (TMBI), and 2-mercaptobenzimidazole (MBI) were calculated. The correlation between molecular structure of these compounds and their inhibition efficiency IE (%) against copper corrosion in 1 M HNO{sub 3} was found by considering Density Functional Theory DFT/B3LYP/6-31G (d, p) level. The properties most relevant to their potential action as corrosion inhibitors have been calculated: highest occupied molecular orbital energy (E{sub HOMO}), lowest unoccupied molecular orbital energy (E{sub LUMO}), energy gap ({Delta}E), dipole moment ({mu}) and parameters that provide informations about the chemical reactivity: electronegativity ({chi}), global hardness ({eta}), global softness ({sigma}) and electrophilicity index ({omega}). All calculations have been performed using the Gaussian 03W suite of programs. It was found that theoretical data support experimental results. -- Highlights: Black-Right-Pointing-Pointer Benzimidazole derivatives (TBBI, TMBI, MBI) as corrosion inhibitors of copper in 1 M HNO{sub 3}. Black-Right-Pointing-Pointer The inhibition process evaluated by weight loss indicates that the investigated compounds are good inhibitors of copper. Black-Right-Pointing-Pointer The inhibition efficiency is found to be in the following order: TBBI > TMBI > MBI. Black-Right-Pointing-Pointer The studied molecules adsorbed on the metal surface according to the Langmuir adsorption isotherm. Black-Right-Pointing-Pointer Most of the calculated molecular parameters by DFT/B3LYP/6-31G (d, p) show excellent correlation with the inhibition efficiency.

  2. 2-(2-Pyridyl) Benzimidazole Analogs and their beta-Glucuronidase Inhibitory Activity

    International Nuclear Information System (INIS)

    Synthesis of 2-(2-Pyridyl) benzimidazole analogs 1-11 have been carried out and evaluated for in vitro beta-glucuronidase inhibitory potential. The compounds 4 (IC/sub 50/ = 4.06 ± 0.34 meuM), 5 (IC/sub 50/ = 09.63 ± 0.81 meuM), 1 (IC/sub 50/ = 19.66 ± 0.44 meuM), 7 (IC/sub 50/ = 24.75 ± 0.25 meuM), 6 (IC/sub 50/ = 26.30 ± 1.37 meuM), and 3 (IC/sub 50/ = 32.11 ± 0.89 meuM), showed beta-glucuronidase inhibitory activity superior to the standard D-saccharic acid 1,4-lactone, with (IC/sub 50/ = 48.4 ± 1.25 meuM). Based on structure-activity relationship, we discover a new class of potent beta-glucuronidase inhibitors. (author)

  3. Bioremediation of Carbendazim, a Benzimidazole Fungicide Using Brevibacillus borstelensis and Streptomyces albogriseolus Together.

    Science.gov (United States)

    Arya, Ridhima; Sharma, Anil K

    2015-01-01

    Excessive use of pesticides in agriculture has resulted in contamination of water resources, air, soil and disruption of biogeochemical cycles. These compounds adversely affect humans and animal health, helpful soil microbes and crop production as well. Biodegradation of pesticides by microbes exists in a number of habitats like soil, sediments, surface, ground water, and sludge, etc. In the present study, efforts were made to develop a microbial consortium comprising of Streptomyces albogriseolus and Brevibacillus borstelensis strains isolated earlier which are capable of degrading carbendazim, a benzimidazole fungicide and making it harmless. Both the strains Brevibacillus borstelensis and Streptomyces albogriseolus displayed growth even at higher concentrations (500μg mL(-1)) of carbendazim. The consortium containing Brevibacillus borstelensis and Streptomyces albogriseolus reduced carbendazim concentration from 30 µg mL(-1) to 0.86 µg mL(-1) (nearly 97%) in 12hrs to 0.60 µg mL(-1) (~98%) in 20 hrs as determined by LCMS analysis. There was a significant reduction observed in carbendazim concentration than reduction obtained when individual strain was used. This study paves a way for further exploration of degradation mechanism at the genetic level to enhance the capability of microorganisms in consortia. PMID:26420048

  4. Structural investigation of HIV-1 nonnucleoside reverse transcriptase inhibitors: 2-Aryl-substituted benzimidazoles

    Science.gov (United States)

    Ziółkowska, Natasza E.; Michejda, Christopher J.; Bujacz, Grzegorz D.

    2009-11-01

    Acquired immunodeficiency syndrome (AIDS) caused by the human immunodeficiency virus (HIV) is one of the most destructive epidemics in history. Inhibitors of HIV enzymes are the main targets to develop drugs against that disease. Nonnucleoside reverse transcriptase inhibitors of HIV-1 (NNRTIs) are potentially effective and nontoxic. Structural studies provide information necessary to design more active compounds. The crystal structures of four NNRTI derivatives of 2-aryl-substituted N-benzyl-benzimidazole are presented here. Analysis of the geometrical parameters shows that the structures of the investigated inhibitors are rigid. The important geometrical parameter is the dihedral angle between the planes of the π-electron systems of the benzymidazole and benzyl moieties. The values of these dihedral angles are in a narrow range for all investigated inhibitors. There is no significant difference between the structure of the free inhibitor and the inhibitor in the complex with RT HIV-1. X-ray structures of the investigated inhibitors are a good basis for modeling enzyme-inhibitor interactions in rational drug design.

  5. Synthesis and Crystal Structure of catena-Poly[bis-(benzimidazole)cobalt(Ⅱ) μ- Phthalato

    Institute of Scientific and Technical Information of China (English)

    XUE Yu-Hong; ZHANG Li; XU Duan-Jun

    2005-01-01

    The title polymeric complex [Co(C8H4O4)(C7H6N2)2]n has been prepared and its crystal structure was determined by X-ray diffraction method. The crystal belongs to monoclinic,space group C2/c with a = 7.7865(12), b = 20.4215(18), c = 13.4880(14) (A),β = 103.298(2)°, V = 2087.3(4) (A)3, Mr = 459.32, Z = 4, Dc= 1.462 g/cm3,μ = 0.859 mm-1, F(000) = 940, R = 0.0636 and wR = 0.1639 for 1278 observed reflections (I > 2σ(Ⅰ)). The complex assumes a distorted tetrahedral coordination geometry, formed by two phthalate anions and two benzimidazoles (bzim). The phthalate anions bridge the neighboring Co(Ⅱ) atoms to form the polymeric chains. The centroid distance of 3.471(3) (A) between the parallel bzim rings of adjacent polymeric chains suggests the existence of π-π stacking.

  6. In vitro detection of benzimidazole resistance in Haemonchus contortus: egg hatch test versus larval development test.

    Science.gov (United States)

    Várady, M; Cudeková, P; Corba, J

    2007-10-21

    The present study was designed to compare the egg hatch test (EHT) and the larval development test (LDT) as in vitro tools for detection of benzimidazole (BZ) resistance in Haemonchus contortus, a nematode parasite of small ruminants. Comparisons were made during a course of infection and changes in both EHT and LDT were monitored to measure the correlation between resistance and susceptibility in different parasite stages (eggs and larvae). In addition, mixed doses of known numbers of susceptible and BZ-resistant H. contortus eggs were used to assess the sensitivity of LDT for the detection of low levels of resistance. The degree of resistance for each test was expressed as resistance factor (RF). The LDT showed a greater ability to distinguish between four susceptible and four resistant isolates of H. contortus with higher resistance factors compared to the EHT. For the EHT the RF by using ED(50) criterion ranged from 3.2 to 13.3 and from 7.4 to 25.2 by using LC(99). For LDT the resistant isolates were 4.3-63.1 times more tolerant than the susceptible isolates using the ED(50) criterion and 91.1-1411.0 times more tolerant using the LC(99) criterion. The LDT was also able to clearly indicate the presence of low level (4%) of resistant larvae amongst a susceptible background population.

  7. Self-assembled 1-octadecyl-1H-benzimidazole film on copper surface for corrosion protection

    Indian Academy of Sciences (India)

    B V Appa Rao; M Marsihma Reddy

    2013-11-01

    Films of 1-octadecyl-1H-benzimidazole (OBI) have been formed on copper surface by selfassembly method. Optimum conditions viz. the solvent, concentration of OBI, immersion period and temperature for the formation of a protective film on copper have been established using impedance studies. The OBI film has been characterized by X-ray photoelectron spectroscopy, reflection absorption Fourier transform infrared (FTIR) spectroscopy, contact angle measurements and atomic force microscopy. Efficiency of the OBI film to protect copper from corrosion has been investigated in aq. HCl solution using electrochemical impedance spectroscopy, potentiodynamic polarization method, cyclic voltammetry, scanning electron microscopy and gravimetry. Results of these studies inferred that the OBI film has an inhibition efficiency in the range of 97-99% under different conditions. Polarization studies inferred that the OBI film functions as a cathodic inhibitor. Cyclic voltammetric studies showed that the film is stable even after 15 cycles, when the copper electrode is polarized to an anodic potential of 0.35V vs. Ag/AgCl electrode.

  8. Synthesis and Structure of L-Aspartato-nickel(II) Complex with Benzimidazole

    Institute of Scientific and Technical Information of China (English)

    张骊; 戴志远

    2004-01-01

    The title complex Ni(C4H5NO4)(C7H6N2)3·1.75(H2O)(C25H26.5N7NiO5.75,Mr=575.74) has been prepared and its crystal structure was determined by X-ray diffraction method.The crystal of this chiral complex belongs to monoclinic,space group P21 with a=13.208(1),b=10.741(1),c=19.398(1)A,β=104.39(1)°,V=2665.8(4)A3,Z=4,Dc=1.435 g/cm3,μ(MoKα)=0.780 mm-1 and F(000)=1198.The final R=0.0504 and wR=0.1267 for 9159 observed reflections (I>2σ(I)),and R=0.065 and wR=0.1299 for 11006 independent reflections.The complex assumes a distorted octa-hedral coordinate geometry formed by one aspartate dianion and three benzimidazole ligands.The aspartate chelates to the Ni atom as a tridentate ligand.The lattice water molecules are hydrogen-bonded to the Ni complex molecule.

  9. Evaluation of Benzimidazole Resistance in Haemonchus Contortus Using Comparative PCR-RFLP Methods

    Directory of Open Access Journals (Sweden)

    S Bokaie

    2011-06-01

    Full Text Available Background: In order to deworm the ruminants especially of sheep in Iran, consumption of benzimi­dazoles has more than 2 decades history and today farmers are using imidazothiazoles, macrocyclic lactones and mostly benzimidazole compounds (BZs to treat infected farm animals. It has been demonstrated that the most common molecular mechanism leading to BZsresistance in Haemonchus contortus is a single mutation at amino acid 200 (phenylalanine to tyrosine of the isotype 1 of beta tubulin gene. According to the report of such mutations in Iranian Telador­sagia circumcincta isolates with Restriction Site Created PCR-RFLP, we decided to evaluate the frequency of such mutations in H. contortus in three different geographical areas of Iran.Methodes: A total of 102 collected adult male H. contortus were evaluated with PCR-RFLP (us­ing PSP1406I as restriction enzyme. By means of a second step to compare function of different methods and to increase sensitivity of detection mechanism, a third of samples were examined by another PCR-RFLP method (using TaaI as restriction enzyme and finally beta tubulin gene of two samples was sequenced.Results: All of samples were detected as BZss homozygote. Finally, beta tubulin gene sequenc­ing of two samples showed no point mutation at codon 200.Conclusion: It seems that BZresistance of H. contortus in Iran is not a serious problem as antici­pated before.

  10. Efficient synthesis and in vitro antifungal activity of 1H-benzimidazol-1-yl acetates/propionates containing 1H-1,2,4-triazole moiety

    Institute of Scientific and Technical Information of China (English)

    Pei Zhi Zhang; Shao Fang Zhou; Tian Ren Li; Lin Jiang

    2012-01-01

    A series of novel 1H-benzimidazol-1-yl acetates and 1H-benzimidazol-1-yl propionates containing 1H-1,2,4-triazole moiety were synthesized under microwave irradiation by multi-step reactions,in yields of 87-94%.Their in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum were evaluated by mycelial growth rate method.All the target compounds exhibit high activities against B.cinerea with the EC50 values of 7.96-21.74 μg/mL,higher than that of carbendazim.

  11. Bis{1-[(1H-benzimidazol-1-ylmethyl-κN3]-1H-1,2,3,4-tetrazole}silver(I nitrate

    Directory of Open Access Journals (Sweden)

    Xiang-ru Meng

    2010-03-01

    Full Text Available In the title salt, [Ag(C9H8N62]NO3, the central AgI atom is linearly coordinated by the N atoms [171.97 (8°] from two 1-[(benzimidazol-1-ylmethyl]-1H-1,2,3,4-tetrazole ligands. The benzimidazole rings in adjacent molecules are parallel with an average interplanar distance of 3.461 Å; adjacent molecules are linked through N—H...O hydrogen bonds into a linear chain along the b-axis direction.

  12. Role of benzimidazole (Bid) in the delta-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH(2)-Bid (UFP-502).

    Science.gov (United States)

    Salvadori, Severo; Fiorini, Stella; Trapella, Claudio; Porreca, Frank; Davis, Peg; Sasaki, Yusuke; Ambo, Akihiro; Marczak, Ewa D; Lazarus, Lawrence H; Balboni, Gianfranco

    2008-03-15

    H-Dmt-Tic-NH-CH(2)-Bid (UFP-502) was the first delta-opioid agonist prepared from the Dmt-Tic pharmacophore. It showed interesting pharmacological properties, such as stimulation of mRNA BDNF expression and antidepression. To evaluate the importance of 1H-benzimidazol-2-yl (Bid) in the induction of delta-agonism, it was substituted by similar heterocycles: The substitution of NH(1) by O or S transforms the reference delta-agonist into delta-antagonists. Phenyl ring of benzimidazole is not important for delta-agonism; in fact 1H-imidazole-2-yl retains delta-agonist activity.

  13. Complexes cobalt(II, zinc(II and copper(II with some newly synthesized benzimidazole derivatives and their antibacterial activity

    Directory of Open Access Journals (Sweden)

    S. O. PODUNAVAC-KUZMANOVIC

    1999-05-01

    Full Text Available The preparation and properties of some complexes of cobalt(II, zinc(II and copper(II with several newly synthesized benzimidazole derivatives (L are reported. The complexes, of the general formula [MCl2L2] (M=Co(II, Zn(II and [CuCl2L(H2O], have a tetrahedral structure. The complexes were characterized by elemental analysis, molar conductivity, magnetic susceptibility measurements, IR and absorption electronic spectra. The antibacterial activitiy of the benzimidazoles and their complexes was evaluated against Erwinia carotovora subsp. carotovora and Erwinia amylovora. The complexes were found to be more toxic than the ligands.

  14. Aromatic carboxylate effect on dimensionality of three bis(benzimidazole)-based cobalt(II) coordination polymers: Syntheses, structures and properties

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, Ju-Wen; Gong, Chun-Hua; Hou, Li-Li; Tian, Ai-Xiang; Wang, Xiu-Li, E-mail: wangxiuli@bhu.edu.cn

    2013-09-15

    Three new metal-organic coordination polymers [Co(4-bbc){sub 2}(bbbm)] (1), [Co(3,5-pdc)(bbbm)]·2H{sub 2}O (2) and [Co(1,4-ndc)(bbbm)] (3) (4-Hbbc=4-bromobenzoic acid, 3,5-H{sub 2}pdc=3,5-pyridinedicarboxylic acid, 1,4-H{sub 2}ndc=1,4-naphthalenedicarboxylic acid and bbbm=1,1-(1,4-butanediyl)bis-1H-benzimidazole) were hydrothermally synthesized and structurally characterized. Polymer 1 is a 1D chain formed by the bbbm ligands and Co{sup II} ions. Polymer 2 exhibits a 2D network with a (3·4·5)(3{sup 2}·4·5·6{sup 2}·7{sup 4}) topology. Polymer 3 possesses a 3D three-fold interpenetrating framework. The versatile structures of title polymers indicate that the aromatic carboxylates have an important influence on the dimensionality of 1–3. Moreover, the thermal stability, electrochemical and luminescent properties of 1–3 were investigated. - graphical abstract: Three bis(benzimidazole)-based cobalt(II) coordination polymers tuned by aromatic carboxylates were hydrothermally synthesized and structurally characterized. The aromatic carboxylates play a key role in the dimensionality of three polymers. The electrochemical and luminescent properties of three polymers were investigated. Display Omitted - Highlights: • Three bis(benzimidazole)-based cobalt(II) coordination polymers tuned by aromatic carboxylates were obtained. • The aromatic carboxylates have an important influence on the dimensionality of three polymers. • The electrochemical and luminescent properties of three polymers were investigated.

  15. Vasodilator activity of 2-(p-chloro-alpha-hydroxybenzyl)benzimidazole (HBBPC) on femoral vascular bed of the rabbit.

    Science.gov (United States)

    Demenge, P; Silice, C; Luu Duc, C; Carraz, G

    1979-01-01

    The effects of 2-(p-chloro-alpha-hydroxybenzyl) benzimidazole HCl (HBBPC) have been studied on the femoral peripheral resistance (i.v. route) and only femoral blood flow (local i.a. injection), in comparison with other vasodilators, i.e., sodium nitroprusside, dihydralazine and piribedil. The vasomotor activity of HBBPC, namely, decreased peripheral resistance and increased femoral blood flow, seems interesting because it begins after pressure has returned to normal. This substance is likely to induce a vasoconstriction in other areas (increased femoral blood flow with decreased peripheral resistance without a fall of blood pressure).

  16. Tetraaquabis[(1-carboxylatomethyl-1,3-benzimidazol-3-ium-3-ylacetato-κO]palladium(II dihydrate

    Directory of Open Access Journals (Sweden)

    Ridong Wang

    2008-07-01

    Full Text Available In the title compound, [Pd(C11H9N2O42(H2O4]·2H2O, the palladium(II cation lies on an inversion centre and is hexacoordinated by two carboxylate O atoms from two (1-carboxylatomethyl-1,3-benzimidazol-3-ium-3-ylacetate ligands and four water molecules, with a slightly distorted octahedral geometry. O—H...O hydrogen bonds link the molecules together.

  17. Crystal structure of ethyl 2-(1H-benzimidazol-2-yl-2-[2-(4-nitrophenylhydrazinylidene]acetate

    Directory of Open Access Journals (Sweden)

    Mohamed Loughzail

    2015-04-01

    Full Text Available The title compound, C17H15N5O4, was obtained via the condensation of 3-ethoxy-2-[2-(4-nitrophenylhydrazono]-3-oxopropanoic acid with 1,2-diaminobenzene. In the molecule, the dihedral angles between the acetate group and the two aromatic subunits (benzimidazole and nitrophenylhydrazone are 7.35 (9 and 18.23 (9°, respectively. Intramolecular N—H...O and N—H...N contacts occur. In the crystal, C—H...O and N—H...O hydrogen bonds link the molecules into chains along the b-axis direction.

  18. Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN3copper(II pentahydrate

    Directory of Open Access Journals (Sweden)

    Ya-Bo Xie

    2008-07-01

    Full Text Available The title compound, [Cu(C9H4N2O4(H2O5]·5H2O, contains one crystallographically independent CuII atom and one 1H-benzimidazole-5,6-dicarboxylate (bdc ligand, along with five coordinated and five uncoordinated water molecules. The CuII atom is six-coordinated by one N atom from the bdc ligand and five O atoms from water molecules, giving an octahedral coordination geometry. Hydrogen bonds link the mononuclear complex and uncoordinated water molecules into a three-dimensional network.

  19. Syntheses of Benzimidazoles, Quinoxalines and 3,3-Dihydro 1 H-1,5-benzodiazepines Starting from o-Phenylenediamine

    Institute of Scientific and Technical Information of China (English)

    CUI Yong; TANG Xiu-Bo; SHAO Chang-Xing; LI Ji-Tai; SUN Wen-Hua

    2005-01-01

    A series of benzo-fused heteroaromatic compounds with 5-, 6- and 7-membered rings, such as benzimidazole,quinoxaline and 1H-1,5-benzodiazepine derivatives, were synthesized through condensation reaction of o-phenyl-enediamine with aryl aldehydes or ketones. The experimental conditions were carefully examined, and the products were characterized by 1H NMR, 13C NMR, MS, IR and elemental analyses. In addition, the structure of a benzodiazaepine derivative with 7-membered ring was confirmed by single crystal X-ray diffraction analysis.

  20. Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore.

    Science.gov (United States)

    Balboni, Gianfranco; Trapella, Claudio; Sasaki, Yusuke; Ambo, Akihiro; Marczak, Ewa D; Lazarus, Lawrence H; Salvadori, Severo

    2009-09-10

    To improve the structure-activity studies of the lead delta opioid agonist H-Dmt-Tic-Asp*-Bid, we synthesized and pharmacologically characterized a series of analogues in which the side chain next to 1H-benzimidazole-2-yl (Bid) was substituted by those endowed with different chemical properties. Interesting results were obtained: (1) only Gly, Ala, and Asp resulted in delta agonism, (2) Phe yielded delta antagonism, (3) and all other residues except Glu (devoid of any activity) gave mu agonism.

  1. 2-[4-(1H-1,2,4-Triazol-1-yl)phen­yl]-1H-benzimidazole

    Science.gov (United States)

    Cheng, Long-Huai; Zheng, Zheng; Han, Zhi-Li; Wu, Zhi-Chao; Zhou, Hong-Ping

    2012-01-01

    In the title compound, C15H11N5, the benzimidazole ring system is nearly planar [maximum deviation = 0.039 (2) Å], and is oriented at a dihedral angle of 28.85 (10)° with respect to the benzene ring; the dihedral angle between the triazole and benzene rings is 17.30 (15)°. In the crystal N—H⋯N hydrogen bonds link the mol­ecules into chains. Weak C—H⋯N inter­actions are also present. PMID:23125686

  2. A comprehensive approach to the determination of two benzimidazoles in environmental samples.

    Science.gov (United States)

    Wagil, Marta; Maszkowska, Joanna; Białk-Bielińska, Anna; Stepnowski, Piotr; Kumirska, Jolanta

    2015-01-01

    Among the various pharmaceuticals regarded as emerging pollutants, benzimidazoles--represented by flubendazole and fenbendazole--are of particular concern because of their large-scale use in veterinary medicine and their health effects on aquatic organisms. For this reason, it is essential to have reliable analytical methods which can be used to simultaneously monitor their appearance in environmental matrices such as water, sediment and tissue samples. To date, however, such methods relating to these three matrices have not been available. In this paper we present a comprehensive approach to the determination of both drugs in the mentioned above matrices using liquid chromatography-ion trap mass spectrometry (LC-MS/MS). Special attention was paid to the sample preparation step. The optimal extraction methods were further validated by experiments with spiked water, sediment and fish tissue samples. Matrix effects were established. The following absolute recoveries of flubendazole and fenbendazole were achieved: 96.2% and 95.4% from waters, 103.4% and 98.3% from sediments, and 98.3% and 97.6% from fish tissue samples, respectively. Validation of the LC-MS/MS methods enable flubendazole and fenbendazole to be determined with method detection limits: 1.6 ng L(-1) and 1.7 ng L(-1) in water samples; 0.3 ng g(-1) for both compounds in sediment samples, and 3.3 ng g(-1) and 3.5 ng g(-1) in tissue samples, respectively. The proposed methods were successfully used for analysing selected pharmaceuticals in real samples collected in northern Poland. There is first data on the concentration in the environment of the target compounds in Poland.

  3. 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)

  4. Sulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}ester a recyclable catalyst for the synthesis of 2-aryl-1-arylmethyl- 1H-1,3-benzimidazole derivatives

    Institute of Scientific and Technical Information of China (English)

    Nasir Iravani; Negar Safikhani Mohammadzade; Khodabakhsh Niknam

    2011-01-01

    A highly selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles from the reaction of o-phenylenediamine and aromatic aldehydes in the presence of sulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}Jester (SASPSPE) in water and at 80 ℃ in good to excellent yields.

  5. Solventless synthesis of 2-aryl- 1-arylmethyl- 1H- 1,3-benzimidazoles catalyzed by Fe(ClO4)3 at room temperature

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A series of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles was synthesized expeditiously in good yields from o-phenylenediamines and aldehydes in the presence of Fe(ClO4)3 without solvent at room temperature.

  6. Microwave Synthesis, Characterization and DNA-binding Properties of a New Cobalt(Ⅱ) Complex with 2,6-Bis(benzimidazol-2-yl)pyridine

    Institute of Scientific and Technical Information of China (English)

    Nian Yuan TAN; Xiao Ming XIAO; Ze Lin LI; Takeko MATSUMURA-INOUE

    2004-01-01

    A new cobalt(Ⅱ) complex with tridentate ligand 2, 6-bis (benzimidazol- 2-yl)pyridine has been synthesized by microwave irradiation method and characterized by elemental analysis, electrochemical and spectral methods. The binding of the complex with calf thymus DNA has also been investigated by absorption and fluorescence spectra.

  7. A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles

    Indian Academy of Sciences (India)

    G A N K Durgareddy; R Ravikumar; S Ravi; Srinivas R Adapa

    2013-01-01

    One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO3)2.3H2O catalyst at room/ambient temperature in excellent yield.

  8. Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines.

    Science.gov (United States)

    Almansour, Abdulrahman I; Arumugam, Natarajan; Suresh Kumar, Raju; Soliman, Saied M; Altaf, Mohammad; Ghabbour, Hazem A

    2016-01-01

    A series of benzimidazole-tethered oxazepine heterocyclic hybrids has been synthesized in good to excellent yields from an N-alkylated benzimidazole 2-carboxaldehyde, which in turn was accomplished from o-phenylenediamine in three good yielding steps. The calculated molecular structure of compounds 2-methyl-4-(2-((phenylimino)methyl)-1H-benzo-[d]imidazol-1-yl)-butan-2-ol 9 and 10 3,3-dimethyl-N-phenyl-1,2,3,5-tetrahydrobenzo-[4,5]imidazo[2,1-c][1,4]oxazepin-5-amine using the B3LYP/6-31 G(d, p) method were found to agree well with their X-ray structures. The charge distributions at the different atomic sites were computed using the natural bond orbital (NBO) method. The regions of electrophilic and nucleophilic reactivity were shown using a molecular electrostatic potential (MEP) map. In addition, the frontier molecular orbitals of these compounds were discussed at the same level of theory. Nonlinear optical (NLO) properties have also been investigated by computational hyperpolarizability studies, and it was found that Compound 9 is the best candidate for NLO applications. PMID:27271585

  9. Eight supramolecular assemblies constructed from bis(benzimidazole) and organic acids through strong classical hydrogen bonding and weak noncovalent interactions

    Science.gov (United States)

    Jin, Shouwen; Wang, Daqi

    2014-05-01

    Eight crystalline organic acid-base adducts derived from alkane bridged bis(N-benzimidazole) and organic acids (2,4,6-trinitrophenol, p-nitrobenzoic acid, m-nitrobenzoic acid, 3,5-dinitrobenzoic acid, 5-sulfosalicylic acid and oxalic acid) were prepared and characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. Of the eight compounds five are organic salts (1, 4, 6, 7 and 8) and the other three (2, 3, and 5) are cocrystals. In all of the adducts except 1 and 8, the ratio of the acid and the base is 2:1. All eight supramolecular assemblies involve extensive intermolecular classical hydrogen bonds as well as other noncovalent interactions. The role of weak and strong noncovalent interactions in the crystal packing is ascertained. These weak interactions combined, all the complexes displayed 3D framework structure. The results presented herein indicate that the strength and directionality of the classical N+-H⋯O-, O-H⋯O, and O-H⋯N hydrogen bonds (ionic or neutral) and other nonbonding associations between acids and ditopic benzimidazoles are sufficient to bring about the formation of cocrystals or organic salts.

  10. The ternary metal mixed ligand complexes formed by benzimidazole and N, N-bis(2-hydroxyethyl) glycine

    Institute of Scientific and Technical Information of China (English)

    贺小凤; 龙腊生; 毋福海; 乐学义; 陈小明; 计亮年; 周忠远

    1999-01-01

    The stability constants of the ternary M(Bic)(Bzim)+ complexes, where M2+=Cu2+, Ni2+ or Zn2+, Bic-=the anion of N, N-bis(2-hydroxyethyl) glycine and Bzim = benzimidazole, were determined by potentiometric pH titration in aqueous solution. One of them (M2+ = Cu2+) was also separately determined by spectrophotometry. The results show that these ternary complexes are stabler than expected on statistical grounds. The enhanced stability of the ternary M(Bic) (Bzim)+ complexes is attributed to the πA-πB cooperative effect between Bic- and benzimidazole. Besides, compared with Cu(Bic) (Bzim)+ and Ni(Bic) (Bzim)+, the ternary Zn(Bic)(Bzim)+ complex has relatively high stability. The crystal structure of [Cu(Bic)(Bzim)]ClO4 was determined by single crystal X-ray diffraction techniques. The copper atom has a trigonal-bipyramidal geometry, the basal plane is formed by an oxygen atom of the carboxylato group and two hydroxyl oxygen atoms, the apical position is occupied by a nitrogen a

  11. Synthesis, interaction with DNA and antiproliferative activities of two novel Cu(II) complexes with norcantharidin and benzimidazole derivatives

    Science.gov (United States)

    Song, Wen-Ji; Lin, Qiu-Yue; Jiang, Wen-Jiao; Du, Fang-Yuan; Qi, Qing-Yuan; Wei, Qiong

    2015-02-01

    Two novel complexes [Cu(L)2(Ac)2]·3H2O (1) (L = N-2-methyl benzimidazole demethylcantharate imide, C16H15N3O3, Ac = acetate, C2H3O2) and [Cu(bimz)2(DCA)] (2) (bimz = benzimidazole, C7H6N2; DCA = demethylcantharate, C8H8O5) were synthesized and characterized by elemental analysis, infrared spectra and X-ray diffraction techniques. Cu(II) ion was four-coordinated in complex 1, Cu(II) ion was five-coordinated in complex 2. A large amount of intermolecular hydrogen-bonding and π-π stacking interactions were observed in these complex structures. The DNA-binding properties of these complexes were investigated using electronic absorption spectra, fluorescence spectra, viscosity measurements and agarose gel electrophoresis. The interactions between the complexes and bovine serum albumin (BSA) were investigated by fluorescence spectra. The antiproliferative activities of the complexes against human hepatoma cells (SMMC7721) were tested in vitro. And the results showed that these complexes could bind to DNA in moderate intensity via partial intercalation, and complexes 1 and 2 could cleave plasmid DNA through hydroxyl radical mechanism. Title complexes could effectively quench the fluorescence of BSA through static quenching. Meanwhile, title complexes had stronger antiproliferative effect compared to L and Na2(DCA) within the tested concentration range. And complex 1 possessed more antiproliferative active than complex 2.

  12. Synthesis, spectroscopic characterization and DFT calculations of N-Methyl-2-(2ʹ-hydroxyphenyl)benzimidazole derivatives

    Science.gov (United States)

    Saral, Hasan; Özdamar, Özgür; Uçar, İbrahim; Bekdemir, Yunus; Aygün, Muhittin

    2016-01-01

    1-Methyl-2-(2ʹ-hydroxyphenyl)benzimidazole (1) and 1-Methyl-2-(2ʹ-hydroxy-4ʹ-methylphenyl)benzimidazole (2) compounds have been synthesized and characterized by XRD, IE-MS, FT-IR, UV-Vis and 1H, 13C NMR techniques. The crystal structure of both compounds is stabilized with very strong O-H … N hydrogen-bond and π-π interactions. In the compound 1, an infinite chain structure with a trans-zigzag type was formed along the crystallographic [101] direction. Quantum mechanical calculations of energies, geometries, vibrational wavenumbers, NMR and electronic transitions were carried out by DFT using B3LYP functional combined with 6.31G(d,p) basis set. Calculated bond lengths, bond angles and dihedral angles were only slightly different from the experimental ones. The vibrational study was interpreted by means of potential energy distribution (PED). The electronic absorption spectra of the both compounds were predicted by using the time-dependent DFT methods and good agreement was found between the computational and the experimental values. The chemical shifts (1H and 13C NMR) and isotropic shielding values were calculated by using the gauge-invariant atomic orbital (GIAO) method. The analyses of HOMO and LUMO have been used to explain the charge transfer within the molecule.

  13. Influences of water in bis-benzimidazole-derivative electrolyte additives to the degradation of the dye-sensitized solar cells

    Energy Technology Data Exchange (ETDEWEB)

    Lu, Hung-Lin; Yang, Thomas C.-K. [Department of Chemical Engineering, National Taipei University of Technology, No. 1, Section 3, Chung-hsiao East Road, Taipei 106 (China); Lee, Yu-Hui; Huang, Sheng-Tung [Institute of Biotechnology, National Taipei University of Technology, Taipei 106 (China); Su, Chaochin [Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106 (China)

    2011-01-15

    The chemical stability of dye-sensitized solar cells (DSSC) determines both the cell performance and the cell life-time. The presence of water in the solar cell from surrounding leakage through the imperfection packaging sealants causes the decrease in life-time of photogenerated electrons on the working electrodes, which induces the occurrence of the dark current to the electrolytes and thus leakage current significantly deteriorated the life-time of the DSSC. Reliable electrolyte additives diminishing the influences of water to the DSSCs degradation process becomes a critical issue in maintaining an acceptable cell life-time. In this work, the effects of four benzimidazole derivatives a-d as the electrolyte additives in the presence of water were comprehensively examined by time-dependent photovoltaic performance of the cells. As a result, open-circuit voltage (V{sub oc}), short-circuit current (J{sub sc}), efficiency ({eta}), and fill factor (FF) collected from I-V curves were studied. In addition, electrochemical impedance spectroscopy (EIS) technique was implemented to evaluate the effects of the charge-transfer resistance (R{sub ct}) at the interfaces between TiO{sub 2}/dye/electrolyte. Results showed that the bis-benzimidazole derivative c gives significant improvement in the long-term stability due to the effective protection of the ligands between dye and working electrodes from the attack by environmental water molecules. (author)

  14. (E-1,2-Bis(1-propyl-5,6-dimethyl-1H-benzimidazol-2-ylethene

    Directory of Open Access Journals (Sweden)

    Joseph A. Potenza

    2010-03-01

    Full Text Available In the title compound, C26H32N4, the essentially planar (r.m.s. deviations of 0.0053 and 0.0242 Å benzimidazole fragments are trans with respect to a central ethene fragment, and are canted in opposite directions by 2.78 (6 and 5.87 (6° with respect to the ethene plane, giving the molecule a propeller conformation. The terminal ethyl fragments of the pendant n-propyl groups protrude to either side of the benzimidazole planes. Overall, the molecule exhibits a pseudo-center of symmetry at the mid-point of the ethene fragment. Both π–π stacking and typical C—H...π interactions are notably absent, as are intermolecular hydrogen bonds. When viewed along the a axis, the structure appears as criss-crossed layers of molecules with the planar fragments separated along the c-cell direction by the protruding ethyl groups.

  15. Syntheses and molecular structures of novel Ru(II) complexes with bidentate benzimidazole based ligands and their catalytic efficiency for oxidation of benzyl alcohol

    Science.gov (United States)

    Dayan, Osman; Tercan, Melek; Özdemir, Namık

    2016-11-01

    Five bidentate ligands derived from quinoline-2-carboxylic acid, i.e. 2-(1H-benzimidazol-2-yl)quinoline (L1), 2-(1-benzyl-1H-benzimidazol-2-yl)quinoline (L2), 2-[1-(2,3,5,6-tetramethylbenzyl)-1H-benzimidazol-2-yl]quinoline (L3), 2-[1-(4-chlorobenzyl)-1H-benzimidazol-2-yl]quinoline (L4), and 2-[1-(4-methylbenzyl)-1H-benzimidazol-2-yl]quinoline (L5) were synthesized. Treatment of L1-5 with [RuCl2(p-cymene)]2 and KPF6 afforded six-coordinate piano-stool Ru(II) complexes, namely, [RuCl(L1)(p-cymene)]PF6 (C1), [RuCl(L2)(p-cymene)]PF6 (C2), [RuCl(L3)(p-cymene)]PF6 (C3), [RuCl(L4)(p-cymene)]PF6 (C4), and [RuCl(L5)(p-cymene)]PF6 (C5). Synthesized compounds were characterized with different techniques such as 1H and 13C NMR, FT-IR, and UV-vis spectroscopy. The solid state structure of L1 and C3 was confirmed by single-crystal X-ray diffraction analysis. The single crystal structure of C3 verified coordination of L3 to the Ru(II) center. The Ru(II) center has a pseudo-octahedral three legged piano stool geometry. The complexes C1-5 were tested as catalysts for the catalytic oxidation of benzyl alcohol to benzaldehyde in the presence of periodic acid (H5IO6) (Substrate/Catalyst/Oxidant = 1/0.01/0.5). The best result was obtained with C2 (3 h→90%).

  16. Odporność grzyba Botryotinia fuckeliana (De Bary Whetzel (Botrytis cinerea Pers. – patogena malin, truskawek i innych roślin uprawnych na fungicydy benzimidazolowe [Resistance of Botryotinia fuckeliana (De Bary Whetzel (Botrytis cinerea Pers. to benzimidazole fungicides

    Directory of Open Access Journals (Sweden)

    E. Arseniuk

    2015-06-01

    Full Text Available In the period 1975-1977 forms of the fungus Botrytis cinerea were found in Poland resistant to benzimidazole fungicides. The incidence of the resistant forms increases with the more intensive use of these fungicides. The resistance of Botrytis cinerea to benzimidazole compounds is a cross-resistance involving the whole group of these agents, nowithstanding wihich of them was applied. The resistance acquired by the fungus does not change its reaction to other prophylactic fungicides.

  17. Odporność grzyba Botryotinia fuckeliana (De Bary) Whetzel (Botrytis cinerea Pers.) – patogena malin, truskawek i innych roślin uprawnych na fungicydy benzimidazolowe [Resistance of Botryotinia fuckeliana (De Bary) Whetzel (Botrytis cinerea Pers.) to benzimidazole fungicides

    OpenAIRE

    E. Arseniuk; H. Bryk

    2015-01-01

    In the period 1975-1977 forms of the fungus Botrytis cinerea were found in Poland resistant to benzimidazole fungicides. The incidence of the resistant forms increases with the more intensive use of these fungicides. The resistance of Botrytis cinerea to benzimidazole compounds is a cross-resistance involving the whole group of these agents, nowithstanding wihich of them was applied. The resistance acquired by the fungus does not change its reaction to other prophylactic fungicides.

  18. Microwave-assisted synthesis of new pyrimido[4′,5′:4,5]thiazolo[3,2-a] benzimidazol-4(3H)-one derivatives in solvent-free condition

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Microwave-assisted synthesis of new 2-arylpyrimido[4′,5′:4,5]thiazolo[3,2-a]benzimidazol-4(3H)-ones from 3-aminothiazolo[3,2-a]benzimidazol-2-carboxamide and aroyl halides in solvent-free condition is described. In comparison with classical conditions the reactions are faster and the yields are higher under microwave irradiation.

  19. Benzimidazole-resistant gastrointestinal nematodes in indigenous Chiapas and Pelibuey sheep breeds from Chiapas, Mexico.

    Science.gov (United States)

    Liébano-Hernández, E; González-Olvera, M; Vázquez-Peláez, C; Mendoza-de-Gives, P; Ramírez-Vargas, G; Peralta-Lailson, M; Reyes-García, M E; Osorio, J; Sánchez-Pineda, H; López-Arellano, M E

    2015-01-01

    Because of the natural adaptation of Mexican sheep, the aim of the present study was to identify the presence or absence of gastrointestinal parasitic nematodes (GIN) resistant to benzimidazole (BZ) in both Chiapas and Pelibuey sheep breeds on local farms. Both male and female GIN-infected grazing sheep of the two breeds were selected. Sheep faecal samples were collected to obtain infective larvae (L3). This evolving stage of the parasite was used for taxonomic identification of the genus, based on its morphological characteristics. BZ anthelmintic resistance was evaluated using a nematode-compound in vitro interaction bioassay and the allele-specific polymerase chain reaction technique to detect mutations of residues 198 and 200 on isotype 1 of the β-tubulin gene. Three BZ-based compounds (febendazole (FBZ), tiabendazole (TBZ) and albendazole (ABZ)) at concentrations of 1, 0.5, 0.25, 0.125, 0.062 and 0.03 mg/ml were used to estimate the anthelmintic efficacy and lethal dose (LD50, LD90 and LD99) of the drugs. Two parasitic nematodes, Haemonchus and Teladorsagia, were identified in both isolates. Also, the proportions of anthelmintic resistance identified in GIN of the two sheep breeds were 68% in isolates from the Chiapas breed and 71.8% in the Pelibuey breed. The specific lethal activity obtained with FBZ was higher than 90%. However, TBZ and ABZ showed a lethal activity lower than 50%. High variability in the discriminating dose values was found among the BZ drugs. For example, FBZ LD ranged from 0.01 to 1.20 mg/ml; on the other hand, TBZ and ABZ required a dose ranging from 0.178 to 759 mg/ml. In addition, amino acid changes of Phe (TTC) to Tyr (TAC) at codon 200 of the β-tubulin gene, showing resistance to BZ, and no changes at codon 198 Glu (GAA) to Ala (GCA) were observed for both isolates. These results confirmed the presence of a genetic mutation associated with BZ in both Chiapas and Pelibuey nematode isolates.

  20. Synthesis, interaction with DNA and antiproliferative activities of two novel Cu(II) complexes with Schiff base of benzimidazole

    Science.gov (United States)

    Song, Wen-Ji; Cheng, Jian-Ping; Jiang, Dong-Hua; Guo, Li; Cai, Meng-Fei; Yang, Hu-Bin; Lin, Qiu-Yue

    2014-03-01

    Two novel copper(II) complexes with Schiff base of benzimidazole [Cu(L)Cl]2·CH3OH have been synthesized. HL1 (N-(benzimidazol-2-ymethyl)-5-chlorosalicylideneimine, C15H11ClN3O) and HL2 (N-(benzimidazol-2-ymethyl)-salicylideneimine, C15H12N3O) are ligands of complex (1) and complex (2), respectively. The complexes were characterized by elemental analysis, IR, UV-Vis, TGA and X-ray diffraction. Within the complexes, Cu(II) ions were four coordinated by two nitrogen atom of azomethine and imine, one phenolic oxygen atom from HL and one chloride atom. A distorted quadrilateral structure was formed. Complex (1) crystallized in the triclinic crystal system. Results showed that π-π stacking effect occurred due to the existence of aromatic ring from Schiff base and hydrogen bonding between methanol and adjacent atoms. The DNA binding properties of the complexes were investigated by electronic absorption spectra, fluorescence spectra and viscosity measurements. Results indicated that complexes bound to DNA via partial intercalation mode. The DNA binding constants Kb/(L mol-1) were 1.81 × 104 (1), 1.37 × 104 (2), 6.27 × 103 (HL1) and 3.14 × 103 (HL2) at 298 K. The title complexes could quench the emission intensities of EB-DNA system significantly. The results of agarose gel electrophoresis indicated complex (1) could cleave supercoiled DNA through the oxidative mechanism. The inhibition ratios revealed that complex (1) and HL1 had strong antiproliferative activities against human breast cancer cells (MCF-7) lines and human colorectal cancer cells (COLO205) lines in vitro. The antiproliferative activities of complex (1) against MCF-7 lines (IC50 = 16.9 ± 1.5 μmol L-1) and against COLO205 lines (IC50 = 16.5 ± 3.4 μmol L-1) is much stronger than that of HL1, which had the potential to develop anti-cancer drug.

  1. Synthesis, Structure and Biological Activity of Zn(II) Complex with Tris(benzimidazol-2-yl-methyl)amine Ligand

    Institute of Scientific and Technical Information of China (English)

    LIU,Xiao-Lan(刘小兰); ZHAO,Ru(赵茹); LIU,Xiao-Hong(刘晓红); YUE,Jun-Jie(岳俊杰); YIN,Yu-Xin(尹宇新); SUN,Yun(孙云); SUN,Ming(孙命)

    2004-01-01

    A new Zn(II) mononuclear complex with tris(benzimidazol-2-yl-methyl)amine (NTB) was synthesized with stoichiometry of [Zn(NTB)NO3]NO3·DIPY·DMF (DIPY∶4,4'-dipyridyl). The complex was characterized by elemental analysis, UV and IR spectra. The crystal structure was determined by using X-ray diffraction analysis. The crystal structure indicates that four N atoms and one O atom coordinate to zinc ion to construct a distorted trigonal-dipyramid configuration. Three nonprotonated N atoms from imidazole groups are in the equatorial plane, one alkylamino N atom and one O atom from in the axial directions. The biological activity assay shows that this complex presents certain biological activity by means of pyrogallol autoxidation and it can be called a model compound of superoxide dismutase (SOD).

  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. HALF-TITANOCENE CHLORIDES 2-(BENZIMIDAZOL-2-YL)QUINOLIN-8-OLATES: SYNTHESIS, CHARACTERIZATION AND ETHYLENE (CO-)POLYMERIZATION BEHAVIOR

    Institute of Scientific and Technical Information of China (English)

    Wen-juan Zhang; Wei Huang; Tong-ling Liang; Wen-hua Sun

    2013-01-01

    A series of half-titanocene chloride 2-(benzimidazol-2-yl)quinolin-8-olates C1-C6 were synthesized by treating the lithium salts of the ligand with CpTiC13.All the complexes were characterized by 1H-NMR,13C-NMR and elemental analyses,and the crystal structure of C3 and C6 was measured by X-ray.These half-titanocene complexes showed moderate catalytic activities toward ethylene polymerization (up to 1840 kg·mol-1(Ti)·h-1) when activated with MMAO,affording the high molecular weight polymers.And they also exhibited good activity for copolymerization of ethylene and α-olefin with low content of co-monomer.

  4. Synthesis and Luminescence Properties of Three High-dimensional Coordination Polymers: Zn(Ⅱ) with Imidazole or Benzimidazole Ligand

    Institute of Scientific and Technical Information of China (English)

    ZHANG Zhong-qiang; ZHANG Jing; DONG Lan-jun; ZHU Qin-lei; HUANG Ru-dan

    2009-01-01

    A novel 2D coordination polymer [Zn2(bim)4]n(1)(Hbim=benzimidazole) based on dihydrated- [N,N'-bis(2-aminophenl)-oxalamide](L1·2H2O) with zinc nitrate has been synthesized. Previously we have synthe- sized complexes [In2Zn3(im)12]n(2)(Him= imidazole) and [Zn(im)2]n(3) successfully. In complex 1, each Zn(Ⅱ) coor-dinated with four ligands adopts a distorted tetrahedron coordination mode, and the 2D grid structure is built by the Zn(bim)4 as the secondary building unit(SBU). The luminescence properties of the three complexes were investigated for the first time. The emissions with maxima for complexes 1, 2 and 3 are at 379, 469 and 392 nm, respectively.

  5. Investigation of the apoptotic pathway induced by benzimidazole-oxindole conjugates against human breast cancer cells MCF-7.

    Science.gov (United States)

    Lakshma Nayak, Vadithe; Nagaseshadri, Bobburi; Vishnuvardhan, M V P S; Kamal, Ahmed

    2016-07-15

    In our previous studies, benzimidazole-oxindole conjugates were synthesized and evaluated by National Cancer Institute (NCI) for their cytotoxic activity and the new molecules like 5c and 5p were considered as potential leads. These conjugates arrested the cell cycle at G2/M phase and inhibited tubulin polymerization. These observations prompted us to investigate the apoptotic mechanism induced by these lead molecules against human breast cancer cells (MCF-7). Studies like measurement of mitochondrial membrane potential (ΔΨm), generation of reactive oxygen species (ROS) and Annexin V-FITC assay revealed that these compounds induced mitochondrial mediated (intrinsic apoptotic pathway) apoptosis in human breast cancer cells. It was further confirmed by western blot analysis of pro apoptotic protein Bax, anti apoptotic protein Bcl-2, cytochrome c release, caspase-9 activity and cleavage of PARP. PMID:27262596

  6. An efficient synthesis of 3'-indolyl substituted pyrido[1,2-]benzimidazoles as potential antimicrobial and antioxidant agents

    Indian Academy of Sciences (India)

    Harshad G Kathrotiya; Manish P Patel

    2013-09-01

    A new class of indole-based pyrido[1,2-]benzimidazole derivatives 4a-r have been synthesized by one-pot cyclocondensation reaction of 2-phenyl-1-indole-3-carboxaldehyde 1a-i, malononitrile 2 and 2-cyanomethylbenzimidazole 3a-b in the presence of catalytic amount of NaOH. In vitro antimicrobial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically three Gram-positive bacteria (Streptococcus pneumoniae, Clostridium tetani, Bacillus subtilis), three Gram-negative bacteria (Salmonella typhi, Vibrio cholerae, Escherichia coli) and two fungi (Aspergillus fumigatus, Candida albicans) using broth microdilution MIC (minimum inhibitory concentration) method. In vitro antioxidant activity was evaluated by ferric-reducing antioxidant power (FRAP) assay method. Compounds 4c, 4e, 4l and 4q have been found to be most efficient antimicrobial members while compounds 4h and 4p possess better ferric reducing antioxidant power.

  7. Effect of two formulations of benzimidazole carbamates on the viability of cysts of Echinococcus granulosus in vivo

    Directory of Open Access Journals (Sweden)

    Daniel-Mwuambete K.

    2003-12-01

    Full Text Available Two different preparations, solution and suspension, of three benzimidazole carbamate drugs, mebendazole, albendazole and ricobendazole, were compared by analyzing their in vivo activity against Echinococcus granulosus cysts in a mouse model. Polyvinylpyrrolidone was used for the elaboration of drug solutions and these formulations manifested better results in terms of reduction of number of viable hydatid cysts in mice than the reference drug suspensions. The effect was more prominent on mebendazole-treated mice, at doses of 25-50 mg/kg. There was a correlation between ED50 and pharmacokinetical parameters of AUC0∞ and Cmax , showing that a significant improvement on solubility affects the in vivo activity of these drugs.

  8. Effect of two formulations of benzimidazole carbamates on the viability of cysts of Echinococcus granulosus in vivo.

    Science.gov (United States)

    Daniel-Mwuambete, K; Ponce-Gordo, F; Torrado, J; Torrado, S; Cuesta-Bandera, C

    2003-12-01

    Two different preparations, solution and suspension, of three benzimidazole carbamate drugs, mebendazole, albendazole and ricobendazole, were compared by analyzing their in vivo activity against Echinococcus granulosus cysts in a mouse model. Polyvinylpyrrolidone was used for the elaboration of drug solutions and these formulations manifested better results in terms of reduction of number of viable hydatid cysts in mice than the reference drug suspensions. The effect was more prominent on mebendazole-treated mice, at doses of 25-50 mg/kg. There was a correlation between ED50 and pharmacokinetical parameters of AUC0-infinity and Cmax, showing that a significant improvement on solubility affects the in vivo activity of these drugs. PMID:14710635

  9. Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor–acceptor–donor type polymers

    International Nuclear Information System (INIS)

    A new benzimidazole unit, 4′-(tert-butyl)spiro[benzo[d]imidazole-2,1′-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor–acceptor–donor (D–A–D) type monomers, 4′-(tert-butyl)-4,7-bis(4-hexylthiophen-2-yl) spiro[benzo[d]imidazole-2,1′-cyclohexane] (BIHT) and 4′-(tert-butyl)-4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl) spiro[benzo[d]imidazole-2,1′-cyclohexane] (BIED) were electrochemically polymerized, their electrochemical and optical properties were investigated by cyclic voltammetry, UV–vis-NIR spectroscopy techniques. Effect of donor groups on the optical and electronic properties of polymer was studied.

  10. Low power optical limiting studies on nanocrystalline benzimidazole thin films prepared by modified liquid phase growth technique

    Indian Academy of Sciences (India)

    P A Praveen; S P Prabhakaran; R Ramesh Babu; K Sethuraman; K Ramamurthi

    2015-06-01

    In the present work, benzimidazole (BMZ), a well known nonlinear optical material, thin films were deposited using the modified liquid phase growth technique at different solution temperatures. The prepared samples were subjected to spectral, structural and surface analyses. Linear optical properties and third-order optical nonlinearity of the deposited BMZ thin films were analysed using UV–visible–NIR spectrum and -scan technique, respectively. The experimental results show that the BMZ films exhibit reverse saturable absorption and positive nonlinearity at 650 nm CW laser of power 5 mW. The measured third-order nonlinear susceptibility of the films is about 10−10 esu. Optical limiting studies were performed using the same laser source and the potentiality of the BMZ films is reported.

  11. Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents.

    Science.gov (United States)

    Zhang, Ling; Addla, Dinesh; Ponmani, Jeyakkumar; Wang, Ao; Xie, Dan; Wang, Ya-Nan; Zhang, Shao-Lin; Geng, Rong-Xia; Cai, Gui-Xin; Li, Shuo; Zhou, Cheng-He

    2016-03-23

    A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 μM concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities.

  12. Synthesis, crystal structure and forming mechanism of two novel copper (Ⅱ) α-methacrylate complexes with benzimidazole

    Institute of Scientific and Technical Information of China (English)

    王尧宇; 时茜; 杨秉勤; 史启祯; 高忆慈; 周忠远

    1999-01-01

    Two copper (Ⅱ) a-methacrylate complexes with benzimidazole, Cu [CH2=C( CH3)-COO]2(C7H6N2)2(1) and Cu2 [CH2=C(CH3)-COO]4(C7H6N2)2 (2), have been prepared and characterized by elemental analyses, IR and electronic reflectance spectroscopies. The single crystal X-ray diffraction study of the two complexes shows that complex 1 has a square planar configuration, while complex 2 has a binuclear cage structure. The crystal structural analyses show that both complexes 1 and 2 are monoclinic, with space group P21/c, a=0.924 16(8) nm, b=1.233 02(13) nm, c =0.989 1(3) nm, β=91.912(13)°, Dc=1.386 g/cm3, Z=2, R=0.033 9 for the former; and a=0.905 7(2) nm, b=2.252 1(5) nm, c=1.623 5(4) nm, β=90.11(2)°, Dc =1.411 g/cm3 , Z=4, R=0.056 8, Cu-Cu=0.266 21 nm for the latter. Different structural types of complexes 1 and 2 were produced simultaneously in the reaction of copper (Ⅱ) α-methacrylate with benzimidazole in methanol solution. The forming mechanism of the complexes has been summarized.

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

    Science.gov (United States)

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

    2016-05-23

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

  14. A Green Route for the One-Pot Synthesis of 1,2-Disubstituted Benzimidazoles Using Iron(Ill) Phosphate under Solventless Conditions%A Green Route for the One-Pot Synthesis of 1,2-Disubstituted Benzimidazoles Using Iron(Ill) Phosphate under Solventless Conditions

    Institute of Scientific and Technical Information of China (English)

    Behbahani, F.K.; Ziaei, Parisa

    2012-01-01

    1,2-Disubstituted benzimidazoles are selectively synthesized in high yields under extremely mild conditions via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of iron(Ⅲ) phosphate under solventfree conditions. The use of readily available iron(Ⅲ) phosphate as a reusable and recyelable catalyst makes this process quite simple, convenient, and environment-friendly.

  15. Benzimidazole covalent probes and the gastric H+/K+-ATPase as a model system for protein labeling in a copper-free setting

    Science.gov (United States)

    Paresi, Chelsea J.; Liu, Qi; Li, Yue-Ming

    2016-01-01

    Affinity probes are useful tools for determining molecular targets and elucidating mechanism of action for novel, bioactive compounds. In the case of covalent inhibitors, activity based probes are particularly valuable for ensuring acceptable selectivity margins. However, there is a variety of bioorthogonalchemisty reactions available for modifying compounds of interest with clickable tags. Here, we describe a direct comparison of tetrazine ligation and strain promoted azide-alkyne cycloaddition using benzimidazole based probes to bind their known target, the gastric proton pump, ATP4A. This study validates the use of chemical probes for target identification and illustrates the superior efficiency of tetrazine ligation for copper-free click systems. In addition, we have identified several novel binding partners of benzimidazole probes: Isoform 2 of deleted in malignant brain tumors 1 protein (DMBT1) and three uncharacterized proteins. PMID:26952080

  16. Synthesis of some novel phosphorylated and thiophosphorylated benzimidazoles and benzothiazoles and their evaluation for larvicidal potential to Aedes albopictus and Culex quinquefasciatus.

    Science.gov (United States)

    Bandyopadhyay, Prabal; Sathe, Manisha; Tikar, Sachin N; Yadav, Ruchi; Sharma, Pratibha; Kumar, Ashok; Kaushik, M P

    2014-07-01

    Series of benzimidazole and benzothiazole linked phosphoramidates and phosphoramidothioates (5a-j) and benzimidazole linked phenylphosphoramidates and phenylphosphoramidothioates (10a-e) were synthesized. The title compounds were preliminary screened for mosquito larvicidal properties against Aedes albopictus and Culex quinquefasciatus at different concentration from 40 to 5 mg/L. Among the screened compounds three compounds revealed potential larvicidal effects with 100% mortality in the order of 10e>5j>5e. Compound 10e was found to be the most toxic compound to Ae. albopictus and Cx. quinquefasciatus. The LC50 of 10e against Ae. albopictus was found to be 6.42 and 5.25 mg/L at 24 and 48 h, respectively, whereas it was 7.01 and 3.88 mg/L, respectively in Cx. quinquefasciatus. Temephos was used as positive control. PMID:24857290

  17. 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.

  18. Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

    Energy Technology Data Exchange (ETDEWEB)

    Koc, Ziya Erdem, E-mail: zerdemkoc@gmail.com [Department of Chemistry, Faculty of Science, Selcuk University, 42031 Konya (Turkey); Bingol, Haluk; Saf, Ahmet O. [Department of Chemistry, Faculty of Science, Selcuk University, 42031 Konya (Turkey); Torlak, Emrah [Provincial Control Laboratory, Konya (Turkey); Coskun, Ahmet [Department of Chemistry, Faculty of Science, Selcuk University, 42031 Konya (Turkey)

    2010-11-15

    Four new tripodal-benzimidazole derivatives were synthesized by Schiff base reaction between 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) and different diamine derivatives. The structures of the obtained compounds were identified by FT-IR, {sup 1}H NMR, {sup 13}C NMR and UV-vis spectral data, thermal analysis and elemental analysis. Electrochemical behaviors of the compounds were studied by cyclic voltammetry in DMF including 0.1 M [NBu{sub 4}] [PF{sub 6}]. The voltammograms showed peaks having similar characteristics except tripodal-benzimidazole including -NO{sub 2} derivative. In addition, their antimicrobial activities were evaluated by using the standard disk diffusion method in dimethylformamide media. The activities were determined against 4 bacteria cultures by comparing to those of gentamycin.

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

    Science.gov (United States)

    Vahdat, Seyed Mohammad; Baghery, Saeed

    2013-09-01

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

  20. Comparison of in vitro methods and faecal egg count reduction test for the detection of benzimidazole resistance in small strongyles of horses.

    Science.gov (United States)

    Königová, A; Várady, M; Corba, J

    2003-05-01

    The objective of the study was to compare the in vitro egg hatch test (EHT), larval development test (LDT) and in vivo faecal egg count reduction test (FECR test) for the detection of benzimidazole resistance in equine strongyles. The presence of resistant or susceptible strongyle populations was determined in 25 stud farms using the in vivo FECR test and in vitro EHT. On the basis of the FECR values, resistance to fenbendazole was detected on 15 of the 25 farms (60%). The ED50 value (anthelmintic concentration producing 50% inhibition of hatching) for suspected resistant populations varied from 0.110 to 0.222 microg/ml thiabendazole (TBZ). Final LD50 values (anthelmintic concentration inhibiting development of 50% of eggs into L3 infective larvae) above 0.029 microg/ml TBZ in the in vitro larval development test on samples from 11 stud farms revealed the presence of populations of small strongyles suspected of being benzimidazole-resistant.

  1. Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

    International Nuclear Information System (INIS)

    Four new tripodal-benzimidazole derivatives were synthesized by Schiff base reaction between 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) and different diamine derivatives. The structures of the obtained compounds were identified by FT-IR, 1H NMR, 13C NMR and UV-vis spectral data, thermal analysis and elemental analysis. Electrochemical behaviors of the compounds were studied by cyclic voltammetry in DMF including 0.1 M [NBu4] [PF6]. The voltammograms showed peaks having similar characteristics except tripodal-benzimidazole including -NO2 derivative. In addition, their antimicrobial activities were evaluated by using the standard disk diffusion method in dimethylformamide media. The activities were determined against 4 bacteria cultures by comparing to those of gentamycin.

  2. Effect of alcohols on separation behavior of rare earth elements using benzimidazole-type anion-exchange resin in nitric acid solutions

    International Nuclear Information System (INIS)

    Chromatographic separation experiments of trivalent rare earth elements were performed using benzimidazole type anion-exchange resin in nitric/alcohol mixed solvent systems at room temperature. As a result, it was found those trivalent rare earth elements are able to be separated mutually in a 20% HNO3 and 80% MeOH mixed solvent. Based on these results, we systematically examined using various alcohols to make clear the role of alcohols in anion-exchange reactions at various temperatures. (author)

  3. Mechanism of Action and Antiviral Activity of Benzimidazole-Based Allosteric Inhibitors of the Hepatitis C Virus RNA-Dependent RNA Polymerase

    OpenAIRE

    Tomei, Licia; Altamura, Sergio; Bartholomew, Linda; Biroccio, Antonino; Ceccacci, Alessandra; Pacini, Laura; Narjes, Frank; Gennari, Nadia; Bisbocci, Monica; Incitti, Ilario; Orsatti, Laura; Harper, Steven; Stansfield, Ian; Rowley, Michael; De Francesco, Raffaele

    2003-01-01

    The RNA-dependent RNA polymerase of hepatitis C virus (HCV) is the catalytic subunit of the viral RNA amplification machinery and is an appealing target for the development of new therapeutic agents against HCV infection. Nonnucleoside inhibitors based on a benzimidazole scaffold have been recently reported. Compounds of this class are efficient inhibitors of HCV RNA replication in cell culture, thus providing attractive candidates for further development. Here we report the detailed analysis...

  4. Xanthan Sulfuric Acid: An Efficient Bio-supported and Recy- clable Solid Acid Catalyst for the Synthesis of 2-Aryl Thiadiazolo Benzimidazoles

    Institute of Scientific and Technical Information of China (English)

    Kuarm, B. Suresh; Janardan, B.; Crooks, Peter A.; Rajitha, B.

    2012-01-01

    Xanthan sulfuric acid is an efficient solid acid catalyst for the preparation of 2-aryl benzimidazoles in excellent yields. This method is applicable for the reaction of benzo[c][ 1,2,5]thiadiazole-4,5-diamine with aldehydes by sim- ple physical grinding at room temperature. The salient features of the present methodology is cheaper process, easy synthesis of stable catalyst and the catalyst can be easily recycled without significant loss of activity.

  5. Structure-Bioactivity Relationship for Benzimidazole Thiophene Inhibitors of Polo-Like Kinase 1 (PLK1, a Potential Drug Target in Schistosoma mansoni.

    Directory of Open Access Journals (Sweden)

    Thavy Long

    2016-01-01

    Full Text Available Schistosoma flatworm parasites cause schistosomiasis, a chronic and debilitating disease of poverty in developing countries. Praziquantel is employed for treatment and disease control. However, its efficacy spectrum is incomplete (less active or inactive against immature stages of the parasite and there is a concern of drug resistance. Thus, there is a need to identify new drugs and drug targets.We show that RNA interference (RNAi of the Schistosoma mansoni ortholog of human polo-like kinase (huPLK1 elicits a deleterious phenotypic alteration in post-infective larvae (schistosomula or somules. Phenotypic screening and analysis of schistosomula and adult S. mansoni with small molecule inhibitors of huPLK1 identified a number of potent anti-schistosomals. Among these was a GlaxoSmithKline (GSK benzimidazole thiophene inhibitor that has completed Phase I clinical trials for treatment of solid tumor malignancies. We then obtained GSKs Published Kinase Inhibitor Sets (PKIS 1 and 2, and phenotypically screened an expanded series of 38 benzimidazole thiophene PLK1 inhibitors. Computational analysis of controls and PLK1 inhibitor-treated populations of somules demonstrated a distinctive phenotype distribution. Using principal component analysis (PCA, the phenotypes exhibited by these populations were mapped, visualized and analyzed through projection to a low-dimensional space. The phenotype distribution was found to have a distinct shape and topology, which could be elicited using cluster analysis. A structure-activity relationship (SAR was identified for the benzimidazole thiophenes that held for both somules and adult parasites. The most potent inhibitors produced marked phenotypic alterations at 1-2 μM within 1 h. Among these were compounds previously characterized as potent inhibitors of huPLK1 in cell assays.The reverse genetic and chemical SAR data support a continued investigation of SmPLK1 as a possible drug target and/or the prosecution of

  6. The pH dependence of the mutagenicity of methyl benzimidazol-2-yl carbamate (MBC) towards Aspergillus nidulans (Eidam) Winter and Cladosporium cucumerinum Ellis & Arth.

    Science.gov (United States)

    Nirenberg, H I; Speakman, J B

    1981-01-01

    The ability of methyl benzimidazol-2-yl carbamate (MBC) to induce point mutations to carboxin and MBC resistance in Aspergillus nidulans (Eidam) Winter and Cladosporium cucumerinum Ellis & Arth. was dependent upon the pH value of the agar medium into which it had been incorporated. The relevance of this in relation to testing chemicals for a possible mutagenic activity with microorganisms is discussed. PMID:7010148

  7. Ultrasound promoted and SiO2/CCl3COOH mediated synthesis of 2-aryl-1-arylmethyl-1-benzimidazole derivatives in aqueous media: An eco-friendly approach

    Indian Academy of Sciences (India)

    Brajesh Kumar; Kumari Smita; Brajendra Kumar; Luis Cumbal

    2014-11-01

    Ultrasonic irradiation is an efficient and innocuous technique of reagent activation for synthesizing organic compounds. First one-pot synthesis of 2-aryl-1-arylmethyl-1H- benzimidazole derivatives from o- phenylenediamine and an aromatic aldehyde in the presence of silica gel supported trichloroacetic acid (SiTCA) was carried out with excellent yields at 50°C by sonication. This method provided several advantages such as green solvent, inexpensive catalyst, simple experimental methodology, shorter reaction time and higher yield.

  8. Preparation of stir cake sorptive extraction based on polymeric ionic liquid for the enrichment of benzimidazole anthelmintics in water, honey and milk samples.

    Science.gov (United States)

    Wang, Yulei; Zhang, Jie; Huang, Xiaojia; Yuan, Dongxing

    2014-08-20

    In this work, a new stir cake sorptive extraction (SCSE) using polymeric ionic liquid monolith as sorbent was prepared. The sorbent was obtained by in situ copolymerization of an ionic liquid, 1-allyl-3-methylimidazolium bis[(trifluoro methyl)sulfonyl]imide (AMII) and divinylbenzene (DB) in the presence of N,N-dimethylformamide. The influence of the content of ionic liquid and the porogen in the polymerization mixture on extraction performance was studied thoroughly. The physicochemical properties of the polymeric ionic liquid were characterized by infrared spectroscopy, elemental analysis, scanning electron microscopy and mercury intrusion porosimetry. The usefulness of SCSE-AMIIDB was demonstrated by the enrichment of trace benzimidazole anthelmintics. Several parameters affecting the extraction efficiency were investigated, and under the optimized conditions, a simple and effective method for the determination of trace benzimidazoles residues in water, milk and honey samples was established by coupling SCSE-AMIIDB with high performance liquid chromatography/diode array detection (SCSE-AMIIDB-HPLC/DAD). Results indicated that the limits of detection (S/N=3) for target compounds were 0.020-0.072 μg L(-1), 0.035-0.10 μg L(-1) and 0.026-0.076 μg L(-1) in water, milk and honey samples, respectively. In addition, an acceptable reproducibility was achieved by evaluating the repeatability and intermediate precision with relative standard deviations (RSD) of less than 9% and 11%, respectively. Finally, the established AMII-SCSE-HPLC/DAD method was successfully applied for the determination of benzimidazoles residues in milk, honey and environmental water samples. Recoveries obtained for the determination of benzimidazole anthelmintics in spiking samples ranged from 70.2% to 117.6%, with RSD below 12% in all cases.

  9. Synthesis of a novel series of 4-arylpiperazinyl derivatives linked to a 2-(pyridin-3-yl)-1H-benzimidazole as new Delavirdine analogues

    Energy Technology Data Exchange (ETDEWEB)

    Pessoa-Mahana, David; Nunez, Andres; Espinosa, Christian; Mella-Raipn, Jaime [Pontificia Universidad Catolica de Chile, Santiago (Chile). Facultad de Quimica. Dept. de Farmacia; Pessoa-Mahana, Hernan [Universidad de Chile, Santiago (Chile). Facultad de Ciencias Quimicas. Dept. de Quimica Organica y Fisico-Quimica

    2010-07-01

    The synthesis of a series of substituted arylpiperazines linked to a 2-(pyridin-3-yl)-1H-benzo[d]imidazole scaffold through an alkylic linker is reported. The novel 1-(2-(4-arylpiperazin-1-yl)alkyl)-2-(pyridin-3-yl)-1H-benzimidazole derivatives are structurally related to the anti-HIV-1 drug Delavirdine and belong to the bis(heteroaryl)piperazines family (BHAPs), a well known HIV-1 reverse transcriptase inhibitors group. (author)

  10. [Complexation du 2-[(5-méthylpyrazolyl)méthyle]benzimidazole par les chlorures de cuivre et de cadmium].

    Science.gov (United States)

    Sbai, F; Regragui, R; Essassi, E; Kenz, A; Pierrot, M

    2003-08-01

    The structures of dichloro[2-[(5-methyl-1H-pyrazol-3-yl-kappaN(2))methyl]-1H-1,3-benzimidazole-kappaN(3)]copper(II), [CuCl(2)(C(12)H(12)N(4))], and di-mu-chloro-bis(chloro[2-[(5-methyl-1H-pyrazol-3-yl-kappaN(2))methyl]-1H-1,3-benzimidazole-kappaN(3)]cadmium(II)), [Cd(2)Cl(4)(C(12)H(12)N(4))(2)], show that these compounds have the structural formula [ML(Cl)(2)](n), where L is 2-[(5-methylpyrazolyl)methyl]benzimidazole. When M is copper, the complex is a monomer (n = 1), with a tetrahedral coordination for the Cu atom. When M is cadmium (n = 2), the complex lies about an inversion centre giving rise to a centrosymmetric dimer in which the Cd atoms are bridged by two chloride ions and are pentacoordinated.

  11. [Complexation du 2-[(5-méthylpyrazolyl)méthyle]benzimidazole par les chlorures de cuivre et de cadmium].

    Science.gov (United States)

    Sbai, F; Regragui, R; Essassi, E; Kenz, A; Pierrot, M

    2003-08-01

    The structures of dichloro[2-[(5-methyl-1H-pyrazol-3-yl-kappaN(2))methyl]-1H-1,3-benzimidazole-kappaN(3)]copper(II), [CuCl(2)(C(12)H(12)N(4))], and di-mu-chloro-bis(chloro[2-[(5-methyl-1H-pyrazol-3-yl-kappaN(2))methyl]-1H-1,3-benzimidazole-kappaN(3)]cadmium(II)), [Cd(2)Cl(4)(C(12)H(12)N(4))(2)], show that these compounds have the structural formula [ML(Cl)(2)](n), where L is 2-[(5-methylpyrazolyl)methyl]benzimidazole. When M is copper, the complex is a monomer (n = 1), with a tetrahedral coordination for the Cu atom. When M is cadmium (n = 2), the complex lies about an inversion centre giving rise to a centrosymmetric dimer in which the Cd atoms are bridged by two chloride ions and are pentacoordinated. PMID:12909760

  12. Novel Ni(II) and Zn(II) complexes coordinated by 2-arylaminomethyl-1H-benzimidazole: Molecular structures, spectral, DFT studies and evaluation of biological activity

    Science.gov (United States)

    Abdel-Ghani, Nour T.; Abo El-Ghar, Maha F.; Mansour, Ahmed M.

    2013-03-01

    [NiL1,2Cl2(OH2)3]·zH2O and [ZnL1,2(CH3CO2)2] (L1 = (1H-benzimidazol-2-ylmethyl)-N-phenyl amine, z = 0 and L2 = 2-[(1H-Benzimidazol-2-ylmethyl)-amino]-benzoic acid methyl ester, z = 1) complexes have been synthesized and characterized by a variety of physico-chemical techniques. The central Ni(II) ion is coordinated by only the pyridine-type nitrogen (Npy) of benzimidazole ring, three water molecules and two chlorido ligands forming a distorted octahedral geometry. Five coordinated zinc complexes were obtained, where the coordination sphere of zinc ion is made up of secondary amino group (NHsec), Npy and two acetate groups, one acts as a unidentate and the other as a bidentate. A theoretical DFT/UB3LYP method combined with LANL2DZ basis set shows that all the metal-ligand bonds are of the L → M type. Electronic structures have been calculated using TD-DFT method. The antibacterial activity of NiL2 complexes decreases by the introduction of COOCH3 group in the ortho-position of the aniline moiety.

  13. Preparation of stir cake sorptive extraction based on polymeric ionic liquid for the enrichment of benzimidazole anthelmintics in water, honey and milk samples

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Yulei [State Key Laboratory of Marine Environmental Science, Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystem, College of the Environment and Ecology, Xiamen University, Siming Road, P.O. Box 1009, Xiamen 361005 (China); Zhang, Jie [Key Lab of Urban Environment and Health, Institute of Urban Environment, Chinese Academy of Sciences (China); Huang, Xiaojia, E-mail: hxj@xmu.edu.cn [State Key Laboratory of Marine Environmental Science, Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystem, College of the Environment and Ecology, Xiamen University, Siming Road, P.O. Box 1009, Xiamen 361005 (China); Yuan, Dongxing [State Key Laboratory of Marine Environmental Science, Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystem, College of the Environment and Ecology, Xiamen University, Siming Road, P.O. Box 1009, Xiamen 361005 (China)

    2014-08-20

    Highlights: • A new polymeric ionic liquid-based monolith was prepared. • The monolith was used as the extractive medium of stir cake sorptive extraction. • The SCSE–AMIIDB can extract benzimidazole anthelmintics (BAs) effectively. • A combination of SCSE–AMIIDB–LD–HPLC/DAD was developed. • The combination was applied to monitor trace BAs in water, milk and honey samples. - Abstract: In this work, a new stir cake sorptive extraction (SCSE) using polymeric ionic liquid monolith as sorbent was prepared. The sorbent was obtained by in situ copolymerization of an ionic liquid, 1-allyl-3-methylimidazolium bis[(trifluoro methyl)sulfonyl]imide (AMII) and divinylbenzene (DB) in the presence of N,N-dimethylformamide. The influence of the content of ionic liquid and the porogen in the polymerization mixture on extraction performance was studied thoroughly. The physicochemical properties of the polymeric ionic liquid were characterized by infrared spectroscopy, elemental analysis, scanning electron microscopy and mercury intrusion porosimetry. The usefulness of SCSE–AMIIDB was demonstrated by the enrichment of trace benzimidazole anthelmintics. Several parameters affecting the extraction efficiency were investigated, and under the optimized conditions, a simple and effective method for the determination of trace benzimidazoles residues in water, milk and honey samples was established by coupling SCSE–AMIIDB with high performance liquid chromatography/diode array detection (SCSE–AMIIDB–HPLC/DAD). Results indicated that the limits of detection (S/N = 3) for target compounds were 0.020–0.072 μg L{sup −1}, 0.035–0.10 μg L{sup −1} and 0.026–0.076 μg L{sup −1} in water, milk and honey samples, respectively. In addition, an acceptable reproducibility was achieved by evaluating the repeatability and intermediate precision with relative standard deviations (RSD) of less than 9% and 11%, respectively. Finally, the established AMII

  14. Antibacterial activity of benzimidazole derivatives%苯并咪唑衍生物抗菌活性研究

    Institute of Scientific and Technical Information of China (English)

    赵文浩; 邓永恒; 吴华慧

    2015-01-01

    15 kinds of benzimidazole derivatives as antibacterial drug testing experiments, E. coli, and other 10 kinds of golden glucose cocci bacteria as bacteria tested by the statutory determination of the sample flat antibacterial activity. The results show that, in addition to succinic benzimidazole, other compounds have shown some antibacterial activity. Meanwhile through in vitro quantitative determination of the minimum inhibitory concentration of the sample (MIC), the experimental results show that the compounds of the bacteria have good antibacterial activity, including 2-(2-(1H-benzo [d] imidazol-2-yl) pyridin-3-yl)-1H-benzo [d] imidazole, 2,3-pyridinedicarboxylic acid, 1,2-di (1H-benzo [d] imidazol-2-yl) ethane-1,2- diol, 2-phenyl-1H-benzo [d] imidazole has a broad spectrum of antibacterial activity against Bacillus subtilis 2,2'-imidazole MIC was 0.8μg/mL, 2,3-dicarboxylic acid pyridine pneumococcal the MIC was 1.0μg/mL.%以15种苯并咪唑衍生物为抑菌实验测试药品,以大肠杆菌、金色葡萄糖球菌等10种细菌作为受试菌种,通过平板法定性测定样品的抗菌活性。结果表明,除丁二苯并咪唑外,其他的化合物都表现出一定的抑菌活性。同时通过试管法定量测定了样品的最小抑菌浓度(MIC),实验结果表明,化合物对细菌都有较好的抑菌活性,其中2-(2-(1H-benzo[d]imidazol-2-yl) pyridin-3-yl)-1H-benzo[d]imidazole、2,3-吡啶二羧酸、1,2-di(1H-benzo [d]imidazol-2-yl) ethane-1,2-diol、2-phenyl-1H-benzo[d] imidazole具有广谱的抑菌活性,2,2’-联咪唑对枯草杆菌的MIC为0.8µg/mL,2,3-吡啶二羧酸对肺炎球菌的MIC为1.0µg/mL。

  15. BODIPY-Appended 2-(2-Pyridyl)benzimidazole Platinum(II) Catecholates for Mitochondria-Targeted Photocytotoxicity.

    Science.gov (United States)

    Mitra, Koushambi; Gautam, Srishti; Kondaiah, Paturu; Chakravarty, Akhil R

    2016-09-01

    Platinum(II) complexes of the type [Pt(L)(cat)] (1 and 2), in which H2 cat is catechol and L represents two 2-(2-pyridyl)benzimidazole ligands with 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) pendants, were synthesized to achieve mitochondria-targeted photocytotoxicity. The complexes showed strong absorptions in the range λ=510-540 nm. Complex 1 exhibited intense emission at λ=525 nm in 1 % DMSO/water solution (fluorescence quantum yield of 0.06). Nanosecond transient absorption spectral features indicated an enhanced population of the triplet excited state in di-iodinated complex 2. The generation of singlet oxygen by complex 2 upon exposure to visible light, as evidenced from experiments with 1,3-diphenylisobenzofuran, is suitable for photodynamic therapy because of the remarkable photosensitizing ability. The complexes resulted in excellent photocytotoxicity in HaCaT cells (half maximal inhibitory concentration IC50 ≈3 μm, λ=400-700 nm, light dose=10 J cm(-2) ), but they remained non-toxic in the dark (IC50 >100 μm). Confocal microscopy images of 1 and Pt estimation from isolated mitochondria showed colocalization of the complexes in the mitochondria. Complex 2 displayed generation of reactive oxygen species induced by visible light, disruption of the mitochondrial membrane potential, and apoptosis. PMID:27465792

  16. Newly synthesized bis-benzimidazole compound 8 induces apoptosis, autophagy and reactive oxygen species generation in HeLa cells.

    Science.gov (United States)

    Chu, Naying; Yao, Guodong; Liu, Yuan; Cheng, Maosheng; Ikejima, Takashi

    2016-09-01

    Compound 8 (C8) is a newly synthesized bis-benzimidazole derivative and exerts significant anti-tumor activity in vitro. Previous studies demonstrated that C8 induced apoptosis and autophagy in human promyelocytic leukemia HL60 cells. However, cytotoxicity study on human peripheral blood mononuclear cells (hPBMC) showed that C8 exhibited less toxicity in normal cells. In this study, the molecular mechanism of C8 on human cervical carcinoma HeLa cells was investigated. The results showed that C8 inhibited the growth of HeLa cells and triggered both apoptotic and autophagic cell death. Subsequent experiment also indicated that reactive oxygen species (ROS) generation was induced in C8-treated HeLa cells. Since ROS scavenger decreased the ratio of apoptotic and autophagic cells, ROS generation contributed to C8-induced apoptosis and autophagy. Furthermore, inhibitors of apoptosis and autophagy also reduced ROS generation, respectively. Autophagy inhibition increased cell growth compared to C8-treated group and attenuated apoptotic cell death, indicating that C8-induced autophagy promoted apoptosis for cell death. However, the percentage of autophagic cells was enhanced when limiting apoptosis process. Taken together, C8 induced ROS-mediated apoptosis and autophagy in HeLa cells, autophagy promoted apoptosis but the former was antagonized by the latter. The data also gave us a new perspective on the anti-tumor effect of C8. PMID:27497983

  17. Molecular and Crystal Structure of 1,3,5 Tris(benzimidazol-1-ylmethyl)-2,4,6-Trimethylbenzene

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    The compound 1,3,5-tris(benzimidazol-l-ylmethyl)-2,4,6-trimethylbenzene, crystallizes in the monoclinic system, space group P2rC, with a = 17.571(4), b = 10.860(2), c = 14.126(3) A; β = 92.89(3)°, V= 2692(1)A3, De = 1.260 g/cm3, Z = 4, C33H30N6, Mr. = 510.63, μ(MoKα) = 0.077mm-1, F(000) = 1080. The structure was refined to R = 0.0592, wR = 0.1379 for 1492 (I>2σ(I)) reflections. The title molecule has cis, trans, trans-conformation about the central phenyl ring. The screw-related molecules are connected by hydrogen bonds C-H...N (x,-0.5-y, 0.5+z) and form the infinite helical chains. The polar molecular chains are antiparallelly stacked through edge-to-face C-H… π interactions.

  18. Computational Study Exploring the Interaction Mechanism of Benzimidazole Derivatives as Potent Cattle Bovine Viral Diarrhea Virus Inhibitors.

    Science.gov (United States)

    Wang, Jinghui; Yang, Yinfeng; Li, Yan; Wang, Yonghua

    2016-07-27

    Bovine viral diarrhea virus (BVDV) infections are prevailing in cattle populations on a worldwide scale. The BVDV RNA-dependent RNA polymerase (RdRp), as a promising target for new anti-BVDV drug development, has attracted increasing attention. To explore the interaction mechanism of 65 benzimidazole scaffold-based derivatives as BVDV inhibitors, presently, a computational study was performed based on a combination of 3D-QSAR, molecular docking, and molecular dynamics (MD) simulations. The resultant optimum CoMFA and CoMSIA models present proper reliabilities and strong predictive abilities (with Q(2) = 0. 64, R(2)ncv = 0.93, R(2)pred = 0.80 and Q(2) = 0. 65, R(2)ncv = 0.98, R(2)pred = 0.86, respectively). In addition, there was good concordance between these models, molecular docking, and MD results. Moreover, the MM-PBSA energy analysis reveals that the major driving force for ligand binding is the polar solvation contribution term. Hopefully, these models and the obtained findings could offer better understanding of the interaction mechanism of BVDV inhibitors as well as benefit the new discovery of more potent BVDV inhibitors. PMID:27355875

  19. Synthesis, characterization and optoelectronic properties of a new perylene diimide-benzimidazole type solar light harvesting dye

    Science.gov (United States)

    Dinçalp, Haluk; Çimen, Oguzhan; Ameri, Tayebeh; Brabec, Christoph J.; İçli, Sıddık

    2014-07-01

    A perylene diimide type small molecule (BI-PDI) has been synthesized through Suzuki coupling reaction between N,N‧-bis(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic diimide and 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid. BI-PDI small molecule has showed an absorption band between 350 and 750 nm on thin films. HOMO and LUMO energy levels of BI-PDI dye have been calculated to be about -5.92 eV and -3.82 eV, respectively. Solution-processed bulk heterojunction (BHJ) solar cells have been constructed using BI-PDI as donor and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as acceptor or poly(3-hexylthiophene) (P3HT) as donor and BI-PDI as acceptor. The external quantum efficiencies (EQE) of the devices cover the most of the visible region between 400 and 700 nm for both configurations. Photovoltaic performances of BI-PDI-based organic solar cells are limited by the aggregation tendency of PDI structure and poor hole/electron mobilities of the active layer.

  20. Self-Assembly of Hierarchical Chiral Nanostructures Based on Metal-Benzimidazole Interactions: Chiral Nanofibers, Nanotubes, and Microtubular Flowers.

    Science.gov (United States)

    Zhou, Xiaoqin; Jin, Qingxian; Zhang, Li; Shen, Zhaocun; Jiang, Long; Liu, Minghua

    2016-09-01

    Controlled hierarchical self-assembly of synthetic molecules into chiral nanoarchitectures to mimic those biological chiral structures is of great importance. Here, a low-molecular-weight organogelator containing a benzimidazole moiety conjugated with an amphiphilic l-glutamic amide has been designed and its self-assembly into various hierarchical chiral nanostructures is investigated. Upon gel formation in organic solvents, 1D chiral nanostructure such as nanofiber and nanotube are obtained depending on the solvents. In the presence of transition and rare earth metal ions, hierarchical chiral nanostructures are formed. Specifically, the addition of TbCl3 , EuCl3 , and AgNO3 leads to nanofiber structures, while the addition of Cu(NO3 )2 , Tb(NO3 )3 , or Eu(NO3 )3 provides the microflower structures and microtubular flower structures, respectively. While Eu(III) and Tb(III)-containing microtubular flowers keep the chirality, the Cu(II)-coordinated microflowers lose chirality. More interestingly, the nanofibers formed by the gelator coordinated with Eu(III) or Tb(III) ions show not only the supramolecular chirality but also the circularly polarized luminescence. PMID:27248367

  1. Metal coordination polymers of 2,3-bis(benzimidazol-1-ylmethyl)quinoxaline: Syntheses, crystal structures and luminescent properties

    Science.gov (United States)

    Du, Jian-Long; Wei, Zi-Zhang; Hu, Tong-Liang

    2011-06-01

    Two new metal-organic frameworks, {[Cu LI]·CHCl 3} ∞( 1) and {[Hg L(Br) 2] 4·2CH 2Cl 2} ∞ ( 2) have been prepared by reacting CuI and HgBr 2 with the new flexible ligand L [ L = 2,3-Bis(benzimidazol-1-ylmethyl)quinoxaline]. Both complexes have been characterized by elemental analysis, IR, TGA, XRPD, and single crystal X-ray diffraction determination. In 1, the Cu(I) ion takes tetrahedral coordination geometry, and the flexible ligands bridge dinuclear units (Cu 2I 2) to form a one dimensional (1D) double chain structure. While in 2, the Hg(II) coordinates to two bromine ions and two nitrogen donors of L to form a 1D coordination polymer. The structure differences of the two complexes mainly depend on the geometry of the metal ions and the influence of anions. The coordination features of the ligand have also been primarily investigated by density functional theory (DFT) calculations. In addition, the fluorescent properties of the complexes and free ligand L have been investigated in the solid state at room temperature.

  2. Water and phosphoric acid uptake of poly [2,5-benzimidazole] (ABPBI) membranes prepared by low and high temperature casting

    Energy Technology Data Exchange (ETDEWEB)

    Diaz, Liliana A.; Corti, Horacio R. [Departamento de Fisica de Materia Condensada, Centro Atomico Constituyentes, Comision Nacional de Energia Atomica (CNEA), B1650KNA San Martin, Buenos Aires (Argentina); Abuin, Graciela C. [Instituto Nacional de Tecnologia Industrial (INTI), B1650KNA San Martin, Buenos Aires (Argentina)

    2009-03-01

    Phosphoric acid-doped membranes based in poly[2,5-benzimidazole] (ABPBI) were obtained by a new low temperature casting procedure and by the classical high temperature casting from methanesulfonic acid. These membranes, which can be suitable for application in direct methanol proton exchange membrane (PEM) fuel cells, were studied in relation with their phosphoric acid doping level by measuring the free and bonded acid. The water isotherms were also determined for the low and high temperature casted ABPBI membranes. Both, acid and water sorption properties, were compared with those determined in poly [2-2'-(m-fenylene)-5-5' bibenzimidazole] (PBI) membranes. The water sorption of the ABPBI membranes over the range of all water activity is described by the modified BET equation, commonly known as Guggenheim-Anderson-de Boer (GAB) and a two-parameters empirical isotherm. The acid uptake behaviour of the membranes prepared by low and high temperature casting are related with differences in their supramolecular structure. (author)

  3. Naked-eye detection and thermochromic properties of Cu(II)-3,3'-thiodipropionate complexes with benzimidazole.

    Science.gov (United States)

    Arıcı, Mürsel; Yeşilel, Okan Zafer; Taş, Murat

    2015-01-28

    Two new coordination complexes, namely, [Cu(tdp)(H2O)(bim)3]·4H2O (1) and {[Cu(μ2-tdp)(bim)2]·4H2O}n (2) (tdp = 3,3'-thiodipropionate, bim = benzimidazole), having naked-eye sensor properties and thermochromic behaviors, were synthesized and structurally characterized using elemental analysis, IR and UV spectra, and single-crystal X-ray diffraction, powder X-ray diffraction (PXRD) and thermal analyses (TG, DTA and DTG) techniques. Complex 1 changed color from blue to dark and light green in methanol and DMF solvents, respectively, while complex 2 changed color from light blue to light green only in DMF solvent. Moreover, complex 1 can be used to detect as little as 10 percent methanol in ethanol by the naked eye. The thermochromic properties of the complexes showed that complexes 1 and 2 changed color from blue and light blue to light and dark green at 65 °C, respectively. PMID:25436449

  4. Structure-based design and development of (benz)imidazole pyridones as JAK1-selective kinase inhibitors.

    Science.gov (United States)

    Simov, Vladimir; Deshmukh, Sujal V; Dinsmore, Christopher J; Elwood, Fiona; Fernandez, Rafael B; Garcia, Yudith; Gibeau, Craig; Gunaydin, Hakan; Jung, Joon; Katz, Jason D; Kraybill, Brian; Lapointe, Blair; Patel, Sangita B; Siu, Tony; Su, Hua; Young, Jonathan R

    2016-04-01

    The mammalian Janus Kinases (JAK1, JAK2, JAK3 and TYK2) are intracellular, non-receptor tyrosine kinases whose activities have been associated in the literature and the clinic with a variety of hyperproliferative diseases and immunological disorders. At the onset of the program, it was hypothesized that a JAK1 selective compound over JAK2 could lead to an improved therapeutic index relative to marketed non-selective JAK inhibitors by avoiding the clinical AEs, such as anemia, presumably associated with JAK2 inhibition. During the course of the JAK1 program, a number of diverse chemical scaffolds were identified from both uHTS campaigns and de novo scaffold design. As part of this effort, a (benz)imidazole scaffold evolved via a scaffold-hopping exercise from a mature chemical series. Concurrent crystallography-driven exploration of the ribose pocket and the solvent front led to analogs with optimized kinome and JAK1 selectivities over the JAK2 isoform by targeting several residues unique to JAK1, such as Arg-879 and Glu-966. PMID:26927423

  5. Design, synthesis and biological evaluation of berberine-benzimidazole hybrids as new type of potentially DNA-targeting antimicrobial agents.

    Science.gov (United States)

    Jeyakkumar, Ponmani; Zhang, Ling; Avula, Srinivasa Rao; Zhou, Cheng-He

    2016-10-21

    A series of novel berberine-benzimidazole derivatives were conveniently and efficiently synthesized and characterized by NMR, IR, MS and HRMS spectra. Most of the prepared compounds showed effective antimicrobial activities in contrast with clinical norfloxacin, chloromycin and fluconazole. Especially, compound 5d exhibited good anti-MRSA, anti-Escherichia coli, and anti-Salmonella typhi activity with low MIC values of 2-8 μg/mL, which were comparable or even superior to reference drugs. The preliminarily interactive investigation revealed that the most active compound 5d could effectively intercalate into DNA to form 5d-DNA complex and cleavage DNA by agarose gel electrophoresis experiments. It was also found that compound 5d was able to efficiently permeabilize the membranes of both Gram-positive (MRSA) and Gram-negative (E. coli DH52) bacteria. Experiments and molecular docking both showed that human serum albumin (HSA) could effectively transport compound 5d and hydrophobic interactions and hydrogen bonds play important roles in the association of compound 5d with HSA. PMID:27371924

  6. Proton conducting membranes based on Poly(2,5-benzimidazole) (ABPBI)-Poly(vinylphosphonic acid) blends for fuel cells

    Energy Technology Data Exchange (ETDEWEB)

    Acar, Oktay; Sen, Unal; Ata, Ali [Gebze Institute of Technology, Materials Science and Engineering, 41400 Gebze, Kocaeli (Turkey); Bozkurt, Ayhan [Fatih University, Department of Chemistry, 34500 Buyukcekmece, Istanbul (Turkey)

    2009-03-15

    Polymer electrolyte membranes (PEM) were fabricated by blending of Poly(2,5-benzimidazole) (ABPBI) and Poly(vinylphosphonic acid) (PVPA) at several stoichiometric ratios with respect to monomer repeating units. The characterization of the membranes were carried out by using Fourier-transform infrared spectroscopy (FT-IR) for inter-polymer interactions, scanning electron microscope (SEM) for surface morphology as well as homogeneity and thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) for thermal properties. Water uptake measurements were made to investigate the swelling character the blends that was changed with PVPA composition. The spectroscopic measurements and water uptake studies suggested the complexation between ABPBI and PVPA that inhibited dopant exclusion up on swelling in excess water. Proton conductivities of the hydrated and anhydrous samples were measured using impedance spectroscopy. Although the proton conductivity of the blends was lower in the anhydrous state such as 1.8 x 10{sup -6} S/cm at 150 C for ABPBI:PVPA with (1:2), it increased to 0.004 S/cm for ABPBI:PVPA (1:4) at 20 C (RH = 50%). (author)

  7. Effect of Mercapto and Methyl Groups on the Efficiency of Imidazole and Benzimidazole-based Inhibitors of Iron Corrosion.

    Science.gov (United States)

    Milošev, Ingrid; Kovačević, Nataša; Kokalj, Anton

    2016-01-01

    We report on the combined experimental and computational study of imidazole- and benzimidazole-based corrosion inhibitors containing methyl and/or mercapto groups. Electrochemical measurements and long-term immersion tests were performed on iron in NaCl solution, whilst computational study explicitly addresses the molecular level details of the bonding on iron surface by means of density functional theory calculations (DFT). Experimental data were the basis for the determination of inhibition efficiency and mechanism. Methyl group combined with mercapto group has a beneficial effect on corrosion inhibition at all inhibitor concentrations. The beneficial effect of mercapto group combined with benzene group is not so pronounced as when combined with methyl group. The latter is in stark contrast with the behaviour found previously on copper, where the effect of methyl group was detrimental and that of mercapto and benzene beneficial. Explicit DFT calculations reveal that methyl-group has a small effect on the inhibitor-surface interaction. In contrast, the presence of mercapto group involves the strong S-surface bonding and consequently the adsorption of inhibitors with mercapto group is found to be more exothermic.

  8. 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

  9. Synthesis, characterization and optoelectronic properties of a new perylene diimide-benzimidazole type solar light harvesting dye.

    Science.gov (United States)

    Dinçalp, Haluk; Çimen, Oguzhan; Ameri, Tayebeh; Brabec, Christoph J; İçli, Sıddık

    2014-07-15

    A perylene diimide type small molecule (BI-PDI) has been synthesized through Suzuki coupling reaction between N,N'-bis(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic diimide and 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid. BI-PDI small molecule has showed an absorption band between 350 and 750 nm on thin films. HOMO and LUMO energy levels of BI-PDI dye have been calculated to be about -5.92 eV and -3.82 eV, respectively. Solution-processed bulk heterojunction (BHJ) solar cells have been constructed using BI-PDI as donor and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as acceptor or poly(3-hexylthiophene) (P3HT) as donor and BI-PDI as acceptor. The external quantum efficiencies (EQE) of the devices cover the most of the visible region between 400 and 700 nm for both configurations. Photovoltaic performances of BI-PDI-based organic solar cells are limited by the aggregation tendency of PDI structure and poor hole/electron mobilities of the active layer. PMID:24667425

  10. 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.

  11. 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.

  12. Influence of Temperatures on the Tautomerism of the N-(1H- Imidazoline-2-yl)-lH-benzimidazol-2-amine and Investigation of Its Electrochemical Behaviour%Influence of Temperatures on the Tautomerism of the N-(1H- Imidazoline-2-yl)-lH-benzimidazol-2-amine and Investigation of Its Electrochemical Behaviour

    Institute of Scientific and Technical Information of China (English)

    Servi, Suleyman; Genc, Murat; Saydam, Sinan

    2012-01-01

    Synthesis of N-(1H-imidazoline-2-yl)-lH-benzimidazol-2-amine was carried out under microwave irradiation (MWI) conditions. Dynamic 1H NMR investigation of N-(lH-imidazoline-2-yl)-lH-benzimidazol-2-amine compound was reported at temperature range of 223--333 K in DMF-d7. Some physical parameters, such as coalescence temperature (Tc), the free energy of activation (△G*) and rate constant (k) values were calculated from its IH NMR spectra at various temperatures. Electrochemical feature of this compound was investigated by cyclic (CV) and square wave voltammetry (SWV).

  13. Di-μ-thio­cyanato-κ2 N:S;κ2 S:N-bis­[bis­(2-methyl-1H-benzimidazole-κN 3)(thio­cyanato-κN)cadmium(II)

    OpenAIRE

    A. Shaker, Shayma; Khaledi, Hamid; Mohd Ali, Hapipah

    2010-01-01

    The title compound, [Cd2(NCS)4(C8H8N2)4], is a centrosymmetric dinuclear cadmium(II) complex in which each two metal ions are linked by a pair of thio­cyanate N:S-bridges. Two 2-methyl­benzimidazole N-atom donors and one terminal thio­cyanate N atom complete a highly distorted square-pyramidal geometry around the Cd atom. In the crystal structure, two N—H⋯S hydrogen-bonding inter­actions occur, resulting in a three-dimensional polymeric structure. The apical 2-methyl­benzimidazole ring and it...

  14. 用分子动力学模拟苯并咪唑类化合物在铁表面的吸附%Molecular Dynamics Study of the Adsorption of Benzimidazole and its Derivatives on Fe surface

    Institute of Scientific and Technical Information of China (English)

    许立宁; 王兴; 常炜; 路民旭

    2012-01-01

    利用分子动力学(MD)方法分别研究了5种苯并咪唑类化合物:苯并咪唑(BIM),2-丙基苯并咪唑(2-PBIM),2-戊基苯并咪唑(2-ABIM),2-己基苯并咪唑(2-HBIM)以及2-对氯苄基苯并咪唑(2-C1-BBIM)在铁表面的吸附行为。同时利用腐蚀失重法、极化曲线等方法测试缓蚀效率。结果表明,计算得出的5种缓蚀剂吸附能大小排序为:BIM%2-PBIM%2-ABIM%2-HBIM%2-C1-BBIM,与失重法得出的缓蚀效率排序-致。径向分布函数分析表明,5种缓蚀剂都能与铁表面形成化学吸附。%The adsorption behavior of five corrosion inhibitors including benzimidazole, 2-propyl benzimidazole, 2-amyl benzimidazole, 2-hexyl benzimidazole and 2-chloro-benzyl benzimidazole on Fe surface was studied by using molecular dynamics(MD) method. The inhibition efficiency of the five corrosion inhibitors was measured by weight loss method and polarization curve testing. The results show that the order of the adsorption energy of five corrosion inhibitors calculated by the molecular dynamics method is benzimidazole 〈 2-propyl benzimidazole % 2-amyl benzimidazole〈2-hexyl benzimidazole〈2-chloro-benzyl benzimidazole, which is in good accordance with the inhibition efficiency obtained by weight loss method. Radial distribution function of the five adsorbing systems was analyzed and it is found that the five corrosion inhibitors can all establish chemical adsorption with Fe surface.

  15. Polymer/organosilica nanocomposites based on polyimide with benzimidazole linkages and reactive organoclay containing isoleucine amino acid: Synthesis, characterization and morphology properties

    Energy Technology Data Exchange (ETDEWEB)

    Mallakpour, Shadpour, E-mail: mallak@cc.iut.ac.ir [Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, Islamic Republic of Iran (Iran, Islamic Republic of); Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, Isfahan 84156-83111, Islamic Republic of Iran (Iran, Islamic Republic of); Dinari, Mohammad [Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, Islamic Republic of Iran (Iran, Islamic Republic of)

    2012-09-15

    Highlights: ► A reactive organoclay was formed using L-isoleucine amino acid as a swelling agent. ► Polyimide was synthesized from benzimidazole diamine and pyromellitic dianhydride. ► Imide and benzimidazole groups assured the thermal stability of the nanocomposites. ► Nanocomposite films were prepared by an in situ polymerization reaction. ► The TEM micrographs of nanocomposites revealed well-exfoliated structures. -- Abstract: Polyimide–silica nanocomposites are attractive hybrid architectures that possess excellent mechanical, thermal and chemical properties. But, the dispersion of inorganic domains in the polymer matrix and the compatibility between the organic and inorganic phases are critical factors in these hybrid systems. In this investigation, a reactive organoclay was prepared via ion exchange reaction between protonated form of difunctional L-isoleucine amino acid as a swelling agent and Cloisite Na{sup +} montmorillonite. Amine functional groups of this swelling agent formed an ionic bond with the negatively charged silicates, whereas the remaining acid functional groups were available for further interaction with polymer chains. Then organo-soluble polyimide (PI) have been successfully synthesized from the reaction of 2-(3,5-diaminophenyl)-benzimidazole and pyromellitic dianhydride in N,N-dimethylacetamide. Finally, PI/organoclay nanocomposite films enclosing 1%, 3%, 5%, 7% and 10% of synthesized organoclay were successfully prepared by an in situ polymerization reaction through thermal imidization. The synthesized hybrid materials were subsequently characterized by Fourier transform infrared spectroscopy, X-ray diffraction, electron microscopy, and thermogravimetric analysis techniques. The PI/organoclay nanocomposite films have good optical transparencies and the mechanical properties were substantially improved by the incorporation of the reactive organoclay.

  16. Critical tests in equids with fenbendazole alone or combined with piperazine: particular reference to activity on benzimidazole-resistant small strongyles.

    Science.gov (United States)

    Lyons, E T; Tolliver, S C; Drudge, J H

    1983-02-01

    Seven critical tests in equids were conducted with single doses of fenbendazole (5 mg kg-1) alone (Panacur--American Hoechst, Somerville, NJ); (2 tests with paste and 1 with suspension formulation) or in combination with piperazine (American Hoechst); (40 mg base kg-1); (4 tests with paste formulation). The main purpose of the tests was evaluation of activity against benzimidazole-resistant small strongyles (Cyathostomum catinatum, Cyathostomum coronatum, Cylicocyclus nassatus, Cylicostephanus goldi, and Cylicostephanus longibursatus). Natural infections of 2 populations of benzimidazole-resistant small strongyles were evaluated; 1 was population B in 2 horses and the other was population S in 5 ponies. Removal of the 5 species of population B was 49-91% in the animal treated with fenbendazole paste alone and 100% (4 of these species present) in the animal treated with the combination. For population S, 2 of the 5 resistant species were present in small numbers in 1 animal treated with fenbendazole paste alone and all were removed; the 1 animal receiving fenbendazole suspension alone had removals of 0-70% for the 5 benzimidazole-resistant species. Also for population S, the 5 resistant species were present in 2 animals treated with the paste combination and removal was 98-100% and of 4 of the 5 resistant species in 1 animal, removal was 76-99%. Removal of large strongyles (Strongylus vulgaris and Strongylus edentatus) was 92-100% for fenbendazole paste alone or in combination with piperazine in the 5 infected animals. For Oxyuris equi, present in 1 animal treated with the combination, there was 91% removal of immature and 100% removal of mature specimens. There probHably was no activity by fenbendazole alone or the combination against bots, tapeworms, and parenteral stages of S. vulgaris and S. edentatus. The combination may have had some activity against immature Habronema spp. and mature abronema muscae.

  17. Hepatic microsomal metabolism of the anthelmintic benzimidazole fenbendazole: enhanced inhibition of cytochrome P450 reactions by oxidized metabolites of the drug.

    Science.gov (United States)

    Murray, M; Hudson, A M; Yassa, V

    1992-01-01

    Potentiation of the anthelmintic action of benzimidazole carbamates, such as fenbendazole [methyl 5(6)-(phenylthio)-1H-benzimidazol-2-ylcarbamate], has been noted during concurrent administration of benzimidazoles that possess no intrinsic anthelmintic activity. This study investigated the possibility that inhibition of P450 enzymes by fenbendazole and its metabolites could play a role in the potentiation phenomenon. Fenbendazole underwent P450-mediated oxidation in microsomes from untreated rat liver to the sulfoxide and (4'-hydroxyphenyl)thio metabolites [2.92 and 2.87 nmol/(mg of protein.h)]. Pretreatment of rats with phenobarbital or dexamethasone enhanced sulfoxidation by 1.9- and 2.9-fold, respectively. 4'-Hydroxylation was increased slightly (by 28%) by phenobarbital and decreased slightly (by 41%) by dexamethasone. Induction also promoted further metabolism of the sulfoxide to fenbendazole sulfone. Immunoinhibition and chemical inhibition studies suggested that P450 3A proteins and the flavin-containing monooxygenase are involved in sulfoxide and sulfone formation whereas 4'-hydroxylation involved the P450s 2C11, 2C6, and 2B1, depending on the type of induction. In untreated rat liver, the sulfoxide and (4'-hydroxyphenyl)thio metabolites of fenbendazole were relatively potent inhibitors of P450-mediated androstenedione 16 alpha-, 16 beta-, and 6 beta-hydroxylation (IC50 values of 42, 36, and 74 microM, respectively); 7 alpha-hydroxylase activity was uninhibited. In contrast, fenbendazole and its sulfone metabolite were not inhibitors of these reactions. Mixed-function oxidase activities in phenobarbital-induced rat hepatic microsomes were refractory to inhibition by most compounds, but P450 1A1 mediated activities in microsomes from beta-naphthoflavone-induced rat liver were quite susceptible to inhibition by fenbendazole sulfoxide. Studies with two analogous sulfoxides yielded similar findings.(ABSTRACT TRUNCATED AT 250 WORDS)

  18. Effect of alcohols on separation behavior of rare earth elements using benzimidazole-type anion-exchange resin in nitric acid solutions

    International Nuclear Information System (INIS)

    The mutual separation of rare earth elements based on the ion exchange chromatography has been studied. The effect of alcohols on separation behavior of rare earth elements using the benzimidazole-type anion-exchange resin embedded in high-porous silica beads was investigated in nitric acid/alcohol mixed solvent systems. It was confirmed that the mutual separation of rare earth elements is possible by using our proposed methods. It was found that the distribution coefficients of rare earth elements depend on the corresponding alcoholic relative permittivity and on the steric hindrance due to the hydrophobic interaction among each alcoholic molecule. (author)

  19. Bis(acetylacetonato-κ2O,O′(2-amino-1-methyl-1H-benzimidazole-κN3oxidovanadium(IV

    Directory of Open Access Journals (Sweden)

    Zukhra Ch. Kadirova

    2009-07-01

    Full Text Available The title mixed-ligand oxidovanadium(IV compound, [VO(C5H7O22(C8H9N3], contains a VIV atom in a distorted octahedral coordination, which is typical for such complexes. The vanadyl group and the N-heterocyclic ligand are cis to each other. The coordination bond is located at the endocyclic N atom of the benzimidazole ligand. Intramolecular hydrogen bonds between the exo-NH2 group H atoms and acetylacetonate O atoms stabilize the crystal structure.

  20. Iodido[5-methyl-1H-benzimidazole-2(3H-thione-κS]bis(triphenylphosphane-κPcopper(I methanol monosolvate

    Directory of Open Access Journals (Sweden)

    Yu-Han Jiang

    2012-10-01

    Full Text Available In the title compound, [CuI(C8H8N2S(C18H15P2]·CH3OH, the coordination environment around the CuI atom is distorted tetrahedral, defined by two P atoms of two triphenylphosphane ligands, one S atom of a 5-methyl-1H-benzimidazole-2(3H-thione ligand and one I atom. The complex molecules and the methanol solvent molecules are connected via N—H...O and O—H...I hydrogen bonds, forming a chain along [010]. An intramolecular N—H...I hydrogen bond is also observed.

  1. Tetra-μ3-iodido-tetrakis{[ethyl 2-(1H-benzimidazol-1-ylacetate-κN3]copper(I}

    Directory of Open Access Journals (Sweden)

    Lili Yang

    2012-06-01

    Full Text Available The complex molecule of the tetranuclear cubane-type title compound, [Cu4I4(C11H12N2O24], has crystallographically imposed fourfold inversion symmetry. The CuI ions are coordinated in a distorted tetrahedral geometry by an N atom of a benzimidazole ring system and three μ3-iodide ions, forming a Cu4I4 core. In the crystal, complex molecules are connected into a three-dimensional network by C—H...O hydrogen bonds involving H and O atoms of adjacent ethoxycarbonyl groups.

  2. 1-(2,3,4,5,6-Penta­methyl­benz­yl)-2-(pyridin-2-yl)-1H-benzimidazole

    OpenAIRE

    Anĝay, Fırat; Çelik, Ömer; Barlık, Orhan; Ulusoy, Mahmut

    2014-01-01

    In the title compound, C24H25N3, the benzimidazole ring system is essentially planar, with an r.m.s. deviation of 0.017 Å, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the pyridine and benzene rings, respectively. An intra­molecular C—H⋯N hydrogen bond is observed. In the crystal, mol­ecules are stacked along the a axis by weak C—H⋯π inter­actions.

  3. Bis[2,6-bis(1-methyl-1H-benzimidazol-2-yl-κN3pyridine-κN]zinc dipicrate methanol disolvate

    Directory of Open Access Journals (Sweden)

    Xuyang Fan

    2012-08-01

    Full Text Available In the title compound, [Zn(C21H17N52](C6H2N3O72·2CH3OH, the ZnII atom is coordinated by six N atoms from two tridentate 2,6-bis(1-methyl-1H-benzimidazol-2-ylpyridine ligands in a distorted octahedral environment. In the crystal, the picrate anions and methanol solvent molecules are connected by O—H...O hydrogen bonds. Weak intermolecular C—H...O hydrogen bonds are also observed.

  4. Anion-controlled assembly of metal 3,5-bis(benzimidazol-1-ylmethyl) benzoate complexes: Synthesis, characterization and property

    Energy Technology Data Exchange (ETDEWEB)

    Kuai, Hai-Wei [Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, Nanjing 210093 (China); Faculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003 (China); Lv, Gao-Chao; Hou, Chao [Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, Nanjing 210093 (China); Sun, Wei-Yin, E-mail: sunwy@nju.edu.cn [Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, Nanjing 210093 (China)

    2015-03-15

    Hydrothermal reactions of 3,5-bis(benzimidazol-1-ylmethyl)benzoic acid (HL) with Cd(II), Cu(II) and Zn(II) salts provide eight new metal complexes which were characterized by single crystal and powder X-ray diffraction, IR, elemental and thermogravimetric analyses. Two cadmium frameworks [Cd(L){sub 2}]·2H{sub 2}O (1) and [Cd(L)Cl] (2) have 3D structures with (4{sup 2}.6{sup 5}.8{sup 3})(4{sup 2}.6) and rtl (4.6{sup 2}){sub 2}(4{sup 2}.6{sup 10}.8{sup 3}) topologies, respectively. Structural diversity of four copper complexes [Cu{sub 3}(L){sub 2}]·NO{sub 3}·0.5H{sub 2}O (3), [Cu{sub 2}(HL){sub 2}(SO{sub 4})]·3.5H{sub 2}O (4), [Cu(L)(bdc){sub 0.5}]·1.5H{sub 2}O (5) and [Cu{sub 2}(L)(HL)(Hbdc)] (6) (H{sub 2}bdc=1,4-benzenedicarboxylic acid) is achieved through the alteration of copper salts and addition of auxiliary ligand. As a result, 3 has a 1D ladder structure, 4 is a discrete dinuclear complex, 5 displays a (3,4)-connected 2-nodal 3-fold interpenetrating framework with (4{sup 2}.6.10{sup 2}.12)(4{sup 2}.6) topology, 6 exhibits a 4-connected uninodal 2D sql (4{sup 4}.6{sup 2}) network. Within the zinc series, ZnCl{sub 2} and ZnSO{sub 4} were used for the syntheses of [Zn(L)Cl] (7) and [Zn(L)(SO{sub 4}){sub 0.5}]·2H{sub 2}O (8), respectively. 7 shows a 3-connected uninodal 2D hcb network with (6{sup 3}) topology and 8 is a (3,6)-connected 2-nodal 3D framework with (4{sup 2}.6){sub 2}(4{sup 4}.6{sup 2}.8{sup 8}.10) topology. The luminescent properties of the Cd(II) and Zn(II) complexes were investigated. - Graphical abstract: Eight new complexes have been successfully synthesized from the hydrothermal reactions of Cd(II), Cu(II) and Zn(II) salts with 3,5-bis(benzimidazol-1-ylmethyl)benzoic acid. The complexes exhibited anion-controlled structural diversity. - Highlights: • Metal complexes have diverse structures of 1D chains, 2D networks and 3D frameworks. • Anion-controlled assembly of the complexes is reported. • The luminescent properties of the Cd

  5. Identification of benzimidazole diamides as selective inhibitors of the nucleotide-binding oligomerization domain 2 (NOD2 signaling pathway.

    Directory of Open Access Journals (Sweden)

    David J Rickard

    Full Text Available NOD2 is an intracellular pattern recognition receptor that assembles with receptor-interacting protein (RIP-2 kinase in response to the presence of bacterial muramyl dipeptide (MDP in the host cell cytoplasm, thereby inducing signals leading to the production of pro-inflammatory cytokines. The dysregulation of NOD2 signaling has been associated with various inflammatory disorders suggesting that small-molecule inhibitors of this signaling complex may have therapeutic utility. To identify inhibitors of the NOD2 signaling pathway, we utilized a cell-based screening approach and identified a benzimidazole diamide compound designated GSK669 that selectively inhibited an MDP-stimulated, NOD2-mediated IL-8 response without directly inhibiting RIP2 kinase activity. Moreover, GSK669 failed to inhibit cytokine production in response to the activation of Toll-like receptor (TLR-2, tumor necrosis factor receptor (TNFR-1 and closely related NOD1, all of which share common downstream components with the NOD2 signaling pathway. While the inhibitors blocked MDP-induced NOD2 responses, they failed to block signaling induced by NOD2 over-expression or single stranded RNA, suggesting specificity for the MDP-induced signaling complex and activator-dependent differences in NOD2 signaling. Investigation of structure-activity relationship allowed the identification of more potent analogs that maintained NOD2 selectivity. The largest boost in activity was achieved by N-methylation of the C2-ethyl amide group. These findings demonstrate that the NOD2 signaling pathway is amenable to modulation by small molecules that do not target RIP2 kinase activity. The compounds we identified should prove useful tools to investigate the importance of NOD2 in various inflammatory processes and may have potential clinical utility.

  6. Identification of Benzimidazole Diamides as Selective Inhibitors of the Nucleotide-Binding Oligomerization Domain 2 (NOD2) Signaling Pathway

    Science.gov (United States)

    Rickard, David J.; Sehon, Clark A.; Kasparcova, Viera; Kallal, Lorena A.; Zeng, Xin; Montoute, Monica N.; Chordia, Tushar; Poore, Derek D.; Li, Hu; Wu, Zining; Eidam, Patrick M.; Haile, Pamela A.; Yu, Jong; Emery, John G.; Marquis, Robert W.; Gough, Peter J.; Bertin, John

    2013-01-01

    NOD2 is an intracellular pattern recognition receptor that assembles with receptor-interacting protein (RIP)-2 kinase in response to the presence of bacterial muramyl dipeptide (MDP) in the host cell cytoplasm, thereby inducing signals leading to the production of pro-inflammatory cytokines. The dysregulation of NOD2 signaling has been associated with various inflammatory disorders suggesting that small-molecule inhibitors of this signaling complex may have therapeutic utility. To identify inhibitors of the NOD2 signaling pathway, we utilized a cell-based screening approach and identified a benzimidazole diamide compound designated GSK669 that selectively inhibited an MDP-stimulated, NOD2-mediated IL-8 response without directly inhibiting RIP2 kinase activity. Moreover, GSK669 failed to inhibit cytokine production in response to the activation of Toll-like receptor (TLR)-2, tumor necrosis factor receptor (TNFR)-1 and closely related NOD1, all of which share common downstream components with the NOD2 signaling pathway. While the inhibitors blocked MDP-induced NOD2 responses, they failed to block signaling induced by NOD2 over-expression or single stranded RNA, suggesting specificity for the MDP-induced signaling complex and activator-dependent differences in NOD2 signaling. Investigation of structure-activity relationship allowed the identification of more potent analogs that maintained NOD2 selectivity. The largest boost in activity was achieved by N-methylation of the C2-ethyl amide group. These findings demonstrate that the NOD2 signaling pathway is amenable to modulation by small molecules that do not target RIP2 kinase activity. The compounds we identified should prove useful tools to investigate the importance of NOD2 in various inflammatory processes and may have potential clinical utility. PMID:23936340

  7. Synthesis of 2-Aryl-l-arylmethyl-lH-1,3-benzimidazole Derivatives Using Silica-bonded PropyI-S-sulfonic Acid as Recyclable Solid Acid Catalyst

    Institute of Scientific and Technical Information of China (English)

    Ghaem Ahmadi-Ana,Sayed Mohammad; Baghernejad, Mojtaba"; Niknam, Khodabakhsh

    2012-01-01

    A highly selective synthesis of 2-aryl-l-arylmethyl-lH-1,3-benzimidazoles from the reaction of o-phenylene- diamine and aromatic aldehydes in the presence of silica-bonded propyl-S-sulfonic acid (SBSSA) at 80℃ in water in good to excellent yields was developed.

  8. Benzimidazole ligands in the corrosion inhibition for carbon steel in acid medium: DFT study of its interaction on Fe30 surface

    Science.gov (United States)

    Garcia-Ochoa, E.; Guzmán-Jiménez, S. J.; Hernández, J. Guadalupe; Pandiyan, Thangarasu; Vásquez-Pérez, José M.; Cruz-Borbolla, Julián

    2016-09-01

    The corrosion inhibition of N,N‧-bis(benzimidazole-2-yl-methyl)amine (L1) and N, N‧-bis(benzimidazole-2-yl-methyl)hydroxyethylamine (L2) was analyzed by electrochemical and theoretical methods. The data show that ligands form an adsorption layer over an iron surface, obeying the Langmuir isotherm (Δ Gads° of -32.96 kJ mol-1); the value are higher than -20 kJ mol-1 but less than -40 kJ mol-1, belonging to a conversion stage of physical adsorption to chemical adsorption or a comprehensive adsorption. This is consistent with fractal dimension of the electrode surface, estimated by an impedance depression angle of a semicircle that the surface is homogeneously covered by the formation of an inhibitor film. Furthermore, the electronic parameters of the ligands were analyzed by DFT, showing that L1 and L2 possesses corrosion inhibition properties that give up its p orbital electron density through its HOMO orbital to the metal LUMO to form an adsorption layer, and this has been proved theoretically by the interaction of ligands with Fe30. In addition, we have collected corrosion inhibition data for around 70 organic compounds reported in the literature, and the inhibition data plotted against different inhibitors, showing that amine ligands are good corrosion inhibitors.

  9. Photophysical Behavior and Computational Investigation of Novel 1,4-Bis(2-(2-Phenylpyrimido[1,2-a]Benzimidazol-4-Yl)Phenoxy)Butan (BPPB) Macromolecule.

    Science.gov (United States)

    Saleh, Tamer S; Hussein, Mahmoud A; Osman, Osman I; Alamry, Khalid A; Mekky, Ahmed E M; Asiri, Abdullah M; El-Daly, Samy A

    2016-09-01

    A new macromolecule pyrimido[l,2-a]benzimidazole derivative named 1,4-bis(2-(2-phenylpyrimido[1,2-a]benzimidazol-4-yl)phenoxy)butan (BPPB) has been synthesized in accepted yield using microwave assistance. The new compound BPPB has been formed by the interaction of 3,3'-((butane-1,4-diylbis(oxy))bis(2,1-phenylene))bis(1-phenylprop-2-en-1-one) (3) with 2- aminobenzimidazole (4) in the presence of potassium hydroxide as a basic catalyst in dimethylformamide (DMF) under microwave radiation for 20 min. The chemical structure of this novel compound was elucidated by elemental and spectral techniques including: FT-IR, (1)H-NMR, (13)C-NMR and mass spectra. The electronic absorption and emission spectra of BPPB were measured in different solvents. BPPB displayed a solvatochromic effect of the emission spectrum that is reflected by red shifts of its fluorescence emission maxima on increasing the solvent polarity, indicating a change of electronic charge distribution upon excitation. BPPB crystalline solids gave excimer-like emission at 535 nm with a bandwidth of ca. 60 nm. Ground and excited states electronic geometry optimizations using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively, complemented these spectral findings. The intramolecular charge transfer was investigated by natural bond orbital (NBO) technique. PMID:27476069

  10. Proton conducting sulfonated poly (imide-benzimidazole) with tunable density of covalent/ionic cross-linking for fuel cell membranes

    Science.gov (United States)

    Yue, Zhouying; Cai, Yang-Ben; Xu, Shiai

    2015-07-01

    Ionic cross-linked sulfonated polyimides containing bis-benzimidazole rings have been prepared from 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTDA), 6,6‧-bis[2-(4-aminophenyl)benzimidazole] (BAPBI) and 3,3‧-bis(4-sulfophenoxy)- benzidine (BSPOB). A new cross-linker, 4,4‧-bibromomethenyl diphenyl ether, is used to induce covalent cross-linking between halogen and imidazole groups in SPIBI chains via a facile thermally activated reaction. The resulted covalent and ionic cross-linked membranes show an improved resistance to hydrolytic attack in deionized water at 80 °C (more than two months) and free radical attack in Fenton's solution (more than 690 min) as compared to non-cross-linked SPIBIs (less than two days and 270 min, respectively). Cross-linking also results in a reduction in proton conductivity due to the blockage of a hydrophilic channel. However, all the prepared CBr-ySPIBI-x membranes show a proton conductivity higher than 10-2 S cm-1 under hydrous condition. This could be attributed to the fact that more cross-linking sites are contained in each repeating unit, which ensures enough cross-linking degree at high sulfonation level. All these results suggest that CBr-ySPIBI-x membranes have a great potential for applications in the proton exchange membrane fuel cells.

  11. A new AgI complex based on 1-[(1H-benzimidazol-1-ylmethyl]-1H-1,2,4-triazole

    Directory of Open Access Journals (Sweden)

    Yan-zhi Wang

    2011-12-01

    Full Text Available In the title complex, bis{μ-1-[(1H-benzimidazol-1-ylmethyl]-1H-1,2,4-triazole}disilver(I dinitrate, [Ag2(C10H9N52](NO32, the AgI ion is nearly linearly coordinated [N—Ag—N angle is 155.72 (14°] by two 1-[(1H-benzimidazole-1-ylmethyl]-1H-1,2,4-triazole (bmt ligands. In addition, two bmt ligands link two AgI ions, forming a dinuclear unit with an Ag...Ag distance of 5.0179 (15 Å. The whole complex is generated by an inversion centre. The dinuclear units and the NO3− counter-ions are connected by N—H...O hydrogen bonds and weak Ag...O interactions [2.831 (5, 2.887 (5 and 2.908 (5 Å], leading to a three-dimensional structure.

  12. Synthesis and Crystal Structure of 2-Chloromethyl-1H-benzimidazole Nitrate, [ClCH2(C7H6N2)]NO3

    Institute of Scientific and Technical Information of China (English)

    建方方; 卑凤利; 汪信; 陆路德

    2003-01-01

    The title compound [ClCH2(C7H6N2)]NO3 has been prepared and characterized by elemental analysis and X-ray studies. It crystallizes in the monoclinic system, space group P21/n with a = 7.4189(3), b =15.3064(6), c = 9.2657(3) (A。),β = 102.449(2)o, C8H8ClN3O3, Mr = 229.62, V = 1027.44(7) (A。)3, Z = 4, Dc = 1.484 g/cm3, F(000) = 472, μ = 0.363 mm-1, R = 0.0671 and wR = 0.1546. The crystal structure consists of discrete 2-chloromethyl-1H-benzimidazole cations and NO3- anions. The benzimidazole ring with the conjunction carbon atom C(1) is fairly planar, with the deviation from the least plane through the ring atoms is smaller than 0.010(3) (A。). The analytical results of crystal structure show that three different non-covalent interactions in the compound, N-H…O intermolecular hydrogen bonds, C-H…O interaction and π-π stacking interaction, play an important role in the crystal packing.

  13. Chlorido[5-methoxy-1H-benzimidazole-2(3H-thione-κS]bis(triphenylphosphane-κPcopper(I methanol disolvate

    Directory of Open Access Journals (Sweden)

    Qing-Xuan Meng

    2014-02-01

    Full Text Available In the title complex, [CuCl(C8H8N2OS(C18H15P2]·2CH3OH, the CuI ion is coordinated by one chloride anion, one S atom from the 5-methoxy-1H-benzimidazole-2(3H-thione ligand and two P atoms from two triphenylphosphine ligands in a distorted tetrahedral geometry. One of the N-bound H atoms is involved in an intramolecular N—H...Cl hydrogen bond, while another one interacts with the solvent methanol molecule via an N—H...O hydrogen bond. Intermolecular O—H...Cl and O—H...O hydrogen bonds link two further complex molecules and four solvent molecules into a centrosymmetric structural unit. The short distance of 3.624 (4 Å between the centroids of the five- and the six-membered rings of two benzimidazole fragments indicates the presence of π–π interactions.

  14. Simultaneous determination of nitroimidazoles, benzimidazoles, and chloramphenicol components in bovine milk by ultra-high performance liquid chromatography-tandem mass spectrometry.

    Science.gov (United States)

    Wang, Yuanyuan; Li, Xiaowei; Zhang, Zhiwen; Ding, Shuangyang; Jiang, Haiyang; Li, Jiancheng; Shen, Jianzhong; Xia, Xi

    2016-02-01

    A sensitive, confirmatory ultra-high performance liquid chromatography-tandem mass spectrometric method was developed and validated to detect 23 veterinary drugs and metabolites (nitroimidazoles, benzimidazoles, and chloramphenicol components) in bovine milk. Compounds of interest were sequentially extracted from milk with acetonitrile and basified acetonitrile using sodium chloride to induce liquid-liquid partition. The extract was purified on a mixed mode solid-phase extraction cartridge. Using rapid polarity switching in electrospray ionization, a single injection was capable of detecting both positively and negatively charged analytes in a 9 min chromatography run time. Recoveries based on matrix-matched calibrations and isotope labeled internal standards for milk ranged from 51.7% to 101.8%. The detection limits and quantitation limits of the analytical method were found to be within the range of 2-20 ng/kg and 5-50 ng/kg, respectively. The recommended method is simple, specific, and reliable for the routine monitoring of nitroimidazoles, benzimidazoles, and chloramphenicol components in bovine milk samples.

  15. A study of vibrational spectra and investigations of charge transfer and chemical bonding features of 2-chloro benzimidazole based on DFT computations

    Science.gov (United States)

    Muthunatesan, S.; Ragavendran, V.

    2015-01-01

    Benzimidazoles are bicyclic heteroatomic molecules. Polycyclic heteroatomic molecules have extensive coupling of different modes leading to strong coupling of force constants associated with the various chemical bonds of the molecules. To carry out a detailed vibrational spectroscopic analysis of such a bicyclic heteroatomic molecule, FT-IR and FT-Raman spectra of 2-chloro benzimidazole (CBZ) have been recorded in the condensed phase. Density Functional Theory calculations in the B3LYP/6-31G* level have been carried out to determine the optimized geometry and vibrational frequencies. In order to obtain a close agreement between theoretical and observed frequencies and hence to perform a reliable assignment, the theoretical DFT force field was transformed from Cartesian to local symmetry co-ordinates and then scaled empirically using SQM methodology. The SQM treatment resulted in a RMS deviation of 9.4 cm-1. For visual comparison, the observed and calculated spectra are presented on a common wavenumber scale. From the NBO analysis, the electron density (ED) charge transfers in the σ* and π* antibonding orbitals and second order delocalization energies E(2) confirms the occurrence of intramolecular charge transfer (ICT) within the molecule. The calculated Homo and Lumo energies show that charge transfer occurs within the molecule. The results obtained from the vibrational, NBO and HOMO-LUMO analyses have been properly tabulated.

  16. Co(II), Ni(II) and Cu(II) complexes of methyl-5-(Phenylthio) benzimidazole-2-carbamate: Molecular structures, spectral and DFT calculations

    Science.gov (United States)

    Mansour, Ahmed M.; El Bakry, Eslam M.; Abdel-Ghani, Nour T.

    2016-05-01

    [Co(FBZ)2(H2O)]·2NO3·0.5H2O (1), [Ni(FBZ)2X2]·zH2O (X = Cl​-, z = 0.5 (2) and X = CH3COO-, z = 1 (3)) and [Cu(FBZ)2(H2O) (NO3)]·NO3·1.5H2O (4) (FBZ = methyl-5-(Phenylthio) benzimidazole-2-carbamate; Fenbendazole) complexes were synthesized and characterized by elemental analysis, thermal, IR, EPR, UV-Vis, magnetic and conductance measurements. Geometry optimization, molecular electrostatic potential maps and natural bond orbital analysis were carried out at DFT/B3LYP/6-31G∗ level of theory. FBZ behaves as a neutral bidentate ligand via the pyridine-type nitrogen of the benzimidazole moiety and the carbamate group. Three-step ionization with pKa values of 3.38, 4.06 and 10.07 were reported for FBZ. The coordination of FBZ to the metal ions led to an increase in the antibacterial activity against the tested Staphylococcus aureus and Escherichia coli bacteria.

  17. Biological evaluation of a cytotoxic 2-substituted benzimidazole copper(II) complex: DNA damage, antiproliferation and apoptotic induction activity in human cervical cancer cells.

    Science.gov (United States)

    Qiao, Xin; Ma, Zhong-Ying; Shao, Jia; Bao, Wei-Guo; Xu, Jing-Yuan; Qiang, Zhao-Yan; Lou, Jian-Shi

    2014-02-01

    Exploring novel chemotherapeutic agents is a great challenge in cancer medicine. To that end, 2-substituted benzimidazole copper(II) complex, [Cu(BMA)Cl2]·(CH3OH) (1) [BMA = N,N'-bis(benzimidazol-2-yl-methyl)amine], was synthesized and its cytotoxicity was characterized. The interaction between complex 1 and calf thymus DNA was detected by spectroscopy methods. The binding constant (K b = 1.24 × 10(4 )M(-1)) and the apparent binding constant (K app = 6.67 × 10(6 )M(-1)) of 1 indicated its moderate DNA affinity. Complex 1 induced single strand breaks of pUC19 plasmid DNA in the presence of H2O2 through an oxidative pathway. Cytotoxicity studies proved that complex 1 could inhibit the proliferation of human cervical carcinoma cell line HeLa in both time- and dose-dependent manners. The results of nuclei staining by Hoechst 33342 and alkaline single-cell gel electrophoresis proved that complex 1 caused cellular DNA damage in HeLa cells. Furthermore, treatment of HeLa cells with 1 resulted in S-phase arrest, loss of mitochondrial potential, and up-regulation of caspase-3 and -9 in HeLa cells, suggesting that complex 1 was capable of inducing apoptosis in cancer cells through the intrinsic mitochondrial pathway.

  18. Sorption-Desorption Behavior of Newly synthesized N-(1H-Benzimidazole -2 ylmethyl) Acetamide (ABNZ) on Selected Soils and its Antifungal activity

    International Nuclear Information System (INIS)

    A batch equilibrium method has been utilized to investigate the adsorption-desorption behavior of a versatile commercially available fungicide N-(1H-benzimidazole-2ylmethyl) acetamide (ABNZ) on four Pakistani soils geographically distant, from hilly to desert areas. Both qualitative and quantitative analysis has been done for sorption-desorption behavior of ABNZ. These analyses are done in the different concentration of fungicide (0-0.25, 0.25-0.5, 0.5-0.75). Based on statistical analysis ABNZ execute the Freundlich adsorption isotherm in all four tested soils having values of slope n<1 resembling the L-type curve. The distribution co-efficient K/sub d(ads)/ ranges from (2.66 to 12.42 ml/meu g/sup -1/) indicating low adsorption of ABNZ overall. Sorption increases with soil organic carbon content, exhibited greater degree of adsorption for hilly soil and least adsorption on sandy soil of Multan, Punjab. Desorption studies reveal that the adsorbed fungicide is firmly retained by soil particles and present a certain degree of irreversibility. The results indicate that the soil organic matters followed by clay content are the most important soil properties governing the fungicide sorption capacity. Compound N-(1H- benzimidazole -2-ylmethyl) acetamide (ABNZ) showed maximum antifungal activity compared to rest of the tested compound. This anti-fungal activity is substantial in comparison to other pesticides. It causes 40% inhibition of Microsporum canis and Fusarium solani. (author)

  19. Hexa-μ-chlorido-μ4-oxido-tetrakis({1-[(pyridin-2-ylmethyl]-1H-benzimidazole-κN3}copper(II

    Directory of Open Access Journals (Sweden)

    Hong Sun

    2011-10-01

    Full Text Available The title tetranuclear complex, [Cu4Cl6O(C13H11N34], features a tetrahedral arrangement of copper(II ions bonded to the central O atom (site symmetry overline{4}. Each of the six edges of the Cu4 tetrahedron is bridged by a chloride ion (one of which has site symmetry 2, so that each copper ion is linked to the other three metal ions through the central O atom and through three separate chloride-ion bridges. The fifth coordination position, located on the central Cu—O axis on the outside of the cluster, is occupied by an N atom of the monodentate 1-(pyridin-2-ylmethyl-1H-benzimidazole ligand. The resulting coordination geometry of the metal ion is a distorted trigonal bipyramid with the O and N atoms in the axial positions. The dihedral angle between the benzimidazole ring system and the pendant pyridine ring is 61.0 (2°.

  20. Synthesis and PASS-assisted in silico approach of some novel 2-substituted benzimidazole bearing a pyrimidine-2, 4, 6(trione system as mucomembranous protector

    Directory of Open Access Journals (Sweden)

    Bijo Mathew

    2013-01-01

    Full Text Available Purpose: The present paper demonstrates the utility of PASS computer-aided program and makes a clear comparison of predicted and observed pharmacological properties of some novel 5-[(2E-1-(1H-benzimidazol-2-yl-3-substituted phenylprop-2-en-1-ylidene] pyrimidine-2, 4, 6 (1H, 3H, 5H-triones (5a-f. Materials and Methods: The synthesis of the titled derivatives were achieved by the reaction between 2E-1-(1H-benzimidazol-2-yl-3-phenylprop-2-en-1-ones (4a-f and barbituric acid in the presence of catalytic amount of acetic acid medium. All the final structures were assigned on the basis of IR, 1 HNMR and mass spectra analysis. All the newly synthesized compounds were screened for their antiulcer activity in the pylorus-ligated rats. Results: Compounds 5b, 5e and 5c showed a percentage protection of (69.58, 69.56 and 67.17 at a dose of 50 mg/kg b.w. when compared to standard omeprazole (77.37%, 2 mg/kg b.w.. Conclusion: Scanning of stomach specimens using electron microscope revealed that the mice treated with standard and synthetic derivatives had no injury observed in stomach mucosa, which is identical to that of the control animal.

  1. Dose-dependent activity of albendazole against benzimidazole-resistant nematodes in sheep: relationship between pharmacokinetics and efficacy.

    Science.gov (United States)

    Moreno, L; Echevarria, F; Muñoz, F; Alvarez, L; Sanchez Bruni, S; Lanusse, C

    2004-01-01

    The relationship between the pharmacokinetic behaviour and the anthelmintic efficacy of albendazole (ABZ) against benzimidazole (BZD)-resistant nematodes was studied in sheep. A micronized ABZ suspension was orally administered at two different dose levels to sheep naturally infected with BZD-resistant gastrointestinal (GI) nematodes. The experimental animals were allocated into the following groups (n = 8): (a) untreated control; (b) orally treated with ABZ at 3.8 mg/kg b.w.; and (c) orally treated with ABZ at 7.5 mg/kg b.w. Plasma samples were obtained serially over 72 h post-treatment from both treated groups and analysed by HPLC to measure the concentrations of ABZ and its sulphoxide (ABZSO) and sulphone (ABZSO(2)) metabolites. Faecal egg counts were performed prior to treatment and at the necropsy day. All experimental animals were sacrificed 10 days after treatment to perform GI worm counts. While ABZ parent drug was not recovered in the bloodstream, ABZSO and ABZSO(2) were the molecules found in plasma. ABZSO was the metabolite measured at the highest concentrations in the bloodstream for up to 36 (treatment at 3.8 mg/kg) or 60 h (treatment at 7.5 mg/kg) post-administration. There was a proportional relationship between the administered ABZ dose and the measured plasma concentrations of both ABZ metabolites. Over a 100% increment on the plasma AUC values for the anthelmintically active ABZSO metabolite was observed at the 7.5 mg/kg compared to the 3.8 mg/kg treatment. The low efficacy patterns (< 24%) observed against the GI nematodes investigated indicate a high level of resistance to ABZ given at 3.8 mg/kg an efficacious therapeutic dose rate recommended in some countries. However, the higher and prolonged plasma drug concentration measured after the 7.5 mg/kg treatment resulted in an improved efficacy pattern (estimated by both faecal egg and adult worm counts) against most of the GI nematodes studied compared to that obtained at the lower dose rate. A

  2. Intracellular detection of Cu(2+) and S(2-) ions through a quinazoline functionalized benzimidazole-based new fluorogenic differential chemosensor.

    Science.gov (United States)

    Paul, Anup; Anbu, Sellamuthu; Sharma, Gunjan; Kuznetsov, Maxim L; Guedes da Silva, M Fátima C; Koch, Biplob; Pombeiro, Armando J L

    2015-10-14

    A new quinazoline functionalized benzimidazole-based fluorogenic chemosensor H3L is synthesized and fully characterized by conventional techniques including single crystal X-ray analysis. It acts as a highly selective colorimetric and fluorescence sensor for Cu(2+) ions in DMF/0.02 M HEPES (1 : 1, v/v, pH = 7.4) medium. Reaction of H3L with CuCl2 forms a mononuclear copper(ii) [Cu(Cl)(H2L)(H2O)] (H2L-Cu(2+)) complex which is characterized by conventional techniques and quantum chemical calculations. Electronic absorption and fluorescence titration studies of H3L with different metal cations show a distinctive recognition only towards Cu(2+) ions even in the presence of other commonly coexisting ions such as Li(+), Na(+), K(+), Mg(2+), Ca(2+), Fe(2+), Fe(3+), Mn(2+), Co(2+), Ni(2+), Zn(2+), Cd(2+) and Hg(2+). Moreover, H2L-Cu(2+) acts as a metal based highly selective and sensitive chemosensor for S(2-) ions even in the presence of other commonly coexisting anions such as F(-), Cl(-), Br(-), I(-), SO4(2-), SCN(-), AcO(-), H2PO4(-), PO4(3-), NO3(-), ClO4(-), NO2(-), HSO4(-), HSO4(2-), S2O3(2-), S2O8(2-), CN(-), CO3(2-) and HCO3(-) in DMF/0.02 M HEPES (1 : 1, v/v, pH = 7.4) medium. Quantification analysis indicates that these receptors, H3L and H2L-Cu(2+), can detect the presence of Cu(2+) and S(2-) ions at very low concentrations of 1.6 × 10(-9) M and 5.2 × 10(-6) M, respectively. The propensity of H3L as a bio-imaging fluorescent probe for detection of Cu(2+) ions and sequential detection of S(2-) ions by H2L-Cu(2+) in Dalton lymphoma (DL) cancer cells is also shown. PMID:26370442

  3. Copper nano composites functionalized by bis-benzimidazole diamide ligand: Effect of size, co-anion dependent conductivity and band gap studies

    Energy Technology Data Exchange (ETDEWEB)

    Singla, Manisha, E-mail: manishasingla@gmail.com [Dept. of Chemistry, University of Delhi, New Delhi (India); Mohapatra, Subash Chandra, E-mail: subashcm@gmail.com [Dept. of Chemistry, Jamia Millia Islamia, New Delhi (India); Ahmad, Sharif, E-mail: sharifahmad_jmi@yahoo.co.in [Dept. of Chemistry, Jamia Millia Islamia, New Delhi (India)

    2012-11-15

    Copper (I) and copper (II) nano composites capped with a bis-benzimidazole diamide ligand were prepared by reverse micelle method and characterized using CHNS, FTIR, {sup 1}H NMR, TEM and DLS studies. All particles were spherical ranging between 10 and 70 nm. They displayed a quasi reversible redox wave due to the Cu (II)/Cu (I) reduction process. The E{sub g1}{sup Prime} values shift anodically as NO{sub 3}{sup -} < Cl{sup -} < SCN{sup -}. Electrochemical HOMO and LUMO band gap (E{sub g1}{sup Prime }) for the nano composites were +1.80 (NO{sub 3}{sup -}), +2.80 (Cl{sup -}) and +4.10 (SCN{sup -}) eV, respectively. However, the optical band gap (E{sub g1}) for the nano composites was calculated from their absorption edges and lie between 1.77 and 4.13 eV. Fluorescence studies reveal that nano composites in themselves behave as an enhancer and quencher in respect to ligand, Quantum yield ({phi}) is varying from 0.008 to 0.02 photon. The activation energies range from 34 to 54 kJ mol{sup -1} and are quite low in comparison to that of the free bis-benzimidazole diamide ligand (137 kJ mol{sup -1}). The lower activation energies further re-emphasize the nano size of these composites. At room temperature, the dc conductivity lies between 1 Multiplication-Sign 10{sup -4}-9.33 Multiplication-Sign 10{sup -4} S cm{sup -1} [NO{sub 3}{sup -} > SCN{sup -} > Cl{sup -}] indicating them to be on the semiconductor insulator interface. The dielectric constant, dielectric loss and the ac conductivity were measured for all nano at room temperature and below the room temperature for the nano composite containing nitrate as co-anion. The conductivity was found to follow the correlated barrier hopping (CBH) mechanism; the exponent factor (s) varies from 0.5 to 1. -- Highlights: Black-Right-Pointing-Pointer Nano composites of copper, capped by bis benzimidazole diamide ligand. Black-Right-Pointing-Pointer Such copper nano composites have not been used in conductivity studies before. Black

  4. Acid-base blend membranes based on 2-amino-benzimidazole and sulfonated poly(ether ether ketone) for direct methanol fuel cells

    Energy Technology Data Exchange (ETDEWEB)

    Fu, Yongzhu; Manthiram, Arumugam [Materials Science and Engineering Program, The University of Texas at Austin, Austin, TX 78712 (United States); Guiver, Michael D. [Institute for Chemical Process and Environmental Technology, National Research Council of (Canada)

    2007-05-15

    Direct methanol fuel cells (DMFC) are attractive for portable and automobile power needs, but their commercialization is hampered by high methanol permeability and the high cost of the currently used Nafion membrane. We report here a novel, low-cost blend membrane consisting of polysulfone-2-amide-benzimidazole (a basic polymer) and sulfonated poly(ether ether ketone) (an acidic polymer), which facilitates proton conduction through acid-base interactions while preserving excellent chemical and mechanical stabilities. The blend membrane exhibits performance in DMFC much higher than that of Nafion 115 and similar to that of Nafion 112, but with a remarkably superior long-term performance than Nafion 112 due to significantly reduced methanol crossover, enhancing the commercialization prospects of DMFC. (author)

  5. Effect of optimized structure and electronic properties of some benzimidazole derivatives on corrosion inhibition of mild steel in hydrochloric acid medium: Electrochemical and theoretical studies

    Indian Academy of Sciences (India)

    Alokdut Dutta; Sujit Sankar Panja; M M Nandi; Dipankar Sukul

    2015-05-01

    The corrosion inhibitive action of a few benzimidazole derivatives namely 2-(benzamido) ethylbenzimidazole (BAEBI), 2-(-benzenesulphonamido) ethylbenzimidazole (BSAEBI), 2-(benzamido) methylbenzimidazole (BAMBI) and 2-(-benzenesulphonamido) methylbenzimidazole (BSAMBI), towards mild steel in hydrochloric acid has been studied using potentiodynamic polarization and electrochemical impedance spectroscopic (EIS) methods. The results show that these compounds get adsorbed on the mild steel surface following Temkin adsorption isotherm, and act as mixed-type inhibitors. The inhibition efficiencies are found to follow the order, BAEBI > BSAEBI > BAMBI > BSAMBI. This observation is explained in terms of chain length, relative effects of amido and sulphonamido groups, possible structural factors, spatial orientations, energy gap between the frontier molecular orbitals, different intrinsic molecular parameters, like, global hardness and softness, and number of electrons transferred.

  6. VUV photophysics and dissociative photoionization of pyrimidine, purine, imidazole and benzimidazole in the 7-18 eV photon energy range

    Energy Technology Data Exchange (ETDEWEB)

    Schwell, Martin [Laboratoire Interuniversitaire des Systemes Atmospheriques (LISA), CNRS-UMR 7583, Universite Paris 7 and 12, 61 Avenue du General de Gaulle, 94010 Creteil (France)], E-mail: schwell@lisa.univ-paris12.fr; Jochims, Hans-Werner; Baumgaertel, Helmut [Institut fuer Physikalische und Theoretische Chemie der Freien Universitaet Berlin, Takustr. 3, Berlin 14195 (Germany); Leach, Sydney [Laboratoire d' Etude du Rayonnement et de la Matiere en Astrophysique (LERMA), CNRS-UMR 8112, Observatoire de Paris-Meudon, 5 Place Jules-Janssen, 92195 Meudon (France)], E-mail: Sydney.Leach@obspm.fr

    2008-11-03

    Photoionization mass spectrometry is used to study ionization processes and fragmentation pathways of four prebiotic species, pyrimidine, purine, imidazole and benzimidazole, in the 7-18 eV photon energy region, with synchrotron radiation as excitation source. These molecules are possible precursors of the nucleic acid bases that occur in DNA and RNA. Ionization energies and ion appearance energies are reported. They are compared with electron impact and other studies and are discussed in terms of the electronic and nuclear structures of these species and their cations. The ion appearance energies, in conjunction with thermochemical data, were used to propose dissociative photoionization pathways, principally involving loss of HCN molecules in each of the four species. Astrophysical implications of the results concern the prospects for observation and survival of these molecules in the interstellar medium, in comets and in meteorites. Suggestions are made concerning suitable sites for radioastronomical searches for these purines and pyrimidines.

  7. Design, synthesis and biological evaluation of novel 5-fluoro-1H-benzimidazole-4-carboxamide derivatives as potent PARP-1 inhibitors.

    Science.gov (United States)

    Wang, Junwei; Wang, Xuyan; Li, Hui; Ji, Dezhong; Li, Yuyan; Xu, Yungen; Zhu, Qihua

    2016-08-15

    A series of novel 5-fluorine-benzimidazole-4-carboxamide analogs were designed and synthesized. All target compounds were evaluated for their PARP-1 inhibitory activity. Compounds possessed high intrinsic PARP-1 inhibitory potency have been evaluated in vitro cellular assays to measure the potentiation effect of cytotoxic agents against cancer cell line. These efforts led to the identification of compound 10f, which displayed strong inhibition against the PARP-1 enzyme with an IC50 of 43.7nM, excellent cell inhibitory activity in HCT116 cells (IC50=7.4μM) and potentiation of temozolomide cytotoxicity in cancer cell line A549 (PF50=1.6). PMID:27353531

  8. Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO and NBO analysis of 5-chloro-2-((4-chlorophenoxy)methyl)benzimidazole

    Science.gov (United States)

    Mary, Y. Shyma; Jojo, P. J.; Panicker, C. Yohannan; Van Alsenoy, Christian; Ataei, Sanaz; Yildiz, Ilkay

    2014-03-01

    The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-chloro-2-((4-chlorophenoxy)methyl)benzimidazole have been investigated experimentally and theoretically using Gaussian09 software package. The energy and oscillator strength calculated by time dependent density functional theory results almost compliments with experimental findings. Gauge-including atomic orbital 1H NMR chemical shifts calculations were carried out and compared with experimental data. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. Molecular electrostatic potential was performed by the DFT method and the infrared intensities and Raman activities are reported. Mulliken's net charges have been calculated and compared with the atomic natural charges. Fist hyperpolarizability is calculated in order to find its role in non-linear optics.

  9. Relay recognition of Cu2+ and S2- in water by a simple 2-(2";-aminophenyl)benzimidazole derivatized fluorescent sensor through modulating ESIPT

    Science.gov (United States)

    Tang, Lijun; Dai, Xin; Cai, Mingjun; Zhao, Jia; Zhou, Pei; Huang, Zhenlong

    2014-03-01

    A new 2-(2";-aminophenyl)benzimidazole (2-APBI) derivatized fluorescent sensor (L) that behaves relay recognition of Cu2+ and S2- in water solution (pH 7.4) has been developed. Sensor L displays excited-state intramolecular proton transfer (ESIPT) featured two emission bands and performs highly selective and sensitive recognition to Cu2+ through two emissions simultaneous quenching. The on-site formed L-Cu2+ complex exhibits excellent selectivity to S2- with fluorescence "off-on" response via Cu2+ displacement approach, which exerts ESIPT recovery. Thus, through modulation the ESIPT state of sensor L, relay recognition of Cu2+ and S2- in water has been achieved.

  10. catena-Poly[[(diiodidocadmium-μ-{1-[(1H-benzimidazol-2-ylmethyl]-1H-imidazole-κ2N:N′}] N,N-dimethylformamide monosolvate

    Directory of Open Access Journals (Sweden)

    Bingtao Liu

    2011-12-01

    Full Text Available In the title complex, {[CdI2(C11H10N4]·C3H7NO}n, the CdII ion is four-coordinated by two N atoms from two 1-[(1H-benzimidazol-1-ylmethyl]-1H-imidazole (bmi ligands and by two terminal I− anions in a distorted tetrahedral geometry. One of the two I− anions is disordered over two sets of sites, with refined occupancies of 0.66 (5 and 0.34 (5. The CdII ions are bridged by bmi ligands, leading to the formation of a chain along [001]. Dimethylformamide solvent molecules are located between these chains. Classical N—H...O hydrogen bonding between the bmi ligands and the solvent molecules leads to a consolidation of the structure.

  11. Bis[2-(2-aminoethyl-1H-benzimidazole-κ2N2,N3](nitrato-κ2O,O′cobalt(II chloride trihydrate

    Directory of Open Access Journals (Sweden)

    Jing Zhao

    2012-06-01

    Full Text Available In the title compound, [Co(NO3(C9H11N32]Cl·3H2O, the CoII atom is coordinated by four N atoms from two chelating 2-(2-aminoethyl-1H-benzimidazole ligands and two O atoms from one nitrate anion in a distorted octahedral coordination environment. In the crystal, N—H...Cl, N—H...O, O—H...Cl and O—H...O hydrogen bonds link the complex cations, chloride anions and solvent water molecules into a three-dimensional network. π–π interactions between the imidazole and benzene rings and between the benzene rings are observed [centroid–centroid distances = 3.903 (3, 3.720 (3, 3.774 (3 and 3.926 (3 Å].

  12. Lanthanide(III and Yttrium(III Complexes of Benzimidazole-2-Acetic Acid: Synthesis, Characterisation and Effect of La(III Complex on Germination of Wheat

    Directory of Open Access Journals (Sweden)

    2006-01-01

    Full Text Available The synthesis and characterisation of lanthanide(III and yttrium(III nitrate complexes of benzimidazole-2-acetic acid (HBIA are reported. The complexes have been characterised by elemental analysis, molar conductance, magnetic studies, IR, 1 H NMR, UV-visible, EPR, and TG/DTA studies. They have the stoichiometry [ Ln 3 ( BIA 2 ( NO 3 7 ( H 2 O 4 ]⋅3 H 2 O where Ln=La(III, Pr(III, Nd(II, Sm(III, Eu(III, Gd(III, Tb(III, Dy(III, and Y(III. The effect of La(III complex on germination, coleoptile, and root length of two local varieties of wheat DWR-195 and GW-349 for different treatment periods has been investigated. The complex was found to exhibit enhanced activity, compared to HBIA or metal salt alone at lower treatment periods.

  13. Chloridobis[2-(1,3-thiazol-4-yl-κN-1H-benzimidazole-κN3]cobalt(II chloride dihydrate

    Directory of Open Access Journals (Sweden)

    Zhan-Wang Shi

    2012-08-01

    Full Text Available In the title compound, [CoCl(C10H7N3S2]Cl·2H2O, the CoII atom is five-coordinated by four N atoms from two chelating 2-(1,3-thiazol-4-yl-1H-benzimidazole ligands and one Cl atom in a distorted trigonal–bipyramidal geometry. In the crystal, N—H...O and O—H...Cl hydrogen bonds and π–π interactions between the thiazole, imidazole and benzene rings [centroid-to-centroid distances 3.546 (2, 3.683 (2 and 3.714 (2 Å] link the complex cations, chloride anions and uncoordinating water molecules into a three-dimensional network.

  14. Synthesis, Characterization, Spectroscopic Properties of 2-(4-Dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole and its Interaction with Calf Thymus DNA

    Institute of Scientific and Technical Information of China (English)

    Ling Tian TANG; Yi WANG; Xin Qi LIU; Shao Wen HU; Tai Wei CHU; Xiang Yun WANG

    2005-01-01

    2-(4-Dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)- 1H-benzimidazole(1) has been synthesized and characterized by 1H-NMR, MS and elemental analysis. UV-Vis spectra of the aqueous solutions at different pH values reveal that compound 1 can combine three protons. Its three protonation constants are determined by spectrophotometry and calculated by non-linear least squares. The results of steady-state fluorescence measurements indicate that a special interaction occurs between compound 1 and calf thymus DNA, of which the binding constant, Kb, is (2.30 ±0.10)×l04 L/mol. Compound 1 in the concentration range of 10-8 to 1.2×l0-6 mol/L could be used for quantitative determination of DNA.

  15. Crystal structures and luminescence properties of two Cd(II) complexes based on 2-(1H-imidazol-1methyl)-6-methyl-1H-benzimidazole

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, Yuhong; Meng, Xiangru; Wen, Yu; Li, Peng; Ma, Lin [Zhengzhou Univ. (China). College of Chemistry and Molecular Engineering; Zhang, Qiuju [Zhengzhou Univ. (China). Clinical Testing Section

    2015-11-01

    Two new complexes, {[Cd(immb)I_2].DMF}{sub n} (1) and {[Cd_3(immb)(btc)_2]. H_2O}{sub n} (2) (immb = 2-(1H-imidazol- 1-methyl)-6-methyl-1H-benzimidazole, btc = 1,2,3-benzenetricarboxylate, DMF = dimethyl formamide), have been synthesized and characterized. Single crystal X-ray diffraction shows that 1 exhibits a chain structure constructed by immb ligands bridging Cd(II) ions. In 2, Cd(II) ions are linked by immb ligands with bridging mode and btc3- anions with the μ{sub 2}-η{sup 2}:η{sup 1} bonding pattern leading to a 2D structure. Luminescent properties have been investigated in the solid state at room temperature.

  16. Structural studies of series HIV-1 nonnucleoside reverse transcriptase inhibitors 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazoles with different 4-substituents

    Science.gov (United States)

    Ziółkowska, Natasza E.; Michejda, Christopher J.; Bujacz, Grzegorz D.

    2010-03-01

    Over the past 10 years, several anti-viral drugs have become available to fight the HIV infection. Antiretroviral treatment reduces the mortality of AIDS. Nonnucleoside inhibitors of HIV-1 reverse transcriptase are specific and potentially nontoxic drugs against AIDS. The crystal structures of five nonnucleoside inhibitors of HIV-1 reverse transcriptase are presented here. The structural parameters, especially those describing the angular orientation of the π-electron systems and influencing biological activity, were determined for all of the investigated inhibitors. The chemical character and orientation of the substituent at C4 position of the benzimidazole moiety substantially influences the anti-viral activity. The structural data of the investigated inhibitors is a good basis for modeling enzyme-inhibitor interactions for structure-assisted drug design.

  17. 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.

  18. Novel coordination polymers with 1,4-di(benzimidazole-1-yl)benzene modulated by an anion:Syntheses,structures and properties

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    Three novel coordination polymers, {[Co(L)(SO4)(H2O)](CH3OH)}∞ (1), {[Cd(L)2(SiF6)](H2O)}∞ (2) and [Zn(L)(NO3)2]∞ (3), synthesized from 1,4-di(benzimidazole-1-yl)benzene (L), have been characterized by infrared spectroscopy, elemental analysis and single crystal X-ray diffraction. Compounds 1-3 exhibit different structures. Complex 1 has a 3-D diamond network containing 1-D CoII chains connected by SO24- anions; 2 has a 3-D α-Po framework with 1-D porous channels along the c axis; and 3 has a 1-D zig-zag chain structure with a 2-D supramolecular network based on π-π interactions. The magnetic properties of 1 and the solid state fluorescence spectra of 2 and 3 have also been explored.

  19. Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.

    Science.gov (United States)

    Lee, Sang-Yong; Perotti, Arianna; De Jonghe, Steven; Herdewijn, Piet; Hanck, Theodor; Müller, Christa E

    2016-07-15

    Ecto-nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) is the most important member of the NPP family, which consists of seven closely related proteins (NPP1-NPP7). This glycoprotein is a membrane-associated or secreted enzyme, which catalyzes the hydrolysis of a wide range of phosphodiester bonds, e.g., in nucleoside triphosphates, dinucleotides and nucleotide sugars. NPP1 plays a crucial role in various physiological functions including bone mineralization, soft-tissue calcification, and insulin receptor signaling. Recently, an upregulated expression of NPP1 has been observed in astrocytic brain cancers. Therefore, NPP1 has been proposed as a novel drug target for the treatment of glioblastoma. Despite their therapeutic potential, only few NPP1 inhibitors have been reported to date, which are in most cases non- or only moderately selective. The best investigated NPP1 inhibitors so far are nucleotide derivatives and analogs, however they are not orally bioavailable due to their high polarity. We identified thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives as a new class of NPP1 inhibitors with drug-like properties. Among the 25 derivatives investigated in the present study, 2-[(5-iodo-2-furanyl)methylene]thiazolo[3,2-a]benzimidazol-3(2H)-one (17) was found to be the most potent NPP1 inhibitor with a Ki value of 467nM versus ATP as a substrate and an un-competitive mechanism of inhibition. Compound 17 did not inhibit other human ecto-nucleotidases, including NTPDase1 (CD39), NTPDases2-3, NPP2, NPP3, tissue-nonspecific alkaline phosphatase (TNAP), and ecto-5'-nucleotidase (eN, CD73), and is thus highly selective for NPP1. PMID:27265686

  20. Conformation driven complexation of two analogous benzimidazole based tripodal ligands with Ag(I) resulting in a trigonal prism and a coordination polymer

    Indian Academy of Sciences (India)

    Suman Bhattacharya; Binoy K Saha

    2016-02-01

    Two analogous tripodal ligands, namely, 1,3,5-tris(benzimidazol-1-ylmethyl)-2,4,6-triethylbenzene (1-Et) and 1,3,5-tris(benzimidazol-1-ylmethyl)-2,4,6-trimethoxybenzene (1-OMe) have been used for complexation with silver(I) tetrafluoroborate. A trinuclear Ag(I) salt, formulated as $\\mathbf{[Ag_3(1-Et)_2]^{3+}(BF_4){}^{−}_{3}\\bullet 7CH_3CN\\bullet yH_2O}$ was formed in the complexation reaction of 1-Et with silver(I) tetrafluoroborate, which consists of a trigonal prismatic cation formed by three bicoordinated Ag(I) coordinated with two 1-Et ligands. In case of the 1-OMe ligand, however, a one dimensional ladder, formulated as $\\mathbf{[(Ag(1-OMe)OH_2)^{+}(BF_4)^{−}\\bullet MeOH]_{\\infty}}$ was obtained which is constituted of a tetracoordinated Ag(I) center in a distorted tetrahedral environment. The crystal structures of the ligand hydrates namely $\\mathbf{1-Et\\bullet H_2O}$ and $\\mathbf{1-OMe\\bullet 3.6H_2O}$ have been discussed along with the structure of methanol solvate-hydrate of 1-Et. The imidazole rings of the Bim groups in 1-Et in the crystal structures of the ligand as well as in its coordination complex with the Ag(I) are pointed inward with respect to the central ring, whereas it is pointed outwards in the crystal structures of 1-OMe as well as its Ag(I) complex.

  1. Synthesis, DNA binding, cellular DNA lesion and cytotoxicity of a series of new benzimidazole-based Schiff base copper(II) complexes.

    Science.gov (United States)

    Paul, Anup; Anbu, Sellamuthu; Sharma, Gunjan; Kuznetsov, Maxim L; Koch, Biplob; Guedes da Silva, M Fátima C; Pombeiro, Armando J L

    2015-12-14

    A series of new benzimidazole containing compounds 2-((1-R-1-H-benzimidazol-2-yl)phenyl-imino)naphthol HL(1-3) (R = methyl, ethyl or propyl, respectively) have been synthesized by Schiff base condensation of 2-(1-R-1-H-benzo[d]imidazol-2-yl)aniline and 2-hydroxy-1-naphthaldehyde. The reactions of HL(1-3) with Cu(NO3)2·2.5H2O led to the corresponding copper(II) complexes [Cu(L)(NO3)] 1-3. All the compounds were characterized by conventional analytical techniques and, for 1 and 3, also by single-crystal X-ray analysis. The interactions of complexes 1-3 with calf thymus DNA were studied by absorption and fluorescence spectroscopic techniques and the calculated binding constants (K(b)) are in the range of 3.5 × 10(5) M(-1)-3.2 × 10(5) M(-1). Complexes 1-3 effectively bind DNA through an intercalative mode, as proved by molecular docking studies. The binding affinity of the complexes decreases with the size increase of the N-alkyl substituent, in the order of 1 > 2 > 3, which is also in accord with the calculated LUMO(complex) energies. They show substantial in vitro cytotoxic effect against human lung (A-549), breast (MDA-MB-231) and cervical (HeLa) cancer cell lines. Complex 1 exhibits a significant inhibitory effect on the proliferation of the A-549 cancer cells. The antiproliferative efficacy of 1 has also been analysed by a DNA fragmentation assay, fluorescence activated cell sorting (FACS) and nuclear morphology using a fluorescence microscope. The possible mode for the apoptosis pathway of 1 has also been evaluated by a reactive oxygen species (ROS) generation study.

  2. Vibrationally resolved ¹Lb (¹A')↔S0 (¹A') electronic spectra of benzimidazole and indene: Influence of Duschinsky and Herzberg-Teller effects on weak dipole-allowed transitions.

    Science.gov (United States)

    Yang, Pan; Pang, Min; Li, Ming; Shen, Wei; He, Rongxing

    2015-12-01

    Geometrical optimizations of the ground and first excited states of benzimidazole and indene were performed using the density functional theory (DFT) and its time-dependent extension methods (TD-DFT), respectively. Their vibrationally resolved (1)Lb ((1)A')↔S0 ((1)A') absorption and fluorescence spectra were simulated within the Franck-Condon approximation including the Herzberg-Teller (HT) and Duschinsky effects. Calculated results revealed that, with the HT and Duschinsky effects getting involved, the simulated weak (1)Lb ((1)A')↔S0 ((1)A') electronic spectra of the two molecules excellently reproduce the experimental findings. Based on the experimental data and other theoretical results, we tentatively assigned most of the vibrational normal modes which emerged in the experimental spectra of the two molecules. The present theoretical insights are expected to help us understand the nature of electronic transitions in the vibrationally resolved absorption and fluorescence spectra of benzimidazole and its analogues.

  3. 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.

  4. Vibrationally resolved ¹Lb (¹A')↔S0 (¹A') electronic spectra of benzimidazole and indene: Influence of Duschinsky and Herzberg-Teller effects on weak dipole-allowed transitions.

    Science.gov (United States)

    Yang, Pan; Pang, Min; Li, Ming; Shen, Wei; He, Rongxing

    2015-12-01

    Geometrical optimizations of the ground and first excited states of benzimidazole and indene were performed using the density functional theory (DFT) and its time-dependent extension methods (TD-DFT), respectively. Their vibrationally resolved (1)Lb ((1)A')↔S0 ((1)A') absorption and fluorescence spectra were simulated within the Franck-Condon approximation including the Herzberg-Teller (HT) and Duschinsky effects. Calculated results revealed that, with the HT and Duschinsky effects getting involved, the simulated weak (1)Lb ((1)A')↔S0 ((1)A') electronic spectra of the two molecules excellently reproduce the experimental findings. Based on the experimental data and other theoretical results, we tentatively assigned most of the vibrational normal modes which emerged in the experimental spectra of the two molecules. The present theoretical insights are expected to help us understand the nature of electronic transitions in the vibrationally resolved absorption and fluorescence spectra of benzimidazole and its analogues. PMID:26143330

  5. A colloidal suspension of nanostructured poly(N-butyl benzimidazole)-graphene sheets with high oxidase yield for analytical glucose and choline detections.

    Science.gov (United States)

    Chen, Hsiao-Chien; Tsai, Rung-Ywan; Chen, Yen-Hsuan; Lee, Ren-Shen; Hua, Mu-Yi

    2013-08-20

    A colloidal suspension of nanostructured poly(N-butyl benzimidazole)-graphene sheets (PBBIns-Gs) was used to modify a gold electrode to form a three-dimensional PBBIns-Gs/Au electrode that was sensitive to hydrogen peroxide (H2O2) in the presence of acetic acid (AcOH). The positively charged nanostructured poly(N-butyl benzimidazole) (PBBIns) separated the graphene sheets (Gs) and kept them suspended in an aqueous solution. Additionally, graphene sheets (Gs) formed "diaphragms" that intercalated Gs, which separated PBBIns to prevent tight packing and enhanced the surface area. The PBBIns-Gs/Au electrode exhibited superior sensitivity toward H2O2 relative to the PBBIns-modified Au (PBBIns/Au) electrode. Furthermore, a high yield of glucose oxidase (GOD) on the PBBIns-Gs of 52.3mg GOD per 1mg PBBIns-Gs was obtained from the electrostatic attraction between the positively charged PBBIns-Gs and negatively charged GOD. The non-destructive immobilization of GOD on the surface of the PBBIns-Gs (GOD-PBBIns-Gs) retained 91.5% and 39.2% of bioactivity, respectively, relative to free GOD for the colloidal suspension of the GOD-PBBIns-Gs and its modified Au (GOD-PBBIns-Gs/Au) electrode. Based on advantages including a negative working potential, high sensitivity toward H2O2, and non-destructive immobilization, the proposed glucose biosensor based on an GOD-PBBIns-Gs/Au electrode exhibited a fast response time (5.6s), broad detection range (10μM to 10mM), high sensitivity (143.5μAmM(-1)cm(-2)) and selectivity, and excellent stability. Finally, a choline biosensor was developed by dipping a PBBIns-Gs/Au electrode into a choline oxidase (ChOx) solution for enzyme loading. The choline biosensor had a linear range of 0.1μM to 0.83mM, sensitivity of 494.9μAmM(-1)cm(-2), and detection limit of 0.02μM. The results of glucose and choline measurement indicate that the PBBIns-Gs/Au electrode provides a useful platform for the development of oxidase-based biosensors. PMID:23910974

  6. Genetic evidence for the spread of a benzimidazole resistance mutation across southern India from a single origin in the parasitic nematode Haemonchus contortus.

    Science.gov (United States)

    Chaudhry, Umer; Redman, Elizabeth M; Raman, Muthusamy; Gilleard, John S

    2015-09-01

    It is important to understand how anthelmintic drug resistance mutations arise and spread in order to determine appropriate mitigation strategies. We hypothesised that a molecular genetic study of Haemonchus contortus in southern India, a region where resistance may be less advanced than in western Europe and North America, might provide some important insights into the origin and spread of anthelmintic resistance. The F200Y (TAC) isotype-1 β-tubulin benzimidazole resistance mutation is common in H. contortus throughout the world and the F167Y (TAC) and E198A (GCA) mutations, although less common, have been reported in a number of different countries. We have investigated the haplotypic diversity and phylogenetic relationship of isotype-1 β-tubulin benzimidazole resistance alleles for 23 H. contortus populations from small ruminants across southern India. The F200Y (TAC) mutation was most common, being detected in 18/23 populations at frequencies between 9% and 84% and the E198A (GCA) mutation was also detected in 8/23 populations at frequencies between 8% and 18%. The F167Y (TAC) mutation was not detected in any of the 23 populations. Phylogenetic haplotype network analysis suggested that the F200Y (TAC) mutation has arisen multiple independent times in the region with at least three independent origins of resistance alleles across the populations surveyed. In contrast, the E198A (GCA) mutation was present on a single haplotype which, given the high level of haplotypic diversity of the susceptible alleles in the region, suggests this particular mutation has spread from a single origin, likely by anthropogenic animal movement. Population genetic analysis of 12 of the H. contortus populations, using a panel of eight microsatellite markers, revealed extremely low genetic differentiation between populations, consistent with the hypothesis of high gene flow among sites. Additionally, there was no significant genetic differentiation between H. contortus taken from

  7. A study (1977-1992) of population dynamics of endoparasites featuring benzimidazole-resistant small strongyles (population S) in Shetland ponies.

    Science.gov (United States)

    Lyons, E T; Tolliver, S C; Drudge, J H; Stamper, S; Swerczek, T W; Granstrom, D E

    1996-11-01

    Critical tests (91) were done between 1977 and 1992 in Shetland ponies to evaluate drug susceptibility and population dynamics (present paper) of endoparasites. The test ponies, most less than 1 year old, were from a herd where older animals were treated every 8 weeks initially with cambendazole (CBZ) (1974-1978) and then with oxibendazole (OBZ) (1978-1992). Previous field test data (1974-1992) on older ponies in the breeding herd indicated the presence of benzimidazole (BZ) resistant small strongyles. Data on population dynamics from the present critical tests indicated that 28 species of small strongyles persisted over the study period in spite of initial susceptibility and later refractiveness of six species to both CBZ and OBZ. Changes in intensities and other aspects were observed for the six BZ-resistant species (Cyathostomum catinatium, Cyathostomum coronatum, Cylicocyclus nassatus, Cylicostephanus calicatus, Cylicostephanus goldi, and Cylicostephanus longibursatus). Variabilities, some striking, were found in prevalence and intensity in bots, stomach worms, ascarids, eyeworms, large strongyles, pinworms and tapeworms.

  8. Synthesis and Crystal Structure of a Dinuclear Cobalt(II) Complex [Co2(1H-benzimidazole)4(1,4-bdoa)2

    Institute of Scientific and Technical Information of China (English)

    GAO Shan; LIU Ji-Wei; HUO Li-Hua; ZHAO Hui

    2005-01-01

    A novel dinuclear complex with an empirical formula [Co2(1H-benzimidazole)4(1, 4-bdoa)2] (1,4-bdoa2- = benzene-1,4-dioxyacetate dianion) has been synthesized and characterized by elemental analysis, IR and single-crystal X-ray diffraction. It crystallizes in monoclinic system, space group P21/c with a = 11.000(2), b = 19.385(4), c = 11.417(2)(A), β = 95.49(3)°, V = 2423.3(8) (A)3, Z = 2, Mr = 1074.77, Dc = 1.473 g/cm3, μ = 0.760 mm-1, F(000) = 1108, the final R = 0.0645 and wR = 0.0714 for 3273 observed reflections (I > 2σ(I)). Two octahedrally coordinated Co(II) atoms are bridged by two 1,4-bdoa2- groups, generating a macrocyclic ring complex. The Co…Co separa- tion is 7.677(3) (A). An extended 3-D supramolecular network is formed through hydrogen bonds and weak π-π stacking interactions.

  9. Four 1-D metal-organic polymers self-assembled from semi-flexible benzimidazole-based ligand: Syntheses, structures and fluorescent properties

    Science.gov (United States)

    Zhou, Chun-lin; Wang, Shi-min; Liu, Sai-nan; Yu, Tian-tian; Li, Rui-ying; Xu, Hong; Liu, Zhong-yi; Sun, Huan; Cheng, Jia-jia; Li, Jin-peng; Hou, Hong-wei; Chang, Jun-biao

    2016-08-01

    Four one-dimensional (1-D) metal-organic polymers based on methylene-bis(1,1‧-benzimidazole)(mbbz), namely, {[Hg(mbbz)(SCN)2]·1/3H2O}n (1), [Co(mbbz)(Cl)2]n (2), {[Co(mbbz)(SO4)]·CH3OH}n (3) and {[Zn(mbbz)(SO4)]·CH3OH}n (4) have been successfully synthesized and structurally characterized. Single-crystal X-ray diffraction reveals that polymers 1 and 2 exhibit interesting 1-D double helical chain structures, while polymers 3 and 4 are 1-D double chain structures due to the bridging effect of mbbz ligands and sulfate anions. These polymers containing the mbbz-based ligand have a high degree of dependence on the corresponding counter anions. Furthermore, the fluorescence properties of the four polymers were also investigated in the solid state, showing the fluorescence signal changes in comparing with that of free ligand mbbz.

  10. Quantum chemical vibrational study, molecular property, FTIR, FT-Raman spectra, NBO, HOMO-LUMO energies and thermodynamic properties of 1-methyl-2-phenyl benzimidazole

    Science.gov (United States)

    Karnan, M.; Balachandran, V.; Murugan, M.; Murali, M. K.

    2014-09-01

    The solid phase FT-IR and FT-Raman spectra of 1-methyl-2-phenyl benzimidazole (MPBZ) have been recorded in the condensed state. In this work, experimental and theoretical study on the molecular structure, quantum chemical calculations of energies and vibrational wavenumbers of MPBZ is presented. The vibrational frequencies of the title compound were obtained theoretically by DFT/B3LYP calculations employing the standard 6-311+G(d,p) and 6-311++G(d,p) basis set for optimized geometry and were compared with Fourier transform infrared spectrum (FTIR) in the region of 4000-400 cm-1 and with Fourier transform Raman spectrum in the region of 4000-100 cm-1. Complete vibrational assignments, analysis and correlation of the fundamental modes for the title compound were carried out. The vibrational harmonic frequencies were scaled using scale factor, yielding a good agreement between the experimentally recorded and the theoretically calculated values. The study is extended to calculate the HOMO-LUMO energy gap, NBO, mapped molecular electrostatic potential (MEP) surfaces, polarizability, Mulliken charges and thermodynamic properties of the title compound.

  11. Growth of organic benzimidazole (BMZ) single crystal by vertical Bridgman technique and its structural, spectral, thermal, optical, mechanical and dielectric properties

    Science.gov (United States)

    Muthuraja, A.; Kalainathan, S.

    2015-09-01

    Benzimidazole (BMZ) single crystal was successfully grown by the vertical Bridgman technique (VBT). The crystal system was identified and lattice parameters have been measured from the powder X-ray diffraction (PXRD) measurement. Fourier transforms infrared spectral studies have been carried out to find out the functional groups of BMZ crystal. The optical transmittance and the cut-off wavelength of BMZ were identified using UV-Vis NIR studies and the cut-off wavelength was found to be 294 nm. The dielectric permittivity and dielectric loss as a function of frequency and temperature was measured for the grown BMZ crystal. Vickers microhardness analysis was carried out to identify the mechanical stability of the grown crystal. Chemical etching study was carried out using different etchants and the etch pit density (EPD) was calculated and compared. The third order nonlinear optical property of BMZ crystal was studied by using Z-scan technique with He-Ne laser (632.8 nm). The magnitude of nonlinear refractive index (n2), nonlinear absorption (β) and third order nonlinear susceptibility (χ3) have been found to be in the range of 10-11 m2/W, 10-4 m/W and 10-5 esu respectively. Photoluminescence spectrum was recorded using a xenon lamp in the range of 330-585 nm and it exhibits ultraviolet light emission.

  12. Study on the interaction between three benzimidazole anthelmintics and eosin Y by high performance liquid chromatography associating with resonance light scattering and its application.

    Science.gov (United States)

    Pan, Ziyu; Peng, Jingdong; Zang, Xu; Lei, Gang; He, Yan; Liu, Di

    2016-07-01

    A novel, highly selective, and sensitive resonance light scattering (RLS) detection approach coupled with high performance liquid chromatography (HPLC) was researched and developed for the synchronous analysis of three kinds of benzimidazole anthelmintics, including mebendazole (MBZ), albendazole (ABZ), and fenbendazole (FBZ) for the first time. In the pH range of 3.5-3.7 Britton-Robinson buffer medium, three kinds of anthelmintics, which were separated by HPLC, reacted with eosin Y (EY) to form 1:1 ion-association complexes, resulting in significantly enhanced RLS signals and the maximum peak located at 335 nm. The enhanced RLS intensity was in proportion to the MBZ, ABZ, and FBZ concentration in the range 0.2-25, 0.2-23, and 0.15-20 μg/mL, respectively. The limit of detection was in the range of 0.064-0.16 μg/mL. In addition, human urine was determined to validate the proposed method by spiked samples and real urine samples. Satisfactory results were obtained by HPLC-RLS method. Graphical Abstract The diagram mechanism of generating resonance between emitted light and scattered light. PMID:27209593

  13. 6-[2-(4-Arylpiperazin-1-ylethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation

    Directory of Open Access Journals (Sweden)

    DEANA ANDRIC

    2007-08-01

    Full Text Available Eight new compounds with halogen atom introduced into the benzimi­dazo­le-2-thione dopaminergic pharmacophore of 5-[2-(4-arylpiperazin-1-ylethyl]-1,3-dihy­dro-2H-benzimidazole-2-thiones with the arylpiperazine part of the molecule being selected according to known structure–affinity requirements, have been syn­thesized. All the new compounds were evaluated for the in vitro binding affinity at the dopa­mine (DA D1 and D2 and serotonin 5-HT1A receptors by the competitive radioas­says, performed on synaptosomal membranes prepared from fresh bovine caudate nuclei and hippocampi. All the new compounds were strong competitors for the bin­d­ing of the radioligands to the D2 and 5-HT1A receptors, with the most active of them having 34 and 170 time higher affinity than non-halogenated congeners in the D2 DA receptor radioassays (compounds 9.1b and 9.2b, respectively. Diver­gently, the­se compounds were without significant affinities for the D1 DA receptors.

  14. Impact of the different electron-releasing subunits on the dye-sensitized solar cell performance of new triphenylamine-benzimidazole based molecules

    Science.gov (United States)

    Dinçalp, Haluk; Saltan, Gözde Murat; Aykut, Deniz; Zafer, Ceylan

    2015-10-01

    New triphenylamine-benzimidazole type small molecules with different electron-releasing groups were designed and synthesized to investigate their photovoltaic performances in dye sensitized solar cells (DSSCs). Their good visible absorptions covering the 400-535 nm in addition to suitable lowest unoccupied molecular orbital (LUMO) energy levels between -3.03 and -3.11 eV make good candidates them for DSSC devices. Fluorescence quenching studies of the dyes with pristine titania support the good electron injection to conduction band of TiO2. Time resolved measurements of the dyes in solutions indicate the occurence of charge generation during the excited state. One of the used dyes in DSSC devices, TPA5a, carrying a methoxy group in triphenylamine part of the structure, gave much higher power conversion efficiency (PCE) value of 4.31% as compared to the other derivatives. Device fabricated from TPA5a dye gives good external quantum efficiency (EQE) value above 70% at 460 nm. Also, electron impedance spectroscopy (EIS) analysis of the devices gives a good explanation of the understanding of the cell performances.

  15. Analysis of molecular electronic structure of imidazole- and benzimidazole-based inhibitors: A simple recipe for qualitative estimation of chemical hardness

    Energy Technology Data Exchange (ETDEWEB)

    Kovacevic, Natasa [Department of Physical and Organic Chemistry, Jozef Stefan Institute, Jamova 39, SI-1000 Ljubljana (Slovenia); Kokalj, Anton, E-mail: tone.kokalj@ijs.s [Department of Physical and Organic Chemistry, Jozef Stefan Institute, Jamova 39, SI-1000 Ljubljana (Slovenia)

    2011-03-15

    Research highlights: {yields} Electronic structure of imidazole and benzimidazole type corrosion inhibitors is assessed by quantum chemical calculations. {yields} Simple recipe for estimating chemical hardness trend of chemically similar inhibitor molecules is presented. {yields} Effect of various substituents on the molecular electronic structure and solvation free energy is explained. {yields} Possible implications to adsorption and consequent inhibition of corrosion are discussed. - Abstract: The effect of methyl, phenyl, and mercapto substituents on electronic structure of imidazole type inhibitors was characterized by density-functional-theory calculations. The most coherent trend is observed for chemical hardness. It is demonstrated that, in general, larger molecules are chemically softer provided they belong to the same chemical type. The electronegativity is reduced by methyl and mercapto substituents and increased by phenyl substituent. It is further shown that phenyl substituent reduces the solvation free energy thus increasing the relative tendency of the molecule to get adsorbed on the surface, which may contribute to the increased inhibition effectiveness against corrosion of copper.

  16. 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. PMID:27515320

  17. A new ternary copper(II) complex derived from 2-(2";-pyridyl)benzimidazole and glycylglycine: Synthesis, characterization, DNA binding and cleavage, antioxidation and HSA interaction

    Science.gov (United States)

    Fu, Xia-Bing; Lin, Zi-Hua; Liu, Hai-Feng; Le, Xue-Yi

    2014-03-01

    A new ternary copper(II)-dipeptide complex [Cu(glygly)(HPB)(Cl)]ṡ2H2O (glygly = glycylglycine anion, HPB = 2-(2";-pyridyl)benzimidazole) has been synthesized and characterized. The DNA interaction of the complex was studied by spectroscopic methods, viscosity, and electrophoresis measurements. The antioxidant activity was also investigated using the pyrogallol autoxidation assay. Besides, the interaction of the complex with human serum albumin (HSA) in vitro was examined by multispectroscopic techniques. The complex partially intercalated to CT-DNA with a high binding constant (Kb = 7.28 × 105 M-1), and cleaved pBR322 DNA efficiently via an oxidative mechanism in the presence of Vc, with the HO· and O2-rad as the active species, and the SOD as a promoter. Furthermore, the complex shows a considerable SOD-like activity with the IC50 value of 3.8386 μM. The complex exhibits desired binding affinity to HSA, in which hydrogen bond or vander Waals force played a major role. The alterations of HSA secondary structure induced by the complex were confirmed by UV-visible, CD, synchronous fluorescence and 3D fluorescence spectroscopy.

  18. Performance degradation studies on an poly 2,5-benzimidazole high-temperature proton exchange membrane fuel cell using an accelerated degradation technique

    Science.gov (United States)

    Jung, Guo-Bin; Chen, Hsin-Hung; Yan, Wei-Mon

    2014-02-01

    In this work, the performance degradation of a poly 2,5-benzimidazole (ABPBI) based high-temperature proton exchange membrane fuel cell (HT-PEMFC) was examined using an accelerated degradation technique (ADT). Experiments using an ADT with 30 min intervals were performed by applying 1.5 V to a membrane electrode assembly (MEA) with hydrogen and nitrogen feeding to the anode and cathode, respectively, to simulate the high voltage generated during fuel cell shutdown and restart. The characterization of the MEAs was performed using in-situ and ex-situ electrochemical methods, such as polarization curves, AC impedance, and cyclic voltammetry (CV), and TEM imaging before and after the ADT experiments. The measured results demonstrated that the ADT testing could be used to dramatically reduce the duration of the degradation. The current output at 0.4 V decreased by 48% after performing ADT testing for 30 min. From the AC impedance, CV and RTGA measurements, the decline in cell performance was found to be primarily due to corrosion and thinning of the catalyst layer (or carbon support) during the first 30 min, leading to the dissolution and agglomeration of the platinum catalyst.

  19. Synthesis,Structure and Luminescence of Two Coordination Polymers Based on 1,4-Benzenedicarboxylate and 2-(3-Pyridyl)benzimidazole Ligands

    Institute of Scientific and Technical Information of China (English)

    LI wei; LI Ming-Xing; HE Xiang; SHAO Min; AN Bao-Li

    2008-01-01

    Hydrothermal reactions of Cd(Ⅱ)/Zn(Ⅱ)nitrates with 1,4-benzenedicarboxylic acid(H2Bdc)and 2-(3-pyridyl)-benzimidazole(3-PyHBIm)afforded complexes {[Cd(3-PyHBlm)(Bdc)(H2O)2](H2Bdc)1/2]n(1)and [Zn(3-PyHBIm)2-(Bdc)(H2O)2]n(2).X-ray structural analysis reveals that both complexes are ID coordination polymers.In complex 1,3-PyHBIm coordinates to Cd(Ⅱ)unidentately via a pyridyl N-donor.Bdc2-anion acts as a tetradentate ligand and coordinates to Cd(Ⅱ)to form a zigzag chain where two H2O coordinate in cis-fashion.H2Bdc guest molecule is involved in the hydrogen-bonding network,which leads to a 3D supramolecular architecture.In complex 2,Bdc2-acts as a bidentate ligand and coordinates to Zn(Ⅱ)to form a linear infinite chain where two H2O molecules coordi-nate in trans-fashion.The complexes are thermally stable and exhibit luminescence in the solid state.

  20. Synthesis and properties of novel multiblock copolyimides consisting of benzimidazole-groups-containing sulfonated polyimide hydrophilic blocks and non-sulfonated polyimide hydrophobic blocks as proton exchange membranes

    International Nuclear Information System (INIS)

    A series of novel multiblock copolymers consisting of benzimidazole-groups-containing sulfonated polyimide hydrophilic blocks (averaged block length = 20) and non-sulfonated polyimide hydrophobic blocks (averaged block length = 5 or 10) have been synthesized via two-pot synthetic procedures. The anhydride-terminated hydrophilic oligomer is synthesized by copolymerization of excess 1,4,5,8-naphthalelnetetracarboxylic dianhydride (NTDA) with amine-terminated polybenzimidazole (PBI-NH2) and 4,4′-bis(4-aminophenoxy) biphenyl-3,3′-disulfonic acid (BAPBDS), while the amine-terminated hydrophobic oligomers are synthesized by polymerization of excess non-sulfonated diamines with NTDA or a fluorinated dianhydride. The resulting multiblock copolymers can be cast into tough membranes indicating that reasonably high molecular weights block copolymers have been obtained. The block SPIs exhibit microphase-separated structure, whereas the random one is amorphous. Fenton’s test reveals that the block copolymer membranes, in particular, those consisting of fluorinated hydrophobic blocks, are fairly stable toward radical oxidation. Preliminary fuel cell tests are performed to evaluate the fuel cell performance of the block copolymer membranes. The single cell equipped with the block copolymer membrane of which hydrophobic block is prepared from NTDA and a fluorinated diamine (averaged block length = 5) exhibits a peak output power density of 0.70 W/cm2 at 90 °C and 92% relative humidity for H2/air which is comparable to that of Nafion 112

  1. Fac-mer equilibria of coordinated iminodiacetate (ida2-) in ternary CuII(ida)(H-1B)- complex formation (B = imidazole, benzimidazole) in aqueous solution

    Indian Academy of Sciences (India)

    Susmita Bandyopadhyay; G N Mukherjee

    2003-08-01

    pH potentiometric and spectrophotometric investigations on the complex formation equilibria of CuII with iminodiacetate (ida2-) and heterocyclic N-bases, viz. imidazole and benzimidazole (B), in aqueous solution in binary and ternary systems using different molar ratios of the reactants indicated the formation of complexes of the types, Cu(ida), Cu(ida)(OH)-, (ida)Cu(OH)Cu(ida)-, Cu(B)2+, Cu(H-1B)+, Cu(ida)(H-1B)-, (ida)Cu(B)Cu(ida) and (ida)Cu(H-1B)Cu(ida)-. Formation constants of the complexes at 25 ± 1° at a fixed ionic strength, = 0.1 mol dm-3 (NaNO3) in aqueous solution were evaluated and the complex formation equilibria were elucidated with the aid of speciation curves. Departure of the experimental values of the reproportionation constants (log Cu) of ternary Cu(ida)(H-1B)- complexes from the statistically expected values, despite their formation in appreciable amounts at equilibrium, were assigned to fac(f)-mer(m) equilibria of the ida2- ligand coordinated to CuII, as the N-heterocyclic donors, (H-1B)-, coordinate trans- to the N-(ida2-) atom in the binary Cu(ida) complex to form the ternary Cu(ida) (H-1B)- complexes.

  2. Proteomic and ultrastructural analysis of the effect of a new nitazoxanide-N-methyl-1H-benzimidazole hybrid against Giardia intestinalis.

    Science.gov (United States)

    Matadamas-Martínez, Félix; Castillo, Rafael; Hernández-Campos, Alicia; Méndez-Cuesta, Carlos; de Souza, Wanderley; Gadelha, Ana Paula; Nogueda-Torres, Benjamín; Hernández, José Manuel; Yépez-Mulia, Lilián

    2016-04-01

    In an effort to develop alternative drugs for the treatment of giardiasis our research group has synthesized and evaluated a novel nitazoxanide and N-methyl-1H-benzimidazole hybrid molecule, named CMC-20. It showed an IC50 of 0.010μM on Giardia intestinalis, lower than the IC50 values of 0.015, 0.037 and 1.224μM for nitazoxanide, albendazole and metronidazole, respectively. In addition, we report studies carried out on its mechanism of action and effect at the ultrastructural level on G. intestinalis. The proteomic analysis of trophozoites treated with CMC-20 revealed significant changes in the expression level of proteins of the cytoskeleton, alpha and beta tubulin, alpha-1, beta giardin and axoneme-associated protein, among other molecules. Ultrastructural studies demonstrated that CMC-20 induces morphological changes on the parasite that loses its characteristic pear shape. Uncommon large bulbous structure at the flagella end, and parasites showing flange membrane bending and a concave depression in the ventral region, resembling an encystation process, were also observed. In addition, some apoptotic and autophagic-like features, such as membrane blebbing, intense vacuolation, chromatin condensation and multilamellar bodies were detected. Phosphatidylserine externalization was determined as an apoptotic marker by flow cytometry and immunofluorescence microscopy; however, a typical ladder-like DNA fragmentation profile was not detected. Although it was found that CMC-20 triggers the encystation process, damage to the cyst wall indicates loss of viability. PMID:27033928

  3. Impact of the different electron-releasing subunits on the dye-sensitized solar cell performance of new triphenylamine-benzimidazole based molecules.

    Science.gov (United States)

    Dinçalp, Haluk; Saltan, Gözde Murat; Aykut, Deniz; Zafer, Ceylan

    2015-10-01

    New triphenylamine-benzimidazole type small molecules with different electron-releasing groups were designed and synthesized to investigate their photovoltaic performances in dye sensitized solar cells (DSSCs). Their good visible absorptions covering the 400-535 nm in addition to suitable lowest unoccupied molecular orbital (LUMO) energy levels between -3.03 and -3.11 eV make good candidates them for DSSC devices. Fluorescence quenching studies of the dyes with pristine titania support the good electron injection to conduction band of TiO2. Time resolved measurements of the dyes in solutions indicate the occurence of charge generation during the excited state. One of the used dyes in DSSC devices, TPA5a, carrying a methoxy group in triphenylamine part of the structure, gave much higher power conversion efficiency (PCE) value of 4.31% as compared to the other derivatives. Device fabricated from TPA5a dye gives good external quantum efficiency (EQE) value above 70% at 460 nm. Also, electron impedance spectroscopy (EIS) analysis of the devices gives a good explanation of the understanding of the cell performances. PMID:25956328

  4. A Mixed-valent Hexanuclear CuⅡ-CuⅠ Complex with Unusual Tridentate pbi Ligand (pbi= 2-(2-Pyridyl)-benzimidazole)

    Institute of Scientific and Technical Information of China (English)

    LIU Jiu-Hui; WU Xiao-Yuan; ZHANG Quan-Zheng; HE Xiang; LU Can-Zhong

    2006-01-01

    A mixed-valent hexanuclear complex [CuⅡCuⅠ2(pbi)2Br2]2 (pbi = (2-(2-pyridyl)-benzimidazole) exhibiting a dimeric unit bridged by two Br atoms was synthesized by hydrothermal reaction.Interestingly, there exist intramolecular and intermolecular π-πstacking interactions as well as metalaromatic ring interactions in the title complex. The crystal belongs to the monoclinic system, space group P-1, with a = 7.1061(9), b = 12.1008(13), c = 14.0711(17) (A), α = 91.742(8), β = 100.155(9), γ =90.486(7)°, V = 1190.3(2)(A)3, Z = 2, C48H32Br4Cu6N12, Mr = 1477.74, Dc= 2.061 g/cm3, F(000) = 718,μ(MoKα) = 6.039 mm-1, the final R = 0.0481 and wR = 0.0974 for 3426 observed reflections (I>2σ(I)).

  5. Crystal structure of bis[2-(1H-benzimidazol-2-yl-4-bromophenolato-κ2N3,O]cobalt(II

    Directory of Open Access Journals (Sweden)

    Yan Fan

    2014-11-01

    Full Text Available The asymmetric unit of the title CoII complex, [Co(C13H8BrN2O2], contains two independent molecules (A and B. In both molecules, the CoII cation is N,O-chelated by two 2-(1H-benzimidazol-2-yl-4-bromophenolate anions in a distorted tetrahedral geometry. In molecule A, both chelating rings display an envelope conformation, with the flap Co atom lying 0.614 (6 and 0.483 (6 Å from the mean planes of the remaining atoms. In molecule B, both chelating rings are approximately planar, the maximum deviations being 0.039 (4 and 0.076 (3 Å. In the crystal, molecules are linked by classical N—H...O hydrogen bonds and weak C—H...O and C—H...Br hydrogen bonds into a three-dimensional supramolecular network. Extensive π–π stacking is observed between nearly parallel aromatic rings of adjacent molecules with centroid–centroid distances in the range 3.407 (3–3.850 (4 Å.

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

    Science.gov (United States)

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

    2012-05-24

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

  7. Design, synthesis and molecular modeling studies of few chalcone analogues of benzimidazole for epidermal growth factor receptor inhibitor in search of useful anticancer agent.

    Science.gov (United States)

    Chhajed, Santosh S; Sonawane, Sandeep S; Upasani, Chandrashekhar D; Kshirsagar, Sanjay J; Gupta, Pramodkumar P

    2016-04-01

    In the present investigation, few 3-(substitutedphenyl)-1-[2-(1-hydroxy-ethyl)]-1H-benzimidazol-1-yl)prop-2-en-1-ones are EGFR antagonist are designed, by molecular docking analysis. The synthesized compounds were tested for their in vitro anticancer activity by propidium iodide fluorescent assay and Trypan blue viability assay against colorectal cancer cell lines (HCT116) and non-small cell lung cancer cell lines (H460). Human Epithelial Kidney cell lines (HEK) are used as normal cell lines for studying effect of drug on non-cancerous cells within human body. Evaluation of cytotoxic studies of synthesized compounds CHL(1-8) reveal that compound CHL1 [IC50=7.31 and 10.16 μM against HCT116 and H460 cell lines respectively, by PI assay] and CHL8 [IC50=12.52 and 6.83 against HCT116 and H460μM cell lines respectively] possess promising cytotoxic activity. PMID:26878127

  8. Discovery, SAR, and Radiolabeling of Halogenated Benzimidazole Carboxamide Antagonists as Useful Tools for (alpha)4(beta)1 Integrin Expressed on T- and B-cell Lymphomas

    Energy Technology Data Exchange (ETDEWEB)

    Carpenter, R D; Natarajan, A; Lau, E Y; Andrei, M; Solano, D M; Lightstone, F C; DeNardo, S J; Lam, K S; Kurth, M J

    2010-02-08

    The cell surface receptor {alpha}{sub 4}{beta}{sub 1} integrin is an attractive yet poorly understood target for selective diagnosis and treatment of T- and B-cell lymphomas. This report focuses on the rapid microwave preparation of medicinally pertinent benzimidazole heterocycles, structure-activity relationships (SAR) of novel halobenzimidazole carboxamide antagonists 3-6, and preliminary biological evaluation of radioiodinated agents 7, 8, and 18. The I-125 derivative 18 had good tumor uptake (12 {+-} 1% ID/g at 24 h; 4.5 {+-} 1% ID/g at 48 h) and tumor:kidney ratio ({approx}4:1 at 24 h; 2.5:1 at 48 h) in xenograft murine models of B-cell lymphoma. Molecular homology models of {alpha}{sub 4}{beta}{sub 1} integrin have predicted that docked halobenzimidazole carboxamides have the halogen atom in a suitable orientation for halogen-hydrogen bonding. These high affinity ({approx} pM binding) halogenated ligands are attractive tools for medicinal and biological use; the fluoro and iodo derivatives are potential radiodiagnostic ({sup 18}F) or radiotherapeutic ({sup 131}I) agents, whereas the chloro and bromo analogues could provide structural insight into integrin-ligand interactions through photoaffinity cross-linking/mass spectroscopy experiments, as well as co-crystallization X-ray studies.

  9. Imported bancroftian filariasis: diethylcarbamazine response and benzimidazole susceptibility of Wuchereria bancrofti in dynamic cross-border migrant population targeted by the National Program to Eliminate Lymphatic Filariasis in South Thailand.

    Science.gov (United States)

    Bhumiratana, A; Pechgit, P; Koyadun, S; Siriaut, C; Yongyuth, P

    2010-02-01

    The implementation on the Thailand-Myanmar border of annual mass drug administration (MDA) of a single 6 mg/kg dose of diethylcarbamazine (DEC) plus 400mg albendazole, part of the National Program to Eliminate Lymphatic Filariasis (PELF), has been challenging. In particular, chain migration of cross-border Myanmar workers at risk for nocturnally periodic Wuchereria bancrofti infection can lead to imported bancroftian filariasis (IBF) in Thailand. IBF is targeted for multiple-dose MDA with 300 mg DEC, in addition to what is recommended by the World Health Organization (WHO). The dynamic Myanmar migrants in Phang-nga, southern Thailand were sampled to test whether the responsible W. bancrofti has a genetic predisposition of benzimidazole exposure, and IBF exhibits DEC susceptibility. The long-term migrants had more access to DEC. IBF in W. bancrofti antigenemic (microfilaremic vs. amicrofilaremic) short-term migrants exhibited susceptibility to a 300-mg single-dose DEC treatment. During the course of a 3-month follow-up, antigenemia was significantly reduced, but microfilaremia was fluctuated. Surprisingly, a newly recognized Mansonella infection co-existing among W. bancrofti-affected Myanmar migrants elicited microfilaremia clearance within a month after treatment. As a result of the presence of genetically stable W. bancrofti beta-tubulin (Wbtubb) gene responsible for benzimidazole susceptibility, IBF did not possess a genetic predisposition for benzimidazole exposure. Point mutations at positions Phe167Tyr and Phe200Tyr were not detected by Wbtubb locus-specific nested PCR and sequencing. This study has the potential to help guide not only the Thai/Myanmar PELF surveillance and monitoring of mass treatment impacts on W. bancrofti, but also the other endemic countries allied with the Global Program to Eliminate Lymphatic Filariasis (GPELF). PMID:19835831

  10. {2-[6-(1H-Benzimidazol-2-yl-κN3-2-pyridyl-κN]benzimidazolato-κN}(dicyanamido-κN(methanol-κOcopper(II

    Directory of Open Access Journals (Sweden)

    Chi Zhang

    2011-01-01

    Full Text Available In the title compound, [Cu(C19H12N5(C2N3(CH3OH], the CuII atom is coordinated by three N atoms from an anionic 2,6-bis(1H-benzimidazol-2-ylpyridine (bbp ligand, an O atom from a methanol molecule and one N atom from a dicyanamide anion. The crystal structure is stabilized by O—H...N and N—H...N hydrogen bonds, forming a three-dimensional network.

  11. Aqua(1H-benzimidazole-κN3(pyridine-2,6-dicarboxylato-κ3O2,N,O6copper(II 0.75-hydrate

    Directory of Open Access Journals (Sweden)

    Gui-Ying Dong

    2010-05-01

    Full Text Available The title complex, [Cu(C7H3NO4(C7H6N2(H2O]·0.75H2O, consists of discrete monomeric units. The CuII atom is coordinated by two carboxylate O atoms and the N atom from a dipicolinate unit and by an N atom from a benzimidazole ligand. The distorted square-pyramidal geometry is completed by a longer axial bond to the O atom of a water molecule. The molecular structure and packing are stabilized by classical O—H...O and N—H...O hydrogen bonds, also including a disordered crystal water molecule.

  12. Bis[2-(2-amino­eth­yl)-1H-benzimidazole-κ2 N 2,N 3](nitrato-κ2 O,O′)cobalt(II) chloride trihydrate

    OpenAIRE

    Jing Zhao; Heng Zhang; Guoyi Zhu

    2012-01-01

    In the title compound, [Co(NO3)(C9H11N3)2]Cl·3H2O, the CoII atom is coordinated by four N atoms from two chelating 2-(2-aminoethyl)-1H-benzimidazole ligands and two O atoms from one nitrate anion in a distorted octahedral coordination environment. In the crystal, N—H...Cl, N—H...O, O—H...Cl and O—H...O hydrogen bonds link the complex cations, chloride anions and solvent water molecules into a three-dimensional network. π–&...

  13. Phenotypic and genotypic characterisation of Haemonchus spp. and other gastrointestinal nematodes resistant to benzimidazole in infected calves from the tropical regions of Campeche State, Mexico.

    Science.gov (United States)

    Encalada-Mena, Lisandro; Tuyub-Solis, Henry; Ramirez-Vargas, Gabriel; Mendoza-de-Gives, Pedro; Aguilar-Marcelino, Liliana; López-Arellano, Ma Eugenia

    2014-09-15

    The aim of this study was to identify the presence of anthelmintic resistance to benzimidazole (BZ) in gastrointestinal nematodes (GIN) from naturally infected calves in the tropical regions of Campeche State of Mexico. The faecal egg count reduction test (FECRT) was conducted at 10 livestock farms localised in the Carmen, Candelaria, Champotón, Escárcega and Palizada municipalities of Campeche. The assessed anthelmintic was albendazole. The trial period was between August and November 2012. Infected calves were allocated into two groups, control and treated, on each farm. The number of eggs excreted per g of faeces was estimated by the McMaster technique at 0 and 14 days pre- and post- treatment, respectively. Recovered infective larvae (L3) (pre- and post-treatment) were identified using taxonomic keys and a genomic DNA (gDNA) template from a pool of L3 species prior to BZ treatment. Additionally, BZ-resistance polymorphisms in Haemonchus were determined by Allele Specific PCR (AS-PCR) at codon 200 and by end-point PCR at codons 200, 198 and 167 from isotype 1 of the β-tubulin gene. Morphological identification revealed Haemonchus, Cooperia, Trichostrongylus, Ostertagia and Oesophagostumum L3 species before BZ treatment, and Haemonchus and Cooperia L3 species after treatment. Additionally, of the GIN populations, three exhibited BZ resistance, and seven were BZ-susceptible by FECRT. Molecular analysis identified mutations in Haemonchus populations on nine farms at codon 200 (TTC to TAC) by AS-PCR, while no changes were observed at 167 (TTC to TAC) or 198 (GAA to GCA) codons in any population. In conclusion, resistance to BZ was determined in Haemonchus and Cooperia nematodes in infected cattle in five tropical regions of Campeche State.

  14. A novel biosensing mechanism based on a poly(N-butyl benzimidazole)-modified gold electrode for the detection of hydrogen peroxide

    Energy Technology Data Exchange (ETDEWEB)

    Hua, Mu-Yi, E-mail: huamy@mail.cgu.edu.tw [Green Technology Research Center, Department of Chemical and Materials Engineering, Chang Gung University, Tao-Yuan 33302, Taiwan (China); Biosensor Group, Biomedical Engineering Research Center, Chang Gung University, Tao-Yuan 33302, Taiwan (China); Chen, Hsiao-Chien [Green Technology Research Center, Department of Chemical and Materials Engineering, Chang Gung University, Tao-Yuan 33302, Taiwan (China); Biosensor Group, Biomedical Engineering Research Center, Chang Gung University, Tao-Yuan 33302, Taiwan (China); Tsai, Rung-Ywan [Electronics and Optoelectronics Research Laboratories, Industrial Technology Research Institute, Hsinchu 31040, Taiwan (China); Lin, Yu-Chen [Green Technology Research Center, Department of Chemical and Materials Engineering, Chang Gung University, Tao-Yuan 33302, Taiwan (China); Biosensor Group, Biomedical Engineering Research Center, Chang Gung University, Tao-Yuan 33302, Taiwan (China); Wang, Leeyih [Center for Condensed Matter Science, Institute of Polymer Science and Technology, National Taiwan University, Taipei 10617, Taiwan (China)

    2011-05-05

    A novel mechanism to detect hydrogen peroxide (H{sub 2}O{sub 2}) using a poly(N-butyl benzimidazole) (PBBI)-modified gold (PBBI/Au) electrode is proposed. Synthetic PBBI was oxidized using a mixture of acetic acid (AcOH) and H{sub 2}O{sub 2} to form PBBI N-oxide (PBBINO). The structure of PBBINO was verified by Fourier transform infrared spectroscopy (FT-IR) and the degree of oxidation was measured by X-ray photoelectron spectroscopy (XPS). Moreover, the oxide could be reduced electrochemically back to PBBI. Based on this reaction, a novel enzyme-free PBBI/Au electrode was developed to detect H{sub 2}O{sub 2} in the presence of AcOH electrochemically. The biosensor detected H{sub 2}O{sub 2} linearly over concentrations ranging from 25 {mu}M to 10 mM with a detection limit of 6.25 {mu}M in phosphate buffer solution (PBS) mixed with AcOH at pH 6.4. In addition, at an applied potential of -0.5 V, the sensor characteristics could be tuned using AcOH over a pH range of 3.7-6.4. The sensitivity of the probe could be enhanced from 35.1 to 419.4 {mu}A mM{sup -1} cm{sup -2} by modifying the surface morphology of the PBBI/Au electrode from a smooth plane to a granular, three-dimensional configuration. Furthermore, it was not influenced by interfering compounds and showed high thermal stability.

  15. Cadmium(II) and cobalt(II) complexes generated from benzimidazole-5-carboxylate: Self-assembly by hydrogen bonding and π-π interactions

    International Nuclear Information System (INIS)

    Self-assembly of L- (HL=benzimidazole-5-carboxylic acid) with Cd(II) and Co(II), respectively, by layer-separating diffusion method at ambient temperature gives rise to two new supramolecular architectures [(CdL2.H2O).2CH3OH]n (1) and {[CoL2(H2O)2].2H2O}n (2), both of which are stabilized by the hydrogen bonding interactions and the intermolecular π-π interactions. 1 crystallizes in the triclinic system, space group P-1, with cell parameters M=516.78, a=9.084(2)A, b=10.063(10)A, c=11.533(8)A, α=90.21(11)o, β=99.48(6)o, γ=98.34(9)o, V=1028.4(12)A3, Z=2, R1[I>2σ(I)]=0.0257, wR2[I>2σ(I)]=0.0719. 2 crystallizes in the monoclinic system, space group C2/c, with cell parameters M=453.27, a=16.119(2)A, b=8.8952(13)A, c=14.195(2)A, β=118.507(2)o, V=1788.5(4)A3, Z=4, R1[I>2σ(I)]=0.0802, wR2[I>2σ(I)]=0.1515. Complex 1 displays a remarkable three-dimensional (3-D) structure with unusual channels generated from the interlayer voids. Complex 2 exhibits the 3-D structure consisting of 1-D zigzag chains. The thermal and fluorescence properties associated with their crystal structures have been measured, and complex 1 displays intense blue emission in the solid state

  16. Effect of acid-catalyzed formation rates of benzimidazole-linked polymers on porosity and selective CO2 capture from gas mixtures.

    Science.gov (United States)

    Altarawneh, Suha; İslamoğlu, Timur; Sekizkardes, Ali Kemal; El-Kaderi, Hani M

    2015-04-01

    Benzimidazole-linked polymers (BILPs) are emerging candidates for gas storage and separation applications; however, their current synthetic methods offer limited control over textural properties which are vital for their multifaceted use. In this study, we investigate the impact of acid-catalyzed formation rates of the imidazole units on the porosity levels of BILPs and subsequent effects on CO2 and CH4 binding affinities and selective uptake of CO2 over CH4 and N2. Treatment of 3,3'-Diaminobenzidine tetrahydrochloride hydrate with 1,2,4,5-tetrakis(4-formylphenyl)benzene and 1,3,5-(4-formylphenyl)-benzene in anhydrous DMF afforded porous BILP-15 (448 m(2) g(-1)) and BILP-16 (435 m(2) g(-1)), respectively. Alternatively, the same polymers were prepared from the neutral 3,3'-Diaminobenzidine and catalytic amounts of aqueous HCl. The resulting polymers denoted BILP-15(AC) and BILP-16(AC) exhibited optimal surface areas; 862 m(2) g(-1) and 643 m(2) g(-1), respectively, only when 2 equiv of HCl (0.22 M) was used. In contrast, the CO2 binding affinity (Qst) dropped from 33.0 to 28.9 kJ mol(-1) for BILP-15 and from 32.0 to 31.6 kJ mol(-1) for BILP-16. According to initial slope calculations at 273 K/298 K, a notable change in CO2/N2 selectivity was observed for BILP-15(AC) (61/50) compared to BILP-15 (83/63). Similarly, ideal adsorbed solution theory (IAST) calculations also show the higher specific surface area of BILP-15(AC) and BILP-16(AC) compromises their CO2/N2 selectivity.

  17. Experimental infection of Haemonchus contortus strains resistant and susceptible to benzimidazoles and the effect on mast cells distribution in the stomach of Mongolian gerbils (Meriones unguiculatus).

    Science.gov (United States)

    Königová, Alzbeta; Hrckova, Gabriela; Velebný, Samuel; Corba, Július; Várady, Marián

    2008-03-01

    Establishment rate of Haemonchus contortus in non-suppressed and immunosuppressed gerbils within 14 days post-infection was compared after inoculation with 1,000 third-stage larvae (L3), exsheathed BZ-susceptible larvae. Based on significantly higher number of larvae in gerbils receiving low doses of immunosuppressant agent hydrocortisone, development of benzimidazole (BZ)-susceptible and BZ-resistant strain of nematode in the stomach was studied on days 4, 7, 10, and 14 p.i. Sections of stomach from both groups of animals were examined for overall histopathological response and dynamics of mucosal mast cells (MMC) and connective tissue mast cells (CTMC). In the immunosuppressed gerbils, H. contortus L3 stage larvae developed to the L4 stage on days 10 and 14 p.i., and their sex ratio was higher toward female worms. Significantly higher ratios of establishment rate were recorded for BZ-susceptible than BZ-resistant strain. Infection elicited strong inflammation mainly in the lamina propria mucosae, where MMC numbers peaked on day 7 p.i., being present in a significantly higher numbers in gerbils infected with BZ-susceptible strain. Infection with BZ-susceptible strain of nematode also resulted in a higher number of CTMC in comparison with the effect of BZ-resistant strain, which were observed in the tela submucosa only. Thus, H. contortus infection in gerbils seems to be a suitable model to study host-parasite interactions. Our results indicate that BZ-resistant strain of H. contortus have a decreased capacity to establish infection in direct relation with lower mucosal and connective tissue MCs counts in the stomach.

  18. A Combination of 3D-QSAR, Molecular Docking and Molecular Dynamics Simulation Studies of Benzimidazole-Quinolinone Derivatives as iNOS Inhibitors

    Directory of Open Access Journals (Sweden)

    Peixun Liu

    2012-09-01

    Full Text Available Inducible Nitric Oxide Synthase (iNOS has been involved in a variety of diseases, and thus it is interesting to discover and optimize new iNOS inhibitors. In previous studies, a series of benzimidazole-quinolinone derivatives with high inhibitory activity against human iNOS were discovered. In this work, three-dimensional quantitative structure-activity relationships (3D-QSAR, molecular docking and molecular dynamics (MD simulation approaches were applied to investigate the functionalities of active molecular interaction between these active ligands and iNOS. A QSAR model with R2 of 0.9356, Q2 of 0.8373 and Pearson-R value of 0.9406 was constructed, which presents a good predictive ability in both internal and external validation. Furthermore, a combined analysis incorporating the obtained model and the MD results indicates: (1 compounds with the proper-size hydrophobic substituents at position 3 in ring-C (R3 substituent, hydrophilic substituents near the X6 of ring-D and hydrophilic or H-bond acceptor groups at position 2 in ring-B show enhanced biological activities; (2 Met368, Trp366, Gly365, Tyr367, Phe363, Pro344, Gln257, Val346, Asn364, Met349, Thr370, Glu371 and Tyr485 are key amino acids in the active pocket, and activities of iNOS inhibitors are consistent with their capability to alter the position of these important residues, especially Glu371 and Thr370. The results provide a set of useful guidelines for the rational design of novel iNOS inhibitors.

  19. The emergence of resistance to the benzimidazole anthlemintics in parasitic nematodes of livestock is characterised by multiple independent hard and soft selective sweeps.

    Directory of Open Access Journals (Sweden)

    Elizabeth Redman

    2015-02-01

    Full Text Available Anthelmintic resistance is a major problem for the control of parasitic nematodes of livestock and of growing concern for human parasite control. However, there is little understanding of how resistance arises and spreads or of the "genetic signature" of selection for this group of important pathogens. We have investigated these questions in the system for which anthelmintic resistance is most advanced; benzimidazole resistance in the sheep parasites Haemonchus contortus and Teladorsagia circumcincta. Population genetic analysis with neutral microsatellite markers reveals that T. circumcincta has higher genetic diversity but lower genetic differentiation between farms than H. contortus in the UK. We propose that this is due to epidemiological differences between the two parasites resulting in greater seasonal bottlenecking of H. contortus. There is a remarkably high level of resistance haplotype diversity in both parasites compared with drug resistance studies in other eukaryotic systems. Our analysis suggests a minimum of four independent origins of resistance mutations on just seven farms for H. contortus, and even more for T. circumincta. Both hard and soft selective sweeps have occurred with striking differences between individual farms. The sweeps are generally softer for T. circumcincta than H. contortus, consistent with its higher level of genetic diversity and consequent greater availability of new mutations. We propose a model in which multiple independent resistance mutations recurrently arise and spread by migration to explain the widespread occurrence of resistance in these parasites. Finally, in spite of the complex haplotypic diversity, we show that selection can be detected at the target locus using simple measures of genetic diversity and departures from neutrality. This work has important implications for the application of genome-wide approaches to identify new anthelmintic resistance loci and the likelihood of anthelmintic

  20. [Synthesis of stable solvates of monosodium 2-[R*s,9S*)-(4-methoxy-6,7,8, 9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)sulfinyl]-1H-benzimidazole].

    Science.gov (United States)

    Yamada, S; Goto, T; Yuasa, S; Yamaguchi, T; Kogi, K

    1996-08-01

    Monosodium 2-[(R*s,9S*)-(4-methoxy-6,7,8, 9-tetrahydro-5H-cyclohepta-[b]pyridin-9-yl)sulfinyl]-1H-benzimidazole (3A), a novel antiulcer agent previously reported by us, was found to be easily decomposed in weakly acidic solutions. In order to improve the stability of the parent compound, 3A, the preparation of 1-substituted benzimidazoles (4A) was attempted. However, the inhibitory effect of 4A against gastric acid secretion was less potent than that of 3A. Then 3A was solvated by EtOH or H2O to afford 5A or 6A, respectively. On the other hand, an another diastereoisomer, (R*s,9R*)-3B, was not solvated by EtOH or H2O under the same conditions. The thus obtained solvates (5A, 6A) are much more stable than that of 3A. The antiulcer activities of 5A and 6A were found to be similar to that of the parent compound (3A). Consequently, 6A was selected as an antiulcer agent for the development.

  1. 苯并咪唑类缓蚀剂缓蚀机理以及研究趋势%Corrosion-inhibiting mechanism and research tendency of the benzimidazole corrosion inhibitor

    Institute of Scientific and Technical Information of China (English)

    王娴

    2012-01-01

    Benzimidazole corrosion inhibitor was a kind of hydrochloride pickling inhibitor. It was possessed various inhibition efficiency because of the distinction of substitutional group. It was occupied the characteristics of high performance,low mammalian toxicity and biodegradation. It also was a kind of adsorption corrosion inhibitor, it also was involved many aspects of resistance chemical corrosion, molecular interface adsorption, the groups covering effects as well as hydrogen-bonding association effects. It was analysised and introduced the preparation method, corrosion-inhibiting mechanism and research tendency of the benzimidazole corrosion inhibitor in this article.%苯并咪唑类缓蚀剂是一类盐酸酸洗缓蚀剂,当取代基不同,其分子呈现不同的缓蚀效率。苯并咪唑类缓蚀剂具有高效、低毒和生物易降解等特点。苯并咪唑缓蚀剂是吸附型缓蚀剂,它涉及到阻化效应、分子界面吸附、基团覆盖效应和氢键缔合效应等多方面。文中介绍了苯并咪唑类缓蚀剂的制备方式、缓释机理以及发展状况。

  2. Bis(μ-3-hydroxybenzoato-κ2O1:O3;κ2O3:O1-bis[bis(1H-benzimidazole-κN3(3-hydroxybenzoato-κOnickel(II] bis(1H-benzimidazole-κN3bis(3-hydroxybenzoato-κO1nickel(II hexahydrate

    Directory of Open Access Journals (Sweden)

    Duan-Jun Xu

    2008-02-01

    Full Text Available The title compound, [Ni2(C7H5O34(C7H6N24][Ni(C7H5O32(C7H6N22]·6H2O, is a mononuclear/dinuclear nickel(II cocrystal, the two molecular species interacting through hydrogen bonds that involve the uncoordinated water molecules. In the mononuclear species, the NiII ion, located on an inversion center, is coordinated by two 1H-benzimidazole (bzim ligands and two 3-hydroxybenzoate (hba anions in a square-planar geometry. In the centrosymmetric dinuclear species, the NiII ion is coordinated by two bzim ligands and three hba anions in a square-pyramidal geometry; of the two independent hba anions, one bridges two NiII ions with both carboxylate and hydroxyl groups whereas the other coordinates in a unidentate manner to the NiII ion. The apical Ni—Ohydroxyl bond is 0.39 Å longer than the basal Ni—Ocarboxyl bonds. The face-to-face separation of 3.326 (9 Å indicates the existence of π–π stacking between parallel bzim ligands of adjacent dinuclear entities. Extensive N—H...O and O—H...O hydrogen bonds help to stabilize the crystal structure.

  3. 苯并咪唑类化合物的合成及其抑菌活性%Synthesis and bacteriostatic activity of benzimidazole compounds

    Institute of Scientific and Technical Information of China (English)

    黄涛; 程康华; 颐晓利

    2013-01-01

    To find new organic wood preservative with broad-spectrum and hyperactivity, seven 5-substituted benzimidazole compounds were synthesized from 4-substituted o-phenylenediamine through multi-step reactions including acyla-tion, cyclization and so on. Their chemical structures were confirmed by melting points, MS, 1H NMR and elemental a-nalysis. The target compounds were screened for antimicrobial activity by agar-well diffusion method against white-rot fungi ( Coriolus verskolor), brown-rot fungi (Gloeophyllum trabeum) and moulds (Aspergillus niger and Trichoderma viride). The preliminary fungicidal tests showed that seven compounds had no fungicidal activities, but some of them had anti-mould activities. Compound 4a at concentration of 1. 0% showed strong anti-mould activity which was significantly higher than that of pentachlorophenate, and compounds 4b was equal to contrast.%为探索具有高活性的有机木材防腐剂,以4-取代邻苯二胺为原料,经酰化、环合等步骤合成了7种5-取代苯并咪唑类衍生物,并经熔点、MS、1H-NMR及元素分析确证其结构.用滤纸片法研究目标化合物对白腐菌(彩绒革盖菌(Coriolus versicolor))、褐腐菌(密粘褶菌(Gloeophyllum trabeum))、霉菌(黑曲霉(Aspergillus niger)和绿色木霉(Trichoderma viride))的抑制活性,结果表明:合成的7种化合物对木材中的腐朽菌均没有抑菌活性,但部分化合物对木材腐朽菌中的霉菌有明显的抑制效果;化合物4a在质量分数为1.0%时对两种霉菌就表现出较强的抑菌效果,且其效果明显优于对照试剂(五氯酚钠),化合物4b的抑菌效果则与对照试剂相当.

  4. A new three-dimensional zinc(II) coordination polymer involving 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole and benzene-1,4-dicarboxylate ligands.

    Science.gov (United States)

    Jian, Shou Jun; Han, Qian Qian; Yang, Huai Xia; Meng, Xiang Ru

    2016-07-01

    Metal-organic frameworks (MOFs) based on multidentate N-heterocyclic ligands involving imidazole, triazole, tetrazole, benzimidazole, benzotriazole or pyridine present intriguing molecular topologies and have potential applications in ion exchange, magnetism, gas sorption and storage, catalysis, optics and biomedicine. The 2-[(1H-1,2,4-triazol-1-yl)methyl]-1H-benzimidazole (tmb) ligand has four potential N-atom donors and can act in monodentate, chelating, bridging and tridentate coordination modes in the construction of complexes, and can also act as both a hydrogen-bond donor and acceptor. In addition, the tmb ligand can adopt different coordination conformations, resulting in complexes with helical structures due to the presence of the flexible methylene spacer. A new three-dimensional coordination polymer, poly[[bis(μ2-benzene-1,4-dicarboxylato)-κ(4)O(1),O(1'):O(4),O(4');κ(2)O(1):O(4)-bis{μ2-2-[(1H-1,2,4-triazol-1-yl)methyl-κN(4)]-1H-benzimidazole-κN(3)}dizinc(II)] trihydrate], {[Zn(C8H4O4)(C10H9N5)]·1.5H2O}n, has been synthesized by the reaction of ZnCl2 with tmb and benzene-1,4-dicarboxylic acid (H2bdic) under solvothermal conditions. There are two crystallographically distinct bdic(2-) ligands [bdic(2-)(A) and bdic(2-)(B)] in the structure which adopt different coordination modes. The Zn(II) ions are bridged by tmb ligands, leading to one-dimensional helical chains with different handedness, and adjacent helices are linked by bdic(2-)(A) ligands, forming a two-dimensional network structure. The two-dimensional layers are further connected by bdic(2-)(B) ligands, resulting in a three-dimensional framework with the topological notation 6(6). The IR spectra and thermogravimetric curves are consistent with the results of the X-ray crystal structure analysis and the title polymer exhibits good fluorescence in the solid state at room temperature. PMID:27377273

  5. 1,3,5-Tris(phenyl-2-benzimidazole)-benzene cathode buffer layer thickness dependence in solution-processable organic solar cell based on 1,4,8,11,15,18,22,25-octahexylphthalocyanine

    Science.gov (United States)

    De Roméo Banoukepa, Gilles; Fujii, Akihiko; Shimizu, Yo; Ozaki, Masanori

    2015-04-01

    Studies on the insertion effects of a cathode buffer layer on bulk heterojunction organic solar cell based on 1,4,8,11,15,18,22,25-octahexylphthalocyanine (C6PcH2) and 1-(3-methoxy-carbonyl)-propyl-1-1-phenyl-(6,6)C61 (PCBM) by using 1,3,5-tris(phenyl-2-benzimidazole)-benzene (TPBi) as a cathode buffer layer material have been carried out. The external quantum efficiency and the short-circuit current markedly increased, resulting in the enhancement of the power conversion efficiency. The solar cell performance has been discussed from the atomic force microscopy, photoelectron yield spectroscopy and X-ray photoelectron spectroscopy measurements.

  6. (Dimethylformamide-κO(2-hydroxybenzoato-κ2O1,O1′[tris(1-methyl-1H-benzimidazol-2-ylmethyl-κN3amine-κN]manganese(II perchlorate dimethylformamide monosolvate

    Directory of Open Access Journals (Sweden)

    Baoliang Qi

    2010-10-01

    Full Text Available In the title complex, [Mn(C7H5O3(C27H27N7(C3H7NO]ClO4·C3H7NO, the MnII ion is coordinated in a slightly distorted monocapped trigonal-prismatic geometry. The tris(1-methyl-1H-benzimidazol-2-ylmethylamine (Mentb ligand coordinates in a tetradentate mode and the coordination is completed by a bis-chelating salicylate ligand and a dimethylformamide ligand. The hydroxy group and the ortho H atoms of the salicylate ligand were refined as disordered over two sites with occupancies of 0.581 (8 and 0.419 (8. Both disorder components of the hydroxy group form intramolecular O—H...O hydrogen bonds.

  7. Seven organic salts assembled from hydrogen-bonds of N-H⋯O, O-H⋯O, and C-H⋯O between acidic compounds and bis(benzimidazole)

    Science.gov (United States)

    Jin, Shouwen; Liu, Hui; Gao, Xin Jun; Lin, Zhanghui; Chen, Guqing; Wang, Daqi

    2014-10-01

    Seven crystalline organic acid-base adducts derived from 1,4-bis(benzimidazol-2-yl)butane/1,2-bis(2-benzimidazolyl)-1,2-ethanediol and acidic components (picric acid, 2-hydroxy-5-(phenyldiazenyl)benzoic acid, 5-sulfosalicylic acid, oxalic acid, and 1,5-naphthalenedisulfonic acid) were prepared and characterized by the single crystal X-ray diffraction analysis, IR, mp, and elemental analysis. All of the seven compounds are organic salts involving proton transfer from the acidic components to the bis(benzimidazole). For the salt 3, although a competing carboxyl group is present, it has been observed that only the proton at the -SO3H group is deprotonized rather than the H at the COOH. While in the salt 7, both COOH and SO3H were ionized to exhibit a valence number of -2. For 4, the oxalic acid existed as unionized molecule, monoanion, and dianion simultaneously in one compound. All supramolecular architectures of the organic salts 1-7 involve extensive intermolecular N-H⋯O, O-H⋯O, and C-H⋯O hydrogen bonds as well as other noncovalent interactions. Since the potentially hydrogen bonding phenol group is present in the ortho position to the carboxyl group in 2, 3, and 7, it forms the more facile intramolecular O-H⋯O hydrogen bonding. The role of weak and strong noncovalent interactions in the crystal packing is ascertained. These weak interactions combined, all the complexes displayed 3D framework structure.

  8. A new one-dimensional Cd(II) coordination polymer with a two-dimensional layered structure incorporating 2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole and benzene-1,2-dicarboxylate ligands.

    Science.gov (United States)

    Huang, Qiu Ying; Lin, Xiao Yi; Meng, Xiang Ru

    2016-06-01

    The N-heterocyclic ligand 2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole (imb) has a rich variety of coordination modes and can lead to polymers with intriguing structures and interesting properties. In the coordination polymer catena-poly[[cadmium(II)-bis[μ-benzene-1,2-dicarboxylato-κ(4)O(1),O(1'):O(2),O(2')]-cadmium(II)-bis{μ-2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole}-κ(2)N(2):N(3);κ(2)N(3):N(2)] dimethylformamide disolvate], {[Cd(C8H4O4)(C11H10N4)]·C3H7NO}n, (I), each Cd(II) ion exhibits an irregular octahedral CdO4N2 coordination geometry and is coordinated by four O atoms from two symmetry-related benzene-1,2-dicarboxylate (1,2-bdic(2-)) ligands and two N atoms from two symmetry-related imb ligands. Two Cd(II) ions are connected by two benzene-1,2-dicarboxylate ligands to generate a binuclear [Cd2(1,2-bdic)2] unit. The binuclear units are further connected into a one-dimensional chain by pairs of bridging imb ligands. These one-dimensional chains are further connected through N-H...O hydrogen bonds and π-π interactions, leading to a two-dimensional layered structure. The dimethylformamide solvent molecules are organized in dimeric pairs via weak interactions. In addition, the title polymer exhibits good fluorescence properties in the solid state at room temperature. PMID:27256695

  9. Structural Requirements of Some 2-(1-Propylpiperidin-4-yl)-1H-benzimidazole-4-carboxamide Derivatives as Poly (ADP-Ribose) Polymerase (PARP) for the Treatment of Cancer: QSAR Approach.

    Science.gov (United States)

    Sharma, Mukesh C

    2016-03-01

    The present study is aimed to elucidate the structural features of substituted 2-(1-propylpiperidin-4-yl)-1H-benzimidazole-4-carboxamide required for poly (ADP-ribose) polymerase inhibition and to obtain predictive 2D QSAR models to guide the rational synthesis of novel poly (ADP-ribose) polymerase inhibitors. The statistical analysis has shown that excellent results are obtained by using partial least regression based on simulated annealing method. The best model was selected based on the highest correlation coefficient r (2) = 0.8590, and cross-validated squared correlation coefficient q (2) = 0.7875 with external predictive ability of [Formula: see text] was developed by stepwise PLS method with the descriptors like T_N_F_1, SdsCHcount, and Rotatable Bond Count. The generated models provide insight into the influence of various interactive fields on the activity and, thus, can help in designing and forecasting the inhibition activity of novel (ADP-ribose) polymerase molecules. PMID:26205198

  10. 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.

  11. Multiresidue screening method for detection of benzimidazoles and their metabolites in liver and muscle by high-performance liquid chromatography: method development and validation according to Commission Decision 2002/657/EC

    Directory of Open Access Journals (Sweden)

    Marilena Gili

    2014-02-01

    Full Text Available The use of veterinary drugs may cause the presence of residues in food of animal origin if appropriate withdrawal periods are not respected. A high-performance liquid chromatography (HPLC method has been developed for the simultaneous detection of 11 benzimidazole residues, including metabolites – albendazole, albendazole sulphoxide, albendazole sulphone, fenbendazole, fenbendazole sulphoxide (oxfendazole, fenbendazole sulphone, flubendazole, mebendazole, oxibendazole, thiabendazole, 5-hydroxythiabendazole – in bovine, ovine, equine, swine, rabbit and poultry liver and in bovine, swine and fish muscle. After extraction with a dicloromethane/acetonitrile solution (35/65 v/v containing 5% ammonium hydroxide, the solvent was evaporated to dryness, the residue was dissolved in HCl 0.1 M, defatted with hexane, purified on a strong cation exchange solid-phase extraction cartridge and analysed in HPLC with diode array and fluorescence detectors. The method was validated as screening qualitative method evaluating, according to Commission Decision 2002/657/EC criteria, specificity, CCb and b error at cut off level of 25 mg/kg and ruggedness.

  12. 2-(4-吡啶基)苯并咪唑对碳钢的缓蚀行为%Corrosion Inhibition of 2-(4-pyridyl)-benzimidazole for Carbon Steel

    Institute of Scientific and Technical Information of China (English)

    宋力; 张帆; 王海平; 余志荣; 唐永明

    2013-01-01

    采用失重法、极化曲线和电化学阻抗谱(EIS)等方法对2-(4-吡啶基)苯并咪唑(PBI)在盐酸体系中对碳钢的缓蚀行为进行了研究.结果表明,PBI对碳钢的腐蚀具有优良的抑制作用,其缓蚀效率随着缓蚀剂浓度的增大而升高,随着温度升高和盐酸浓度增大而下降.PBI能够自发吸附在碳钢表面,其吸附遵循Langmuir吸附等温式.%Weight loss, potentiodynamic polarization and electrochemical impedance spectroscopy (EIS) were used to investigate the corrosion inhibition of 2-(4-pyridyl)-benzimidazole (PBI) for carbon steel in hydrochloric acid. It is found that the inhibition efficiency of PBI increases with the increase of the concentration of PBI, and decreases with the increase in the temperature and concentration of hydrochloric acid. PBI is adsorbed on the surface of carbon steel spontaneously, and the adsorption of PBI obeys Langmuir isotherm.

  13. Synthesis and Structure of a 3D Manganese Coordination Polymer with 1,3-Bis(benzimidazol-1-ylmethyl)-2,4,6-trimethylbenzene and 1,5-Naphthalenedisulfonate

    Institute of Scientific and Technical Information of China (English)

    ZHOU Hui; DU Shao-Wu; LI Zhi-Hua

    2007-01-01

    The organic-inorganic hybrid polymer [Mn(mbbimb)2(1,5-nds)]n 1 has been synthesized using 1,5-naphthalenedisulfonate (1,5-nds) and 1,3-bis(benzimidazol-1-ylmethyl)- 2,4,structure analysis indicates that 1 crystallizes in monoclinic, space group C2/c with a=21.3546(17), b=11.8841(7), c=22.1588(16) (A), β=108.058(3)°, C60H54MnN8O6S2, Mr=1102.17, Z=4, V=5346.5(7)(A)3, Dc=1.369 g/cm3, μ=0.386 mm-1, F(000)=2300, S=1.091, R=0.0634 and wR=0.1559 for 4641 observed reflections (I > 2σ(I)). The Mn center is six-coordinated to furnish a distorted octahedral geometry, and the overall framework is a 6-connected 3D net.

  14. Hydrothermal Synthesis, Crystal Structure and Luminescence Properties of a New 2D Cadmium Complex Based on the 4,4'-Bis(benzimidazol-1-ylmethy1)biphenyl and Glutaric Acid Ligands

    Institute of Scientific and Technical Information of China (English)

    TAO Zhao-Lin; QIN Ling; CUI Jie-Hu; ZHENG He-Gen

    2013-01-01

    A new polymeric complex {[Cd2(bbmb)2(gt)2]·(H2O)2}n (bbmb =4,4'-bis(benzimidazol-1-ylmethy1)biphenyl,H2gt =glutaric acid) has been obtained by hydrothermal method and structurally characterized by elemental analysis,IR,XRD,TGA and single-crystal X-ray diffraction.The complex belongs to the triclinic system,space group P(-1) with a =10.2417(15),b =13.752(2),c =22.201(3) (A),a =73.899(2),β =88.416(2),γ =78.305(2)°,V =2940.4(7) (A)3,Z =2,C66H56Cd2N8O8,Mr =1313.99,Dc =1.484 g/cm3,F(000) =1336 andμ =0.787 mm-1,and features a 2D network.In the solid state at room temperature,the cadmium(Ⅱ) complex exhibits strong fluorescence absorption at 435 nm (λmax).

  15. Cadmium(Ⅱ) Nitrite Complex Based on the Bis(2-benzimidazole) and Aromatic Carboxylate Ligands%Cadmium(Ⅱ) Nitrite Complex Based on the Bis(2-benzimidazole) and Aromatic Carboxylate Ligands

    Institute of Scientific and Technical Information of China (English)

    JIANG Luan; FENG Guo-Dong; CHEN Qiang; YANG De-Suo; LI Zong-Xiao; LUO Xiao-Lin

    2012-01-01

    A new cadmium(Ⅱ) nitrite complex Cd2(H2C3PIm)2(BDC)(NO2)2(1,H2C3PIm = 2,2'-(1,3-propanediyl)bis(1H-benzimidazole),H2BDC = 1,4-benzenedicarboxylic acid) has been synthesized by solvothermal reaction in formamide,and its structure(C42H36Cd2N10O8,Mr = 1033.61) was determined by single-crystal X-ray diffraction analysis.The crystal belongs to the monoclinic system,space group P21/n with a = 0.9859(5),b = 0.8936(5),c = 2.3188(5) nm,β = 97.576(5)°,V = 2.025(16) nm3,Z = 2,Dc = 1.695 g/cm3,μ(MoKα) = 1.118 mm-1,F(000) = 1036,S = 1.017,the final R = 0.0304 and wR = 0.0752 for 3761 reflections with I 〉 2σ(I).The centrosymmetric complex 1 contains a dimer in which two distorted octahedral Cd(II) centers are bridged by BDC ligand and chelated by H2C3PIm.The units of the complex are linked via weak N-H···O hydrogen bonds between the nitrito and the BDC ligands,leading to the formation of a 1D zigzag chain along the b axis.The π-π packing interactions contribute to the formation of a three-dimensional supramolecular architecture.The complex exhibits strong photoluminescence at room temperature.

  16. Impairment of the ubiquitin-proteasome pathway by methyl N-(6-phenylsulfanyl-1H-benzimidazol-2-yl)carbamate leads to a potent cytotoxic effect in tumor cells: a novel antiproliferative agent with a potential therapeutic implication.

    Science.gov (United States)

    Dogra, Nilambra; Mukhopadhyay, Tapas

    2012-08-31

    In recent years, there has been a great deal of interest in proteasome inhibitors as a novel class of anticancer drugs. We report that fenbendazole (FZ) (methyl N-(6-phenylsulfanyl-1H-benzimidazol-2-yl)carbamate) exhibits a potent growth-inhibitory activity against cancer cell lines but not normal cells. We show here, using fluorogenic substrates, that FZ treatment leads to the inhibition of proteasomal activity in the cells. Succinyl-Leu-Leu-Val-Tyr-methylcoumarinamide (MCA), benzyloxycarbonyl-Leu-Leu-Glu-7-amido-4-MCA, and t-butoxycarbonyl-Gln-Ala-Arg-7-amido-4-MCA fluorescent derivatives were used to assess chymotrypsin-like, post-glutamyl peptidyl-hydrolyzing, and trypsin-like protease activities, respectively. Non-small cell lung cancer cells transiently transfected with an expression plasmid encoding pd1EGFP and treated with FZ showed an accumulation of the green fluorescent protein in the cells due to an increase in its half-life. A number of apoptosis regulatory proteins that are normally degraded by the ubiquitin-proteasome pathway like cyclins, p53, and IκBα were found to be accumulated in FZ-treated cells. In addition, FZ induced distinct ER stress-associated genes like GRP78, GADD153, ATF3, IRE1α, and NOXA in these cells. Thus, treatment of human NSCLC cells with fenbendazole induced endoplasmic reticulum stress, reactive oxygen species production, decreased mitochondrial membrane potential, and cytochrome c release that eventually led to cancer cell death. This is the first report to demonstrate the inhibition of proteasome function and induction of endoplasmic reticulum stress/reactive oxygen species-dependent apoptosis in human lung cancer cell lines by fenbendazole, which may represent a new class of anticancer agents showing selective toxicity against cancer cells.

  17. Rapid determination of benzimidazole pesticide in orange juice by liquid chromatography -mass spectrometry%LC-MS快速检测橙汁中苯并咪唑类农药

    Institute of Scientific and Technical Information of China (English)

    姚艳玲; 倪炜华; 顾益

    2013-01-01

    Objective: A method was established to rapidly determine carbendazim, thiophanate, thiophanate -methyl, 2 - aminobenzimidazole and triabendazole in orange juice by liquid chromatography - mass spectrometry. Methods; The orange juice was diluted with water, and then subjected to solid phase extraction using HLB 3cc cartridge. Then the extract was analyzed by liquid chromatography - mass spectrometry with a mobile phase of water and methanol at a flow rate of 0.20 ml/min. Results: The method showed good linearity in the range of 0.01 mg/L ~ 0. 10 mg/L, the average recoveries of the 5 benzimidazole pesticide in orange juice ranged from 75.0% to 97. 5% , the relative standard deviations ranged from 1. 0% ~ 8. 6% , the limit of detection was from 0. 0046 μg/kg ~ 0.0116 μg/kg. Conclusion; The method was applied to determine carbendazim, thiophanate, thiophanate - methyl, 2 - aminobenzimidazole and triabendazole in orange juice with satisfactory results.%目的:建立液相色谱质谱法快速检测橙汁中多菌灵、硫菌灵、甲基硫菌灵、2-氨基苯并咪唑和噻菌灵5种苯并咪唑类农药的试验方法.方法:样品直接用水稀释后,经HLB 3cc固相萃取柱净化,采用液相色谱质谱仪进行定性、定量分析,以水和甲醇为流动相,在0.20 ml/min下梯度洗脱.结果:该方法在0.01 mg/L~0.10 mg/L范围内呈良好的线性关系,平均回收率为75.0% ~ 97.5%,相对标准偏差为1.0% ~8.6%,检出限为0.0046 μg/kg ~0.0116 μg/kg.结论:该方法适用于橙汁中多菌灵、硫菌灵、甲基硫菌灵、2-氨基苯并咪唑和噻菌灵的检测.

  18. Synthesis, structure and biological activity of monocarboxylic/biscarboxylic-functionalized benzimidazole derivatives%单、双羧酸功能化苯并咪唑衍生物的合成、结构表征及生物活性

    Institute of Scientific and Technical Information of China (English)

    张有明; 郭英; 谢永强; 姚虹; 魏太保

    2013-01-01

    Synthesis of phenoxymethyl benzimidazole by a two-step reaction of phenol with chloroacetic acid and o-phenylenediamine has been studied. The latter suffers three reaction processes containing the Aza-Michael addition reacted with methyl acrylate, quaternarization and hydrolysis to give the title compound (N-carboxymethyl-N'-carboxyethyl-2-phenoxymethyl benzimidazole). Furthermore, 2-phenoxymethyl benzimidazole reacts with sodium chloroacetate to give the other title compound(N-carboxymethyl-2-phenoxymethyl benzimidazole). The compounds have been characterized via elemental analysis, FTIR and 1 HNMR. The molecular structure of the compound 6 is determined by single crystal X-ray diffraction. The results show that the compound crystallizes in the orthorhombic system with space group Pbac, a= 0. 973 67(9)nm,b=l. 263 44(12)nm,c = 2. 294 26(4)nm,α = 90°,β=90°,γ=90°,V=2. 822 34(4)nm3 ,Z= 8, F(000) = l 184. The cell packing diagram shows that the compound self-assembled with 1-dimensional chains supported by interrnolecular hydrogen bonding and further formed the 2-dimensional layered molecular structure by H-bonds. The results of the bioactivity properties show that the compounds have plant growth regulating activity, antibacterial and antifungal activity.%以苯酚为原料,经氯乙酸、邻苯二胺两步反应生成苯氧甲基苯并咪唑,再与丙烯酸甲酯经过N原子的Aza-Michael加成,接着与溴乙酸乙酯发生季铵化,然后在酸性条件下水解得到目标化合物N-羧甲基-N'-羧乙基-2-苯氧甲基苯并咪唑内鎓盐.另外,苯氧甲基苯并咪唑与氯乙酸钠反应生成另一目标化合物N-羧甲基-2-苯氧甲基苯并咪唑.经元素分析、IR和1HNMR对其结构进行表征,用单晶X射线衍射测定了化合物6的晶体结构.结果表明,化合物6属正交晶系,Pbac空间群,晶胞参数a=0.973 67(9) nm,b=1.26344(12) nm,c=2.294 26(4) nm,a=90°,β=90°,γ=90°,V=2.822 34(4) nm3,Z=8,F(000)=1 184.

  19. Crystal structure of poly[[μ-1,1′-(butane-1,4-diylbis(1H-benzimidazole-κ2N3:N3′]{μ-4,4′-[1,4-phenylenebis(oxy]dibenzoato-κ4O,O′:O′′,O′′′}cobalt(II

    Directory of Open Access Journals (Sweden)

    Chen Xie

    2015-06-01

    Full Text Available In the title compound, [Co(C20H12O6(C18H18N4]n, the CoII atom, located on a twofold rotation axis, is hexacoordinated to four O from two bis-bidentate 4,4′-[phenylenebis(oxy]dibenzoate (L ligands and two N atoms from two 1,1′-(butane-1,4-diylbis(1H-benzimidazole (bbbm ligands, forming a distorted octahedral cis-N2O4 coordination environment. Polymeric zigzag chains along [102] are built up by the bridging L ligands. These chains are additionally connected by the bbbm ligands to produce a two-dimensional coordination polymer parallel too (010.

  20. A novel and orally active poly(ADP-ribose) polymerase inhibitor, KR-33889 [2-[methoxycarbonyl(4-methoxyphenyl) methylsulfanyl]-1H-benzimidazole-4-carboxylic acid amide], attenuates injury in in vitro model of cell death and in vivo model of cardiac ischemia.

    Science.gov (United States)

    Oh, Kwang-Seok; Lee, Sunkyung; Yi, Kyu Yang; Seo, Ho Won; Koo, Hyun-Na; Lee, Byung Ho

    2009-01-01

    Blocking of poly(ADP-ribose) polymerase (PARP)-1 has been expected to protect the heart from ischemia-reperfusion injury. We have recently identified a novel and orally active PARP-1 inhibitor, KR-33889 [2-[methoxycarbonyl(4-methoxyphenyl)-methylsulfanyl]-1H-benzimidazole-4-carboxylic acid amide], and its major metabolite, KR-34285 [2-[carboxy(4-methoxyphenyl)methylsulfanyl]-1H-benzimidazole-4-carboxylic acid amide]. KR-33889 potently inhibited PARP-1 activity with an IC(50) value of 0.52 +/- 0.10 microM. In H9c2 myocardial cells, KR-33889 (0.03-30 microM) showed a resistance to hydrogen peroxide (2 mM)-mediated oxidative insult and significantly attenuated activation of intracellular PARP-1. In anesthetized rats subjected to 30 min of coronary occlusion and 3 h of reperfusion, KR-33889 (0.3-3 mg/kg i.v.) dose-dependently reduced myocardial infarct size. KR-34285, a major metabolite of KR-33889, exerted similar patterns to the parent compound with equi- or weaker potency in the same studies described above. In separate experiments for the therapeutic time window study, KR-33889 (3 mg/kg i.v.) given at preischemia, at reperfusion or in both, in rat models also significantly reduced the myocardial infarction compared with their respective vehicle-treated group. Furthermore, the oral administration of KR-33889 (1-10 mg/kg p.o.) at 1 h before occlusion significantly reduced myocardial injury. The ability of KR-33889 to inhibit PARP in the rat model of ischemic heart was confirmed by immunohistochemical detection of poly(ADP-ribose) activation. These results indicate that the novel PARP inhibitor KR-33889 exerts its cardioprotective effect in in vitro and in vivo studies of myocardial ischemia via potent PARP inhibition and also suggest that KR-33889 could be an attractive therapeutic candidate with oral activity for several cardiovascular disorders, including myocardial infarction.

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

    Institute of Scientific and Technical Information of China (English)

    吕世真; 李树娟; 王修光; 柳清湘

    2011-01-01

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

  2. Pharmacokinetics of Three Benzimidazoles Suspended in Oleic Acid,Soybean Oil or 1% Tragacanth,and Administered Orally to Mice at A Single Dose%小鼠口服3种苯并咪唑类药物的油酸、大豆油和1%西黄耆胶混悬剂的药动学

    Institute of Scientific and Technical Information of China (English)

    姜斌; 张皓冰; 刘丛珊; 陶奕

    2012-01-01

    OBJECTIVE To determine the pharmacokinetics of three benzimidazoles ( albendazole, fenbendazole and fluben-dazole) suspended in three different media [oleic acid, soybean oil or 1% tragacanth (served as control) ] in mice, and observe the correlation of those pharmacokinetic parameters with the solubilities of the three benzimidazoles in corresponding medium. METHODS Albendazole, fenbendazole and flubendazole suspened in oleic acid, soybean oil or 1% tragacanth were prepared by ball grinding mill. Groups of 45 - 54 mice were administered orally with one of aforementioned benzimidazole suspensions at a single dose of 100 mg·kg-1 ( albendazole) or 50 mg·kg-1 (fenbendazole and flubendazole). Subgroups with 5-6 mice in each group were bled at varying intervals within 24 h. Plasma was then separated from heparin-anticoagulated blood, and evaluated for the presence of the drug by high performance liquid chromatography ( HPLC ). Pharmacokinetic parameters of each drug were calculated using DAS ( Drug AnaLyze System). RESULTS After oral administration of three benzimidazoles suspended in oleic acid, soybean oil or 1% tragacanth, the pharmacokinetic parameters of each drug were described as follows; albendazole, the MRT (average retention time) were (3. 91 ± 0.29), (3.70±0.09) and (1. 59 ± 0. 14) h, ρmax (maximum concentration) were (0.66±0.08), (0.29±0.05) and (0. 34±0. 09) mg·L-1 , AUC (area under the concentration-time curve) were (3. 19 ±0.40) , (1. 25 ±0.09) and (0. 50 ±0. 05) mg·L·h-1, F (relative bioavailability, the AUC compared with that of 1% tragacanth group) were 6. 38 and 2. 50; fenbendazole, the MRT were (5. 72 ±0. 14) , (4. 83 ±0.38) and (3. 85 ±0.25) h, ρmax were( 0. 70 ± 0. 11) , (0.20 ±0.05) and (0. 12 ±0.03) mg·L-1 , AUC were (5. 02 ±0.73) , (1.08 ±0.21) and (0.52 ±0.07) mg·h·L-1 , F were 9.65 and 2.08; flubendazole, the MRT were (5.71 ±0.37), (4.59±0.39) and (3. 34 ±0.20) h, pmax were (0.93 ±0. 14), (0.58 ±0.09) and (0

  3. Nitrato-complexes of Y(III), La(III), Ce(III), Pr(III), Nd(III), Sm(III), Gd(III), Tb(III), Dy(III) and Ho(III) with 2-(2'-pyridyl) benzimidazole

    International Nuclear Information System (INIS)

    The nitrato-complexes, [Y(PyBzH)2(NO3)2]NO3.H2O and Nd, Sm, Gd, Tb, Dy, Ho ; n=1-3, m=0-0.5 ; PyBzh=2-(2 -pyridyl)benzimidazole] are formed on interaction of the ligand with metal nitrates in ethanol. The electrical conductance values (116-129 ohm-1cm2mol-1) suggest 1:1 electrolyte-nature of the complexes. Magnetic moment values of Ce(2.53 B.M.), Pr(3.62 B.M.), Nd(3.52 B.M.), Sm(1.70 B.M.), Gd(8.06 B.M.), Tb(9.44 B.M.), Dy(10.56 B.M.) and Ho(10.51 B.M.) in the complexes confirm the terpositive state of the metals. Infrared evidences are obtained for the existance of both coordinated (C2v) and uncoordinated (D3h) nitrate groups. Electronic absorption spectra of Pr(III)-, Nd(III)-, Sm(III)-, Tb(III)-, Dy(III)- and Ho(III)-complexes have been analysed in the light of LSJ terms. (author)

  4. 2-(3-甲氧基-4-羟基苯基)苯并咪唑的碳钢海水缓蚀性能%The Corrosion Inhibiton Performance of 2-(3-methoxy-4-hydroxyphenyl) Benzimidazole for Carbon Steel in Saltwater

    Institute of Scientific and Technical Information of China (English)

    茌方; 周桃玉

    2014-01-01

    本文研究合成了样品2-(3-甲氧基-4-羟基苯基)苯并咪唑(BID),并采用傅立叶红外光谱(FT-IR)和紫外光谱对其进行了表征。同时,采用电化学极化曲线(EPC)、交流阻抗谱(EIS)和腐蚀失重法测试了BID的缓蚀效果。结果表明,BID在3.5%NaCl溶液中对Q235碳钢有约75%的缓蚀效果,腐蚀速率降至0.115mm/a,其作用效果为阳极抑制型。%In this paper, 2-(3-methoxy-4-hydroxyphenyl)benzimidazole(BID) is synthesized and characterized by Fourier transform infrared spectroscopy(FT-IR) and ultraviolet spectroscopy. Its corrosion inhibition performance is investigated by electrochemical polarization curves(EPC), electrochemical impedance spectroscopy(EIS) and weight loss methods. The results show that, with the presence of BID in 3.5%NaCl solution, the corrosion rate of Q235 steel dropped to 0.115mm/a and inhibition efficiency reaches to about 75%, which act as anodic type inhibitor in saltwater solution.

  5. Acetylene- and Phenylacetylene-Terminated Poly(Arylene Ether Benzimidazole)s (PAEBI's)

    Science.gov (United States)

    Connell, John W.; Hergenrother, Paul M.; Smith, Joseph G., Jr.

    1994-01-01

    Polymers prepared by first synthesizing polymers terminated with hydroxy groups, then reacting them with either 4-ethynylbenzoyl chloride or 4-fluoro-4'-phenylethynylbenzophenone. Endcapped polymers thermally cured to yield materials with attractive combination of properties. Cured acetylene-and phenylacetylene-terminated PAEBI's exhibit higher glass-transition temperatures and better retention of mechanical properties at high temperatures. Cured acetylene- and phenylacetylene-terminated polymers exhibit excellent adhesion to copper foil and polyimide film. Potentially useful as adhesives, coatings, composite matrices, fibers, films, membranes, and moldings.

  6. Poly(imide benzimidazole)s for high temperature polymer electrolyte membrane fuel cells

    DEFF Research Database (Denmark)

    Yuan, Sen; Guo, Xiaoxia; Aili, David;

    2014-01-01

    % orthophosphoric acid under pressure at 180°C to give acid uptakes as high as 780wt% and anhydrous proton conductivity of up to 0.26Scm-1 at elevated temperatures. The PIBI membrane with a 1:1molar ratio of APABI:ODA (PIBI-1/1) and with an acid uptake of 300wt% showed an elastic modulus of 0.1GPa at 160°C, which...

  7. 2-[[(4.吡啶)甲基]硫]-1H-苯并咪唑Ni(Ⅱ)配合物的合成、晶体结构及热稳定性%Synthesis,Crystal Structure and Thermal Stability of Ni(Ⅱ)Complex with 2-[[(4-Pyridyl)methyl]thio]-1H-benzimidazole

    Institute of Scientific and Technical Information of China (English)

    刘家成; 洪慧琴; 宋雪艳; 楚朝霞; 陈立伟

    2011-01-01

    本文报道了fNiL2(NCS)2(CH3OH)2](L=2.[[(4-吡啶)甲基]硫]-1H-苯并咪唑)配合物的合成,并通过IR、X-射线单晶衍射、热稳定性进行了表征.晶体结构测试表明:该配合物属于单斜晶系,空间群 P21/n,晶胞参数:α=94420(12)nm,b=1.35733(17)am,c=1.341 64(17)nm,β=97.9830(10)°,V=1.7028(4)am3,Z=2,F(000)=748,D=1.407 g·cm-3,Final GooF=1.027,R1=0.0468,wR2=0.1071.中心Ni(Ⅱ)原子采用六配位,分别与2个2-I[(4-吡啶)甲基]硫]-1H-苯并咪唑上的2个N原子,2个硫氰酸根的2个N原子和2个甲醇分子上的2个0原子进行配位.在Ni(Ⅱ)基本配位单元之间存在N…H-O氢键,形成一维双链堆积结构.%A nickel(Ⅱ) complex [NiL2(NCS)2 (CH3OH)2] (L =2-[[(4-Pyridyl)methyl]thio]-1H-benzimidazole) was synthesized and characterized by IR spectra, X-ray diffraction and TG analysis. Crystal data for this complex:monoclinic, space group P21/n, a=0.944 20(12) nm, b=1.357 33(17) nm, c=1.341 64(17) nm, β=97.983 0(10)。, V=1.7028(4) nm3, Z=2, F(000)=748, Dc=1.407 g·cm-3, Final GooF=1.027, R1=0.0468, wR2=0.107 1. The crystal structure shows the nickel(Ⅱ) atom is six-coordinated with two nitrogen atoms from two 2-[[(4-Pyridyl)methyl]thio]1H-benzimidazole, the other two nitrogen atoms from two thiocyanate radical and two oxygen atoms from methanol molecules. The double-chain one dimensional motifs are formed by hydrogen bonds N…H-O conecting different nickel(Ⅱ) units. CCDC: 792992.

  8. Investigation of Excited-State Proton Transfer of 2-(3-Acetamido-2-pyridyl)benzimidazole in the Confined Nanocavity of Cucurbit[7]uril%七元瓜环纳米腔限制环境下2-(3-乙酰胺基-2-吡啶基)苯并咪唑的激发态质子转移

    Institute of Scientific and Technical Information of China (English)

    易平贵; 阳习春; 刘金; 侯博; 于贤勇; 李筱芳; 汪朝旭; 郑柏树

    2013-01-01

    The interaction of2-(3-acetamido-2-pyridyl)-benzimidazole (2-3Am2PyBI) with cucurbit[7]uril (CB7) macrocycle and the effect of inclusion on the proton transfer of 2-3Am2PyBI were studied by using emission fluorescence,1H NMR spectra and quantum chemical calculation.By the way,the proton transfer of the dye with and without acetyl (2-3A2PyBI) was also studied.The results indicate that the acetyl promoted the process of proton transfer of the benzimidazole and the cationic form binds with CB7 easier than the other forms of the dye.The fluorescence studying at selected pHs suggest that the proton transfer process of the dye was retarded by interacting with CB7 nanocavity and the molar rate is host ∶ guest=1 ∶ 1 analyzed by the Benesi-Hildebrand method.The dye entered into the CB7 cavity with its benzene ring was proved by the 1H NMR titration experiment and the protonated forms were verified by the quantum calculation with fluorescence spectra.%以荧光发射光谱,1H NMR谱及量子化学计算研究了2-(3-乙酰胺基-2-吡啶基)苯并咪唑(2-3Am2PyBI)质子转移过程及其与七元瓜环超分子(CB7)的包合作用,考察了乙酰基取代基效应及CB7的包合作用对2-3Am2PyBI质子转移过程的影响.结果表明:乙酰基取代促进了质子转移过程;2-3Am2PyBI阳离子构型更易与CB7发生包合作用;在特定溶液pH值条件下,摩尔比法荧光光谱实验表明超分子包合作用抑制了2-3Am2PyBI的激发态质子转移过程;Benesi-Hildebrand方程拟合得到,超分子体系的包合比为1∶1;1H NMR测试进一步表明2-3Am2PyBI以苯环部分进入CB7的空腔,同时,以量化计算与荧光实验结合,从理论与实验方面共同验证了2-3Am2PyBI的质子转移异构体.

  9. Conjugation of organoruthenium(II) 3-(1H-benzimidazol-2-yl)pyrazolo[3,4-b]pyridines and indolo[3,2-d]benzazepines to recombinant human serum albumin: a strategy to enhance cytotoxicity in cancer cells.

    Science.gov (United States)

    Stepanenko, Iryna N; Casini, Angela; Edafe, Fabio; Novak, Maria S; Arion, Vladimir B; Dyson, Paul J; Jakupec, Michael A; Keppler, Bernhard K

    2011-12-19

    Following our strategy of coupling cyclin-dependent kinase (Cdk) inhibitors with organometallic moieties to improve their physicochemical properties and bioavailability, five organoruthenium complexes (1c-5c) of the general formula [RuCl(η(6)-arene)(L)]Cl have been synthesized in which the arene is 4-formylphenoxyacetyl-η(6)-benzylamide and L is a Cdk inhibitor [3-(1H-benzimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridines (L1-L3) and indolo[3,2-d]benzazepines (L4 and L5)]. All of the compounds were characterized by spectroscopic and analytical methods. Upon prolonged standing (2-3 months) at room temperature, the dimethyl sulfoxide (DMSO) solutions of 1c and 2c(-HCl) afforded residues, which after recrystallization from EtOH and EtOH/H(2)O, respectively, were shown by X-ray diffraction to be cis,cis-[Ru(II)Cl(2)(DMSO)(2)(L1)]·H(2)O and mer-[Ru(II)Cl(DMSO)(3)(L2-H)]·H(2)O. Compound 5c, with a coordinated amidine unit, undergoes E/Z isomerization in solution. The antiproliferative activities and effects on the cell cycle of the new compounds were evaluated. Complexes 1c-5c are moderately cytotoxic to cancer cells (CH1, SW480, A549, A2780, and A2780cisR cell lines). Therefore, in order to improve their antiproliferative effects, as well as their drug targeting and delivery to cancer cells, 1c-5c were conjugated to recombinant human serum albumin, potentially exploiting the so-called "enhanced permeability and retention" effect that results in the accumulation of macromolecules in tumors. Notably, a marked increase in cytotoxicity of the albumin conjugates was observed in all cases.

  10. Synthesis, Structure and Geometrical Calculation of a Novel Co-crystal of {[4-Bromo-2-(benzimidazol-2-yl)phenolato][2- (1-butylbenzimidazol-2-yl)phenolato]zinc(Ⅱ)] and Bis[μ-2- (1- butylbenzimidazol-2-yl)phenolato]- 1κN3: 2κO; 1κO:2κN3-bis{[2-(1-butylbenzimidazol-2-yl)phenolato-κ2N3,O]zinc(Ⅱ)}

    Institute of Scientific and Technical Information of China (English)

    TONG Yi-Ping

    2007-01-01

    The title compound has been synthesized and characterized crystallographically. It is a co-crystal consisting of two different neutral zinc(Ⅱ) complexes with Hbpbm (Hbpbm = 4-bromo-2-(benzimidazol-2-yl)phenol) and Hnpbm (Hnpbm = 2-(1-butylbenzimidazol-2-yl)phenol).One is a monomeric mixed-ligand complex of [Zn(bpbm)(npbm)] 1 and the other a dimer of[Zn2(npbm)4] 2 with their ratio of 2:1. Thus the overall formula for the title compound is 21·2.Adjacent 1 and 2 are connected to each other by intermolecular hydrogen bonding interactions in the lattice. The crystal data: monoclinic, space group P21/c, a= 15.0141(12), b = 20.9941(17), c =18.4686(15) (A), β = 97.445(2)°, V= 5772.4(8) (A)3, Mr= 2429.68, Z = 2, Dc = 1.398 g/cm3,μ = 1.579mm-1, F(000) = 2504, R = 0.0637 and wR = 0.1771 for 6464 observed reflections (I> 2σ(Ⅰ)). The geometrical structure for 1 has also been theoretically optimized and compared with the experimental one.

  11. Glucogeno sintasa en helmintos parasitos: inhibicion por benzimidazoles

    OpenAIRE

    H. Gomez-Banqueri; M. A. Garcia Ruiz; M. Monteoliva; Sanchez-Moreno, M.

    1987-01-01

    Se ha determinado el effecto inhibidor sobre la actividad Glucogeno sintetasa (E.C.2.41.11) por parte de cuatro antihelminticos: Albendazol, Mebendazol, Parbendazol y Tiabendazol. Observandose que en todos los casos, es el Parbendazol quien ha demostrado un mayor poder inhibidor sobre la glucógeno sintetasa de Ascaris suum, Fasciola hepatica y Moniezia expansa. El Tiabendazol es el anti-helmintico que menor efecto inhibidor ha presentado sobre la enzima en los tres parasitos objeto de nuestro...

  12. 1-Methyl-6-nitro-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Svetozar Katuščák

    2008-04-01

    Full Text Available The title compound, C8H7N3O2, a potential antitumour drug and an antioxidant agent, was studied in order to give more insight into structure–function relationships. The 1-methylbenzimidazole unit of the molecule was found to be exactly planar and the nitro group is inclined at an angle of 10.4 (2° to the plane of the heterocycle. The bond lengths in the present derivative were analyzed in details and compared with those of the parent unsubstituted analogues in the Cambridge Structural Database. The results have shown that the additional nitro group is not involved in conjugation with the adjacent π-system and hence has no effect on the charge distribution of the heterocyclic ring.

  13. Synthesis and investigation of novel benzimidazole derivatives as antifungal agents.

    Science.gov (United States)

    Chandrika, Nishad Thamban; Shrestha, Sanjib K; Ngo, Huy X; Garneau-Tsodikova, Sylvie

    2016-08-15

    The rise and emergence of resistance to antifungal drugs by diverse pathogenic fungal strains have resulted in an increase in demand for new antifungal agents. Various heterocyclic scaffolds with different mechanisms of action against fungi have been investigated in the past. Herein, we report the synthesis and antifungal activities of 18 alkylated mono-, bis-, and trisbenzimidazole derivatives, their toxicities against mammalian cells, as well as their ability to induce reactive oxygen species (ROS) in yeast cells. Many of our bisbenzimidazole compounds exhibited moderate to excellent antifungal activities against all tested fungal strains, with MIC values ranging from 15.6 to 0.975μg/mL. The fungal activity profiles of our bisbenzimidazoles were found to be dependent on alkyl chain length. Our most potent compounds were found to display equal or superior antifungal activity when compared to the currently used agents amphotericin B, fluconazole, itraconazole, posaconazole, and voriconazole against many of the strains tested. PMID:27301676

  14. 5-Nitro-2-trifluoromethyl-1H-benzimidazole monohydrate

    Directory of Open Access Journals (Sweden)

    Ming-Liang Liu

    2012-05-01

    Full Text Available In the crystal structure of the title compound, C8H4F3N3O2·H2O, the main molecule and the water molecule are linked by an N—H...O hydrogen bond. O—H...N, O—H...O and C—H...O hydrogen bonds further link the molecules into sheets.

  15. Benzimidazole-derived anion for lithium-conducting electrolytes

    Science.gov (United States)

    Niedzicki, Leszek; Oledzki, Piotr; Bitner, Anna; Bukowska, Maria; Szczecinski, Przemyslaw

    2016-02-01

    In this work we announce new lithium salt of 5,6-dicyano-2-(trifluoromethyl)benzimidazolide (LiTDBI) designed for application in lithium conductive electrolytes. It was synthesized and completely characterized by NMR techniques. Studies show salt's thermal stability up to 270 °C and electrochemical stability in liquid solvents up to +4.7 V vs. metallic lithium anode. Basic characterization of electrolytes made with this salt show conductivity over 1 mS cm-1 and unusually high transference number at high concentrations (0.74 in EC:DMC 1:2 ratio mixture) along with low onset of conductivity peak. As a final proof of concept, cycling in half-cell was performed and electrolyte based on LiTDBI showed perfect capacity retention. Such properties show remarkable progress in creating efficient lithium-conducting electrolytes with use of weakly-coordinating anions.

  16. 2-(1H-Benzimidazol-2-ylphenol

    Directory of Open Access Journals (Sweden)

    S. M. Prakash

    2014-02-01

    Full Text Available The title molecule, C13H10N2O, is essentially planar, the maximum deviation from the plane of the non-H atoms being 0.016 (2 Å. The imidazole ring makes a dihedral angle of 0.37 (13° with the attached benzene ring. An intramolecular O—H...N hydrogen bond generates an S(6 ring motif. In the crystal, molecules are linked through N—H...O hydrogen bonds, forming chains propagating in [001]. The crystal packing also features four π–π stacking interactions involving the imidazole ring, fused benzene ring and attached benzene ring system [centroid–centroid distances = 3.6106 (17, 3.6108 (17, 3.6666 (17 and 3.6668 (17 Å].

  17. 2-Diphenylphosphanyl-1-methyl-1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Zerihun Assefa

    2013-08-01

    Full Text Available In the title compound, C20H18N2P, the P atom is bonded to the two phenyl and imidazole groups, with an average P—C bond length of 1.828 (2 Å. The three C—P—C bond angles have values consistent with a tetrahedral geometry around the P atom with the fourth site occupied by a H atom. Crystal packing is through van der Waals interactions.

  18. 2-Methyl-1H-benzimidazol-3-ium hydrogen phthalate

    Directory of Open Access Journals (Sweden)

    YuanQi Yu

    2011-10-01

    Full Text Available The asymmetric unit of the title compound, C8H9N2+·C8H5O4−, contains two independent ion pairs. In each 2-methyl-1H-benzimidazolium ion, an intramolecular O—H...O bond forms an S(7 graph-set motif. In the crystal, the components are linked by N—H...O hydrogen bonds, forming chains along [210]. Further stabilization is provided by weak C—H...O hydrogen bonds.

  19. Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives

    Directory of Open Access Journals (Sweden)

    Immadisetty Sri Krishnanjaneyulu

    2014-01-01

    Full Text Available A series of novel N-((1H-benzoimidazol-1-yl methyl-4-(1-phenyl-5-substituted-4, 5-dihydro-1-benzoimidazol-1-yl methyl-4-(1-phenyl-5-substituted-4, 5-dihydro-1H-pyrazol-3-yl benzenamine were synthesized by treating various 1-(4-((1H-benzoimidazol-1-yl methylamino phenyl-3-substitutedprop-2-en-1-one with phenyl hydrazine in the presence of sodium acetate through a simple ring closure reaction. The starting material, 1-(4-((1H-benzoimidazol-1-yl methylamino phenyl-3-substitutedprop-2-en-1-one,-benzoimidazol-1-yl methylamino phenyl-3-substitutedprop-2-en-1-one, was synthesized from o-phenylenediamine by a multistep synthesis. All the synthesized compounds were characterized by spectroscopic means and elemental analyses. The title compounds were investigated for in vitro antibacterial and antifungal properties against some human pathogenic microorganisms by employing the agar streak dilution method using Ciprofloxacin and Ketoconazole as standard drugs. All title compounds showed activity against the entire strains of microorganism. Structural activity relationship studies reveal that compounds possessing an electron-withdrawing group display better activity than the compounds containing electron-donating groups, whereas the unsubstituted derivatives display moderate activity. Based on the results obtained, N-((1H-benzoimidazol-1-yl methyl-4-(1-phenyl-5-(4-(trifluoromethyl phenyl-4,5-dihydro-1H-pyrazol-3-yl benzenamine 5i was found to be very active compared with the rest of the compounds and standard drugs that were subjected to antimicrobial assay.

  20. Properties of polymer electrolyte membranes based on poly(Aryl ether benzimidazole) and sulphonated poly(Aryl ether benzimidazole) for high temperature PEMFCs

    Energy Technology Data Exchange (ETDEWEB)

    Dai, H.; Jin, H.; Xiao, S.; Mai, Z. [Laboratory of PEMFC Key Materials and Technologies, Dalian Institute of Chemical Physics, Chinese Academy of Science, 457 Zhongshan Road, Dalian, Liaoning (China); Graduate School of the Chinese Academy of Sciences, Beijing 100039 (China); Zhong, H.; Li, X. [Laboratory of PEMFC Key Materials and Technologies, Dalian Institute of Chemical Physics, Chinese Academy of Science, 457 Zhongshan Road, Dalian, Liaoning (China); Zhang, H.

    2010-10-15

    Membranes based on poly[2,2'-(p-oxydiphenylene)-5,5'-bibenzimidazole] (OPBI) and their sulphonated derivatives (SOPBI) were prepared and first investigated for high temperature proton exchange membrane fuel cells. OPBI and SOPBI membranes with good chemical stability were prepared by casting from their dimethyl sulphoxide (DMSO) solution and then impregnated in phosphoric acid baths to obtain H{sub 3}PO{sub 4} (PA)-doped membranes. The properties of PA-doped OPBI membranes, including phosphoric acid uptake, swelling ratio, mechanical properties and thermal properties, were fully investigated and compared with PA-doped SOPBI membranes. The fuel cell performances of PA-doped OPBI and SOPBI membranes at different temperatures were first evaluated. When doped in different concentrations of H{sub 3}PO{sub 4} solution, OPBI membranes adsorb more acid than SOPBI membranes. SOPBI membranes exhibit obviously lower swelling ratio in thickness direction than that of OPBI membranes. With an acid uptake of {proportional_to}110 wt.-%, corresponding doping level around 5, PA-doped OPBI and SOPBI membranes keep reasonably high tensile strength. PA-doped OPBI membranes exhibit peak power density of 0.78 W cm{sup -2} at 170 C and 0.25 MPa. With the same acid uptake, PA-doped SOPBI membranes displayed similar fuel cell performance to that of PA-doped OPBI membranes. (Abstract Copyright [2010], Wiley Periodicals, Inc.)

  1. 1,3-Bis(pyridin-2-yl-1H-benzimidazol-3-ium tetrafluoridoborate

    Directory of Open Access Journals (Sweden)

    Gabriele Grieco

    2011-08-01

    Full Text Available The asymmetric unit of the title compound, C17H13N4+·BF4−, contains one half of the benzimidazolium cation and one half of the tetrafluoridoborate anion, with crystallographic mirror planes bisecting the molecules. One F atom of the tetrafluoridoborate is equally disordered about a crystallographic mirror plane. In the crystal, C—H...F interactions link the cations and anions into layers parallel to (100. The crystal packing is further stabilized by F...π contacts involving the tetrafluoridoborate anions and the five-membered rings [F...centroid = 2.811 (2 Å].

  2. Bis[μ-3-(1H-benzimidazol-2-ylbenzoato]dicopper(I

    Directory of Open Access Journals (Sweden)

    Zheng-Yu Su

    2010-12-01

    Full Text Available The dimeric title complex, [Cu2(C14H9N2O22], resides on a center of symmetry. In the crystal, the molecules are packed via π–π stacking interactions alternating between imidazole and benzene rings [mean interplanar distances = 3.754 (3 and 3.624 (3 Å]. An intermolecular N—H...O hydrogen bond links the dimers together. The two-coordinate CuI atom displays an O—Cu—N bond angle of 176.3 (2°. The Cu...Cu distance within the dimer is 5.100 (2 Å.

  3. Tetrakis(1H-benzimidazole-κN3(nitrato-κOcopper(II nitrate

    Directory of Open Access Journals (Sweden)

    Fu-Lin Zhou

    2011-06-01

    Full Text Available In the title salt, [Cu(NO3(C7H6N24]NO3, one nitrate anion is coordinated to the CuII atom, which is also coordinated by the N atoms of four N-heterocycles. The geometry at the metal atom is a square pyramid in which the O atom of the anion occupies the apical position [Cu—O = 2.468 (5 and 2.590 (7 Å in the two independent formula units]. The cation lies on a twofold rotation axis; the coordinated nitrate anion is also disordered about this symmetry element. The lattice anion is also disordered about a twofold rotation axis. In the crystal, the cations are linked to the coordinated and free anions by N—H...O hydrogen bonds.

  4. 1-Decyl-6-nitro-1H-benzimidazol-2(3H-one

    Directory of Open Access Journals (Sweden)

    Younes Ouzidan

    2011-11-01

    Full Text Available The title molecule, C17H25N3O3, is built up from fused six- and five-membered rings linked to a –C10H21 chain. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2 Å. The chain is roughly perpendicular to this plane, making a dihedral angle of 79.5 (2°. In the crystal, N—H...O hydrogen bonds build infinite chains along [010]. There are channels in the structure containing disordered hexane. The contribution of this solvent to the scattering power was suppressed using the SQUEEZE option in PLATON [Spek (2009. Acta Cryst. D65, 148–155].

  5. Construction and screening of 2-aryl benzimidazole library identifies a new antifouling and antifungal agent.

    Digital Repository Service at National Institute of Oceanography (India)

    Majik, M.S.; Tilvi, S.; Mascarenhas, S.; Kumar, Vikash.; Chatterjee, Amrita; Banerjee, Mainak.

    and 4l, showed a broad spectrum of antifouling activities against nine marine fouling species, whereas 2-(furan-2-yl)-1H-benzo[d]imidazole 4g showed strong antifungal activity against the clinical pathogen Aspergillus niger. Our results reveal that the 2...

  6. Bis-benzimidazole hits against Naegleria fowleri discovered with new high-throughput screens.

    Science.gov (United States)

    Rice, Christopher A; Colon, Beatrice L; Alp, Mehmet; Göker, Hakan; Boykin, David W; Kyle, Dennis E

    2015-04-01

    Naegleria fowleri is a pathogenic free-living amoeba (FLA) that causes an acute fatal disease known as primary amoebic meningoencephalitis (PAM). The major problem for infections with any pathogenic FLA is a lack of effective therapeutics, since PAM has a case mortality rate approaching 99%. Clearly, new drugs that are potent and have rapid onset of action are needed to enhance the treatment regimens for PAM. Diamidines have demonstrated potency against multiple pathogens, including FLA, and are known to cross the blood-brain barrier to cure other protozoan diseases of the central nervous system. Therefore, amidino derivatives serve as an important chemotype for discovery of new drugs. In this study, we validated two new in vitro assays suitable for medium- or high-throughput drug discovery and used these for N. fowleri. We next screened over 150 amidino derivatives of multiple structural classes and identified two hit series with nM potency that are suitable for further lead optimization as new drugs for this neglected disease. These include both mono- and diamidino derivatives, with the most potent compound (DB173) having a 50% inhibitory concentration (IC50) of 177 nM. Similarly, we identified 10 additional analogues with IC50s of 500 times more potent than pentamidine. In summary, the mono- and diamidino derivatives offer potential for lead optimization to develop new drugs to treat central nervous system infections with N. fowleri.

  7. 6-Methoxy-2-methyl-1-m-tolyl-1H-benzimidazole hemihydrate

    Directory of Open Access Journals (Sweden)

    Xu-Bin Fang

    2011-09-01

    Full Text Available The title compound, C16H16N2O·0.5H2O, is a substituted 1-phenylbenzimidazole, which belongs to the class of ATP-site inhibitors of the platelet-derived growth-factor receptor. In the crystal, the components are linked by an O—H...N hydrogen bond.

  8. 2,2′-(Ethane-1,2-diylbis(1H-benzimidazole

    Directory of Open Access Journals (Sweden)

    Guo-Liang Zhao

    2012-05-01

    Full Text Available The complete molecule of the title compound, C16H14N4, is generated by crystallographic inversion symmetry. In the crystal, molecules are linked by N—H...N hydrogen bonds, generating (001 sheets. Weak aromatic π–π stacking interactions [centroid–centroid distances = 3.7383 (13 and 3.7935 (14 Å] are also observed.

  9. Pharmacophore Distance Mapping and Docking Study of Some Benzimidazole Analogs as A2A Receptor Antagonists

    Directory of Open Access Journals (Sweden)

    Santosh P. Ghatol

    2010-01-01

    Full Text Available Extracellular adenosine regulates a wide range of functions in higher organisms, in which the effects are mediated by a family of four class A (rhodopsin-like GPCRs, a, adenosine receptors known as A1, A2A, A2B, and A3. A2A antagonists, either alone or in combination with dopamine agonists, can have a role in the treatment of neurodegenerative movement disorders such as Parkinson’s disease and Huntington’s disease. The concept of a pharmacophore is widely used in modern drug design and it is generally defined as the 3D arrangement of certain features in the ligand that are responsible for its activity against a particular protein target. Docking involves, the process of fitting the ligand into receptor, and the compounds which fit in them properly are assumed to be active for that receptor and it gives corresponding docking scores.

  10. Alkali doped poly (2,5-benzimidazole) membrane for alkaline water electrolysis: Characterization and performance

    Science.gov (United States)

    Diaz, Liliana A.; Hnát, Jaromír; Heredia, Nayra; Bruno, Mariano M.; Viva, Federico A.; Paidar, Martin; Corti, Horacio R.; Bouzek, Karel; Abuin, Graciela C.

    2016-04-01

    The properties and performance of linear and cross-linked KOH doped ABPBI membranes as electrolyte/separator for zero gap alkaline water electrolysis cells are evaluated and compared with a commercial Zirfon® diaphragm. Stability in alkaline environment, swelling, thermal properties, water sorption, KOH uptake and conductivity of linear (L-ABPBI) and cross-linked (C-ABPBI) membranes doped with different concentrations of KOH are analyzed. Linear membranes show stability up to 3.0 mol·dm-3 KOH doping, while cross-linked membranes are stable up to 4.2 mol·dm-3 KOH doping. Both kinds of membranes exhibit good thermal stability and reasonable specific ionic conductivity at 22 °C in the range between 7 and 25 mS·cm-1, being slightly higher the conductivity of C-ABPBI membranes than that of L-ABPBI ones. In short-term electrolysis tests both L-ABPBI and C-ABPBI membranes show better performance than Zirfon diaphragm in the range from 50 to 70 °C. A current density of 335 mA·cm-2 at a cell voltage of 2.0 V is attained with C-ABPBI membranes doped in 3 mol·dm-3 KOH at 70 °C, a performance comparable with that of commercial units operating at temperatures ca. 80 °C and 30 wt% KOH (6.7 mol·dm-3) as electrolyte.

  11. Synthesis of Cyclohexyl and Isopropyl Ketones from Benzimidazole Methiodide Salt and Grignard Reagents

    Institute of Scientific and Technical Information of China (English)

    杨秉勤; 强琚莉; 白银娟; 路军; 史真

    2003-01-01

    The reaction of 2-alkyl-l, 3-dimethylbenzimidazolinm salts with Grignard reagents gave addition products which were hy-drelyzed to give ketones. A new method for the preparation of cyclohexyl ketones and isopropyl ketones is provided.

  12. Electronic spectra and DFT calculations of some pyrimido[1,2-a]benzimidazole derivatives

    Science.gov (United States)

    Elshakre, Mohamed E.; Moustafa, H.; Hassaneen, Huwaida. M. E.; Moussa, Abdelrahim. Z.

    2015-06-01

    Ground state properties of 2,4-diphenyl-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine, compound 1, and its derivatives are investigated experimentally and theoretically in Dioxane and DMF. The calculations show that all the studied compounds (1-7) are non-planar, resulting in a significant impact on the electronic and structural properties. The ground state properties of compounds 1-7 at B3LYP/6-311G (d, p) show that compound 5 has the lowest EHOMO, ELUMO, and ΔE indicating highest reactivity. Compound 7 is found to have the highest polarity. The observed UV spectra in Dioxane and DMF of compounds 1-4 show 2 bands, while compounds 5-7 show 4 bands in both solvents. Band maxima (λmax) and intensities of the spectra are found to have solvent dependence reflected as blue and red shifts. The theoretical spectra computed at TD-B3LYP/6-311G (d, p) in gas phase, Dioxane and DMF indicate a good agreement with the observed spectra.

  13. Microwave-assisted Syntheses and Crystal Structures of Benzimidazole Thiazolinone Derivatives

    Institute of Scientific and Technical Information of China (English)

    HU Jun; WANG Peng; WANG Ji-Kui; XU Yan-Hua

    2012-01-01

    A rapid and efficient microwave-assisted synthesis method for the preparation of 3-(lH-benzo[d]imidazol-2-yl)-2-substituted phenyl thiazolidin-4-one (4a, 4b) was described. The structures of 4a and 4b were determined by elemental analyses, IR, 1H NMR and X-ray diffraction. In the crystals of compounds 4a and 4b, the imidazole ring and two benzene rings are planar. Interestingly, the dihedral angle between two benzene rings is 71.5° in 4a, while it is almost perpendicular in 4b due to the different benzene substituents. Meanwhile, the thiazolidinone ring is planar in 4a while slightly distorted with an r.m.s deviation of 0.1494(2) A in 4b. The hydrogen bonding interactions observed link the molecules to form a dimeric unit, which may be effective in the stabilization of the structure.

  14. A series of coordination polymers constructed from flexible bis(benzimidazole)ether ligands and different carboxylates

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    Six new coordination polymers constructed from two structurally related ligands, 2,2′-bis(2-methylbenzimidazole)ether (L1) and 2,2′-bis(2-ethylbenzimidazole)ether (L2), have been synthesized. They are [Cu(L1)(bz)2] (1), [Cu(L2)(bz)2] (2), [Zn2(L1)(m-bdc)2] (3), [Cd2(L2)(m-bdc)2(H2O)]2·H2O (4), [Zn(L1)(OH-bdc)-(H2O)] (5) and [Zn2(L2)(btca)] (6), where Hbz = benzoic acid, m-H2bdc = 1,3-benzenedicarboxylic acid, OH-H2bdc = 5-hydroxyisophthalic acid, and H4btca = 1,2,4,5-benzenetetracarboxylic acid. In 1 and 2, the bidentate N-donor ligands (L1 and L2) bridge neighboring metal centers to form 1D single chains. The bz anions are attached on both sides of the chains. In 3 and 4, the N-donor ligands (L1 and L2) in cis conformations bridge two metal centers to generate a [M2(L1)]4+ unit (M = Zn(Ⅱ) and Cd(Ⅱ)). The adjacent [M2(L1)]4+ units are further linked via the dicarboxylate anions to form 1D double chain structures. In 5, the Zn(Ⅱ) cations are bridged by OH-m-bdc anions to form an infinite polymeric chain. The L1 ligands are attached on one side of the chain in a monodentate mode. In 6, two Zn(Ⅱ) cations are bridged by two L2 ligands to form a [ZnL2]24+ ring, which is further linked by btca anions to generate a 2D layer. The luminescent properties of the ligands and 3―6 in the solid state at room temperature were also studied.

  15. A series of coordination polymers constructed from flexible bis(benzimidazole)ether ligands and different carboxylates

    Institute of Scientific and Technical Information of China (English)

    WU Hua; ZHANG LaiPing; LIU HaiYan; YANG Jin; MA JianFang

    2009-01-01

    Six new coordination polymers constructed from two structurally related ligands,2,2'-bis(2-methylbenzimidazole)ether (L1) and 2,2'-bis(2-ethylbenzimidazole)ether (L2),have been synthesized.They are (H2O)](5) and [Zn2(L2)(btca)](6),where Hbz-benzoic acid,m-H2bdc = 1,3-benzenedicarboxylic acid,OH-H2bdc = 5-hydroxyisophthalic acid,and H4btca = 1,2,4,5-benzenetetracarboxyllc acid.In 1 and 2,the bidentate N-donor ligands (L1 and L2) bridge neighboring metal centers to form 1D single chains.The bz anions are attached on both sides of the chains.In 3 and 4,the N-donor ligands (L1 and L2) in cis conformations bridge two metal centers to generate a [M2(L1)]4+ unit (M = Zn(Ⅱ) and Cd(Ⅱ)).The adjacent [M2(L1)]4+ units are further linked via the dicarboxylate anions to form 1D double chain structures.In 5,the Zn(Ⅱ) cations are bridged by OH-m-bdc anions to form an infinite polymeric chain.The L1 ligands are attached on one side of the chain in a monodentate mode.In 6,two Zn(Ⅱ) cations are bridged by two L2 ligands to form a [ZnL2]=4+ ring,which is further linked by btca anions to generate a 2D layer.The luminescent properties of the ligands and 3-6 in the solid state at room temperature were also studied.

  16. Design, synthesis and biological activity of some novel benzimidazole derivatives against Coxsackie virus B3

    Institute of Scientific and Technical Information of China (English)

    Zhong Lv Zhang; Zhi Jie Sun; Fei Xue; Xian Jin Luo; Nai Yun Xiu; Li Teng; Zong Gen Peng

    2009-01-01

    A series of novel benzirnidazole derivatives was synthesized and their anti-Coxsackie virus B3 (CVB3) activity was evaluated in VERO cells. Compounds 9 and 10 exhibited better inhibitory activity than those of ribavirin (RBV) with IC50 values of 5.30 and 1.06 μg/mL, respectively.

  17. Ethyl 1-sec-butyl-2-(4-methoxyphenyl-1H-benzimidazole-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Natarajan Arumugam

    2010-04-01

    Full Text Available In the title molecule, C21H24N2O3, the dihedral angle between the benzene and imidazole rings is 66.33 (13°. The imidazole ring is essentially planar, with a maximum deviation of 0.004 (2 Å. In the crystal structure, molecules are connected by weak C—H...O hydrogen bonds, forming chains along the b axis

  18. Copper Corrosion Inhibition in 1 M HNO3 by Two Benzimidazole Derivatives

    OpenAIRE

    Niamien, P. M.; Kouassi, H. A.; Trokourey, A.; Essy, F. K.; D. Sissouma; Bokra, Y.

    2012-01-01

    Corrosion behavior of copper in 1 M nitric acid containing either 2-mercaptobenzimidazole (MBI) or 2-thiomethylbenzimidazole (TMBI) was investigated experimentally and theoretically via weight loss method and quantum chemical approaches. It was found that the two compounds exhibit a very good performance as inhibitors for copper corrosion in the studied medium. Results show that the inhibition efficiencies increase with increasing temperature and increasing concentration of the inhibitors. It...

  19. Resistência a benzimidazóis por Guignardia citricarpa Guignardia citricarpa resistance to benzimidazoles

    Directory of Open Access Journals (Sweden)

    Maria Beatriz Calderan Rodrigues

    2007-03-01

    Full Text Available O objetivo deste trabalho foi avaliar a resistência de Guignardia citricarpa aos fungicidas carbendazim e piraclostrobina, por meio de avaliação do crescimento em meio de cultura, decomposição de tecido foliar e produção de corpos de frutificação. Para isso, o fungo G. citricarpa foi isolado de lesões de frutos de laranja (Citrus sinensis, produzidos em área com intensa aplicação de fungicida. Os isolados obtidos foram avaliados quanto à sensibilidade aos fungicidas piraclostrobina e carbendazim, nas dosagens de 0,5, 1 e 2 µg mL-1 de i.a., para se verificar o efeito da pressão de seleção causada pelo uso destes compostos em áreas citrícolas. Embora tenha sido observada redução efetiva no número de estruturas reprodutivas e na decomposição de folhas e frutos infectados com G. citricarpa, após a aplicação dos fungicidas, 7,5% dos isolados avaliados sobre meio de cultura apresentaram resistência a esse fungicida, o que indica que pode ocorrer seleção de isolados resistentes no campo. Para a piraclostrobina não foi observada resistência, o que indica que pode ser um composto alternativo para ser utilizado de forma alternada com carbendazim, para diminuir as chances de ocorrência de resistência do patógeno.The objective of this work was to evaluate the resistance of Guignardia citricarpa to pyraclostrobine and carbendazim fungicides, through: growth analysis in culture media amended with the fungicides; leaf decomposition; and production of reproductive structures on leaves naturally infected with these fungi. G. citricarpa was isolated from symptomatic fruits of sweet orange (Citrus sinensis cultivated in area with intense fungicide application. The sensibility to fungicides of G. citricarpa isolates was evaluated with pyraclostrobine and carbendazim, in the doses 0.5, 1 e 2 µg mL-1 a.i., to verify the effect of selection pressure caused by continuous use of these compounds. Although, reduction on leaf decomposition and on the number of reproductive structures were observed after application of pyraclostrobine and carbendazim, 7.5% of the isolates, evaluated in culture media, exhibited resistance to carbendazim, suggesting that the use of this agrochemical must be combined to other active principles in a consortium to reduce the chances of resistance occurrence. No resistance to pyraclostrobine was observed among tested isolates, what indicates that this could be an alternative compound to be used in combination to carbendazim, to minimize the chance of resistance occurrence.

  20. Sulfonated copolyimide membranes derived from a novel diamine monomer with pendant benzimidazole groups for fuel cells

    DEFF Research Database (Denmark)

    Li, Wei; Guo, Xiaoxia; Aili, David;

    2015-01-01

    Sulfonated polyimides are among the most interesting proton exchange membrane materials with high proton conductivity and good mechanical characteristics. As a major challenge the hydrolytic instability of the polymer backbone is addressed by introducing basic moieties in the polymer main chain......(4-aminophenoxy)biphenyl-3,3'-disulfonic acid (BAPBDS) at different diamine molar ratios (BAPBDS/BIPOB, 4/1, 6/1, 9/1 and 12/1). With ion exchange capacities in the range of 1.60-2.24 meq g(-1), transparent and ductile membranes are obtained by solution casting. The incorporation of benzimiclazole...

  1. Antimicrobial Studies of N-Heterocyclic Carbene Silver Complexes Containing Benzimidazol-2-ylidene Ligand

    Directory of Open Access Journals (Sweden)

    Yetkin Gök

    2014-01-01

    Full Text Available Seven novel 4-vinylbenzyl substituted N-heterocyclic carbene (NHC silver complexes were synthesized from different benzimidazolium salts and silver (I oxide in dichloromethane at room temperature. These new 4-vinylbenzyl substituted NHC silver complexes were characterized by spectroscopic (NMR, IR and elemental analysis techniques. Using the agar dilution procedure, the antimicrobial activities of these synthesized new compounds were investigated against Gram (+/(− bacterial and fungal strains. These NHC silver complexes showed effective activities against Escherichia coli, Pseudomonas aeruginosa (Gram-negative bacterial strains, Enterococcus faecalis, Staphylococcus aureus (Gram-positive bacterial strains, and Candida tropicalis and Candida albicans (fungal strains.

  2. Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity

    OpenAIRE

    Ouahrouch, Abdelaaziz; Ighachane, Hana; Taourirte, Moha; Joachim W. Engels; Sedra, My Hassan; Lazrek, Hassan B.

    2014-01-01

    A novel series of hybrid molecules 4a–i and 5a–i were prepared by condensation of 4-(trimethylsilylethynyl)benzaldehyde 1 with substituted o-phenylenediamines. These in turn were reacted with 2-(azidomethoxy)ethyl acetate in a Cu alkyne–azide cycloaddition (CuAAC) to generate the 1,2,3-triazole pharmacophore under microwave assistance. The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and the phytopathoge...

  3. Highly Potent, Water Soluble Benzimidazole Antagonist for Activated (alpha)4(beta)1 Integrin

    Energy Technology Data Exchange (ETDEWEB)

    Carpenter, R D; Andrei, M; Lau, E Y; Lightstone, F C; Liu, R; Lam, K S; Kurth, M J

    2007-08-29

    The cell surface receptor {alpha}{sub 4}{beta}{sub 1} integrin, activated constitutively in lymphoma, can be targeted with the bisaryl urea peptidomimetic antagonist 1 (LLP2A). However, concerns on its preliminary pharmacokinetic (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzimidazole moiety resulting in improved solubility while maintaining picomolar potency [5 (KLCA4); IC{sub 50} = 305 pM]. With exceptional solubility, this finding has potential for improving PK to help diagnose and treat lymphomas.

  4. 2-(2-Hydroxy-3-methoxyphenyl-1H-benzimidazol-3-ium perchlorate

    Directory of Open Access Journals (Sweden)

    Chuan Chen

    2012-06-01

    Full Text Available In the title molecular salt, C14H13N2O2+·ClO4−, the ring systems in the cation are almost coplanar [dihedral angle = 5.53 (13°]. Intramolecular N—H...O and O—H...O hydrogen bonds generate S(6 and S(5 rings, respectively. In the crystal, the two H atoms involved in the intramolecular hydrogen bonds also participate in intermolecular links to acceptor O atoms of the perchlorate anions. A simple intermolecular N—H...O bond also occurs. Together, these form a double-chain structure along [101].

  5. Design, synthesis and computational validation of novel benzimidazole/indole-based PPARα and PPARγ partial agonists

    Indian Academy of Sciences (India)

    Raman K Verma; Prithwish Ghosh; Vijay Kumar; Lalit K Wadhwa

    2013-11-01

    The design and synthesis of benzimidazolyl and indolyl linked -alkoxy phenylpropanoic acid derivatives and the -keto ester analogues in an effort to develop novel peroxisome proliferator activated receptors ligands expected to exhibit PPAR and PPAR partial agonism in the management of hyperglycemia and hyperlipidemia for the treatment of type 2 diabetes is reported. Computational validation of the designed molecules through activity prediction and docking studies showed expected results.

  6. Synthesis and Antibacterial Evaluation of Some Novel Imidazole and Benzimidazole Sulfonamides

    Directory of Open Access Journals (Sweden)

    Aidil Abdul Hamid

    2013-09-01

    Full Text Available Several new substituted sulfonamide compounds were synthesized and their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR, and mass spectroscopy. The antibacterial activities of the synthesized compounds were screened against standard strains of six Gram positive and four Gram negative bacteria using the microbroth dilution assay. Most of the compounds studied showed promising activities against both types of bacteria.

  7. Synthesis and Antibacterial Evaluation of Some Novel Imidazole and Benzimidazole Sulfonamides

    OpenAIRE

    Aidil Abdul Hamid; Taha, Ekhlass M.; Zanariah Abdullah; Raied M. Shakir; Yatimah Alias; Al-Mohammed, Nassir N.

    2013-01-01

    Several new substituted sulfonamide compounds were synthesized and their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR, and mass spectroscopy. The antibacterial activities of the synthesized compounds were screened against standard strains of six Gram positive and four Gram negative bacteria using the microbroth dilution assay. Most of the compounds studied showed promising activities against both types of bacteria.

  8. Hydrogen bonding controlled catalysis of a porous organic framework containing benzimidazole moieties

    KAUST Repository

    Liu, Bing

    2014-01-01

    A microporous organic framework (JUC-Z12) was synthesized quantitatively from tetra(4-formylphenyl)methane and 3,3′-diaminobenzidine. JUC-Z12 shows high thermal stability (>400 °C), a large surface area (SBET = 750 m2 g-1), a well-defined uniform micropore distribution (1.09 nm) and high Qst for H2 (-8.1 kJ mol-1), CO2 (-29.5 kJ mol-1), and CH 4 (-22.2 kJ mol-1). It also exhibits selective catalytic activities in the Knoevenagel reaction, which is supposed to be controlled by hydrogen bonding between substrates and JUC-Z12. The JUC-Z12 catalyst can be easily isolated from the reaction mixture by simple filtration and reused with high activity. This journal is © the Partner Organisations 2014.

  9. Use of P-glycoprotein gene probes to investigate anthelmintic resistance in Haemonchus contortus and comparison with Onchocerca volvulus

    NARCIS (Netherlands)

    Kwa, M.S.G.; Okoli, M.N.; Schulz-Key, H.; Okongkwo, P.O.; Roos, M.H.

    1998-01-01

    A P-glycoprotein gene probe from the sheep parasitic nematode Haemonchus contortus was developed and used to analyse restriction fragment length polymorphisms between susceptible isolates and isolates resistant to either benzimidazole; levamisole and benzimidazole; or benzimidazole, ivermectin and c

  10. 2-Methyl­benzimidazolium thio­cyanate–2-methyl­benzimidazole (1/1)

    OpenAIRE

    A. Shaker, Shayma; Khaledi, Hamid; Mohd Ali, Hapipah

    2010-01-01

    In the crystal structure of the title compound, C8H9N2 +·SCN−·C8H8N2, the three components are linked by inter­molecular N—H⋯N and N—H⋯S hydrogen bonds into infinite chains along the c axis.

  11. 2-(Furan-2-yl-1,3-bis(furan-2-ylmethyl-1H-benzimidazol-3-ium chloride monohydrate

    Directory of Open Access Journals (Sweden)

    David K. Geiger

    2012-10-01

    Full Text Available The title hydrated salt, C21H17N2O3+·Cl−·H2O, exhibits disorder in one of the furan rings. The major and minor components have a refined occupancy ratio of 0.844 (19:0.156 (19. The structure displays intermolecular hydrogen bonding involving the water molecule and the chloride anion. Close intermolecular C—H...Cl and C—H...(furan ring interactions complete the hydrogen bonding.

  12. A novel promising biomolecule immobilization matrix: synthesis of functional benzimidazole containing conducting polymer and its biosensor applications.

    Science.gov (United States)

    Uzun, Sema Demirci; Unlu, Naime Akbasoglu; Sendur, Merve; Kanik, Fulya Ekiz; Timur, Suna; Toppare, Levent

    2013-12-01

    In order to construct a robust covalent binding between biomolecule and immobilization platform in biosensor preparation, a novel functional monomer 4-(4,7-di(thiophen-2-yl)-1H-benzo[d]imidazol-2-yl)benzaldehyde (BIBA) was designed and successfully synthesized. After electropolymerization of this monomer, electrochemical and spectroelectrochemical properties were investigated in detail. To fabricate the desired biosensor, glucose oxidase (GOx) was immobilized as a model enzyme on the polymer coated graphite electrode with the help of glutaraldehyde (GA). During the immobilization step, an imine bond was formed between the free amino groups of enzyme and aldehyde group of polymer. The surface characterization and morphology were investigated to confirm bioconjugation by X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM) at each step of biosensor fabrication. The optimized biosensor shows good linearity between 0.02mM and 1.20mM and a low limit of detection (LOD) of 2.29μM. Kinetic parameters Km(app) and Imax were determined as 0.94mM and 10.91μA, respectively. The biosensor was tested for human blood serum samples. PMID:23973906

  13. A benzimidazole derivative small molecule 991 enhances AMPK activity and glucose uptake induced by AICAR or contraction in skeletal muscle

    DEFF Research Database (Denmark)

    Bultot, Laurent; Jensen, Thomas Elbenhardt; Lai, Yu-Chiang;

    2016-01-01

    AMP-activated protein kinase (AMPK) plays diverse roles and coordinates complex metabolic pathways for maintenance of energy homeostasis. This could be explained by the fact that AMPK exists as multiple heterotrimer complexes comprising a catalytic α subunit (α1, α2) and regulatory β (β1, β2) and...... treatments. The study demonstrates a utility of dual activator approach to achieve a greater activation of AMPK and downstream physiological responses in various cell types including skeletal muscle....

  14. Determination of the geometry change of benzimidazole upon electronic excitation from a combined Franck-Condon/rotational constants fit

    Science.gov (United States)

    Stuhlmann, Benjamin; Gmerek, Felix; Krügler, Daniel; Schmitt, Michael

    2014-08-01

    Single vibronic level fluorescence spectra of the electronic origin and of seven vibronic bands between 0,0 and 0,0 + 1265 cm-1 have been measured and analyzed by means of a combined Franck-Condon/rotational constants fit. The rotational constants in ground and lowest electronically excited singlet state of four different isotopologues have been taken from previous rotationally resolved measurements of Schmitt et al. (2006). The intensities of 182 vibronic emission bands and of 8 rotational constants have been used for a fit of the complete heavy atom geometry changes upon electronic excitation. Vibronic modes, about 1000 cm-1 above the electronic origin, show strong deviations from Franck-Condon behavior in emission. Herzberg-Teller coupling contributes to this effect. 1300 cm-1 above the origin, we observe the onset of intramolecular vibrational redistribution in the emission spectra.

  15. catena-Poly[[[2-(2-pyridyl-1H-benzimidazole]cadmium(II]-μ-benzene-1,4-dicarboxylato

    Directory of Open Access Journals (Sweden)

    Hong-Mei Sun

    2009-08-01

    Full Text Available In the title compound, [Cd(C8H4O4(C12H9N3]n, each CdII ion is six-coordinated in a distorted octahedral geometry by four carboxylate O atoms from two benzene-1,4-dicarboxylate anions (L, and two N atoms from one 2-(2-pyridylbenzimidazole ligand. The neighboring CdII ions are bridged by the L ligands, forming a zigzag polymeric chain structure. The chains are further extended into a three-dimensional supramolecular structure through intermolecular N—H...O hydrogen bonds.

  16. Structural modulation of Co(II) coordination polymers with flexible bis(benzimidazole) and different dicarboxylate ligands

    Science.gov (United States)

    Qin, Li; Wang, Li-na; Ma, Pei-juan; Cui, Guang-hua

    2014-02-01

    Two complexes [Co2(L)2(npht)2·H2O]n (1) and [Co(L)(mip)·0.5H2O]n (2) (H2npht = 3-nitrophthalic acid, L = 1,3-bis(5,6-dimethylbenzimidazol)propane, H2mip = 5-methylisophthalic acid) were obtained under hydrothermal conditions. In compound 1, two npht2- ligands connect two crystallographically independent Co atoms to form a binuclear [Co2(npht)]2 subunit, further linked by L ligands to generate a 1D ladder-like chain, which is arranged into a 2D supramolecular layer through face-to-face π-π stacking interactions. Compound 2 exhibits a 2D 4-connected coordination network. The fluorescence properties of 1 and 2 have been investigated in the solid-state. Both complexes show higher catalytic behaviors for degradation of methyl orange dye.

  17. Use of benzimidazole agar plates to assess fall armyworm (Lepidoptera: Noctuidae) feeding on excised maize and sorghum leaves

    Science.gov (United States)

    The fall armyworm, Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae) is an economically significant pest of sorghum and maize. To screen sorghum and maize germplasm for resistance to fall armyworm feeding, field, greenhouse, or lab bioassays are often utilized individually or in combinatio...

  18. A novel promising biomolecule immobilization matrix: synthesis of functional benzimidazole containing conducting polymer and its biosensor applications.

    Science.gov (United States)

    Uzun, Sema Demirci; Unlu, Naime Akbasoglu; Sendur, Merve; Kanik, Fulya Ekiz; Timur, Suna; Toppare, Levent

    2013-12-01

    In order to construct a robust covalent binding between biomolecule and immobilization platform in biosensor preparation, a novel functional monomer 4-(4,7-di(thiophen-2-yl)-1H-benzo[d]imidazol-2-yl)benzaldehyde (BIBA) was designed and successfully synthesized. After electropolymerization of this monomer, electrochemical and spectroelectrochemical properties were investigated in detail. To fabricate the desired biosensor, glucose oxidase (GOx) was immobilized as a model enzyme on the polymer coated graphite electrode with the help of glutaraldehyde (GA). During the immobilization step, an imine bond was formed between the free amino groups of enzyme and aldehyde group of polymer. The surface characterization and morphology were investigated to confirm bioconjugation by X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM) at each step of biosensor fabrication. The optimized biosensor shows good linearity between 0.02mM and 1.20mM and a low limit of detection (LOD) of 2.29μM. Kinetic parameters Km(app) and Imax were determined as 0.94mM and 10.91μA, respectively. The biosensor was tested for human blood serum samples.

  19. Inhibition of Mild Steel Corrosion in 1M H2SO4 Medium by Benzimidazole Mannich bases

    Directory of Open Access Journals (Sweden)

    P. M. Dasami

    2015-03-01

    Full Text Available The corrosion inhibition behaviour of two synthesized Mannich bases has been investigated for mild steel in 1M H2SO4 by weight loss and electrochemical techniques.The inhibition efficiency depends on concentration of the inhibitor and temperature. The inhibitors function by adsorption on mild steel surface and obey Langmuir isotherm indicating monolayer adsorption on the surface. Thermodynamic parameters show that the adsorption of the inhibitors occurs through electrostatic interaction. Polarization studies reveal that the inhibitors behave as mixed type in 1M H2SO4 affecting both anodic metal dissolution and cathodic hydrogen evolution. SEM studies show the formation of surface adsorptive film of the Mannich bases on the mild steel surface.

  20. Agrobacterium tumefaciens-mediated transformation in the entomopathogenic fungus Lecanicillium lecanii and development of benzimidazole fungicide resistant strains.

    Science.gov (United States)

    Zhang, Yan-Jun; Zhao, Jin-Jin; Xie, Ming; Peng, De-Liang

    2014-10-01

    Lecanicillium lecanii has been used in the biological control of several insects in agricultural practice. Since the gene manipulation tools for this entomopathogenic fungus have not been sufficiently developed, Agrobacterium tumefaciens-mediated transformation (ATMT) in L. lecanii was investigated in this study, using the wild-type isolate FZ9906 as a progenitor strain and the hygromycin B resistance (hph) gene as a selection marker. Furthermore, a field carbendazim-resistant (mrt) gene from Botrytis cinerea was expressed in L. lecanii FZ9906 via the ATMT system. The results revealed that the frequency of transformation surpassed 25transformants/10(6) conidia, most of the putative transformants contained a single copy of T-DNA, and the T-DNA inserts were stably inherited after five generations. All putative transformants had indistinguishable biological characteristics relative to the wild-type strain, excepting two transformants with altered growth habits or virulence. Moreover, the resistance of the putative transformants to carbendazim (MBC) was improved, and the highest one was 380-fold higher than the wild-type strain. In conclusion, ATMT is an effective and suitable system for L. lecanii transformation, and will be a useful tool for the basic and application research of gene functions and gene modifications of this strain. PMID:25107375

  1. Bis[1,3-bis(benzimidazol-2-yl-2-oxapropane]copper(II–picrate–dimethylformamide (1/2/4

    Directory of Open Access Journals (Sweden)

    Huilu Wu

    2008-12-01

    Full Text Available In the title compound, [Cu(C16H14N4O2](C6H2N3O72·4C3H7NO, the CuII ion is located on a crystallographic inversion center and is coordinated in a distorted octahedral environment by four N atoms and two O atoms forming two long Cu—O bonds. One of the unique dimethylformamide solvent molecules is disordered over two sites with occupancies of 0.715 (6 and 0.285 (6. The crystal structure is stabilized by intermolecular N—H...O hydrogen bonds.

  2. In vitro resistance to 5-nitroimidazoles and benzimidazoles in Giardia duodenalis: variability and variation in gene expression.

    Science.gov (United States)

    Argüello-García, Raúl; Cruz-Soto, Maricela; Romero-Montoya, Lydia; Ortega-Pierres, Guadalupe

    2009-12-01

    The susceptibility of Giardia duodenalis trophozoites exposed in vitro to sublethal concentrations of metronidazole (MTZ) and albendazole (ABZ) may exhibit inter-culture (variability) and intra-culture (variation) differences in drug susceptibility. It was previously reported that MTZ-resistant trophozoites may display changes in pyruvate:ferredoxin oxidoreductase (PFOR) expression while changes at the beta-tubulin molecule are apparently absent in ABZ-resistant cultures. To assess the levels of gene expression of these molecules, we obtained cloned cultures growing at concentrations up to 23 microM MTZ (WBRM23) and up to 8muM ABZ (WBRA8) and gene sequence and expression of pfor and beta-tubulin loci were compared with these of drug-susceptible clone WB1. Neither the pfor nor the beta-tubulin genes showed changes at sequence level but the MTZ-resistant clones WBRM21 and WBRM23 showed up-regulation of the pfor RNA using the gdh gene as reference. By using WB1 and WBRA8 clones in representational difference analyses of gene expression (RDA) an insert referred to as ARR-VSP was selected and sequenced. It showed the highest homology to one VSP molecule in the Giardia Genome Database (orf GL50803_101765). This isogene was up-regulated in five ABZ-resistant clones and the clone WBRA8 exhibited the highest RNA expression level. When successive progenies of clones WB1, WBRM23 and WBRA8 were analyzed in Northern blot assays to detect pfor and ARR-VSP RNAs respectively, the expression patterns showed variation for both genes but it was much lower in the clone WBRA8. These results suggest that G. duodenalis cultures either susceptible or resistant to MTZ and ABZ may display variability and variation at RNA expression levels albeit these were more marked in the MTZ-resistant parasites. These data might have further implications defining major mechanisms involved in drug resistance of Giardia. PMID:19481175

  3. Drug: D03623 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available 2C ANTINEMATODAL AGENTS P02CA Benzimidazole derivatives P02CA04 Ciclobendazole D0...3623 Cyclobendazole (USAN); Ciclobendazole (INN) Antiinfectives [BR:br08307] Antiparasitics Antinematodal agents Benzimidazole

  4. Drug: D07106 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available ELLENTS P02 ANTHELMINTICS P02C ANTINEMATODAL AGENTS P02CA Benzimidazole derivativ...thelmintics Albendazole D07106 Albendazole oxide (INN) Antiinfectives [BR:br08307] Antiparasitics Antinematodal agents Benzimidazole

  5. Drug: D04200 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available 03] P ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS P02 ANTHELMINTICS P02C ANTINEMATODAL AGENTS P02CA Benzimidazole...iinfectives [BR:br08307] Antiparasitics Antinematodal agents Benzimidazole derivatives Flubendazole [ATC:P02

  6. Drug: D04140 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available TINEMATODAL AGENTS P02CA Benzimidazole derivatives P02CA06 Fenbendazole D04140 Fe...nbendazole (USP/INN) Antiinfectives [BR:br08307] Antiparasitics Antinematodal agents Benzimidazole derivativ

  7. A fluorescence switch based on a controllable photochromic naphthopyran group

    Energy Technology Data Exchange (ETDEWEB)

    Chen Lizhen [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Wang Guang, E-mail: wangg923@nenu.edu.cn [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Zhao Xiancai [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China)

    2011-08-15

    A fluorescence switch based on photoisomerization of naphthopyran (NP) has been designed by employing 2-(pyridin-2-yl)-benzimidazole (BPI) and the naphthopyran containing two pyran rings (NP) as fluorescent dye and photochromic compound, respectively. The fluorescence switch of benzimidazole derivative can be modulated either by controlling the irradiation time of UV light or by adjusting the amount ratio of fluorescent benzimidazole derivative to photochromic naphthopyran in both solution and polymethyl methacrylate (PMMA) film. The experimental results indicated that the decrease of fluorescence intensity of benzimidazole derivative is attributed to the interaction of benzimidazole with naphthopyran. - Highlights: > Naphthopyran was first used to fabricate fluorescence switch with benzimidazole derivative. > Fluorescence intensity can be modulated by controlling the UV irradiation time. > Fluorescence intensity can be adjusted by changing the ratio of benzimidazole derivative to naphthopyran. > Decrease of fluorescence intensity is attributed to the interaction of benzimidazole derivative and naphthopyran.

  8. Benzimidazole -Resistance in Haemonchus Contortus: New PCR-RFLP Method for the Detection of Point Mutation at Codon 167 of Isotype 1 Β-Tubulin Gene

    Directory of Open Access Journals (Sweden)

    A Eslami

    2012-12-01

    Full Text Available Background: Due to the lack of a suitable and economic test for the analysis of the polymorphism at codon 167, we developed a new PCR-RFLP technique, based on a modified forward primer (UT-HC167 MF-primer, to identify simultaneously the SNPs at codons 167 and 200 of isotype 1 β-tubu­lin gene of Haemonchus contortus.Methods: There already are several safe and easy methods for identification of point mutations at codons 198 and 200. Due to the lack of a reliable and easy method for the detection of the single nucleo­tide polymorphism (SNP at codon 167, we developed an innovative PCR-RFLP technique based on a modified forward primer (UT-HC167 MF-primer, in which the nucleotide T at the posi­tion 443 was substituted through a nucleotide A creating a restriction site for restriction endonuc­lease SnaB I in the nucleotide sequences including codon 167. A total of 138 adult male H. contortus were collected from three different geo-climatic areas of Iran. The isolated genomic DNA of each single worm was amplified by PCR using primers flanking codon 167. The PCR product (527 bp was then amplified by semi-nested PCR using the UT-HC167 MF-primer and the reverse primer achiev­ing a PCR product of 451 bp in length. This PCR product was subsequently digested with the restriction endonucleases SnaB I and TaaI for analysis of the mutations at codons 167 and 200, respec­tively.Results: All worms had two alleles encoding for phenylalanine (BZss homozygote for both codons.Conclusion: Using the UT-HC167 MF-primer and a suitable reverse primer designed upstream from codon 200, it is possible to amplify a PCR product which can be used for analysis of the SNPs at all three mentioned codons using RFLP.

  9. Influence of bulky N-substituents on the formation of lanthanide triple helical complexes with a ligand derived from bis(benzimidazole)pyridine: structural and thermodynamic evidence.

    Science.gov (United States)

    Muller, G; Bünzli, J C; Schenk, K J; Piguet, C; Hopfgartner, G

    2001-06-01

    The planar aromatic tridentate ligand 2,6-bis(1-S-neopentylbenzimidazol-2-yl)pyridine (L(11)) reacts with Ln(III) (Ln = La-Lu) in acetonitrile to give the successive complexes [Ln(L(11))(n)](3+) (n = 1-3). However, stability constants determined by spectrophotometry and NMR titrations show that formation of the tris complexes is not favored, log K(3) being around 1 for La(III) and Eu(III), while no such species could be evidenced for the smaller Lu(III) ion. The X-ray structures of L(11) (monoclinic, P2(1), a = 13.4850(12) A, b = 12.0243(11) A, c = 16.4239(14) A, beta = 103.747(7) degrees ), [La(ClO(4))(2)(L(11))(2)](3)[La(ClO(4))(2)(H(2)O)(L(11))(2)](ClO(4))(4).15MeCN (1a, monoclinic, P2(1), a = 21.765(4) A, b = 30.769(6) A, c = 21.541(5) A, beta = 116.01(3) degrees ), and [Eu(L(11))(3)](ClO(4))(3).4.28MeCN (5a, monoclinic, P1, a = 14.166(3) A, b = 19.212(4) A, c = 21.099(4) A, alpha = 108.91(3) degrees, beta = 98.22(3) degrees, gamma = 108.40(3) degrees ) have been solved. In 1a, two different types of complex cations are evidenced, both containing 10-coordinate La(III) ions. In the first type, both perchlorate anions are bidentate, while in the second type, one perchlorate is monodentate, the 10th coordination position being occupied by a water molecule. In 5a the three ligands are not equivalent. Ligands A and B are wrapped in a helical way and are mirror images of each other, while ligand C lies almost perpendicular to the two other ones. This stems from the steric hindrance generated by the bulky neopentyl groups with the consecutive loss of any stabilizing interstrand pi-stacking interactions. This explains the low stability of the tris complexes and the difficulty of isolating them and points to the importance of the steric factors in the design of self-assembled triple helical lanthanide-containing functional edifices [Ln(L(i))(3)](3+). PMID:11375674

  10. Extended X- ray absorption fine structure study at the K-edge of copper in mixed ligand complexes having benzimidazole as one of the ligands

    Science.gov (United States)

    Hinge, V. K.; Joshi, S. K.; Nitin Nair, N.; Singh Verma, Vikram; Shrivastava, B. D.; Prasad, J.; Srivastava, K.

    2014-09-01

    Extended X-ray absorption fine structure (EXAFS) spectra have been studied at the K-edge of copper in some of its biologically important complexes, viz., [Cu(BzImH)4X2] and [Cu(BzIm)2], where X= Cl, Br, 1/2SO4, ClO4, NO3, and BzIm = Benzimidazolato anion. The spectra have been recorded using a bent crystal 0.4 m Cauchois-type transmission spectrograph. The positions of EXAFS maxima and minima have been used to determine the bond lengths in the complexes with the help of three different methods, namely, Levy's, Lytle's and Lytle, Sayers and Stern's (L.S.S.) methods. The phase uncorrected bond lengths have also been determined from Fourier transforms of the experimental spectra. The results obtained from these methods have been discussed and it has been found that the results obtained by L.S.S. method are comparable with the results obtained by Fourier transformation method and that these two methods give phase uncorrected bond lengths.

  11. Ethyl 2-(4-bromophenyl-1-[3-(1H-imidazol-1-ylpropyl]-1H-benzimidazole-5-carboxylate monohydrate

    Directory of Open Access Journals (Sweden)

    Yeong Keng Yoon

    2011-11-01

    Full Text Available In the title compound, C22H21BrN4O2·H2O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1 and 0.002 (1 Å], and form a dihedral angle of 73.46 (9°. The dihedral angle between the benzene rings is 29.33 (7°. In the crystal, molecules are connected via C—H...O and O—H...N hydrogen bonds, forming layers in the ab plane.

  12. A bifunctional chromogenic and fluorogenic probe for F{sup −} and Al{sup 3+} based on azo-benzimidazole conjugate

    Energy Technology Data Exchange (ETDEWEB)

    Iniya, Murugan; Jeyanthi, Dharmaraj; Krishnaveni, Karuppiah; Chellappa, Duraisamy, E-mail: dcmku123@gmail.com

    2015-01-15

    A versatile bifunctional probe has been reported for selective individual detection of Al{sup 3+} and F{sup −} through “turn-on” chromogenic and fluorogenic dual modes. The photonic behaviors of probe upon addition of analyte have been determined using UV–vis absorption, fluorescence emission, quantum yield and fluorescence life-time measurement. Density functional theory calculations have been performed to establish the nature of interaction between probe and Al{sup 3+}/F{sup −}. - Highlights: • First report on azo based bifunctional chromogenic and fluorogenic chemosensor for Al{sup 3+} and F{sup −} with varied responses. • The probe displays simple method of synthesis, reversibility towards Al{sup 3+} and high stability. • TD–DFT calculations were performed to characterize the nature of fluorescent behavior of probe upon addition of Al{sup 3+} and F{sup −}.

  13. Effect of substituent on structures and catalytic properties of cobalt(II) isophthalate coordination polymers with a semi-rigid bis(benzimidazole)

    Science.gov (United States)

    Zhang, Xu; Meng, Xiang-Li; Huang, Cui-Miao; Cui, Guang-Hua

    2015-11-01

    Three Co(II) coordination polymers based on flexible bis(2-dimethylbenzimidazole) and the derivatives of the familiar isophthalate co-ligands, namely [Co(L)(ip)]n (1), [Co2(L)2(nip)2]n (2) and [Co2(L)2(tbip)2·2H2O]n (3) (L = 1,2-bis(2-methylbenzimidazol-1-ylmethyl)benzene, H2ip = isophthalic acid, H2nip = 5-nitroisophthalic acid, H2tbip = 5-tert-butylisophthalic acid) have been synthesized by hydrothermal methods and characterized by elemental analyses, IR spectra, thermogravimetric analyses and single-crystal X-ray diffraction. Both complexes 1 and 2 exhibit a 2-fold interpenetrating 3D network with 66-dia topology, whereas complex 3 is bridged by the L and tbip2- ligands to form a rarely tri-nodal (3,3,5) layer with 3,3,5L18 topology. The results indicate that Co(II) mixed coordination polymers structurally modulated by the substituent effect of isophthalate-involved co-ligands. In addition, the fluorescence and catalytic activity of the complexes for the degradation of methyl orange by the sodium persulfate in a Fenton-like process have been investigated.

  14. Radioiodinated benzimidazole derivatives as single photon emission computed tomography probes for imaging of {beta}-amyloid plaques in Alzheimer's disease

    Energy Technology Data Exchange (ETDEWEB)

    Cui Mengchao [Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan); Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875 (China); Ono, Masahiro, E-mail: ono@pharm.kyoto-u.ac.j [Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan); Kimura, Hiroyuki; Kawashima, Hidekazu [Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan); Liu Boli [Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875 (China); Saji, Hideo, E-mail: hsaji@pharm.kyoto-u.ac.j [Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501 (Japan)

    2011-04-15

    Five iodinated 2-phenyl-1H-benzo[d]imidazole derivatives were synthesized and evaluated as potential probes for {beta}-amyloid (A{beta}) plaques. One of the compounds, 4-(6-iodo-1H-benzo[d]imidazol-2-yl)-N,N-dimethylaniline (12), showed excellent affinity for A{beta}{sub 1-42} aggregates (K{sub i}=9.8 nM). Autoradiography with sections of postmortem Alzheimer's disease (AD) brain revealed that a radioiodinated probe [{sup 125}I]12, labeled A{beta} plaques selectively with low nonspecific binding. Biodistribution experiments with normal mice injected intravenously with [{sup 125}I]12 showed high uptake [4.14 percent injected dose per gram (% ID/g) at 2 min] into and rapid clearance (0.15% ID/g at 60 min) from the brain, which may bring about a good signal-to-noise ratio and therefore achieve highly sensitive detection of A{beta} plaques. In addition, [{sup 125}I]12 labeled amyloid plaques in vivo in an AD transgenic model. The preliminary results strongly suggest that [{sup 125}I]12 bears characteristics suitable for detecting amyloid plaques in vivo. When labeled with {sup 123}I, it may be a useful SPECT imaging agent for A{beta} plaques in the brain of living AD patients.

  15. Octacarbonyl(5-methoxy-2,3-dihydro-1H-benzimidazol-2-yldi-μ3-sulfido-diiron(Iiron(II(2 Fe—Fe

    Directory of Open Access Journals (Sweden)

    Tingting Zhang

    2008-01-01

    Full Text Available The title compound, [Fe3(C8H8N2OS2(CO8], was prepared by the direct reaction of Fe3(CO12 and 5-methoxy-1H-benzoimidazole-2-thiol in tetrahydrofuran. Desulfurization took place readily to form a sulfide carbonyl cluster. The molecule contains a triangle consisting of three Fe atoms capped by two S atoms above and below. There are two Fe—Fe bonds [2.6322 (5 and 2.5582 (5 Å] in the triangle; the length of the third edge [3.3987 (5 Å] is too long to represent an Fe—Fe bond.

  16. Synthesis of Poly[2,2'-(m-phenylene)-5,5'-bibenzimidazole]and Poly(2,5-benzimidazole)by Microwave Irradiation

    Institute of Scientific and Technical Information of China (English)

    HE Rong-huan; SUN Bao-ying; YANG Jing-shuai; CHE Quan-tong

    2009-01-01

    or PBI,and 0.6480 dL/g for ab-PBI,respectively.Characterization of the polymer products was made by nuclear magnetic resonance(1H NMR),Fourier transform infrared spectra(FTIR)and thermogravimetrjc analysis(TGA).

  17. Synthesis, characterization, reactivity and catalytic activity of oxidovanadium(IV), oxidovanadium(V) and dioxidovanadium(V) complexes of benzimidazole modified ligands.

    Science.gov (United States)

    Maurya, Mannar R; Bisht, Manisha; Kumar, Amit; Kuznetsov, Maxim L; Avecilla, Fernando; Pessoa, João Costa

    2011-07-14

    The reaction between [V(IV)O(acac)(2)] and the ONN donor Schiff base obtained by the condensation of pyridoxal and 2-aminoethylbenzimidazole (Hpydx-aebmz, I) or 2-aminomethylbenzimidazole (Hpydx-ambmz, II) in equimolar amounts results in the formation of [V(IV)O(acac)(pydx-aebmz)] 1 and [V(IV)O(acac)(pydx-ambmz)] 2, respectively. The aerobic oxidation of the methanolic solution of 1 yielded [V(V)O(2)(pydx-aebmz)] 3 and its reaction with aqueous H(2)O(2) gave the oxidoperoxidovanadium(v) complex, [V(V)O(O(2))(pydx-aebmz)] 4. The formation of 4 in solution is also established by titrations of methanolic solutions of 1 with H(2)O(2). By titrating solutions of 3 and of 4 with aqueous H(2)O(2) several distinct V(V)-pydx-aebmz species also containing the peroxido ligand are detected. The full geometry optimization of all species envisaged was done using DFT methods for suitable model complexes. The (51)V NMR chemical shifts (δ(V)) have also been calculated, the theoretical data being used to support assignments of the experimental chemical shifts. The (51)V hyperfine coupling constants are calculated for 1, the obtained values being in good agreement with the experimental EPR data. Reaction between the V(IV)O(2+) exchanged zeolite-Y and Hpydx-aebmz and Hpydx-ambmz in refluxing methanol, followed by aerial oxidation results in the formation of the encapsulated V(V)O(2)-complexes, abbreviated herein as [V(V)O(2)(pydx-aebmz)]-Y 5 and [V(V)O(2)(pydx-ambmz)]-Y 6. The molecular structure of 1, determined by single crystal X-ray diffraction, confirms its distorted octahedral geometry with the ONN binding mode of the tridentate ligand, with one acetylacetonato group remaining bound to the V(IV)O-centre. Oxidation of styrene is investigated using some of these complexes as catalyst precursors with H(2)O(2) as oxidant. Under optimised reaction conditions for the conversion of styrene in acetonitrile, a maximum of 68% conversion of styrene (with [V(V)O(2)(pydx-aebmz)]-Y) and 65% (with [V(V)O(2)(pydx-ambmz)]-Y) is achieved in 6 h of reaction time. The selectivity of the various products is similar for both catalysts and follows the order: benzaldehyde (ca. 55%) > 1-phenylethane-1,2-diol > benzoic acid > styrene oxide > phenyl acetaldehyde. Speciation of the systems and plausible intermediates involved in the catalytic oxidation processes are established by UV-Vis, EPR, (51)V NMR and DFT studies. Both non-radical (Sharpless) and radical mechanisms of the olefin oxidations were theoretically studied, and the radical pathway was found to be even more favorable than the Sharpless mechanism. PMID:21647507

  18. Resistance of Colletotrichum gloeosporioides to Benzimidazole Fungicide Carbendazim in Camellia oleifera Nurseries%油茶苗圃炭疽病菌抗药性研究

    Institute of Scientific and Technical Information of China (English)

    李河; 周国英; 章怀云; 刘君昂; 彭宽

    2012-01-01

    The fungicide resistance of anthracnose in Camellia oleifera nurseries was investigated in Liuyang,Changning,and other regions in Hunan Province.The Colletotrichum gloeosporioides strains from the former two regions were highly resistant to carbendazim.After subcultured for 10 generations on fungicide-free medium,the resistant strains grew well on the medium containing carbendazim 450 μg/mL and suggesting that its resistance was stable.The β-tubulin genes from the resistant and susceptible strains were cloned and sequenced.The coding region was 1 344 bp nucleotides and predicted to encode a protein with 447 amino acids.Comparison of the β-tubulin amino acid sequences between resistant and susceptible strains of Colletotrichum gloeosporioides revealed that a mutation leading to an amino acid substitution at the position 198 from glutamic acid in the susceptible strain to alanine in the resistant strain.Finally,the main morphological characteristics of C.gloeosporioides were descripted,but it could not be used to determine the resistance to carbendazim.

  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. [Research of imidazo[1,2-a]benzimidazole derivatives. XXX. Synthesis and properties of (imidazo[1,2-a]benzimidazolyl-2)acetic acid derivatives].

    Science.gov (United States)

    Anisimova, V A; Tolpygin, I E; Spasov, A A; Serdiuk, T S; Sukhov, A G

    2011-01-01

    Ethyl esters of (9-subtituted-imidazo[1,2-a]benzimidazolyl-2)acetic acids were synthesized. The chemical properties of these esters (hydrolysis, decarboxylation, hydrazinolysis) and biological activity (fungicidal, antimicrobial, antiarrhythmic activity, and also affects on the brain rhythmogenesis) of the prepared compounds were studied.