96954-35-7Relevant articles and documents
Synthesis, bioevaluation and docking studies of some 2-phenyl-1H-benzimidazole derivatives as anthelminthic agents against the nematode Teladorsagia circumcincta
Escala, Nerea,Valderas-García, Elora,Bardón, María álvarez,Gómez de Agüero, Verónica Castilla,Escarcena, Ricardo,López-Pérez, José Luis,Rojo-Vázquez, Francisco A.,San Feliciano, Arturo,Bala?a-Fouce, Rafael,Martínez-Valladares, María,Olmo, Esther del
, (2020/10/02)
Gastrointestinal nematode infections are the main diseases in herds of small ruminants. Resistance to the main established drugs has become a worldwide problem. The purpose of this study is to obtain and evaluate the in vitro ovicidal and larvicidal activity of some 2-phenylbenzimidazole derivatives on susceptible and resistant strains of Teladorsagia circumcincta. Compounds were prepared by known procedures from substituted o-phenylenediamines and arylaldehydes or intermediate sodium 1-hydroxyphenylmethanesulfonate derivatives. Egg Hatch Test (EHT), Larval Mortality Test (LMT) and Larval Migration Inhibition Test (LMIT) were used in the initial screening of compounds at 50 μM concentration, and EC50 values were determined for the most potent compounds. Cytotoxicity evaluation of compounds was conducted on human Caco-2 and HepG2 cell lines to calculate their Selectivity Indexes (SI). At 50 μM concentration, nine out of twenty-four compounds displayed more than 98% ovicidal activity on a susceptible strain, and four of them showed more than 86% on one resistant strain. The most potent ovicidal benzimidazole (BZ) 3 showed EC50 = 6.30 μM, for the susceptible strain, while BZ 2 showed the lowest EC50 value of 14.5 μM for the resistant strain. Docking studies of most potent compounds in a modelled Teladorsagia tubulin indicated an inverted orientation for BZ 1 in the colchicine binding site, probably due to its fair interaction with glutamic acid at codon 198, which could justify its inactivity against the resistant strain of T. circumcincta.
Synthesis of new TCH/Ni-based nanocomposite supported on SBA-15 and its catalytic application for preparation of benzimidazole and perimidine derivatives
Kalhor, Mehdi,Rezaee-Baroonaghi, Fahimeh,Dadras, Akbar,Zarnegar, Zohre
, (2019/03/21)
A stable nickel-decorated SBA-15 nanocomposite (Ni/TCH@SBA-15) was synthesized through surface modification of silica nanoparticles with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) followed by metal–ligand coordination with Ni (II). The structure of this organometallic nanocomposite was characterized by Fourier transform-infrared, field emission-scanning electron microscopy, EDAX, transmission electron microscopy, atomic absorption spectroscopy and N2 adsorption–desorption (Brunauer–Emmett–Teller) techniques. The catalytic performance of Ni/TCH@SBA-15 (NNTS-15) was determined for the synthesis of 2-aryl-substituted benzimidazoles and 2,3-dihydroperimidines. The excellent yields within shorter reaction times, simplicity of catalytic methods, non-toxicity and clean reactions, mild reaction conditions and easy work-up procedure are the important merits of these synthetic protocols. Moreover, the Ni (II) bonded to the SBA-15 surface was stable under the catalytic reaction conditions resulting in its efficient recycling and reuse.
Mild, one-pot preparation of 2-substituted benzimidazoles from organic halides
Br?tulescu, George
supporting information, p. 811 - 817 (2017/04/06)
Alkyl halides are feasibly transformed into benzimidazoles by a domino reaction under solvent-free conditions. The organic halides react with o-phenylenediamines in stoichiometric amounts in the presence of pyridine-N-oxide to produce the desired substituted benzimidazoles. This domino synthesis does not require catalysts. The synthesis occurs in dry medium and the environmental impact is minimal. The method provides products without intermediate separation. A mechanism of benzimidazole synthesis is also proposed.
