Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2-a]pyridine based organoselenium compounds
authors Kumar, S; Sharma, N; Maurya, IK; Bhasin, AKK; Wangoo, N; Brandao, P; Felix, V; Bhasin, KK; Sharma, RK
nationality International
journal EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
keywords BIOLOGICAL EVALUATION; DIORGANYL SELENIDES; ANTIFUNGAL ACTIVITY; ANTIVIRAL ACTIVITY; ANTICANCER AGENTS; ALKYL-HALIDES; SE; DISELENIDES; DERIVATIVES; SELENOCYSTEINE
abstract A simple and efficient method has been described to synthesize the hitherto unknown imidazo[1,2-a] pyridine selenides (5a-1) by reaction of 2-chloroimidazo [1,2-a]pyridines with aryl/heteroaryl selenols, generated in situ by reduction of various diselenides with hypophosphorous acid. The crystal structures of 3-nitro-2-(phenylselanyl)-imidazo[1,2-a]pyridine (5a), 2-(mesitylselanyl)-3-nitro-imidazo[1,2-a]pyridine (5d) and 3-nitro-2-(pyridin-2-ylselanyl)-imidazo[1,2-a]pyridine (5e) were confirmed by X-ray crystallography and the DFT calculations were performed to determine various structural parameters which were correlated with the X-ray crystal structures. The synthesized compounds were subjected to antimicrobial evaluation and it was found that compounds 5a and 5j were active against gram negative bacterium Escherichia coli whereas compound 5e was active against different fungal strains. Time kill assay was performed to understand the microbial activity of synthesized organoselenium compounds and the toxicity of these compounds was evaluated against human cell lines. Synergistic effects of active compounds 5a and 5e were tested with existing antibiotic drugs which exhibited that the antibiotic combination with synthesized organoselenium compounds efficiently enhanced the antimicrobial activity. (C) 2016 Elsevier Masson SAS. All rights reserved.
publisher ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
issn 0223-5234
year published 2016
volume 123
beginning page 916
ending page 924
digital object identifier (doi) 10.1016/j.ejmech.2016.07.076
web of science category Chemistry, Medicinal
subject category Pharmacology & Pharmacy
unique article identifier WOS:000385319000072
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