Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2-a]pyridine based organoselenium compounds

resumo

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.

palavras-chave

BIOLOGICAL EVALUATION; DIORGANYL SELENIDES; ANTIFUNGAL ACTIVITY; ANTIVIRAL ACTIVITY; ANTICANCER AGENTS; ALKYL-HALIDES; SE; DISELENIDES; DERIVATIVES; SELENOCYSTEINE

categoria

Pharmacology & Pharmacy

autores

Kumar, S; Sharma, N; Maurya, IK; Bhasin, AKK; Wangoo, N; Brandao, P; Felix, V; Bhasin, KK; Sharma, RK

nossos autores

agradecimentos

This work is supported by Science and Engineering Research Board (SERB), India (grant no. SB/SO/BB/0040/2013), Department of Science and Technology-PURSE (DST-PURSE), India, iBiMED-Institute of Biomedicine (FCT Ref. UID/BIM/04501/2013) and CICECO-Aveiro Institute of Materials (FCT Ref. UID/CTM/50011/2013). KKB is grateful to Council of Scientific and Industrial Research (CSIR), India for Emertius Scientist award no. 21(0967)/13/EMR II. SIC and NS thank CSIR, India for their research fellowships (grant no. 09/135/(0674)/2012/EMR I and 09/135/(0675)/2012/EMR I).

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