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

DIR@IMTECH: CSIR-Institute of Microbial Technology

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Title Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2-a]pyridine based organoselenium compounds
 
Creator Kumar, Sanjeev
Sharma, Nidhi
Maurya, Indresh K.
Bhasin, Aman K.K.
Wangoo, Nishima
Brandão, Paula
Félix, Vítor
Bhasin, K.K.
Sharma, Rohit K.
 
Subject QR Microbiology
 
Description A simple and efficient method has been described to synthesize the hitherto unknown imidazo[1,2-a]pyridine selenides (5a-l) 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.
 
Publisher Scientifiques Elsevier
 
Date 2016
 
Type Article
PeerReviewed
 
Relation http://dx.doi.org/10.1016/j.ejmech.2016.07.076
http://crdd.osdd.net/open/1972/
 
Identifier Kumar, Sanjeev and Sharma, Nidhi and Maurya, Indresh K. and Bhasin, Aman K.K. and Wangoo, Nishima and Brandão, Paula and Félix, Vítor and Bhasin, K.K. and Sharma, Rohit K. (2016) Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2-a]pyridine based organoselenium compounds. European Journal of Medicinal Chemistry, 123. pp. 916-924. ISSN 02235234