A one pot synthesis of novel bioactive tri- substitute-condensed-imidazopyridines that targets snake venom phospholipase A<inf>2</inf>

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Anilkumar, N.C. and Sundaram, M.S. and Mohan, C.D. and Rangappa, S. and Bulusu, K.C. and Fuchs, J.E. and Girish, K.S. and Bender, A. and Basappaa, . and Rangappa, K.S. (2015) A one pot synthesis of novel bioactive tri- substitute-condensed-imidazopyridines that targets snake venom phospholipase A<inf>2</inf>. PLoS ONE, 10 (7). ISSN 19326203

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Official URL: https://doi.org/10.1371/journal.pone.0131896

Abstract

Drugs such as necopidem, saripidem, alpidem, zolpidem, and olprinone contain nitrogencontaining bicyclic, condensed-imidazo1,2-αpyridines as bioactive scaffolds. In this work, we report a high-yield one pot synthesis of 1-(2-methyl-8-aryl-substitued-imidazo1,2-α pyridin-3-yl)ethan-1-onefor the first-time. Subsequently, we performed in silico mode-ofaction analysis and predicted that the synthesized imidazopyridines targets Phospholipase A<inf>2</inf> (PLA<inf>2</inf>). In vitro analysis confirmed the predicted target PLA<inf>2</inf> for the novel imidazopyridine derivative1-(2-Methyl-8-naphthalen-1-yl-imidazo 1,2-αpyridine-3-yl)-ethanone (compound 3f) showing significant inhibitory activity towards snake venom PLA<inf>2</inf> with an IC<inf>50</inf> value of 14.3 μM. Evidently, the molecular docking analysis suggested that imidazopyridine compound was able to bind to the active site of the PLA<inf>2</inf> with strong affinity, whose affinity values are comparable to nimesulide. Furthermore, we estimated the potential for oral bioavailability by Lipinski's Rule of Five. Hence, it is concluded that the compound 3f could be a lead molecule against snake venom PLA<inf>2</inf>. © 2015 Anilkumar et al.This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

Item Type: Article
Additional Information: cited By 1
Uncontrolled Keywords: 1 (2 methyl 8 phenylimidazo1,2 apyridin 3 yl)ethanone; 1 2 methyl 8 (naphthalen 1 yl)imidazo1,2 a]pyridine 3 yl]ethanone; 1 2 methyl 8 (o tolyl)imidazo1,2 a]pyridin 3 yl]ethanone; 1 2 methyl 8 4 (trifluoromethyl)phenyl]imidazo1,2 apyridin 3 ylethanone; 1 8 (2 fluoro 3 methoxyphenyl) 2 methylimidazo1,2 apyridin 3 ylethanone; 1 8 (3 chlorophenyl) 2 methylimidazo1,2 apyridin 3 ylethanone; 1 8 (3 methoxyphenyl) 2 methylimidazo1,2 apyridin 3 ylethanone; 1 8 (4 chlorophenyl) 2 methylimidazo1,2 apyridin 3 ylethanone; 1 8 (4 ethylphenyl) 2 methylimidazo1,2 apyridin 3 ylethanone; 1 8 4 (benzyloxy) 3 fluorophenyl 2 methylimidazo1,2 apyridin 3 ylethanone; 1 8 4 chloro 3 (trifluoromethyl)phenyl 2 methylimidazo1,2 apyridin 3 ylethanone; 4 (3 acetyl 2 methylimidazo1,2 apyridin 8 yl) n cyclopentyl 2 ethylbutanamide; imidazopyridine derivative; nimesulide; phospholipase A2; phospholipase A2 inhibitor; snake venom; unclassified drug, Article; binding affinity; controlled study; cyclization; Daboia russellii; drug synthesis; drug targeting; enzyme active site; enzyme inhibition; hemolysis; IC50; in vitro study; molecular docking; one pot synthesis; structure activity relation; Suzuki reaction
Subjects: Faculty of Science > Pure Sciences > Chemistry
Divisions: Jnana Bharathi / Central College Campus > Department of Chemistry
Depositing User: Mr. Kirana Kumar D
Date Deposited: 29 Mar 2016 05:16
Last Modified: 29 Mar 2016 05:16
URI: http://eprints-bangaloreuniversity.in/id/eprint/3266

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