Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents

TitleDesign, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents
Publication TypeJournal Article
Year of Publication2019
AuthorsUpare, AAtmaram, Gadekar, PK, Sivaramakrishnan, H, Naik, N, Khedkar, VM, Sarkar, D, Choudhari, A, S. Roopan, M
JournalBioorganic Chemistry
Date PublishedMAY
Type of ArticleArticle
Keywords1, 2, 4-Oxadiazole, Anti-tubercular, Bioisosteres, Cinnamic acid, Molecular docking

Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with ``oxadiazole''. A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound 32 displayed potent anti-tubercular activity (IC50= 0.045 mu g/mL). Molecular docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the experimental findings providing a platform for structure based hit-to-lead development.

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Organic Chemistry