Design,synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents |
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| Institution: | 1. Jyoti Nivas College, Autonomous, Department of Studies in Chemistry, Bangalore 560095, India;2. Institute for Stem Cell Biology and Regenerative Medicine, NCBS-TIFR Campus, UAS-GKVK, Bellary Road, Bangalore 560065;3. South African Medical Research Council Drug Discovery and Development Research Unit, Department of Chemistry and Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Rondebosch 7701, South Africa;4. Drug Discovery and Development Centre (H3D), University of Cape Town, Rondebosch 7701, South Africa;5. Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa;6. Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Kingdom of Saudi Arabia |
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| Abstract: | 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 µg/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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| Keywords: | Cinnamic acid 1 2 4-oxadiazole Anti-tubercular Bioisosteres Molecular docking |
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