Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents.

J Nat Prod

Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group , Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar , Hyderabad - 500078 , Telangana , India.

Published: January 2020

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles - as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone with a terminal ethynyl moiety. It was further reacted with various azides - under copper catalysis to give triazoles - in good yields. Among the synthesized compounds, saccharin derivative proved to be the most active analogue, inhibiting () at an MIC value of 2.5 μM. Analogues and , with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on , with compounds [3-(trifluoromethyl)phenacyl] and (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

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http://dx.doi.org/10.1021/acs.jnatprod.9b00475DOI Listing

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