| Autor: |
Bangalore PK, Vagolu SK; Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group , Birla Institute of Technology & Science-Pilani , Hyderabad Campus, Jawahar Nagar , Hyderabad - 500078 , Telangana , India., Bollikanda RK, Veeragoni DK, Choudante PC, Misra S, Sriram D; Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group , Birla Institute of Technology & Science-Pilani , Hyderabad Campus, Jawahar Nagar , Hyderabad - 500078 , Telangana , India., Sridhar B, Kantevari S |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of natural products [J Nat Prod] 2020 Jan 24; Vol. 83 (1), pp. 26-35. Date of Electronic Publication: 2019 Dec 20. |
| DOI: |
10.1021/acs.jnatprod.9b00475 |
| Abstrakt: |
(+)-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 10 - 44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1 - A35 under copper catalysis to give triazoles 10 - 44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis ( Mtb ) at an MIC value of 2.5 μM. Analogues 16 and 27 , with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb 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 Bacillus subtilis , with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (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. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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