Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 26; no. 7; pp. 1704 - 1708
• Main Authors: Subhedar, Dnyaneshwar D., Shaikh, Mubarak H., Arkile, Manisha A., Yeware, Amar, Sarkar, Dhiman, Shingate, Bapurao B.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.04.2016; Elsevier
• Subjects: Animals; Antitubercular; Antitubercular Agents - chemical synthesis; Antitubercular Agents - chemistry; Antitubercular Agents - pharmacology; Cell Line; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Combinatorial Chemistry Techniques - economics; Combinatorial Chemistry Techniques - methods; Cytotoxicity; Green Chemistry Technology - economics; Green Chemistry Technology - methods; Green protocol; Humans; Life Sciences & Biomedicine; Microbial Sensitivity Tests; Multicomponent reaction; Mycobacterium bovis; Mycobacterium bovis - drug effects; Mycobacterium tuberculosis; Mycobacterium tuberculosis - drug effects; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Structure-Activity Relationship; Thiazolidines - chemical synthesis; Thiazolidines - chemistry; Thiazolidines - pharmacology; Tuberculosis - drug therapy; Tuberculosis - veterinary; Cytotoxicity; Multicomponent reaction; Antitubercular; Green protocol; 4-THIAZOLIDINONES; THIAZOLIDIN-4-ONES; ANTICANCER; ONE-POT 3-COMPONENT; ANTIFUNGAL; AMMONIUM IONIC LIQUIDS; DERIVATIVES; EFFICIENT; CATALYSTS
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2016.02.056

[Display omitted] We have developed, highly efficient, one-pot, solvent-free, [Et3NH][HSO4] catalyzed multicomponent reaction protocol for the synthesis of 1,3-thiazolidin-4-ones in excellent yields. For the first time, the 1,3-thiazolidin-4-ones were evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis dormant MTB H37Ra and Mycobacterium bovis BCG strains. Among the synthesized basic 1,3-thiazolidin-4-ones, particularly the compounds 4c, 4d, 4e, 4f, 4h, 4i and 4j displays promising antitubercular activity along with no significant cytotoxicity against the cell lines MCF-7, A549 and HCT-116.