title: Synthesis and anti-mycobacterial activity of new 4-thiazolidinone and 1,3,4-oxadiazole derivatives of isoniazid.
abstract: A new series of 4-thiazolidinone (3a-e) and 1,3,4-oxadiazole (4a-e) derivatives of isoniazid were synthesized and evaluated for their in vitro anti-mycobacterial activity. The structures of the compounds were confirmed on the basis of spectral data and elemental analysis. Some compounds showed interesting activity against four Mycobacterium strains: M. intercellulari (ATCC 35743), M. xenopi (ATCC 14470), M. cheleneo (ATCC 35751) and M. smegmatis (ATCC 35797). Compounds 3e, N-(4-oxo-2-undecylthiazolidin-3-yl) isonicotinamide and 4e N-acetyl-4-(5-undecyl-1,3,4-oxadiazol-2-yl) pyridine with minimum inhibitory concentration (MIC), 6.0 μg/mL were found to be more potent than isoniazid under the in vitro investigational conditions. Compound 3e and 4e bear a high lipophilic chain bonded to the 5-position of the thiazolidinone and 1,3,4-oxadiazole moiety, respectively. This fact indicates that there exists a contribution of lipophilicity, which would facilitate the transport of these molecules through membranes.
authors.forename: Mashooq A
authors.initials: MA
authors.lastname: Bhat
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D007538:Isoniazid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000145:classification / Q000187:drug effects* / Q000254:growth & development; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000995:Antitubercular Agents; D010069:Oxadiazoles; D053778:Thiazolidines; C583463:1,3,4-oxadiazole; D007538:Isoniazid