Synthesis and antibacterial activity of 2,2'-dithiobis(benzamide) derivatives against Mycobacterium species.
A series of compounds, which are analogues of 2,2'-dithiobis(benzamide), were synthesized and tested for in vitro antibacterial activity against Mycobacterium tuberculosis H37Rv including resistant strains against streptomycin, kanamycin, or isonicotinic acid hydrazide. MICs of these compounds against atypical mycobacteria, Mycobacterium kansasii and Mycobacterium intracellulare were also examined. Structure-activity relationships were found in a series of (acyloxy)alkyl ester derivatives depending upon the length of alkyl carbon chain. The MIC of the most potent compound, 2,2'-dithiobis[N-[3-(decanoyloxy)propyl]benzamide] [56] was superior or at least equivalent to streptomycin, kanamycin, and ethanbutol. All the compounds showed no cross-resistance between the current antitubercular agents.
D000818:Animals; D001549:Benzamides / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D055598:Chemical Phenomena; D002621:Chemistry; D004305:Dose-Response Relationship, Drug; D004352:Drug Resistance, Microbial; D051379:Mice; D009161:Mycobacterium / Q000187:drug effects* / Q000254:growth & development; D009169:Mycobacterium tuberculosis / Q000187:drug effects / Q000254:growth & development; D009170:Nontuberculous Mycobacteria / Q000187:drug effects; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity
D001549:Benzamides; D013440:Sulfides