Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo[2,1- b]-1,3,4-thiadiazole derivatives

• Published in: Bioorganic & medicinal chemistry 2004-11, Vol.12 (21), p.5651-5659
• Main Authors: Gadad, Andanappa K., Noolvi, Malleshappa N., Karpoormath, Rajshekhar V.
• Format: Article
• Language: English
• Subjects: Anti-tubercular activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antitubercular Agents - chemical synthesis; Antitubercular Agents - pharmacology; BACTEC assay; Biological and medical sciences; Imidazo[2,1- b]-1,3,4-thiadiazoles; Imidazoles - chemical synthesis; Imidazoles - pharmacology; Medical sciences; Mycobacterium tuberculosis - drug effects; Mycobacterium tuberculosis - physiology; Pharmacology. Drug treatments; Thiadiazoles - chemical synthesis; Thiadiazoles - pharmacology; α-Haloaryl/heteroaryl ketones
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2004.07.060

[Display omitted] A series of 2-sulfonamido/trifluoromethyl-6-(4′-substituted aryl/heteroaryl)imidazo[2,1- b]-1,3,4-thiadiazole derivatives ( II) have been synthesized by reaction of 2-amino-5-sulfonamido/trifluoromethyl-1,3,4-thiadiazoles and an appropriate α-haloaryl/heteroaryl ketones. Further 5-bromo ( III), 5-thiocyanato ( IV), 5-gaunylhydrazone ( V) derivatives were synthesized in order to study the effect of these substituents on biological activity. Structures of these compounds were established by IR, 1H NMR, 13C NMR, Mass and HRMS. The selected compounds were evaluated for their preliminary in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain using radiometric BACTEC and broth dilution assay methods. The results show that compounds 5, 7, 8, 10 and 12 exhibited moderate to good anti-tubercular activity with percentage inhibition of 29, 43, 58, 31 and 41, respectively, at a MIC of >6.25 μg/mL. Compound 18 showed a MIC of 20 μg/mL.