Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives.
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 alpha-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, (1)H NMR, (13)C 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 microg/mL. Compound 18 showed a MIC of 20 microg/mL.
Gadad
Andanappa K
AK
Department of Medicinal Chemistry, College of Pharmacy, JN Medical College, Nehru Nagar, Belgaum 590 010, Karnataka, India. akgadad@rediffmail.com
Noolvi
Malleshappa N
MN
Karpoormath
Rajshekhar V
RV
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009169:Mycobacterium tuberculosis / Q000187:drug effects* / Q000502:physiology; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000995:Antitubercular Agents; D007093:Imidazoles; D013830:Thiadiazoles