Synthesis and evaluation of antibacterial and antitubercular activities of some novel imidazo[2,1-b][1,3,4]thiadiazole derivatives

Medicinal Chemistry Research

Volumn 22, Issue 2, 2013, Pages 869-878

  Joshi, S D ^a   Manish, K ^a   Badiger, Aravind ^b  

^a S E T S COLLEGE OF PHARMACY   (India)

^b Shree Dhanvantary Pharmacy College   (India)

Author keywords

Antibacterial activities; Antitubercular; Imidazo 2,1 b 1,3,4 thiadiazole

Indexed keywords

2 [ 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)] SULFONAMIDO] 3 PHENYL 1,3 THIAZOLIDIN 4 ONE; 5 (MORPHOLIN 4 YLMETHYL) 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULFONAMIDE; 5 (PIPERIDIN 1 YLMETHYL) 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULFONAMIDE; 5 (PYRROLIDIN 1 YLMETHYL) 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULFONAMIDE; 5 AMINO 1,3,4 THIADIAZOLE 2 SULPHONAMIDE; 5 BROMO 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULFONAMIDE; 5 FORMYL 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)]; 5 FORMYL 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)] SULFONAMIDE; 5 GUANYLHYDRAZONE 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)] SULFONAMIDE; 5 NITROSO 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULFONAMIDE; 5 THIOCYANATO 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULPHONAMIDE; 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)] SULFONAMIDO 5 CARBONITRILE; 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 SULFONAMIDE; 6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)] SULFONAMIDO 5 CARBALDEHYDEOXIME; 7 DIETHYLAMINO 3 BROMOACETYL 2H CHROMEN 2 ONE; [6 [7 (DIETHYLAMINO) 2 OXO 2H CHROMEN 3 YL]IMIDAZO[2,1 B][1,3,4]THIADIAZOLE 2 [N (DIMETHYLAMINOMETHINO)] SULFONAMIDO 5 YL]METHANOL; ANTIMYCOBACTERIAL AGENT; IMIDAZO[2,1B ][1,3,4]THIADIAZOLE; THIADIAZOLE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; STAPHYLOCOCCUS AUREUS; TUBERCULOSIS; VIBRIO CHOLERAE;

EID: 84874000125     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0080-4     Document Type: Article

References (17)

1. Andreani A, Leonia A, Locatelli A, Morigi R, Rambaldi M, Simon WA, Senn-Bilfinger J (2000) Synthesis and antisecretory activity of 6-substitute cyanomethylimidazo[2,1-b]thiazoles and 2,6-dimethyl-5-hydroxylmethyl imidazo[2,1-b][1,3,4]thiadiazole. Arzneimittelforschung 50:550-553
2. Corbett EL, Watt CJ, Walker N, Maher D, Williams BG, Raviglione MC, Dye C (2003) The growing burden of tuberculosis: global trends and interactions with the HIV epidemic. Arch Int Med 163:1009-1021
3. Duncan K (1997) In antituberculosis drug resistance in the World the WHO/IUALTD. Global project on antituberculosis drug resistance surveillance. World Health Organization, Chem India, p 861
4. Foroumadi A, Emami S, Pournourmohammadi S, Kharazmi A, Shafiee A (2005) Synthesis and in vitro leishmanicidal activity of 2-(1-methyl-5-nitro-1H- imidazol-2-yl)-5-substituted-1,3,4-thiadiazole derivatives. Eur J Med Chem 40:1346-1350
5. Franzblau SG, Witzig RS, McLaughlin JC, Torres P, Madico G, Hernandez A, Degnan MT, Cook MB, Quenzer VK, Ferguson RM, Gilman RH (1998) Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate alamar blue assay. J Clin Microbiol 36:362-366
6. Gadad AK, Mahajanshetti CS, Nimbalkar S, Raichurkar A (2000) Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6- arylimidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamide derivatives. Eur J Med Chem 35:853-857
7. Gadad AK, Noolvi MN, Karpoormath RV (2004) Synthesis and antitubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives. Bioorg Med Chem 12:5651-5659
8. Jadhav VB, Kulkarni MV, Rasal VP, Biradar SS, Vinay MD (2008) Synthesis and anti- inflammatory evaluation of methylene bridged benzofuranyl imidazo[2,1-b][1,3,4]thiadiazoles. Eur J Med Chem 43:1721-1729
9. Karki SS, Panjamurthy K, Kumar S, Nambiar M, Ramareddy SA, Chiruvella KK, Raghavan SC (2011) Synthesis and biological evaluation of novel 2-aralkyl-5-substituted-6-(4′-fluorophenyl)- imidazo[2,1-b][1,3,4] thiadiazole derivatives as potent anticancer agents. Eur J Med Chem 46:2109-2116
10. Khazi IA, Mahajanshetti CS, Gadad AK, Tarnalli AD, Sultanpur CM (1996) Anticonvulsant and analgesic activities of some 6-substituted imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamides and their 5-bromo derivatives. Arzneimittelforschung 46:949-952
11. Kolavi G, Hegde V, Khazi IA, Gadad P (2006) Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives. Bioorg Med Chem 14:3069-3080
12. Mather D, Floyd K, Ravglione M (2002) World Health Organization, Geneva
13. Noolvi MN, Patel HM, Singh N, Gadad AK, Cameotra SS, Badiger A (2011) Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo[2,1-b][1,3,4]- thiadiazole derivatives. Eur J Med Chem 46:4411-4418
14. Qian L, Montellano PRO (2006) Oxidative activation of thiacetazone by the Mycobacterium tuberculosis flavin monooxygenase EtaA and human FMO1 and FMO3. Chem Res Toxicol 19:443-449
15. Terzioglu N, Gursoy A (2003) Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5- carbohydrazide. Eur J Med Chem 38:781-786
16. Valadas E, Antunes F (2005) Tuberculosis, a re-emergent disease. Eur J Radiol 55:154-157
17. Yajko DM, Madej JJ, Lancaster MV, Sanders CA, Cawthon VL, Gee B, Babst A, Hadley WK (1995) Colorimetric method for determining MICs of antimicrobial agents for Mycobacterium tuberculosis. J Clin Microbiol 33:2324-2327