• Manjoor Ahamad Syed RGUHS



The 6-(4-substituted aryl)-2-(3,5-dimethyl-1H-pyrazol-1-yl)imidazo[2,1-b][1,3,4]thiadiazole (2a to f) were prepared by treating 2-amino-5-(3,5-dimethyl-H-pyrazole-1yl)-1,3,4-thiadiazole with appropriate α-haloaryl ketones. The reaction 2 with morpholine using formaldehyde, acetic acid in methanol yielded the corresponding 5- morpholin-4-ylmethyl derivatives (3a-e). While compound 2 also produces the 5- pyrrolidine-4-ylmethyl derivatives (4a-e) by reaction with pyrrolidine using formaldehyde, acetic acid in methanol. The 5- piperidin-4-ylmethyl derivatives (5a-e) were obtained by treating compound 2 with piperidine using formaldehyde, acetic acid in methanol. The structures of the newly synthesized compounds confirmed by IR, NMR and Mass spectra. All the compounds were screened for antitubercular and antifungal activity. Some of the compound displayed very good antitubercular and antifungal activity.

Keywords: 2-Amino-5-(3,5-dimethyl-H-pyrazole-1yl)-1,3,4-thiadiazole; Imidazo[2,1-b][1,3,4] thiadiazole; Antitubercular activity; Antifungal activity.

Author Biography

Manjoor Ahamad Syed, RGUHS
Pharmaceutical Chemistry


1. Rattan A., Kalia A., Ahmad N. Multidrug-resistant Mycobacterium tuberculosis: molecular perspectives Emerg. Infect. Dis.1998; 4(2): 195-209.

2. Desai K., Baxi A. J. Studies on 2-azetidinone: Part-VI Synthesis and antimicrobial activity of 5-(2’,4’-dichlorophenoxymethyl)-2-(4’’-aryl-3’’-chloro-2’’-azetidinone-1’’-yl)-1,3,4-thiadiazole. Indian J. Pharm. Sci. 1992; 54: 183-188.

3. N. G. Gawande, M. S. Shingare, et al. Synthesis of some Thiazolyl-thiosemicarbazides. Triazoles, Oxadiazoles, Thiadiazoles & Their Microbial Activity; Indian J. Chem. 1987; 26B: 387-389.

4. Mamolo MG, Vio L, Banfi E. Synthesis and antimicrobial activity of some 2,5-disubstituted 1,3,4,-thiadiazole derivatives. Farmaco, 1996; 51: 71-4.

5. Gadad AK, Chanabasappa S, Mahajanshetti, Nimbalkar S, Raichurkar A. Synthesis and antibacterial activity of some guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives. Eur. J. Med. Chem. 2000; 35: 853−857.

6. Alireza F., Fatemeh S., Mohmmad H. M., Rogheeyeh A. A. a series of 2,6-disubstituted and 2,5,6-trisubstituted imidazo[2,1-b][1,3,4] thiadiazole. II Farmaco 2003; 58: 1023.

7. Gadad A.K., Malleshappa N., Noolvi, Rajshekhar V., Karpoormath. Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo-[2,1-b]-1,3,4-thiadiazole derivatives. Bioorganic & Medicinal Chemistry 2004; 12: 5651–5659.

8. Song Y., Connor D. T., Sercel A. D., Soreson R. J., Doubleday R., et al., Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 2. 1,3,4- and 1,2,4-thiadiazole series. J. Med. Chem. 1999; 42 (7): 1161-9.

9. Labanauskas L., Kalcas V., Udrenaite E., Gaidelis P., Brukstus A., Dauksas A. Synthesis of 3-(3,4-dimethoxyphenyl)-1 H-1,2,4-triazole-5-thiol and 2-amino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazole derivatives exhibiting anti-inflammatory activity Pharmazie 2001; 56(8): 617-9.

10. Chapleo C. B., Myers M., Myers P. L., Saville J. F., Smith A. C. B. et al., Substituted 1,3,4-thiadiazoles with anticonvulsant activity. 1. Hydrazines. J. Med. Chem. 1986; 29(11): 2273-80.

11. Chapleo C. B., Myers P. L., Smith A. C., Stillings M. R., Tulloch I. F., Walter D. S. Substituted 1,3,4-thiadiazoles with anticonvulsant activity. 4. Amidines. J. Med. Chem. 1988; 31(1): 7-11.

12. Turner S., Myers M., Gadie B., Nelson A.J., et al. Antihypertensive thiadiazoles: Synthesis of some 2-aryl-5-hydrazino-1,3,4-thiadiazoles with vasodilator activity. J Med Chem 1988; 31: 902-6.

13. Turner S., Myers M., Gadie B., Nelson A.J., et al. Antihypertensive thiadiazoles. Vasodilator activity of some 2-aryl-5-guanidino-1.3.4-thiadiazoles. J Med Chem 1988; 31: 907-13.

14. Chou J. Y., Lai S. Y., Pan S. L., Jow G. M., Chern J.W., Guh J. H. Investigation of anticancer mechanism of thiadiazole-based compound in human non-small cell lung cancer A549 cells. Biochem. Pharmacol. 2003; 66(1): 115-24.

15. Collins L., Franzblau S. G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother.1997; 41: 1004.

16. Franzblau SG, Witzig RS, McLaughlin JC, Torres P, Madico G, et al., Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol. 1998; 36(2): 362–366.

17. Yajko D. M., Madej J. J., Gee B., Babst A., KeithHardley W. Colorimetric method for determining MICs of antimicrobial agents for Mycobacterium tuberculosis. J. Clin. Microb. 1995; 33: 2324.

18. Suling W. J., Seitz L. E., Pathak V., Westbrook L., Barrow E. W. et al., Antimycobacterial activities of 2,4-diamino-5-deazapteridine derivatives and effects on mycobacterial dihydrofolate reductase. Antimicrob. Agents Chemother. 2000; 44(10): 2784-93.

19. Gadad A.K., Khaji I.M. Synthesis and antibacterial activity of various 2-alkyl- 6-aryl imidazo(2,1-b)-1,3,4-thiadiazole. Ind. J. Het. Chem. 1992; 2: 125.

20. Kolavi G., Hegde V., Khazi I.A., Gadad P. Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives. Bioorganic & Medicinal Chemistry, 2006; 14(9): 3069-80.
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How to Cite
Syed, M. A., A. K. RAMAPPA, and S. ALEGAON. “SYNTHESIS AND EVALUATION OF ANTITUBERCULAR AND ANTI FUNGAL ACTIVITY OF SOME NOVEL 6-(4-SUBSTITUTED ARYL)-2-(3,5-DIMETHYL-1H-PYRAZOL-1-YL) IMIDAZO[2,1-B] [1,3,4] THIADIAZOLE DERIVATIVES”. Asian Journal of Pharmaceutical and Clinical Research, Vol. 6, no. 7, Aug. 2013, pp. 47-51,