Benzene sulfonamide pyrazole thio-oxadiazole hybrid as potential antimicrobial and antitubercular agents
To fulfil the development goals towards the synthesis of innovative, potent and highly effective antimicrobial and antimycobacterial agents, a set of benzene sulfonamide pyrazole thio-oxadiazole derivatives (6a–6l) have been synthesized by the reaction of 4-[5-(3-fluoro-4-methoxyphenyl)-3-(5-mercapto-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl]benzenesulfonamide with alkyl/aryl halides, identified by IR, NMR (1H, 13C, 19F) and MS data. Composed compounds were examined for their antimicrobial and antitubercular activity. Antibacterial activity of compounds 6c, 6d, 6j and 6l was found promising against E. coli, P. Aeruginosa, S. Aureus and S. Pyogenes as compared to standard ampicillin. Compounds 6d, 6e, 6g, 6h and 6i were found active against tubercular strain H37Rv. Molecular docking studies against mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthase A (Kas-A) was carried out which suggests a possible mode of inhibition for this target protein and the potential of synthesized compounds as antitubercular agents.
KeywordsBenzene sulfonamide pyrazole Thio-oxadiazole Antimicrobial Antitubercular activity Molecular docking
The authors are thankful to the DST, New Delhi, for financial support and also thanks to Atul Ltd. for providing chemicals.
- 1.New global commitment to end tuberculosis. (WHO, 2017)Google Scholar
- 2.10 facts on antimicrobial resistance. (WHO, 2017)Google Scholar
- 3.The End TB strategy. (WHO, 2015)Google Scholar
- 17.K.A. Abrahams, C. Chung, S. Ghidelli-Disse, J. Rullas, M.J. Rebollo-Lopez, S.S. Gurcha, J.A.G. Cox, A. Mendoza, E. Jimenez-Navarro, M.S. Martinez-Martinez, M. Neu, A. Shillings, P. Homes, A. Argyrou, R. Casanueva, N.J. Loman, P.J. Moynihan, J. Lelievre, C. Selenski, M. Axtman, L. Kremer, M. Bantscheff, I. Angulo-Barturen, M.C. Izquierdo, N.C. Cammack, G. Drewes, L. Ballell, D. Barros, G.S. Besra, R.H. Bates, Nat. Commun. 7, 12581 (2016)CrossRefPubMedPubMedCentralGoogle Scholar
- 18.A. Chowdhury, P. Dey, S. Sen, P. Chetia, M.D. Choudhury, G.D. Sharma, Asian J. Pharm. Clin. Res. 5, 60 (2012)Google Scholar
- 19.R. Shingare, Y. Patil, S. Gadekar, J. Sangshetti, B. Madje, Mor. J. Chem. 5, 177 (2017)Google Scholar
- 20.R.M. Shingare, Y.S. Patil, J.N. Sangshetti, R.B. Patil, D.P. Rajani, B.R. Madje, Med. Chem. Res. (2018)Google Scholar
- 24.P.M. Hawkey, D.A. Lewis, Medical Bacteriology-A Practical approach (Oxford University Press, Oxford, 1994), pp. 181–194Google Scholar
- 26.H.D. Isenberg, Clinical Microbiology Procedures Handbook, vol. 1 (American society for microbiology, Washington, 1992)Google Scholar
- 30.H.N. Raundal, R.P. Jadhav, A.A. Patil, V.D. Bobade, Indian J. Chem. 54B, 979 (2015)Google Scholar
- 31.H.N. Raundal, R.P. Jadhav, A.A. Patil, V.D. Bobade, Indian J. Chem. 55B, 892 (2016)Google Scholar