Benzene sulfonamide pyrazole thio-oxadiazole hybrid as potential antimicrobial and antitubercular agents

  • Ramesh M. Shingare
  • Yogesh S. Patil
  • Jaiprakash N. Sangshetti
  • Rajesh B. Patil
  • Dhanji P. Rajani
  • Smita D. Rajani
  • Balaji R. Madje
Article
  • 23 Downloads

Abstract

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.

Keywords

Benzene sulfonamide pyrazole Thio-oxadiazole Antimicrobial Antitubercular activity Molecular docking 

Notes

Acknowledgements

The authors are thankful to the DST, New Delhi, for financial support and also thanks to Atul Ltd. for providing chemicals.

Supplementary material

11164_2018_3396_MOESM1_ESM.docx (22.2 mb)
Supplementary material 1 (DOCX 22757 kb)

References

  1. 1.
    New global commitment to end tuberculosis. (WHO, 2017)Google Scholar
  2. 2.
    10 facts on antimicrobial resistance. (WHO, 2017)Google Scholar
  3. 3.
    The End TB strategy. (WHO, 2015)Google Scholar
  4. 4.
    M. Koparir, A. Cetin, A. Cansiz, Molecules 10, 475 (2005)CrossRefGoogle Scholar
  5. 5.
    R.V. Patel, P. Kumari, D.P. Rajani, K.H. Chikhalia, Med. Chem. Res. 22, 195 (2013)CrossRefGoogle Scholar
  6. 6.
    T. Chandra, N. Garg, S. Lata, K.K. Saxena, A. Kumar, Eur. J. Med. Chem. 45, 1772 (2010)CrossRefGoogle Scholar
  7. 7.
    M.M. Gamal El-Din, M.I. El-Gamal, M.S. Abdel-Maksoud, K.H. Yoo, C.H. Oh, Eur. J. Med. Chem. 90, 45 (2015)CrossRefGoogle Scholar
  8. 8.
    M. Zareef, R. Iqbal, N.G. Dominguez, J. Rodrigues, J.H. Zaidi, M. Arfan, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 22, 301 (2007)CrossRefGoogle Scholar
  9. 9.
    X.M. Zhang, M. Qiu, J. Sun, Y.B. Zhang, Y.S. Yang, X.L. Wang, J.F. Tang, H.L. Zhu, Bioorg. Med. Chem. 19, 6518 (2011)CrossRefGoogle Scholar
  10. 10.
    M.F. Salah El-Din, H.A. Ismail, S.R. Helmy, M.N.G. Abd El-Moaen, Lett. Drug Des. Discov. 11, 304 (2014)CrossRefGoogle Scholar
  11. 11.
    S.V. Bhandari, J.K. Parikh, K.G. Bothara, T.S. Chitre, D.K. Lokwani, T.L. Devale, N.S. Modhave, V.S. Pawar, S. Panda, J. Enzyme Inhib. Med. Chem. 25, 520 (2010)CrossRefGoogle Scholar
  12. 12.
    G.A. Idrees, O.M. Aly, G.E.D.A.A. Abuo-Rahma, M.F. Radwan, Eur. J. Med. Chem. 44, 3973 (2009)CrossRefGoogle Scholar
  13. 13.
    T. Kampmanna, R. Yennamallia, P. Campbella, M.J. Stoermerc, P. David, D.P. Fairlie, B. Kobea, P.R. Young, Antivir. Res. 84, 234 (2009)CrossRefGoogle Scholar
  14. 14.
    T.M.C. Tan, Y. Chen, K.H. Kong, J. Bai, Y. Li, S.G. Lim, T.H. Ang, Y. Lam, Antivir. Res. 71, 7 (2006)CrossRefGoogle Scholar
  15. 15.
    S. Viveka, P. Dinesha, G.K. Shama, N. Nagaraja, M.Y. Sreenivasa Deepa, Res. Chem. Intermed. 42, 2597 (2016)CrossRefGoogle Scholar
  16. 16.
    J. Schiebel, K. Kapilashrami, A. Fekete, G.R. Bommineni, C.M. Schaefer, M.J. Mueller, P.J. Tonge, C. Kisker, J. Biol. Chem. 288, 24190 (2013)CrossRefGoogle Scholar
  17. 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)CrossRefGoogle Scholar
  18. 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. 19.
    R. Shingare, Y. Patil, S. Gadekar, J. Sangshetti, B. Madje, Mor. J. Chem. 5, 177 (2017)Google Scholar
  20. 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
  21. 21.
    H.A. Abdel-Aziz, K.A. Al-Rashood, K.E.H. ElTahir, G.M. Suddek, Eur. J. Med. Chem. 80, 416 (2014)CrossRefGoogle Scholar
  22. 22.
    A.A. Bekhit, H.M.A. Ashour, A. Bekhit, A. El-Din, H.M. Abdel-Rahman, S.A. Bekhit, J. Enzyme Inhib. Med. Chem. 24, 296 (2009)CrossRefGoogle Scholar
  23. 23.
    T. Rogez-Florent, S. Meignan, C. Foulon, P. Six, A. Gros, C. Bal-Mahieu, C.T. Supuran, A. Scozzafava, R. Frederick, B. Masereel, P. Depreux, A. Lansiaux, J.F. Goossens, S. Gluszok, L. Goossens, Bioorg. Med. Chem. 21, 1451 (2013)CrossRefGoogle Scholar
  24. 24.
    P.M. Hawkey, D.A. Lewis, Medical Bacteriology-A Practical approach (Oxford University Press, Oxford, 1994), pp. 181–194Google Scholar
  25. 25.
    P. Anargyros, D.S. Astill, I.S. Lim, J. Clin. Microbiol. 28, 1288 (1990)Google Scholar
  26. 26.
    H.D. Isenberg, Clinical Microbiology Procedures Handbook, vol. 1 (American society for microbiology, Washington, 1992)Google Scholar
  27. 27.
    N.B. Patel, I.H. Khan, S.D. Rajani, Eur. J. Med. Chem. 45, 4293 (2010)CrossRefGoogle Scholar
  28. 28.
    O. Trott, A.J. Olson, J. Comput. Chem. 31, 455 (2010)Google Scholar
  29. 29.
    E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, T.E. Ferrin, J. Comput. Chem. 25, 1605 (2004)CrossRefGoogle Scholar
  30. 30.
    H.N. Raundal, R.P. Jadhav, A.A. Patil, V.D. Bobade, Indian J. Chem. 54B, 979 (2015)Google Scholar
  31. 31.
    H.N. Raundal, R.P. Jadhav, A.A. Patil, V.D. Bobade, Indian J. Chem. 55B, 892 (2016)Google Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  • Ramesh M. Shingare
    • 1
  • Yogesh S. Patil
    • 1
  • Jaiprakash N. Sangshetti
    • 2
  • Rajesh B. Patil
    • 3
  • Dhanji P. Rajani
    • 4
  • Smita D. Rajani
    • 5
  • Balaji R. Madje
    • 1
  1. 1.Department of ChemistryVasantrao Naik MahavidyalayaAurangabadIndia
  2. 2.Y. B. Chavan College of PharmacyAurangabadIndia
  3. 3.Sinhgad Technical Education Society’sSmt. Kashibai Navale College of PharmacyPuneIndia
  4. 4.Microcare Laboratory and Tuberculosis Research CenterSuratIndia
  5. 5.Shree Ramkrishna Institute of Applied SciencesSuratIndia

Personalised recommendations