Skip to main content
Log in

Synthesis, characterization and antimicrobial screening of thiazole based 1,3,4-oxadiazoles heterocycles

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In an effort to find a new pharmacologically dynamic molecule, we report here the synthesis and in vitro antimicrobial activity of various N-(4-methyl-5-(4-((substituted phenylamino) methyl)-5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)thiazol-2-yl) benzamides. The structures of newly synthesized compounds were assigned on the bases of IR, 1H NMR, 13C NMR, and mass spectral data. Synthesized compounds were screened for their antibacterial and antifungal activities on gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes), gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) and three fungi (Candida albicans, Aspergillus niger and Aspergillus clavatus) by serial broth dilution method. Compounds 5e and 5k were associated with considerable potential antibacterial and compounds 5a and 5b antifungal activities.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. R.R. William, R.E. Waterman, J.C. Keresztesy, E.R. Buchman, J. Am. Chem. Soc. 57, 536–537 (1935)

    Article  Google Scholar 

  2. K. Taori, V.J. Paul, H. Luesch, J. Am. Chem. Soc. 130, 1806–1807 (2008)

    Article  CAS  Google Scholar 

  3. R.S. Koti, G.D. Kolavi, V.S. Hegde, I.M. Khaji, Ind. J. Chem. 45, 1900–1904 (2006)

    Google Scholar 

  4. A. Geronikaki, I. Argyropoulou, P. Vicini, F. Zani, Arkivoc 6, 89–102 (2009)

    Google Scholar 

  5. A.K. Singh, G. Mishra, K. Jyoti, J. Appl. Pharm. Sci. 5, 44–49 (2011)

    Google Scholar 

  6. V. Jaishree, N. Ramdas, J. Sachin, B. Ramesh, J. Saudi Chem. Soc. 16, 371–376 (2012)

    Article  CAS  Google Scholar 

  7. S.J. Kashyap, P.K. Sharma, V.K. Garg, R. Dudhe, N. Kumar, J. Adv. Sci. Res. 2, 18–24 (2011)

    CAS  Google Scholar 

  8. V.U. Jeankumar, S. Kotagiri, R. Janupally, P. Suryadevara, J.P. Sridevi, R. Medishetti, P. Kulkarni, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 23, 588–601 (2015)

    Article  CAS  Google Scholar 

  9. V.D. Mathew, J. Giles, Keshavayya, V.P. Vaidya, Arch. Pharm. Chem. Life Sci. 342, 210–222 (2009)

    Article  CAS  Google Scholar 

  10. S. Miwatashi, Y. Arikawa, E. Kotani, M. Miyamota, K.I. Naruo, H. Kimura, T. Tanaka, S. Asahi, S.J. Ohkawa, J. Med. Chem. 48, 5966–5979 (2005)

    Article  CAS  Google Scholar 

  11. C. Papadopoulou, A. Geronikaki, D. Hadjipavlou-Litina, Il Farmaco 60, 969–973 (2005)

    Article  CAS  Google Scholar 

  12. Y. Kumar, R. Green, K.Z. Borysko, D.S. Wise, L.L. Wotring, L.B. Townsend, J. Med. Chem. 36, 3843–3848 (1993)

    Article  CAS  Google Scholar 

  13. R. Pereira, C. Gaudon, B. Iglesias, P. Germain, H. Gronemeyer, A.R. De Lera, Bioorg. Med. Chem. Lett. 16, 49–54 (2006)

    Article  CAS  Google Scholar 

  14. D.S. Millan, R.H. Prager, C. Brand, P.H. Hart, Tetrahedron 56, 811–816 (2000)

    Article  CAS  Google Scholar 

  15. J. Clough, S. Chen, E.M. Gordon, C. Hackbarth, S. Lam, J. Trias, R.J. White, Q. Candiani, S. Donadio, G. Romano, R. Ciabatti, J.W. Jacobs, Bioorg. Med. Lett. 13, 3409–3414 (2003)

    Article  CAS  Google Scholar 

  16. G. Lentzen, R. Klinck, N. Matassova, F. Aboul-Ela, A.I. Murchle, Chem. Biol. 10, 769–778 (2003)

    Article  CAS  Google Scholar 

  17. P.V. Frank, K.S. Girish, B.J. Kalluraya, Chem. Sci. 119, 41–46 (2007)

    Article  CAS  Google Scholar 

  18. R.Y. Morjan, A.M. Mkadmh, I. Beadham, A.A. Elmanama, M.R. Mattar, J. Raftery, R.G. Pritchard, A.M. Awadallah, J.M. Gardiner, Bioorg. Med. Chem. Lett. 24, 5796–5800 (2014)

    Article  CAS  Google Scholar 

  19. S. Bhandari, K.G. Bothara, M.K. Raut, A.A. Patil, A.P. Sarkate, V.J. Mokale, Bioorg. Med. Chem. 16, 1822–1831 (2008)

    Article  CAS  Google Scholar 

  20. S.G. Kucukguzel, I. Kucukguzel, E. Tatar, S. Rollas, F. Sahin, M. Gulluce, E. De Clercq, L. Kabasakal, Eur. J. Med. Chem. 42, 893–901 (2007)

    Article  Google Scholar 

  21. A.A. El-Emam, O.A. Al-Deeb, M. Al-Omar, J. Lehmann, Bioorg. Med. Chem. 12, 5107–5113 (2004)

    Article  CAS  Google Scholar 

  22. F.A. Omar, M.N. Mahfouz, A.M. Rahman, Eur. J. Med. Chem. 31, 819–825 (1996)

    Article  CAS  Google Scholar 

  23. R. Franski, Asian J. Chem. 17, 2063–2075 (2005)

    CAS  Google Scholar 

  24. B. Narayana, K.K. Vijayraj, B.V. Ashalatha, N.S. Kumari, Arch. Pharm. (Weinheim) 338, 373–377 (2005)

    Article  CAS  Google Scholar 

  25. M. Amir, S. Kumar, Acta. Pharm. 57, 31–45 (2007)

    Article  CAS  Google Scholar 

  26. N.M. Bezerra, S.P. De-Oliveira, R.M. Srivastava, J.R. Da Silva, Il Farmaco 60, 955–960 (2005)

    Article  CAS  Google Scholar 

  27. B.A. Johans, Naphthyridineintegrase inhibitor. PCT, Int. Appl. Wo 101512 (2004)

  28. N.C. Desai, A.R. Trivedi, H.C. Somani, K.A. Bhatt, Chem. Biol. Drug. Des. (2014). doi:10.1111/cbdd.12502

    Google Scholar 

  29. N.C. Desai, N.R. Shihory, G.M. Kotadiya, P. Desai, Eur. J. Med. Chem. 82, 480–489 (2014)

    Article  CAS  Google Scholar 

  30. N.C. Desai, V.V. Joshi, K.M. Rajpara, A.H. Makwana, Arab. J. Chem. (2012). doi:10.1016/j.arabjc.2012.10.020

    Google Scholar 

  31. N.C. Desai, N. Bhatt, H. Somani, Med. Chem. Res. 24, 258–266 (2015)

    Article  CAS  Google Scholar 

  32. National committee for clinical laboratory, Standards Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically approved standard, 3rd ed. NCCLS Publication M7-A3, Villanova, PA (1993)

  33. National committee for clinical laboratory standards, Reference Method for Broth Dilution Antifungal Testing of Yeasts, Proposed Standard, NCCLS Document M27-P; Villanova, PA. (1992)

  34. N.C. Desai, V.V. Joshi, K.M. Rajpara, H.V. Vaghani, H.M. Satodiya, J. Fluor. Chem. 142, 67–78 (2012)

    Article  CAS  Google Scholar 

  35. N.C. Desai, K.M. Rajpara, V.V. Joshi, Bioorg. Med. Chem. Lett. 22, 6871–6875 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are thankful to the University Grants Commission, New Delhi and Department of Science and Technology, New Delhi for financial support under the NON-SAP and DST-FIST programs, respectively.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. C. Desai.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Desai, N.C., Bhatt, N., Dodiya, A. et al. Synthesis, characterization and antimicrobial screening of thiazole based 1,3,4-oxadiazoles heterocycles. Res Chem Intermed 42, 3039–3053 (2016). https://doi.org/10.1007/s11164-015-2196-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2196-x

Keywords

Navigation