Skip to main content
Log in

Synthesis and antimicrobial activity of new 1,3,4-thiadiazoles containing oxadiazole, thiadiazole and triazole nuclei

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

A new series of 1,3,4-thiadiazole derivatives containing oxadiazole (3a – 3e), thiadiazole (4a – 4e), and triazole (5a – 5e) moieties have been prepared using 2-(5-phenyl-1,3,4-thiadiazol-2-ylamino)acetic acid (2) as intermediate. The structures of newly synthesized compounds are confirmed by 1H NMR, 13C NMR, and FT-IR spectroscopy, LC/MS mass spectrometry, and elemental analysis data. Furthermore, all the newly synthesized compounds were also tested for their in vitro antibacterial activity against selected human pathogens viz. Escherichia coli, Salmonella typhimurium, Legionella monocytogenes, Klebsiella pneumonia, Salmonella typhi, Staphylococcus aureus and Bacillus subtilis and antifungal activity against Candida albicans, Streptococcus pyogenes and Fusarium solani strains. The preliminary results revealed that certain compounds exhibited promising antimicrobial activities against the test microorganisms. Nine of the total of 15 compounds exhibited excellent antibacterial activity and antifungal activity.

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.

Scheme I

Similar content being viewed by others

References

  1. S. Maddila and S. B. Jonnalagadda, Arch. Pharm. Chem. Life Sci., 345, 163–168 (2012).

    Article  CAS  Google Scholar 

  2. S. Maddila and S. B. Jonnalagadda, Lett. Drug Design Disc., 9 (2012) [in press].

  3. F. A. Ashour, N. S. Habib, M. El-Taibbi, et al., Farmaco, 45, 1341–1349 (1990).

    PubMed  CAS  Google Scholar 

  4. N. S. Habib, R. Soliman, F. A. Ashour and M. El-Taiebi, Pharmazie, 52, 844–847 (1997).

    PubMed  CAS  Google Scholar 

  5. S. M. Badr and R. M. Barwa, Bioorg. Med. Chem., 19, 4506–4512 (2011).

    Article  PubMed  CAS  Google Scholar 

  6. S. A. El-Dine, F. H. Jawad and N. F. Mahmoud, Pharmazie, 32, 101–103 (1984).

    Google Scholar 

  7. A. Vedani and E. F. Jr. Meyer, J. Pharm. Sci., 73, 352–358 (1984).

    Article  PubMed  CAS  Google Scholar 

  8. A. F. Atta, O. O. Farahat, A. Z. Ahmed and M. G. Marei, Molecules, 16, 5496–5506 (2011).

    Article  PubMed  CAS  Google Scholar 

  9. P. Zoumpoulakis, Ch. Camoutsis, G. Pairas, et al., Bioorg. Med. Chem., 20, 1569–1583 (2012).

    Article  PubMed  CAS  Google Scholar 

  10. J. Matysiak and Z. Malinski, Bioorg. Khim., 33, 640–647 (2007) [Russ. J. Bioorg. Chem., 33, 594 (2012)].

  11. F. Liu, X. Q. Luo, B. A. Song, et al., Bioorg. Med. Chem., 16, 3632–3640 (2008).

    Article  PubMed  CAS  Google Scholar 

  12. N. T. Klip, G. Capan, A. Gursoy, et al., J. Enzyme. Inhib. Med. Chem., 25, 126–131 (2010).

    Article  PubMed  Google Scholar 

  13. K. G. Andanappa, N. N. Malleshappa and K. V. Rajshekhar, Bioorg. Med. Chem., 12, 5651–5659 (2004).

    Article  Google Scholar 

  14. A. Foroumadi, F. Soltani, R. Jabini, et. al., Arch. Pharm. Res., 27, 502–506 (2004).

    Article  PubMed  CAS  Google Scholar 

  15. F. P. Invidiata, D. Simoni, P. Scintu and N. Pinna, Farmaco II, 51, 659–664 (1996).

    CAS  Google Scholar 

  16. N. A. Al-Masoudi, Y. A. Al-Soud and W. A. Al-Masoudi, Nucleosides, Nucleotides, Nucleic Acids, 23, 1739–1749 (2004).

    Article  PubMed  CAS  Google Scholar 

  17. Z. Chen, W. Xu, L. Liu, S., et al., Molecules, 15, 9046–9056 (2010).

    Article  PubMed  CAS  Google Scholar 

  18. M. H. Shih and F. Y. Ke, Bioorg. Med. Chem., 12, 4633–4643 (2004).

    Article  PubMed  CAS  Google Scholar 

  19. I. Khan, S. Ali, S. Hameed, N. H. Rama, et al., Eur. J. Med. Chem., 45, 5200–5207 (2010).

    Article  PubMed  CAS  Google Scholar 

  20. K. Miyamoto, R. Koshiura, M. Mori, et al., Chem. Pharm. Bull., 33, 5126–5129 (1985).

    Article  PubMed  CAS  Google Scholar 

  21. M. N. Noolvi, H. M. Patel, N. Singh, et al., Eur. J. Med. Chem., 46, 4411–4418 (2011).

    Article  PubMed  CAS  Google Scholar 

  22. Z. Luo, B. Chen, S. He, et al., Bioorg. Med. Chem. Lett., 22, 3191–3193 (2012).

    Article  PubMed  CAS  Google Scholar 

  23. A. K. Shakya, P. Mishra, G. K. Patnaik, et al., Arch. Pharm. Res., 21, 753–758 (1998).

    Article  PubMed  CAS  Google Scholar 

  24. N. Chidananda, B. Poojary, V. Sumangala, et al., Eur. J. Med. Chem., 51, 124–136 (2012).

    Article  PubMed  CAS  Google Scholar 

  25. A. Gupta, P. Mishra, S. N. Pandeya, et al., Eur. J. Med. Chem., 44, 1100–1105 (2009).

    Article  PubMed  CAS  Google Scholar 

  26. X. Q. Deng, Z. Q. Dong, M. X. Song, et al., Arch. Pharm (Weinheim) (2012); doi: 10.1002/ardp.201100326.

  27. Performance Standards for Antimicrobial Susceptibility Test, 9th Intern. Suppl. (National Committee for Clinical Laboratory Standards (NCCLS), Wayne, PA, 1999).

Download references

Acknowledgements

The authors acknowledge financial support from the University of KwaZulu-Natal in the form of laboratory facilities and postdoctoral bursary to one of the authors (S. M.).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sreekanth B. Jonnalagadda.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Maddila, S., Jonnalagadda, S.B. Synthesis and antimicrobial activity of new 1,3,4-thiadiazoles containing oxadiazole, thiadiazole and triazole nuclei. Pharm Chem J 46, 661–666 (2013). https://doi.org/10.1007/s11094-013-0865-x

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-013-0865-x

Keywords

Navigation