Skip to main content

Synthesis of coumarin appended pyrazolyl-1,3,4-oxadiazoles and pyrazolyl-1,3,4-thiadiazoles: Evaluation of their in vitro antimicrobial and antioxidant activities and molecular docking studies

Abstract

A series of semicarbazones, thiocarbazones, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles bearing coumarin and pyrazole moiety have been synthesized. The new synthesized compounds were screened in vitro for their antimicrobial and antioxidant activities. Preliminary studies showed that among the synthesized new compounds, chloro-substituted thiosemicarbazone showed excellent activities against all tested organisms; at the same time, methyl substituted thiosemicarbazone showed greater activity against E. coli. Chloro-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole demonstrated greater DPPH and hydroxyl radical scavenging abilities. Molecular docking studies indicate that 1,3,4-oxadiazoles and 1,3,4-thiadiazoles manifest better interaction with CAT (catalase) and GPx (glutathione peroxidase) than that with SOD (superoxide dismutase). Studies on the antimicrobial and antioxidant activities of the synthesized compounds compared with those of their starting compounds are discussed.

This is a preview of subscription content, access via your institution.

Abbreviations

CAT:

catalase

GPx:

glutathione peroxidase

DPPH:

α,α-diphenyl-β-picrylhydrazyl

SOD:

superoxide dismutase

References

  1. Charistos, C., George, K., and Chryssa, T., J. Heterocycl. Chem., 2001, vol. 38, pp. 153–158.

    Article  Google Scholar 

  2. Nagamallu, R. and Kariyappa, A.K., Bioorg. Med. Chem. Lett., 2013, vol. 23, pp. 6406–6409.

    Article  PubMed  Google Scholar 

  3. Surendra, N.P., Perumal, Y., and James, P.S., Eur. J. Med. Chem., 2000, vol. 35, pp. 879–886.

    Article  Google Scholar 

  4. Dharmarajan, S., Perumal, Y., and Rathinasabapathy, T., Bioorg. Med. Chem. Lett., 2004, vol. 14, pp. 3923–3924.

    Article  Google Scholar 

  5. Mashooq, A.B., Mohamed, A.A., and Nadeem, S., Med. Chem. Res., 2013, vol. 22, pp. 4455–4458.

    Article  Google Scholar 

  6. Adnan, A.K., Nasser, R.B., Omar, A.D., Elsayed, E.H., Tarek, M.I., and Ali, A.E., Eur. J. Med. Chem., 2007, vol. 42, pp. 235–242.

    Article  Google Scholar 

  7. Almasirad, A., Tabatabai, S.A., Faizi, M., Kebriacezadch, A., Mehrabi, N., Dalvandi, A., and Shafiee, A., Bioorg. Med. Chem. Lett., 2004, vol. 14, pp. 6057–6059.

    CAS  Article  PubMed  Google Scholar 

  8. Ajay Kumar, K., Jayaroopa, P., and Vasanth Kumar, G., Int. J. Chem. Tech. Res., 2012, vol. 4, pp. 1782–1791.

    CAS  Google Scholar 

  9. Neelam, B., Kakul, H., Gonzalez Garza, M.T., Delia, E.C., Castro Garza, J., Benito, D.M., Fehmida, N., and Amir, A., Bioorg. Med. Chem. Lett., 2002, vol. 12, pp. 3475–3478.

    Article  Google Scholar 

  10. Loiseau, P.M. and Nguyen, D.X., Trop. Med. Int. Health., 1996, vol. 1, pp. 379–384.

    CAS  Article  PubMed  Google Scholar 

  11. Charles, S.J., Sandra, H.S., John, C.D., and Daniel, L.K., Antiviral Res., 1986, vol. 6, pp. 197–222.

    Article  Google Scholar 

  12. Ajay Kumar, K., Renuka, N., and Vasanth Kumar, G., Int. J. Pharm. Tech. Res., 2013, vol. 5, pp. 239–248.

    CAS  Google Scholar 

  13. Prakash Karegoudar, D., Jagdeesh, P., Mithun, A., Manjathuru, M., Boja, P., and Bantwal, S.H., Eur. J. Med. Chem., 2008, vol. 43, pp. 808–815.

    Article  PubMed  Google Scholar 

  14. Paul, H. and Ahmed, S.A., Mutat. Res., 1988, vol. 202, pp. 363–375.

    Article  Google Scholar 

  15. Daisy, P., Suveena, S., and Cecily, R.R.L., Asian J. Pharm. Clin. Res., 2012, vol. 5, pp. 32–35.

    CAS  Google Scholar 

  16. Anne-Frances Miller., Cur. Opin. Chem. Biol., 2004, vol. 8, pp. 162–168.

    Article  Google Scholar 

  17. John Hart, P., Melinda., Balbirnie, M., Nancy, L., Ogihara., Aram, M., Nersissian., Manfred, S., Weiss., Joan, S.V., and David, E., Biochem., 1999, vol. 38, pp. 2167–2178.

    Article  Google Scholar 

  18. Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J., Adv. Drug Deliver Rev., 2001, vol. 46, pp. 3–26.

    CAS  Article  Google Scholar 

  19. Padmaja, A., Rajashekar, C., Muralikrishna, A., and Padmavathi, V., Eur. J. Med. Chem., 2011, vol. 46, pp. 5034–5038.

    CAS  Article  PubMed  Google Scholar 

  20. Renuka, N., Bharath, S., Mylarappa, B.N., and Ajay Kumar, K., Bioorg. Med. Chem. Lett., 2016, vol. 26, pp. 690–694.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. Ajay Kumar.

Additional information

The article is published in the original.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Renuka, N., Vivek, H.K., Pavithra, G. et al. Synthesis of coumarin appended pyrazolyl-1,3,4-oxadiazoles and pyrazolyl-1,3,4-thiadiazoles: Evaluation of their in vitro antimicrobial and antioxidant activities and molecular docking studies. Russ J Bioorg Chem 43, 197–210 (2017). https://doi.org/10.1134/S106816201702011X

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S106816201702011X

Keywords

  • antimicrobial
  • antioxidant
  • coumarin
  • MIC
  • molecular docking
  • pyrazole