Skip to main content

Advertisement

Log in

Synthesis and Cytotoxicity Against Human Breast Carcinoma Cell Evaluation of Some New 3,4-Disubstituted Coumarin Derivatives

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

A novel series of 3,4-disubstitutued coumarin derivatives have been synthesized by the reaction of ethyl coumarin-3-carboxylate with pyrazole-3,5-dione and condensation of ethyl 7-hydroxycoumarin-3-carboxylate with 4,6-dibromo-3-amino phenol. Acylation with acetic anhydride and condensation of coumarin derivatives with 2-hydroxybenzaldehyde yielded the corresponding acetyl derivatives and 4-substituted pyrazole derivatives. Structures of the synthesized compounds were elucidated by spectral methods and elemental analysis. All the prepared derivatives were evaluated for their cytotoxicity against human breast carcinoma cell line (MCF-7). Compound VI showed the least IC50 value in MTT colorimetric assay as compared to that of the standard marketed drug staurosporin.

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.

Institutional subscriptions

Scheme 1
Chart 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. P. Roschger, W. Fiala, and W. Stadlbauer, J. Heterocycl. Chem., 29, 225 (1992).

    Article  CAS  Google Scholar 

  2. G. Daidone, B. Maggio, D. Raffa, et al., II Farmaco, 59, 413 (2004).

    Article  CAS  Google Scholar 

  3. L-C. Chou, L-S. Huang, J.-S. Yang, et al., Bioorg. Med. Chem., 15, 1732 (2007).

    Article  CAS  Google Scholar 

  4. F. Manetti, C. Brullo, M. Magnani, et al., J. Med. Chem., 51, 1252 (2008)

    Article  CAS  Google Scholar 

  5. J. Li, Y. F. Zhao, X. L. Zhao, et al., Arch. Pharm. Chem. Life Sci., 339, 593 (2006).

    Article  CAS  Google Scholar 

  6. Y. Xia, Z.-W. Dong, B.-X. Zhao, et al., Biorg. Med. Chem., 15, 6893 (2007).

    Article  CAS  Google Scholar 

  7. Y. Xia, C.-D. Fan, B.-X. Zhao, J. Zhao, Eur. J. Med. Chem., 43, 2347 (2008).

    Article  CAS  Google Scholar 

  8. A. M. Farag, A. S. Mayhoub, S. E. Barakat, and A. H. Bayomi, Bioorg. Med. Chem., 16, 881 (2008).

    Article  CAS  Google Scholar 

  9. S. Schenone, O. Bruno, A. Ranise, et al., Bioorg. Med. Chem. Lett., 14, 2511 (2004).

    Article  CAS  Google Scholar 

  10. G. Daidone, D. Raffa, B. Maggio, et al., Eur. J. Med. Chem., 39, 219 (2004).

    Article  CAS  Google Scholar 

  11. N. C. Warshakoon, S. Wu, A. Boyer, et al., Bioorg. Med. Chem. Lett., 16, 5687 (2006).

    Article  CAS  Google Scholar 

  12. S. Huang, R. Lin, Y. Yu, et al., Bioorg. Med. Chem. Lett., 17, 1243 (2007).

    Article  CAS  Google Scholar 

  13. G. D. Zhu, J. Gong, V. B. Gandhi, et al., Bioorg. Med. Chem., 15, 2441 (2007).

    Article  CAS  Google Scholar 

  14. M. Alipour, M. Khoobi, S. Emami, et al., DARU J. Pharm. Sci., 22, 10 (2014).

    Article  Google Scholar 

  15. I. Kostova, S. Bhatia, P. Grigorov, et al., Curr. Med. Chem., 18, 3929 (2011).

    Article  CAS  Google Scholar 

  16. X. M. Peng, G. L. V. Damu, and Ch-He Zhou, Curr. Pharm. Des., 19, 3884 (2013).

  17. D. A. Ostrov, J. A. Hernández Prada, P. E. Corsino, et al., Antimicrob. Agents Chemother., 51, 3688 (2007).

    Article  CAS  Google Scholar 

  18. A. Manvar, A. Bavishi, A. Radadiya, et al., Bioorg. Med. Chem. Lett., 21, 4728 (2011).

    Article  CAS  Google Scholar 

  19. S. Emami, A. Foroumadi, M. A. Faramarzi, Arch. Pharm. Chem. Life Sci., 341, 42 (2008).

    Article  CAS  Google Scholar 

  20. R. V. Nair, E. P. Fisher, S. H. Safe, et al., Carcinogenesis, 12, 65 (1991).

    Article  CAS  Google Scholar 

  21. B. Yuce, O. Danis, A. Ogan, et al., Arzneim.-Forsch. Drug Res., 59, 129 (2009).

    CAS  Google Scholar 

  22. K. V. Sashidhara, A. Kumar, M. Chatterjee, et al., Bioorg. Med. Chem. Lett., 21, 1937 (2011).

    Article  CAS  Google Scholar 

  23. S. F. Razavi, M. Khoobi, H. Nadri, et al., Eur. J. Med. Chem,. 64, 252 (2013).

    Article  CAS  Google Scholar 

  24. A. Asadipour, M. Alipour, M. Jafari, et al., Eur. J. Med. Chem., 70, 623 (2013).

    Article  CAS  Google Scholar 

  25. M. Alipour, M. Khoobi, A. Moradi, et al., Eur. J. Med. Chem., 82, 536 (2014).

    Article  CAS  Google Scholar 

  26. S. M. Bagheri, M. Khoobi, H. Nadri, et al., Chem. Biol. Drug. Res., 86, 1215 (2015).

    Article  CAS  Google Scholar 

  27. M. Campos-Toimil, F. Orallo, L. Santana, and E. Uriarte, Bioorg. Med. Chem. Lett., 12, 783 (2002).

    Article  CAS  Google Scholar 

  28. D. Sigh and D. P. Pathak Anjali, Int. J. Pharm. Sci. Res., 7, 482 (2016).

    Google Scholar 

  29. J. Klenkar and M. Molnar, J. Chem. Pharm. Res., 7, 1223 (2015).

    CAS  Google Scholar 

  30. J. Marco-Contelles, E. Pérez-Mayoral, and P. Ballesteros, CHEC III, 199 (2008).

    Google Scholar 

  31. I. M. El-Deen, M. S. A. Elgareib, A. R. E. Mahdy, and M. S. Saleem, Mens. Agitat., 13, 10 (2018).

    Google Scholar 

  32. M. K. Shim, H. Y. Yoon, S. Lee, M. K. Jo, et al.. Sci. Rep., 7, 16635 (2017).

    Article  Google Scholar 

Download references

Acknowledgements

The authors are thankful to nuclear magnetic resonance lab in faculty of pharmacy, Mansoura University and nuclear magnetic resonance lab in Beni-suef University for using their laboratory equipments during this work.

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain any studies involving human participants or animals performed by any of the authors in this work.

CONFLICT OF INTERESTS

The authors declare that they have no conflicts of interest.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Eman M. Radwan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Radwan, E.M., Elsayed, E.H., El-Moneim, M.A. et al. Synthesis and Cytotoxicity Against Human Breast Carcinoma Cell Evaluation of Some New 3,4-Disubstituted Coumarin Derivatives. Pharm Chem J 55, 1040–1049 (2022). https://doi.org/10.1007/s11094-021-02535-5

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-021-02535-5

Keywords

Navigation