Skip to main content
SpringerLink
Log in

Synthesis, Characterization, and Cytotoxic Evaluation of New Triazole Derivatives of Osthol

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Osthol [7-methoxy-8-(3-methylbut-2-en-1-yl)chromen-2-one] isolated from Prangos pabularia was used as a starting material for the synthesis of its various derivatives via modifications of the lactone ring. The resulting compounds were fully characterized by spectral techniques and evaluated for their anticancer activity against Hep-G2 (human hepatoma), HeLa (cervical carcinoma), U-87 (brain cancer) and MCF-7 (breast cancer) cell lines using MTT assay. All synthesized derivatives exhibited higher activity than that of osthol. Among this series, 4-bromophenyl, 3-hydroxyphenyl, and p-tolyl derivatives showed excellent cytotoxic activity against U-87 and MCF-7 cancer cell lines with IC50 values of 6–7.3 µM.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Scheme

Similar content being viewed by others

REFERENCES

  1. Ali, I., Lone, M.N., Al-Othman, Z.A., Al-Warthan, A., and Sanagi, M.M., Curr. Drug Targets, 2015, vol. 16, p. 711. https://doi.org/10.2174/1389450116666150309115922

    Article  CAS  PubMed  Google Scholar 

  2. Daniels, A.L., Slambrouck, S.V., Lee, R.K., Arguello, T.S., Browning, J., Pullin, M.J., Kornienko, A., and Steelant, W.F., Oncol. Rep., 2006, vol. 15, p. 1327. https://doi.org/10.3892/or.15.5.1327

    Article  PubMed  Google Scholar 

  3. Hoult, J.R. and Payá, M., Vasc. Pharmacol., 1996, vol. 27, p. 713. https://doi.org/10.1016/0306-3623(95)02112-4

    Article  CAS  Google Scholar 

  4. Setzer, W.N., Setzer, M.C., Schmidt, J.M., Moriarity, D.M., Vogler, B., Reeb, S., Holmes, A.M., and Haber, W.A., Planta Med., 2000, vol. 66, p. 493. https://doi.org/10.1055/s-2000-8595

    Article  CAS  PubMed  Google Scholar 

  5. Garcia-Argaez, A.N., Apan, T.O.R., Delgado, H.P., Velázquez, G., and Vázquez, M.M., Planta Med., 2000, vol. 66, p. 279. https://doi.org/10.1055/s-0029-1243137

    Article  CAS  PubMed  Google Scholar 

  6. Schimmer, O. and Abel, G., Mutat. Res., 1986, vol. 169, p. 47. https://doi.org/10.1016/0165-1218(86)90017-0

    Article  CAS  PubMed  Google Scholar 

  7. Appendino, G., Bianchi, F., Bader, A., Campagnuolo, C., Fattorusso, E., Taglialatela-Scafati, O., Molina, M.B., Macho, A., Fiebich, B.L., Bremner, P., Heinrich, M., Ballero, M., and Muñoz, E., J. Nat. Prod., 2004, vol. 23, p. 532. https://doi.org/10.1021/np0340652

    Article  CAS  Google Scholar 

  8. Tada, Y., Shikishima, Y., Takaishi, Y., Shibata, H., Higuti, T., Honda, G., Ito, M., Takeda, Y., Kodzhimatov, O.K., Ashurmetov, O., and Ohmoto, Y., Phytochemistry, 2002, vol. 59, p. 649. https://doi.org/10.1016/S0031-9422(02)00023-7

    Article  CAS  PubMed  Google Scholar 

  9. Musa, M.A., Cooperwood, J.S., and Khan, M.O., Curr. Med. Chem., 2008, vol. 15, p. 2664. https://doi.org/10.2174/092986708786242877

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Borges, F., Roleira, F., Milhazes, N., Santana, L., and Uriarte, E., Curr. Med. Chem., 2005, vol. 12, p. 887. https://doi.org/10.2174/0929867053507315

    Article  CAS  PubMed  Google Scholar 

  11. Kostova, I., Raleva, S., Genova, P., and Argirova, R., Bioinorg. Chem. Appl., 2006, vol. 2006, article ID 068274. https://doi.org/10.1155/BCA/2006/68274

  12. Okamoto, T., Kobayashi, T., and Yoshida, S., Curr. Med. Chem.: Anti-Cancer Agents, 2005, vol. 5, p. 47. https://doi.org/10.2174/1568011053352622

    Article  CAS  PubMed  Google Scholar 

  13. Weber, U.S., Steffen, B., and Siegers, C.P., Res. Commun. Mol. Pathol. Pharmacol., 1998, vol. 99, p. 193.

    CAS  PubMed  Google Scholar 

  14. Tang, C.H., Yang, R.S., Chien, M.Y., Chen, C.C., and Fu, W.M., Eur. J. Pharmacol., 2008, vol. 28, p. 40. https://doi.org/10.1016/j.ejphar.2007.10.013

    Article  CAS  Google Scholar 

  15. Okamoto, T., Kobayashi, T., and Yoshida, S., Med. Chem., 2007, vol. 3, p. 35. https://doi.org/10.2174/157340607779317607

    Article  CAS  PubMed  Google Scholar 

  16. Zhang, Q., Qin, L., He, W., Puyvelde, L.V., Maes, D., Adams, A., Zheng, H., and Kimpe, N.D., Planta Med., 2007, vol. 73, p. 13. https://doi.org/10.1055/s-2006-951724

    Article  CAS  PubMed  Google Scholar 

  17. Matsuda, H., Ido, Y., Hirata, A., Ino, Y., Naruto, S., Amamiya, T., and Kubo, M., Biol. Pharm. Bull., 2002, vol. 25, p. 260. https://doi.org/10.1248/bpb.25.260

    Article  CAS  PubMed  Google Scholar 

  18. Huang, R., Chen, C., Huang, Y., Hsieh, D., Hu, C., Chen, C., and Chang, C., Hepatology, 1996, vol. 24, p. 508. https://doi.org/10.1053/jhep.1996.v24.pm0008781315

    Article  CAS  PubMed  Google Scholar 

  19. Okamoto, T., Kawasaki, T., and Hino, O., Biochem. Pharmacol., 2003, vol. 65, p. 677. https://doi.org/10.1016/S0006-2952(02)01606-4

    Article  CAS  PubMed  Google Scholar 

  20. Kuo, P.L., Hsu, Y.L., Chang, C.H., and Chang, J.K., J. Pharmacol. Exp. Ther., 2005, vol. 314, p. 1290. https://doi.org/10.1124/jpet.105.085092

    Article  CAS  PubMed  Google Scholar 

  21. Li, X.X., Hara, I., and Matsumiya, T., Biol. Pharm. Bull., 2002, vol. 25, p. 738. https://doi.org/10.1248/bpb.25.738

    Article  CAS  PubMed  Google Scholar 

  22. Farooq, S., Banday, J.A., Hussain, A., Nazir, M., Qurishi, M.A., Hamid, A., and Koul, S., Med. Chem., 2019, vol. 15, p. 138. https://doi.org/10.2174/1573406414666180911161047

    Article  CAS  PubMed  Google Scholar 

  23. Kandhasamy, S., Perumal, S., Madhan, B., Umamaheswari, N., Banday, J.A., Perumal, P.T., and Santhanakrishnan, V.P., ACS Appl. Mater. Interfaces, 2017, vol. 9, p. 8556. https://doi.org/10.1021/acsami.6b16488

    Article  CAS  PubMed  Google Scholar 

  24. Farozi, A., Shah, S.A., and Banday, J.A., Optik, 2016, vol. 127, p. 2802. https://doi.org/10.1016/j.ijleo.2015.11.224

    Article  CAS  Google Scholar 

  25. Banday, J.A., Mir, F.A., Farooq, S., Qurishi, M.A., Koul, S.K., and Razdan, T.K., Am. J. Anal. Chem., 2012, vol. 3, p. 204. https://doi.org/10.4236/ajac.2012.33029

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are thankful to Director NIT Srinagar for providing all types of facilities. Z.K. Rather also acknowledges Ministry of Human Resource Development (MHRD, New Delhi) for providing the Institute fellowship to carry out this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology Srinagar, 190006, Srinagar, Jammu and Kashmir, India

    Z. K. Rather, J. A. Banday & H. N. Chisti

Authors
  1. Z. K. Rather
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. A. Banday
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. N. Chisti
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Z. K. Rather.

Ethics declarations

The authors declare no conflict of interest.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rather, Z.K., Banday, J.A. & Chisti, H.N. Synthesis, Characterization, and Cytotoxic Evaluation of New Triazole Derivatives of Osthol. Russ J Org Chem 57, 986–993 (2021). https://doi.org/10.1134/S1070428021060154

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021060154

Keywords:

Search

Navigation