Skip to main content
Log in

Synthesis and Anticancer Evaluation of 2-{4-[5-(5-Substituted arylpyrimidin-2-yl)-1H-pyrazol-3-yl]-phenyl}thiazolo[4,5-b]pyridine Derivatives

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

Abstract

In the present study a new series of 2-{4-[5-(5-substituted arylpyrimidin-2-yl)-1H-pyrazol-3-yl] phenyl}thiazolo[4,5-b]pyridine derivatives (11a–11j) are synthesized and tested for their anticancer activity against four human cancer cell lines including MCF-7 (breast), A549 (lung), Colo-205 (colon), and A2780 (ovarian) by the MTT assay. Among synthesized compounds, 11b, 11c, 11d, 11g, and 11j exhibit activity higher than the standard drug.

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.

Similar content being viewed by others

References

  1. Sun, C., Chen, C., Xu, S., Wang, J., Zhu, Y., Kong, D., Tao, H., Jin, M., Zheng, P., and Zhu, W., Bioorg. Med. Chem., 2016, vol. 24, p. 3862. doi https://doi.org/10.1016/j.bmc.2016.06.032

    Article  CAS  PubMed  Google Scholar 

  2. Desai, K., Patel, R., and Chikhalia, K., J. Ind. Chem. B, 2006, vol. 45, p. 773.

    Google Scholar 

  3. Amr, A.E., Nermien, M.S., and Abdulla, M.M., Monatsh. Chem., 2007, vol. 138, p. 699. doi https://doi.org/10.1007/s00706-007-0651-0

    Article  CAS  Google Scholar 

  4. Prakash, O., Kumar, R., Kumar, R., Tyagi, P., and Kuhad, R.C., Euro. J. Med. Chem., 2007, vol. 42, p. 868. doi https://doi.org/10.1016/j.ejmech.2006.11.019

    Article  CAS  Google Scholar 

  5. Ukrainets, I.V., Tugaibei, I.A., Bereznykova, N.L., Karvechenko, V.N., and Turov, A.V., Chem. Heterocycl. Comp., 2008, vol. 5, p. 565. doi https://doi.org/10.1007/s10593-008-0076-7

    Article  Google Scholar 

  6. Ballell, L., Field, R.A., Chung, G.A.C., and Young, R.J., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 1736. doi https://doi.org/10.1016/j.bmcl.2006.12.066

    Article  CAS  PubMed  Google Scholar 

  7. Kumar, D., Khan, S. I., Tekwani, B. L., Ponnan, P., and Rawat, D.S., Eur. J. Med. Chem., 2015, vol. 89, p. 490. doi https://doi.org/10.1016/j.ejmech.2014.10.061

    Article  CAS  PubMed  Google Scholar 

  8. Cordeu, L., Cubedo, E., Bandres, E., Rebollo, A., Saenz, X., Chozas, H., Domínguez, V.M., Echeverria, M., Mendivil, B., and Sanmartin, C., Bioorg. Med. Chem., 2007, vol. 15, p. 1659. doi https://doi.org/10.1016/j.bmc.2006.12.010

    Article  CAS  PubMed  Google Scholar 

  9. Lu, H.H., Xue, P., Zhu, Y.Y., Ju, X.L., Zheng, X.J., Zhang, X., Xiao, T., Pannecouque, C., Li, T.T., and Gu, S.X., Bioorg. Med. Chem., 2017, vol. 25, p. 2491. doi https://doi.org/10.1016/j.bmc.2017.03.009

    Article  CAS  PubMed  Google Scholar 

  10. Katiyar, S.B., Bansal, I., Saxena, J.K., and Chauhan, P.M.S., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 47. doi https://doi.org/10.1016/j.bmcl.2004.10.046

    Article  CAS  PubMed  Google Scholar 

  11. Constantine, J.W. and Hess, H.-J., Eur. J. Pharmacol., 1981, vol. 74, p. 227. doi https://doi.org/10.1016/0014-2999(81)90535-5

    Article  CAS  PubMed  Google Scholar 

  12. Malladi, S., Isloor, A.M., Isloor, S., Akhila, D.S., and Fun, H.-K., Arabian J. Chem., 2013, vol. 6, p. 335. doi https://doi.org/10.1016/j.arabjc.2011.10.009

    Article  CAS  Google Scholar 

  13. Abdel-Aziz, M., Abuo-Rahma, G.E.-D.A., and Hassan, A.A., Eur. J. Med. Chem., 2009, vol. 44, p. 3480. doi https://doi.org/10.1016/j.ejmech.2009.01.032

    Article  CAS  PubMed  Google Scholar 

  14. Ashton, W.T., Hutchins, S.M., Greenlee, W.J., Doss, G.A., Chang, R.S., Lotti, V.J., Faust, K.A., Chen, T.B., and Zingaro, G.J., J. Med. Chem., 1993, vol. 36, p. 3595. doi https://doi.org/10.1021/jm2001585

    Article  CAS  PubMed  Google Scholar 

  15. Stauffer, S.R., Huang, Y.R., Aron, Z.D., Coletta, C.J., Sun, J., Katzenellenbogen, B.S., and Katzenellenbogen, J.A., Bioorg. Med. Chem., 2001, vol. 9, p. 151. doi https://doi.org/10.1016/S0960-894X(98)00705-7

    Article  CAS  PubMed  Google Scholar 

  16. Fink, B.E., Mortensen, D.S., Stauffer, S.R., Aron, Z.D., and Katzenellenbogen, J.A., Chem. Biol., 1999, vol. 6, p. 205. doi https://doi.org/10.1016/S1074-5521(99)80037-4

    Article  CAS  PubMed  Google Scholar 

  17. Stauffer, S.R., Coletta, C.J., Tedesco, R., Nishiguchi, G., Carlson, K., Sun, J., Katzenellenbogen, B.S., and Katzenellenbogen, J.A., J. Med. Chem., 2000, vol. 43, p. 4934. doi https://doi.org/10.1021/jm000170m

    Article  CAS  PubMed  Google Scholar 

  18. Sugimoto, N., Watanabe, H., and Ide, A., Tetrahedron, 1960, vol. 11, p. 231. doi https://doi.org/10.1016/S0040-4020(01)93171-0

    Article  CAS  Google Scholar 

  19. Manikannan, R., Venkatesan, R., Muthusubramanian, S., Yogeeswari, P., and Sriram, D., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 6920. doi https://doi.org/10.1016/j.bmcl.2010.09.137

    Article  CAS  PubMed  Google Scholar 

  20. Hannah, J., Kelly, K., Patchett, A.A., Steelman, S.L., and Morgan, E.R., J. Med. Chem., 1975, vol. 18, p. 168. doi https://doi.org/10.1021/jm00236a012

    Article  CAS  PubMed  Google Scholar 

  21. Elguero, J. and Rees, C.W., Compr. Heterocycl. Chem., 1996, vol. 3, p. 1.

    CAS  Google Scholar 

  22. Bronson, J., Dhar, M., Ewing, W., and Lonberg, N., Annu. Rep. Med. Chem. 2012, vol. 47, p. 525.

    Google Scholar 

Download references

Acknowledgments

The authors would like to thank the management of the AMRI Hyderabad research Centre for giving an opportunity to carry out this research. The authors are also thankful to Mr. Ch. Ravi Kumar for providing synthesis facility.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to T. B. Rao.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Koteswara Rao, C.P., Rao, T.B., Charan, G.K. et al. Synthesis and Anticancer Evaluation of 2-{4-[5-(5-Substituted arylpyrimidin-2-yl)-1H-pyrazol-3-yl]-phenyl}thiazolo[4,5-b]pyridine Derivatives. Russ J Gen Chem 89, 1023–1028 (2019). https://doi.org/10.1134/S1070363219050244

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219050244

Keywords

Navigation