Russian Journal of General Chemistry

, Volume 87, Issue 12, pp 3023–3028 | Cite as

Synthesis, Antitumor Activity, and Docking Study of 1,3-Disubstituted Imidazolium Derivatives

Letters to the Editor
  • 3 Downloads

Abstract

A series of 1,3-disubstituted imidazolium salts were synthesized through a convenient synthetic approach based on the reaction of 1,4-diazabuta-1,3-dienes with HClO4. Their antitumor activity was evaluated in vitro against a number of human cancer cells. 1,3-Bis[(3,5-bis(trifluoromethyl)phenyl]imidazolium perchlorate turned out to be the most active against A549 and MCF-7 cancer cell lines with IC50 values of 5.24 and 4.21 μM, respectively. The results of structure–activity relationship study indicated that substituents on the imidazole derivatives play an important role in their cytotoxic activities. Finally, molecular docking of some tested compounds was carried out in order to investigate their binding pattern with the CDK2.

Keywords

N,N′-substituted imidazolium salt antitumor activity in vitro molecular docking 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Alberto, E.E., Rossato, L.L., Alves, S.H., Alves, D., and Braga, A.L., Org. Biomol. Chem., 2011, vol. 9, p. 1001. doi 10.1039/C0OB01010CCrossRefGoogle Scholar
  2. 2.
    Vik, A., Hedner, E., Charnock, C., Tangen, L.W., Samuelsen, Ø., Larsson, R., Bohlin, L., and Gundersen, L.-L., Bioorg. Med. Chem., 2007, vol. 15, p. 4016. doi 10.1016/j.bmc.2007.03.086CrossRefGoogle Scholar
  3. 3.
    Wang, D., Richter, C., Rühling, A., Hüwel, S., Glorius, F., and Galla, H.-J., Biochem. Biophys. Res. Commun., 2015, vol. 467, p. 1033. doi 10.1016/j.bmc.2007.03.086CrossRefGoogle Scholar
  4. 4.
    Xu, X.-L., Yu, C.-L., Chen, W., Li, Y.-C., Yang, L.-J., Li, Y., Zhang, H.-B., and Yang, X.-D., Org. Biomol. Chem., 2015, vol. 13, p. 1550. doi 10.1039/C4OB02385DCrossRefGoogle Scholar
  5. 5.
    Zhou, B., Liu, Z.-F., Deng, G.-G., Chen, W., Li, M.-Y., Yang, L.-J., Li, Y., Yang, X.-D., and Zhang, H.-B., Org. Biomol. Chem., 2016, vol. 14, p. 9423. doi 10.1039/C6OB01495JCrossRefGoogle Scholar
  6. 6.
    Dominianni, S.J. and Yen, T.T., J. Med. Chem., 1989, vol. 32, p. 2301. doi 10.1021/jm00130a013CrossRefGoogle Scholar
  7. 7.
    Fortuna, C.G., Barresi, V., Berellini, G., and Musumarra, G., Bioorg. Med. Chem., 2008, vol. 16, p. 4150. doi 10.1016/j.bmc.2007.12.042CrossRefGoogle Scholar
  8. 8.
    Castonguay, A., Doucet, C.D., Juhas, M., and Maysinger, D., J. Med. Chem., 2012, vol. 55, p. 8799. doi 10.1021/jm301103yCrossRefGoogle Scholar
  9. 9.
    Cui, B., Zheng, B. L., He, K., and Zheng, Q.Y., J. Nat. Prod., 2003, vol. 66, p. 1101. doi 10.1021/np030031iCrossRefGoogle Scholar
  10. 10.
    Zeng, X., Yang, X., Zhang, Y., Qing, C., and Zhang, H., Bioorg. Med. Chem. lett., 2010, vol. 20, p. 1844. doi 10.1016/j.bmcl.2010.01.163CrossRefGoogle Scholar
  11. 11.
    Xin, H.-X., Liu, Q., Yan, H., and Song, X.-Q., Can. J. Chem., 2013, vol. 91, p. 442. doi 10.1139/cjc-2012-0497CrossRefGoogle Scholar
  12. 12.
    He, J.-Y., Xin, H.-X., Yan, H., Song, X.-Q., and Zhong, R.-G., Ultrason. Sonochem., 2011, vol. 18, p. 466. doi 10.1016/j.ultsonch.2010.08.002CrossRefGoogle Scholar
  13. 13.
    Xin, H.-X., Zhu, X.-H., Yan, H, and Song, X.-Q., J. Heterocycl. Chem., 2016, vol. 53, p. 1363. doi 10.1002/jhet.1847CrossRefGoogle Scholar
  14. 14.
    Ranke, J., Stolte, S., Störmann, R., Arning, J., and Jastorff, B., Chem. Rev., 2007, vol. 107, p. 2183. doi 10.1021/cr050942sCrossRefGoogle Scholar
  15. 15.
    Jahn, S.C., Corsino, P.E., Davis, B.J., Law, M.E., Nørgaard, P., and Law, B.K., J. Cell Sci., 2013, vol. 126, p. 1207. doi 10.1242/jcs.117382CrossRefGoogle Scholar
  16. 16.
    Rath, S.L. and Senapati, S., Biochemistry, 2014, vol. 53, p. 4612. doi 10.1021/bi5004052CrossRefGoogle Scholar
  17. 17.
    Sun, M., Jiang, R., Wang, G., Zhang, C., Li, J., Jin, C., and Zhang, X., Int. J. Oncol., 2013, vol. 42, p. 1376. doi 10.3892/ijo.2013.1813CrossRefGoogle Scholar
  18. 18.
    Galimberti, F., Thompson, S.L., Liu, X., Li, H., Memoli, V., Green, S.R., DiRenzo, J., Greninger, P., Sharma, S.V., and Settleman, J., Clin. Cancer Res., 2010, vol. 16, p. 109. doi 10.1158/1078-0432CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  1. 1.College of Life Science and BioengineeringBeijing University of TechnologyBeijingChina

Personalised recommendations