Russian Journal of Bioorganic Chemistry

, Volume 45, Issue 6, pp 585–590 | Cite as

Synthesis and Biological Evaluation of Novel Steroidal 5α,8α-Endoperoxide Derivatives with Aromatic Hydrazone Side Chain as Potential Anticancer Agents

  • H. J. Wang
  • M. BuEmail author
  • J. Wang
  • L. Liu
  • S. Zhang


Seven new steroidal 5α,8α-endoperoxide derivatives with C-17 aromatic hydrazone side chain were synthesized. Structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometry. Anti-proliferative activities of the synthesized compounds were evaluated in vitro by the MTT method. Among the seven compounds, 5α,8α-epidioxy-17-(4-chloro-benzylidene)-hydrazonoandrost-3β-ol showed the strongest anti-proliferative activity against three human cancer cell lines (MCF-7, HepG2, and SK-Hep1).


steroid ergosterol peroxide dehydroepiandrosterone dihydrazone antitumor activity 



This study was supported by Qiqihar Academy of Medical Sciences Project (QMSI 2017B-09).


The work has no studies involving humans or animals as subjects of the study.

Conflict of Interests

Authors declare that they have no conflicts of interests.


  1. 1.
    Bu, M., Yang, B.B., and Hu, L.M., Curr. Med. Chem., 2016, vol. 23, pp. 383–405.CrossRefGoogle Scholar
  2. 2.
    Nowak, R., Drozd, M., Mendyk, E., Lemieszek, M., Krakowiak, O., Kisiel, W., Rzeski, W., and Szewczyk, K., Molecules, 2016, vol. 21, p. E946.CrossRefGoogle Scholar
  3. 3.
    Kim, D.H., Jung, S.J., Chung, I.S., Lee, Y.H., Kim, D.K., Kim, S.H., Kwon, B.M., Jeong, T.S., Park, M.H. Seoung, N.S., and Baek, N.I., Arch. Pharm. Res., 2005, vol. 28, pp. 541–545.CrossRefGoogle Scholar
  4. 4.
    Fang, S.T., Liu, X., Kong, N.N., Liu, S.J., and Xia, C.H., Nat. Prod. Res., 2013, vol. 27, pp. 1965–1970.CrossRefGoogle Scholar
  5. 5.
    Zhao, S., Ye, G., Fu, G., Cheng, J.X., Yang, B.B., and Peng, C., Int. J. Oncol., 2011, vol. 38, pp. 1319–1327.PubMedGoogle Scholar
  6. 6.
    Han, J., Sohn, E.J., Kim, B., Kim, S., Won, G., Yoon, S., Lee, J., Kim, M.J., Lee, H., Chung, K., and Kim, S.H., Cancer Cell Int., 2014, vol. 14, p. 117.CrossRefGoogle Scholar
  7. 7.
    Zhu, R., Zheng, R., Deng, Y., Chen, Y., and Zhang, S., Phytomedicine, 2014, vol. 21, pp. 372–378.CrossRefGoogle Scholar
  8. 8.
    Rhee, Y.H., Jeong, S.J., Lee, H.J. Lee, H.J., Koh, W., Jung, J.H., Kim, S.H., and Sung-Hoon, K., BMC Cancer, 2012, vol. 12, p. 28.CrossRefGoogle Scholar
  9. 9.
    Kobori, M., Yoshida, M., Ohnishi-Kameyama, M., and Shinmoto, H., Br. J. Pharmacol., 2007, vol. 150, pp. 209–219.CrossRefGoogle Scholar
  10. 10.
    Wu, Q.P., Xie, Y.Z., Deng, Z., Li, X.M., Yang, W., Jiao, C.W., Fang, L., Li, S.Z., Pan, H.H., Yee, A.J., Lee, D.Y., Li, C., Zhang, Z., Guo, J., and Yang, B.B., PLoS One, 2012, vol. 7. e44579.CrossRefGoogle Scholar
  11. 11.
    Li, X.M., Wu, Q.P., Bu, M., Hu, L.M., Du, W.W., Jiao, C.W., Pan, H.H., Sdiri, M., Wu, N., Xie, Y.Z., and Yang, B.B., Oncotarget, 2016, vol. 7, pp. 33 948–33 959.Google Scholar
  12. 12.
    Hanson, J.R, Nat. Prod. Rep., 2010, vol. 27, pp. 887–899.CrossRefGoogle Scholar
  13. 13.
    Shan, L.H., Liu, H.M., Huang, K.X., Dai, G.F., Cao, C., and Dong, R.J., Bioorg. Med. Chem. Lett., 2009, vol. 19, pp. 6637–6639.CrossRefGoogle Scholar
  14. 14.
    Yu, B., Zhang, E., Sun, X.N., Ren, J.L., Fang, Y., Zhang, B.L., Yu, D.Q., and Liu, H.M., Steroids, 2013, vol. 78, pp. 494–499.CrossRefGoogle Scholar
  15. 15.
    Gogoi, S., Shekarrao, K., Duarah, A., Bora, T.C., Gogoi, S., and Boruah, R.C., Steroids, 2012, vol. 77, pp. 1438–1445.CrossRefGoogle Scholar
  16. 16.
    Haubrich, B.A., Molecules, 2018, vol. 23, p. E2768.CrossRefGoogle Scholar
  17. 17.
    Słomiak, K., Łazarenkow, A., Chęcińska, L., Kusz, J., Ochocki, J., and Nawrot-Modranka, J., Molecules, 2018, vol. 17, E2067.CrossRefGoogle Scholar
  18. 18.
    Ke, S.Y., Wei, Y.H., Shi, L.Q., Yang, Q.Y., and Yang, Z.W., Anticancer Agents Med. Chem., 2013, vol. 13, pp. 1291–1298.CrossRefGoogle Scholar
  19. 19.
    Cui, J.G., Liu, L., Zhao, D.D., Gan, X., Huang, C.F., Xiao, Q., Qi, B.B., Yang, L., and Huang, Y.M., Steroids, 2015, vol. 95, pp. 32–38.CrossRefGoogle Scholar
  20. 20.
    Brunel, J.M., Loncle, C., Vidal, N., Dherbomez, M., and Letourneux, Y., Steroids, 2005, vol. 70, pp. 907–912.CrossRefGoogle Scholar
  21. 21.
    Merlani, M.I., Kemertelidze, E.P., Papadopoulos, K., and Men’shova, N.I., Bioorg. Khim., 2004, vol. 30, pp. 552–557.PubMedGoogle Scholar
  22. 22.
    Mazoir, N., Benharref, A., Bailén, M., Reina, M., and González-Coloma, A., Phytochemistry, 2008, vol. 69, pp. 1328–1338.CrossRefGoogle Scholar
  23. 23.
    Khan, S.A., Asiri, A.M., and Yusuf, M., Eur. J. Med. Chem., 2009, vol. 44, pp. 2597–2600.CrossRefGoogle Scholar
  24. 24.
    Mohamed, N.R., Elmegeed, G.A., Abd-ElMalek, H.A., and Younis, M., Steroids, 2005, vol. 70, pp. 131–136.CrossRefGoogle Scholar
  25. 25.
    Li, H. and Yang, B.B., Oncotarget, 2012, vol. 3, pp. 1653–1668.PubMedPubMedCentralGoogle Scholar
  26. 26.
    Bu, M., Cao, T.T., Li, H.X., Guo, M.Z., Yang, B.B., Zhou, Y., Zhang, N., Zeng, C.C., and Hu, L.M., Steroids, 2017, vol. 124, pp. 46–53.CrossRefGoogle Scholar
  27. 27.
    Bu, M., Cao, T.T., Li, H.X., Guo, M.Z., Yang, B.B., Zeng, C.C., and Hu. L.M., Chem. Med. Chem., 2017, vol. 12, pp. 466–474.CrossRefGoogle Scholar
  28. 28.
    Bu, M., Cao, T.T., Li, H.X., Guo, M.Z., Yang, B.B., Zhou, Y., Zhang, N., Zeng, C.C., and Hu, L.M., Bioorg. Med. Chem. Lett., 2017, vol. 27, pp. 3856–3861.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  1. 1.College of Pharmacy, Qiqihar Medical UniversityQiqiharChina
  2. 2.Basic Medical Science College, Qiqihar Medical UniversityQiqiharChina

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