Skip to main content
SpringerLink
Log in

Synthesis and Cytotoxicity of Indole Derivatives of Betulin, Erythrodiol, and Uvaol

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

Abstract

2,3-Indolotriterpenic alcohols have been synthesized for the first time by successive modification of 3-oxo triterpenic acids (Fisher reaction, reduction of С17-СOOH, cyanoethylation) and characterized by physicochemical methods of analysis. It has been found that 2,3-indolouvaol and 2,3-indolo-28-cyanoethoxybetulin exhibit antitumor activity in vitro toward NCI-H522 lung cancer (–12.65%) and COLO 205 colon cancer cells (–42.78%), respectively. The activity of 2,3-indolooleanolic and 2,3-indolobetulinic acids toward 19 and 9 cell lines of six and four human cancers, respectively, has been revealed. Indole-fused triterpenoids have been shown to hold promise as objects in the search for novel antitumor agents.

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

Similar content being viewed by others

References

  1. Bhandari, P.P., Patel, N.K., Gangwal, R.P., Sangamwar, A.T., and Bhutani, K.K., Bioorg. Med. Chem. Lett., 2014, vol. 24, pp. 4114–4119.

    Article  PubMed  CAS  Google Scholar 

  2. Bhandari, P.P., Patel, N.K., and Bhutani, K.K., Bioorg. Med. Chem. Lett., 2014, vol. 24, pp. 3596–3599.

    Article  PubMed  CAS  Google Scholar 

  3. Haavikko, R., Nasereddin, A., Sacerdoti-Sierra, N., Kopelyanskiy, D., Alakurtti, S., Tikka, M., Jaffe, C.L., and Ylikauhaluoma, J., Med. Chem. Communs., 2014, vol. 5, pp. 445–451.

    Article  CAS  Google Scholar 

  4. Khusnutdinova, E.F., Smirnova, I.E., Giniyatullina, G.V., Medvedeva, N.I., Yamansarov, E.Y., Kazakov, D.V., Kazakova, O.B., Linh, P.T., Viet, D.Q., and Huong, D.T., Nat. Prod. Communs., 2016, vol. 11, pp. 33–35.

    Google Scholar 

  5. Khusnutdinova, E.F., Smirnova, I.E., Kazakova, O.B., Petrova, A.V., Nguyen, T.T.H., and Viet, D.Q., Med. Chem. Res., 2017. vol. 26, pp. 2737–2742. doi 10.1007/s00044-017-1972-0

    Article  CAS  Google Scholar 

  6. Qiu, W.-W., Shen, Q., Yang, F., Wang, B., Zou, H., Li, J.-Y., Li, J., and Tang, J., Bioorg. Med. Chem. Lett., 2009, vol. 19, pp. 6618–6622.

    Article  PubMed  CAS  Google Scholar 

  7. Suman, P., Patel, A., Solano, L., Jampan, G., Gardner, Z.S., Holt, G.M., and Jonnalagadda, S.C., Tetrahedron, 2017, vol. 73, pp. 4214–4226.

    Article  CAS  Google Scholar 

  8. Hussain, H., Green, I.R., Ali, I., Khan, I.A., Ali, Z., Al-Sadi, A.M., and Ahmed, I., Expert Opin. Ther. Pat., 2017, vol. 27, pp. 1061–1072.

    Article  PubMed  CAS  Google Scholar 

  9. Kumar, V., Rani, N., Aggarwal, P., Sanna, V.K., Singh, A.T., Jaggi, M., Joshi, N., Sharma, P.K., Irchhaiya, R., and Burman, A.C., Med. Chem. Lett., 2008, vol. 18, pp. 5058–5062.

    Article  CAS  Google Scholar 

  10. Gu, W., Hao, Y., Zhang, G., Wang, S.-F., Miao, T.-T., and Zhang, K.-P., Bioorg. Med. Chem. Lett., 2015, vol. 25, pp. 554–557.

    Article  PubMed  CAS  Google Scholar 

  11. Finlay, H.J., Honda, T., and Gribble, G.W., ARKIVOC, 2002, vol. 12, pp. 38–46.

    Google Scholar 

  12. Tolstikov, G.A., Kim, Kh.-O., and Goraev, M.I., Zh. Obshch. Khim., 1967, vol. 37, p. 1960.

    Google Scholar 

  13. Kim, Kh.-O., Tolstikov, G.A., Shutov, I.P., and Nasonova, A.M., Zh. Obshch. Khim., 1969, vol. 5, pp. 1987–1991.

    CAS  Google Scholar 

  14. Giniyatyllina, G.V., Smirnova, I.E., Kazakova, O.B., Yavorskaya, N.P., Golubeva, I.S., Zhukova, O.S., Pugacheva, R.B., Apryshko, G.N., and Poroikov, V.V., Med. Chem. Res., 2015, vol. 24, pp. 3423–3436.

    Article  CAS  Google Scholar 

  15. Alley, M.C., Scudiero, D.A., Monks, P.A., Hursey, M.L., Czerwinski, M.J., Fine, D.L., Abbott, B.J., Mayo, J.G., Shoemaker, R.H., and Boyd, M.R., Cancer Res., 1988, vol. 48, pp. 589–601.

    PubMed  CAS  Google Scholar 

  16. Grever, M.R., Schepartz, S.A., and Chabner, B.A., Semin. Oncol., 1992, vol. 19, pp. 622–638.

    PubMed  CAS  Google Scholar 

  17. Boyd, M.R. and Paull, K.D., Drug Dev. Res., 1995, vol. 34, pp. 91–109.

    Article  CAS  Google Scholar 

  18. Shoemaker, R.H., Nature Rev., 2006, vol. 6, pp. 813–823.

    CAS  Google Scholar 

  19. Filimonov, D.A. and Poroikov, V.V., Ros. Khim. Zh., 2006, vol. L, pp. 66–75.

    Google Scholar 

  20. Filimonov, D.A. and Poroikov, V.V., in Chemoinformatics Approaches to Virtual Screening, Varnek, A. and Tropsha, A., Eds., RSC Publishing, 2008, pp. 182–216.

  21. Filimonov, D.A., Lagunin, A.A., Gloriozova, T.A., Rudik, A.V., Druzhilovskii, D.S., Pogodin, P.V., and Poroikov, V.V., Chem. Heterocycl. Compd., 2014, vol. 50, no. 3, pp. 444–457.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Russian Academy of Sciences, Ufa, 450054, Russia

    E. F. Khusnutdinova & O. B. Kazakova

  2. Bashkir State University, Ufa, 450076, Russia

    A. V. Petrova & O. S. Kukovinets

  3. Blokhin Russian Oncological Research Center, Moscow, 115478, Russia

    G. N. Apryshko

Authors
  1. E. F. Khusnutdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Petrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. N. Apryshko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. S. Kukovinets
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. B. Kazakova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. F. Khusnutdinova.

Additional information

Original Russian Text © E.F. Khusnutdinova, A.V. Petrova, G.N. Apryshko, O.S. Kukovinets, O.B. Kazakova, 2018, published in Bioorganicheskaya Khimiya, 2018, Vol. 44, No. 3, pp. 316–324.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khusnutdinova, E.F., Petrova, A.V., Apryshko, G.N. et al. Synthesis and Cytotoxicity of Indole Derivatives of Betulin, Erythrodiol, and Uvaol. Russ J Bioorg Chem 44, 322–329 (2018). https://doi.org/10.1134/S1068162018030081

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162018030081

Keywords

Search

Navigation