Skip to main content
SpringerLink
Log in

Synthesis and cytotoxicity of new alkyne derivatives of pentacyclic triterpenoids

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Pentacyclic triterpene hydroxy acids were transformed into acetylene-containing derivatives: propargyl esters at the carboxy group and O-(hex-5-ynoyl) derivatives at the hydroxy group. The cytotoxicity of the synthesized compounds was examined against HepG2 and Huh7 hepatocarcinoma cells and PC3 prostate cancer cells. The primary analysis of the structure—activity relationships was performed; glycyrrhetic acid derivatives showed the maximum enhancement in the cytotoxic properties upon introduction of an alkyne moiety.

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. H. Chen, Y. Gao, A. Wang, X. Zhou, Y. Zheng, J. Zhou, Eur. J. Med. Chem., 2015, 92, 648.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. R. Csuk, Expert Opin. Ther. Pat., 2014, 24, 913.

    Article  CAS  PubMed  Google Scholar 

  3. M. Chudzik, I. Korzonek-Szlacheta, W. Król, Molecules, 2015, 20, 1610.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Ł. Woźniak, S. Skąpska, K. Marszałek, Molecules, 2015, 20, 20614.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. H. Chen, Y. Gao, A. Wang, X. Zhou, Y. Zheng, J. Zhou, Eur. J. Med. Chem., 2015, 92, 648.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. S. Xiao, Zh. Tian, Y. Wang, L. Si, L. Zhang, D. Zhou, Med. Res. Rev., 2018, 38, 951.

    Article  PubMed  PubMed Central  Google Scholar 

  7. R. Paduch, M. Kandefer-Szerszen, Mini-Rev. Org. Chem., 2014, 11, 262.

    Article  CAS  Google Scholar 

  8. J. A. Jesus, J. H. G. Lago, M. D. Laurenti, E. S. Yamamoto, L. F. D. Passero, Evidence-Based Complementary Altern. Med., 2015, Art. ID 620472; DOI: 10.1155/2015/620472.

    Google Scholar 

  9. H. Hussain, I. R. Green, I. Ali, I. A. Khan, Z. Ali, A. M. Al-Sadi, I. Ahmed, Expert Opin. Ther. Pat., 2017, 27, 1061.

    Article  CAS  PubMed  Google Scholar 

  10. M. B. Isah, M. A. Ibrahim, A. Mohammed, A. B. Aliyu, B. Masola, T. H. Coetzer, Parasitology, 2016, 143, 1219.

    Article  CAS  PubMed  Google Scholar 

  11. D. J. Newman, G. M. Cragg, J. Nat. Prod., 2012, 75, 311.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. M. Kvasnica, M. Urban, N. J. Dickinson, J. Sarek, Nat. Prod. Rep., 32, 1303.

  13. M. Zhou, R.-H. Zhang, M. Wang, G.-B. Xu, Sh.-G. Liao, Eur. J. Med. Chem., 2017, 131, 222.

    Article  CAS  PubMed  Google Scholar 

  14. R. Csuk, R. Sczepek, B. Siewert, C. Nitsche, Bioorg. Med. Chem., 2013, 21, 425.

    Article  CAS  PubMed  Google Scholar 

  15. A. Siddiq, V. Dembitsky, Anti-Cancer Agents Med. Chem., 2008, 8, 132.

    Article  CAS  Google Scholar 

  16. J. Pokorny, L. Borkova, M. Urban, Curr. Med. Chem., 2018, 25, 636.

    Article  CAS  PubMed  Google Scholar 

  17. K. Kacprzak, I. Skiera, M. Piasecka, Z. Paryzek, Chem. Rev., 2016, 116, 5689.

    Article  CAS  PubMed  Google Scholar 

  18. M. Urban, M. Kvasnica, N. J. Dickinson, J. Sarek, in Terpenoids and Squalene: Biosynthesis, Functions and Health Implications, Ed. A. R. Bates, Nova Sci. Publ., New York, 2015.

    Google Scholar 

  19. M. A. Lesniewska-Kowiel, I. Muszalska, Eur. J. Med. Chem., 2017, 129, 53.

    Article  CAS  PubMed  Google Scholar 

  20. D. Rodríguez-Hernandez, A. J. Demuner, L. C. A. Barbosa, L. Heller, R. Csuk, Eur. J. Med. Chem., 2015, 105, 57.

    Article  CAS  PubMed  Google Scholar 

  21. D. Bhunia, P. M. Pallavi, S. R. Bonam, S. A. Reddy, Y. Verma, M. S. K. Halmuthur, Arch. Pharm., 2015, 348, 689.

    Article  CAS  Google Scholar 

  22. T. A. D. Thi, N. T. K. Tuyet, C. P. The, H. T. Nguyen, C. B. Thi, T. D. Duy, M. D’hooghe, T. Van Nguyen, Bioorg. Med. Chem. Lett., 2014, 24, 5190.

    Article  CAS  Google Scholar 

  23. K. Cheng, J. Liu, X. Liu, H. Li, H. Sun, J. Xie, Carbohydr. Res., 2009, 344, 841.

    Article  CAS  PubMed  Google Scholar 

  24. J. Park, M. Koh, J. Y. Koo, S. Lee, S. B. Park, ACS Chem. Biol., 2015, 11, 44.

    Article  CAS  PubMed  Google Scholar 

  25. O. B. Kazakova, N. I. Medvedeva, I. P. Baikova, G. A. Tolstikov, T. V. Lopatina, M. S. Yunusov, L. Zaprutko, Russ. J. Bioorg. Chem., 2010, 36, 771.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. S. Boryczka, E. Bębenek, J. Wietrzyk, K. Kempińska, M. Jastrzębska, J. Kusz, M. Nowak, Molecules, 2013, 18, 4526.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. T. A. D. Thi, N. T. K. Tuyet, C. P. The, H. T. Nguyen, C. B. Thi, H. T. Phuong, L. V. Boi, T. V. Nguyen, M. D’hooghe, Tetrahedron Lett., 2015, 56, 218.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 3 Build., 1 Leninskie Gory, 119991, Moscow, Russian Federation

    E. Yu. Yamansarov, I. V. Saltykova, S. V. Kovalev, R. A. Petrov, D. O. Shkil’, E. I. Seleznev, E. K. Beloglazkina & A. G. Majouga

  2. National University of Science and Technology MISIS, 4 Leninskii prosp., 119049, Moscow, Russian Federation

    A. G. Majouga

  3. D. Mendeleev University of Chemical Technology of Russia, 1 Build., 9 Miusskaya pl., 125047, Moscow, Russian Federation

    A. G. Majouga

Authors
  1. E. Yu. Yamansarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Saltykova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Kovalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. A. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. O. Shkil’
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. I. Seleznev
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. E. K. Beloglazkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. A. G. Majouga
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. Yu. Yamansarov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0855–0861, April, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yamansarov, E.Y., Saltykova, I.V., Kovalev, S.V. et al. Synthesis and cytotoxicity of new alkyne derivatives of pentacyclic triterpenoids. Russ Chem Bull 68, 855–861 (2019). https://doi.org/10.1007/s11172-019-2496-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2496-1

Key words

Search

Navigation