Skip to main content
SpringerLink
Log in

Synthesis of Several Cytisine Derivatives and their Cytotoxicities against A431, A375, and HCT 116 Tumor Cell Lines

  • Published:
Chemistry of Natural Compounds Aims and scope

Cytotoxicities of the quinolizidine alkaloid (–)-cytisine and 19 of its derivatives with substituents in the 3-, 9-, and 11-positions were assessed against A431 (epidermal carcinoma), A375 (melanoma), and HCT 116 (colorectal carcinoma) tumor cell lines using the MTT assay (etoposide reference drug). Practically all synthesized compounds at a concentration of 30 μM possessed slight ability to inhibit metabolic activity of these cell lines except benzylcytisine 4, methylcytisines 18 and 19, which contained a phenylurea fragment in the 9- or 11-position of the 2-pyridone core, and 11-chloro adamantylthiocarboxamide 16. Thiocarboxamide 16 reduced A431 cell survival up to 56.06% under the experimental conditions; derivatives 4, 18, and 19, of HCT 116 cell line by 57.52, 58.84, and 56.34%, respectively.

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. D. J. Newman and G. M. Cragg, J. Nat. Prod., 79, 629 (2016).

    Article  CAS  Google Scholar 

  2. K. Mohan, R. Jeyachandran, and R. Deepa, Ann. Phytomed., 1, 46 (2012).

    CAS  Google Scholar 

  3. Z. Habli, G. Toumieh, M. Fatfat, O. N. Rahal, and H. Gali-Muhtasi, Molecules, 22, 250 (2017).

    Article  Google Scholar 

  4. I. P. Tsypysheva, P. R. Petrova, A. V. Koval′skaya, N. Lobov, M. A. Maksimova, L. F. Zainullina, V. I. Vinogradova, V. A. Vakhitov, Yu. V. Vakhitova, and F. Z. Galin, Chem. Nat. Compd., 54, 938 (2018).

    Article  CAS  Google Scholar 

  5. I. P. Tsypysheva, A. V. Koval′skaya, P. R. Petrova, A. N. Lobov, A. S. Erastov, Z. R. Zileeva, V. A. Vakhitov, and Yu. V. Vakhitova, Tetrahedron, 76 (7), 130902 (2020).

    Article  CAS  Google Scholar 

  6. H.-Q. Li, P.-C. Lv, T. Yan, and H.-L. Zhu, Anti-Cancer Agents Med. Chem., 9, 471 (2009).

    Article  CAS  Google Scholar 

  7. V. Kumar and S. S. Chimni, Anti-Cancer Agents Med. Chem., 15, 163 (2015).

    CAS  Google Scholar 

  8. C. C. Boido and F. Sparatore, Farmaco, 54, 438 (1999).

    Article  CAS  Google Scholar 

  9. I. P. Tsypysheva, A. V. Koval′skaya, N. S. Makara, A. N. Lobov, I. A. Petrenko, E. G. Galkin, T. A. Sapozhnikova, F. S. Zarudii, and M. S. Yunusov, Chem. Nat. Compd., 48, 629 (2012).

    CAS  Google Scholar 

  10. F. Moll and G. Luputiu, Arch. Pharm., 305, 771 (1972).

    CAS  Google Scholar 

  11. I. P. Tsypysheva, A. V. Koval′skaya, A. N. Lobov, M. Kh. Salimgareeva, U. Sh. Fatkullina, P. R. Petrova, S. F. Gabdrakhmanova, N. S. Makara, K. Yu. Suponitskii, Yu. V. Vakhitova, F. S. Zarudii, and M. S. Yunusov, Chem. Nat. Compd., 49, 707 (2013).

    CAS  Google Scholar 

  12. V. A. Fedorova, R. A. Kadyrova, A. V. Slita, A. A. Muryleva, P. R. Petrova, A. V. Kovalskaya, A. N. Lobov, D. O. Tsypyshev, S. S. Borisevich, I. P. Tsypysheva, Z. R. Zileeva, J. V. Vakhitova, and V. V. Zarubaev, Nat. Prod. Res., https://www.tandfonline.com/doi/full/10.1080/14786419.2019.1696791, 2019.

  13. K. Yu. Suponitskii, I. P. Tsypysheva, and A. V. Koval′skaya, J. Struct. Chem., 56, 188 (2015).

    CAS  Google Scholar 

  14. G. Luputiu and L. Gilau, Arch. Pharm., 302, 943 (1969).

    CAS  Google Scholar 

  15. I. V. Kulakov, Zh. M. Zhambekov, A. A. Ainabaev, S. D. Fazylov, and O. A. Nurkenov, Izv. Nats. Akad. Nauk Resp. Kaz., Ser. Khim., 4, 37 (2008).

    Google Scholar 

  16. Yu. V. Vakhitova, I. P. Tsypysheva, M. Kh. Salimgareeva, A. V. Kovalskaya, A. N. Lobov, U. Sh. Fatkullina, L. F. Zainullina, and M. S. Yunusov, Chem. Nat. Compd., 50, 498 (2014).

    CAS  Google Scholar 

  17. P. R. Petrova, A. V. Koval′skaya, A. N. Lobov, and I. P. Tsypysheva, Chem. Nat. Compd., 55, 1110 (2019).

    CAS  Google Scholar 

  18. P. R. Petrova, A. V. Koval′skaya, A. N. Lobov, and I. P. Tsypysheva, Chem. Nat. Compd., 55, 908 (2019).

    CAS  Google Scholar 

  19. I. P. Tsypysheva, A. V. Koval′skaya, I. U. Khalilova, Yu. Yu. Bakhtina, R. Yu. Khisamutdinova, S. F. Gabdrakhmanova, A. N. Lobov, F. S. Zarudii, and M. S. Yunusov, Chem. Nat. Compd., 50, 333 (2014).

    Article  CAS  Google Scholar 

  20. J. Buckingham, K. H. Baggaley, A. D. Roberts, and L. F. Szabo, Dictionary of Alkaloids, 2nd Ed., CRC Press, 2010, 2374 pp.

Download references

Acknowledgment

The work was sponsored by a State Task for UfIC, UFRC, RAS, Topic No. AAAA-A20-120012090026-9.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    P. R. Petrova, A. V. Koval′skaya & I. P. Tsypysheva

  2. Medicinal Chemistry Center, Tolyatti State University, 14 Belorusskaya St., Tolyatti, 445020, Russia

    A. S. Bunev

Authors
  1. P. R. Petrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Koval′skaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. P. Tsypysheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Bunev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. P. Tsypysheva.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2020, pp. 763–766.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Petrova, P.R., Koval′skaya, A.V., Tsypysheva, I.P. et al. Synthesis of Several Cytisine Derivatives and their Cytotoxicities against A431, A375, and HCT 116 Tumor Cell Lines. Chem Nat Compd 56, 892–895 (2020). https://doi.org/10.1007/s10600-020-03177-x

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-020-03177-x

Keywords

Search

Navigation