Skip to main content
SpringerLink
Log in

Synthesis of 2-nicotinylidene triterpenoids: structure, complexation with palladium, and in vitro cytotoxic activity

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

Abstract

A series of ligands were synthesized by crotonic condensation of nicotinaldehyde at the C(2) position of various tritepenoids and were then involved in the complex formation with PdII to prepare finally five new compounds. The cytotoxic activity evaluation in the A549 cell line (adenocarcinomic human alveolar basal epithelial cells) and the HeLa cell line (human cervical carcinoma cells) using the MTT assay demonstrated that methyl 3-oxo-2-(pyridin-3-ylmethylidene)-lup-20(29)-en-28-oate exhibits moderate cytotoxicity (IC50 is 17.34–20.02 µmol L−1).

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. T. J. Carneiro, A. S. Martins, M. P. M. Marques, A. M. Gil, Front. Oncol., 2020, 10, 590970; DOI: https://doi.org/10.3389/fonc.2020.590970.

    Article  PubMed  PubMed Central  Google Scholar 

  2. T. E. Kokina, V. Y. Komarov, L. A. Glinskaya, L. A. Sheludyakova, Y. A. Eremina, A. V. Tkachev, S. N. Bizyaev, L. S. Klyushova, Russ. J. Struct. Chem., 2020, 61, 44; DOI: https://doi.org/10.1134/S0022476620010059.

    Article  CAS  Google Scholar 

  3. Th. Scattolin, V. A. Voloshkin, F. Visentin, S. P. Nolan, Cell Rep. Phys. Sci., 2021, 2, 100446; DOI: https://doi.org/10.1016/j.xcrp.2021.100446.

    Article  CAS  Google Scholar 

  4. O. A. Zalevskaya, Y. A. Gur’eva, A. V. Kutchin, Inorg. Chim. Acta., 2021, 527, 120593; DOI: https://doi.org/10.1016/j.ica.2021.120593.

    Article  CAS  Google Scholar 

  5. V. P. Boyarskii, A. S. Mikherdov, S. V. Baikov, P. Y. Savko, R. V. Suezov, R. E. Trifonov, Pharm. Chem. J., 2021, 55, 130; DOI: https://doi.org/10.1007/s11094-021-02393-1.

    Article  CAS  Google Scholar 

  6. A. A. Batyrenko, O. V. Mikolaichuk, G. K. Ovsepyan, A. V. Protas, I. V. Kornyakov, E. V. Lider, Yu. A. Eremina, T. S. Khlebnikova, F. A. Lakhvich, R. E. Trifonov, Russ. J. Gen. Chem., 2021, 91, 666; DOI: https://doi.org/10.1134/S1070363221040149.

    Article  CAS  Google Scholar 

  7. M. S. Denisov, O. N. Gagarskikh, Russ. J. Gen. Chem., 2021, 91, 1354; DOI: https://doi.org/10.1134/S1070363221070136.

    Article  CAS  Google Scholar 

  8. T. V. Baulinaa, I. Yu. Kudryavtseva, O. V. Bykhovskayaa, M. P. Pasechnika, L. V. Anikinaa, A. V. Vologzhaninaa, V. A. Kochmarika, V. K. Brel, Russ. J. Gen. Chem., 2021, 91, 2052; DOI: https://doi.org/10.1134/S1070363221100194.

    Article  Google Scholar 

  9. N. Van-Ha, Ph. T. T. Hien, D. T. Data, Do T. Thao, Mendeleev Commun., 2022, 32, 594; DOI: https://doi.org/10.1016/j.mencom.2022.09.008.

    Article  CAS  Google Scholar 

  10. Ya. A. Gur’eva, O. A. Zalevskaya, N. S. Nikolaeva, Yu. R. Aleksandrova, E. Yu. Yandulova, M. E. Neganova, A. V. Kutchin Russ. Chem. Bull., 2023, 72, 793; DOI: 1066-5285/23/7203-0793.

    Article  Google Scholar 

  11. O. Zalevskaya, Ya. Gur’eva, A. Kutchin, K. A. Hansford, Antibiotics, 2020, 9, 277; DOI: https://doi.org/10.3390/antibiotics9050277.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. M. A. Nazarov, I. A. Tolmacheva, D. V. Eroshenko, O. A. Maiorova, M. V. Dmitriev, V. V. Grishko, Chem. Heterocycl. Compd., 2020, 56, 1321; DOI: https://doi.org/10.1007/s10593-020-02817-y.

    Article  Google Scholar 

  13. M. N. Gorbunova, G. F. Krainova, A. O. Voronina, Khimiya rastitel’nogo syr’ya [Chemistry of Plant Raw Materials], 2020, 1, 49; DOI: https://doi.org/10.14258/jcprm.2020015609 (in Russian).

    Google Scholar 

  14. G. V. Giniyatullina, A. V. Petrova, A. G. Mustafin, Z. R. Zileeva, U. Sh. Kuzmina, Yu. V. Vakhitova, O. B. Kazakova, ChemistrySelect, 2021, 6, 13253; DOI: https://doi.org/10.1002/slct.202101687.

    Article  CAS  Google Scholar 

  15. M. S. Denisov, V. A. Glushkov, Russ. Chem. Bull., 2020, 69, 2013; DOI: https://doi.org/10.1007/s11172-020-2993-2.

    Article  CAS  Google Scholar 

  16. M. S. Denisov, M. V. Dmitriev, O. N. Gagarskikh, V. A. Glushkov, Chem. Nat. Compd., 2022, 58, 307; DOI: https://doi.org/10.1007/s10600-022-03665-2.

    Article  CAS  Google Scholar 

  17. M. S. Denisov, Russ. J. Gen. Chem., 2023, 91, 37; DOI: https://doi.org/10.1134/S1070363223010061.

    Article  Google Scholar 

  18. M. O. Tserfas, Yu. V. Kuznetsov, V. V. Knyazev, I. S. Levina, I. V. Zavarzin, Russ. Chem. Bull., 2022, 71, 1806; DOI: https://doi.org/10.1007/s11172-022-3593-0.

    Article  CAS  Google Scholar 

  19. O. A. Koroleva, Yu. V. Dutikova, A. V. Trubnikov, F. A. Zenov, E. V. Manasova, A. A. Shtil, A. V. Kurkin, Russ. Chem. Bull., 2022, 71, 2310; DOI: https://doi.org/10.1007/s11172-022-3659-z.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. V. V. Grishko, A. V. Nazarov, I. A. Tolmacheva, E. V. Tarasova, I. B. Ivshina, Chem. Nat. Compd., 2014, 50, 857; DOI: https://doi.org/10.1007/s10600-014-1100-z.

    Article  CAS  Google Scholar 

  21. Zh. Liu, J. J. Swidorski, B. Nowicka-Sans, B. Terry, T. Protack, Z. Lin, H. Samanta, Sh. Zhang, Zh. Li, D. D. Parker, S. Rahematpura, S. Jenkins, B. R. Beno, M. Krystal, N. A. Meanwell, I. B. Dicker, A. Regueiro-Ren, Bioorg. Med. Chem., 2016, 24, 1757; DOI: https://doi.org/10.1016/j.bmc.2016.03.001.

    Article  CAS  PubMed  Google Scholar 

  22. Z. I. Galimova, M. S. Babaev, A. N. Lobov, O. B. Kazakova, Russ. J. Org. Chem., 2021, 57, 1012; DOI: https://doi.org/10.1134/S1070428021060208.

    Article  CAS  Google Scholar 

  23. An Shen, Ch. Ni, Yu-C. Cao, H. Zhou, G.-H. Song, X.-F. Ye, Tetrahedron Lett., 2014, 55, 3278; DOI: https://doi.org/10.1016/j.tetlet.2014.04.044.

    Article  CAS  Google Scholar 

  24. N. L. Bazyakina, V. M. Makarov, M. V. Moskalev, E. V. Baranov, A. S. Bogomyakov, V. I. Ovcharenko, I. L. Fedushkin, Mendeleev Commun., 2022, 32, 759; DOI: https://doi.org/10.1016/j.mencom.2022.11.017.

    Article  CAS  Google Scholar 

  25. M. D. Hall, K. A. Telma, Ki-E. Chang, T. D. Lee, J. P. Madigan, J. R. Lloyd, I. S. Goldlust, J. D. Hoeschele, M. M. Gottesman, Cancer Res., 2014, 74, 3913; DOI: https://doi.org/10.1158/0008-5472.CAN-14-0247.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. M. Neganova, A. Semakov, Yu. Aleksandrova, E. Yaduliva, S. Puhov, L. Anikina, S. Klochkov, Biomedicines, 2021, 9, 547; DOI: https://doi.org/10.3390/biomedicines9050547.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. M. S. Denisov, Perm Federal Research Center Journal, 2021, 4, 6; DOI: https://doi.org/10.7242/2658-705X/2021.4.1.

    Google Scholar 

  28. M. R. Ibatullina, E. P. Zhil’tsova, N. V. Kulik, A. P. Lyubina, S. K. Amerhanova, A. D. Voloshina, S. S. Lukashenko, N. Kh. Safina, L. Ya. Zakharova, Russ. Chem. Bull., 2022, 71, 314; DOI: https://doi.org/10.1007/s11172-022-3413-6.

    Article  CAS  Google Scholar 

  29. V. G. Vlasenko, A. S. Burlov, M. S. Milutka, Yu. V. Koshchienko, A. I. Uraev, V. A. Lazarenko, N. I. Makarova, A. V. Metelitsa, A. A. Zubenko, D. A. Garnovskii, Russ. J. Coord. Chem., 2023, 49, 148; DOI: https://doi.org/10.1134/S1070328422700221.

    Article  CAS  Google Scholar 

  30. V. Korovin, A. V. Tkachev, Russ. Chem. Bull., 2001, 50, 304; DOI: https://doi.org/10.1023/A:1009598805986.

    Article  CAS  Google Scholar 

  31. L.-W. Qian, J. Zhang, J.-H. Liu, B.-Ya. Yu, Tetrahedron Lett., 2009, 50, 2193; DOI: https://doi.org/10.1016/j.tetlet.2009.02.137.

    Article  CAS  Google Scholar 

  32. H. Yamashita, M. Matsuzaki, Yu. Kurokawa, T. Nakane, M. Goto, K.-H. Lee, T. Shibata, H. Bandoa, K. Wad, Phytochem. Lett., 2019, 31, 140; DOI: https://doi.org/10.1016/j.phytol.2019.03.015.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. O. Callies, L. M. Bedoya, M. Beltran, A. Muñ, P. O. Caldero, A. A. Osorio, I. A. Jimenez, J. Alcamí, I. L. Bazzocchi, J. Nat. Prod., 2015, 78, 1045; DOI: https://doi.org/10.1021/np501025r.

    Article  CAS  PubMed  Google Scholar 

  34. C. C. Laev, N. F. Salakhudinov, in Preparativnaya khimiya terpenoidov, Ch. 3. Triterpenoidy: lupeol, betulin, betulinovaya kislota, oleanolovaya kislota, moronovaya kislota, ursulovaya kislota, glitsiretovaya kislota, bosvellievaya kislota [Preparative Chemistry of Terpenoids. Part 3. Triterpenoids: Lupeol, Betulin, Betulinic Acid, Oleanolic Acid, Moronic Acid, Ursolic Acid, Glycyrrhetinic Acid, Boswellic Acid], Akademizdat, Novosibirsk, 2016, p. 99 (in Russian).

    Google Scholar 

  35. N. A. Dangroo, J. Singh, S. K. Ratha, N. Gupta, A. Qayum, Sh. Singh, P. L. Sangwan, Steroids, 2017, 123, 1; DOI: https://doi.org/10.1016/j.steroids.2017.04.002.

    Article  CAS  PubMed  Google Scholar 

  36. M. V. Kaverin, P. A. Morozova, L. V. Snegur, Russ. Chem. Bull., 2022, 71, 2236; DOI: https://doi.org/10.1007/s11172-022-3651-7.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. CrysAlisPro, Rigaku Oxford Diffraction, 2022, Version 1.171.42.74a.

  38. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr., 2009, 42, 339; DOI: https://doi.org/10.1107/S0021889808042726.

    Article  CAS  Google Scholar 

  39. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3. DOI: https://doi.org/10.1107/S2053273314026370.

    Article  Google Scholar 

  40. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 2015, C71, 3; DOI: https://doi.org/10.1107/S2053229614024218.

    Google Scholar 

  41. B. M. F. Gonçalves, J. A. R. Salvador, S. Marín, M. Cascante, Eur. J. Med. Chem., 2016. 114. 101; DOI: https://doi.org/10.1016/j.ejmech.2016.02.057.

    Article  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences, 3 ul. Akademika Koroleva, 614013, Perm, Russian Federation

    M. S. Denisov & D. V. Eroshenko

Authors
  1. M. S. Denisov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Eroshenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. S. Denisov.

Ethics declarations

The authors declare no competing interests.

Additional information

The study was performed within the framework of the state assignment (state registration number 122012400109-8). The work was carried out using the equipment of the Core Facilities Center “Research of Materials and Matter” at the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences (PFRC UB RAS).

We are grateful to O. A. Maiorova (PFRC UB RAS) for measuring NMR spectra, I. A. Borisova (PFRC UB RAS) for recording IR spectra, M. V. Dmitriev (Perm State University) for performing the X-ray diffraction study, and Yu. A. Beloglazova (PFRC UB RAS) for performing the MTT assay.

No human or animal subjects were used in this research.

Based on the materials of the XII All-Russian Scientific Conference “Chemistry and Technology of Plant Substances” with international participation and the School for Young Scientists (November 29–December 2, 2022, Kirov, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2206–2214, September, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Denisov, M.S., Eroshenko, D.V. Synthesis of 2-nicotinylidene triterpenoids: structure, complexation with palladium, and in vitro cytotoxic activity. Russ Chem Bull 72, 2206–2214 (2023). https://doi.org/10.1007/s11172-023-4017-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4017-5

Key words

Search

Navigation