Skip to main content
Log in

Synthesis of 19-(2,6-Dimethylpyrid-4-yl)-20,29,30-trinorlupanes

  • Published:
Chemistry of Natural Compounds Aims and scope

19-(2,6-Dimethylpyrid-4-yl)-20,29,30-trinorlupanes in addition to triterpenoid derivatives condensed in ring A of the pyran-4-one ring were synthesized for the first time from betulin, betulin diacetate, and methyl esters of 3-acetylbetulinic and betulonic acids.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R.-Y. Kuo, K. Qian, S. L. Morris-Natschke, and K.-H. Lee, Nat. Prod. Rep., 26, 1321 (2009).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  2. M. K. Shanmugam, A. H. Nguyen, A. P. Kumar, B. K. H. Tan, and G. Sethi, Cancer Lett., 320, 158 (2012).

    Article  CAS  PubMed  Google Scholar 

  3. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Russ. J. Bioorg. Chem., 32, 37 (2006).

    Article  CAS  Google Scholar 

  4. I. V. Sorokina, I. Ya. Mainagashev, N. A. Zhukova, D. V. Korchagina, T. G. Tolstikova, V. P. Nikolin, N. A. Popova, M. A. Pokrovskii, A. G. Pokrovskii, and N. F. Salakhutdinov, Russ. J. Bioorg. Chem., 39, 194 (2013).

    Article  CAS  Google Scholar 

  5. R. Mukherjee, M. Jaggi, M. J. A. Siddiqui, S. K. Srivastava, P. Rajendran, A. Vardhan, and A. C. Burman, Bioorg. Med. Chem. Lett., 14, 4087 (2004).

    Article  CAS  PubMed  Google Scholar 

  6. I.-H. Chen, Y.-C. Du, M.-C. Lu, A.-S. Lin, P.-W. Hsieh, C.-C. Wu, S.-L. Chen, H.-F. Yen, F.-R. Chang, and Y.-C. Wu, J. Nat. Prod., 71, 1352 (2008).

    Article  CAS  PubMed  Google Scholar 

  7. L. C. Baratto, M. V. Porsani, I. C. Pimentel, A. B. Pereira Netto, R. Paschke, and B. H. Oliveira, Eur. J. Med. Chem., 68, 121 (2013).

    Article  CAS  PubMed  Google Scholar 

  8. O. B. Kazakova, G. V. Giniyatullina, E. Yu. Yamansarov, and G. A. Tolstikov, Bioorg. Med. Chem. Lett., 20, 4088 (2010).

    Article  CAS  PubMed  Google Scholar 

  9. J. Holy, O. Kolomitsyna, D. Krasutsky, P. J. Oliveira, E. Perkins, and P. A. Krasutsky, Bioorg. Med. Chem., 18, 6080 (2010).

    Article  CAS  PubMed  Google Scholar 

  10. T. C. Bernardo, T. Cunha-Oliveira, T. L. Serafim, J. Holy, D. Krasutsky, O. Kolomitsyna, P. Krasutsky, A. M. Moreno, and P. J. Oliveira, Bioorg. Med. Chem., 21, 7239 (2013).

    Article  CAS  PubMed  Google Scholar 

  11. K. Qian, D. Yu, C.-H. Chen, L. Huang, S. L. Morris-Natschke, T. J. Nitz, K. Salzwedel, M. Reddick, G. P. Allaway, and K.-H. Lee, J. Med. Chem., 52, 3248 (2009).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  12. A. N. Antimonova, N. I. Petrenko, M. M. Shakirov, T. V. Rybalova, T. S. Frolova, E. E. Shults, T. P. Kukina, O. I. Sinitsyna, and G. A. Tolstikov, Chem. Nat. Compd., 49, 657 (2013).

    Article  CAS  Google Scholar 

  13. F. A. Selimov, U. M. Dzhemilev, and O. A. Ptashko, Metal-Complex Catalysis in the Synthesis of Pyrilium Bases [in Russian], Moscow, 2003, 303 pp.

  14. J. A. R. Salvador, R. M. A. Pinto, R. C. Santos, C. Le Roux, A. M. Bejad, and J. A. Paixao, Org. Biomol. Chem., 7, 508 (2009).

    Article  CAS  PubMed  Google Scholar 

  15. W. Dehaen, A. A. Mashentseva, and T. S. Seitembetov, Molecules, 16, 2443 (2011).

    Article  CAS  PubMed  Google Scholar 

  16. S. Siddiqui, F. Hafeez, S. Begum, and B. S. Siddiqui, J. Nat. Prod., 51, 229 (1988).

    Article  CAS  Google Scholar 

  17. V. Peesapati and S. Bathini, Indian Chem. Soc., 86, 544 (2009).

    CAS  Google Scholar 

  18. I. A. Tolmacheva, L. N. Shelepen’kina, A. S. Shashkov, V. V. Grishko, V. A. Glushkov, and A. G. Tolstikov, Chem. Nat. Compd., 43, 153 (2007).

    Article  CAS  Google Scholar 

  19. T.-S. Li, J.-X. Wang, and X.-J. Zheng, J. Chem. Soc. Perkin Trans. 1, 3957 (1998).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. E. Shul’ts.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2014, pp. 268–273.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Antimonova, A.N., Petrenko, N.I., Shakirov, M.M. et al. Synthesis of 19-(2,6-Dimethylpyrid-4-yl)-20,29,30-trinorlupanes. Chem Nat Compd 50, 305–310 (2014). https://doi.org/10.1007/s10600-014-0938-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-014-0938-4

Keywords

Navigation