Synthesis of New Conjugates of Coumarins with Anabasine and Cytisine

The reactions of cytisine with glycidyl ethers of 3-arylcoumarins were studied. A series of cytisine–coumarin conjugates were synthesized via regiospecific opening of the oxirane ring by cytisine. Methods for conjugating anabasine and cytisine with 3-arylcoumarins through a but-2-ynyl linker via reactions of propargyl ethers of 7-hydroxy- and 6-hydroxy-3-arylcoumarins with the alkaloids were proposed.

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References

  1. 1.

    S. T. Lee, K. Wildeboer, K. E. Panter, W. R. Kem, D. R. Gardner, R. J. Molyneux, C. W. T. Chang, F. Soti, and J. A. Pfister, Neurotoxicol. Teratol., 28, 220 (2006).

    CAS  Article  Google Scholar 

  2. 2.

    J. Mastropaolo, R. B. Rosse, and S. I. Deutsch, Behav. Brain Res., 153, 419 (2004).

    CAS  Article  Google Scholar 

  3. 3.

    C. C. Boido, B. Tasso, V. Boido, and F. Sparatore, Farmaco, 58, 265 (2003).

    CAS  Article  Google Scholar 

  4. 4.

    X. Huang and H. Xu, Mini-Rev. Med. Chem., 20, 369 (2020).

    CAS  Article  Google Scholar 

  5. 5.

    V. M. Dembitsky and D. O. Levitsky, Nat. Prod. Commun., 1, 405 (2006).

    CAS  Google Scholar 

  6. 6.

    R. L. Hudkins, D. L. DeHaven-Hudkins, and P. Doukas, Bioorg. Med. Chem. Lett., 7, 979 (1997).

    CAS  Article  Google Scholar 

  7. 7.

    K. B. Sanders, A. J. Thomas, M. R. Pavia, R. E. Davis, L. L. Coughenour, S. L. Myers, S. Fisher, and W. H. Moos, Bioorg. Med. Chem. Lett., 2, 803 (1992).

    CAS  Article  Google Scholar 

  8. 8.

    A. Z. Kabdraisova, M. F. Faskhutdinov, V. K. Yu, K. D. Praliev, E. E. Fomicheva, S. N. Shin, and K. D. Berlin, Chem. Nat. Compd., 43, 437 (2007).

    CAS  Article  Google Scholar 

  9. 9.

    M. S. Frasinyuk, W. Zhang, P. Wyrebek, T. Yu, X. Xu, V. M. Sviripa, S. P. Bondarenko, Y. Xie, H. Ngo, A. Morris, J. L. Mohler, M. Fiandalo, D. S. Watt, and C. Liu, Org. Biomol. Chem., 15, 7623 (2017).

    CAS  Article  Google Scholar 

  10. 10.

    S. P. Bondarenko, E. V. Podobii, M. S. Frasinyuk, V. I. Vinogradova, and V. P. Khilya, Chem. Nat. Compd., 50, 420 (2014).

    CAS  Article  Google Scholar 

  11. 11.

    M. S. Frasinyuk, V. I. Vinogradova, S. P. Bondarenko, and V. P. Khilya, Chem. Nat. Compd., 43, 590 (2007).

    CAS  Article  Google Scholar 

  12. 12.

    S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Chem. Nat. Compd., 52, 615 (2016).

    CAS  Article  Google Scholar 

  13. 13.

    M. V. Mavrov and S. G. Zlotin, Russ. Chem. Bull., 58, 1921 (2009).

    CAS  Article  Google Scholar 

  14. 14.

    M. V. Mavrov and S. G. Zlotin, Chem. Heterocycl. Compd., 45, 677 (2009).

    CAS  Article  Google Scholar 

  15. 15.

    M. V. Mavrov and S. G. Zlotin, Russ. Chem. Bull., 56, 1637 (2007).

    CAS  Article  Google Scholar 

  16. 16.

    V. T. Bauman, E. E. Shul’ts, V. V. Kononchuk, I. Y. Bagryanskaya, M. M. Shakirov, and G. A. Tolstikov, Russ. J. Org. Chem., 49, 1502 (2013).

    CAS  Article  Google Scholar 

  17. 17.

    S. A. Osadchii, E. E. Shults, E. V. Polukhina, M. M. Shakirov, S. F. Vasilevskii, A. A. Stepanov, and G. A. Tolstikov, Russ. Chem. Bull., 56, 1261 (2007).

    CAS  Article  Google Scholar 

  18. 18.

    N. I. Simirskaya, N. V. Ignat’ev, M. Schulte, and S. G. Zlotin, Mendeleev Commun., 22, 317 (2012).

    CAS  Article  Google Scholar 

  19. 19.

    O. I. Artyushin, N. M. Vinogradova, E. V. Sharova, G. K. Genkina, and V. K. Brel, Heteroat. Chem., 27, 245 (2016).

    CAS  Article  Google Scholar 

  20. 20.

    V. K. Brel, Russ. J. Org. Chem., 52, 54 (2016).

    CAS  Article  Google Scholar 

  21. 21.

    S. D. Fazylov, A. M. Gazaliev, O. V. Bakbardina, and B. I. Tuleuov, Russ. J. Gen. Chem., 70, 820 (2000).

    CAS  Google Scholar 

  22. 22.

    S. P. Bondarenko, O. G. Makarenko, V. I. Vinogradova, and M. S. Frasinyuk, Chem. Nat. Compd., 56, 1040 (2020).

    Article  Google Scholar 

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Correspondence to S. P. Bondarenko.

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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2021, pp. 12–15.

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Bondarenko, S.P., Mrug, G.P., Vinogradova, V.I. et al. Synthesis of New Conjugates of Coumarins with Anabasine and Cytisine. Chem Nat Compd 57, 9–13 (2021). https://doi.org/10.1007/s10600-021-03268-3

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Keywords

  • cytisine
  • anabasine
  • 3-arylcoumarin
  • glycidyl ether
  • propargyl ether