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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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).
J. Mastropaolo, R. B. Rosse, and S. I. Deutsch, Behav. Brain Res., 153, 419 (2004).
C. C. Boido, B. Tasso, V. Boido, and F. Sparatore, Farmaco, 58, 265 (2003).
X. Huang and H. Xu, Mini-Rev. Med. Chem., 20, 369 (2020).
V. M. Dembitsky and D. O. Levitsky, Nat. Prod. Commun., 1, 405 (2006).
R. L. Hudkins, D. L. DeHaven-Hudkins, and P. Doukas, Bioorg. Med. Chem. Lett., 7, 979 (1997).
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).
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).
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).
S. P. Bondarenko, E. V. Podobii, M. S. Frasinyuk, V. I. Vinogradova, and V. P. Khilya, Chem. Nat. Compd., 50, 420 (2014).
M. S. Frasinyuk, V. I. Vinogradova, S. P. Bondarenko, and V. P. Khilya, Chem. Nat. Compd., 43, 590 (2007).
S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Chem. Nat. Compd., 52, 615 (2016).
M. V. Mavrov and S. G. Zlotin, Russ. Chem. Bull., 58, 1921 (2009).
M. V. Mavrov and S. G. Zlotin, Chem. Heterocycl. Compd., 45, 677 (2009).
M. V. Mavrov and S. G. Zlotin, Russ. Chem. Bull., 56, 1637 (2007).
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).
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).
N. I. Simirskaya, N. V. Ignat’ev, M. Schulte, and S. G. Zlotin, Mendeleev Commun., 22, 317 (2012).
O. I. Artyushin, N. M. Vinogradova, E. V. Sharova, G. K. Genkina, and V. K. Brel, Heteroat. Chem., 27, 245 (2016).
V. K. Brel, Russ. J. Org. Chem., 52, 54 (2016).
S. D. Fazylov, A. M. Gazaliev, O. V. Bakbardina, and B. I. Tuleuov, Russ. J. Gen. Chem., 70, 820 (2000).
S. P. Bondarenko, O. G. Makarenko, V. I. Vinogradova, and M. S. Frasinyuk, Chem. Nat. Compd., 56, 1040 (2020).
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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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DOI: https://doi.org/10.1007/s10600-021-03268-3