Abstract
The method of synthesis of fused thiopyridines via S-alkylation of the corresponding pyridine thiones with propargyl bromide has been elaborated. Fused enol tautomers have been obtained via the reaction of the prepared thiopropargyl pyridine compounds with acetylacetone in the presence of mercury(II) acetate followed by the reduction of intermediate organomercury compounds with alkali solution of sodium borohydride. Neurotropic activity of the synthesized compounds has been studied, and compounds with pronounced anticonvulsant activity have been identified.
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Buchanan, J.G., Craven, D.A., Wightman, R.H., and Harnden, M.R., J. Chem. Soc. Perkin Trans 1, 1991, vol. 1, p. 195. doi https://doi.org/10.1039/P19910000195
Chakrabort, A.K., Gopalakrishnan, B., Sobia, M.E., and Malde, A., Bioorg. Med. Chem. Lett., 2003, vol. 13, no. 8, p. 1403. doi https://doi.org/10.1016/S0960-894X(03)00172-0
Taltavull, J., Cracia, J., Gavalda, A., Anders, H., Cordoba, M., Miralpeix, M., Viletla, D., Beleta, J., Ryder, H., and Pages, L., J. Med. Chem., 2010, vol. 53, no. 19, p. 6912. doi https://doi.org/10.1021/jm100524j
Paronikyan, E.G., Mirzoyan, G.V, Noravyan, A.S., Hovakimyan, D.A., and Ter-Zakharyan, J.Z., Russ. Pharm. Chem. J., 1993, vol. 27, no. 11, p. 759. doi https://doi.org/10.1007/BF00780403
Badanyan, S.O., Chobanyan, Z.A., Tirakyan, M.R., and Danielyan, A.O., Chem. Heterocyclic Compd., 1998, vol. 34, no. 7, p. 781. doi https://doi.org/10.1007/BF02251682
Hobosyan, N.G., Balyan, K.V., Nersisyan, H.S., Sargsyan, H.B, and Chobanyan, Zh.A., Russ. J. Gen. Chem., 2016, vol. 86, no. 5, p. 1011. doi https://doi.org/10.1134/S1070363216050042
Balyan, K.V., Gendzhoyan, L.M., Akopyan, B.B., Hobosyan, N.G., and Chobanyan, Zh.A., Russ. J. Gen. Chem., 2014, vol. 84, no. 11, p. 2098. doi https://doi.org/10.1134/S1070363214110097
Hobosyan, N.G., Balyan, K.V., Petrosyan, A.L., Sargsyan, H.B., Chobanyan, Zh.A., and Nersisyan, H.S., Russ. J. Org Chem., 2018, vol. 54, no. 8, p. 1268. doi https://doi.org/10.1134/S1070428018080262
Vogel, H.G. and Vogel, W.H., Psychotropic and Neurotropic Activity, in Drug Discovery and Evaluation: Pharmacological Assays, Vogel, H.E., Ed., Berlin: Springer, 2008, p. 569.
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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 8, pp. 1195–1200.
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Hobosyan, N.G., Balyan, K.V., Nersisyan, H.S. et al. Synthesis of New Fused Thiopyridines and Their Reaction with Acetylacetone in the Presence of Mercury(II) Acetate. Russ J Gen Chem 89, 1586–1590 (2019). https://doi.org/10.1134/S1070363219080073
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DOI: https://doi.org/10.1134/S1070363219080073