Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 8, pp 1586–1590 | Cite as

Synthesis of New Fused Thiopyridines and Their Reaction with Acetylacetone in the Presence of Mercury(II) Acetate

  • N. G. HobosyanEmail author
  • K. V. Balyan
  • H. S. Nersisyan
  • H. B. Sargsyan
  • V. M. Kobalyan
  • Sh. Sh. Dashyan
  • I. M. Nazaryan
  • E. G. Paronikyan
Article
  • 1 Downloads

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.

Keywords

acetylacetone mercury(II) acetate mercuration demercuration tautomers thiopyridines 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

References

  1. 1.
    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 CrossRefGoogle Scholar
  2. 2.
    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 CrossRefGoogle Scholar
  3. 3.
    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 CrossRefGoogle Scholar
  4. 4.
    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 Google Scholar
  5. 5.
    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 CrossRefGoogle Scholar
  6. 6.
    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 CrossRefGoogle Scholar
  7. 7.
    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 CrossRefGoogle Scholar
  8. 8.
    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 CrossRefGoogle Scholar
  9. 9.
    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.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • N. G. Hobosyan
    • 1
    Email author
  • K. V. Balyan
    • 1
  • H. S. Nersisyan
    • 1
  • H. B. Sargsyan
    • 1
  • V. M. Kobalyan
    • 1
  • Sh. Sh. Dashyan
    • 1
  • I. M. Nazaryan
    • 1
  • E. G. Paronikyan
    • 1
  1. 1.Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Sciences of the Republic of ArmeniaErevanArmenia

Personalised recommendations