Russian Journal of Organic Chemistry

, Volume 53, Issue 5, pp 753–763 | Cite as

Synthesis and biological activity of oxindolylidene derivatives of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7-ones and imidazo[4,5-e]thiazolo[2,3-с]-1,2,4-triazin-8-ones

  • A. N. Izmest’ev
  • G. A. Gazieva
  • A. S. Kulikov
  • L. V. Anikina
  • N. G. Kolotyrkina
  • A. N. Kravchenko
Article
  • 48 Downloads

Abstract

Reactions of 1,3-dialkyl-2-thioxo-1,2,3,3a,9,9a-hexahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7(6H)-ones with isatin and its derivatives under base catalysis conditions lead to the corresponding 1,3-dialkyl-6(7)-(2-oxoindolin-3-ylidene)derivatives of 2-thioxo-1,2,3,3a,9,9a-hexahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7(6H)-one or 2-thioxo-1,2,3,3a,4,9a-hexahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazin-8(7H)-one resulting from the aldol-crotonic condensation and skeletal amidine rearrangement of the thiazolotriazine fragment, depending on the amount of added alkali.

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References

  1. 1.
    Trepanier, D.L. and Krieger, P.E., US Patent no. 3641019, 1968; Chem. Abstr. 1972, vol. 76, p. 127024.Google Scholar
  2. 2.
    Abdel-Rahman, R.M., Seada, M., Fawzy, M., and El-Baz, I., Pharmazie, 1994, vol. 49, p. 729.Google Scholar
  3. 3.
    Volynets, G.P., Bdzhola, V.G., and Yarmoluk, S.M., FEBS J., 2011, vol. 278, p. 340. doi 10.1111/j.1742-4658.2010.07957.xGoogle Scholar
  4. 4.
    Niigata, K., Okada, M., and Yoneda, T., EU Patent no. 0237138, 1987; Chem. Abstr., 1988, vol. 108, p. 150462q.Google Scholar
  5. 5.
    Szewczuk, L.M., Saldanha, S.A., Ganguly, S., Bowers, E.M., Javoroncov, M., Karanam, B., Culhane, J.C., Holbert, M.A., Klein, D.C., Abagyan, R., and Cole, P.A., J. Med. Chem., 2007, vol. 50, p. 5330. doi 10.1021/jm0706463CrossRefGoogle Scholar
  6. 6.
    Avdieiev, S., Gera, L., Havrylyuk, D., Hodges, R.S., Lesyk, R., Ribrag, V., Vassetzky, Ye., and Kavsan, V., Bioorg. Med. Chem., 2014, vol. 22, p. 3815. doi 10.1016/j.bmc.2014.06.046CrossRefGoogle Scholar
  7. 7.
    Lesyk, R. and Zimenkovsky, B., Curr. Org. Chem., 2004, vol. 8, p. 1547. doi 10.2174/1385272043369773CrossRefGoogle Scholar
  8. 8.
    Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Zaprutko, L., Gzella, A., and Lesyk, R., Eur. J. Med. Chem., 2009, vol. 44, p. 1396. doi 10.1016/j.ejmech.2008.09.032CrossRefGoogle Scholar
  9. 9.
    Gazieva, G.A., Shishkova, E.A., Kulikova, L.B., Kolotyrkina, N.G., Sigay, N.V., and Kravchenko, A.N., J. Heterocycl. Chem., 2014, vol. 51, p. 921. doi 10.1002/jhet.2008CrossRefGoogle Scholar
  10. 10.
    Gazieva, G.A., Izmest'ev, A.N., Nelyubina, Yu.V., Kolotyrkina, N.G., Zanin, I.E., and Kravchenko, A.N., RSC Adv., 2015, vol. 5, p. 43990. doi 10.1039/C5RA07669BCrossRefGoogle Scholar
  11. 11.
    Hosseinzadeh, N., Hasani, M., Foroumadi, A., Nadri, H., Emami, S., Samadi, N., Faramarzi, M.A., Saniee, P., Siavoshi, F., Abadian, N., Mahmoudjanlou, Y., Sakhteman, A., Moradi, A., and Shafiee, A., Med. Chem. Res., 2013, vol. 22, p. 2293. doi 10.1007/s00044-012-0224-6CrossRefGoogle Scholar
  12. 12.
    Gazieva, G.A., Poluboyarov, P.A., Nelyubina, Yu.V., Struchkova, M.I., and Kravchenko, A.N., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1382.CrossRefGoogle Scholar
  13. 13.
    Radul, O.M., Zhungietu, G.I., Rekhter, M.A., and Bukhanyuk, S.M., Chem. Heterocycl. Compd., 1983, vol. 19, p. 286. doi 10.1007/BF00513261CrossRefGoogle Scholar
  14. 14.
    Bouhfid, R., Joly, N., El Essassi, M., Lequart, V., Massoui, M., and Martin, P., Synth. Commun., 2011, vol. 41, p. 2096. doi 10.1080/00397911.2010.497595CrossRefGoogle Scholar
  15. 15.
    Zhungietu, G.I. and Rekhter, M.A., Izatin i ego proizvodnye (Isatin and Its Derivatives), Kishinev Shtiintsa, 1977.Google Scholar
  16. 16.
    Mosmann, T., J. Immunol. Methods, 1983, vol. 65, p. 55. doi 10.1016/0022-1759(83)90303-4CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • A. N. Izmest’ev
    • 1
  • G. A. Gazieva
    • 1
  • A. S. Kulikov
    • 1
  • L. V. Anikina
    • 2
  • N. G. Kolotyrkina
    • 1
  • A. N. Kravchenko
    • 1
  1. 1.Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia
  2. 2.Institute of Physiologically Active SubstancesRussian Academy of SciencesChernogolovka, Moscow oblastRussia

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