Skip to main content
Log in

Modification of biologically active amides and amines with fluorine-containing heterocycles 12.* Endo- and exocyclic modifications of the drug riluzole with trifluoromethyl-containing heterocycles

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New derivatives of the drug riluzole, 6-(trifluoromethoxy)benzothiazol-2-ylamine, modified at the endo- and exocyclic nitrogen atoms with trifluoromethyl-containing heterocycles were synthesized via transformations of methyltrifluoropyruvate and hexafluoroacetone N-6-(trifluoromethoxy)benzothiazol-2-ylimines by meams of cycloaddition and cyclocondensation reactions, respectively. The influence of the resulting compounds on neuronal NMDA receptors, as well as on the release and reuptake of the neurotransmitter glutamate was investigated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. V. B. Sokolov, A. Yu. Aksinenko, N. S. Nikolaeva, V. V. Grigor´ev, A. S. Kinzirsky, S. O. Bachurin, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 1137 [Izv. Akad. Nauk, Ser. Khim., 2014, 1137].

    Article  CAS  Google Scholar 

  2. V. I. Skvortsova, S. O. Bachurin, O. D. Razinskaya, A. P. Smirnov, E. A. Kovrazhkina, K. I. Pochigaeva, N. N. Ninkina, T. A. Shelkovnikova, A. A. Ustyugov, Zh. Nevrologii Psikhiatrii im. S.S. Korsakova [Korsakov J. Neurology Psychi- atry], 2011, 4 (in Russian).

    Google Scholar 

  3. V. V. Grigor´ev, A. N. Proshin, A. S. Kinzirskii, S. O. Bachurin, Russ. Chem. Rev., 2009, 78, 524 [Usp. Khim., 2009, 78, 524].

    Google Scholar 

  4. V. B. Sokolov, A. Yu. Aksinenko, Russ. Chem. Bull. (Engl. Transl.), 1998, 727 [Izv. Akad. Nauk, Ser. Khim., 1998, 748].

    Google Scholar 

  5. S. N. Osipov, V. B. Sokolov, A. F. Kolomiets, I. V. Martynov, A. V. Fokin, Bull. Acad. Sci., Div. Chem. Sci. (Engl. Transl.), 1987, 36, 1098 [Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 1185].

    Article  Google Scholar 

  6. V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, I. V. Martynov, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 2851 [Izv. Akad. Nauk, Ser. Khim., 2005, 2755].

    Article  CAS  Google Scholar 

  7. V. B. Sokolov, A. Yu. Aksinenko, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 2252 [Izv. Akad. Nauk, Ser. Khim., 2007, 2176].

    Article  CAS  Google Scholar 

  8. V. B. Sokolov, A. Yu. Aksinenko, I. V. Martynov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 2247 [Izv. Akad. Nauk, Ser. Khim., 2007, 2171].

    Article  CAS  Google Scholar 

  9. V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, I. V. Martynov, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 472 [Izv. Akad. Nauk, Ser. Khim., 2005, 462].

    Article  CAS  Google Scholar 

  10. V. B. Sokolov, A. Yu. Aksinenko, I. V. Martynov, Izv. Akad. Nauk, Ser. Khim., 2001, 1064 [Russ. Chem. Bull. (Int. Ed.), 2001, 50, 1113].

    Google Scholar 

  11. V. B. Sokolov, A. Yu. Aksinenko, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 1514 [Izv. Akad. Nauk, Ser. Khim., 2005, 1470].

    Article  CAS  Google Scholar 

  12. O. V. Korechenko, A. Yu. Aksinenko, V. B. Sokolov, A. N. Pushin, I. V. Martynov, Russ. Chem. Bull. (Engl. Transl.), 1995, 44, 1740 [Izv. Akad. Nauk, Ser. Khim., 1995, 1809].

    Article  Google Scholar 

  13. V. B. Sokolov, A. Yu. Aksinenko, I. V. Martynov, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 472 [Izv. Akad. Nauk, Ser. Khim., 2005, 460].

    Article  CAS  Google Scholar 

  14. L. M. Zhou, Z. Q. Gu, A. M. Costa, K. A. Yamada, P. E. Mansson, T. Giordano, P. Skolnick, K. A. Jones, J. Pharmacol. Exp. Ther., 1997, 280,422.

    CAS  Google Scholar 

  15. L. L. Coughenour, B. M. Barr, J. Pharmacol. Exp. Ther., 2001, 296,150.

    CAS  Google Scholar 

  16. W. Hatzenlaub, W. Pfleiderer, Lieb. Ann. Chem., 1979, 1847.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. B. Sokolov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0099—0103, January, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sokolov, V.B., Aksinenko, A.Y., Sokolov, A.V. et al. Modification of biologically active amides and amines with fluorine-containing heterocycles 12.* Endo- and exocyclic modifications of the drug riluzole with trifluoromethyl-containing heterocycles. Russ Chem Bull 66, 99–103 (2017). https://doi.org/10.1007/s11172-017-1706-y

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1706-y

Keywords

Navigation