Advertisement

Russian Chemical Bulletin

, Volume 67, Issue 12, pp 2253–2258 | Cite as

Methyl esters of 2-aminotetrahydrobenzothiophene-3-carboxylic acids decorated with trifluoromethyl-containing heterocycles

  • V. B. Sokolov
  • A. Yu. AksinenkoEmail author
  • O. A. Dranyi
  • V. V. Grigoriev
Full Articles
  • 4 Downloads

Abstract

Methyl 2-aminothiophene-3-carboxylates were modified with trifluoromethyl-containing five-membered heterocycles by cyclocondensation of methyl trifluoropyruvate N-thiophen-2-ylimines with 1,3-N,N-binucleophiles (2-aminothiazoline and benzamidines) to obtain the corresponding 5-oxo-6-trifluoromethyl-2,3,5,6-tetrahydroimidazoles and 5-oxo-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazoles. Radioligand binding was used to study the in fluence of the synthesized compounds on the neuronal NMDA receptors.

Key words

methyl 2-aminothiophene-3-carboxylates methyl trifluoropyruvate methyl trifluoropyruvate thiophene-2-ylimines 2-aminothiazoline benzamidines 5-oxo-6-trifluoromethyl-2,3,5,6-tetrahydroimidazoles 5-oxo-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazoles cyclocondensation NMDA receptors radioligand binding 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. B. Dewal, A. S. Wani, C. Vidaillac, D. Oupicky, M. J. Rybak, S. M. Firestine, Eur. J. Med. Chem., 2012, 51, 145.CrossRefGoogle Scholar
  2. 2.
    D. Hung, E. Chorell, H. Uvell, J. S. Pinkner, S. J. Hultgren, F. Almqvist, Org. Biomol. Chem., 2014, 12, 1942.CrossRefGoogle Scholar
  3. 3.
    B. Kumar Biswas, Y. R. Malpani, N. Ha, D.-H. Kwon, J. S. Shin, H.-S. Kim, C. Kim, S. B. Han, C.-K. Lee, Y.-S. Jung, Bioorg. Med. Chem. Lett., 2017, 27, 3582.CrossRefGoogle Scholar
  4. 4.
    B. M. Katzman, R. E. Perszyk, H. Yuan, Y. A. Tahirovic, A. E. Sotimehin, S. F. Traynelis, D. C. Liotta, Bioorg. Med. Chem. Lett., 2015, 25, 5583.CrossRefGoogle Scholar
  5. 5.
    R. N. De La Fuente, A. Mills, A. S. Verkman, Mol. Pharmacol., 2008, 73, 758.CrossRefGoogle Scholar
  6. 6.
    L. Aurelio, H. Figler, B. L. Flynn, J. Linden, P. J. Scammells, Bioorg. & Med. Chem., 2008, 16, 1319.CrossRefGoogle Scholar
  7. 7.
    P. G. Baraldi, M. G. Pavani, J. C. Shryock, A. R. Moorman, V. Iannotta, P. A. Borea, R. Romagnoli, Eur. J. Med. Chem., 2004, 39, 855.CrossRefGoogle Scholar
  8. 8.
    A. Davoodnia, H. Behmadi, A. Zare Bidaki, M. Bakavoli, N. Tavakoli Hoseini, Chinese Chem. Lett., 2007, 18, 1163.CrossRefGoogle Scholar
  9. 9.
    R. J. Patch, C. A. Baumann, J. Liu, A. C. Gibbs, H. Ott, J. Lattanze, M. R. Player, Bioorg. Med. Chem. Lett., 2006, 16, 3282.CrossRefGoogle Scholar
  10. 10.
    Yu. Gui Gu, A. S. Florjanic, R. F. Clark, T. Zhang, C. S. Cooper, D. D. Anderson, C. G. Lerner, J. O. McCall, Y. Cai, C. L. Black-Schaefer, G. F. Stamper, P. J. Hajduk, B. A. Beutel, Bioorg. Med. Chem. Lett., 2004, 14, 267.CrossRefGoogle Scholar
  11. 11.
    V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, A. N. Pushin, I. V. Martynov, Russ. Chem. Bull., 2005, 54, 1667.CrossRefGoogle Scholar
  12. 12.
    V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, I. V. Martynov, Russ. Chem. Bull., 2005, 54, 472.CrossRefGoogle Scholar
  13. 13.
    V. B. Sokolov, A. Yu. Aksinenko, A. V. Sokolov, A. Gabrelian, A. D. Efimova, V. V. Grigoriev, Russ. Chem. Bull., 2017, 66, 99.CrossRefGoogle Scholar
  14. 14.
    V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, I. V. Martynov, Russ. Chem. Bull., 2010, 59, 197.CrossRefGoogle Scholar
  15. 15.
    V. B. Sokolov, A. Yu. Aksinenko, Russ. Chem. Bull., 2012, 61, 2124.CrossRefGoogle Scholar
  16. 16.
    C. Dana, J. Benavides, H. Schoemaker, B. Scatton, Neurosci. Lett., 1991, 125, 45.CrossRefGoogle Scholar
  17. 17.
    G. Nowak, R. Trullas, R. T. Layer, P. Skolnick, I. A. Paul, J. Pharmacol. Exp. Ther., 1993, 265, 1380.Google Scholar
  18. 18.
    L. Yao, Q. Zhou, Neural Plast., 2017, 2017, 2875904.CrossRefGoogle Scholar
  19. 19.
    N. Warikoo, S. J. Brunwasser, A. Benz, H. J. Shu, S. M. Paul, M. Lewis, J. Doherty, M. Quirk, L. Piccio, C. F. Zorumski, G. S. Day, S. J. Mennerick, Neurosci., 2018, 38, 3218.CrossRefGoogle Scholar
  20. 20.
    K. Gewald, E. Schinke, H. Bottcher, Chem. Ber., 1966, 99, 94.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • V. B. Sokolov
    • 1
  • A. Yu. Aksinenko
    • 1
    Email author
  • O. A. Dranyi
    • 1
  • V. V. Grigoriev
    • 1
  1. 1.Institute of Physiologically Active CompoundsRussian Academy of SciencesChernogolovkaRussian Federation

Personalised recommendations