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Russian Chemical Bulletin

, Volume 68, Issue 8, pp 1629–1632 | Cite as

Methyl N-(carbazolyl)acetyl-2-aminotetrahydrobenzothiophene-3-carboxylates as modulators of NMDA receptors

  • V. B. Sokolov
  • A. Yu. AksinenkoEmail author
  • A. V. Gabrel’yan
  • V. V. Grigoriev
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  • 3 Downloads

Abstract

Methyl N-(carbazolyl)acetyl-2-aminotetrahydrothiophene-3-carboxylates were synthesized by alkylation of carbazoles with the corresponding chloroacetylamides of 2-aminotiophenes. The radioligand binding method showed the presence of the modulating effect of the synthesized compounds on the neuronal NMDA receptors.

Key words

methyl 2-aminothiophene-3-carboxylates NMDA receptors radioligand binding 

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References

  1. 1.
    Y. Sun, J. Fan, Z. Zhu, X. Guo, T. Zhou, W. Duan, X. Shen, Eur. J. Pharmacol., 2015, 762, 202–213; DOI: 10.1016/j.ejphar.2015.05.050.CrossRefGoogle Scholar
  2. 2.
    R. Fuente, W. Namkung, A. Mills, A. S. Verkman, Mol. Pharmacol., 2007, 73, 758; DOI: 10.1124/mol.107.043208.CrossRefGoogle Scholar
  3. 3.
    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; DOI: 10.1016/j.bmcl.2015.10.046.CrossRefGoogle Scholar
  4. 4.
    R. Perszyk, B. M. Katzman, H. Kusumoto, S. A. Kell, M. P. Epplin, Y. A. Tahirovic, R. L. Moore, D. Menaldino, P. Burger, D. C. Liotta, S. F. Traynelis, eLife, 2018; 7, e34711; DOI: 10.7554/eLife.34711.CrossRefGoogle Scholar
  5. 5.
    V. V. Grigoriev, V. L. Zamoyski, A. V. Aksinenko, V. B. Sokolov, S. O. Bachurin, Dokl. Biochem. Biophys., 2018, 483, 293; DOI: 10.1134/S1607672918060042.CrossRefGoogle Scholar
  6. 6.
    V. B. Sokolov, A. Yu. Aksinenko, O. A. Dranyi, V. V. Grigoriev, Russ. Chem. Bull., 2018, 67, 2253; DOI: 10.1007/s11172-018-2365-3.CrossRefGoogle Scholar
  7. 7.
    C. W. Murray, D. C. Rees, Nat. Chem., 2009, 1, 187; DOI: 10.1038/nchem.217.CrossRefGoogle Scholar
  8. 8.
    M. G. Savelief, G. Nam, J. Kang, H. J. Lee, M. Lee, M. H. Lim, Chem. Rev., 2019, 119, 1221; DOI: 10.1021/acs. chemrev.8b00138.CrossRefGoogle Scholar
  9. 9.
    M. Bashir, A. Bano, A. S. Ijaz, B. A. Chaudhary, Molecules, 2015, 20, 13496; DOI: 10.3390/molecules200813496.CrossRefGoogle Scholar
  10. 10.
    K. S. MacMillan, J. Naidoo, J. Liang, L. Melito, N. S. Williams, L. Morlock, P. J. Huntington, S. J. Estill, J. Longgood, G. L. Becker, S. L. McKnight, A. A. Pieper, J. K. De Brabander, J. M. Ready, J. Am. Chem. Soc., 2011, 133, 1428; DOI: 10.1021/ja108211m.CrossRefGoogle Scholar
  11. 11.
    V. B. Sokolov, G. F. Makhaeva, A. Yu. Aksinenko, V. V. Grigoriev, E. F. Shevtsova, S. O. Bachurin, Russ. Chem. Bull. Int. Ed.), 2017, 66, 1821; DOI: 10.1007/s11172-017-1953-y.CrossRefGoogle Scholar
  12. 12.
    B. H. Lee, T. G. Geary, J. P. Davis, J. W. Bowman, Pat. WO 2003101979, 2003.Google Scholar
  13. 13.
    D. S. Khachatryan, V. S. Osipov, R. A. Sandu, V. N. Danilenko, A. V. Kolotaev, O. A. Zhdanovich, O. B. Bekker, K. R. Matevosyan, Pat. RF 2629369, 2017 (in Russian).Google Scholar
  14. 14.
    C. Dana, J. Benavides, H. Schoemaker, B. Scatton, Neurosci. Lett., 1991, 125, 45; DOI: 10.1016/0304-3940(91)90127-F.CrossRefGoogle Scholar
  15. 15.
    G. Nowak, R. Trullas, R. T. Layer, P. Skolnick, I. A. Paul, J. Pharmacol. Exp. Ther., 1993, 265, 1380.Google Scholar
  16. 16.
    L. Yao, Q. Zhou, Neural Plast., 2017, 2017, 2875904; DOI: 10.1155/2017/2875904.Google Scholar
  17. 17.
    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, J. Neurosci., 2018, 38, 3218; DOI: 10.1523/JNEUROSCI.3377-17.2018.CrossRefGoogle Scholar
  18. 18.
    K. Gewald, E. Schinke, H. Bottcher, Chem. Ber., 1966, 99, 94; DOI: 10.1002/cber.19660990116.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • V. B. Sokolov
    • 1
  • A. Yu. Aksinenko
    • 1
    Email author
  • A. V. Gabrel’yan
    • 1
  • V. V. Grigoriev
    • 1
  1. 1.Institute of Physiologically Active CompoundsRussian Academy of SciencesChernogolovka, Moscow RegionRussian Federation

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