Skip to main content
Log in

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

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

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.

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. 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.

    Article  CAS  PubMed  Google Scholar 

  2. R. Fuente, W. Namkung, A. Mills, A. S. Verkman, Mol. Pharmacol., 2007, 73, 758; DOI: 10.1124/mol.107.043208.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  PubMed  PubMed Central  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  7. C. W. Murray, D. C. Rees, Nat. Chem., 2009, 1, 187; DOI: 10.1038/nchem.217.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  9. M. Bashir, A. Bano, A. S. Ijaz, B. A. Chaudhary, Molecules, 2015, 20, 13496; DOI: 10.3390/molecules200813496.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  12. B. H. Lee, T. G. Geary, J. P. Davis, J. W. Bowman, Pat. WO 2003101979, 2003.

    Google Scholar 

  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. C. Dana, J. Benavides, H. Schoemaker, B. Scatton, Neurosci. Lett., 1991, 125, 45; DOI: 10.1016/0304-3940(91)90127-F.

    Article  CAS  PubMed  Google Scholar 

  15. G. Nowak, R. Trullas, R. T. Layer, P. Skolnick, I. A. Paul, J. Pharmacol. Exp. Ther., 1993, 265, 1380.

    CAS  PubMed  Google Scholar 

  16. L. Yao, Q. Zhou, Neural Plast., 2017, 2017, 2875904; DOI: 10.1155/2017/2875904.

    Google Scholar 

  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.

    Article  PubMed  PubMed Central  Google Scholar 

  18. K. Gewald, E. Schinke, H. Bottcher, Chem. Ber., 1966, 99, 94; DOI: 10.1002/cber.19660990116.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Aksinenko.

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., Gabrel’yan, A.V. et al. Methyl N-(carbazolyl)acetyl-2-aminotetrahydrobenzothiophene-3-carboxylates as modulators of NMDA receptors. Russ Chem Bull 68, 1629–1632 (2019). https://doi.org/10.1007/s11172-019-2602-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2602-4

Key words

Navigation