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

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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.

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References

  1. M. B. Dewal, A. S. Wani, C. Vidaillac, D. Oupicky, M. J. Rybak, S. M. Firestine, Eur. J. Med. Chem., 2012, 51, 145.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. D. Hung, E. Chorell, H. Uvell, J. S. Pinkner, S. J. Hultgren, F. Almqvist, Org. Biomol. Chem., 2014, 12, 1942.

    Article  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  5. R. N. De La Fuente, A. Mills, A. S. Verkman, Mol. Pharmacol., 2008, 73, 758.

    Article  CAS  PubMed  Google Scholar 

  6. L. Aurelio, H. Figler, B. L. Flynn, J. Linden, P. J. Scammells, Bioorg. & Med. Chem., 2008, 16, 1319.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  8. A. Davoodnia, H. Behmadi, A. Zare Bidaki, M. Bakavoli, N. Tavakoli Hoseini, Chinese Chem. Lett., 2007, 18, 1163.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  12. V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, I. V. Martynov, Russ. Chem. Bull., 2005, 54, 472.

    Article  CAS  Google Scholar 

  13. V. B. Sokolov, A. Yu. Aksinenko, A. V. Sokolov, A. Gabrelian, A. D. Efimova, V. V. Grigoriev, Russ. Chem. Bull., 2017, 66, 99.

    Article  CAS  Google Scholar 

  14. V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva, I. V. Martynov, Russ. Chem. Bull., 2010, 59, 197.

    Article  CAS  Google Scholar 

  15. V. B. Sokolov, A. Yu. Aksinenko, Russ. Chem. Bull., 2012, 61, 2124.

    Article  CAS  Google Scholar 

  16. C. Dana, J. Benavides, H. Schoemaker, B. Scatton, Neurosci. Lett., 1991, 125, 45.

    Article  CAS  PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  18. L. Yao, Q. Zhou, Neural Plast., 2017, 2017, 2875904.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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.

    Article  Google Scholar 

  20. K. Gewald, E. Schinke, H. Bottcher, Chem. Ber., 1966, 99, 94.

    Article  CAS  Google Scholar 

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Correspondence to A. Yu. Aksinenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2253–2258, December, 2018.

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Sokolov, V.B., Aksinenko, A.Y., Dranyi, O.A. et al. Methyl esters of 2-aminotetrahydrobenzothiophene-3-carboxylic acids decorated with trifluoromethyl-containing heterocycles. Russ Chem Bull 67, 2253–2258 (2018). https://doi.org/10.1007/s11172-018-2365-3

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  • DOI: https://doi.org/10.1007/s11172-018-2365-3

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