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Synthesis and Study of Psychotropic Activity of 1-Substituted 4-Amino-5-oxoprolines

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Abstract

1-Substituted (2S,4S)-4-amino-5-oxoprolines have been obtained by nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloylglutamate followed by isolation of the predominant (2S,4S)-diastereomer and removal of protecting groups. The psychotropic activity of the obtained compounds has been studied after a single administration in experimental animals. 4-Amino-1-(4-bromophenyl)-5-oxoproline and especially 4-amino-1-(4-aminophenyl)-5-oxoproline showed pronounced anxiolytic activity in the Elevated plus maze test. (2S,4S)-4-Amino-5-oxoprolines containing 4-methylphenyl, 4-bromophenyl, 4‑aminophenyl, and 2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl substituents at the 1-position exhibited nootropic activity: they improved the formation and retention of the memory trace in the Passive avoidance test and the Active avoidance test (Extrapolation escape test).

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ACKNOWLEDGMENTS

This work was performed using the equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences.

Funding

This work was supported by the Russian Foundation for Basic Research (project no. 20–43–660045 r_a).

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Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620108, Yekaterinburg, Russia

    A. Yu. Vigorov, V. P. Krasnov, I. A. Nizova, L. Sh. Sadretdinova, G. L. Levit, T. V. Matveeva, P. A. Slepukhin &  V. N. Charushin

  2. Ural Federal University, 620002, Yekaterinburg, Russia

    V. P. Krasnov &  V. N. Charushin

  3. Department of Pharmacology and Pharmacy, Institute of Continuing Medical and Pharmaceutical Education, Volgograd State Medical University, Ministry of Health of the Russian Federation, 400087, Volgograd, Russia

    D. A. Bakulin, N. S. Kovalyov &  I. N. Tyurenkov

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  1. A. Yu. Vigorov
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  2. V. P. Krasnov
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  3. I. A. Nizova
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  4. L. Sh. Sadretdinova
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  5. G. L. Levit
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  6. T. V. Matveeva
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  7. P. A. Slepukhin
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  8. D. A. Bakulin
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  9. N. S. Kovalyov
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  10. I. N. Tyurenkov
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  11. V. N. Charushin
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Corresponding author

Correspondence to V. P. Krasnov.

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Сonflict of interest. The authors declare no conflict of interest.

Statement on the welfare of animals. All experiments were conducted in accordance with the standards for animal studies established by the law of the Russian Federation and EASC technical standards for Good Laboratory Practice (State Standards R 53434-2009 and R 51000.4-2011).

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Translated by I. Kudryavtsev

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Vigorov, A.Y., Krasnov, V.P., Nizova, I.A. et al. Synthesis and Study of Psychotropic Activity of 1-Substituted 4-Amino-5-oxoprolines. Dokl Chem 494, 131–135 (2020). https://doi.org/10.1134/S0012500820090049

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