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

• Published in: Doklady. Chemistry 2020-09, Vol.494 (1), p.131-135
• Main Authors: Vigorov, A. Yu, Krasnov, V. P., Nizova, I. A., Sadretdinova, L. Sh, Levit, G. L., Matveeva, T. V., Slepukhin, P. A., Bakulin, D. A., Kovalyov, N. S., Tyurenkov, I. N., Charushin, V. N.
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Industrial Chemistry/Chemical Engineering
• ISSN: 0012-5008; 1608-3113
• DOI: 10.1134/S0012500820090049

1-Substituted (2 S ,4 S )-4-amino-5-oxoprolines have been obtained by nucleophilic substitution of bromine in dimethyl (2 S ,4 RS )-4-bromo- N -phthaloylglutamate followed by isolation of the predominant (2 S ,4 S )-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. (2 S ,4 S )-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).