Synthesis and Evaluation of the Psychotropic Activity of Framework Derivatives of Alpha-Pyrrolidone View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2021-11

AUTHORS

Yu. N. Klimochkin, I. M. Tkachenko, A. N. Reznikov, V. A. Shiryaev, M. S. Kazachkova, N. S. Kovalev, D. A. Bakulin, E. E. Abrosimova, D. V. Kurkin, I. N. Tyurenkov

ABSTRACT

Derivatives of alpha-pyrrolidone and some derivatives of adamantane possess a wide spectrum of psychotropic activity. The synthesis of adamantane and homoadamantane derivatives of alpha-pyrrolidone and the assessment of their psychotropic activity were performed. A number of framework compounds containing a pyrrolidin-2-one fragment either in the side chain or as part of the framework system were synthesized. N-(Adamantan-1-yl)pyrrolidin-2-one (TIM-2) was obtained by the reaction of 1-bromadamantane with pyrrolidin-2-one. Homoadamantane-fused pyrrolidin-2-one (TIM-1) was obtained from β-dicarbonyl derivatives of homoadamantane. Synthesis of the starting 2-(5-oxohomoadamantyl)acetic acid was carried out by cleavage of the corresponding keto diester or cyanoketo ester of homoadamantane under the conditions of the Holler–Bauer reaction with sonication. Then, the resulting γ-keto acid was introduced into the Leuckart–Wallach reaction to obtain cis-decahydro-4,8:6,10-dimethanocyclononane[b]pyrrol-2(1H)-one (TIM-1). The psychotropic activity of the obtained compounds was evaluated in standard behavioral tests in experimental animals. Compound TIM-2 exhibited pronounced anxiolytic, antidepressant, and nootropic activity. Compound binding assays were performed by molecular docking of the synthesized compounds to the GABA-B receptor, which also showed high binding energies for TIM-2. More... »

PAGES

1276-1287

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1068162021060108

DOI

http://dx.doi.org/10.1134/s1068162021060108

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1143943697


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