3716-62-9Relevant academic research and scientific papers
Synthesis and Evaluation of the Psychotropic Activity of Framework Derivatives of Alpha-Pyrrolidone
Abrosimova, E. E.,Bakulin, D. A.,Kazachkova, M. S.,Klimochkin, Yu. N.,Kovalev, N. S.,Kurkin, D. V.,Reznikov, A. N.,Shiryaev, V. A.,Tkachenko, I. M.,Tyurenkov, I. N.
, p. 1276 - 1287 (2021/12/23)
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.
Fast, acid-free, and selective lactamization of lactones in ionic liquids
Orrling, Kristina M.,Wu, Xiongyu,Russo, Francesco,Larhed, Mats
supporting information; experimental part, p. 8627 - 8630 (2009/04/11)
(Chemical Equation Presented) A fast and acid-free one-pot 0.2-30 mmol microwave methodology for direct ionic liquid-mediated preparation of lactams from lactones and primary amines has been developed. The protocol was investigated with a wide range of primary amines and a handful of lactones, including substrates with acid-sensitive substituents. Both γ-lactams and δ-lactams were, despite the complete absence of a Bronsted acid, obtained in useful to excellent yields after only 35 min of microwave processing.
