Synthesis, structure, and biological activity of 4-hetaryl-2-pyrrolidones containing a pyrazole ring

Chem Heterocycl Compd (N Y). 2022;58(11):598-607. doi: 10.1007/s10593-022-03140-4. Epub 2022 Nov 30.

Abstract

Single diastereomers of 4-hetaryl-2-pyrrolidone-3(5)-carbo- and 2-[4-hetaryl-2-pyrrolidon-1-yl]acetohydrazides were used in reactions with 2,4-pentanedione, providing (3R*,4S*)-3-, (4R*,5R*)-5-(3,5-dimethyl-1H-pyrazole-1-carbonyl)- and 1-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-oxoethyl]-4-hetaryl-2-pyrrolidones. The structures of the synthesized compounds were confirmed by spectral methods and X-ray structural analysis. Some of the obtained compounds were shown to possess nootropic and anxiolytic activity.

Supplementary information: The online version contains supplementary material available at 10.1007/s10593-022-03140-4.

Keywords: 2-pyrrolidone; 3,5-dimethylpyrazole; X-ray structural analysis; biological activity; carbohydrazides; hydrazides; racetams.