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

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 (3 R* ,4 S* )-3-, (4 R* ,5 R* )-5-(3,5-dimethyl-1 H -pyrazole-1-carbonyl)- and 1-[2-(3,5-dimethyl-1 H -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.