Synthesis, Structure and Cytoprotective Activity of New Derivatives of 4-Aryl-3-Aminopyridin-2(1H)-One

Molecules, 2025

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DOI 10.3390/molecules30163331
Data confidence 85 high
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Abstract

As a continuation of our research on the synthesis and study of biological properties of new derivatives of 3-aminopyridin-2(1H)-ones, we investigated the Leuckart–Wallach and Eschweiler–Clarke reactions with selected 3-aminopyridin-2(1H)-ones and 3-(arylmethyl)pyridin-2(1H)-ones. It was found that under the conditions of the Leuckart–Wallach reaction with aromatic aldehydes in formic acid, mainly formamides of the indicated 3-aminopyridones are formed. The Eschweiler–Clarke reaction of 3-aminopyridin-2(1H)-ones and 3-(arylmethyl)pyridin-2(1H)-ones with an aqueous solution of formaldehyde result in the formation of tertiary N–benzyl(methyl)amino)-pyridin-2(1H)-ones in almost quantitative yield. The 3-aminopyridin-2(1H)-ones derivatives synthesized by us were used for the biological screening of cytoprotective activity in the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test to determine the viability of fibroblast cells isolated from the NIH/Swiss mouse embryo (NIH/3T3, Gibco). It was found that many of the studied compounds under the conditions of our experiment exhibited significant cytoprotective effects, thereby enhancing cell survival.