Influence of the sulfonyl group on the biological activity of 2-sulfonarylhydrazinylidene 1,3-dicarbonyl compounds

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发表日期：

2024年6月1日

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N. A. Elkina,
O. G. Khudina,
Ya. V. Burgart,
E. V. Shchegolkov,
O. G. Serebryakova,
E. V. Rudakova,
N. P. Boltneva,
N. V. Kovaleva,
G. F. Makhaeva,
N. A. Gerasimova,
N. P. Evstigneeva,
V. I. Saloutin

摘要

The azo-coupling reaction of aryldiazonium chlorides containing a sulfone fragment with ethyl (trifluoro)acetylacetates and acetylacetone led to 2-sulfonarylhydrazinylidene 1,3-dicarbonyl compounds. According to NMR spectroscopy, 2-sulfonarylhydrazinylidene 3-oxoesters exist in solutions as Z-isomers. Micromolar inhibitors of three serine esterases, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and carboxylesterase (CES), were found among the synthesized trifluoromethyl-substituted 3-oxoesters. A nanomolar BChE inhibitor was identified among the trifluoromethyl-substituted 1,3-diketone derivatives exhibiting selectivity towards BChE in combination with radical-scavenging activity. 3-Oxoesters with moderate activity against pathogenic fungi of the T. mentagrophytes strain were revealed.