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

• Published in: Russian chemical bulletin Vol. 73; no. 6; pp. 1766 - 1774
• Main Authors: Elkina, N. A., Khudina, O. G., Burgart, Ya. V., Shchegolkov, E. V., Serebryakova, O. G., Rudakova, E. V., Boltneva, N. P., Kovaleva, N. V., Makhaeva, G. F., Gerasimova, N. A., Evstigneeva, N. P., Saloutin, V. I.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.06.2024; Springer Nature B.V
• Subjects: Acetylacetone; Biological activity; Carbonyl compounds; Chemical reactions; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Diketones; Esterases; Full Articles; Inorganic Chemistry; NMR spectroscopy; Organic Chemistry; Scavenging; Substitutes; inhibitors; radical-scavenging activity; butyrylcholinesterase; 2-sulfonarylhydrazinylidene-1,3 dicarbonyl compounds; carboxylesterase; acetylcholinesterase; esterase profile; antimicrobial activity; azo-coupling
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-024-4294-7

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.