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

被引：1

作者：

Elkina, N. A. ^{[1
]}

Khudina, O. G. ^{[1
]}

Burgart, Ya. V. ^{[1
]}

Shchegolkov, E. V. ^{[1
]}

Serebryakova, O. G. ^{[2
]}

Rudakova, E. V. ^{[2
]}

Boltneva, N. P. ^{[2
]}

Kovaleva, N. V. ^{[2
]}

Makhaeva, G. F. ^{[2
]}

Gerasimova, N. A. ^{[3
]}

Evstigneeva, N. P. ^{[3
]}

Saloutin, V. I. ^{[1
]}

机构：

[1] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, 22Ul S Kovalevskoi, Ekaterinburg 620108, Russia

[2] Russian Acad Sci, Inst Physiol Act Cpds, Fed Res Ctr Problems Chem Phys & Med Chem, 1 Severny proezd, Moscow 142432, Russia

[3] Ural Res Inst Dermatovenerol & Immunopathol, 8 Ul Shcherbakova, Ekaterinburg 620076, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2024年 / 73卷 / 06期

关键词：

2-sulfonarylhydrazinylidene-1,3 dicarbonyl compounds; azo-coupling; esterase profile; carboxylesterase; acetylcholinesterase; butyrylcholinesterase; inhibitors; radical-scavenging activity; antimicrobial activity; HUMAN INTESTINAL CARBOXYLESTERASE; ESTERASE PROFILES; INHIBITORS; DISCOVERY; CHOLINESTERASE; SULFONAMIDES; IRINOTECAN; EFFICIENT; DESIGN;

D O I：

10.1007/s11172-024-4294-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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.

引用

页码：1766 / 1774

页数：9

共 38 条

[1] Design, synthesis, analgesic, anti-inflammatory activity of novel pyrazolones possessing aminosulfonyl pharmacophore as inhibitors of COX-2/5-LOX enzymes: Histopathological and docking studies [J].