磺酰基对 2-磺酰基肼亚基 1,3-二羰基化合物生物活性的影响

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-07-26 DOI:10.1007/s11172-024-4294-7

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

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引用次数: 0

摘要

含有砜片段的芳基偶氮氯化物与（三氟）乙酰乙酸乙酯和乙酰丙酮发生偶氮偶联反应，生成了 2-磺酰基肼亚基 1,3-二羰基化合物。核磁共振光谱显示，2-磺酰基肼亚基 3-氧代酯在溶液中以 Z-异构体形式存在。在合成的三氟甲基取代 3- 氧代酯中发现了对乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）和羧酸酯酶（CES）这三种丝氨酸酯酶的微摩尔抑制剂。在三氟甲基取代的 1,3-二酮衍生物中发现了一种纳摩尔 BChE 抑制剂，它对 BChE 具有选择性，同时还具有自由基清除活性。研究还发现了对脑膜炎菌株的致病真菌具有中等活性的 3-氧代酯。

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

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.

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.