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

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
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

Abstract

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.

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
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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来源期刊
Russian Chemical Bulletin
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.
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