含磺酰胺的二苯并[1,4]硫氮杂卓的合成及其碳酸酐酶活性研究

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC Chemistry of Heterocyclic Compounds Pub Date : 2024-01-09 DOI:10.1007/s10593-024-03279-2

Daria S. Smirnova, Vladimir V. Sharoiko, Stanislav A. Kalinin, Alexander V. Sapegin

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引用次数: 0

摘要

以伯胺和 2-[(2-硝基-4-氨基磺酰基苯基)硫]苯甲酸为前体，开发了一种获得二苯并[1,4]硫氮杂卓含磺酰胺衍生物的单锅合成方法。该方法以一系列酰胺化步骤以及随后的斯迈尔斯重排和变硝基环化反应串联为基础。由此产生的三环系统作为牛碳酸酐酶同工酶 II 的抑制剂显示出明显的活性。

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The synthesis and study of carbonic anhydrase activity of sulfonamide-containing dibenzo[1,4]thiazepines

A one-pot synthesis approach to access sulfonamide-containing derivatives of dibenzo[1,4]thiazepine using primary amines and 2-[(2-nitro-4-sulfamoylphenyl)sulfanyl]benzoic acid as precursors was developed. The approach is based on a sequence of amidation steps and the subsequent tandem of the Smiles rearrangement and denitrocyclization reaction. The resulting tricyclic systems showed pronounced activity as inhibitors of bovine carbonic anhydrase isoform II.

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来源期刊

Chemistry of Heterocyclic Compounds 化学-有机化学

CiteScore

2.90

自引率

13.30%

发文量

审稿时长

1 months

期刊介绍： The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemoratives dedicated to prominent heterocyclic chemists.