1,2-硫乙烯-4-胺和1,2-硫乙烯-5-胺的高效可扩展合成

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Synthesis-Stuttgart Pub Date : 2022-10-25 DOI:10.1055/a-2022-1398

Lukas Zeisel, M. Maier, O. Thorn-Seshold

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引用次数: 1

摘要

我们开发了第一个区域选择性合成1,2-硫乙烯-4-胺(TSA4)和1,2-硫乙烯-5-胺(TSA5):具有氧化还原活性的基序，在化学生物学上具有很高的价值，迄今为止被繁琐的合成所阻碍。我们利用一个叠氮中间体和一个动力学控制的s -酰化来进行区域选择性的硫离子安装。我们优化了短，快速的序列，只需一个或两个色谱步骤，廉价地提供这些基序，用于高通量抑制剂筛选，并为组装其他亚硒基硫化物提供了一种强大的方法。

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Efficient and Scalable Syntheses of 1,2-Thiaselenane-4-amine and 1,2-Thiaselenane-5-amine

We develop the first regioselective syntheses of 1,2-thiaselenane-4-amine (TSA4) and 1,2-thiaselenane-5-amine (TSA5): redox-active motifs with high value in chemical biology, that until now were hindered by tedious synthesis. We leverage an aziridine intermediate and a kinetically controlled S-acylation for regioselective chalcogen installations. We optimise short, fast sequences with just one or two chromatographic steps that cheaply deliver these motifs on scale for high-throughput inhibitor screening, and provide a robust methodology for assembling other selenenylsulfides.

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来源期刊

Synthesis-Stuttgart 化学-有机化学

CiteScore

4.50

自引率

7.70%

发文量

435

审稿时长

1 months

期刊介绍： SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.