Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
Org Lett. 2014 Mar 21;16(6):1558-61. doi: 10.1021/ol500385a. Epub 2014 Feb 27.
We report the facile preparation of a family of S-aroylthiooxime (SATO) H2S donors, which are synthesized via a click reaction analogous to oxime formation between S-aroylthiohydroxylamines (SATHAs) and aldehydes or ketones. Analysis of cysteine-triggered H2S release revealed structure-dependent release kinetics with half-lives from 8-82 min by substitution of the SATHA ring. The pseudo-first-order rate constants of substituted SATOs fit standard linear free energy relationships (ρ = 1.05), demonstrating a significant sensitivity to electronic effects.
我们报告了一种 S-芳酰基硫代肟（SATO）H2S 供体的简便制备方法，该方法通过类似于 S-芳酰基硫代羟胺（SATHAs）与醛或酮之间肟形成的点击反应合成。对半胱氨酸触发的 H2S 释放分析表明，通过取代 SATHA 环，释放动力学具有结构依赖性，半衰期为 8-82 分钟。取代 SATO 的假一级速率常数符合标准线性自由能关系（ρ=1.05），这表明它们对电子效应具有显著的敏感性。
