S-Aroylthiooximes: A Facile Route to Hydrogen Sulfide Releasing Compounds with Structure-Dependent Release Kinetics

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• 作者：Jeffrey C. Foster ; Chadwick R. Powell ; Scott C. Radzinski ; John B. Matson
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 21, 2014
• 年：2014
• 卷：16
• 期：6
• 页码：1558-1561
• 全文大小：246K
• 年卷期：v.16,no.6(March 21, 2014)
• ISSN：1523-7052

文摘

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鈥?2 min by substitution of the SATHA ring. The pseudo-first-order rate constants of substituted SATOs fit standard linear free energy relationships (蟻 = 1.05), demonstrating a significant sensitivity to electronic effects.