S-aroylthiooximes: A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics

Jeffrey C. Foster; Chadwick R. Powell; Scott C. Radzinski; John B. Matson

doi:10.1021/ol500385a

S-aroylthiooximes: A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics

Jeffrey C. Foster, Chadwick R. Powell, Scott C. Radzinski, John B. Matson

Research output: Contribution to journal › Article › peer-review

110 Scopus citations

Abstract

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 (p = 1.05), demonstrating a significant sensitivity to electronic effects.

Original language	English
Pages (from-to)	1558-1561
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	6
DOIs	https://doi.org/10.1021/ol500385a
State	Published - Mar 21 2014
Externally published	Yes

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title = "S-aroylthiooximes: A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics",

abstract = "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 (p = 1.05), demonstrating a significant sensitivity to electronic effects.",

author = "Foster, {Jeffrey C.} and Powell, {Chadwick R.} and Radzinski, {Scott C.} and Matson, {John B.}",

year = "2014",

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doi = "10.1021/ol500385a",

language = "English",

volume = "16",

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journal = "Organic Letters",

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T2 - A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics

AU - Foster, Jeffrey C.

AU - Powell, Chadwick R.

AU - Radzinski, Scott C.

AU - Matson, John B.

PY - 2014/3/21

Y1 - 2014/3/21

N2 - 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 (p = 1.05), demonstrating a significant sensitivity to electronic effects.

AB - 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 (p = 1.05), demonstrating a significant sensitivity to electronic effects.

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JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

S-aroylthiooximes: A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics

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