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

115 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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@article{3776b548567647949f1823d43d07ac12,

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",

month = mar,

day = "21",

doi = "10.1021/ol500385a",

language = "English",

volume = "16",

pages = "1558--1561",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - S-aroylthiooximes

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.

UR - https://www.scopus.com/pages/publications/84896961530

U2 - 10.1021/ol500385a

DO - 10.1021/ol500385a

M3 - Article

C2 - 24575729

AN - SCOPUS:84896961530

SN - 1523-7060

VL - 16

SP - 1558

EP - 1561

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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