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 (ρ = 1.05), demonstrating a significant sensitivity to electronic effects.
authors.affiliation: Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
authors.forename: Jeffrey C
authors.initials: JC
authors.lastname: Foster
authors.forename: Chadwick R
authors.initials: CR
authors.lastname: Powell
authors.forename: Scott C
authors.initials: SC
authors.lastname: Radzinski
authors.forename: John B
authors.initials: JB
authors.lastname: Matson
mesh_terms: D003545:Cysteine / Q000737:chemistry; D006207:Half-Life; D006862:Hydrogen Sulfide / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D010091:Oximes; D013457:Sulfur Compounds; D003545:Cysteine; D006862:Hydrogen Sulfide