25740-80-1Relevant academic research and scientific papers
Hydrolytic Decomposition of S-Aroylthiooximes: Effect of pH and N-Arylidene Substitution on Reaction Rate
Kaur, Kuljeet,Qian, Yun,Gandour, Richard D.,Matson, John B.
, p. 13363 - 13369 (2018)
The hydrolytic decomposition of four peptides containing S-aroylthiooximes (SATOs) with variable N-arylidene substituents was investigated in 10 aqueous buffer solutions at pH values ranging from 6.0 to 10.9. UV-vis spectroscopy was employed to study the reaction kinetics, which revealed V-shaped pH-rate profiles for all peptides with a minimum near pH 8, suggesting a change from an acid-catalyzed to a base-activated reaction. Hammett plots showed positive ρ values above pH 8 and negative ρ values below pH 8, providing further evidence for a mechanism change. Based on these data, along with mass spectral evidence, we propose specific acid catalysis under mildly acidic and neutral conditions and multiple base-promoted decomposition reactions under mildly basic conditions.
S-aroylthiooximes: A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics
Foster, Jeffrey C.,Powell, Chadwick R.,Radzinski, Scott C.,Matson, John B.
, p. 1558 - 1561 (2014/04/17)
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.
The Synthesis of Substituted thio>acetic Acids
Woulfe, Steven R.,Miller, Marvin J.
, p. 3133 - 3139 (2007/10/02)
The synthesis of substituted thio>acetic acids (6, thiamazins) is described.Various substituted 3(S)-(acylamino)-2-azetidinones were sulfenylated with tert-butyl (phtalimidothio)acetate.Deprotection of the tert-butyl ester with trifluoroacetic acid provided the title compounds.In sharp contrast to their oxygen analogues (oxamazins), the thiamazins were devoid of biological activity.
