97379-48-1Relevant articles and documents
Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids
Cao, Hong,McNamee, Laura,Alper, Howard
, p. 3530 - 3534 (2008)
(Chemical Equation Presented) Trihexyl(tetradecyl)phosphonium hexafluorophosphate, a phosphonium salt ionic liquid (PSIL) is a particularly effective general reaction media for the Pd-catalyzed carbonylation reaction of iodoarenes and thiols to form thioesters. Recycling of the ionic liquid containing active Pd-catalyst was also demonstrated.
Decarboxylative Thiolation of Redox-Active Esters to Thioesters by Merging Photoredox and Copper Catalysis
Cao, Tianpeng,Liao, Saihu,Nie, Xingliang,Xu, Ruting,Xu, Tianxiao,Yang, Mingcheng
supporting information, p. 3692 - 3696 (2020/04/21)
Thioesters and related thiols are critically important to biological systems and also widely employed in the synthesis of pharmaceutically important molecules and polymeric materials. However, known synthetic methods often suffer from the disadvantage of
Controllable thioester-based hydrogen sulfide slow-releasing donors as cardioprotective agents
Yao, Hong,Luo, Shanshan,Liu, Junkai,Xie, Shaowen,Liu, Yanpeng,Xu, Jinyi,Zhu, Zheying,Xu, Shengtao
, p. 6193 - 6196 (2019/06/07)
Hydrogen sulfide (H2S) is an important signaling molecule with promising protective effects in many physiological and pathological processes. However, the study of H2S has been impeded by the lack of appropriate H2S donors that could mimic its slow-releasing process in vivo. Herein, we report the rational design, synthesis, and biological evaluation of a series of thioester-based H2S donors. These cysteine-activated H2S donors release H2S in a slow and controllable manner. Most of the donors comprising an allyl moiety showed significant cytoprotective effects in H9c2 cellular models of oxidative damage. The most potent donor 5e decreased the mitochondrial membrane potential (MMP) loss and lactate dehydrogenase (LDH) release in H2O2-stimulated H9c2 cells. More importantly, donor 5e exhibited a potent cardioprotective effect in an in vivo myocardial infarction (MI) mouse model by reducing myocardial infarct size and cardiomyocyte apoptosis. Taken together, our studies demonstrated that these new allyl thioesters are potential cardioprotective agents by releasing H2S.
One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
Liao, Yen-Sen,Liang, Chien-Fu
, p. 1871 - 1881 (2018/03/23)
In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.
Poly(3,4-dimethyl-5-vinylthiazolium)/DBU-catalyzed thioesterification of aldehydes with thiols
Chung, Junyong,Seo, Ue Ryung,Chun, Supill,Chung, Young Keun
, p. 318 - 321 (2016/02/05)
Poly(3,4-dimethyl-5-vinylthiazolium) was synthesized from 3,4-dimethyl-5-vinylthiazole through free radical polymerization and was examined as polymer precatalysts in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the thioesterification of aldehydes with thiols. The poly(5-vinylthiazolium)/DBU had excellent catalytic activity and could be reused 10 times without a considerable loss of activity. To S-um up: Poly(3,4-dimethyl-5-vinylthiazolium) is examined as a polymer precatalyst in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the thioesterification of aldehydes with thiols. The poly(5-vinylthiazolium)/DBU system shows excellent catalytic activity and can be reused 10 times without a considerable loss of activity.
