68055-31-2Relevant articles and documents
Iminothioethers as Hydrogen Sulfide Donors: From the Gasotransmitter Release to the Vascular Effects
Barresi, Elisabetta,Nesi, Giulia,Citi, Valentina,Piragine, Eugenia,Piano, Ilaria,Taliani, Sabrina,Da Settimo, Federico,Rapposelli, Simona,Testai, Lara,Breschi, Maria Cristina,Gargini, Claudia,Calderone, Vincenzo,Martelli, Alma
, p. 7512 - 7523 (2017/09/23)
The gasotransmitter hydrogen sulfide (H2S) is an important tuner of the cardiovascular homeostasis, and its deficiency is etiologically associated with a number of cardiovascular diseases. Therefore, the research of original moieties able to release H2S represents a timely issue for drug discovery. In this work, we developed a collection of iminothioethers (ITEs), exhibiting H2S-releasing properties and producing vasorelaxing effects on rat aortic rings. Derivatives 4 and 11, selected as representative of slow and fast rate H2S donors, respectively, produced a complete recovery of the basal coronary flow, reverting the AngII-induced effects in isolated rat hearts. In addition, studies on human aortic smooth muscle cells (HASMCs) demonstrated membrane hyperpolarizing effects, well related to the intracellular generation of H2S. Taken together, the results obtained support ITEs 4 and 11 as new pharmacological tools, as well as effective and innovative H2S donors for cardiovascular drug discovery.
A multipathway coupled domino strategy: I2-mediated oxidative thionation for direct synthesis of thiobenzamides from miscellaneous substrates
Li, Hong-Zheng,Xue, Wei-Jian,Yin, Guo-Dong,Wu, An-Xin
supporting information, p. 5843 - 5846 (2015/11/02)
An efficient iodine-mediated multipathway coupled domino reaction has been developed for the synthesis of thiobenzamides from benzylamines, benzylamines/aldehydes, and N-alkyl benzylamines under the same reaction conditions. This approach combines two consecutive domino processes in one pot using iodine as the oxidant.
Aminolysis of O-aryl thionobenzoates: Amine basicity combines with modulation of the nature of substituents in the leaving group and thionobenzoate moiety to control the reaction mechanism
Um, Ik-Hwan,Hwang, So-Jeong,Yoon, Sora,Jeon, Sang-Eun,Bae, Sun-Kun
, p. 7671 - 7677 (2008/12/22)
(Chemical Equation Presented) A kinetic study is reported for aminolysis of O-Y-substituted phenyl thionobenzoates (la-f) and O-4-nitrophenyl X-substituted thionobenzoates (2a-f) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1°C. The reaction proceeds through one or two intermediates (i.e., a zwitterionic tetrahedral intermediate T± and its deprotonated form T-) depending on the basicity difference between the nucleophile and nucleofuge, that is, the reaction proceeds through T ± when the leaving aryloxide is less basic than the attacking amine, but through T± and T- when the leaving group is more basic than the amine. However, the reaction mechanism is not influenced by the electronic nature of the substituent X in the nonleaving group. The Hammett plot for the reactions of 2a-f with benzylamine is consisted of two intersecting straight lines, which might be interpreted as a change in the rate-determining step (RDS). However, the Yukawa-Tsuno plot for the same reactions exhibits an excellent linear correlation, indicating that the nonlinear Hammett plot is not due to a change in the RDS but caused by stabilization of the ground-state of the substrate through resonance interaction between the electron-donating substituent X and the thionocarbonyl moiety.
