68055-31-2Relevant academic research and scientific papers
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.
Steric and Electronic Effects in the Synthesis and Regioselective Hydrolysis of Unsymmetrical Imides
Shang, Jing,Pourvali, Aysa,Cochrane, James R.,Hutton, Craig A.
, p. 1854 - 1858 (2015/12/26)
The AgI-promoted coupling reaction of thioamides and carboxylic acids is shown to be a useful method for the generation of unsymmetrical imides. The reaction proceeds efficiently with unhindered and electron-rich or neutral coupling partners, but not with hindered thioamides (such as thiopivalamides) or electron deficient thioamides (such as trifluorothioacetamides). Intriguingly, thioformamides are also ineffective coupling partners, despite having minimal steric or electronic influence. Hindered carboxylic acid coupling partners (such as pivalic acid) are tolerated, but electron deficient acids, such as trifluoroacetic acid, are ineffective coupling partners. Furthermore, an interplay of both steric and electronic effects is observed in the subsequent hydrolysis of unsymmetrical imides. Imides with a dimethoxybenzoyl group give high regioselectivity upon hydrolysis, favouring cleavage of the distal acyl group. Imides with a p-nitrobenzoyl or pivaloyl group give reversed selectivity, favouring cleavage of the proximal acyl group.
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.
Direct thionation and selenation of amides using elemental sulfur and selenium and hydrochlorosilanes in the presence of amines
Shibahara, Fumitoshi,Sugiura, Rie,Murai, Toshiaki
supporting information; experimental part, p. 3064 - 3067 (2009/12/05)
Reactions of amides with elemental sulfur in the presence of hydrochlorosilanes and amines give the corresponding thioamides in good to high yields. The process takes place via reduction of elemental sulfur by the hydrochlorosilane in the presence of a suitable amine. The methodology can be applied to the selenation of amides by using elemental selenium. Thlonation and selenation of an acetyl-protected sialic acid derivative are found to take place selectively at the amide group.
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.
