97136-91-9Relevant academic research and scientific papers
Electron transfer to sulfides and disulfides: Intrinsic barriers and relationship between heterogeneous and homogeneous electron-transfer kinetics
Meneses, Ana Belen,Antonello, Sabrina,Arevalo, Maria Carmen,Gonzalez, Concepcion Carmen,Sharma, Jadab,Wallette, Andrea N.,Workentin, Mark S.,Maran, Flavio
, p. 7983 - 7995 (2008/04/01)
The electron-acceptor properties of series of related sulfides and disulfides were investigated in N,N-dimethylformamide with homogeneous (redox catalysis) and/or heterogeneous (cyclic voltammetry and convolution analysis) electrochemical techniques. The electron-transfer rate constants were determined as a function of the reaction free energy and the corresponding intrinsic barriers were determined. The dependence of relevant thermodynamic and kinetic parameters on substituents was assessed. The kinetic data were also analyzed in relation to corresponding data pertaining to reduction of diaryl disulfides. All investigated reductions take place by stepwise dissociative electron transfer (DET) which causes cleavage of the Calkyl-S or S-S bond. A generalized picture of how the intrinsic electron-transfer barrier depends on molecular features, ring substituents, and the presence of spacers between the frangible bond and aromatic groups was established. The reduction mechanism was found to undergo a progressive (and now predictable) transition between common stepwise DET and DET proceeding through formation of loose radical anions. The intrinsic barriers were compared with available results for ET to several classes of dissociative- and nondissociative-type acceptors, and this led to verification that the heterogeneous and the homogeneous data correlate as predicted by the Hush theory.
Synthesis and Biological Activity of trans-(+/-)-N-Methyl-2-(3-pirydyl)-2-tetrahydrothiopyrancarbothioamide 1-Oxide (RP 49356) and Analogues: A New Class of Potassium Channel Opener
Brown, Thomas J.,Chapman, Robert F.,Cook, David C.,Hart, Terance W.,McLay, Iain M.,et al.
, p. 3613 - 3624 (2007/10/02)
The synthesis and biological activity of trans-(+/-)-N-methyl-2-(3-pyridyl)-2-tetrahydrothiopyrancarbothioamide 1-oxide (8a, RP 49356) and analoques is reported.These compounds constitute a new structural class of K+-channel opener.The effects of changes in the pyridyl group, thioamide, and thiane ring on in vitro K+-channel opening activity are discussed.A 3-pyridyl or 3-quinolyl group, a small N-alkyl thioamide function, and a thiane oxide ring, in which the sulfoxide is in a trans relationship to thioamide, are preferred for activity.Selected compounds were tested intravenously in the normotensive anaesthetized rat for hypotensive effects, and the activities reflect their in vitro K+-channel opening activity.This led to further evaluation of compound 8a and the selection of the (-)-enantiomer 8b (RP 52891) for development as an antihypertensive and antianginal agent.
