699-10-5Relevant articles and documents
The S2 oxygen atoms are essential for the pronounced fungitoxicity of the sulfur-rich natural product, dysoxysulfone
Bewick, Sharon A.,Duffy, Stephen,Fletcher, Stephen P.,Langler, Richard F.,Morrison, Heather G.,O'Brien, Erin M.,Ross, Charles,Stephenson, Vanessa C.
, p. 218 - 223 (2005)
Synthesis and antifungal testing of 2,4,5,7,9-pentathiadecane 9,9-dioxide has established that the absence of oxygen atoms on S2 significantly attenuates fungitoxicity in accord with our earlier proposal. Attempts to convert that compound into dysoxysulfone led to the discovery of a novel oxidative conversion of unsymmetrical γ-sulfonyl disulfides into the corresponding symmetrical γ-sulfonyl disulfides. CSIRO 2005.
PdCl2/DMSO-Catalyzed Thiol-Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
Guo, Jimin,Zha, Jianjian,Zhang, Tao,Ding, Chang-Hua,Tan, Qitao,Xu, Bin
supporting information, p. 3167 - 3172 (2021/05/05)
Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals. Disulfide-containing organic dyes have also been prepared. This transformation could be extended to thiol-diselenide or thiol-ditelluride exchange affording RS-SeR′ or RS-TeR′.
An Esterase-Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species
Zheng, Yueqin,Yu, Bingchen,Li, Zhen,Yuan, Zhengnan,Organ, Chelsea L.,Trivedi, Rishi K.,Wang, Siming,Lefer, David J.,Wang, Binghe
supporting information, p. 11749 - 11753 (2017/09/20)
A strategy to deliver a well-defined persulfide species in a biological medium is described. Under near physiological conditions, the persulfide prodrug can be activated by an esterase to generate a “hydroxymethyl persulfide” intermediate, which rapidly collapses to form a defined persulfide. Such persulfide prodrugs can be used either as chemical tools to study persulfide chemistry and biology or for future development as H2S-based therapeutic reagents. Using the persulfide prodrugs developed in this study, the reactivity between S-methyl methanethiosulfonate (MMTS) with persulfide was unambiguously demonstrated. Furthermore, a representative prodrug exhibited potent cardioprotective effects in a murine model of myocardial ischemia-reperfusion (MI/R) injury with a bell shape therapeutic profile.
