97031-22-6

Upstream product

• 696-63-9 4-Methoxybenzenethiol 
• 31401-23-7 p-methoxybenzenesulfinyl chloride 
• 1950-65-8 4-methoxybenzenesulfenyl chloride 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 882-33-7 diphenyldisulfane 
• 7205-64-3 1-[(1,1-dimethylethyl)thio]-4-methoxybenzene 
• 7205-74-5 1-methoxy-4-(2-methyl-propane-2-sulfinyl)-benzene 

Downstream Products

• 1153-43-1 4,4'-dimethoxyphenyl thiosulfonate 

Relevant academic research and scientific papers

Reactions of bis(p-methoxyphenyl)trisulfane and its oxides with dimethyldioxirane and (trifluoromethyl)methyldioxirane

The reactions of dimethyldioxirane and (trifluoromethyl)methyldioxirane with bis(p-methoxyphenyl)-trisulfane, its 1-oxide, its 2-oxide, and its 1,1-dioxide derivatives have been investigated. The reactions were followed by careful monitoring of the methox

Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer

Organosulfur compounds derived from Allium vegetables have long been recognized for various therapeutic effects, including anticancer activity. Allicin, one of the main biologically active components of garlic, shows promise as an anticancer agent; however, instability makes it unsuitable for clinical application. The aim of this study was to investigate the effect of stabilized allicin derivatives on human breast cancer cells in vitro. In this study, a total of 22 stabilized thiosulfinate derivatives were synthesized and screened for their in vitro antiproliferative activities against drug-sensitive (MCF-7) and multidrug-resistant (MCF-7/Dx) human adenocarcinoma breast cancer cells. Assays for cell death, apoptosis, cell cycle progression and mitochondrial bioenergetic function were performed. Seven compounds (4b, 7b, 8b, 13b, 14b, 15b and 18b) showed greater antiproliferative activity against MCF-7/Dx cells than allicin. These compounds were also selective towards multidrug-resistant (MDR) cells, a consequence attributed to collateral sensitivity. Among them, 13b exhibited the greatest anticancer activity in both MCF-7/Dx and MCF-7 cells, with IC50 values of 18.54±0.24 and 46.50±1.98 μmol/L, respectively. 13b altered cellular morphology and arrested the cell cycle at the G2/M phase. Additionally, 13b dose-dependently induced apoptosis, and inhibited cellular mitochondrial respiration in cells at rest and under stress. MDR presents a significant obstacle to the successful treatment of cancer clinically. These results demonstrate that thiosulfinate derivatives have potential as novel anticancer agents and may offer new therapeutic strategies for the treatment of chemoresistant cancers.

Oxidation of disulfides to thiolsulfinates with hydrogen peroxide and a cyclic seleninate ester catalyst peroxide and a cyclic seleninate ester catalyst

Cyclic seleninate esters function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. They catalyze the reduction of harmful peroxides with thiols, which are converted to disulfides in the process. The possibility that the seleninate esters could also catalyze the further oxidation of disulfides to thiolsulfinates and other overoxidation products under these conditions was investigated. This has ramifications in potential medicinal applications of seleninate esters because of the possibility of catalyzing the unwanted oxidation of disulfide-containing spectator peptides and proteins. A variety of aryl and alkyl disulfides underwent facile oxidation with hydrogen peroxide in the presence of catalytic benzo-1,2-oxaselenolane Se-oxide affording the corresponding thiolsulfinates as the principal products. Unsymmetrical disulfides typically afforded mixtures of regioisomers. Lipoic acid and N,N′-dibenzoylcystine dimethyl ester were oxidized readily under similar conditions. Although isolated yields of the product thiolsulfinates were generally modest, these experiments demonstrate that the method nevertheless has preparative value because of its mild conditions. The results also confirm the possibility that cyclic seleninate esters could catalyze the further undesired oxidation of disulfides in vivo.

Structural effects on the C-S bond cleavage in aryl tert -butyl sulfoxide radical cations

The oxidation of a series of aryl tert-butyl sulfoxides (4-X-C 6H4SOC(CH3)3: 1, X = OCH 3; 2, X = CH3; 3, X = H; 4, X = Br) photosensitized by 3-cyano-N-methylquinolinium perchlorate (3-CN-NMQ+) has been investigated by steady-state irradiation and nanosecond laser flash photolysis (LFP) under nitrogen in MeCN. Products deriving from the C-S bond cleavage in the radical cations 1+?-4+? have been observed in the steady-state photolysis experiments. By laser irradiation, the formation of 3-CN-NMQ? (λmax = 390 nm) and 1 +?-4+? (λmax = 500-620 nm) was observed. A first-order decay of the sulfoxide radical cations, attributable to C-S bond cleavage, was observed with fragmentation rate constants (k f) that decrease by increasing the electron donating power of the arylsulfinyl substituent from 1.8 × 106 s-1 (4 +?) to 2.3 × 105 s-1 (1 +?). DFT calculations showed that a significant fraction of the charge is delocalized in the tert-butyl group of the radical cations, thus explaining the small substituent effect on the C-S bond cleavage rate constants. Via application of the Marcus equation to the kinetic data, a very large value for the reorganization energy (λ = 62 kcal mol-1) has been calculated for the C-S bond scission reaction in 1+?-4 +?.

S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/ trifluoromethanesulfonic anhydride: A convenient system for the generation of glycosyl triflates from thioglycosides

(Matrix presented) The combination of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT, 1) and trifluoromethanesulfonic anhydride forms a powerful, metal-free, thiophile which readily activates thioglycosides, via glycosyl triflates, at -60°C in dichloromet

CO-OXIDATIONS OF SQUALENE WITH DISULFIDES AND THIOSULFINATES

Comparison of the activities of alkyl and aryl disulfides in inhibiting the autoxidation of squalene show the greater efficiency of the alkyl derivatives.The effect of electron donating substituents in aryl derivatives, promoting efficiency in the order CH3O > CH3 > H, is reversed in the thiosulfinates when added directly, although they are considered to be inhibitors formed in situ from the disulfides.The anomaly is discussed in terms of rates of oxidation and stabilities of the oxidation products and leads to the concept of thiosulfinate/disulfide mixture as a more efficient antioxidant.Key words: Antioxidants; disulfides; thiosulfinates; sulfinyl group; stability.