1208-20-4Relevant articles and documents
Kice,Large
, p. 4069 (1968)
Natural product inspired allicin analogs as novel anti-cancer agents
Bhaumik, Ishani,Pal, Kunal,Debnath, Utsab,Karmakar, Parimal,Jana, Kuladip,Misra, Anup Kumar
, p. 259 - 272 (2019/02/07)
A series of novel analogs of Allicin (S-allyl prop-2-ene-1-sulfinothioate) present in garlic has been synthesized in high yield. Synthesized 23 compounds were evaluated against different breast cancer cells (MDA-MB-468 and MCF-7) and non-cancer cells (WI38). Four compounds (3f, 3h, 3m and 3u) showed significant cytotoxicity against cancer cells whereas nontoxic to the normal cells. Based on the LD50 values and selectivity index (SI), compound 3h (S-p-methoxybenzyl (p-methoxyphenyl)methanesulfinothioate) was considered as most promising anticancer agent amongst the above three compounds. Further bio-chemical studies confirmed that compound 3h promotes ROS generation, changes in mitochondrial permeability transition and induced caspase mediated DNA damage and apoptosis.
Oxidation of disulfides to thiolsulfinates with hydrogen peroxide and a cyclic seleninate ester catalyst peroxide and a cyclic seleninate ester catalyst
McNeil, Nicole M. R.,McDonnell, Ciara,Hambrook, Miranda,Back, Thomas G.
, p. 10748 - 10762 (2015/08/11)
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.
Silica-coated magnetite nanoparticles stabilized simple Mn-tetraphenylporphyrin for aqueous phase catalytic oxidations with tert-butyl hydroperoxide
Rezaeifard, Abdolreza,Farshid, Parisa,Jafarpour, Maasoumeh,Moghaddam, Gholamreza Kardan
, p. 9189 - 9196 (2014/03/21)
An economic and environmentally friendly system for efficient and selective oxidation of industrially and biologically important substrates in water using tert-butyl hydroperoxide catalyzed by a new magnetically recoverable Mn-porphyrin was developed. The easily prepared heterogeneous catalyst was characterized by powder X-ray diffraction, transmission electron microscopy, scanning electron microscopy, FT-IR and UV-vis spectroscopy. The size of the catalyst was estimated to be about 10 nm. The thermal gravimetric analysis demonstrated that the nanocatalyst was thermally stable up to almost 300 °C. The reactivity, selectivity and scope of the reaction were investigated with a variety of olefins, saturated hydrocarbons, alcohols and organosulfur compounds. The reactions proceeded smoothly in the absence of surfactants, organic co-solvents and thus take place "on water". The separation and recycling of nanocatalyst as well as isolation of water-insoluble products were simple, effective and economical in this clean oxidation method.
