55055-84-0

Upstream product

• 28519-50-8 potassium thiotosylate 
• 459-46-1 4-Fluorobenzyl bromide 

Downstream Products

• 1372559-23-3 (Z)-1-(p-fluorophenyl)-8-(p-methoxyphenyl)-2,3,7-trithiaoct-4-ene 
• 1372559-02-8 (E)-1-(p-fluorophenyl)-8-(p-methoxyphenyl)-2,3,7-trithiaoct-4-ene 

Relevant academic research and scientific papers

Design and synthesis of garlic-related unsymmetrical thiosulfonates as potential Alzheimer's disease therapeutics: In vitro and in silico study

Garlic contains a wide range of organosulfur compounds, which exhibit a broad spectrum of biological activities. Amongst the sulfur-containing compounds in garlic, the thiosulfonates are considerably popular in various fields. In light of this, we decided

The cytotoxicity of garlic-related disulphides and thiosulfonates in WHCO1 oesophageal cancer cells is dependent on S-thiolation and not production of ROS

Background Garlic has been used for centuries in folk medicine for its health promoting and cancer preventative properties. The bioactive principles in crushed garlic are allyl sulphur compounds which are proposed to chemically react through (i) protein S-thiolation and (ii) production of ROS. Methods A collection of R-propyl disulphide and R-thiosulfonate compounds were synthesised to probe the importance of thiolysis and ROS generation in the cytotoxicity of garlic-related compounds in WHCO1 oesophageal cancer cells. Results A significant correlation (R2 = 0.78, Fcrit (7,1) α = 0.005) was found between the cytotoxicity IC50 and the leaving group pKa of the R-propyl disulphides and thiosulfonates, supporting a mechanism that relies on the thermodynamics of a mixed disulphide exchange reaction. Disulphide (1) and thiosulfonate (11) were further evaluated mechanistically and found to induce G2/M cell-cycle arrest and apoptosis, inhibit cell proliferation, and generate ROS. When the ROS produced by 1 and 11 were quenched with Trolox, ascorbic acid or N-acetyl cysteine (NAC), only NAC was found to counter the cytotoxicity of both compounds. However, NAC was found to chemically react with 11 through mixed disulphide formation, providing an explanation for this apparent inhibitory result. Conclusion Cellular S-thiolation by garlic related disulphides appears to be the cause of cytotoxicity in WHCO1 cells. Generation of ROS appears to only play a secondary role. General significance Our findings do not support ROS production causing the cytotoxicity of garlic-related disulphides in WHCO1 cells. Importantly, it was found that the popular ROS inhibitor NAC interferes with the assay.

Structure-activity studies on the anti-proliferation activity of ajoene analogues in WHCO1 oesophageal cancer cells

The organosulfur compound ajoene derived from the rearrangement of allicin found in crushed garlic can inhibit the proliferation of tumour cells by inducing G2/M cell cycle arrest and apoptosis. We report on the application of a concise four-step synthesis (Hunter et al., 2008 [1]) that allows access to ajoene analogues with the end allyl groups substituted. A library of twelve such derivatives tested for their anti-proliferation activity against WHCO1 oesophageal cancer cells has identified a derivative containing p-methoxybenzyl (PMB)-substituted end groups that is twelve times more active than Z-ajoene, with an IC50 of 2.1 μM (Kaschula et al., 2011 [2]). Structure-activity studies involving modification of the sulfoxide and vinyl disulfide groups of this lead have revealed that the disulfide is the ajoene pharmacophore responsible for inhibiting WHCO1 cell growth, inducing G 2/M cell cycle arrest and apoptosis by caspase-3 activation, and that the vinyl group serves to enhance the anti-proliferation activity a further eightfold. Reaction of the lead with cysteine in refluxing THF as a model reaction for ajoene's mechanism of action based on a thiol/disulfide exchange reveals that the allylic sulfur of the vinyl disulfide is the site of thiol attack in the exchange.

2-(Sulfur-substituted)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-ones

Concerns compounds of the formula SPC1 Wherein R1 is a 1 to 6 carbon atom alkyl, benzyl, halobenzyl, lower alkylbenzyl, nitrobenzyl, alkenyl, haloalkenyl, 2-(lower alkylthio)lower alkyl or cyclohexylmethyl group, R2 is hydrogen, ammonium or alkali metal and n is an integer from 0 to 2. The compounds are prepared by reacting an alkali metal salt of 3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one with a thiolsulfonate. The compounds are useful as plant growth regulators.