10269-25-7

Basic information

• Product Name: 3H-1,2-Dithiole-3-thione,4-methyl-5-phenyl-
• Synonyms: 1,2-Dithiole-3-thione,4-methyl-5-phenyl- (6CI); 37528RP; 4-Methyl-5-phenyl-1,2-dithiole-3-thione;4-Methyl-5-phenyl-3H-1,2-dithiole-3-thione; CJ 11842; RP 37528
• CAS NO: 10269-25-7
• Molecular Formula: C10H8 S3
• Molecular Weight: 224.372
• Mol File: 10269-25-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3H-1,2-Dithiole-3-thione,4-methyl-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-1,2-Dithiole-3-thione,4-methyl-5-phenyl-(10269-25-7)
• EPA Substance Registry System: 3H-1,2-Dithiole-3-thione,4-methyl-5-phenyl-(10269-25-7)

Safety Data

• Hazardous Substances Data: 10269-25-7(Hazardous Substances Data)

Upstream product

• 1199-77-5 α-methylcinnamic acid 
• 65-85-0 benzoic acid 
• 93-89-0 benzoic acid ethyl ester 
• 56764-07-9 methylphenylcyclopropenethione 
• 100-86-7 2-Methyl-1-phenyl-2-propanol 
• 93-55-0 1-phenyl-propan-1-one 
• 75-15-0 carbon disulfide 
• 80158-76-5 bis-(1-methyl-2-oxo-2-phenyl-ethylidene)-[1,3]dithietane 
• 80608-61-3 4,4,'-Dimethyl-5,5'-diphenyl-3,3'-bi(3H-1,2-dithiolyliden) 
• 611-70-1 phenyl isopropyl ketone 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 768-49-0 (2-methyl-1-propenyl)-benzene 

Downstream Products

• 59704-68-6 4-methyl-3-methylsulfanyl-5-phenyl-[1,2]dithiolylium; iodide 
• 16074-76-3 3,6-Dimethyl-2,5-diphenylthieno<3,2-b>thiophen 
• 73659-50-4 4-methyl-5-phenyl-1,2-dithiolen-3-one 
• 64931-55-1 cis-4,5-tetramethylene-2-(α-thiobenzoylethylidene)-1,3-dithiolane 
• 64931-54-0 cis-4,5-(1,8-naphtylene)-2-(α-thiobenzoylethylidene)-1,3-dithiolane 
• 69812-76-6 4',5-dimethyl-5'-phenyl-5-cyano-1,3-dithiane-4-spiro-3'-(1',2'-dithiolene) 
• 69812-75-5 4-methyl-5-phenyl-3-(α-cyanoethylidene)-1,2-dithiolene 
• 80067-31-8 methyl-4 phenyl-5 dithiole-1,2 ylidene-3 malononitrile 
• 35093-32-4 2,3,5,6-tetraphenylthieno[3,2-b]thiophene 
• 13232-76-3 4,5-diphenyl-[1,2]dithiole-3-thione 
• 17835-44-8 4,5-diphenyl-3H-1,2-dithiol-3-one 
• 81385-53-7 3-Methyl-2,5,6-triphenylthieno<3,2-b>furan 
• 81385-54-8 2-[1-Methyl-2-phenyl-2-thioxo-eth-(Z)-ylidene]-5,6-diphenyl-[1,3]dithiin-4-one 
• 74816-71-0 4,5-dimethoxycarbonyl-2-(α-thiobenzoylethylidene)-1,3-dithiole 

Relevant articles and documents

Abrogation of hyperosmotic impairment of insulin signaling by a novel class of 1,2-dithiole-3-thiones through the inhibition of S6K1 activation

A previous study from this laboratory showed that oltipraz and synthetic dithiolethiones prevent tumor necrosis factor-α-induced hepatic insulin resistance via AMP-activated protein kinase-dependent p70S6 kinase (S6K) 1 inhibitory pathway. This study investigated whether oltipraz and a novel class of 1,2-dithiole-3-thiones were capable of preventing insulin resistance induced by hyperosmotic stress, thereby enhancing insulin-dependent signals, and, if so, whether the restoration of insulin signal was mediated with the inhibition of S6K1 activity stimulated by hyperosmotic stress. In HepG2 cells, oltipraz treatment inhibited insulin receptor substrate (IRS) 1 serine phosphorylation, a marker of insulin resistance, induced by sorbitol-, mannitol-, or sodium chloride-induced hyperosmotic stress. Consequently, this allowed cells to restore insulin signals, which was evidenced by decrease in the ratio of serine to tyrosine phosphorylations of IRS1 and increase in the phosphorylations of Akt and glycogen synthase kinase (GSK) 3β. Hyperosmotic stress markedly activated S6K1; S6K1 activation was completely abolished by oltipraz pretreatment. An experiment using dominant-negative S6K1 supports the essential role of S6K1 in the hyperosmolarity-stimulated phosphorylation of IRS1. Transfection of constitutive active mutant S6K1 eliminated the protective effect of oltipraz on GSK3β phosphorylation, indicating that oltipraz restores insulin signaling by inhibiting S6K1 activation. A variety of synthetic 1,2-dithiole-3-thione derivatives also inhibited S6K1 activity and insulin resistance induced by hyperosmotic stress in HepG2 cells. The results of this study demonstrate that a novel class of 1,2-dithiole-3-thiones improve insulin sensitivity under the condition of hyperosmotic stress, which results from the inhibition of S6K1 activation. Copyright

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Dianions of 3-oxodithioic acids: Preparation and conversion to 3H-1,2-dithiole-3-thiones

Reaction of ketones with CS2 and 2 equivalents of KH in THF-N,N'-dimethylpropyleneurea solution produces the dianions of 3-oxodithioic acids. These dianions are converted in good yield to 3H-1,2-dithiole-3-thiones by the sequential action of hexamethyldisilathiane and an oxidizing agent such as hexachloroethane. (C) 2000 Elsevier Science Ltd.