134281-83-7

Basic information

• Product Name: 2,5-Cyclohexadiene-1,4-dione, 2-[(4-methylphenyl)sulfinyl]-, (S)-
• CAS NO: 134281-83-7
• Molecular Formula: C13H10O3S
• Molecular Weight: 246.287
• Mol File: 134281-83-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadiene-1,4-dione, 2-[(4-methylphenyl)sulfinyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadiene-1,4-dione, 2-[(4-methylphenyl)sulfinyl]-, (S)-(134281-83-7)
• EPA Substance Registry System: 2,5-Cyclohexadiene-1,4-dione, 2-[(4-methylphenyl)sulfinyl]-, (S)-(134281-83-7)

Safety Data

• Hazardous Substances Data: 134281-83-7(Hazardous Substances Data)

Upstream product

• 150-78-7 1,4-dimethoxybezene 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 134281-69-9 [S(S)]-2-p-tolylsulfinyl-1,1,4,4-tetramethoxy-2,5-cyclohexadiene 
• 134281-63-3 (S)-(-)-1,4-dimethoxy-2-(p-tolylsulfinyl)benzene 

Downstream Products

• 130-15-4 [1,4]naphthoquinone 
• 667421-14-9 (S)-3,6-dihydroxy-2-(p-tolylsulfinyl)benzonitrile 
• 162060-46-0 endo-<4aR,5S,8R,8aS,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone 
• 174060-78-7 endo-<4aR,5R,8S,8aR,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone 

Relevant articles and documents

Quinoides and VEGFR2 TKIs influence the fate of hepatocellular carcinoma and its cancer stem cells

Bioactivities of quinoides 1-5 and VEGFR2 TKIs 6-10 in hepatocellular cancer (HCC) and cancer stem cells (HCSCs) were studied. The compounds exhibited IC50 values in μM concentrations in HCC cells. Quinoide 3 was able to eradicate cancer stem cells, similar to the action of the stem cell inhibitor DAPT. However, the more cytotoxic VEFGR TKIs (IC50: 0.4-3.0 μM) including sorafenib, which is the only FDA approved drug for the treatment of HCC, enriched the hepatocellular cancer stem cell population by 2-3 fold after treatment. An aggressiveness factor (AF) was proposed to quantify the characteristics of drug candidates for their ability to eradicate the CSC subpopulation. Considering the tumour heterogeneity and marker positive cancer stem cell like subpopulation enrichment upon treatments in patients, this study emphasises the importance of the chemotherapeutic agent choice acting differentially on all the subpopulations including marker-positive CSCs.

Synthesis of Optically Active p-Tolylsulfinylquinones

The title compounds 3a-e were prepared in only two steps from 1,4-dimethoxyaromatic precursors 1a-e by sulfinylation followed by oxidation with ammonium cerium(IV) nitrate.

SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTIONS OF (S)-2-p-TOLYLSULFINYL-1,4-BENZOQUINONE

Optically pure (S)-2-p-tolylsulfinyl-1,4-benzoquinone (5) is readily obtained by deketalization of the corresponding quinone bisketal 4, synthesized by Andersen's type synthesis on 2-bromo-1,4-dimethoxybenzene (1) followed by anodic oxidation of the resulting sulfoxide.The Diels-Alder reaction of cyclopentadiene with 5 took place on C5-C6 dienophilic double bond showing high facial selectivity, which can be inverted by using different Lewis acids, and total endo selectivity.