163193-56-4

Basic information

• Product Name: 1H-Indole-4,7-dione, 1-[(4-methylphenyl)sulfonyl]-
• CAS NO: 163193-56-4
• Molecular Formula: C15H11NO4S
• Molecular Weight: 301.323
• Mol File: 163193-56-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Indole-4,7-dione, 1-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-4,7-dione, 1-[(4-methylphenyl)sulfonyl]-(163193-56-4)
• EPA Substance Registry System: 1H-Indole-4,7-dione, 1-[(4-methylphenyl)sulfonyl]-(163193-56-4)

Safety Data

• Hazardous Substances Data: 163193-56-4(Hazardous Substances Data)

Upstream product

• 23876-39-3 4,7-dimethoxylindole 
• 4124-41-8 p-toluenesulfonylanhydride 
• 98-59-9 p-toluenesulfonyl chloride 
• 81038-34-8 1-(p-toluenesulphonyl)-4-hydroxyindole 
• 2380-94-1 1H-indol-4-ol 
• 163193-55-3 N-(p-Toluenesulfonyl)-4,7-dimethoxyindole 

Downstream Products

• 1208068-41-0 3-(4-methoxyphenyl)-1H,5H-pyrrolo[2,3-f]indole-4,8-dione 
• 1213229-98-1 5-(4-methoxyphenyl)-1-(toluene-4-sulfonyl)-1H,7H-pyrrolo[3,2-f]indole-4,8-dione 
• 1213229-82-3 7-(4-methoxyphenyl)-1-(toluene-4-sulfonyl)-1H,5H-pyrrolo[2,3-f]indole-4,8-dione 
• 1213229-96-9 3-(4-methoxyphenyl)-7-(toluene-4-sulfonyl)-2,3-dihydro-1H,7H-pyrrolo[3,2-f]indole-4,8-dione 

Relevant articles and documents

Novel β-carboline-based indole-4,7-quinone derivatives as NAD(P)H: Quinone-oxidoreductase-1 inhibitor with potent antitumor activities by inducing reactive oxygen species, apoptosis, and DNA damage

Eighteen new β-carboline-based indole-4,7-quinone derivatives (12a–i and 13a–i) were designed and synthesized, and their in vitro and in vivo antiproliferative activities were studied. Most of target compounds showed strong inhibition on three human tumor cells' proliferation. In particular, the most active compound 13g not only displayed more prominent antiproliferative activities than β-lapachone, a clinical antitumor candidate, but also exerted significant NAD(P)H: quinone-oxidoreductase-1 (NQO1) inhibitory activity and NQO1-dependent cytotoxicity in HT29 cells. Furthermore, 13g dose-dependently induced high ROS levels in HT29 cells, and selectively inhibited cancer cell but not non-tumor colon cell proliferation in vitro. Importantly, 13g promoted HT29 cell apoptosis and DNA damage by regulating relative apoptotic proteins and H2AX expression. Finally, 13g displayed significant growth inhibition of HT29 human colorectal adenocarcinoma xenograft in mice without overt toxicity.

The synthetic and biological studies of discorhabdins and related compounds

Various analogues of the marine alkaloids, discorhabdins, have been synthesized. The strategy contains spirocyclization with phenyliodine(iii) bis(trifluoroacetate) (PIFA), oxidative fragmentation of the β-amino alcohols with the hypervalent iodine reagent C6F 5I(OCOCF3)2, the detosylation and dehydrogenation reaction of the pyrroloiminoquinone unit in the presence of a catalytic amount of NaN3 and the bridged ether synthesis with HBr-AcOH as the key reactions. All the synthesized compounds were evaluated by in vitro MTT assay for cytotoxic activity against the human colon cancer cell line HCT-116. Furthermore, the discorhabdin A oxa analogues were also evaluated against four kinds of tumor model cells, a human colon cancer cell line (WiDr), a human prostate cancer cell line (DU-145) and murine leukemia cell lines (P388 and L1210). For the identification of the target, discorhabdin A and the discorhabdin A oxa analogue were evaluated by an HCC panel assay. In the test, discorhabdins could have a novel mode of action with the tumor cells. The Royal Society of Chemistry 2011.

Regioselective amination of indole-4,7-quinones

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