590385-69-6

Basic information

• Product Name: 5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one
• Synonyms: 5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one
• CAS NO: 590385-69-6
• Molecular Weight: 682.71
• Mol File: 590385-69-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one(590385-69-6)
• EPA Substance Registry System: 5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one(590385-69-6)

Safety Data

• Hazardous Substances Data: 590385-69-6(Hazardous Substances Data)

Upstream product

• 234757-43-8 Ethyl 6,7-dimethoxyindole-3-glyoxylate 
• 203307-89-5 3-(2-Azidoethyl)-6,7-dimethoxyindole 
• 153718-70-8 3-(2-Azidoethyl)-6,7-dimethoxy-1-<(4-methylphenyl)sulfonyl>indole 
• 153718-67-3 3-(2-hydroxyethyl)-6,7-dimethoxyindole 
• 98-59-9 p-toluenesulfonyl chloride 
• 153718-76-4 7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one 
• 425630-02-0 [2-[3-bromo-4-(tertbutyldimethylsilyloxy)phenyl]-1-(tert-butyldimethylsilyloxymethyl)ethyl]tritylamine 
• 121-33-5 vanillin 
• 2698-69-3 4-formyl-2-methoxy-3-nitrophenyl acetate 
• 55149-84-3 2-nitroveratraldehyde 
• 31165-13-6 6,7-dimethoxy-1H-indole 
• 425620-72-0 7-[2-(3-bromo-4-hydroxyphenyl)-1-(tert-butyldimethylsilyloxymethyl)-ethylamino]-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one 
• 425618-88-8 [2-[3-bromo-4-hydroxyphenyl]-1-(tert-butyldimethylsilyloxymethyl)ethyl]tritylamine 
• 425604-48-4 3-(3-bromo-4-hydroxyphenyl)-2-(tritylamino)propionic acid methyl ester 

Downstream Products

• 591209-31-3 C₂₅H₂₀BrN₃O₄S₂ 
• 1181080-56-7 C₂₆H₂₂BrN₃O₅S 
• 1315476-18-6 C₃₃H₂₆BrN₃O₆S 
• 1315476-19-7 C₂₆H₂₁BrN₆O₄S 
• 613223-61-3 (+)-5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-methoxy-10-spiro-4'-(2'-bromo)cyclohexa-2',5'-dien-1'-one 
• 590385-73-2 (+)-5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-triazaacephenanthrylen-6-one-8-(hydroxymethyl)-10-spiro-4'-(2'-bromo)cyclohexa-2',5'-dien-1'-one 

Relevant articles and documents

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.

The first total synthesis of discorhabdin A

The first stereoselective total synthesis of a potent antitumor alkaloid, discorhabdin A (1), which is a unique sulfur-containing pyrroloiminoquinone alkaloid, is described. The key step in the stereocontrolled total synthesis of 1 involves both a diaster