220034-67-3

Upstream product

• 220034-64-0 7-(3,5-dibromo-4-hydroxyphenethylamino)-1-tosyl-3,4-dihydropyrrolo[4,3,2-de]quinolin-8(1H)-one 
• 220034-60-6 (E)-4-(2-Benzyloxy-6-iodo-3-methoxy-phenylamino)-but-2-enenitrile 
• 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 
• 121-33-5 vanillin 
• 73414-58-1 2-(3,5-dibromo-4-hydroxyphenyl)ethan-1-amine hydrobromide 
• 153718-76-4 7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one 
• 2698-69-3 4-formyl-2-methoxy-3-nitrophenyl acetate 
• 31165-12-5 3,4-dimethoxy-2,β-dinitrostyrene 
• 55149-84-3 2-nitroveratraldehyde 
• 31165-13-6 6,7-dimethoxy-1H-indole 

Downstream Products

• 105372-81-4 discorhabdin C 

Relevant academic research and scientific papers

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.

A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D

The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the α position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.