1310382-67-2

Upstream product

• 170456-80-1 3-iodo-1-tosyl-1-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 890120-49-7 3-methoxy-4[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-furan-2,5-dicarboxylic acid dimethyl ester 
• 890120-47-5 3-(1H-indol-3-yl)-4-methoxy-furan-2,5-dicarboxylic acid dimethyl ester 
• 1310382-61-6 5-[7-(5-acetoxy-pentyl)-1H-indole-3-carbonyl]-4-methoxy-3[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-furan-2-carboxylic acid methyl ester 
• 915377-48-9 7-(5-acetoxypentyl)indole 

Relevant academic research and scientific papers

Regioselective synthesis of 3-(1H-indol-3-yl)-5-(1H-indole-3-carbonyl)-4- hydroxyfuroic acids: Route to hydroxyfuroic acid-based insulin receptor activators

A new class of insulin receptor activator with a hydroxyfuroic acid in place of a hydroxyquinone moiety is reported. The synthesis of 3-(1H-indol-3-yl)-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids (26-30) requires seven major steps. Key elements in the syntheses include (1) sequential preparation of two 4-(N-protected indole)-3-methoxy-furoic 2,5-dicarboxylic esters (4 and 6); (2) regioselective conversion of the furoic diacid 8 into its C-5 methyl ester 10 with methyl chloroformate; and (3) acylation of 10 by a 7-substituted indole under a mild condition. This study demonstrates a feasible route of synthesizing insulin receptor activators with a hydroxyfuroic acid scaffold. Among those hydroxyfuroic acid compounds, compound 28 demonstrates insulin receptor activation potential comparable to Merck's compound 2 with a dihydroxybenzoquinone scaffold.