890120-45-3

Upstream product

• 890120-63-5 [1-(4-methoxy-benzyl)-1H-indol-3-yl]-oxo-acetic acid methyl ester 
• 7040-23-5 dimethyl diglycolate 
• 74-88-4 methyl iodide 
• 890120-43-1 3-hydroxy-4-[1-(4-methoxy-benzyl)-1H-indol-3-yl]-furan-2,5-dicarboxylic acid dimethyl ester 

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.

4-Hydroxyfuroic acid derivatives

This invention relates to treating diabetes mellitus with certain 4-hydroxyfuroic acid derivatives. These derivates are of formula (I) below. Each variable is defined in the specification.