Synthesis and xanthine oxidase inhibitory analysis of 1H-pyrrolo[3,2-c]pyridine-4,6(5H,7H)-dione (3,7-dideazaxanthine) and two of its derivatives

Abstract

The synthesis of 1H-pyrrolo[3,2-c]pyridine-4,6(5H,7H)-dione(3,7-dideazaxanthine) (1), 5-methyl-1H-pyrrolo-[3,2-c]pyridine-4,6(5H,7H)-dione(1-methyl-3,7-dideazaxanthine) (2) and 1,7-dihydropyrano[4,3-b]pyrrole-4,6-dione(1-oxa-1,3,7-trideazaxanthine) (3) was accomplished from 3-alkoxycarbonylpyrrole-2-acetates and from 3-carboxypyrrole-2-acetic acid. Compounds 1 and 2 were weak inhibitors of the noncompetitive type for xanthine oxidase while 3 showed no inhibitory properties toward this enzyme.