Oxidation of Uric Acid. 4. Synthesis, Structure, and Diabetogenic Action of 5-Imino-2,4,6(1H,3H,5H)-pyrimidinetrione Salts and Their Alloxan-Like Covalent Adducts

Article abstract of DOI:10.1021/jm00360a014

Three synthetic routes to salts of 5-amino-5-hydroxy-2,4,6(1H,3H,5H)-pyrimidinetrione (10) are described.The key reactions involved acid-catalyzed cleavage of 5-amino-5-ureido-2,4,6(1H,3H,5H)-pyrimidinetrione (7), conversion of uramil (8) to dehydrouramil (9) and subsequent hydration, and the condensation of alloxan (5) with ammonium salts.The carbinol ammonium salt structure 10a was unambiguously established by X-ray crystallography.New alloxan-like compounds 7, 9, and 10 were evaluated for diabetogenic activity in rats.Compound 7 was inactive, whereas compounds 9 and 10 showed the highest activity comparable to that of streptozotocin (12).