Synthesis and properties of the sulfonyl analogues of 4(5)-aminoimidazole-5(4)-carboxamide, 4(5)-(formylamino)imidazole-5(4)-carboxamide, guanine, and xanthine.
Reduction of 4(5)-nitroimidazole-5(4)-sulfonamide afforded the sulfonamide analogue of 4(5)-aminoimidazole-5(4)-carboxamide (AICA). This was formylated to afford the sulfonamide analogue of formyl-AICA and was ring closed to the unsubstituted 6-sulfonyl analogue of guanine, 3-aminoimidazo[4,5-e]-1,2,4-thiadizine 1,1-dioxide. Diazotiz ation of the latter afforded the corresponding 6-sulfonyl analogue of xanthine. None of the imidazole-sulfonamides or the purine 6-sulfonyl analogues inhibited the growth of L1210 cells in culture nor were they substrates for or significant inhibitors of human hypoxanthine--guanine phosphoribosyltransferase or milk xanthine oxidase.
D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D006147:Guanine / Q000031:analogs & derivatives* / Q000494:pharmacology; D007041:Hypoxanthine Phosphoribosyltransferase / Q000037:antagonists & inhibitors; D007093:Imidazoles / Q000494:pharmacology*; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors; D014970:Xanthines / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D007093:Imidazoles; D014970:Xanthines; D000620:Aminoimidazole Carboxamide; D006147:Guanine; D014969:Xanthine Oxidase; D007041:Hypoxanthine Phosphoribosyltransferase