Synthesis and properties of the sulfonyl analogues of 4 (5) -aminoimidazole-5 (4) -carboxamide, 4 (5) - (formylamino) imidazole-5 (4) -carboxamide, guanine, and xanthine
Huang, B.S.; Chello, P.L.; Yip, L.; Parham, J.C.
Journal of Medicinal Chemistry 23(5): 575-577
ISSN/ISBN: 0022-2623 PMID: 6892931 DOI: 10.1021/jm00179a021
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.