Preparation of 2-amino-4 (3H)-oxopyrimido [5, 4-b][1, 4] thiazines (5-thiapterins) and their evaluation as cofactors for phenylalanine hydroxylase

…, RA Lazarus, SJ Benkovic

文献索引：Henrie, Robert N.; Lazarus, Robert A.; Benkovic, Stephen J. Journal of Medicinal Chemistry, 1983 , vol. 26, # 4 p. 559 - 563

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被引用次数: 11

摘要

Reaction of diethyl chloromalonate with 8-mercapto amines, 9, gave 1, 4-thiazin-3-ones, 10, which were alkylated exclusively at the lactam oxygen with triethyloxonium tetrafluoroborate and subsequently condensed with guanidine to give the first reported 5-thiapterins, 8. Oxidation of 8 with rn-chloroperoxybenzoic acid gave the S-oxides, 12. Both 8 and 12 were found to be good inhibitors of rat liver phenylalanine hydroxylase competitive with 6- ...