摘要
In a DCC-mediated coupling 2,3,4,6-tetra-O-acetyl-尾-d-glucopyranosylamine and propiolic acid gave N-propynoyl-2,3,4,6-tetra-O-acetyl-尾-d-glucopyranosylamine which was transformed by 1,3-dipolar cycloadditions with aromatic azides and nitrile-oxides to the corresponding O-peracetylated N-(尾-d-glucopyranosyl)-1-substituted-1,2,3-triazole-4-carboxamides and N-(尾-d-glucopyranosyl)-3-substituted-isoxazole-5-carboxamides, respectively. These compounds were O-deacetylated by Zempl茅n鈥檚 protocol to be tested as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitors of the two series were N-(尾-d-glucopyranosyl)-1-(3,5-dimethyl-phenyl)-1,2,3-triazole-4-carboxamide (Kb>ib> = 34 渭M) and N-(尾-d-glucopyranosyl)-3-(indol-2-yl)-isoxazole-5-carboxamide (Kb>ib> = 164 渭M).