Synthesis of heterocyclic N-(尾-d-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase

详细信息	查看全文 | 推荐本文 |

• 作者：Bá ; lint Kó ; nya^a ; Tibor Docsa^b ; Pá ; l Gergely^b ; ^c ; Lá ; szló ; Somsá ; k^a ; ^{somsak@tigris.unideb.hu}
• 关键词：Azide&ndash ; alkyne cycloaddition ; Nitrile-oxide&ndash ; alkyne cycloaddition ; 1 ; 2 ; 3-Triazole-4-carboxamide ; Isoxazole-5-carboxamide ; N-(尾-d-Glucopyranosyl)carboxamide ; Glycogen phosphorylase
• 刊名：Carbohydrate Research
• 出版年：2012
• 期刊代码：15_00086215
• 类别：ch
• 出版时间：1 April, 2012
• 卷：351
• 期：Complete
• 页码：56-63
• 文件大小：637 K

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).