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Evangelia D. Chrysina Éva Bokor Kyra-Melinda Alexacou Maria-Despoina Charavgi George N. Oikonomakos Spyros E. Zographos Demetres D. Leonidas Nikos G. Oikonomakos László Somsák 《Tetrahedron: Asymmetry》2009,20(6-8):733-740
Per-O-acetylated β-d-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-β-d-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(β-d-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide–alkyne cycloadditions. Deprotection of these products by the Zemplén method furnished β-d-Glcp-NHCO-R derivatives as well as 1-(β-d-Glcp)-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme–inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. 相似文献
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