@Article{IPB-1851, author = {Czifrák, K. and Hadady, Z. and Docsa, T. and Gergely, P. and Schmidt, J. and Wessjohann, L. and Somsák, L.}, title = {{Synthesis of N-(β-D-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase}}, year = {2006}, pages = {947-956}, journal = {Carbohyd. Res.}, doi = {10.1016/j.carres.2006.03.002}, volume = {341}, abstract = {O-Peracetylated N-(β-d-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides, or monoesters to give the corresponding N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplén protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-β-d-glucopyranosyl-carbamoyl)propanoic acid (7) with Ki \= 20 μM.} }