Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

Synthesis and biological evaluation of glucoconjugates of oleanolic acid, linked by either a triazole moiety or an ester function, as novel inhibitors of glycogen phosphorylase have been described. Several triterpene–glycoside conjugates exhibited moderate-to-good inhibitory activity against rabbit muscle GPa. Compound 12 showed the best inhibition with an IC50 value of 1.14 μM. Structure–activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations.

Graphical abstractGlucoconjugates of oleanolic acid linked by either a triazole moiety or an ester function have been synthesized as novel inhibitors of glycogen phosphorylase, Several triterpene-glycoside conjugates exhibited moderate to good inhibitory activity against rabbit muscle GPa.Figure optionsDownload full-size imageDownload as PowerPoint slide