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  • Title: Synthesis of 3-deoxypentacyclic triterpene derivatives as inhibitors of glycogen phosphorylase.
    Author: Zhang P, Hao J, Liu J, Lu Q, Sheng H, Zhang L, Sun H.
    Journal: J Nat Prod; 2009 Aug; 72(8):1414-8. PubMed ID: 19642687.
    Abstract:
    The 3-deoxy-2-keto derivatives 5 and 7 of oleanolic acid (1) and ursolic acid (2), respectively, served as precursors to the synthesis of 35 3-deoxy derivatives of pentacyclic triterpenes. The synthesized compounds were biologically assayed for their inhibitory activity against rabbit muscle glycogen phosphorylase a (GPa). Among this series of compounds, 2alpha-hydroxyurs-12-en-28-oic acid (18) (IC(50) = 1.2 microM) exhibited the most potent activity. Preliminary structure-activity relationship analysis for the 3-deoxy triterpene derivatives as GP inhibitors is also discussed.
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