Abstract
Compounds 2-9 possessing a hydroxy or an oxo moiety on the cyclohexane ring of 5-[4-(1-methylcyclohexylmethoxy) benzyl]-2, 4-thiazolidinedione (1, ciglitazone) were synthesized to clarify the structure of the metabolites of 1 and for studies of their pharmacological properties. Of the metabolites identified, 5-[4-(t-3-hydroxy-1-methyl-r-1-cyclohexylmethoxy) benzyl]-2, 4-thiazolidinedione (7) exhibited extremely potent antidiabetic activity compared to 1. Stereoselective syntheses of 3- or 4-hydroxy-1-methylcyclohexanecarboxylic acids required for the preparation of 3'- or 4'-hydroxylated compounds (6, 7 or 3, 4, respectively) are described.
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