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Using 18beta-glycyrrhetinic acid as a template, the synthesis of a series of secondary amides at the 30-position is described and the effects of these modifications on the SAR of the 11beta-hydroxysteroid dehydrogenase isozymes type 1 and 2 from the rat are investigated. An isoform selective inhibitor has been discovered and compound 5, N-(2-hydroxyethyl)-3beta-hydroxy-11-oxo-18beta-olean-12-en-30-oic acid amide, is highlighted as a very potent and selective inhibitor of 11beta-hydroxysteroid dehydrogenase 2 with an IC(50)=4 pM.

Original publication




Journal article


Bioorg Med Chem Lett

Publication Date





3263 - 3267


11-beta-Hydroxysteroid Dehydrogenase Type 2, Animals, Enzyme Inhibitors, Glucuronides, Glycyrrhetinic Acid, Rats, Rats, Wistar