Functionalization of the 614-bridge of the orvinols. 3.1 Preparation and pharmacological evaluation of 18- and 19-hydroxyl substituted orvinols

摘要

The orvinols are a class of potent opioids which have been extensively studied, yet little is known about the effects of introducing substituents into the 18- and 19-positions. The etheno bridge of thevinone was hydroxylated to give both the 18- and 19-hydroxyl substituted thevinols. After 3-O-demethylation to the corresponding orvinols, binding and GTPγS functional assays indicated that hydroxyl substitution at the 18- and 19-positions differentially affect the μ opioid efficacy of orvinols.