Functionalization of the 6,14-bridge of the orvinols. Part 3: Preparation and pharmacological evaluation of 18- and 19-hydroxyl substituted orvinols

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• 作者：Huifang Wu ; Trudy A. Smith ; Hongyan Huang ; Jia Bei Wang ; Jeffrey R. Deschamps ; Andrew Coop
• 关键词：Analgesics ; Partial agonism ; Drug abuse
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2007
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：1 September 2007
• 卷：17
• 期：17
• 页码：4829-4831
• 文件大小：126 K

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 affects the μ opioid efficacy of orvinols.