14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

Nick P R Nieland, David Rennison, Jillian H Broadbear, Lauren Purington, James H Woods, John R Traynor, John W Lewis, Stephen M Husbands

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5 Citations (Scopus)

Abstract

14β-4’-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a’s codeinone equivalent 3a, which had potent antinociceptive activity.
Original languageEnglish
Pages (from-to)6926-6930
Number of pages5
JournalJournal of Medicinal Chemistry
Volume52
Issue number21
DOIs
Publication statusPublished - 2009

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