Opioid binding and in vitro profiles of a series of 4-hydroxy-3-methoxyindolomorphinans. Transformation of a δ-selective ligand into a high affinity κ-selective ligand by introduction of a 5,14-substituted bridge

Peter Grundt, Fernando Martinez-Bermejo, John W. Lewis, Stephen M. Husbands

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

In investigation of the effects of 14-substitution in the indolomorphinan series of δ-selective opioid ligands, 5,14-bridged indolomorphinans (4) were prepared from the equivalent dihydrothebainone acid-catalyzed rearrangement products of the dihydrothevinols. Though the new ligands generally had low affinity for opioid receptors and no δ-selectivity, 4b had high κ-affinity and substantial selectivity which was also seen in the precursor morphinanone (3b). This indicates that the methylbenzylidene-substituted bridge in these compounds is a dominant κ-opioid receptor binding motif.

Original languageEnglish (US)
Pages (from-to)3174-3177
Number of pages4
JournalJournal of medicinal chemistry
Volume46
Issue number14
DOIs
StatePublished - Jul 3 2003

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