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 language | English (US) |
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Pages (from-to) | 3174-3177 |
Number of pages | 4 |
Journal | Journal of medicinal chemistry |
Volume | 46 |
Issue number | 14 |
DOIs | |
State | Published - Jul 3 2003 |