Opioid binding and in vitro profiles of a series of 4-hdroxy-3-methoxyindolomorphinans. Transformation of a delta-selective ligand into a high affinity kappa-selective ligand by introduction of a 5,14-substituted bridge.
J Med Chem
; 46(14): 3174-7, 2003 Jul 03.
Article
em En
| MEDLINE
| ID: mdl-12825957
ABSTRACT
In investigation of the effects of 14-substitution in the indolomorphinan series of delta-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 delta-selectivity, 4b had high kappa-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 kappa-opioid receptor binding motif.
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Base de dados:
MEDLINE
Assunto principal:
Hidrocarbonetos Aromáticos com Pontes
/
Receptores Opioides delta
/
Receptores Opioides kappa
/
Indóis
/
Morfinanos
Limite:
Animals
Idioma:
En
Ano de publicação:
2003
Tipo de documento:
Article