Synthesis of 7-arylmorphinans. Probing the 'address' requirements for selectivity at opioid δ receptors

Peng Gao, Dennis L. Larson, Philip S. Portoghese

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Through arylation of 6-keto opiates with diaryliodonium iodide, a series of 7-aryl opiates (38) have been prepared in an effort to investigate the effect of conformational mobility of the δ 'address' moiety on opioid agonist and antagonist potencies. Evaluation of the ligands in the mouse vas deferens and guinea pig ileum preparations revealed that they were less potent and less selective than the conformationally constrained ligands, naltrindole (1, NTI) and 7-(spiroindanyl)oxymorphone (2, SIOM), at δ opioid receptors. It is concluded that the coplanarity of the address moiety with the C ring of the morphinan structure enhances δ antagonist potency and selectivity.

Original languageEnglish (US)
Pages (from-to)3091-3098
Number of pages8
JournalJournal of medicinal chemistry
Volume41
Issue number16
DOIs
StatePublished - Jul 30 1998

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