Synthesis of 7-arylmorphinans. Probing the "address" requirements for selectivity at opioid delta receptors.
Basic Information
ID: ALA1131607
Journal: J Med Chem
Title: Synthesis of 7-arylmorphinans. Probing the "address" requirements for selectivity at opioid delta receptors.
Authors: Gao P, Larson DL, Portoghese PS.
Abstract: Through arylation of 6-keto opiates with diaryliodonium iodide, a series of 7-aryl opiates (3-8) have been prepared in an effort to investigate the effect of conformational mobility of the delta "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 delta opioid receptors. It is concluded that the coplanarity of the address moiety with the C ring of the morphinan structure enhances delta antagonist potency and selectivity.
CiteXplore: 9685249
DOI: 10.1021/jm9802214
Patent ID: ┄