Synthesis and Biological Evaluation of 14-Alkoxymorphinans. Part 19 : Effect of 14-O-Benzylation on the Opioid Receptor Affinity and Antagonist Potency of Naltrexone

✍ Scribed by Falko Schüllner; Ruth Meditz; Roland Krassnig; Günther Morandell; Valery N. Kalinin; Ellen Sandler; Mariana Spetea; Angela White; Helmut Schmidhammer; Ilona P. Berzetei-Gurske

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 104 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390187

✦ Synopsis

Abstract

The 14‐O‐benzylnaltrexones 3–6 were prepared from naltrexone (2) in several steps. The novel compounds were biologically evaluated in radioligand binding and in [^35^S]GTP__γ__S functional assays in comparison to the reference compound naltrexone. In the binding assay, compounds 3–6 exhibited preference for κ opioid receptors, while the parent compound naltrexone shows preference for μ receptors. In the functional assay, μ antagonist potency of compounds 3–6 was in the range of naltrexone, while κ antagonist potency was considerably higher for most novel compounds in comparison to naltrexone.