Syntheses of 4,6'-epoxymorphinan derivatives and their pharmacologies

Bioorg Med Chem. 2008 Apr 15;16(8):4304-12. doi: 10.1016/j.bmc.2008.02.082. Epub 2008 Feb 29.

Abstract

A modification of the message site in the skeleton of naltrexone was carried out to improve the potency and selectivity of the compound for an opioid receptor subtype. In the course of conversion, we synthesized 7-membered ring ether derivatives, which had an inserted OCH(2) group between 4- and 6-positions of morphinan skeleton. One of the 7-membered ring ether derivatives possessed more potent antagonistic activity than naltrexone for the mu opioid receptor. Another compound possessing 17-methyl group derived from noroxycodone may be a mu opioid receptor partial agonist and showed analgesic activity. We are currently examining the subtype selectivity of these compounds.

MeSH terms

  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • GTP-Binding Proteins / metabolism
  • Guinea Pigs
  • Ligands
  • Male
  • Mice
  • Molecular Structure
  • Morphinans / chemical synthesis*
  • Morphinans / chemistry
  • Morphinans / pharmacology*
  • Protein Binding
  • Receptors, Opioid / metabolism
  • Structure-Activity Relationship

Substances

  • Ligands
  • Morphinans
  • Receptors, Opioid
  • GTP-Binding Proteins