In-vitro investigation of oxazol and urea analogues of morphinan at opioid receptors

Bioorg Med Chem. 2007 Jun 15;15(12):4106-12. doi: 10.1016/j.bmc.2007.03.076. Epub 2007 Mar 30.

Abstract

A series of 2-amino-oxazole (7 and 8) analogs and 2-one-oxazole analogs (9 and 10) were synthesized from cyclorphan (1) or butorphan (2) and evaluated in-vitro by their binding affinity at mu, delta, and kappa opioid receptors and compared with their 2-aminothiozole analogs 5 and 6. Ligands 7-10 showed decreased affinities at kappa and mu receptors. Urea analogs (11-14) were also prepared from 2-aminocyclorphan (3) or 2-aminobutorphan (4) and evaluated in-vitro by their binding affinity at mu, delta, and kappa opioid receptors. The urea derived opioids retained their affinities at mu receptors while showing increased affinities at delta receptors and decreased affinities at kappa receptors. Functional activities of these compounds were measured in the [35S]GTPgammaS binding assay, illustrating that all of these ligands were kappa agonists. At the mu receptor, compounds 11 and 12 were mu agonist/antagonists.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Morphinans / chemistry*
  • Morphinans / pharmacology*
  • Oxazoles / chemistry*
  • Receptors, Opioid / drug effects*
  • Urea / chemistry*

Substances

  • Morphinans
  • Oxazoles
  • Receptors, Opioid
  • Urea