Synthesis and pharmacological evaluation of aminothiazolomorphinans at the mu and kappa opioid receptors

J Med Chem. 2013 Nov 14;56(21):8872-8. doi: 10.1021/jm401290y. Epub 2013 Oct 29.

Abstract

Previous studies with aminothiazolomorphinans suggested that this class of opioid ligands may be useful as a potential pharmacotherapeutic to decrease drug abuse. Novel aminothiazole derivatives of cyclorphan were prepared to evaluate a series of aminothiazolomorphinans with varying pharmacological properties at the κ opioid receptor (KOR) and μ opioid receptor (MOR). This study was focused on exploring the regioisomeric analogs with the aminothiazole on the C-ring of the morphinan skeleton. Receptor binding and [(35)S]GTPγS binding assays were used to characterize the affinity and pharmacological properties of the aminothiazolomorphinans. Intracranial self-stimulation (ICSS) was used to compare the effects of a representative aminothiazolomorphinan with the morphinan mixed-KOR/MOR agonist butorphan (MCL-101) on brain-stimulation reward.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CHO Cells
  • Cricetulus
  • Dose-Response Relationship, Drug
  • Humans
  • Male
  • Molecular Conformation
  • Morphinans / chemical synthesis
  • Morphinans / chemistry
  • Morphinans / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Opioid, kappa / antagonists & inhibitors*
  • Receptors, Opioid, mu / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Morphinans
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • Thiazoles