Novel ORL1-selective antagonists with oral bioavailability and brain penetrability

Bioorg Med Chem Lett. 2008 Jun 1;18(11):3282-5. doi: 10.1016/j.bmcl.2008.04.037. Epub 2008 Apr 28.

Abstract

Following the discovery of 5-chloro-6-[piperazin-1-yl]-1H-benzimidazole as a novel pharmacophore for potent and selective ORL1 antagonist activity, optimization of this new lead by introduction of a methyl substitution on the piperazine ring resulted in a highly potent and selective, orally available, and brain penetrable ORL1 antagonist, 2-(tert-butylthio)-5-chloro-6-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-1H-benzimidazole. Stereochemistry of the methyl substituent on the piperazine ring to control the functional activity of other opioid receptors is also described.

MeSH terms

  • Administration, Oral
  • Animals
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Brain / drug effects*
  • Combinatorial Chemistry Techniques
  • Haplorhini
  • Humans
  • Mice
  • Molecular Structure
  • Narcotic Antagonists*
  • Nociceptin Receptor
  • Rats
  • Receptors, Opioid
  • Structure-Activity Relationship

Substances

  • 2-(tert-butylthio)-5-chloro-6-((2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl)-1H-benzimidazole
  • Benzimidazoles
  • Narcotic Antagonists
  • Receptors, Opioid
  • Nociceptin Receptor