An evaluation of 3,4-methylenedioxy phenyl replacements in the aminopiperidine chromone class of MCHr1 antagonists

Bioorg Med Chem Lett. 2007 Feb 15;17(4):874-8. doi: 10.1016/j.bmcl.2006.11.065. Epub 2006 Dec 1.

Abstract

The optimization of potent MCHr1 antagonist 1 with respect to improving its in vitro profile by replacement of the 3,4-methylenedioxy phenyl (piperonyl) moiety led to the discovery of 19, a compound that showed excellent MCHr1 binding and functional potencies in addition to possessing superior hERG separation, CYP3A4 profile, and receptor cross-reactivity profiles.

MeSH terms

  • Alkylation
  • Animals
  • Chemical Phenomena
  • Chemistry, Physical
  • Chromones
  • Cross Reactions
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 Enzyme Inhibitors
  • Dose-Response Relationship, Drug
  • ERG1 Potassium Channel
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Ether-A-Go-Go Potassium Channels / pharmacology
  • Heart Rate / drug effects
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / pharmacology
  • Humans
  • Mice
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacology*
  • Receptors, Somatostatin / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Chromones
  • Cytochrome P-450 Enzyme Inhibitors
  • ERG1 Potassium Channel
  • Enzyme Inhibitors
  • Ether-A-Go-Go Potassium Channels
  • Heterocyclic Compounds
  • KCNH2 protein, human
  • MCHR1 protein, human
  • Piperidines
  • Receptors, Somatostatin
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human