Discovery and pharmacological profile of new 1H-indazole-3-carboxamide and 2H-pyrrolo[3,4-c]quinoline derivatives as selective serotonin 4 receptor ligands

J Med Chem. 2012 Nov 26;55(22):9446-66. doi: 10.1021/jm300573d. Epub 2012 Oct 24.

Abstract

Since the discovery of the serotonin 4 receptor (5-HT(4)R), a large number of receptor ligands have been studied. The safety concerns and the lack of market success of these ligands have mainly been attributed to their lack of selectivity. In this study we describe the discovery of N-[(4-piperidinyl)methyl]-1H-indazole-3-carboxamide and 4-[(4-piperidinyl)methoxy]-2H-pyrrolo[3,4-c]quinoline derivatives as new 5-HT(4)R ligands endowed with high selectivity over the serotonin 2A receptor and human ether-a-go-go-related gene potassium ion channel. Within these series, two molecules (11 ab and 12 g) were identified as potent and selective 5-HT(4)R antagonists with good in vitro pharmacokinetic properties. These compounds were evaluated for their antinociceptive action in two analgesia animal models. 12 g showed a significant antinociceptive effect in both models and is proposed as an interesting lead compound as a 5-HT(4)R antagonist with analgesic action.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Computational Biology
  • Dogs
  • Drug Design*
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors
  • Ether-A-Go-Go Potassium Channels / metabolism
  • Humans
  • Ligands
  • Macaca fascicularis
  • Mice
  • Microsomes, Liver / drug effects*
  • Molecular Structure
  • Nociception / drug effects*
  • Protein Binding
  • Quinolines / chemical synthesis
  • Quinolines / pharmacology*
  • Radioligand Assay
  • Rats
  • Receptors, Serotonin, 5-HT4 / metabolism*
  • Structure-Activity Relationship
  • Swine

Substances

  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • KCNH2 protein, human
  • Ligands
  • Quinolines
  • Receptors, Serotonin, 5-HT4