Synthesis and preliminary pharmacological results on new naphthalene derivatives as 5-HT(4) receptor ligands

Eur J Med Chem. 2000 Jul-Aug;35(7-8):699-706. doi: 10.1016/s0223-5234(00)00163-x.

Abstract

The indole derivative GR 113808 is currently used as the reference ligand for labelling the 5-HT(4) serotoninergic receptors. Previous works in our laboratories established the bioisosteric equivalency of the indole heterocycle and naphthalene in a series of melatonin receptor ligands. Based on this knowledge we designed new analogues of GR 113808 by introducing two bioisosteric modifications: firstly, the indole ring was replaced by a naphthalene one and secondly, the ester linkage was replaced by an amide group. Compound 8 emerged within this novel series as it displayed high and selective affinity at 5-HT(4) receptors (Ki 5-HT(4) = 6 nM, Ki 5-HT(3) = 100 nM, Ki values at other 5-HT receptors were higher than 1000 nM). Compound 8 is currently undergoing further pharmacological evaluation.

MeSH terms

  • Indoles / chemistry
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / metabolism
  • Naphthalenes / pharmacology*
  • Protein Binding
  • Receptors, Serotonin / metabolism*
  • Receptors, Serotonin, 5-HT4
  • Serotonin Antagonists / chemistry
  • Sulfonamides / chemistry

Substances

  • Indoles
  • Ligands
  • Naphthalenes
  • Receptors, Serotonin
  • Serotonin Antagonists
  • Sulfonamides
  • Receptors, Serotonin, 5-HT4
  • GR 113808