Synthesis and binding properties of novel selective 5-HT3 receptor ligands

Bioorg Med Chem. 2004 Jul 15;12(14):3891-901. doi: 10.1016/j.bmc.2004.04.043.

Abstract

This work reports on the synthesis and affinities for the 5-HT(3) versus the 5-HT(4) receptor of new piperazinyl-substituted thienopyrimidine derivatives 20-45 with a view to identify potent and selective ligands for the 5-HT(3) receptor. Some of the new compounds show good affinity for the 5-HT(3) receptor and, notably, do not display any affinity for the 5-HT(4) receptor. 4-(4-Methyl-1-piperazinyl)-2-methylthio-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine 31 exhibits the highest affinity for the 5-HT(3) receptor (Ki = 33 nM) and behaves as noncompetitive antagonist.

MeSH terms

  • Animals
  • Guinea Pigs
  • In Vitro Techniques
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Male
  • Protein Binding
  • Rats
  • Receptors, Serotonin, 5-HT3 / metabolism*
  • Serotonin Agents / chemical synthesis*
  • Serotonin Agents / metabolism*
  • Spectrophotometry, Infrared

Substances

  • Ligands
  • Receptors, Serotonin, 5-HT3
  • Serotonin Agents