Design, synthesis and structure-activity relationship studies of hexahydropyrazinoquinolines as a novel class of potent and selective dopamine receptor 3 (D3) ligands

Bioorg Med Chem Lett. 2005 Mar 15;15(6):1701-5. doi: 10.1016/j.bmcl.2005.01.037.

Abstract

A hexahydropyrazinoquinoline (compound 5c) was previously discovered as a novel D3 ligand with a moderate binding affinity to the D3 receptor (Ki=304 nM) but no selectivity over the D1-like and D2-like receptors. In this study, we wish to report the design, synthesis and structure-activity relationship studies of a series of novel hexahydropyrazinoquinolines. Our efforts resulted in new compounds with improved binding affinity and selectivity. Among them, compound 12d has a Ki value of 2.6 nM for its binding affinity to the D3 receptor and has >2000- and 99-fold selectivity over the D1-like and D2-like receptors, respectively, representing a potent and selective D3 ligand.

MeSH terms

  • Animals
  • Brain / metabolism
  • Drug Design
  • Ligands
  • Models, Chemical
  • Molecular Structure
  • Protein Binding
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology*
  • Rats
  • Receptors, Dopamine D2 / metabolism*
  • Receptors, Dopamine D3
  • Structure-Activity Relationship

Substances

  • Drd3 protein, rat
  • Ligands
  • Quinolines
  • Receptors, Dopamine D2
  • Receptors, Dopamine D3