Design of novel hexahydropyrazinoquinolines as potent and selective dopamine D3 receptor ligands with improved solubility

Bioorg Med Chem Lett. 2006 Jan 15;16(2):443-6. doi: 10.1016/j.bmcl.2005.09.053. Epub 2005 Nov 14.

Abstract

We have recently reported hexahydropyrazinoquinolines as a new class of dopamine 3 (D(3)) receptor ligands with high-affinity to the D(3) receptor and excellent selectivity over the closely related D(1)-like and D(2)-like receptors. However, our previously reported most potent and selective D(3) ligands have poor aqueous solubility, which greatly hinders our in vivo studies aimed at evaluation of their therapeutic potential in animal models. In this study, we wish to report the design, synthesis, and evaluation of a series of new hexahydropyrazinoquinolines as D(3) ligands with improved solubility. Among them, compound 4g has a K(i) value of 9.7 nM for the D(3) receptor and displays a selectivity of >5000 and 466 times over the D(1)-like and D(2)-like receptors, respectively. Importantly, the hydrochloride salt form of compound 4g has a good aqueous solubility (>50 mg/mL) and represents a promising D(3) ligand for further in vivo evaluations of its therapeutic potential for the treatment of drug abuse, restless legs syndrome, schizophrenia, Parkinson's disease, and depression.

MeSH terms

  • Animals
  • Binding Sites
  • Brain / drug effects
  • Drug Design
  • Drug Evaluation, Preclinical
  • In Vitro Techniques
  • Ligands
  • Molecular Structure
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry
  • Pyrazines / pharmacology*
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Rats
  • Receptors, Dopamine D3 / drug effects*
  • Solubility
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Ligands
  • Pyrazines
  • Quinolines
  • Receptors, Dopamine D3