Design, synthesis, and evaluation of hexahydrobenz[f]isoquinolines as a novel class of dopamine 3 receptor ligands

Bioorg Med Chem Lett. 2004 Dec 6;14(23):5813-6. doi: 10.1016/j.bmcl.2004.09.047.

Abstract

We previously identified hexahydrobenz[f]isoquinoline (4a) as a new class of dopamine 3 receptor (D(3)) ligand. Herein, we described the design, synthesis, and preliminary structure-activity relationships of new analogues of 4a as a novel class of D(3) ligands. Among these new analogues, compound 4 h is a potent D(3) ligand (K(i)=6.1 nM) and has a selectivity of 133-fold between D(3)- and D(2)-like receptors, and of 163-fold between D(3)- and D(1)-like receptors, respectively. Thus, compound 4 h represents a promising new lead compound for further design and optimization toward achieving highly potent and selective D(3) ligands.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Brain / metabolism
  • Drug Design*
  • Drug Evaluation, Preclinical / methods
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / metabolism*
  • Ligands
  • Male
  • Protein Binding / physiology
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Dopamine D2 / metabolism*
  • Receptors, Dopamine D3
  • Structure-Activity Relationship

Substances

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