Design, synthesis, and structure-activity relationship studies of a series of [4-(4-carboxamidobutyl)]-1-arylpiperazines: insights into structural features contributing to dopamine D3 versus D2 receptor subtype selectivity

J Med Chem. 2014 Aug 28;57(16):7042-60. doi: 10.1021/jm500801r. Epub 2014 Aug 15.

Abstract

Antagonist and partial agonist modulators of the dopamine D3 receptor (D3R) have emerged as promising therapeutics for the treatment of substance abuse and neuropsychiatric disorders. However, development of druglike lead compounds with selectivity for the D3 receptor has been challenging because of the high sequence homology between the D3R and the dopamine D2 receptor (D2R). In this effort, we synthesized a series of acylaminobutylpiperazines incorporating aza-aromatic units and evaluated their binding and functional activities at the D3 and D2 receptors. Docking studies and results from evaluations against a set of chimeric and mutant receptors suggest that interactions at the extracellular end of TM7 contribute to the D3R versus D2R selectivity of these ligands. Molecular insights from this study could potentially enable rational design of potent and selective D3R ligands.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Arrestins / metabolism
  • CHO Cells / drug effects
  • Chemistry Techniques, Synthetic
  • Cricetulus
  • Dopamine Antagonists / chemistry
  • Dopamine Antagonists / pharmacology*
  • Dopamine D2 Receptor Antagonists / chemistry
  • Dopamine D2 Receptor Antagonists / pharmacology
  • Drug Design
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Ligands
  • Models, Molecular
  • Molecular Docking Simulation
  • Mutation
  • Piperazines / chemical synthesis
  • Piperazines / chemistry*
  • Piperazines / metabolism
  • Receptors, Dopamine D2 / chemistry
  • Receptors, Dopamine D2 / genetics
  • Receptors, Dopamine D2 / metabolism*
  • Receptors, Dopamine D3 / chemistry
  • Receptors, Dopamine D3 / genetics
  • Receptors, Dopamine D3 / metabolism*
  • Structure-Activity Relationship
  • beta-Arrestins

Substances

  • Arrestins
  • Dopamine Antagonists
  • Dopamine D2 Receptor Antagonists
  • Ligands
  • Piperazines
  • Receptors, Dopamine D2
  • Receptors, Dopamine D3
  • beta-Arrestins