A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors

Bioorg Med Chem Lett. 2002 Feb 25;12(4):619-22. doi: 10.1016/s0960-894x(01)00820-4.

Abstract

A series of 7-hydroxy-2-[N-alkyl-(N-(4-phenylpiperazine)-alkyl)amino]tetralins was developed based on a novel hybrid approach that combined 2-aminotetralin and arylpiperazine pharmacophoric moieties. Our preliminary study revealed that a four-methylene butyl linker produced very potent compounds for both the D2 and D3 receptors. Further structure-activity studies led to a novel template showing 50- to 100-fold selectivity for the D3 receptor.

MeSH terms

  • Cell Line
  • Dopamine D2 Receptor Antagonists*
  • Humans
  • Ligands
  • Piperazine
  • Piperazines / chemistry*
  • Piperazines / metabolism
  • Protein Binding
  • Radioligand Assay
  • Receptors, Dopamine D2 / metabolism
  • Receptors, Dopamine D3
  • Spiperone / metabolism
  • Structure-Activity Relationship
  • Tetrahydronaphthalenes / chemistry*
  • Tetrahydronaphthalenes / metabolism

Substances

  • DRD3 protein, human
  • Dopamine D2 Receptor Antagonists
  • Ligands
  • Piperazines
  • Receptors, Dopamine D2
  • Receptors, Dopamine D3
  • Tetrahydronaphthalenes
  • Piperazine
  • 2-aminotetralin
  • Spiperone