Indoline and piperazine containing derivatives as a novel class of mixed D(2)/D(4) receptor antagonists. Part 1: identification and structure-activity relationships

Bioorg Med Chem Lett. 2002 Nov 4;12(21):3105-9. doi: 10.1016/s0960-894x(02)00655-8.

Abstract

Optimization of the lead compound 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2,3-dihydro-indol-1-yl)-ethanone 1 by systematic structure-activity relation (SAR) studies lead to two potent compounds 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2-methy-2,3-dihydro-indol-1-yl)-ethanone 2n and 2-[-4-(4-chloro-benzyl)-piperazin-1-yl]-1-(2-methy-2,3-dihydro-indol-1-yl)-ethanone 7b. Their related synthesis was also reported.

MeSH terms

  • Animals
  • Binding, Competitive / drug effects
  • Dopamine Antagonists / chemical synthesis*
  • Dopamine Antagonists / pharmacology*
  • Dopamine D2 Receptor Antagonists*
  • Glycine / chemistry
  • Humans
  • In Vitro Techniques
  • Indoles / chemical synthesis*
  • Indoles / pharmacology*
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology*
  • Prazosin / metabolism
  • Rats
  • Receptors, Dopamine D4
  • Recombinant Proteins / drug effects
  • Structure-Activity Relationship

Substances

  • 2-(-4-(4-chloro-benzyl)-piperazin-1-yl)-1-(2,3-dihydro-indol-1-yl)-ethanone
  • 2-(-4-(4-chloro-benzyl)-piperazin-1-yl)-1-(2-methy-2,3-dihydro-indol-1-yl)-ethanone
  • DRD4 protein, human
  • Dopamine Antagonists
  • Dopamine D2 Receptor Antagonists
  • Drd4 protein, rat
  • Indoles
  • Piperazines
  • Recombinant Proteins
  • Receptors, Dopamine D4
  • Glycine
  • Prazosin