Synthesis and preliminary pharmacological evaluation of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes as dopamine receptor ligands

Farmaco. 2002 Apr;57(4):303-13. doi: 10.1016/s0014-827x(02)01206-5.

Abstract

A series of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes were synthesized and evaluated for their binding affinity toward D1-like and D2-like dopamine (DA) receptors. The affinity and selectivity of these compounds were measured in a test involving displacement of [3H]SCH 23390 or [3H]YM-09-151-2, respectively, from homogenates of porcine striatal membranes. All tested compounds were poorly effective at DA receptors (Ki nM > 1000). The results suggest that introduction of chlorine substituent in five or six position of previously synthesized trans-2-amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes decreases both D1-like and D2-like receptor affinity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding, Competitive
  • Corpus Striatum / drug effects
  • Corpus Striatum / metabolism
  • In Vitro Techniques
  • Indenes / chemical synthesis*
  • Indenes / pharmacology*
  • Ligands
  • Radioligand Assay
  • Receptors, Dopamine D1 / drug effects*
  • Receptors, Dopamine D2 / drug effects*
  • Structure-Activity Relationship
  • Swine

Substances

  • Indenes
  • Ligands
  • Receptors, Dopamine D1
  • Receptors, Dopamine D2