Azaindole derivatives with high affinity for the dopamine D4 receptor: synthesis, ligand binding studies and comparison of molecular electrostatic potential maps

Bioorg Med Chem Lett. 1999 Jan 4;9(1):97-102. doi: 10.1016/s0960-894x(98)00692-1.

Abstract

Piperazinylmethyl substituted pyrazolo[1,5-a]pyridines and related heterocycles were synthesized and found to recognize selectively the dopamine D4 receptor. For the most potent derivative 10d a Ki value of 2.0 nM was observed. SAR studies including the comparison of molecular isopotential surfaces were performed.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dopamine Antagonists / chemistry*
  • Dopamine Antagonists / pharmacology*
  • Dopamine D2 Receptor Antagonists*
  • Indoles / chemistry*
  • Indoles / metabolism
  • Isomerism
  • Kinetics
  • Models, Chemical
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Pyridines / chemistry*
  • Pyridines / pharmacology*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Receptors, Dopamine D2 / metabolism*
  • Receptors, Dopamine D4
  • Static Electricity
  • Structure-Activity Relationship
  • Surface Properties

Substances

  • 3-((4-(4-chlorophenyl)piperazin-1-yl)methyl)-1H-pyrrolo(2,3-b)pyridine
  • 3-(4-(4-chlorophenyl)piperazinylmethyl)pyrazolo(1,5-a)pyridine
  • Dopamine Antagonists
  • Dopamine D2 Receptor Antagonists
  • Indoles
  • Pyrazoles
  • Pyridines
  • Pyrroles
  • Receptors, Dopamine D2
  • Receptors, Dopamine D4