Synthesis, structure-activity relationship, and receptor pharmacology of a new series of quinoline derivatives acting as selective, noncompetitive mGlu1 antagonists

J Med Chem. 2005 Mar 24;48(6):2134-53. doi: 10.1021/jm049499o.

Abstract

We describe the discovery and the structure-activity relationship of a new series of quinoline derivatives acting as selective and highly potent noncompetitive mGlu1 antagonists. We first identified cis-10 as a fairly potent mGlu1 antagonist (IC(50) = 20 nM) in a cell-based signal transduction assay on the rat mGlu1 receptor expressed in CHO-K1 cells, and then we were able to design and synthesize highly potent compounds on both rat and human mGlu1 receptors as exemplified by compound cis-64a, which has an antagonist potency of 0.5 nM for the human mGlu1 receptor. We briefly present and discuss the in vitro metabolic stability of the compounds in human liver microsomes. We finally report the pharmacokinetic properties of our lead compound cis-64a.

MeSH terms

  • Animals
  • Biological Availability
  • CHO Cells
  • Calcium / metabolism
  • Cell Line, Tumor
  • Cricetinae
  • Cricetulus
  • Half-Life
  • Humans
  • In Vitro Techniques
  • Intracellular Fluid / metabolism
  • Microsomes, Liver / metabolism
  • Quinolines / chemical synthesis*
  • Quinolines / pharmacokinetics
  • Quinolines / pharmacology
  • Rats
  • Receptors, Metabotropic Glutamate / antagonists & inhibitors*
  • Receptors, Metabotropic Glutamate / physiology
  • Signal Transduction / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 3,4-dihydro-2H-pyrano(2,3-b)quinolin-7-yl 4-methoxycyclohexyl ketone
  • Quinolines
  • Receptors, Metabotropic Glutamate
  • metabotropic glutamate receptor type 1
  • Calcium