Novel quinuclidine-based ligands for the muscarinic cholinergic receptor

J Med Chem. 1990 Apr;33(4):1128-38. doi: 10.1021/jm00166a008.

Abstract

Recent clinical studies on Alzheimer's patients have implied that only agents displaying high efficacy at the cortical muscarinic receptor have yielded encouraging results. This paper describes the design, synthesis, and biochemical characterization of novel quinuclidine-based muscarinic agonists which can readily penetrate into the central nervous system and which are capable of displaying high efficacy at cortical sites. With use of a biochemical assay capable of measuring receptor affinity and predicting cortical efficacy, it has been discovered that an oxadiazole ring and related heterocycles can function as bioisosteric replacements for the ester moiety found in several known muscarinic ligands. Within this series there exist compounds which span the efficacy range from high-efficacy agonist through partial agonists to antagonists with affinity comparable or superior to that of classical quaternary ammonium ligands. Consistent with recent molecular biology studies, structure-activity trends are interpreted in terms of separate binding sites for agonists and antagonists with H-bonding interactions characterizing agonist behavior and lipophilic binding characterizing antagonist behavior. Thus the aminooxadiazole moiety has structural features which are optimized for an agonist profile.

MeSH terms

  • Animals
  • Binding Sites
  • Cerebral Cortex / drug effects
  • Cerebral Cortex / metabolism
  • Computer Simulation
  • Kinetics
  • Models, Chemical
  • Oxadiazoles / metabolism
  • Quinuclidines / chemical synthesis*
  • Quinuclidines / metabolism
  • Quinuclidines / pharmacology
  • Rats
  • Receptors, Muscarinic / drug effects*
  • Receptors, Muscarinic / metabolism
  • Structure-Activity Relationship

Substances

  • Oxadiazoles
  • Quinuclidines
  • Receptors, Muscarinic