Synthesis and biological activity of 1,2,4-oxadiazole derivatives: highly potent and efficacious agonists for cortical muscarinic receptors

J Med Chem. 1990 Oct;33(10):2690-7. doi: 10.1021/jm00172a003.

Abstract

The synthesis and biochemical evaluation of novel 1,2,4-oxadiazole-based muscarinic agonists which can readily penetrate into the CNS is reported. Efficacy and binding of these compounds are markedly influenced by the structure and physicochemical properties of the cationic head group. In a series of azabicyclic ligands efficacy and affinity are influenced by the size of the surface area presented to the receptor, at the active site, and the degree of conformational flexibility. The exo-1-azanorbornane 16a represents the optimum arrangement, and this compound is one of the most efficacious and potent muscarinic agonists known. In a series of isoquinuclidine based muscarinic agonists efficacy and affinity are influenced by the geometry between the cationic head.group and hydrogen bond acceptor pharmacophore and steric bulk in the vicinity of the base. The anti configuration represented by 22a is optimal for muscarinic activity. Ligands with pKa below 6.5 show poor binding to the muscarinic receptor as exemplified by the diazabicyclic derivative 42.

MeSH terms

  • Animals
  • Cerebral Cortex / drug effects
  • Cerebral Cortex / metabolism
  • In Vitro Techniques
  • Ligands
  • Oxadiazoles / chemical synthesis*
  • Parasympathomimetics / chemical synthesis*
  • Parasympathomimetics / metabolism
  • Rats
  • Receptors, Muscarinic / drug effects*
  • Receptors, Muscarinic / metabolism
  • Receptors, Nicotinic / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Ligands
  • Oxadiazoles
  • Parasympathomimetics
  • Receptors, Muscarinic
  • Receptors, Nicotinic