Synthesis and properties of [R-(Z)]-(+)-α-(1-azabicyclo[2.2.2]oct-3-yl)-α-(methoxyimino)acetonitrile, a novel functionally selective muscarinic partial agonist

Abstract

The (Z)-N-methoxy imidoyl nitrile functionality is a novel methyl ester bioisostere, which, when substituted onto the quinuclidine ring system gives the title compound 1, a stable, brain penetrant and fuctionally selective muscarinic partial agonist; X-ray studies confirm the configurational assignment and reveal that the imino and cyano bond lengths are consistent with those expected for formal double and triple bonds, respectively.