Synthesis of various geometric and enantiomeric oxime O-(α and β methylcholinyl) ethers as potential anticholinergic agents

Article abstract of DOI:10.1002/jps.2600660817

Various enantiomeric and geometric oxime O (α and β methylcholinyl) ethers were synthesized as potential anticholinergic agents. The synthesis, separation, resolution, and structural characterization of these compounds are reported. The first step of the synthetic pathway involved an oxime formation, with subsequent O alkylation of the respective oxime with 2 chloro N,N dimethylpropylamine hydrochloride. The separation of the α and β structural isomers utilized vacuum fractional distillation and/or column chromatography, and the resolution of the enantiomers was accomplished via the formation of tartrate diastereoisomers. A preliminary pharmacological evaluation for anticholinergic activity was conducted using a rat ileum assay. Structure activity relationships, including some stereochemical properties and antimuscarinic activity, are discussed.