engleski

Preparation of quinuclidin-3-ol enantiomers and their interaction with human cholinesterases

The (R)- and (S)- enantiomers of quinuclidin-3-ol, (R)- and (S)-QOH were prepared by resolution of commercially available racemic quinuclidin-3-ol using D- and L- tartaric acid. (R)- and (S)- quinuclidin-3-yl-acetates, (R)- and (S)-QA were synthesized by esterification of (R)- and (S)-QOH with acetic anhydride. Subsequently both enantiomers of quaternary N-metyl alcohols and acetates (MetQOH and MetQA) were prepared using methyl iodide as a quaternization agent. Enantiomers of quaternary N-benzyl alcohols and acetates (BzQOH and BzQA) were synthesized in a similar manner by using benzyl bromid as a quaternization agent. All prepared compounds were then tested as substrates of acetylcholinesterase and butyrylcholinesterase, and/or inhibitors of the cholinesterases.

syntheses ; quaternization ; resolution of enantiomers ; N-benzyl and N-metyl acetates of quinuclidin-3-ol

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