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Racemates as well as (R)- and (S)-enantiomers of 3-pivalamidoquinuclidine (PivQ) and 3-acetamidoquinuclidine (AcQ) were prepared. Their quaternary racemic and enantiomerically pure N-benzyl derivatives (BnlPivQ and BnlAcQ) were synthesized as well. The amides were tested as substrates and inhibitors of butyrylcholinesterase (BChE) from horse serum (EC 3.1.1.8). No hydrolysis was observed under the experimental conditions applied. On the contrary, inhibition of BChE by (R)- and (S)-enantiomers of N-benzylquinuclidinium amides of pivalic acid was observed. The (S)-BnlPivQ with K-i = 41.57 mu mol dm(-3) was 3-fold more potent inhibitor than the (R)-enantiomer. On the other hand, preliminary results indicated that both enantiomers of N-benzylquinuclidinum amides of acetic acid may possibly be inhibitors as well as activators depending on the concentrations of benzoylcholine (BzCh) used as a substrate of BChE.
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Reference:
Quinuclidine – Wikipedia,
,Quinuclidine | C7H13N | ChemSpider