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3-Amidoquinuclidine Derivatives: Synthesis and Interaction with Butyrylcholinesterase

Renata Odžak
Ines Primožič
Srđanka Tomić

Sažetak

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 Ki = 41.57 µmol 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.

Ključne riječi

3-amidoquinuclidine; quaternary derivatives of 3-amidoquinuclidine; butyrylcholinesterase; chiral inhibitors

Hrčak ID:

12830

URI

https://hrcak.srce.hr/12830

Datum izdavanja:

11.3.2007.

Posjeta: 1.703 *