3-Amidoquinuclidine Derivatives: Synthesis and Interaction with Butyrylcholinesterase

Odžak, Renata and Primožič, Ines and Tomić, Srđanka (2007) 3-Amidoquinuclidine Derivatives: Synthesis and Interaction with Butyrylcholinesterase. Croatica Chemica Acta, 80 (1). pp. 101-107. ISSN 0011-1643

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Abstract

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.

Item Type: Article
Keywords: 3-amidoquinuclidine; quaternary derivatives of 3-amidoquinuclidine; butyrylcholinesterase; chiral inhibitors
Date: 2007
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Publisher: Hrvatsko kemijsko društvo
Related URLs:
Depositing User: mag. bibl. Ana Šafran
Date Deposited: 12 May 2014 12:07
Last Modified: 12 May 2014 12:07
URI: http://digre.pmf.unizg.hr/id/eprint/1173

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