3-Amidoquinuclidine derivatives: synthesis of compounds and inhibition of butyrylcholinesterase |
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Authors: | Odzak Renata Tomić Srdanka |
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Affiliation: | Laboratory of Organic Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102A, HR-10 000 Zagreb, Croatia. rodzak@chem.pmf.hr |
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Abstract: | The synthesis of racemic and enantiomerically pure 3-butanamidoquinuclidines ((+/-)-Bu, (R)-Bu and (S)-Bu), (1-3) and 3-benzamidoquinuclidines ((+/-)-Bz, (R)-Bz, and (S)-Bz), (4-6) is described. The N-quaternary derivatives, N-benzyl-3-butanamidoquinuclidinium bromides ((+/-)-BnlBu, (R)-BnlBu and (S)-BnlBu), (7-9) and N-benzyl-3-benzamidoquinuclidinium bromides ((+/-)-BnlBz, (R)-BnlBz and (S)-BnlBz), (10-12) were subsequently synthesized. The interaction of the four enantiomerically pure quaternary derivatives with horse serum butyrylcholinesterase (BChE) was tested. All tested compounds inhibited the enzyme. The best inhibitior of the enzyme was (S)-BnlBz with a K(i) = 3.7 microM. The inhibitor potency decreases in order (S)-BnlBz > (R)-BnlBz > (R)-BnlBu > (S)-BnlBu. |
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Keywords: | 3-Amidoquinuclidines Quaternary 3-amidoquinuclidines Synthesis Butyrylcholinesterase inhibition |
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