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Title: Spirocyclic pyridoazepine analogues of galanthamine: Synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase
Authors: Vanlaer, Sofie
De Borggraeve, Wim
Voet, Arnout
Gielens, Constant
De Maeyer, Marc
Compernolle, Frans # ×
Issue Date: May-2008
Publisher: Wiley-v c h verlag gmbh
Series Title: European journal of organic chemistry issue:15 pages:2571-2581
Abstract: Spirocyclic pyridoazepines, designed as simplified analogues of the alkaloid galanthamine, were synthesised and evaluated as inhibitors of acetylcholinesterase. The key cyclisation step involved internal displacement of 2-chloro or 2-iodopyridine by either nucleophilic aromatic substitution or a Heck reaction. The target compounds showed significant inhibition of acetylcholinesterase but lower than that of galanthamine. This result could be rationalised by comparative docking simulation studies based on the known crystal structure of the acetylcholinesterase-galanthamine complex; multiple hydrogen bonding of a cocrystallised water molecule to both the receptor and the ligand Was found to be of crucial importance for effective binding to the active site of the enzyme. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
ISSN: 1434-193X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Chemistry - miscellaneous
Molecular Design and Synthesis
Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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