Spirocyclic pyridoazepine analogues of galanthamine: synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase

S Vanlaer, WM De Borggraeve, A Voet…

Index: Vanlaer, Sofie; De Borggraeve, Wim M.; Voet, Arnout; Gielens, Constant; De Maeyer, Marc; Compernolle, Frans European Journal of Organic Chemistry, 2008 , # 15 p. 2571 - 2581

Full Text: HTML

Citation Number: 5

Abstract

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 ...