Synthesis and cholinesterase inhibitory activity of new 2-benzofuran carboxamide-benzylpyridinum salts |
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| Institution: | 1. Department of Chemistry, The Chinese University of Hong Kong, Shatin, China;4. Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules & Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, Shenzhen, China;5. Department of Chemistry & State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, China;1. Centro de Química Estrutural, Instituto Superior Técnico, Universidade Técnica de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal;2. Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Kanakapura, Ramanagara, Bangalore 562112, India;3. CNC–Center for Neuroscience and Cell Biology, University of Coimbra, Coimbra, Portugal;4. Institute of Cell and Molecular Biology, Faculty of Medicine, University of Coimbra, Coimbra, Portugal |
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| Abstract: | A series of benzofuran-2-carboxamide-N-benzyl pyridinium halide derivatives (6a-o) are synthesized as new cholinesterase inhibitors. The synthetic pathway involves the reaction of salicylaldehyde derivatives and ethyl bromoacetate, followed by hydrolysis and amidation with 3- and 4-picolyl amine. Subsequently, N-((pyridin-4-yl) methyl) benzofuran-2-carboxamide and substituted N-((pyridin-3-yl) methyl) benzofuran-2-carboxamides reacts with benzyl halides to afford target compounds (6a-o). The chemical structures of all derivatives were confirmed by spectroscopic methods. The studies reveal that some of the synthesized compounds are potent butyrylcholinesterase inhibitors with IC50 values in the range of 0.054–2.7 µM. In addition, good inhibitory effects on Aβ self-aggregation are observed for 6h and 6k (33.1 and 46.4% at 100 µM, respectively). |
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| Keywords: | Alzheimer’s disease Benzofuran-2-carboxamide Benzylpyridinium Cholinesterase inhibitor |
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