- Benzofuran-derived benzylpyridinium bromides as potent acetylcholinesterase inhibitors
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A series of benzofuran-based N-benzylpyridinium derivatives 5a-o were designed and synthesized as novel AChE inhibitors. The synthetic pathway of the compounds involved the preparation of 4-(benzofuran-2-yl)pyridine intermediates via the reaction of different salicylaldehyde derivatives and 4-(bromomethyl)pyridine, followed by intramolecular cyclization. Subsequently, the 4-(benzofuran-2-yl)pyridines were N-benzylated by using appropriate benzyl bromide to afford the final product 5a-o. The results of in vitro AChE activity evaluation of synthesized compounds revealed that all compound had potent anti-AChE activity comparable or more potent than standard drug donepezil. The N-(3,5-dimethylbenzyl) derivative 5e with IC50 value of 4.1 nM was the most active compound, being 7-fold more potent than donepezil.
- Baharloo, Farzaneh,Moslemin, Mohammad Hossein,Nadri, Hamid,Asadipour, Ali,Mahdavi, Mohammad,Emami, Saeed,Firoozpour, Loghman,Mohebat, Razieh,Shafiee, Abbas,Foroumadi, Alireza
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p. 196 - 201
(2015/03/05)
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- Bronsted acid catalyzed intramolecular benzylic cyclizations of alkylpyridines
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Aldehyde and ketone electrophiles incorporated into the side chains of 2- and 4-alkylpyridines participate in intramolecular aldol-like condensations with pyridine benzylic carbons in the presence of Bronsted acid catalysts. Pyridines featuring β-ketoamid
- Lansakara, Ashabha I.,Farrell, Daniel P.,Pigge, F. Christopher
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p. 1090 - 1099
(2014/02/14)
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- One-pot synthesis of useful heterocycles in medicinal chemistry using a cascade strategy
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To access useful heterocycles in medicinal chemistry such as pyridazinones, dihydropyrimidinones, and dihydropyrimidinthiones, a "green" mild and highly efficient one-pot triple cascade was developed involving a Claisen-decarboxylation, electrophilic reaction, and subsequent heterocyclization. In addition, indazoles and benzofurans could also be constructed via a double cascade. To develop the cascade process, a direct Claisen-decarboxylation reaction was firstly optimized. This reaction can then couple with electrophilic reactions including alkylation, Michael addition or aldol reaction to enable the preparation of various aryl ketones in a one-pot fashion. The Royal Society of Chemistry 2012.
- Wu, Guiyong,Yin, Weiyu,Shen, Hong C.,Huang, Yong
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supporting information; experimental part
p. 580 - 585
(2012/04/23)
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