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Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives

2015; Elsevier BV; Volume: 92; Linguagem: Inglês

10.1016/j.ejmech.2015.01.044

1768-3254

Maryam Mohammadi‐Khanaposhtani, Mina Saeedi, Narges Shamsaei Zafarghandi, Mohammad Mahdavi, Reyhaneh Sabourian, Elahe Karimpour‐Razkenari, Heshmatollah Alinezhad, Mahnaz Khanavi, Alireza Foroumadi, Abbas Shafiee, Tahmineh Akbarzadeh,

Click Chemistry and Applications

A novel series of acridone linked to 1,2,3-triazole derivatives have been synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. The synthetic approach was started from the reaction of 2-bromobenzoic acid with aniline derivatives and subsequent cyclization reaction to give acridone derivatives. Then, reaction of the later compounds with propargyl bromide followed by azide–alkyne cycloaddition reaction (click reaction) led to the formation of the title compounds in good yields. Among the synthesized compounds, 10-((1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-2-methoxyacridin-9(10H)-one 9g, depicted the most potent anti-AChE activity (IC50 = 7.31 μM). Also, docking study confirmed the results obtained through in vitro experiments and predicted possible binding conformation.