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

Abstract

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.

DOI: 10.1016/j.ejmech.2015.01.044

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@article{MohammadiKhanaposhtani2015PotentAI, title={Potent acetylcholinesterase inhibitors: design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives.}, author={Maryam Mohammadi-Khanaposhtani and Mina Saeedi and Narges Shamsaei Zafarghandi and Mohammad Mahdavi and Reyhaneh Sabourian and Elahe Karimpour Razkenari and Heshmatollah Alinezhad and Mahnaz Khanavi and Alireza Foroumadi and Abbass Shafiee and Tahmineh Akbarzadeh}, journal={European journal of medicinal chemistry}, year={2015}, volume={92}, pages={799-806} }