Medicinal Chemistry Research https://doi.org/10.1007/s00044-019-02330-8 MEDICINAL CHEMISTR Y RESEARCH ORIGINAL RESEARCH Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship Abhijit Karmakar 1 ● Pravin Ambure 2 ● Tamanna Mallick 1 ● Sreeparna Das 1 ● Kunal Roy 2 ● Naznin Ara Begum 1 Received: 23 December 2018 / Accepted: 13 March 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019 Abstract The binding interactions between acetylcholinesterase (AChE) and a series of antioxidant flavonoid analogs were studied by fluorescence spectroscopic assay. The present study incorporated different classes of naturally occurring and synthetic flavonoid compounds like flavones, isoflavones, and chalcones as well as a few standard antioxidants. The AChE inhibitory (AChEI) activity of these compounds was further analyzed using in silico techniques, namely pharmacophore mapping, quantitative structure–activity relationship (QSAR) analysis, and molecular docking studies. We have also compared the AChE inhibitory and radical scavenging antioxidant activities of these compounds. Both the AChE inhibitory and antioxidant activities of these compounds were found to be highly dependent on their structural patterns. However, it was observed that, in general, flavones are comparatively better AChE inhibitors as well as antioxidants compared to chalcones. Graphical Abstract * Kunal Roy kunal.roy@jadavpuruniversity.in * Naznin Ara Begum naznin.begum@visva-bharati.ac.in 1 Department of Chemistry, Siksha-Bhavana, Visva-Bharati (Central University), Santiniketan 731235 West Bengal, India 2 Drug Theoretics and Cheminformatics Laboratory, Department of Pharmaceutical Technology, Jadavpur University, Kolkata 700032 West Bengal, India Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-019-02330-8) contains supplementary material, which is available to authorized users. 1234567890();,: 1234567890();,: