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In this study, a series of naringenin- O -alkylamine derivatives were designed and obtained by introducing an alkylamine fragment into the naringenin skeleton. The  in vitro  biological activity results revealed that compounds  5f  and  7k  showed good antioxidant activity with ORAC values of 2.3 eq  and 1.2 eq , respectively. Compounds  5f  and  7k  were reversible and excellent  hu AChE inhibitors with IC 50  values of 0.91 μM and 0.57 μM, respectively. Moreover, compounds  5f  and  7k  could inhibit self-induced A β1–42  aggregation with 62.1% and 43.8% inhibition rate, respectively, and significantly inhibited  hu AChE-A β1–40  aggregation with 51.7% and 43.4% inhibition rate, respectively. In addition, compounds  5f  and  7k  were selective metal chelators and remarkably inhibited Cu 2+ -induced A β1–42  aggregation with 73.5% and 68.7% inhibition rates, respectively. Furthermore, compounds  5f  and  7k  could cross  the  blood-brain barrier  in vitro  and displayed good neuroprotective effects and anti-inflammatory properties. Further investigation showed that compound  5f  did not show obvious hepatotoxicity and displayed a good hepatoprotective effect by its antioxidant activity. The  in vivo  study displayed that compound  5f  significantly improved scopolamine-induced mice memory impairment. Therefore, compound  5f  was a potential multifunctional candidate for the treatment of AD.

Development of naringenin- O -alkylamine derivatives as multifunctional agents for the treatment of Alzheimer’s disease