Design, Synthesis and Docking Calculations of Prenylated Chalcones as Selective Monoamine Oxidase B Inhibitors with Antioxidant Activity

Synthesis, MAO−B inhibitory activity and antioxidant profile of new prenylated chalcones obtained from the natural compound 5 (4-hydroxy-3-(3-methylbut-2-en-1-yl)phenylethanone), previously isolated from S. graveolens, are reported. Five compounds exhibit high inhibition and selectivity against MAO−B, with IC50 values in the low micromolar range. In addition, three compounds better antioxidants than butylated hydroxytoluene (BHT). Important features for MAO−B inhibitory activity were observed by docking analysis: H-bonding interaction between Tyr435, Tyr398 and FAD co-factor.