Abstract
AbstractDifferent natural and synthetic chalcones have exhibited selective inhibition on monoamine oxidase B (MAO−B) activity, demonstrating potential interest for the treatment of neurodegenerative diseases. Herein we report the synthesis of seven new prenylated chalcones (7a‐g) obtained from the natural compound 5 (4‐hydroxy‐3‐(3‐methylbut‐2‐en‐1‐yl)phenylethanone), previously isolated from S. graveolens. Five of these compounds exhibit high inhibition and selectivity against MAO−B, with IC50 values in the low micromolar range. In addition, the antioxidant activity of this series was measured, being three compounds better than the reference, butylated hydroxytoluene (BHT). Compound 7 f [(2E)‐3‐(4‐(dimethylamino)phenyl)‐1‐(4‐hydroxy‐3‐(3‐methylbut‐2‐en‐1‐yl)phenyl)prop‐2‐en‐1‐one] proved to be the best compound within the studied series (IC50 MAO‐B=8.19 μM and k DPPH=3.73). Finally, molecular docking was performed to better understand the binding properties of these derivatives. Important features for MAO−B inhibitory activity were observed: hydrogen‐bonding interaction between Tyr435 and nearness with Tyr398 and FAD co‐factor. Therefore, these molecules are good candidates for the design of a lead compound for Parkinson's disease.
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