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

dc.contributor.authorMellado M.
dc.contributor.authorSalas C.O.
dc.contributor.authorUriarte E.
dc.contributor.authorViña D.
dc.contributor.authorJara-Gutiérrez C.
dc.contributor.authorMatos M.J.
dc.contributor.authorCuellar M.
dc.date.accessioned2020-09-02T22:22:53Z
dc.date.available2020-09-02T22:22:53Z
dc.date.issued2019
dc.identifier10.1002/slct.201901282
dc.identifier.citation4, 26, 7698-7703
dc.identifier.issn23656549
dc.identifier.urihttps://hdl.handle.net/20.500.12728/5287
dc.descriptionDifferent 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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.language.isoen
dc.publisherWiley-Blackwell
dc.subjectAntioxidant activity
dc.subjectClaisen-Schmidt reaction
dc.subjectMolecular docking
dc.subjectMonoamine oxidase B inhibitors
dc.subjectPrenyl-chalcones
dc.titleDesign, Synthesis and Docking Calculations of Prenylated Chalcones as Selective Monoamine Oxidase B Inhibitors with Antioxidant Activity
dc.typeArticle


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