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dc.contributor.authorMeiring, Letitia
dc.contributor.authorPetzer, Jacobus P.
dc.contributor.authorPetzer, Anél
dc.identifier.citationMeiring, L. et al. 2013. Inhibition of monoamine oxidase by 3,4-dihydro-2(1H)-quinolinone derivatives. Bioorganic & medicinal chemistry letters, 23(20):5498-5502. []en_US
dc.identifier.issn1464-3405 (Online)
dc.description.abstractIn the present study, a series of 3,4-dihydro-2(1H)-quinolinone derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The 3,4-dihydro-2(1H)- quinolinone derivatives are structurally related to a series of coumarin (1-benzopyran-2-one) derivatives which have been reported to act as MAO-B inhibitors. The results document that the quinolinones are highly potent and selective MAO-B inhibitors with most homologues exhibiting IC50 values in the nanomolar range. The most potent MAO-B inhibitor, 7-(3-bromobenzyloxy)-3,4-dihydro-2(1H)-quinolinone, exhibits an IC50 value of 2.9 nM with a 2750-fold selectivity for MAO-B over the MAO-A isoform. An analysis of the structure–activity relationships for MAO-B inhibition shows that substitution on the C7 position of the 3,4-dihydro-2(1H)-quinolinone scaffold leads to significantly more potent inhibition compared to substitution on C6. In this regard, a benzyloxy substituent on C7 is more favourable than phenylethoxy and phenylpropoxy substitution on this position. It may be concluded that C7-substituted 3,4-dihydro-2(1H)-quinolinones are promising leads for the therapy of Parkinson’s disease.en_US
dc.subjectMonoamine oxidaseen_US
dc.subjectReversible inhibitionen_US
dc.subjectStructure-activity relationshipen_US
dc.titleInhibition of monoamine oxidase by 3,4-dihydro-2(1H)-quinolinone derivativesen_US
dc.contributor.researchID21069565 - Meiring, Letitia
dc.contributor.researchID10727388 - Petzer, Jacobus Petrus
dc.contributor.researchID12264954 - Petzer, Anél

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