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dc.contributor.authorMostert, Samantha
dc.contributor.authorMentz, Wayne
dc.contributor.authorPetzer, Anél
dc.contributor.authorBergh, Jacobus J.
dc.contributor.authorPetzer, Jacobus P.
dc.identifier.citationMostert, S. et al. 2012. Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues. Bioorganic & medicinal chemistry, 20(24):7040-7050. []en_US
dc.identifier.issn1464-3391 (Online)
dc.description.abstractIn a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl)sulfanyl]caffeine (IC50 = 0.223 lM) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl] caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[(phenylethyl)sulfanyl]caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 lM. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl)sulfanyl]caffeine analogues.en_US
dc.subjectMonoamine oxidaseen_US
dc.subjectReversible inhibitionen_US
dc.subjectSelective inhibitionen_US
dc.subjectStructure-activity relationshipen_US
dc.titleInhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analoguesen_US
dc.contributor.researchID20574991 - Mostert, Samantha
dc.contributor.researchID12264954 - Petzer, Anél
dc.contributor.researchID10057072 - Bergh, Jacobus Johannes
dc.contributor.researchID10727388 - Petzer, Jacobus Petrus
dc.contributor.researchID21512140 - Mentz, Wayne

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