dc.contributor.author | Mostert, Samantha | |
dc.contributor.author | Mentz, Wayne | |
dc.contributor.author | Petzer, Anél | |
dc.contributor.author | Bergh, Jacobus J. | |
dc.contributor.author | Petzer, Jacobus P. | |
dc.date.accessioned | 2014-01-08T13:00:41Z | |
dc.date.available | 2014-01-08T13:00:41Z | |
dc.date.issued | 2012 | |
dc.identifier.citation | Mostert, S. et al. 2012. Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues. Bioorganic & medicinal chemistry, 20(24):7040-7050. [https://doi.org/10.1016/j.bmc.2012.10.005] | en_US |
dc.identifier.issn | 0968-0896 | |
dc.identifier.issn | 1464-3391 (Online) | |
dc.identifier.uri | http://hdl.handle.net/10394/9887 | |
dc.identifier.uri | https://www.sciencedirect.com/science/article/pii/S0968089612008061 | |
dc.identifier.uri | https://doi.org/10.1016/j.bmc.2012.10.005 | |
dc.description.abstract | In 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.language.iso | en | en_US |
dc.publisher | Elsevier | en_US |
dc.subject | Monoamine oxidase | en_US |
dc.subject | Sulfanylcaffeine | en_US |
dc.subject | Sulfinylcaffeine | en_US |
dc.subject | Reversible inhibition | en_US |
dc.subject | Selective inhibition | en_US |
dc.subject | Caffeine | en_US |
dc.subject | Structure-activity relationship | en_US |
dc.title | Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues | en_US |
dc.type | Article | en_US |
dc.contributor.researchID | 20574991 - Mostert, Samantha | |
dc.contributor.researchID | 12264954 - Petzer, Anél | |
dc.contributor.researchID | 10057072 - Bergh, Jacobus Johannes | |
dc.contributor.researchID | 10727388 - Petzer, Jacobus Petrus | |
dc.contributor.researchID | 21512140 - Mentz, Wayne | |