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Both isoforms, MAO\u2010A and MAO\u2010B, are known to play critical roles in disease progression, and as such, the identification of novel, potent and selective inhibitors is an important research goal. Here, two series of 3\u2010phenylcoumarin derivatives were synthesized and evaluated against MAO\u2010A and MAO\u2010B. Most of the compounds tested acted preferentially on MAO\u2010B, with IC<jats:sub>50<\/jats:sub> values in the micromolar to nanomolar range. Only 6\u2010chloro\u20104\u2010hydroxy\u20103\u2010(2\u2019\u2010hydroxyphenyl)coumarin exhibited activity against the MAO\u2010A isoform, while still retaining good selectivity for MAO\u2010B. 6\u2010Chloro\u20103\u2010phenylcoumarins unsubstituted at the 4\u2005position were found to be more active as MAO\u2010B inhibitors than the corresponding 4\u2010hydroxylated coumarins. For 4\u2010unsubstituted coumarins, <jats:italic>meta<\/jats:italic> and <jats:italic>para<\/jats:italic> positions on the 3\u2010phenyl ring seem to be the most favorable for substitution. Molecular docking simulations were used to explain the observed hMAO\u2010B structure\u2013activity relationships for this type of compound. 6\u2010Chloro\u20103\u2010(3\u2019\u2010methoxyphenyl)coumarin was the most active compound identified (IC<jats:sub>50<\/jats:sub>=0.001\u2005\u03bc<jats:sc>M<\/jats:sc>) and is several times more potent and selective than the reference compound, <jats:italic>R<\/jats:italic>\u2010(\u2212)\u2010deprenyl hydrochloride. This compound represents a novel tool for the further investigation of the therapeutic potential of MAO\u2010B inhibitors.<\/jats:p>","DOI":"10.1002\/cmdc.201402010","type":"journal-article","created":{"date-parts":[[2014,4,29]],"date-time":"2014-04-29T10:28:25Z","timestamp":1398767305000},"page":"1672-1676","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Monoamine Oxidase (MAO) Inhibitory Activity: 3\u2010Phenylcoumarins versus 4\u2010Hydroxy\u20103\u2010phenylcoumarins"],"prefix":"10.1002","volume":"9","author":[{"given":"Giovanna L.","family":"Delogu","sequence":"first","affiliation":[]},{"given":"Silvia","family":"Serra","sequence":"additional","affiliation":[]},{"given":"Elias","family":"Quezada","sequence":"additional","affiliation":[]},{"given":"Eugenio","family":"Uriarte","sequence":"additional","affiliation":[]},{"given":"Santiago","family":"Vilar","sequence":"additional","affiliation":[]},{"given":"Nicholas P.","family":"Tatonetti","sequence":"additional","affiliation":[]},{"given":"Dolores","family":"Vi\u00f1a","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2014,4,29]]},"reference":[{"key":"e_1_2_4_1_2","first-page":"23","volume":"4","author":"Borges F.","year":"2009","journal-title":"Front. 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