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This series displays several alkyl, hydroxy, halogen, and\/or alkoxy groups in both benzene rings of the 3\u2010arylcoumarin scaffold. Most of the compounds studied show high affinity and selectivity for the human monoamine oxidase\u2005B (hMAO\u2010B) isoenzyme, with IC<jats:sub>50<\/jats:sub> values in the low nanomolar and picomolar range. Most of the evaluated compounds display higher MAO\u2010B inhibitory activity and selectivity than selegiline (the reference compound). Coumarin <jats:bold>12<\/jats:bold> (3\u2010(3\u2010bromophenyl)\u20106\u2010methylcoumarin) is the most active compound (IC<jats:sub>50<\/jats:sub>=134\u2005p<jats:sc>M<\/jats:sc>), being 140\u2010fold more active than selegiline and showing the highest specificity for hMAO\u2010B. To better understand the structure\u2013activity relationships, docking experiments were carried out on human monoamine oxidase (A and B) structures. Finally, the prediction of passive blood\u2013brain partitioning, based on in silico derived physicochemical descriptors, was performed.<\/jats:p>","DOI":"10.1002\/cmdc.201300533","type":"journal-article","created":{"date-parts":[[2014,4,8]],"date-time":"2014-04-08T17:39:59Z","timestamp":1396978799000},"page":"1488-1500","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Insight into the Functional and Structural Properties of 3\u2010Arylcoumarin as an Interesting Scaffold in Monoamine Oxidase\u2005B Inhibition"],"prefix":"10.1002","volume":"9","author":[{"given":"Maria Jo\u00e3o","family":"Matos","sequence":"first","affiliation":[]},{"given":"Santiago","family":"Vilar","sequence":"additional","affiliation":[]},{"given":"Ver\u00f3nica","family":"Garc\u00eda\u2010Morales","sequence":"additional","affiliation":[]},{"given":"Nicholas P.","family":"Tatonetti","sequence":"additional","affiliation":[]},{"given":"Eugenio","family":"Uriarte","sequence":"additional","affiliation":[]},{"given":"Lourdes","family":"Santana","sequence":"additional","affiliation":[]},{"given":"Dolores","family":"Vi\u00f1a","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2014,4,8]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm7009364"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jns.2012.05.002"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tips.2004.11.007"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.5607\/en.2011.20.1.1"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-211-33328-0_7"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.genet.39.110304.095804"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1101738"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.275.1.390"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.3949\/ccjm.77a.09103"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbf.290040202"},{"key":"e_1_2_7_11_2","unstructured":"\u00a0"},{"key":"e_1_2_7_12_2","first-page":"197","volume-title":"Monoamine Oxidase: Basic and Clinical Frontiers","author":"Dostert P.","year":"1982"},{"key":"e_1_2_7_13_2","first-page":"437","volume-title":"Chemistry and Biochemistry of Flavoenzymes, Vol.\u20052","author":"Singer T. 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