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Preserving the <jats:italic>trans<\/jats:italic>\u2010stilbene structure, a series of 2\u2010arylbenzofuran and corresponding 3\u2010arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO\u2010A and MAO\u2010B. In general, both types of derivatives were found to be selective MAO\u2010B inhibitors, with IC<jats:sub>50<\/jats:sub> values in the nano\u2010 to micromolar range. 5\u2010Nitro\u20102\u2010(4\u2010methoxyphenyl)benzofuran (<jats:bold>8<\/jats:bold>) is the most active compound of the benzofuran series, presenting MAO\u2010B selectivity and reversible inhibition (IC<jats:sub>50<\/jats:sub>=140\u2005n<jats:sc>M<\/jats:sc>). 3\u2010(4\u2032\u2010Methoxyphenyl)\u20106\u2010nitrocoumarin (<jats:bold>15<\/jats:bold>), with the same substitution pattern as that of compound <jats:bold>8<\/jats:bold>, was found to be the most active MAO\u2010B inhibitor of the coumarin series (IC<jats:sub>50<\/jats:sub>=3\u2005n<jats:sc>M<\/jats:sc>). However, 3\u2010phenylcoumarin <jats:bold>14<\/jats:bold> showed activity in the same range (IC<jats:sub>50<\/jats:sub>=6\u2005n<jats:sc>M<\/jats:sc>), is reversible, and also severalfold more selective than compound <jats:bold>15<\/jats:bold>. Docking experiments for the most active compounds into the MAO\u2010B and MAO\u2010A binding pockets highlighted different interactions between the derivative classes (2\u2010arylbenzofurans and 3\u2010arylcoumarins), and provided new information about the enzyme\u2013inhibitor interaction and the potential therapeutic application of these scaffolds.<\/jats:p>","DOI":"10.1002\/cmdc.201300048","type":"journal-article","created":{"date-parts":[[2013,4,15]],"date-time":"2013-04-15T14:08:51Z","timestamp":1366034931000},"page":"956-966","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["MAO Inhibitory Activity of 2\u2010Arylbenzofurans versus 3\u2010Arylcoumarins: Synthesis, in\u2005vitro Study, and Docking Calculations"],"prefix":"10.1002","volume":"8","author":[{"given":"Giulio","family":"Ferino","sequence":"first","affiliation":[]},{"given":"Enzo","family":"Cadoni","sequence":"additional","affiliation":[]},{"given":"Maria Jo\u00e3o","family":"Matos","sequence":"additional","affiliation":[]},{"given":"Elias","family":"Quezada","sequence":"additional","affiliation":[]},{"given":"Eugenio","family":"Uriarte","sequence":"additional","affiliation":[]},{"given":"Lourdes","family":"Santana","sequence":"additional","affiliation":[]},{"given":"Santiago","family":"Vilar","sequence":"additional","affiliation":[]},{"given":"Nicholas P.","family":"Tatonetti","sequence":"additional","affiliation":[]},{"given":"Matilde","family":"Y\u00e1\u00f1ez","sequence":"additional","affiliation":[]},{"given":"Dolores","family":"Vi\u00f1a","sequence":"additional","affiliation":[]},{"given":"Carmen","family":"Picciau","sequence":"additional","affiliation":[]},{"given":"Silvia","family":"Serra","sequence":"additional","affiliation":[]},{"given":"Giovanna","family":"Delogu","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2013,4,15]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0896-6273(03)00568-3"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-8993(96)00761-5"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbf.290040202"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.85.13.4934"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867305666220314202430"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1471-4159.1990.tb03121.x"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.2610150406"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M006972200"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2004.02.032"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-198937050-00006"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1097\/01.wnf.0000240956.49315.be"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11064-010-0293-1"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867043364810"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/nsb732"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1633804100"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0505975102"},{"key":"e_1_2_7_17_2","first-page":"23","volume":"4","author":"Borges F.","year":"2009","journal-title":"Front. 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