{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,29]],"date-time":"2025-10-29T13:46:41Z","timestamp":1761745601395,"version":"build-2065373602"},"reference-count":46,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2022,1,29]],"date-time":"2022-01-29T00:00:00Z","timestamp":1643414400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002848","name":"Agencia Nacional de Investigaci\u00f3n y Desarrollo","doi-asserted-by":"publisher","award":["Fondecyt Postdoctoral Grant 3180408"],"award-info":[{"award-number":["Fondecyt Postdoctoral Grant 3180408"]}],"id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Vicerrector\u00eda de Investigaci\u00f3n y Estudios Avanzados of Ponti\ufb01cia Universidad Cat\u00f3lica de Valpara\u00edso","award":["VRIEA-PUCV 37.0\/2017"],"award-info":[{"award-number":["VRIEA-PUCV 37.0\/2017"]}]},{"DOI":"10.13039\/501100004837","name":"Ministerio de Ciencia e Innovaci\u00f3n","doi-asserted-by":"publisher","award":["PID2020-116076RJ-I00\/AEI\/10.13039\/501100011033"],"award-info":[{"award-number":["PID2020-116076RJ-I00\/AEI\/10.13039\/501100011033"]}],"id":[{"id":"10.13039\/501100004837","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["CEECIND\/02423\/2018 and UIDB\/00081\/2020"],"award-info":[{"award-number":["CEECIND\/02423\/2018 and UIDB\/00081\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Monoamine oxidases (MAOs) are attractive targets in drug design. The inhibition of one of the isoforms (A or B) is responsible for modulating the levels of different neurotransmitters in the central nervous system, as well as the production of reactive oxygen species. Molecules that act selectively on one of the MAO isoforms have been studied deeply, and coumarin has been described as a promising scaffold. In the current manuscript we describe a comparative study between 3-phenylcoumarin (endo coumarin-resveratrol-inspired hybrid) and trans-6-styrylcoumarin (exo coumarin-resveratrol-inspired hybrid). Crystallographic structures of both compounds were obtained and analyzed. 3D-QSAR models, in particular CoMFA and CoMSIA, docking simulations and molecular dynamics simulations have been performed to support and better understand the interaction of these molecules with both MAO isoforms. Both molecules proved to inhibit MAO-B, with trans-6-styrylcoumarin being 107 times more active than 3-phenylcoumarin, and 267 times more active than trans-resveratrol.<\/jats:p>","DOI":"10.3390\/molecules27030928","type":"journal-article","created":{"date-parts":[[2022,1,30]],"date-time":"2022-01-30T00:12:56Z","timestamp":1643501576000},"page":"928","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Coumarin-Resveratrol-Inspired Hybrids as Monoamine Oxidase B Inhibitors: 3-Phenylcoumarin versus\u00a0trans-6-Styrylcoumarin"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9577-5180","authenticated-orcid":false,"given":"Marco","family":"Mellado","sequence":"first","affiliation":[{"name":"Instituto de Investigaci\u00f3n y Postgrado, Facultad de Ciencias de la Salud, Universidad Central de Chile, Santiago 8330507, Chile"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0830-8507","authenticated-orcid":false,"given":"C\u00e9sar","family":"Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2340000, Chile"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2434-8461","authenticated-orcid":false,"given":"Jaime","family":"Mella","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica y Bioqu\u00edmica, Facultad de Ciencias, Universidad de Valpara\u00edso, Valpara\u00edso 2340000, Chile"},{"name":"Centro de Investigaci\u00f3n Farmacopea Chilena (CIFAR), Universidad de Valpara\u00edso, Valpara\u00edso 2340000, Chile"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6038-3475","authenticated-orcid":false,"given":"Luis F.","family":"Aguilar","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Facultad de Ciencias, Pontificia Universidad Cat\u00f3lica de Valpara\u00edso, Valpara\u00edso 2340000, Chile"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8146-1663","authenticated-orcid":false,"given":"Ismail","family":"Celik","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, 38000 Kayseri, Turkey"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1050-2402","authenticated-orcid":false,"given":"Fernanda","family":"Borges","sequence":"additional","affiliation":[{"name":"CIQUP, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade do Porto, 4169-007 Porto, Portugal"}]},{"given":"Eugenio","family":"Uriarte","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Farmacia, Universidade Santiago de Compostela, 15782 Santiago de Compostela, Spain"},{"name":"Instituto de Ciencias Qu\u00edmicas Aplicadas, Universidad Aut\u00f3noma de Chile, Santiago 7500912, Chile"}]},{"given":"Giovanna","family":"Delogu","sequence":"additional","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Monserrato, 09042 Cagliari, Italy"}]},{"given":"Dolores","family":"Vi\u00f1a","sequence":"additional","affiliation":[{"name":"Chronic Diseases Pharmacology Group, Center for Research in Molecular Medicine and Chronic Diseases (CIMUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain"},{"name":"Departamento de Farmacolog\u00eda, Farmacia y Tecnolog\u00eda Farmac\u00e9utica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3470-8299","authenticated-orcid":false,"given":"Maria J.","family":"Matos","sequence":"additional","affiliation":[{"name":"CIQUP, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade do Porto, 4169-007 Porto, Portugal"},{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Farmacia, Universidade Santiago de Compostela, 15782 Santiago de Compostela, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2022,1,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"195","DOI":"10.2174\/1871527319666200525011110","article-title":"Overview of Therapeutic Drugs and Methods for the Treatment of Parkinson\u2032s Disease","volume":"19","author":"Schneider","year":"2020","journal-title":"CNS Neurol. 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