{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T20:47:06Z","timestamp":1785358026619,"version":"3.55.0"},"reference-count":41,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2021,1,21]],"date-time":"2021-01-21T00:00:00Z","timestamp":1611187200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2021,3,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A small collection of C<jats:sub>2<\/jats:sub>\u2010symmetric hydroxylated biphenyl derivatives featuring an \u03b1,\u03b2\u2010unsaturated ketone as a lead structure was prepared, and the capacity of these compounds to act as antiproliferative agents against four human malignant melanoma cell lines was assayed. The prodrug approach was applied in order to improve the delivery of compounds into the cell by modulation of the phenolic hydroxy protecting group. The hydroxylated biphenyl structure bearing an \u03b1,\u03b2\u2010unsaturated ketone and a phenolic\u2010O\u2010prenylated chain was found to facilitate the delivery of the molecule and interactions with biological targets. Four compounds showed antiproliferative activity resulting in IC<jats:sub>50<\/jats:sub> values in the range of 1.2 to 2.8\u2005\u03bcM.<\/jats:p>","DOI":"10.1002\/cmdc.202000709","type":"journal-article","created":{"date-parts":[[2020,12,4]],"date-time":"2020-12-04T07:15:16Z","timestamp":1607066116000},"page":"1022-1033","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Synthesis of Hydroxylated Biphenyl Derivatives Bearing an \u03b1,\u03b2\u2010Unsaturated Ketone as a Lead Structure for the Development of Drug Candidates against Malignant Melanoma"],"prefix":"10.1002","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8776-9271","authenticated-orcid":false,"given":"Maria Antonietta","family":"Dettori","sequence":"first","affiliation":[{"name":"Consiglio Nazionale Ricerche Istituto di Chimica Biomolecolare  Traversa La Crucca 3 07100 Sassari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0649-1010","authenticated-orcid":false,"given":"Marina","family":"Pisano","sequence":"additional","affiliation":[{"name":"Consiglio Nazionale Ricerche Istituto di Ricerca Genetica e Biomedica  Traversa La Crucca 3 07100 Sassari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6581-2227","authenticated-orcid":false,"given":"Carla","family":"Rozzo","sequence":"additional","affiliation":[{"name":"Consiglio Nazionale Ricerche Istituto di Ricerca Genetica e Biomedica  Traversa La Crucca 3 07100 Sassari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8650-387X","authenticated-orcid":false,"given":"Giovanna","family":"Delogu","sequence":"additional","affiliation":[{"name":"Consiglio Nazionale Ricerche Istituto di Chimica Biomolecolare  Traversa La Crucca 3 07100 Sassari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3947-5164","authenticated-orcid":false,"given":"Davide","family":"Fabbri","sequence":"additional","affiliation":[{"name":"Consiglio Nazionale Ricerche Istituto di Chimica Biomolecolare  Traversa La Crucca 3 07100 Sassari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,1,21]]},"reference":[{"key":"e_1_2_10_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4np00010b"},{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1155\/2019\/5245034"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1056\/NEJMra052166"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tranon.2017.09.007"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12986-019-0365-4"},{"key":"e_1_2_10_6_1","first-page":"25","volume":"6","author":"Fuggetta M. P.","year":"2012","journal-title":"Med. Aromat. Plant Sci. Biotechnol."},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.2174\/092986732102131206115810"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/mp700113r"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107724"},{"key":"e_1_2_10_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107724"},{"key":"e_1_2_10_10_1","doi-asserted-by":"crossref","unstructured":"C.\u2005M. Cabello W.\u2005B. Bair\u20053rd S.\u2005D. Lamore S. Ley A.\u2005S. Bause S. Azimian G.\u2005T. Wondrak Free Radical Biol. Med.2009 46 220\u2013231.","DOI":"10.1016\/j.freeradbiomed.2008.10.025"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.07.004"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1186\/1476-4598-9-137"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1186\/1476-4598-12-37"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12885-016-2362-6"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100155e"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm000164q"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2015.12.049"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phanu.2017.01.001"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.2174\/1570180811666140915222343"},{"key":"e_1_2_10_20_1","first-page":"42","volume":"21","author":"Hartmann Jomada D.","year":"2016","journal-title":"Molecules"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd.2018.46"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.plefa.2020.102142"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.4314\/tjpr.v13i2.22"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.162187599"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.03.005"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)47434-0"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-013-1503-3"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/np060252z"},{"key":"e_1_2_10_29_1","first-page":"1503","volume":"36","author":"Chee D. O.","year":"1976","journal-title":"Cancer Res."},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.35.10"},{"key":"e_1_2_10_31_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.11.151"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms16035014"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2018.10.022"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.2174\/0929867322666150716114758"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.05.093"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2017.06.005"},{"key":"e_1_2_10_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.7b00853"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.1186\/1471-2407-9-352"},{"key":"e_1_2_10_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2017.05.010"},{"key":"e_1_2_10_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1759(83)90303-4"}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202000709","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cmdc.202000709","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202000709","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:49:20Z","timestamp":1760273360000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.202000709"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,21]]},"references-count":41,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2021,3,18]]}},"alternative-id":["10.1002\/cmdc.202000709"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.202000709","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"value":"1860-7179","type":"print"},{"value":"1860-7187","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,21]]},"assertion":[{"value":"2020-09-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-01-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}