{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,19]],"date-time":"2026-02-19T05:06:26Z","timestamp":1771477586989,"version":"3.50.1"},"reference-count":57,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2020,9,3]],"date-time":"2020-09-03T00:00:00Z","timestamp":1599091200000},"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":["ChemistrySelect"],"published-print":{"date-parts":[[2020,9,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A new series of thirty\u2010two new enantiomerically pure derivatives of xanthones (\n                    <jats:bold>3<\/jats:bold>\n                    \u2013\n                    <jats:bold>34<\/jats:bold>\n                    ) were synthesized for antitumor evaluation. Two carboxyxanthones (\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    ) were used as chemical substrates and coupled with selected chiral building blocks (\n                    <jats:bold>43<\/jats:bold>\n                    \u2013\n                    <jats:bold>62<\/jats:bold>\n                    ), achieving yields and enantiomeric excess (ee) values higher than 92 and 99\u2009%, respectively. Carboxyxanthones\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    were synthesized, by a multi\u2010step synthetic pathway\n                    <jats:italic>via<\/jats:italic>\n                    diaryl ether intermediate (Ullman reaction), being compound\n                    <jats:bold>2<\/jats:bold>\n                    described here for the first time. The evaluation of the growth inhibitory activity allowed to find active chiral compounds for all the tested cells lines, and to establish structure\u2010activity relationship (SAR) considerations. In some cases, the growth inhibitory effects demonstrated to be dependent on the stereochemistry of the compounds. Interestingly, the most active compound (\n                    <jats:bold>12<\/jats:bold>\n                    ) and its enantiomer (\n                    <jats:bold>11<\/jats:bold>\n                    ) demonstrated high enantioselectivity for MCF\u20107 breast adenocarcinoma cell line. In addition,\n                    <jats:italic>in\u2005vitro<\/jats:italic>\n                    DNA crosslinking ability was assessed and the results correlated with\n                    <jats:italic>in\u2005vitro<\/jats:italic>\n                    cytotoxicity.\n                  <\/jats:p>","DOI":"10.1002\/slct.202002588","type":"journal-article","created":{"date-parts":[[2020,9,3]],"date-time":"2020-09-03T07:21:31Z","timestamp":1599117691000},"page":"10285-10291","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Synthesis of New Chiral Derivatives of Xanthones with Enantioselective Effect on Tumor Cell Growth and DNA Crosslinking"],"prefix":"10.1002","volume":"5","author":[{"given":"Maria L.","family":"Carraro","sequence":"first","affiliation":[{"name":"Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto  Rua de Jorge Viterbo Ferreira 228 4050-313 Porto Portugal"}]},{"given":"Sandra","family":"Marques","sequence":"additional","affiliation":[{"name":"CESPU Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade (IINFACTS)  Rua Central de Gandra, 1317 4585-116 Gandra PRD Portugal"}]},{"given":"Ana Sofia","family":"Silva","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto  Rua de Jorge Viterbo Ferreira 228 4050-313 Porto Portugal"}]},{"given":"Bruno","family":"Freitas","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto  Rua de Jorge Viterbo Ferreira 228 4050-313 Porto Portugal"}]},{"given":"Patr\u00edcia M. A.","family":"Silva","sequence":"additional","affiliation":[{"name":"CESPU Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade (IINFACTS)  Rua Central de Gandra, 1317 4585-116 Gandra PRD Portugal"}]},{"given":"Joel","family":"Pedrosa","sequence":"additional","affiliation":[{"name":"CESPU Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade (IINFACTS)  Rua Central de Gandra, 1317 4585-116 Gandra PRD Portugal"}]},{"given":"Paolo","family":"De Marco","sequence":"additional","affiliation":[{"name":"CESPU Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade (IINFACTS)  Rua Central de Gandra, 1317 4585-116 Gandra PRD Portugal"}]},{"given":"Hassan","family":"Bousbaa","sequence":"additional","affiliation":[{"name":"CESPU Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade (IINFACTS)  Rua Central de Gandra, 1317 4585-116 Gandra PRD Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR) Edif\u00edcio do Terminal de Cruzeiros do  Porto de Leix\u00f5es Av. General Norton de Matos s\/n 4050-208 Matosinhos Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0940-9163","authenticated-orcid":false,"given":"Carla","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto  Rua de Jorge Viterbo Ferreira 228 4050-313 Porto Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR) Edif\u00edcio do Terminal de Cruzeiros do  Porto de Leix\u00f5es Av. 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