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Yicathins B and C are two marine\u2010derived xanthones that have shown antibacterial and antifungal activity. Herein, the total synthesis of these yicathins and six novel analogues is reported for the first time. As marine natural products tend to have very lipophilic scaffolds, the lipophilicity of yicathins and their analogues was evaluated in the classical octanol\/water system and a biomimetic model\u2010based system. As the xanthonic nucleus is a \u201cprivileged structure\u201d, other biological activities were evaluated, namely antitumor and anti\u2010inflammatory activities. An interesting anti\u2010inflammatory activity was identified for yicathin analogues that paves the way for the design of dual activity (anti\u2010infective and anti\u2010inflammatory) marine\u2010inspired xanthone derivatives.<\/jats:p>","DOI":"10.1002\/cmdc.201900735","type":"journal-article","created":{"date-parts":[[2020,3,11]],"date-time":"2020-03-11T22:52:06Z","timestamp":1583967126000},"page":"749-755","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities"],"prefix":"10.1002","volume":"15","author":[{"given":"Daniela R. 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General Norton de Matos s\/n 4050-208 Matosinhos Porto Portugal"}]},{"given":"\u00c1lvaro F.","family":"Magalh\u00e3es","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":"Jos\u00e9 X.","family":"Soares","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE Department of Chemical Sciences Faculty of Pharmacy University of Porto  Rua de Jorge Viterbo Ferreira 228 4050-313 Porto Portugal"}]},{"given":"Joana","family":"Pinto","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":"Carlos M. 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