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Open AccessArticle

Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity

1
CIIMAR - Centro Interdisciplinar de Investigação Marinha e Ambiental, Terminal de Cruzeiros do Porto de Leixões, 4450-208 Matosinhos, Portugal
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Laboratório de Química Orgânica e Farmacêutica, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
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ICBAS – Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
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i3S – Instituto de Investigação e Inovação em Saúde, Rua Alfredo Allen 208, 4200-135 Porto, Portugal
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IBMC – Instituto de Biologia Molecular e Celular Universidade do Porto, Rua Alfredo Allen 208, 4200-135 Porto, Portugal
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Laboratório de Microbiologia, Departamento de Ciências Biológicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
*
Authors to whom correspondence should be addressed.
Correspondence:These authors contributed equally to this work.
Academic Editors: Cheng-Wei Tom Chang, Jon Y. Takemoto and Jixun Zhan
Molecules 2020, 25(10), 2405; https://doi.org/10.3390/molecules25102405
Received: 8 May 2020 / Revised: 15 May 2020 / Accepted: 17 May 2020 / Published: 21 May 2020
(This article belongs to the Special Issue Recent Advances in the Development of Antimicrobial Agents)
A series of thirteen xanthones 315 was prepared based on substitutional (appendage) diversity reactions. The series was structurally characterized based on their spectral data and HRMS, and the structures of xanthone derivatives 1, 7, and 8 were determined by single-crystal X-ray diffraction. This series, along with an in-house series of aminated xanthones 1633, was tested for in-vitro antimicrobial activity against seven bacterial (including two multidrug-resistant) strains and five fungal strains. 1-(Dibromomethyl)-3,4-dimethoxy-9H-xanthen-9-one (7) and 1-(dibromomethyl)-3,4,6-trimethoxy-9H-xanthen-9-one (8) exhibited antibacterial activity against all tested strains. In addition, 3,4-dihydroxy-1-methyl-9H-xanthen-9-one (3) revealed a potent inhibitory effect on the growth of dermatophyte clinical strains (T. rubrum FF5, M. canis FF1 and E. floccosum FF9), with a MIC of 16 µg/mL for all the tested strains. Compounds 3 and 26 showed a potent inhibitory effect on two C. albicans virulence factors: germ tube and biofilm formation. View Full-Text
Keywords: xanthones; diversity-oriented synthesis; antifungal activity; antibacterial activity xanthones; diversity-oriented synthesis; antifungal activity; antibacterial activity
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MDPI and ACS Style

Resende, D.I.S.P.; Pereira-Terra, P.; Moreira, J.; Freitas-Silva, J.; Lemos, A.; Gales, L.; Pinto, E.; de Sousa, M.E.; da Costa, P.M.; Pinto, M.M.M. Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity. Molecules 2020, 25, 2405.

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