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Open AccessArticle

Lichen Xanthones as Models for New Antifungal Agents

1
Laboratory of Organic and Pharmaceutical Chemistry (LQOF), Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal
3
Laboratory of Microbiology, Department of Aquatic Production, Institute of Biomedical Sciences Abel Salazar (ICBAS), University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
4
Laboratory of Microbiology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2018, 23(10), 2617; https://doi.org/10.3390/molecules23102617
Received: 20 September 2018 / Revised: 4 October 2018 / Accepted: 9 October 2018 / Published: 12 October 2018
Due to the emergence of multidrug-resistant pathogenic microorganisms, the search for new antimicrobial compounds plays an important role in current medicinal chemistry research. Inspired by lichen antimicrobial xanthones, a series of novel chlorinated xanthones was prepared using five chlorination methods (Methods A–E) to obtain different patterns of substitution in the xanthone scaffold. All the synthesized compounds were evaluated for their antimicrobial activity. Among them, 3-chloro-4,6-dimethoxy-1-methyl-9H-xanthen-9-one 15 showed promising antibacterial activity against E. faecalis (ATCC 29212 and 29213) and S. aureus ATCC 29213. 2,7-Dichloro-3,4,6-trimethoxy-1-methyl-9H-xanthen-9-one 18 revealed a potent fungistatic and fungicidal activity against dermatophytes clinical strains (T. rubrum, M. canis, and E. floccosum (MIC = 4–8 µg/mL)). Moreover, when evaluated for its synergistic effect for T. rubrum, compound 18 exhibited synergy with fluconazole (ΣFIC = 0.289). These results disclosed new hit xanthones for both antibacterial and antifungal activity. View Full-Text
Keywords: xanthones; synthesis; chlorination; antifungal activity; antibacterial activity xanthones; synthesis; chlorination; antifungal activity; antibacterial activity
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Resende, D.I.S.P.; Pereira-Terra, P.; Inácio, Â.S.; Costa, P.M.; Pinto, E.; Sousa, E.; Pinto, M.M.M. Lichen Xanthones as Models for New Antifungal Agents. Molecules 2018, 23, 2617.

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