Journal
MOLECULES
Volume 23, Issue 10, Pages -Publisher
MDPI
DOI: 10.3390/molecules23102617
Keywords
xanthones; synthesis; chlorination; antifungal activity; antibacterial activity
Funding
- FCT/MCTES-Foundation for Science and Technology from the Ministry of Science, Technology, and Higher Education (PIDDAC)
- European Regional Development Fund (ERDF) through the COMPETE-Programa Operacional Factores de Competitividade (POFC) programme [UID/Multi/04423/2013]
- programme PT2020 [POCI-01-0145-FEDER-028736, POCI-01-0145-FEDER-016790 (PTDC/MAR-BIO/4694/2014
- 3599-PPCDT)]
- project INNOVMAR-Innovation and Sustainability in the Management and Exploitation of Marine Resources [NORTE-01-0145-FEDER-000035]
- North Portugal Regional Operational Programme (NORTE 2020) under the PORTUGAL 2020 Partnership Agreement through the European Regional Development Fund (ERDF)
- [NOVELMAR/BPD_2/2016-019]
- [NOVELMAR/BPD/2017/012]
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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 mu g/mL)). Moreover, when evaluated for its synergistic effect for T. rubrum, compound 18 exhibited synergy with fluconazole (Sigma FIC = 0.289). These results disclosed new hit xanthones for both antibacterial and antifungal activity.
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