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Bioorg Med Chem Lett. 2011 Dec 1;21(23):7085-8. doi: 10.1016/j.bmcl.2011.09.088. Epub 2011 Oct 1.

The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity.

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Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Box Wits 2050, South Africa.


Exposure of the phenol, (5-bromo-2-hydroxyphenyl)(2,4,5-trimethoxyphenyl)methanone 18 to ceric ammonium nitrate (CAN) resulted in the formation of 7-bromo-3,4a-dimethoxy-2H-xanthene-2,9(4aH)-dione 19 and 5-bromo-2',5'-dimethoxy-3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione 20. The brominated spirobenzofuran 20 was then subjected to Suzuki-Miyaura reactions to give six derivatives 22a-f. These compounds, related diones and xanthones displayed mostly noteworthy antimicrobial activity, particularly towards the yeasts Cryptococcus neoformans and Candida albicans. Diones 15 and 30 displayed significant activity (7.8 μg/mL) against C. albicans and C. neoformans, respectively. Furthermore, dione 10 displayed the most significant activity (3.6 μg/mL) against both yeasts.

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