Abstract
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.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Antifungal Agents / chemical synthesis
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Benzofurans / pharmacology*
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Benzoquinones / chemical synthesis
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Benzoquinones / chemistry
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Benzoquinones / pharmacology
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Candida albicans / drug effects*
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Cryptococcus neoformans / drug effects*
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Molecular Structure
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Spiro Compounds / pharmacology*
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Xanthones / chemical synthesis*
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Xanthones / chemistry
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Xanthones / pharmacology*
Substances
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Anti-Bacterial Agents
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Antifungal Agents
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Benzofurans
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Benzoquinones
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Spiro Compounds
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Xanthones
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spirobenzofuran