Abstract
Unciaphenol (2), an oxygenated analogue of the Bergman cyclization product of the enediyne uncialamycin (1), has been isolated along with 1 from cultures of the actinomycete Streptomyces uncialis. It is proposed that the C-22 OH substituent in 2 might arise from the attack of a nucleophilic oxygen species on the p-benzyne diradical intermediate IA in the Bergman cyclization of 1. 2 shows in vitro anti-HIV activity against viral strains that are resistant to clinically utilized anti-retroviral therapies.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anthraquinones / chemistry
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Anthraquinones / isolation & purification*
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Anthraquinones / pharmacology*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification*
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Anti-Bacterial Agents / pharmacology*
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / isolation & purification*
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Anti-HIV Agents / pharmacology*
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Biological Products / chemistry
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Biological Products / isolation & purification*
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Biological Products / pharmacology*
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Cyclization
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Drug Resistance, Viral
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Microbial Sensitivity Tests
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
Substances
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Anthraquinones
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Anti-Bacterial Agents
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Anti-HIV Agents
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Biological Products
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uncialamycin
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unciaphenol