Abstract
In this study we report the first example of a direct diazo-transfer reaction on readily available 6-aminopenicillanates to give 6-azidopenicillanates in high yield. Subsequent Cu(I)-catalyzed Huisgen cycloaddition between these 6-azidopenicillanates and assorted terminal alkynes facilely furnished 6-triazolylpenicillanic acids. Preliminary biological screening indicates that these triazolylpenicillanic acids possess low to moderate antibacterial activities.
Publication types
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Research Support, N.I.H., Extramural
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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Azides / chemistry*
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Bacillus anthracis / drug effects*
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Catalysis
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Copper / chemistry
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Cyclization
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Escherichia coli / drug effects*
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Microbial Sensitivity Tests
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Molecular Conformation
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Penicillanic Acid / analogs & derivatives
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Penicillanic Acid / chemical synthesis*
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Penicillanic Acid / pharmacology
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Staphylococcus aureus / drug effects*
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Stereoisomerism
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Streptococcus pneumoniae / drug effects*
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Structure-Activity Relationship
Substances
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Anti-Bacterial Agents
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Azides
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Copper
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Penicillanic Acid