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Direct diazo-transfer reaction on beta-lactam: synthesis and preliminary biological activities of 6-triazolylpenicillanic acids.


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.

SUBMITTER: Chen PC 

PROVIDER: S-EPMC2755539 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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Direct diazo-transfer reaction on beta-lactam: synthesis and preliminary biological activities of 6-triazolylpenicillanic acids.

Chen Po C PC   Wharton Rebekah E RE   Patel Pratiq A PA   Oyelere Adegboyega K AK  

Bioorganic & medicinal chemistry 20070825 23


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. ...[more]

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