Direct diazo-transfer reaction on beta-lactam: synthesis and preliminary biological activities of 6-triazolylpenicillanic acids.
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.
Chen
Po C
PC
School of Chemistry and Biochemistry, Parker H. Petit Institute for Bioengineering and Biosciences, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA.
Wharton
Rebekah E
RE
Patel
Pratiq A
PA
Oyelere
Adegboyega K
AK
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry*; D001408:Bacillus anthracis / Q000187:drug effects*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D004926:Escherichia coli / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010397:Penicillanic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects*; D013237:Stereoisomerism; D013296:Streptococcus pneumoniae / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D001386:Azides; D003300:Copper; D010397:Penicillanic Acid