Studies on monocyclic beta-lactam antibiotics. II. Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-oxysulfonic acids.
The synthesis and in vitro antibacterial and beta-lactamase inhibitory activity of the 2-azetidinone-1-oxysulfonic acids having a substituent at C-4 position of the beta-lactam ring are described. The influence of C-4 substituents on the antibacterial activity was examined for the compounds having alpha-ureidoacetyl or alpha-oxyiminoacetyl group as acyl side chain at C-3 position. The antibacterial activity is correlated with the C-4 substituents and acyl side chain. Especially, 4(R)-methyl substituted derivatives exhibited excellent activity against Gram-negative bacteria and 4-dimethyl substituted derivatives exhibited strong activity against resistant Gram-negative bacteria except for Pseudomonas aeruginosa. 39 and 40 showed strong inhibitory activity against cephalosporinase of Enterobacter cloacae H-27.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D047090:beta-Lactams
D000900:Anti-Bacterial Agents; D047090:beta-Lactams