Studies on monocyclic beta-lactam antibiotics. IV. Synthesis and antibacterial activity of (3S,4R)-3-[2-(2-aminothiazol-4-yl)-(Z)-2-(O-substituted oxyimino)acetamido]-4-methyl-1- (1H-tetrazol-5-yl)-2-azetidinones.
The synthesis and in vitro activity of the 3-(O-substituted oxyiminoacetamido)-2-azetidinones (IV) possessing a tetrazole moiety at N-1 position are described. The introduction of lipophilic functions into the oxyimino moiety gave in some good activity against staphylococci, but decreased activity against Gram-negative bacteria. In contrast, the introduction of hydrophilic functions such as carboxycyclobutane resulted in strong activity against Gram-negative bacteria including Pseudomonas aeruginosa, and no or very small activity against the staphylococci.
Yoshida
C
C
Tanaka
K
K
Todo
Y
Y
Hattori
R
R
Fukuoka
Y
Y
Komatsu
M
M
Saikawa
I
I
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013329:Structure-Activity Relationship; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D047090:beta-Lactams