title: 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.
abstract: 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.
authors.forename: C
authors.initials: C
authors.lastname: Yoshida
authors.forename: K
authors.initials: K
authors.lastname: Tanaka
authors.forename: Y
authors.initials: Y
authors.lastname: Todo
authors.forename: R
authors.initials: R
authors.lastname: Hattori
authors.forename: Y
authors.initials: Y
authors.lastname: Fukuoka
authors.forename: M
authors.initials: M
authors.lastname: Komatsu
authors.forename: I
authors.initials: I
authors.lastname: Saikawa
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D047090:beta-Lactams