Monocyclic antibiotic beta-lactams.
The preparation and antimicrobial activity of a series of beta-lactams (3a-f) are described. These compounds were prepared from the 2+2 cycloaddition of beta,beta-disubstituted enamines with aryl isocyanates; compounds 3a-f underwent facile beta-lactam ring fission between aminal carbon atom C4 and the lactam nitrogen N1. The resisting formylacetanilide derivatives were devoid of antibiotic activity.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001884:Bordetella / Q000187:drug effects; D013293:Enterococcus faecalis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D013210:Staphylococcus / Q000187:drug effects; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D047090:beta-Lactams