Synthesis and antibacterial activity of 2-(isoxazolidinio-5-yl)carbapenem derivatives.
The synthesis and antibacterial activity of the title compounds having an isoxazolidine ring at the C-2 position are described. These derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of nitrone with 2-vinyl carbapenems. This 1,3-dipolar cycloaddition reaction proceeded regioselectively to give diastereomeric isomers of 2(-isoxazolidin-5-yl)carbapenems. It was ascertained that the antibacterial activity of 1 beta-methylcarbapenem derivatives was superior to that of the corresponding 1H-carbapenem derivatives, and between the 2-(isoxazolidin-5-yl)-1 beta-methylcarbapenems the antibacterial activity of the 5'R-isomer was slightly better than that of the 5' R-isomer slightly better than that of the 5' S-isomer.
Nishi
K
K
Shionogi Research Laboratories, Shionogi & Co, Ltd, Osaka, Japan.
Imuta
M
M
Kimura
Y
Y
Miwa
H
H
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D015780:Carbapenems; D007555:Isoxazoles