Synthesis and antibacterial activity of 2-(isoxazolidinio-5-yl)carbapenem derivatives

Article abstract of DOI:10.7164/antibiotics.48.1481

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 1β-methylcarbapenem derivatives was superior to that of the corresponding 1H-carbapenem derivatives, and between the 2-(isoxazolidin-5-yl)-1β-methylcarbapenems the antibacterial activity of the 5'R-isomer was slightly better than that of the 5'S-isomer.