STUDIES ON β-LACTAM ANTIBIOTICS

XIII. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 7β-[(Z)-2-ARYL-2-CARBOXYMETHOXYIMINOACETAMIDO]- 3-VINYLCEPHALOSPORINS

Abstract

The synthesis, antibacterial activity and oral absorption of the 7β-[(Z)-2-aryl-2-carboxymethoxyiminoacetamido]-3-vinylcephalosporins (1) are described. Of these cephalosporin derivatives (1), 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-carboxymethoxyiminoacetamido]-3-vinylcephalosporin (1a; FK027) exhibited the highest activity against Gram-negative bacteria and showed also good excretion after oral administration to rats. In addition, the effects on the antibacterial activity and oral absorption of the amino function on the thiazole ring are discussed.