Synthetic Cephalosporins. III. Synthesis and Antibacterial Activity of 7-[2-(2-Aminothiazol-4-yl)-3-carboxy-2-propenoamido] cephalosporins and Related Compounds

Abstract

Synthesis and antibacterial activity of 7-[2-(2-aminothiazol-4-yl)-3-carboxy-2-propenoamido] cephalosporins and their derivatives are described. These compounds are of interest as carbon analogues of oximecephalosporins, 7-[2-(2-aminothiazol-4-yl)-2 (Z)-oxyiminoacetamido] cephalosporins having remarkable antibacterial activity. The synthesized 7-[2-(2-aminothiazol-4-yl)-3(Z)-carboxy-2-propenoamido]-cephalosporins (14, 19) show improved activity especially against the β-lactamase-producing strains. A 7-[2-(2-aminothiazol-4-yl) maleimido] cephalosporin (15) has been also prepared by cyclization of 7-[3-(2-aminothiazol-4-yl)-2-ethoxycarbonyl-2 (Z)-propenoamido] cephalosporin.