Synthesis and antibacterial activity of cephalosporins having a catechol in the C3 side chain.
Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4- ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-1-propen-1-yl]cephalospo rin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia.
Okita
T
T
Birstol-Myers Squibb Research Institute, Tokyo, Japan.
Imae
K
K
Hasegawa
T
T
Iimura
S
S
Masuyoshi
S
S
Kamachi
H
H
Kamei
H
H
D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
D002511:Cephalosporins; C081745:7-(2- (2-aminothiazol-4-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido)-3-(3,4-dihydroxybenzoyloxy)methyl-3-cephem-4-carboxylic acid; C081744:7-(2-(2-aminothiazol-4-yl)- 2-(1-carboxyl-1-methylethoxyimino)acetamido)-3-(3-(3,4-dihydroxybenzoyloxy)-1-propen-1-yl)-3-cephem-4-carboxylic acid