세팔로스포린 3''-퀴놀론의 합성 및 항균작용

Synthesis and Antibacterial Activity of Cephalosporin 3''-Quinolone Dithiocarbamate

To a suspension of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-{3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl}-4-oxo-3-quinoline carboxylic acid(C1) in sodium hydroxide solution and water is added dropwise with stirring carbon disulfide. [6R-[6alpha, 7beta(Z)]]-7-[[[(2-Amino-4-thiazoly)methoxyimino]-acetyl]amino]-3-[[[[7-(3-carboxy-1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxo-7-guinolonyl)-3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]thioxomethyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (DACD) was synthesized from 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[7-(mercapto)thioxomethyl-{3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl}]-4-oxo-3-quinoline carboxylic acid disodium salt(C2) and cefotaxime. The in vitro activity of novel dual-action cephalosporin, DACD, was compared with the in vitro activities of CENO(cefotaxime 3''-norfloxacin dithiocarbamate), cefotaxime, and norfloxacin against a variety of bacterial species. In vitro activity of DACD was superior to that of norfloxacin against Streptococcus pyogenes. Against Gram-positive and Gram-negative bacteria, its activity was almost equal to that of CENO.