1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester | 122949-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
• CAS: 122949-40-0
• 化学式: C₃₅H₃₈FN₅O₈S₂
• 分子量: 739.846
• InChiKey: VSVGBJUAQWFHSS-AKGWNBJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  51.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  147.56
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7S)-2-carboxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
  参考文献：
  名称：

  Cephalosporin 3'-quinolone esters with a dual mode of action

  摘要：

  According to the generally accepted mechanism by which bacterial enzymes react with cephalosporins, opening of the beta-lactam ring can lead to the expulsion of a 3'-substituent. A series of dual-action cephalosporins was prepared in which antibacterial quinolones were linked to the cephalosporin 3'-position through an ester bond in the expectation that, in addition to exerting their own beta-lactam activity, these cephalosporins would act as prodrugs for the second antibacterial agent. Compared to parent cephalosporins in which the 3'-substituent was acetoxy, the bifunctional cephalosporins exhibited a broadened antibacterial spectrum, suggesting that a dual mode of action may indeed be operative.

  DOI：

  10.1021/jm00163a013
• 作为产物：
  描述：

  <6R-(6α,7β)>-3-(iodomethyl)-7-<(2-thienylacetyl)amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid tert-butyl ester 、 Sodium; 1-ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以54.5%的产率得到1-Ethyl-6-fluoro-7-(4-formyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
  参考文献：
  名称：

  Cephalosporin 3'-quinolone esters with a dual mode of action

  摘要：

  According to the generally accepted mechanism by which bacterial enzymes react with cephalosporins, opening of the beta-lactam ring can lead to the expulsion of a 3'-substituent. A series of dual-action cephalosporins was prepared in which antibacterial quinolones were linked to the cephalosporin 3'-position through an ester bond in the expectation that, in addition to exerting their own beta-lactam activity, these cephalosporins would act as prodrugs for the second antibacterial agent. Compared to parent cephalosporins in which the 3'-substituent was acetoxy, the bifunctional cephalosporins exhibited a broadened antibacterial spectrum, suggesting that a dual mode of action may indeed be operative.

  DOI：

  10.1021/jm00163a013