6,8-Difluoro-1-(2-fluoro-ethyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-7-formylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester | 122949-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6,8-Difluoro-1-(2-fluoro-ethyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-7-formylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
• 英文别名: tert-butyl (6R,7R)-3-[[6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carbonyl]oxymethyl]-7-formamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 122949-41-1
• 化学式: C₃₀H₃₄F₃N₅O₇S
• 分子量: 665.69
• InChiKey: WWPMPNZJTFPQAF-JIPXPUAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  6,8-Difluoro-1-(2-fluoro-ethyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-7-formylamino-8-oxo-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 6,8-Difluoro-1-(2-fluoro-ethyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 2-carboxy-7-formylamino-8-oxo-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-trans)-7-(formylamino)-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid tert-butyl ester 、 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid potassium salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以18%的产率得到6,8-Difluoro-1-(2-fluoro-ethyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6R,7R)-2-tert-butoxycarbonyl-7-formylamino-8-oxo-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

文献信息

• ALBRECHT, HARRY A.;BESKID, GEORGE;CHAN, KA-KONG;CHRISTENSON, JAMES G.;CLE+, J. MED. CHEM., 33,(1990) N, C. 77-86
  作者：ALBRECHT, HARRY A.、BESKID, GEORGE、CHAN, KA-KONG、CHRISTENSON, JAMES G.、CLE+

  DOI：——

  日期：——