(6R)-trans-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<<<<4-<1-cyclopropyl-6-fluoro-1,4-dihydro-3-<<(4-nitrophenyl)methoxy>carbonyl>-4-oxo-7-quinolinyl>-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphe | 127142-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6R)-trans-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<<<<4-<1-cyclopropyl-6-fluoro-1,4-dihydro-3-<<(4-nitrophenyl)methoxy>carbonyl>-4-oxo-7-quinolinyl>-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphe
• CAS: 127142-84-1
• 化学式: C₅₀H₄₇FN₆O₁₂S
• 分子量: 975.021
• InChiKey: DJLRYZQYGUDUFT-KUKXATSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  70.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  209.16
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (6R)-trans-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<<<<4-<1-cyclopropyl-6-fluoro-1,4-dihydro-3-<<(4-nitrophenyl)methoxy>carbonyl>-4-oxo-7-quinolinyl>-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphe 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以70.4%的产率得到(6R)-trans-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-7-<<(1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates

  摘要：

  A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities.

  DOI：

  10.1021/jm00113a026
• 作为产物：
  描述：

  (6R)-trans-3-(hydroxymethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenyl methyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.67h， 生成 (6R)-trans-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<<<<4-<1-cyclopropyl-6-fluoro-1,4-dihydro-3-<<(4-nitrophenyl)methoxy>carbonyl>-4-oxo-7-quinolinyl>-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphe
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates

  摘要：

  A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities.

  DOI：

  10.1021/jm00113a026