7-{4-[Bis-(diethoxy-phosphoryl)-methyl]-piperazin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 434341-07-8

• 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: 7-{4-[Bis-(diethoxy-phosphoryl)-methyl]-piperazin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 7-[4-[Bis(diethoxyphosphoryl)methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 434341-07-8
• 化学式: C₂₆H₃₈FN₃O₉P₂
• 分子量: 617.548
• InChiKey: RVGHKHGPYXZSOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  7-{4-[Bis-(diethoxy-phosphoryl)-methyl]-piperazin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以95%的产率得到7-(4-(bis-phosphono-methyl)-piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrobromide
  参考文献：
  名称：

  Osteoadsorptive Bisphosphonate Derivatives of Fluoroquinolone Antibacterials

  摘要：

  Bisphosphonates conjugated to fluoroquinolone antibacterials through an intermediate carbon had better activity than conjugates lacking the carbon. Virtually all molar-based activity of these esterified bisphosphonate derivatives was identical to that of its parent. De-esterified free-acid forms retained good activity against most Gram-negative bacteria, but not against Gram-positives. A free-acid derivative remained bound to washed bone and completely inhibited Staphylococcus aureus growth. The more potent parent, ciprofloxacin, failed to bind significantly, and bacterial growth occurred.

  DOI：

  10.1021/jm0105326
• 作为产物：
  描述：

  二乙基亚磷酸氢酯 、 环丙沙星 、 原甲酸三乙酯 反应 0.5h， 以67%的产率得到7-{4-[Bis-(diethoxy-phosphoryl)-methyl]-piperazin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Osteoadsorptive Bisphosphonate Derivatives of Fluoroquinolone Antibacterials

  摘要：

  Bisphosphonates conjugated to fluoroquinolone antibacterials through an intermediate carbon had better activity than conjugates lacking the carbon. Virtually all molar-based activity of these esterified bisphosphonate derivatives was identical to that of its parent. De-esterified free-acid forms retained good activity against most Gram-negative bacteria, but not against Gram-positives. A free-acid derivative remained bound to washed bone and completely inhibited Staphylococcus aureus growth. The more potent parent, ciprofloxacin, failed to bind significantly, and bacterial growth occurred.

  DOI：

  10.1021/jm0105326

文献信息

• Osteoadsorptive Bisphosphonate Derivatives of Fluoroquinolone Antibacterials
  作者：Pál Herczegh、Thomas B. Buxton、James C. McPherson、Árpád Kovács-Kulyassa、Phyllis D. Brewer、Ferenc Sztaricskai、Gary G. Stroebel、Kent M. Plowman、Dan Farcasiu、John F. Hartmann

  DOI：10.1021/jm0105326

  日期：2002.5.1

  Bisphosphonates conjugated to fluoroquinolone antibacterials through an intermediate carbon had better activity than conjugates lacking the carbon. Virtually all molar-based activity of these esterified bisphosphonate derivatives was identical to that of its parent. De-esterified free-acid forms retained good activity against most Gram-negative bacteria, but not against Gram-positives. A free-acid derivative remained bound to washed bone and completely inhibited Staphylococcus aureus growth. The more potent parent, ciprofloxacin, failed to bind significantly, and bacterial growth occurred.