7-{4-[2,2-bis(phosphono)ethyl]piperacin-1-yl}-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

• 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-[2,2-bis(phosphono)ethyl]piperacin-1-yl}-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 7-[4-(2,2-Diphosphonoethyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• 化学式: C₁₈H₂₄FN₃O₉P₂
• 分子量: 507.349
• InChiKey: JMZVBDZZIZLTNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  179
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  7-(4-(2,2-bis-(diethoxy-phosphoryl)-ethyl)-piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 三甲基溴硅烷 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以92%的产率得到7-{4-[2,2-bis(phosphono)ethyl]piperacin-1-yl}-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  QUINOLONE ANTIBACTERIAL AGENTS LINKED TO OSTEOTROPIC BISPHOSPHONATE MOIETIES

  摘要：

  Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.

  DOI：

  10.1080/10426500108040581

文献信息

• DIPHOSPHONATE DERIVATIVES OF THERAPEUTIC AGENTS
  申请人：ElizaNor Biopharmaceuticals, Inc.

  公开号：EP0831869B1

  公开（公告）日：2006-02-08
• QUINOLONE ANTIBACTERIAL AGENTS LINKED TO OSTEOTROPIC BISPHOSPHONATE MOIETIES
  作者：T. Pieper、B. K. Keppler

  DOI：10.1080/10426500108040581

  日期：2001.3.1

  Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.