1-{4-[bis(diethoxyphosphoryl)methyl]phenyl}-1,4-dihydro-4-oxoquinoline-3-carboxylic ethyl ester | 389056-63-7

• 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: 1-{4-[bis(diethoxyphosphoryl)methyl]phenyl}-1,4-dihydro-4-oxoquinoline-3-carboxylic ethyl ester
• 英文别名: ethyl 1-[4-[bis(diethoxyphosphoryl)methyl]phenyl]-4-oxoquinoline-3-carboxylate
• CAS: 389056-63-7
• 化学式: C₂₇H₃₅NO₉P₂
• 分子量: 579.524
• InChiKey: GRTQWNKCCUGSQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  119.36
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-{4-[bis(diethoxyphosphoryl)methyl]phenyl}-1,4-dihydro-4-oxoquinoline-3-carboxylic ethyl ester 在 三甲基溴硅烷 、 硫酸 、 溶剂黄146 作用下， 以 氯仿 、 水 为溶剂， 反应 4.5h， 生成 1-[4-(bisphosphonomethyl)pheny]-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
• 作为产物：
  描述：

  2-(2-fluorobenzoyl)-3-ethoxyacrylic ethyl ester 在 sodium fluoride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-{4-[bis(diethoxyphosphoryl)methyl]phenyl}-1,4-dihydro-4-oxoquinoline-3-carboxylic ethyl ester
  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