1-Ethyl-6-fluoro-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-4-oxy-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 118376-55-9

• 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-Ethyl-6-fluoro-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-4-oxy-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 1-ethyl-6-fluoro-7-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-4-oxidopiperazin-4-ium-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 118376-55-9
• 化学式: C₂₁H₂₂FN₃O₇
• 分子量: 447.42
• InChiKey: XXNMCRAQGNZKHP-UHFFFAOYSA-N

物化性质

• 熔点：
  138-144 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  128.95
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-Ethyl-6-fluoro-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-4-oxy-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 以 氯仿 为溶剂， 反应 0.33h， 以97.5%的产率得到N-((4-甲基-5-亚甲基-2-氧代-1,3-二氧戊环-4-基)氧基)诺氟沙星
  参考文献：
  名称：

  Studies on prodrugs. 11. Synthesis and antimicrobial activity of N-[(4-methyl-5-methylene-2-oxo-1,3-dioxolan-4-yl)oxy]norfloxacin

  摘要：

  The chemical oxidation of N-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl] norfloxacin (2) was carried out to afford N-[(4-methyl-5-methylene-2-oxo-1,3-dioxolan-4-yl)oxy]norfloxacin (4). In vitro, 4 exhibited lower activity than that of norfloxacin (NFLX, 1) for both Gram-positive and Gram-negative bacteria. However, in vivo the activity of 4 was higher than that of NFLX. Bioavailability studies in mice showed that 4 liberated a higher concentration of NFLX in plasma than NFLX itself when administered orally. From these data, 4 obtained by the chemical oxidation of 2 functioned as a prodrug of NFLX as well as did 2. The mechanism of the formation of 4 is interpreted in terms of [2,3]-sigmatropic rearrangement.

  DOI：

  10.1021/jm00123a029
• 作为产物：
  描述：

  N-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl NFLX 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.5h， 以88%的产率得到1-Ethyl-6-fluoro-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-4-oxy-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Studies on prodrugs. 11. Synthesis and antimicrobial activity of N-[(4-methyl-5-methylene-2-oxo-1,3-dioxolan-4-yl)oxy]norfloxacin

  摘要：

  The chemical oxidation of N-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl] norfloxacin (2) was carried out to afford N-[(4-methyl-5-methylene-2-oxo-1,3-dioxolan-4-yl)oxy]norfloxacin (4). In vitro, 4 exhibited lower activity than that of norfloxacin (NFLX, 1) for both Gram-positive and Gram-negative bacteria. However, in vivo the activity of 4 was higher than that of NFLX. Bioavailability studies in mice showed that 4 liberated a higher concentration of NFLX in plasma than NFLX itself when administered orally. From these data, 4 obtained by the chemical oxidation of 2 functioned as a prodrug of NFLX as well as did 2. The mechanism of the formation of 4 is interpreted in terms of [2,3]-sigmatropic rearrangement.

  DOI：

  10.1021/jm00123a029

文献信息

• KONDO, HIROSATO;SAKAMOTO, FUMIO;UNO, TOSHIO;KAWAHATA, YOSHIHIRO;TSUKAMOTO+, J. MED. CHEM., 32,(1989) N, C. 671-674
  作者：KONDO, HIROSATO、SAKAMOTO, FUMIO、UNO, TOSHIO、KAWAHATA, YOSHIHIRO、TSUKAMOTO+

  DOI：——

  日期：——