tert-butyl 4-(3-(chlorocarbonyl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazine-1-carboxylate | 1369321-13-0

• 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: tert-butyl 4-(3-(chlorocarbonyl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazine-1-carboxylate
• CAS: 1369321-13-0
• 化学式: C₂₁H₂₅ClFN₃O₄
• 分子量: 437.899
• InChiKey: CWWJANCIKOJAQX-UHFFFAOYSA-N

物化性质

• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  71.85
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,3-双棕榈酸甘油酯 、 tert-butyl 4-(3-(chlorocarbonyl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazine-1-carboxylate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以75%的产率得到2-((7-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbonyl)oxy)propane-1,3-diyl dipalmitate
  参考文献：
  名称：

  Diglyceride prodrug strategy for enhancing the bioavailability of norfloxacin

  摘要：

  Prodrug approach using diglyceride as a promoiety is a promising strategy to improve bioavailability of poorly absorbed drugs and the same was explored in the present work to improve oral bioavailability of norfloxacin: a second generation fluoroquinolone antibacterial. The prodrug was synthesized by standard procedures using dipalmitine as a carrier and the structure was confirmed by spectral analysis. Higher Log P indicated improved lipophilicity. The ester linkage between norfloxacin and dipalmitine would be susceptible to hydrolysis by lipases to release the parent drug and carrier in the body. In vivo kinetic studies in rats indicated 53% release of norfloxacin in plasma at the end of 8 h. The prodrug exhibited improved pharmacological profile than the parent compound at equimolar dose that indirectly indicated improved bioavailability. (C) 2011 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2011.03.006
• 作为产物：
  描述：

  7-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 五氯化磷 作用下， 反应 0.5h， 以95%的产率得到tert-butyl 4-(3-(chlorocarbonyl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Diglyceride prodrug strategy for enhancing the bioavailability of norfloxacin

  摘要：

  Prodrug approach using diglyceride as a promoiety is a promising strategy to improve bioavailability of poorly absorbed drugs and the same was explored in the present work to improve oral bioavailability of norfloxacin: a second generation fluoroquinolone antibacterial. The prodrug was synthesized by standard procedures using dipalmitine as a carrier and the structure was confirmed by spectral analysis. Higher Log P indicated improved lipophilicity. The ester linkage between norfloxacin and dipalmitine would be susceptible to hydrolysis by lipases to release the parent drug and carrier in the body. In vivo kinetic studies in rats indicated 53% release of norfloxacin in plasma at the end of 8 h. The prodrug exhibited improved pharmacological profile than the parent compound at equimolar dose that indirectly indicated improved bioavailability. (C) 2011 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2011.03.006