phosphoric acid 2-((5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenyloxy)-3-hydroxypropyl ester dimethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: phosphoric acid 2-((5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenyloxy)-3-hydroxypropyl ester dimethyl ester
• 英文别名: [3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoxy]propyl] dimethyl phosphate
• 化学式: C₂₅H₄₅O₆P
• 分子量: 472.602
• InChiKey: BQPQVUYAOXLIAM-GKFVBPDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phosphoric acid 2-((5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenyloxy)-3-hydroxypropyl ester dimethyl ester 在 三甲基氯硅烷 、 sodium iodide 、 甲醇 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以39%的产率得到Phosphoric acid mono-{3-hydroxy-2-[((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenyl)oxy]-propyl} ester
  参考文献：
  名称：

  Synthesis, in Vitro Evaluation, and Intraocular Pressure Effects of Water-Soluble Prodrugs of Endocannabinoid Noladin Ether

  摘要：

  The poor aqueous solubility of 2-arachidonyl glyceryl ether (noladin ether) 2 hinders both pharmacological studies and pharmaceutical development. The synthesized mono- and diphosphate esters of noladin ether (4 and 6) considerably increased the aqueous solubility of noladin ether (> 40000-fold), showed high stability against chemical hydrolysis in buffer solutions, and were rapidly converted to the parent drug via enzymatic hydrolysis. The monophosphate ester of noladin ether reduced intraocular pressure in normotensive rabbits.

  DOI：

  10.1021/jm030877j
• 作为产物：
  描述：

  氯磷酸二甲酯 、 2-花生基甘油醚 在 吡啶 作用下， 以 乙醚 为溶剂， 以49%的产率得到phosphoric acid 2-((5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenyloxy)-3-hydroxypropyl ester dimethyl ester
  参考文献：
  名称：

  Synthesis, in Vitro Evaluation, and Intraocular Pressure Effects of Water-Soluble Prodrugs of Endocannabinoid Noladin Ether

  摘要：

  The poor aqueous solubility of 2-arachidonyl glyceryl ether (noladin ether) 2 hinders both pharmacological studies and pharmaceutical development. The synthesized mono- and diphosphate esters of noladin ether (4 and 6) considerably increased the aqueous solubility of noladin ether (> 40000-fold), showed high stability against chemical hydrolysis in buffer solutions, and were rapidly converted to the parent drug via enzymatic hydrolysis. The monophosphate ester of noladin ether reduced intraocular pressure in normotensive rabbits.

  DOI：

  10.1021/jm030877j