4-Cyanophenyl ethyl dodecylphosphonate | 1097617-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Cyanophenyl ethyl dodecylphosphonate
• 英文别名: 4-[dodecyl(ethoxy)phosphoryl]oxybenzonitrile
• CAS: 1097617-02-1
• 化学式: C₂₁H₃₄NO₃P
• 分子量: 379.48
• InChiKey: FHIBETIKXBGJPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[氯(乙氧基)磷基]十二烷 、 4-羟基苯甲腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以83%的产率得到4-Cyanophenyl ethyl dodecylphosphonate
  参考文献：
  名称：

  Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels

  摘要：

  The structure-activity relationships of organophosphorus (OP) and organosulfur compounds were examined in vitro and in vivo as inhibitors of mouse brain monoacylglycerol lipase (MAGL) hydrolysis of 2-arachidonoylglycerol (2-AG) and agonist binding at the CB1 receptor. Several compounds showed exceptional potency toward MAGL activity with IC50 values of 0.1-10 nM in vitro and high inhibition at 10 mg/kg intraperitoneally in mice. We find for the first time that MAGL activity is a major in vivo determinant of 2-AG and arachidonic acid levels not only in brain but also in spleen, lung, and liver. Apparent direct OP inhibition of CB1 agonist binding may be due instead to metabolic stabilization of 2-AG in brain membranes as the actual inhibitor. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.08.007

文献信息

• Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels
  作者：Daniel K. Nomura、Carolyn S.S. Hudak、Anna M. Ward、James J. Burston、Roger S. Issa、Karl J. Fisher、Mary E. Abood、Jenny L. Wiley、Aron H. Lichtman、John E. Casida

  DOI：10.1016/j.bmcl.2008.08.007

  日期：2008.11

  The structure-activity relationships of organophosphorus (OP) and organosulfur compounds were examined in vitro and in vivo as inhibitors of mouse brain monoacylglycerol lipase (MAGL) hydrolysis of 2-arachidonoylglycerol (2-AG) and agonist binding at the CB1 receptor. Several compounds showed exceptional potency toward MAGL activity with IC50 values of 0.1-10 nM in vitro and high inhibition at 10 mg/kg intraperitoneally in mice. We find for the first time that MAGL activity is a major in vivo determinant of 2-AG and arachidonic acid levels not only in brain but also in spleen, lung, and liver. Apparent direct OP inhibition of CB1 agonist binding may be due instead to metabolic stabilization of 2-AG in brain membranes as the actual inhibitor. Published by Elsevier Ltd.