(R)-glyceryl-thiophosphate-bis-(2-cyanoethyl)-ester | 645408-58-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: (R)-glyceryl-thiophosphate-bis-(2-cyanoethyl)-ester
• 英文别名: 3-[2-cyanoethoxy-[(2R)-2,3-dihydroxypropoxy]phosphinothioyl]oxypropanenitrile
• CAS: 645408-58-8
• 化学式: C₉H₁₅N₂O₅PS
• 分子量: 294.268
• InChiKey: OXTCTTCQGYAVBL-SECBINFHSA-N

物化性质

• 沸点：
  537.1±60.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-glyceryl-thiophosphate-bis-(2-cyanoethyl)-ester 在 2,4,6-三甲基吡啶 、 tetrafluoroboric acid 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-O-bis-(2-cyano-ethoxy)-thiophosphoryl-1-O-oleoyl-2(R)-O-methyl-sn-glycerol
  参考文献：
  名称：

  Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA₃ Receptor-Selective Agonist Activity

  摘要：

  The metabolically stabilized LPA analogue, 1-ole-oyl-2-O-methyl-rae-glycerophosphothioate (OMPT), is a potent agonist for the LPA(3) G-protein-coupled receptor. A new enantiospecific synthesis of both (2R)-OMPT and (2S)-OMPT is described. Calcium release assays in both LPA(3)-transfected insect Sf9 and rat hepatoma Rh7777 cells showed that (2S)OMPT was 5- to 20-fold more active than (2R)-OMPT. Similar results were found for calcium release, MAPK and Akt activation, and IL-6 release in human OVCAR3 ovarian cancer cells.

  DOI：

  10.1021/jm034207p
• 作为产物：
  描述：

  双(2-氰乙基)-N,N-二异丙基亚磷酰胺 在 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 Dowex 50W (H+) 作用下， 以 甲醇 、 二硫化碳 、 二氯甲烷 为溶剂， 生成 (R)-glyceryl-thiophosphate-bis-(2-cyanoethyl)-ester
  参考文献：
  名称：

  Synthesis of (R)-lysothiophosphatidic Acid and (R)-thiophosphatidic acid

  摘要：

  (R)-Thiophosphatidic acid and (R)-lysothiophosphatidic acid were obtained in an efficient synthesis from a chiral glycerol precursor via sulfurization of a bis(2-cyanoethyl) phosphite triester.

  DOI：

  10.1016/s0040-4039(00)73707-5

文献信息

• Enantioselective Responses to a Phosphorothioate Analogue of Lysophosphatidic Acid with LPA₃ Receptor-Selective Agonist Activity
  作者：Lian Qian、Yong Xu、Yutaka Hasegawa、Junken Aoki、Gordon B. Mills、Glenn D. Prestwich

  DOI：10.1021/jm034207p

  日期：2003.12.1

  The metabolically stabilized LPA analogue, 1-ole-oyl-2-O-methyl-rae-glycerophosphothioate (OMPT), is a potent agonist for the LPA(3) G-protein-coupled receptor. A new enantiospecific synthesis of both (2R)-OMPT and (2S)-OMPT is described. Calcium release assays in both LPA(3)-transfected insect Sf9 and rat hepatoma Rh7777 cells showed that (2S)OMPT was 5- to 20-fold more active than (2R)-OMPT. Similar results were found for calcium release, MAPK and Akt activation, and IL-6 release in human OVCAR3 ovarian cancer cells.
• Synthesis of (R)-lysothiophosphatidic Acid and (R)-thiophosphatidic acid
  作者：Norbert V. Heeb、Krishnan P. Nambiar

  DOI：10.1016/s0040-4039(00)73707-5

  日期：1993.9

  (R)-Thiophosphatidic acid and (R)-lysothiophosphatidic acid were obtained in an efficient synthesis from a chiral glycerol precursor via sulfurization of a bis(2-cyanoethyl) phosphite triester.