1D-3-(dimethylmethylenephosphonate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol | 922712-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 1D-3-(dimethylmethylenephosphonate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol
• CAS: 922712-51-4
• 化学式: C₁₇H₃₇O₁₇P₃
• 分子量: 606.392
• InChiKey: CEKPDLYXAHOYPZ-UTQGOSHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  37.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  191.43
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1D-3-(dimethylmethylenephosphonate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol 在 四氮唑 、 bis(trimethylsilyl)trifluoroacetamide 、 三甲基溴硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.67h， 生成 1D-O-(1,2-di-O-palmitoyl-sn-(2S)-glycerol)-3-methylenephosphonate-4,5-bisphosphate-myo-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of PTEN-Resistant Analogues of Phosphatidylinositol 3,4,5-Trisphosphate

  摘要：

  The activation of phosphatidylinositol 3-kinase (PI 3-K) and subsequent production of PtdIns(3,4,5)P3 launches a signal transduction cascade that impinges on a plethora of downstream effects on cell physiology. Control of PI 3-K and PtdIns(3,4,5)P3 levels is an important therapeutic target in treatments for allergy, inflammation, cardiovascular, and malignant human diseases. We designed metabolically stabilized, that is, phosphatase resistant, analogues of PtdIns(3,4,5)P3 as probes for long-lived potential agonists or potential antagonists for cellular events mediated by PtdIns(3,4,5)P3. In particular, two types of analogues were prepared containing phosphomimetics that would be selectively resistant to the lipid 3-phosphatase PTEN. The total asymmetric synthesis of the 3-phosphorothioate-PtdIns(3,4,5)P3 and 3-methylenephosphonate-PtdIns(3,4,5)P3 analogues is described. These two analogues showed differential binding to PtdIns(3,4,5)P3 binding modules, and both were potential long-lived activators that mimicked insulin action in sodium transport in A6 cells.

  DOI：

  10.1021/ja065002j
• 作为产物：
  描述：

  1D-1-O-(tert-butyldiphenylsilyl)-3-O-benzoyl-4,5-O-(1,1,3,3-tetraisopropyldisiloxanedi-1,3-yl)-myo-inositol 在 四氮唑 、 正丁基锂 、 四丁基氟化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 1D-3-(dimethylmethylenephosphonate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of PTEN-Resistant Analogues of Phosphatidylinositol 3,4,5-Trisphosphate

  摘要：

  The activation of phosphatidylinositol 3-kinase (PI 3-K) and subsequent production of PtdIns(3,4,5)P3 launches a signal transduction cascade that impinges on a plethora of downstream effects on cell physiology. Control of PI 3-K and PtdIns(3,4,5)P3 levels is an important therapeutic target in treatments for allergy, inflammation, cardiovascular, and malignant human diseases. We designed metabolically stabilized, that is, phosphatase resistant, analogues of PtdIns(3,4,5)P3 as probes for long-lived potential agonists or potential antagonists for cellular events mediated by PtdIns(3,4,5)P3. In particular, two types of analogues were prepared containing phosphomimetics that would be selectively resistant to the lipid 3-phosphatase PTEN. The total asymmetric synthesis of the 3-phosphorothioate-PtdIns(3,4,5)P3 and 3-methylenephosphonate-PtdIns(3,4,5)P3 analogues is described. These two analogues showed differential binding to PtdIns(3,4,5)P3 binding modules, and both were potential long-lived activators that mimicked insulin action in sodium transport in A6 cells.

  DOI：

  10.1021/ja065002j