Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester 4-(diphenoxy-phosphoryloxy)-cyclohexyl ester phenyl ester | 161003-27-6

• 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: Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester 4-(diphenoxy-phosphoryloxy)-cyclohexyl ester phenyl ester
• CAS: 161003-27-6
• 化学式: C₅₉H₉₆O₁₀P₂
• 分子量: 1027.35
• InChiKey: SCNYMJRDGSQOGW-DRGJOELMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.16
• 重原子数：
  71.0
• 可旋转键数：
  46.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester 4-(diphenoxy-phosphoryloxy)-cyclohexyl ester phenyl ester 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 trans-4-phosphorylcyclohexyl 1-(1,2-di-O-n-hexadecyl-sn-glycer-3-yl phosphate)
  参考文献：
  名称：

  Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

  摘要：

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.

  DOI：

  10.1016/0223-5234(94)90146-5
• 作为产物：
  描述：

  溴代十六烷 在 platinum on activated charcoal 吡啶 、 MSNT 、 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 5.0~50.0 ℃ 、399.97 Pa 条件下， 反应 9.0h， 生成 Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester 4-(diphenoxy-phosphoryloxy)-cyclohexyl ester phenyl ester
  参考文献：
  名称：

  Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

  摘要：

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.

  DOI：

  10.1016/0223-5234(94)90146-5