2-O-Benzyl-1-O-hexadecyl-3-O-(4-methoxybenzyl)-sn-glycerol | 137540-90-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-O-Benzyl-1-O-hexadecyl-3-O-(4-methoxybenzyl)-sn-glycerol
• 英文别名: 1-[[(2R)-3-hexadecoxy-2-phenylmethoxypropoxy]methyl]-4-methoxybenzene
• CAS: 137540-90-0
• 化学式: C₃₄H₅₄O₄
• 分子量: 526.8
• InChiKey: LJYYTDYMWLAQAP-UUWRZZSWSA-N

物化性质

• 沸点：
  606.2±55.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  38.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-O-Benzyl-1-O-hexadecyl-3-O-(4-methoxybenzyl)-sn-glycerol 在 palladium on activated charcoal 氢气 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 1-O-十六烷基-SN-甘油基-3-胆碱磷酸
  参考文献：
  名称：

  Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue

  摘要：

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.

  DOI：

  10.1021/jm049006f
• 作为产物：
  描述：

  4-甲氧基氯苄 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-O-Benzyl-1-O-hexadecyl-3-O-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue

  摘要：

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.

  DOI：

  10.1021/jm049006f

文献信息

• Bauer, Friederike; Ruess, Klaus-Peter; Lieflaender, Manfred, Liebigs Annalen der Chemie, 1992, # 1, p. 47 - 50
  作者：Bauer, Friederike、Ruess, Klaus-Peter、Lieflaender, Manfred

  DOI：——

  日期：——