1-O-(12-oxooctadecyl)-2-O-methyl-3-O-benzylglycerol

• 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: 1-O-(12-oxooctadecyl)-2-O-methyl-3-O-benzylglycerol
• 英文别名: 18-(2-Methoxy-3-phenylmethoxypropoxy)octadecan-7-one
• 化学式: C₂₉H₅₀O₄
• 分子量: 462.714
• InChiKey: CQIABUNVUXSAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-(12-oxooctadecyl)-2-O-methyl-3-O-benzylglycerol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 为溶剂， 以85%的产率得到1-O-(12-oxooctadecyl)-2-O-methylglycerol
  参考文献：
  名称：

  Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity

  摘要：

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.

  DOI：

  10.1021/jm00007a018
• 作为产物：
  描述：

  1-O-苄基-2-O-甲基甘油 、 12-oxo-1-octadecyl methanesulfonate 在 potassium hydride 作用下， 生成 1-O-(12-oxooctadecyl)-2-O-methyl-3-O-benzylglycerol
  参考文献：
  名称：

  Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity

  摘要：

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.

  DOI：

  10.1021/jm00007a018

文献信息

• Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity
  作者：Empar Fos、Nuria Suesa、Liset Borras、Cinta Lobato、Patrizia Banfi、Romolo A. Gambetta、Franco Zunino、David Mauleon、Germano Carganico

  DOI：10.1021/jm00007a018

  日期：1995.3

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.