(+/-)-N,N,N-trimethyl-N-<4-<3-(octadecyloxy)-2-ethoxypropoxy>-1-butyl>ammonium bromide | 126614-17-3

• 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: (+/-)-N,N,N-trimethyl-N-<4-<3-(octadecyloxy)-2-ethoxypropoxy>-1-butyl>ammonium bromide
• 英文别名: (+/-)-N,N,N-trimethyl-N-{4-[3-(octadecyloxy)-2-ethoxypropoxy]-1-butyl}ammonium bromide；4-(2-Ethoxy-3-octadecoxypropoxy)butyl-trimethylazanium;bromide
• CAS: 126614-17-3
• 化学式: Br*C₃₀H₆₄NO₃
• 分子量: 566.747
• InChiKey: HAPDTLWTLZEORK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  35
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  rac-1-O-octadecyl-2-O-ethylglycerol 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.0h， 生成 (+/-)-N,N,N-trimethyl-N-<4-<3-(octadecyloxy)-2-ethoxypropoxy>-1-butyl>ammonium bromide
  参考文献：
  名称：

  Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties

  摘要：

  Novel quaternary amine ether lipids have been synthesized and tested for inhibition of neoplastic cell proliferation with the HL-60 promyelocytic leukemia cell line. These compounds contain a positively charged quaternary amine functional group attached either directly to the glycerol backbone or at the end of an alkoxy chain. The biological testing has identified several analogues with activity equivalent to or greater than that exhibited by the reference compound in this assay, ET-18-OMe (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine). Among the most active analogues are compounds 11, [N,N,N-triethyl-3-(hexadecyloxy)-2-ethoxy-1-propylammonium bromide] and 22 [N-[4-[3-(hexadecyloxy)-2-ethoxypropoxy]-1-butyl]pyridinium bromide], which are approximately 3 times as active as the reference standard.

  DOI：

  10.1021/jm00168a042

文献信息

• MORRIS-NATSCHKE, SUSAN L.;MEYER, KAREN L.;MARASCO, CANIO J. (JR);PIANTADO+, J. MED. CHEM., 33,(1990) N, C. 1812-1818
  作者：MORRIS-NATSCHKE, SUSAN L.、MEYER, KAREN L.、MARASCO, CANIO J. (JR)、PIANTADO+

  DOI：——

  日期：——
• Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties
  作者：Susan L. Morris-Natschke、Karen L. Meyer、Canio J. Marasco、Claude Piantadosi、Fiona Rossi、Patrick L. Godwin、Edward J. Modest

  DOI：10.1021/jm00168a042

  日期：1990.6

  Novel quaternary amine ether lipids have been synthesized and tested for inhibition of neoplastic cell proliferation with the HL-60 promyelocytic leukemia cell line. These compounds contain a positively charged quaternary amine functional group attached either directly to the glycerol backbone or at the end of an alkoxy chain. The biological testing has identified several analogues with activity equivalent to or greater than that exhibited by the reference compound in this assay, ET-18-OMe (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine). Among the most active analogues are compounds 11, [N,N,N-triethyl-3-(hexadecyloxy)-2-ethoxy-1-propylammonium bromide] and 22 [N-[4-[3-(hexadecyloxy)-2-ethoxypropoxy]-1-butyl]pyridinium bromide], which are approximately 3 times as active as the reference standard.