(+/-)-3-(3-octadecylureido)-2-ethoxy-1-propanol phosphocholine | 112989-09-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-3-(3-octadecylureido)-2-ethoxy-1-propanol phosphocholine
• 英文别名: rac-3-Octadecanureido-2-ethoxypropyl phosphocholine；[2-ethoxy-3-(octadecylcarbamoylamino)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 112989-09-0
• 化学式: C₂₉H₆₂N₃O₆P
• 分子量: 579.802
• InChiKey: IMUXPCJVQLNCHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异氰酸十八酯 在 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (+/-)-3-(3-octadecylureido)-2-ethoxy-1-propanol phosphocholine
  参考文献：
  名称：

  Synthesis and evaluation of neoplastic cell growth inhibition of 1-N-alkylamide analogs of glycero-3-phosphocholine

  摘要：

  Previously unreported analogues of the synthetic antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic effects against several tumor cell lines and are approximately equipotent to ET-18-OMe. The compounds were also found to inhibit protein kinase C in an in vitro assay. This work is a continuation of our previous structure-activity studies on thio-substituted derivatives of ET-18-OMe.

  DOI：

  10.1021/jm00399a029

文献信息

• MARX, MICHAEL H.;PIANTADOSI, CLAUDE;NOSEDA, ALESSANDRO;DANIEL, LARRY W.;M+, J. MED. CHEM., 31,(1988) N 4, 858-863
  作者：MARX, MICHAEL H.、PIANTADOSI, CLAUDE、NOSEDA, ALESSANDRO、DANIEL, LARRY W.、M+

  DOI：——

  日期：——
• Synthesis and evaluation of neoplastic cell growth inhibition of 1-N-alkylamide analogs of glycero-3-phosphocholine
  作者：Michael H. Marx、Claude Piantadosi、Alessandro Noseda、Larry W. Daniel、Edward J. Modest

  DOI：10.1021/jm00399a029

  日期：1988.4

  Previously unreported analogues of the synthetic antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic effects against several tumor cell lines and are approximately equipotent to ET-18-OMe. The compounds were also found to inhibit protein kinase C in an in vitro assay. This work is a continuation of our previous structure-activity studies on thio-substituted derivatives of ET-18-OMe.