[2-乙氧基-3-(棕榈酰氨基)丙基]2-三甲基铵磷酸乙基酯盐 | 112989-01-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: [2-乙氧基-3-(棕榈酰氨基)丙基]2-三甲基铵磷酸乙基酯盐
• 英文名称: rac-2-ethoxy-3-hexadecanamido-1-propylphosphocholine
• 英文别名: rac-3-Hexadecanamido-2-ethoxypropyl phosphocholine；[2-ethoxy-3-(hexadecanoylamino)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 112989-01-2
• 化学式: C₂₆H₅₅N₂O₆P
• 分子量: 522.706
• InChiKey: USUMXADKOISKIL-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  96.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+/-)-3-hexadecanamido-1,2-propanediol 在 甲醇 、 三氟化硼 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 [2-乙氧基-3-(棕榈酰氨基)丙基]2-三甲基铵磷酸乙基酯盐
  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antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic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

• 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antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic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.
• 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：——
• US6399107B1
  申请人：——

  公开号：US6399107B1

  公开（公告）日：2002-06-04
• Structure−Activity Relationship for Enhancement of Paracellular Permeability across Caco-2 Cell Monolayers by 3-Alkylamido-2-alkoxypropylphosphocholines
  作者：Hui Ouyang、Susan L. Morris-Natschke、Khalid S. Ishaq、Peter Ward、Dongzhou Liu、Sarah Leonard、Dhiren R. Thakker

  DOI：10.1021/jm020001x

  日期：2002.6.1

  Paracellular permeability enhancers have been used to improve the oral bioavailability of hydrophilic drugs; however, the mechanism of action of many enhancers is poorly understood. In this study, highly potent enhancers of paracellular permeability were identified in the 3-alkylamido-2-alkoxypropylphosphocholine series, and a structure-activity relationship was developed for enhancement of paracellular permeability across Caco-2 cell monolayers. Compounds with short (<5 carbons) hydrocarbon chains at both C-2 and C-3 were generally inactive. The potency exhibited a parabolic relationship with respect to the chain length at either C-2 or C-3. Linear molecules (i.e., compounds with a short hydrocarbon chain at C-2 or C-3 and a long hydrocarbon chain on C-3 or C-2, respectively) were more potent than the corresponding branched molecules with the same carbon load. The efficacy of 3-alkylamido2-alkoxypropylphosphocholines as enhancers of paracellular permeability was not dependent on their existence in micellar form or their ability to alter the fluidity of cell membrane. Previously, a correlation-between the potency of alkylphosphocholines as enhancers of paracellular permeability and the inhibitors of phospholipase C (PLC) was established in Madine Darby canine kidney (MDCK) cell monolayers. The potencies of selected 3-alkylamido-2-alkoxypropylphosphocholines as inhibitors of PLC and enhancers of paracellular permeability fit well into this correlation. Therefore, phosphocholines are likely to increase paracellular permeability by modulating the signal transduction pathway initiated by a PLC-catalyzed reaction rather than by physically altering the cell membrane.