(+/-)-3-octadecanamido-2-ethoxy-1-(triphenylmethoxy)propane | 112988-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (+/-)-3-octadecanamido-2-ethoxy-1-(triphenylmethoxy)propane
• 英文别名: (+)-3-N-Octadecanamido-2-ethoxy-1-triphenylmethoxypropane；N-(2-ethoxy-3-trityloxypropyl)octadecanamide
• CAS: 112988-94-0
• 化学式: C₄₂H₆₁NO₃
• 分子量: 627.951
• InChiKey: LVCBPYUJLDQSPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-octadecanamido-2-ethoxy-1-(triphenylmethoxy)propane 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (+/-)-3-octadecanamido-2-ethoxy-1-propanol
  参考文献：
  名称：

  Method of treating hepatitis virus infections

  摘要：

  揭示了一种治疗肝炎病毒感染的方法。该方法包括向需要此类治疗的人类主体施用一种有效的抗肝炎病毒量的烷基脂质或烷基脂质衍生物。

  公开号：

  US05770584A1
• 作为产物：
  描述：

  N-(2,3-二羟基丙基)硬脂酰胺 在 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 10.0h， 生成 (+/-)-3-octadecanamido-2-ethoxy-1-(triphenylmethoxy)propane
  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antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic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

• Method of treating hepatitis virus infections
  申请人：Wake Forest University

  公开号：US05770584A1

  公开（公告）日：1998-06-23

  A method of treating hepatitis virus infection is disclosed. The method comprising administering to a human subject in need of such treatment an effective hepatitis virus-combatting amount of an alkyl lipid or alkyl lipid derivative.

  揭示了一种治疗肝炎病毒感染的方法。该方法包括向需要此类治疗的人类主体施用一种有效的抗肝炎病毒量的烷基脂质或烷基脂质衍生物。
• 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.
• Structure—activity relationships for enhancement of paracellular permeability by 2-alkoxy-3-alkylamidopropylphosphocholines across Caco-2 cell monolayers
  作者：Dong-Zhou Liu、Susan L. Morris-Natschke、Louis S. Kucera、Khalid S. Ishaq、Dhiren R. Thakker

  DOI：10.1021/js9900957

  日期：1999.11

  The oral route is the preferred route of delivery for a large number of drug molecules. However, the intestinal epithelium presents a formidable barrier for delivery of drugs into systemic circulation. Phospholipids are among compounds that enhance the absorption of drugs across the intestinal epithelium. In this paper, we describe structure-activity relationships for phospholipid derivatives as enhancers of paracellular permeability across Caco-2 cell monolayers. in a series of 2-alkoxy-3-alkylamidopropylphosphocholine derivatives, compounds with a long chain at C-3 (R-3) and short chain at C-2 (R-2) were potent in causing a decrease in transepithelial electrical resistance (TEER) and an increase in mannitol transport, but also showed significant cytotoxicity. Compounds with 9-11 carbons at C-3 and 6-10 carbons at C-2 provided good separation (up to 2.7-fold) between activity and cytotoxicity. Notably, a good correlation (r(2) = 0.93) was observed between EC50 (TEER) [concentration that caused a drop in TEER to 50% of its control (untreated) value] and EC10X (mannitol) [concentration that caused 10-fold increase in mannitol transport over the control (untreated) value], confirming that a decrease in TEER is associated with enhanced permeability of the hydrophilic compounds across Caco-2 cell monolayers. Compounds with medium to long carbon chains at C-2 and C-3, and the total carbons in the alkyl chains > 20, showed poor activity and no cytotoxicity.
• 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：——
• (PHOSPHO)LIPIDS FOR COMBATTING HEPATITIS B VIRUS INFECTION
  申请人：WAKE FOREST UNIVERSITY

  公开号：EP0702556A1

  公开（公告）日：1996-03-27