外消旋-3-十八烷酰胺基-2-甲氧基丙烷-1-醇磷酰胆碱 | 88876-07-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 外消旋-3-十八烷酰胺基-2-甲氧基丙烷-1-醇磷酰胆碱
• 中文别名: 7-氯咪唑并[2,1-f]哒嗪-2-羧酸
• 英文名称: (+/-)-3-octadecanamido-2-methoxypropan-1-ol phosphocholine
• 英文别名: rac-3-Octadecanamido-2-Methoxypropan-1-ol Phosphocholine；rac-3-Octadecanamido-2-methoxypropyl phosphocholine；[2-methoxy-3-(octadecanoylamino)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 88876-07-7
• 化学式: C₂₇H₅₇N₂O₆P
• 分子量: 536.733
• InChiKey: KTJPWDKOKGANNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  26
• 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

安全信息

• 海关编码：
  2924199090

反应信息

• 作为产物：
  描述：

  N-(2,3-二羟基丙基)硬脂酰胺 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 外消旋-3-十八烷酰胺基-2-甲氧基丙烷-1-醇磷酰胆碱
  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antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic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

• Phospholipid derivatives, process for preparation thereof and pharmaceutical composition of the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0092190A2

  公开（公告）日：1983-10-26

  New phospholipid derivatives represented by the formula: wherein R1 is alkyl, alkoxy or alkanoylamino; R2 is lower alkyl, lower alkanesulfonyl or arenesulfonyl; R3, R4 and R5 are each lower alkyl; n is 0 or 1; A is lower alkylene optionally interrupted by a -NHCO- group; and Q is oxido or lower alkoxy; provided that n is 0 or A is lower alkylene interrupted by a -NHCO- group, or Q is lower alkoxy, when R1 is alkoxy and R2 is lower alkyl; and pharmaceutically acceptable salts thereof, which exhibit antitumor activity.

  由以下式子表示的新磷脂衍生物 其中 R1为烷基、烷氧基或烷酰氨基 R2 是低级烷基、低级烷磺酰基或异烷磺酰基 R3、R4 和 R5 各为低级烷基； n 为 0 或 1； A 是低级亚烷基，可选择被一个 -NHCO- 基团打断； 和 Q 是氧代或低级烷氧基； 条件是 n 为 0，或 A 为被 -NHCO- 基团打断的低级亚烷基，或 -或 Q 是低级烷氧基，当 R1 是烷氧基且 R2 是低级烷基时；及其药学上可接受的盐类，具有抗肿瘤活性。
• Maturation of mammalian hepatocytes
  申请人：Takara Bio Europe AB

  公开号：US10913932B2

  公开（公告）日：2021-02-09

  The present invention relates to directed differentiation and maturation of mammalian hepatocytes, such as human hepatocytes. The hepatocyte obtained in accordance with the present invention show a phenotype which is more similar to that of primary hepatocytes than previously shown. In particular, the present invention relates to exposure of mammalian hepatocytes, such as human hepatocytes, to at least one maturation factor selected from the group consisting of Src kinase inhibitors, vitamin D including precursors, metabolites and analogs thereof, hypoxia inducing compounds, sphingosine and sphingosine derivatives, activators of peroxisome proliferator-activated receptors (PPARs), platelet-activating factor (PAF), PKC inhibitors, and combinations thereof.

  本发明涉及哺乳动物肝细胞（如人类肝细胞）的定向分化和成熟。根据本发明获得的肝细胞显示的表型比以前显示的更类似于原代肝细胞的表型。特别是，本发明涉及将哺乳动物肝细胞（如人类肝细胞）暴露于至少一种成熟因子，该因子选自由 Src 激酶抑制剂、维生素 D（包括其前体、代谢物和类似物）、缺氧诱导化合物、鞘磷脂和鞘磷脂衍生物、过氧化物酶体增殖激活受体（PPAR）激活剂、血小板激活因子（PAF）、PKC 抑制剂及其组合组成的组。
• 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：——
• MATURATION OF MAMMALIAN HEPATOCYTES
  申请人：Takara Bio Europe AB

  公开号：EP3303566A2

  公开（公告）日：2018-04-11