rac-2-methoxy-3-octadecanamido-1-propylphosphocholine | 112989-00-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rac-2-methoxy-3-octadecanamido-1-propylphosphocholine
• 英文别名: rac-3-Hexadecanamido-2-methoxypropyl phosphocholine；[3-(hexadecanoylamino)-2-methoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 112989-00-1
• 化学式: C₂₅H₅₃N₂O₆P
• 分子量: 508.679
• InChiKey: GLZQVYDFXUECNY-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  24
• 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 rac-2-methoxy-3-octadecanamido-1-propylphosphocholine
  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antitumor phospholipid ET-18-OMe (1-octadecyl-2-methoxy-rac-glycero-3-phosphocholine), in which the 1-ether oxygen has been replaced by an amido group, have been prepared and evaluated for in vitro cytotoxic effects and for inhibition of protein kinase C. The title compounds exhibit cytotoxic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：——
• US6399107B1
  申请人：——

  公开号：US6399107B1

  公开（公告）日：2002-06-04
• [EN] USE OF INHIBITORS OF GAG SYNTHESIS FOR THE TREATMENT OF CORNEAL HAZE<br/>[FR] UTILISATION D'INHIBITEURS DE SYNTHESE DE GAG POUR LE TRAITEMENT DE L'OPACITE CORNEENNE
  申请人：ALCON LAB INC

  公开号：WO2000037072A1

  公开（公告）日：2000-06-29

  Compositions and methods for the treatment of corneal haze are disclosed. The compositions and methods are particularly directed to the use of GAG synthesis inhibitors in the treatment of corneal haze.
• 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.