α-tocopheryl maleamide | 832082-20-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: α-tocopheryl maleamide
• 英文别名: (Z)-4-oxo-4-[[(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl]amino]but-2-enoic acid
• CAS: 832082-20-9
• 化学式: C₃₃H₅₃NO₄
• 分子量: 527.788
• InChiKey: GAEQOTKVXDYOMY-JQRBHALPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  马来酸酐 、 α-tocopheramine 以 吡啶 、 二氯甲烷 为溶剂， 以92%的产率得到α-tocopheryl maleamide
  参考文献：
  名称：

  A novel synthesis of tocopheryl amines and amides

  摘要：

  We report the synthesis of tocopheryl amines and amides from commercially available tocopherols. This synthesis improves the yield and diastereomeric purity of these biologically important compounds. The tocopheryl amines were prepared from the corresponding alpha- and delta-tocopherols using two distinct synthetic routes. The introduction of the C(6)-amino group can be achieved by aryl nitration/reduction or by Pd-catalyzed Substitution of an aryl triflate, depending on the structure of the starting material. We also prepared the succinamide and maleamide derivatives of each amine. Tocopheryl amides are more potent pro-apoptotic anti-cancer agents than the corresponding alpha-tocopheryl esters. These compounds act selectively within the mitochondria of cancer cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.056

文献信息

• Liposomal Formulations of Tocopheryl Amides
  申请人：Salvatore Brian A

  公开号：US20100260830A1

  公开（公告）日：2010-10-14

  Formulations of N-chroman dicarboxylic acid derivatives and their bioisosteres in liposomal systems. Lyophilized liposomal dosage forms of N-chromans, are found to be stable, to achieve therapeutically meaningful plasma levels on administration to a mammalian host, and to demonstrate selective pro-apoptotic oncolytic properties in vivo. Advantageously, these formulations overcome the systemic toxicity that characterized their administration by other dosage forms.