2',3'-O,N-((4-methoxy)benzylidene-7-(1,2-O-isopropylidene-malyl) paclitaxel | 265659-43-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2',3'-O,N-((4-methoxy)benzylidene-7-(1,2-O-isopropylidene-malyl) paclitaxel
• CAS: 265659-43-6
• 化学式: C₆₂H₆₅NO₁₉
• 分子量: 1128.19
• InChiKey: MERYIWVTHDCGAR-OXAGUJTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  82.0
• 可旋转键数：
  13.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  252.33
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2',3'-O,N-((4-methoxy)benzylidene-7-(1,2-O-isopropylidene-malyl) paclitaxel 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以89%的产率得到
  参考文献：
  名称：

  Paclitaxel esters of malic acid as prodrugs with improved water solubility

  摘要：

  The synthesis of paclitaxel esters of malic acid is described. These compounds were found to have improved water solubility and are stable in solution at neutral pH. The C2' modified compounds behave as prodrugs, that is, paclitaxel is generated upon exposure to human plasma, whereas the C7 modified derivatives do not. 2'-Malyl paclitaxel sodium salt demonstrated enhanced antitumour activity and less toxicity in a P388 murine leukaemia in vivo model when compared to paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00301-6
• 作为产物：
  描述：

  (S)-[2,2-二甲基-5-氧代二氧戊环-4-基]乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 2',3'-O,N-((4-methoxy)benzylidene-7-(1,2-O-isopropylidene-malyl) paclitaxel
  参考文献：
  名称：

  Paclitaxel esters of malic acid as prodrugs with improved water solubility

  摘要：

  The synthesis of paclitaxel esters of malic acid is described. These compounds were found to have improved water solubility and are stable in solution at neutral pH. The C2' modified compounds behave as prodrugs, that is, paclitaxel is generated upon exposure to human plasma, whereas the C7 modified derivatives do not. 2'-Malyl paclitaxel sodium salt demonstrated enhanced antitumour activity and less toxicity in a P388 murine leukaemia in vivo model when compared to paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00301-6