Butanoic acid, 4,4 inverted exclamation marka-[1,3-phenylene(methyleneimino)]bis[4-oxo-, 1,1 inverted exclamation marka-bis[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester | 1398712-88-3

• 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: Butanoic acid, 4,4 inverted exclamation marka-[1,3-phenylene(methyleneimino)]bis[4-oxo-, 1,1 inverted exclamation marka-bis[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester
• 英文别名: [(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] 4-oxo-4-[[3-[[[4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoyl]amino]methyl]phenyl]methylamino]butanoate
• CAS: 1398712-88-3
• 化学式: C₄₆H₆₄N₂O₁₄
• 分子量: 869.019
• InChiKey: JDQMWWSYBLADFJ-OBIOAJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  62
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  间苯二甲胺 、 青蒿琥酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以86%的产率得到Butanoic acid, 4,4 inverted exclamation marka-[1,3-phenylene(methyleneimino)]bis[4-oxo-, 1,1 inverted exclamation marka-bis[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester
  参考文献：
  名称：

  New artesunic acid homodimers: Potent reversal agents of multidrug resistance in leukemia cells

  摘要：

  To evade the problem of multidrug resistance, hybridization of natural products in dimers is considered as an effective method. After the successful synthesis of three artesunic acid homodimers connected by different types of chemical linkers, we analyzed their activity against human CCRF-CEM and multidrug-resistant P-glycoprotein-overexpressing CEM/ADR 5000 leukemia cells and observed, that multidrug resistant cells were not cross-resistant to the new compounds. Collateral sensitivity was observed for artesunic acid homodimer 2. The obtained results deliver valuable information about the linker's structure which is required for homodimers to be highly cytotoxic. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.015

文献信息

• New artesunic acid homodimers: Potent reversal agents of multidrug resistance in leukemia cells
  作者：Christoph Reiter、Astrid Herrmann、Aysun Çapci、Thomas Efferth、Svetlana B. Tsogoeva

  DOI：10.1016/j.bmc.2012.07.015

  日期：2012.9

  To evade the problem of multidrug resistance, hybridization of natural products in dimers is considered as an effective method. After the successful synthesis of three artesunic acid homodimers connected by different types of chemical linkers, we analyzed their activity against human CCRF-CEM and multidrug-resistant P-glycoprotein-overexpressing CEM/ADR 5000 leukemia cells and observed, that multidrug resistant cells were not cross-resistant to the new compounds. Collateral sensitivity was observed for artesunic acid homodimer 2. The obtained results deliver valuable information about the linker's structure which is required for homodimers to be highly cytotoxic. (C) 2012 Elsevier Ltd. All rights reserved.