2-[3-[[(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]propyl]isoindole-1,3-dione | 171012-16-1

• 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: 2-[3-[[(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]propyl]isoindole-1,3-dione
• CAS: 171012-16-1
• 化学式: C₂₆H₃₃NO₇
• 分子量: 471.551
• InChiKey: OYRNEPNETVFTTK-UPRDFIFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[3-[[(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]propyl]isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以22%的产率得到3-(10β-dihydroartemisinoxy)propylamine
  参考文献：
  名称：

  Antimalarial activity of new ethers and thioethers of dihydroartemisinin

  摘要：

  Various ethers and thioethers of dihydroartemisinin were prepared by treating dihydroartemisinin with hydroxy alkyl, substituted phenol, hydroxy aralkyl, hydroxy alkynyl and hydroxy heteroalkyl or thiols in the presence of BF(3)Et(2)O. The thioethers 64 and 65 were further oxidised to the respective sulfoxides. These derivatives were tested in the Plasmodium berghei K-173-infected mice and some active compounds were tested in chloroquine-resistant P yoelii nigeriensis (NS)-infected mice. Initially the compounds were administered subcutaneously and subsequently by the oral route. The antimalarial activity of the compounds 22, 23, 36, 66 and 79 were found to be comparable to that of arteether when tested in the K-173-infected mice. These compounds also showed activity in the P y nigeriensis (NS)-infected mice.

  DOI：

  10.1016/0223-5234(96)88287-0
• 作为产物：
  描述：

  dihydroartemisinin 在 三氟甲磺酸三甲基硅酯 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 2-[3-[[(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]propyl]isoindole-1,3-dione
  参考文献：
  名称：

  TMS三氟甲磺酸酯催化CO偶联反应合成O-氨基二氢青蒿素

  摘要：

  ø -Aminodihydroartemisinin合成首次经由TMS三氟甲磺酸酯催化的偶联反应Ó -acetylartemisinin。反应以高产率进行，而不会失去青蒿素骨架的内过氧化物。新的偶联反应用于制备水溶性提高的青蒿素O-糖苷。O-氨基二氢青蒿素很容易与苯甲醛反应生成相应的肟衍生物，证明了该化合物在制备各种青蒿素结合物方面的潜力。

  DOI：

  10.1021/jo0498765

文献信息

• Antimalarial activity of new ethers and thioethers of dihydroartemisinin
  作者：B Venugopalan、PJ Karnik、CP Bapat、DK Chatterjee、N Iyer、D Lepcha

  DOI：10.1016/0223-5234(96)88287-0

  日期：1995.1

  Various ethers and thioethers of dihydroartemisinin were prepared by treating dihydroartemisinin with hydroxy alkyl, substituted phenol, hydroxy aralkyl, hydroxy alkynyl and hydroxy heteroalkyl or thiols in the presence of BF(3)Et(2)O. The thioethers 64 and 65 were further oxidised to the respective sulfoxides. These derivatives were tested in the Plasmodium berghei K-173-infected mice and some active compounds were tested in chloroquine-resistant P yoelii nigeriensis (NS)-infected mice. Initially the compounds were administered subcutaneously and subsequently by the oral route. The antimalarial activity of the compounds 22, 23, 36, 66 and 79 were found to be comparable to that of arteether when tested in the K-173-infected mice. These compounds also showed activity in the P y nigeriensis (NS)-infected mice.
• Synthesis of <i>O</i>-Aminodihydroartemisinin via TMS Triflate Catalyzed C−O Coupling Reaction
  作者：Byung Ju Kim、Tomikazu Sasaki

  DOI：10.1021/jo0498765

  日期：2004.4.1

  the artemisinin backbone. The new coupling reaction was employed to prepare artemisinin O-glycosides with improved water solubility. O-Aminodihydroartemisinin reacts readily with benzaldehyde to give the corresponding oxime derivative, demonstrating the potential of this compound for the preparation of various artemisinin conjugates.

  ø -Aminodihydroartemisinin合成首次经由TMS三氟甲磺酸酯催化的偶联反应Ó -acetylartemisinin。反应以高产率进行，而不会失去青蒿素骨架的内过氧化物。新的偶联反应用于制备水溶性提高的青蒿素O-糖苷。O-氨基二氢青蒿素很容易与苯甲醛反应生成相应的肟衍生物，证明了该化合物在制备各种青蒿素结合物方面的潜力。