10α(4-chlorophenoxy)artemisinin

• 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: 10α(4-chlorophenoxy)artemisinin
• 英文别名: (1R,4S,5R,8S,9R,10S,12R,13R)-10-(4-chlorophenoxy)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• 化学式: C₂₁H₂₇ClO₅
• 分子量: 394.895
• InChiKey: VMZFRVFBWRJNEC-YBVSZUDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dihydroartemisinin 、 对氯苯酚 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以35%的产率得到10α(4-chlorophenoxy)artemisinin
  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

文献信息

• Application of the TMSOTfAgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin
  作者：Paul M. O'Neill、Alison Miller、Stephen A. Ward、B.Kevin Park、Feodor Scheinmann、Andrew V. Stachulski

  DOI：10.1016/s0040-4039(99)01891-2

  日期：1999.12

  promotes the efficient C-10 phenoxylation of dihydroartemisinin (3) in good chemical yield and excellent stereoselectivity. In contrast to previous reports on other phenoxyglycoside derivatives, the phenoxy derivatives (5a–11b) of dihydroartemisinin do not undergo O to C rearrangement to the corresponding C-10-aryl derivatives. All of the new derivatives had potent in vitro antimalarial activity.

  TMSOTf和AgClO 4的组合可促进二氢青蒿素（3）的有效C-10苯氧基化反应，化学产率高，立体选择性好。与先前关于其他苯氧基糖苷衍生物的报道相比，二氢青蒿素的苯氧基衍生物（5a-11b）不会经历O到C的重排，变成相应的C-10-芳基衍生物。所有这些新衍生物都具有强大的体外抗疟活性。
• KR20220089943A
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.