(3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyl-10-(oxiran-2-ylmethyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene | 194409-61-5

• 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: (3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyl-10-(oxiran-2-ylmethyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene
• CAS: 194409-61-5
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: SBUCMCIVCDBLPP-XQHQXFBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.45
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyl-10-(oxiran-2-ylmethyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene 在 sodium periodate 、 sodium sulfate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis of novel 10-deoxoartemisinins

  摘要：

  The synthesis of novel 10-deoxoartemisinin derivatives containing heterocyclic rings and hydrophilic groups, and their antimalarial activity assessment are described. Most of the synthesized derivatives are more potent than artemisinin, especially, some of them are 20-25 times more potent than artemisinin to two chloroquine-resistant and sensitive clones of P. falciparum. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.050
• 作为产物：
  描述：

  dihydroartemisinin 在 吡啶 、 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 41.0h， 生成 (3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyl-10-(oxiran-2-ylmethyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene
  参考文献：
  名称：

  Synthesis of novel 10-deoxoartemisinins

  摘要：

  The synthesis of novel 10-deoxoartemisinin derivatives containing heterocyclic rings and hydrophilic groups, and their antimalarial activity assessment are described. Most of the synthesized derivatives are more potent than artemisinin, especially, some of them are 20-25 times more potent than artemisinin to two chloroquine-resistant and sensitive clones of P. falciparum. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.050

文献信息

• Synthesis and Antimalarial Activities of Several Fluorinated Artemisinin Derivatives
  作者：Yu Ming Pu、Daniel S. Torok、Herman Ziffer、Xing-Qing Pan、Steven R. Meshnick

  DOI：10.1021/jm00020a028

  日期：1995.9

  The carbonyl groups in several artemisinin derivatives were converted into geminal difluorinated compounds on treatment with diethylaminosulfur trifluoride. A number of other mono- and polyfluorinated artemisinin derivatives were prepared. Their in vitro antimalarial activities were all equal to or greater than the nonfluorinated analogs or precursors.

  几种青蒿素衍生物中的羰基在用二乙氨基三氟化硫处理后转化为孪生二氟化化合物。制备了许多其他单氟和多氟青蒿素衍生物。它们的体外抗疟活性均等于或大于非氟化类似物或前体。