(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl 2-((3R,4S,6S)-6-((R)-((tert-butyldimethylsilyl)oxy)(6-methoxyquinolin-4-yl)methyl)quinuclidin-3-yl)acetate | 945975-72-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl 2-((3R,4S,6S)-6-((R)-((tert-butyldimethylsilyl)oxy)(6-methoxyquinolin-4-yl)methyl)quinuclidin-3-yl)acetate
• CAS: 945975-72-4
• 化学式: C₄₁H₆₀N₂O₈Si
• 分子量: 737.021
• InChiKey: WSLHDIATBLNQQR-HXWRIJOSSA-N

物化性质

• 沸点：
  736.6±60.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  52.0
• 可旋转键数：
  8.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  97.81
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl 2-((3R,4S,6S)-6-((R)-((tert-butyldimethylsilyl)oxy)(6-methoxyquinolin-4-yl)methyl)quinuclidin-3-yl)acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到[(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] 2-[(3R,4S,6S)-6-[(R)-hydroxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]acetate
  参考文献：
  名称：

  A novel artemisinin–quinine hybrid with potent antimalarial activity

  摘要：

  Artemisinin was reduced to dihydroartemisinin and coupled to a carboxylic acid derivative of quinine via an ester linkage. This novel hybrid molecule had potent activity against the 3D7 and (drug-resistant) FcB1 strains of Plasmodium falciparum? in culture. The activity was superior to that of artemisinin alone, quinine alone, or a 1:1 mixture of artemisinin and quinine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.054
• 作为产物：
  描述：

  奎宁 在 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 Jones's reagent 、 三乙胺 、 2,6-二氯苯甲酰氯 作用下， 以 二氯甲烷 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 (3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl 2-((3R,4S,6S)-6-((R)-((tert-butyldimethylsilyl)oxy)(6-methoxyquinolin-4-yl)methyl)quinuclidin-3-yl)acetate
  参考文献：
  名称：

  A novel artemisinin–quinine hybrid with potent antimalarial activity

  摘要：

  Artemisinin was reduced to dihydroartemisinin and coupled to a carboxylic acid derivative of quinine via an ester linkage. This novel hybrid molecule had potent activity against the 3D7 and (drug-resistant) FcB1 strains of Plasmodium falciparum? in culture. The activity was superior to that of artemisinin alone, quinine alone, or a 1:1 mixture of artemisinin and quinine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.054