(3R)-3-hydroxy-2-(2-nitroethyl)-4-((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)butanenitrile | 1447736-24-4

• 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)-3-hydroxy-2-(2-nitroethyl)-4-((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)butanenitrile
• CAS: 1447736-24-4
• 化学式: C₂₁H₃₂N₂O₇
• 分子量: 424.494
• InChiKey: GFEBAMLEFLZDCW-DBYLPECISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  124.08
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  10-deoxoallylartemisinin 在 三乙烯二胺 、 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 (3R)-3-hydroxy-2-(2-nitroethyl)-4-((3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)butanenitrile
  参考文献：
  名称：

  Synthesis of a novel series of highly functionalized Baylis–Hillman adducts of artemisinin with potent anticancer activity

  摘要：

  A novel series of densely functionalized derivatives of artemisinin have been synthesized using Baylis-Hillman reaction and their further applicability has been demonstrated. The in vitro anticancer activity of these adducts against a panel of human cancer cell lines is summarized. Compound 10 (% GI of 100 against colon colo-205; % GI of 85 against Lung A-549), 7b (% GI of 78 against prostrate PC-3) and 9a, 9b (% GI of 71 against prostrate PC-3) were especially potent in inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. These newly synthesized compounds can be further utilized as potential precursor for the synthesis of libraries of new artemisinin analogs including dimer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.123