N-(β-L-rhamnopyranosyl)indirubin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(β-L-rhamnopyranosyl)indirubin
• 英文别名: (3Z)-3-(3-oxo-1H-indol-2-ylidene)-1-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]indol-2-one
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: AVXRSJWDLOZVBS-ZUYNXGORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  119.33
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  L-rhamnopyranose 在 吡啶 、 三氯化铝 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 29.5h， 生成 N-(β-L-rhamnopyranosyl)indirubin
  参考文献：
  名称：

  First synthesis of indirubin N-glycosides (red sugars)

  摘要：

  The first indirubin N-glycosides were prepared by reaction,of isatine N-glycosides with indoxyl acetate under basic conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.024

文献信息

• Synthesis of indirubin-N′-glycosides and their anti-proliferative activity against human cancer cell lines
  作者：Stefanie Libnow、Karen Methling、Martin Hein、Dirk Michalik、Manuela Harms、Kristian Wende、Anke Flemming、Martin Köckerling、Helmut Reinke、Patrick J. Bednarski、Michael Lalk、Peter Langer

  DOI：10.1016/j.bmc.2008.04.003

  日期：2008.5

  The first indirubin-N'-glycosides were prepared based on reactions of isatin-N'-glycosides with indoxyls. The products show a significant anti-proliferative activity against various human cancer cell lines. Good results were observed for an indirubin-N'- mannoside which was shown to have medium to high anti-proliferative activity against all investigated cell lines. The highest activities and selectivities against the MCF-7 breast cancer cell line were observed for indirubin-N'-rhamnosides. (C) 2008 Elsevier Ltd. All rights reserved.