3-[1-(2-Chloro-5-hydroxy-1H-indol-3-yl)-meth-(E)-ylidene]-1,3-dihydro-indol-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[1-(2-Chloro-5-hydroxy-1H-indol-3-yl)-meth-(E)-ylidene]-1,3-dihydro-indol-2-one
• 英文别名: 3-(2-Chloro-5-hydroxy-1H-indol-3-ylmethylene)-1,3-dihydro-indol-2-one；(3E)-3-[(2-chloro-5-hydroxy-1H-indol-3-yl)methylidene]-1H-indol-2-one
• 化学式: C₁₇H₁₁ClN₂O₂
• 分子量: 310.74
• InChiKey: KUWIIHSTSPFZQQ-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吲哚酮 、 2-chloro-5-hydroxyindol-3-carboxaldehyde 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 3-[1-(2-Chloro-5-hydroxy-1H-indol-3-yl)-meth-(E)-ylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and Antitumor Activity of 1,5,6-Substituted E-3-(2-Chloro-3-indolylmethylene)-1,3-dihydroindol-2-ones

  摘要：

  Synthesis and antitumor activity of new E-3-(2-chloro-3-indolylmethylene)-1,3-dihydroindol-2-ones are described. All compounds prepared were active in the primary test (three human cell lines) and entered the second level (60 human cell lines). The most active antitumor derivatives bear the same substituents in the chloroindole ring and are not CDK1 inhibitors. A COMPARE analysis showed that they could act as tubulin binders. In most cell lines, E-3-(2-chloro-5-methoxy-6-methyl-3-indolylmethylene)-1,3-dihydroindol-2-one was a growth inhibitor more potent than vincristine.

  DOI：

  10.1021/jm011123c

文献信息

• Synthesis and Antitumor Activity of 1,5,6-Substituted <i>E</i>-3-(2-Chloro-3-indolylmethylene)-1,3-dihydroindol-2-ones
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Vida Garaliene

  DOI：10.1021/jm011123c

  日期：2002.6.1

  Synthesis and antitumor activity of new E-3-(2-chloro-3-indolylmethylene)-1,3-dihydroindol-2-ones are described. All compounds prepared were active in the primary test (three human cell lines) and entered the second level (60 human cell lines). The most active antitumor derivatives bear the same substituents in the chloroindole ring and are not CDK1 inhibitors. A COMPARE analysis showed that they could act as tubulin binders. In most cell lines, E-3-(2-chloro-5-methoxy-6-methyl-3-indolylmethylene)-1,3-dihydroindol-2-one was a growth inhibitor more potent than vincristine.