5-fluoro-3-(5-fluoro-1H-indol-3-yl)-3-hydroxyindolin-2-one | 1360873-19-3

• 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: 5-fluoro-3-(5-fluoro-1H-indol-3-yl)-3-hydroxyindolin-2-one
• 英文别名: 5-fluoro-3-(5-fluoro-1H-indol-3-yl)-3-hydroxy-1H-indol-2-one
• CAS: 1360873-19-3
• 化学式: C₁₆H₁₀F₂N₂O₂
• 分子量: 300.264
• InChiKey: DFEUULWUVRJUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-3-(5-fluoro-1H-indol-3-yl)-3-hydroxyindolin-2-one 、 (1-phenylvinyl)carbamic acid benzyl ester 在 (S)-[3,3'-di(2-naphthyl)-1,1'-binaphthyl-2,2'-diyl]phosphoric acid 、 sodium sulfate 、 氢溴酸 作用下， 以 二氯甲烷 、 乙醇 、 水 为溶剂， 反应 8.0h， 以70%的产率得到
  参考文献：
  名称：

  面向核-结构的3-羟基羟吲哚的不对称有机催化取代：在对映体全合成（+）-叶硫代鸟氨酸中的应用

  摘要：

  具有建设性的东西：涉及3-羟基羟吲哚的标题反应可生成3,3'-二取代的羟吲哚，并伴随以高收率和优异的对映选择性生成全碳季立体中心。该反应实现了六氢吡咯并吲哚骨架的对映选择性构建和（+）-叶黄嘌呤的第一个催化对映选择性全合成。

  DOI：

  10.1002/anie.201107079
• 作为产物：
  描述：

  5-氟吲哚 、 5-氟靛红 在 二乙醇胺 作用下， 以 水 为溶剂， 以92%的产率得到5-fluoro-3-(5-fluoro-1H-indol-3-yl)-3-hydroxyindolin-2-one
  参考文献：
  名称：

  “On water” expedient synthesis of 3-indolyl-3-hydroxy oxindole derivatives and their anticancer activity in vitro

  摘要：

  A series of 3-indolyl-3-hydroxy oxindole derivatives (n = 41) were synthesized by the green aminocatalytic method with excellent yields under mild reaction conditions. All the newly synthesized derivatives were subjected to evaluate their cytotoxic properties against different human cancer cell lines. Results indicated that about 73% of the derivatives exhibited significant anti-proliferative activities against leukemia (U937, THP-1), lung (A549) and breast cancer (MCF7) cell lines. Among them a few of the derivatives exhibited the most potent and effective cytotoxic activities on U937 (34, 36, 38 and 41) and MCF7 (12, 35, 40 and 41) cell lines, and their anti-proliferation activities are better than the positive control, Etoposide.

  DOI：

  10.1016/j.ejmech.2014.07.004

文献信息

• “On water” expedient synthesis of 3-indolyl-3-hydroxy oxindole derivatives and their anticancer activity in vitro
  作者：Parvathaneni Sai Prathima、Pamanji Rajesh、Janapala Venkateswara Rao、Uppalapati Sai Kailash、Balasubramanian Sridhar、Mandapati Mohan Rao

  DOI：10.1016/j.ejmech.2014.07.004

  日期：2014.9

  A series of 3-indolyl-3-hydroxy oxindole derivatives (n = 41) were synthesized by the green aminocatalytic method with excellent yields under mild reaction conditions. All the newly synthesized derivatives were subjected to evaluate their cytotoxic properties against different human cancer cell lines. Results indicated that about 73% of the derivatives exhibited significant anti-proliferative activities against leukemia (U937, THP-1), lung (A549) and breast cancer (MCF7) cell lines. Among them a few of the derivatives exhibited the most potent and effective cytotoxic activities on U937 (34, 36, 38 and 41) and MCF7 (12, 35, 40 and 41) cell lines, and their anti-proliferation activities are better than the positive control, Etoposide.
• Core-Structure-Oriented Asymmetric Organocatalytic Substitution of 3-Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)-Folicanthine
  作者：Chang Guo、Jin Song、Jian-Zhou Huang、Peng-Hao Chen、Shi-Wei Luo、Liu-Zhu Gong

  DOI：10.1002/anie.201107079

  日期：2012.1.23

  yield and excellent enantioselectivity. This reaction enabled the enantioselective construction of hexahydropyrroloindole skeletons and the first catalytic enantioselective total synthesis of (+)‐folicanthine.

  具有建设性的东西：涉及3-羟基羟吲哚的标题反应可生成3,3'-二取代的羟吲哚，并伴随以高收率和优异的对映选择性生成全碳季立体中心。该反应实现了六氢吡咯并吲哚骨架的对映选择性构建和（+）-叶黄嘌呤的第一个催化对映选择性全合成。