5-fluoro-3-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-2-one | 1396026-86-0

• 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-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-2-one
• 英文别名: 5-fluoro-3-hydroxy-3-(5-methyl-1H-indol-3-yl)-1H-indol-2-one
• CAS: 1396026-86-0
• 化学式: C₁₇H₁₃FN₂O₂
• 分子量: 296.301
• InChiKey: LTZJTCCJPAQEIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluoro-3-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-2-one 、 2-[(4-甲氧基苯基)甲氧基]乙醛 在 三氟乙酸 、 DL-脯氨酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 2-(5-fluoro-5'-methyl-2-oxo-3,3'-biindol-3-yl)-2-(4-methoxybenzyloxy)acetaldehyde
  参考文献：
  名称：

  通过醛的α-烷基化导致六氢吡咯并吲哚的对映选择性有机催化结构，从而合成（+）-胶质环丙素C

  摘要：

  12步程序：金鸡纳生物碱基胺和手性磷酸的组合使用可使3-羟基羟吲哚与醛的不对称烷基化反应产生极佳的对映选择性的3,3'-二取代的羟吲哚，从而可以实现（ +）-神经胶蛋白C从3-羟基羟吲哚起12步，总收率19％（参见方案; PMB =对-甲氧基苄基）。

  DOI：

  10.1002/chem.201204522
• 作为产物：
  描述：

  5-氟靛红 、 5-甲基吲哚 在 二乙醇胺 作用下， 以 水 为溶剂， 以92%的产率得到5-fluoro-3-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-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

• Preparation, characterization, and catalysis application of nano-rods zinc oxide in the synthesis of 3-indolyl-3-hydroxy oxindoles in water
  作者：Mona Hosseini-Sarvari、Mina Tavakolian

  DOI：10.1016/j.apcata.2012.07.009

  日期：2012.10

  ZnO nano-rods is synthesized successfully by a new method employing Zn(OAc)(2)center dot 2H(2)O. NH3 and polyethylene glycol (PEG, M-w = 2000). X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and BET surface area measurement were used to characterize the structure and morphology of the catalyst. Nano-rods ZnO has been found highly effective and recyclable catalyst for synthesis of 3-indolyl-3-hydroxy oxindole derivatives by Friedel-Crafts reaction of indole with isatins in excellent yields, in water. (C) 2012 Elsevier B.V. All rights reserved.
• “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.
• Enantioselective Organocatalytic Construction of Hexahydropyrroloindole by Means of α‐Alkylation of Aldehydes Leading to the Total Synthesis of (+)‐Gliocladin C
  作者：Jin Song、Chang Guo、Arafate Adele、Hao Yin、Liu‐Zhu Gong

  DOI：10.1002/chem.201204522

  日期：2013.3.4

  12‐Step program: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3‐hydroxyoxindoles with aldehydes to give 3,3′‐disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)‐gliocladin C in 12 steps from 3‐hydroxyoxindole with 19 % overall yield (see scheme; PMB=para‐methoxybenzyl)

  12步程序：金鸡纳生物碱基胺和手性磷酸的组合使用可使3-羟基羟吲哚与醛的不对称烷基化反应产生极佳的对映选择性的3,3'-二取代的羟吲哚，从而可以实现（ +）-神经胶蛋白C从3-羟基羟吲哚起12步，总收率19％（参见方案; PMB =对-甲氧基苄基）。