3-(5-bromo-1H-indol-3-yl)-5-fluoro-3-hydroxyindolin-2-one | 916179-27-6

• 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-(5-bromo-1H-indol-3-yl)-5-fluoro-3-hydroxyindolin-2-one
• 英文别名: 3-(5-bromo-indol-3-yl)-5-fluoro-3-hydroxy-indolin-2-one；3-(5-bromo-1H-indol-3-yl)-5-fluoro-3-hydroxy-1H-indol-2-one
• CAS: 916179-27-6
• 化学式: C₁₆H₁₀BrFN₂O₂
• 分子量: 361.17
• InChiKey: XGSBCFSXBRSLHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 5-氟靛红 在 苄基三甲基氢氧化铵 作用下， 以 水 为溶剂， 反应 0.42h， 以85%的产率得到3-(5-bromo-1H-indol-3-yl)-5-fluoro-3-hydroxyindolin-2-one
  参考文献：
  名称：

  Triton B 辅助、高效且方便地在水性介质中合成 3-吲哚基-3-羟基羟吲哚

  摘要：

  在水性介质中，在 Triton B 存在下，靛红与吲哚反应，描述了一种有效且方便的 3-吲哚基-3-羟基羟吲哚合成。

  DOI：

  10.1080/00397910902916072

文献信息

• Triton B–Assisted, Efficient, and Convenient Synthesis of 3-Indolyl-3-hydroxy Oxindoles in Aqueous Medium
  作者：H. M. Meshram、D. Aravind Kumar、P. Ramesh Goud、B. Chennakesava Reddy

  DOI：10.1080/00397910902916072

  日期：2009.12.15

  An efficient and convenient synthesis of 3-indolyl-3-hydroxy oxindole is described by the reaction of isatin with indole in the presence of Triton B in an aqueous medium.

  在水性介质中，在 Triton B 存在下，靛红与吲哚反应，描述了一种有效且方便的 3-吲哚基-3-羟基羟吲哚合成。
• Treatment of protein folding disorders
  申请人：Carter D. Michael

  公开号：US20070015813A1

  公开（公告）日：2007-01-18

  In certain embodiments, the invention is directed to a method for treating a protein folding disorder comprising administering to a subject a compound of the formulas disclosed. In preferred embodiments, the compounds are bis-indole compounds.

  在某些实施例中，本发明涉及一种治疗蛋白质折叠紊乱的方法，包括向受试者给予公开的配方的化合物。在优选实施例中，这些化合物是双吲哚化合物。
• “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.
• Kaolin/KOH Is an Efficient Heterogeneous Catalyst for the Synthesis of 3-Hydroxy-3-indolyl Oxindoles
  作者：G. Srihari、M. Marthanda Murthy

  DOI：10.1080/00397911.2010.515342

  日期：2011.9.15

  3-Hydroxy-3-indolyl oxindoles were synthesized from isatins and indoles in good to excellent yields by using heterogeneous catalyst kaolin preloaded with KOH.
• 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.