3-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-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-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-2-one
• 英文别名: 3-hydroxy-3-(5-methyl-1H-indol-3-yl)-1H-indol-2-one
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: JNQVKONRBBFYIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-2-one 、 二环己胺 在 copper(l) iodide 、 苯甲酸 作用下， 反应 5.0h， 生成 1,1-dicyclohexyl-3-(2-(5-methyl-1H-indole-3-carbonyl)phenyl)urea
  参考文献：
  名称：

  铜（I）催化的靛红，吲哚和胺对不对称取代的2-羰基芳基脲的一锅反应

  摘要：

  通过一锅法使靛红与掺入伯氨基部分的吲哚反应，获得了一系列不对称的芳基脲，吲哚是伯胺部分，是重要的杂环骨架，具有多种药学活性结构。反应通过开环靛红的Cu（I）催化的C2 C3键进行，然后在最佳条件下使底物膨胀。此外，选择的化合物4b和4k表现出中等至良好的抗血吸虫活性。

  DOI：

  10.1016/j.tet.2018.02.019
• 作为产物：
  描述：

  5-甲基吲哚 、 靛红 在 吡啶 、 potassium carbonate 作用下， 反应 2.0h， 以94%的产率得到3-hydroxy-3-(5-methyl-1H-indol-3-yl)indolin-2-one
  参考文献：
  名称：

  铜（I）催化的靛红，吲哚和胺对不对称取代的2-羰基芳基脲的一锅反应

  摘要：

  通过一锅法使靛红与掺入伯氨基部分的吲哚反应，获得了一系列不对称的芳基脲，吲哚是伯胺部分，是重要的杂环骨架，具有多种药学活性结构。反应通过开环靛红的Cu（I）催化的C2 C3键进行，然后在最佳条件下使底物膨胀。此外，选择的化合物4b和4k表现出中等至良好的抗血吸虫活性。

  DOI：

  10.1016/j.tet.2018.02.019

文献信息

• Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation
  作者：Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2005.11.011

  日期：2006.2

  Ceric ammonium nitrate efficiently catalyzes the reaction of isatin with indoles under sonic waves to afford symmetrical 3,3-di(indolyl)indolin-2-ones in excellent yields, as well as the reaction of 3-hydroxy-3-indolylindolin-2-ones with indoles, pyrrole to afford the corresponding adducts in excellent yields, which provides an efficient route to the synthesis of symmetrical and unsymmetrical 3,3-

  硝酸铈铵在声波下能有效地催化Isatin与吲哚的反应，以优异的收率得到对称的3,3-二（吲哚基）吲哚-2-酮，以及3-羟基-3-吲哚基吲哚-2-的反应。对于带有吲哚的吡咯，吡咯以优异的产率提供相应的加合物，这为分别合成对称和不对称的3，3-二（吲哚基）吲哚-2-酮衍生物提供了有效的途径。
• Asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media
  作者：Ying Zhang、Shun-Yi Wang、Xiao-Ping Xu、Ran Jiang、Shun-Jun Ji

  DOI：10.1039/c3ob00045a

  日期：——

  Organocatalyzed asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media has been developed. The reactions proceeded efficiently in the presence of the MacMillan catalyst to give the desired products in good to excellent yields with moderate diastereoselectivities and excellent enantioselectivities.

  在水介质中开发了醛与 3-hydroxy-3-indolylox-indoles 的有机催化不对称δ-烷基化反应。在 MacMillan 催化剂的作用下，反应高效进行，以良好至极佳的产率、中等的非对映选择性和极佳的对映选择性得到了所需产物。
• “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.
• 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.
• Cu(I)-catalyzed one-pot reactions of isatins, indoles, and amines toward unsymmetrically substituted 2-carbonylarylureas
  作者：Xiangjun Peng、Xianyun Xu、Shuangyang Chen、Zeng Tian、Liangxian Liu、Qian Liu

  DOI：10.1016/j.tet.2018.02.019

  日期：2018.3

  A series of unsymmetrical arylureas was obtained by the one-pot method for reacting isatins with indoles incorporating primary amino moieties, a significant heterocyclic skeleton for diverse pharmaceutically active structures. The reaction proceeds through Cu(I)-catalyzed C2C3 bond of the ring-opening isatins and then expands the substrates in the optimum conditions. Furthermore, selected compounds

  通过一锅法使靛红与掺入伯氨基部分的吲哚反应，获得了一系列不对称的芳基脲，吲哚是伯胺部分，是重要的杂环骨架，具有多种药学活性结构。反应通过开环靛红的Cu（I）催化的C2 C3键进行，然后在最佳条件下使底物膨胀。此外，选择的化合物4b和4k表现出中等至良好的抗血吸虫活性。