1-benzyl-3,3-bis(1-(prop-2-ynyl)-1H-indol-3-yl)indolin-2-one | 1315235-15-4

• 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: 1-benzyl-3,3-bis(1-(prop-2-ynyl)-1H-indol-3-yl)indolin-2-one
• 英文别名: 1-Benzyl-3,3-bis(1-prop-2-ynylindol-3-yl)indolin-2-one；1-benzyl-3,3-bis(1-prop-2-ynylindol-3-yl)indol-2-one
• CAS: 1315235-15-4
• 化学式: C₃₇H₂₇N₃O
• 分子量: 529.641
• InChiKey: UHAJBGRHIMSVEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苄基-1H-吲哚-2,3-二酮 、 1-(2-丙炔)-1H-吲哚 在 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以87%的产率得到1-benzyl-3,3-bis(1-(prop-2-ynyl)-1H-indol-3-yl)indolin-2-one
  参考文献：
  名称：

  Zn(OTf)2-catalysed indolylation and pyrrolylation of isatins: Efficient synthesis and biochemical assay of 3,3-di(heteroaryl)oxindoles

  摘要：

  通过Zn(OTf)2催化的吲哚化和吡咯化反应，开发出一种高效且经济的3,3-双(吲哚基)氧吲哚和3,3-双(吡咯基)氧吲哚合成方法。在啮齿类动物模型中对合成的分子进行了初步的生化检测，以评估其血清谷氨酸草酰乙酸转氨酶和丙二醛水平。

  DOI：

  10.1007/s12039-013-0510-y

文献信息

• Practical synthesis, anticonvulsant, and antimicrobial activity of N -allyl and N -propargyl di(indolyl)indolin-2-ones
  作者：Chandrasekaran Praveen、Asairajan Ayyanar、Paramasivan Thirumalai Perumal

  DOI：10.1016/j.bmcl.2011.04.117

  日期：2011.7

  An operation friendly protocol for the synthesis of novel di(indolyl)indolin-2-ones via Cu(OTf)(2) catalyzed bis-addition of N-allyl and N-propargyl indole with isatin was developed. This methodology allowed us to achieve the products in excellent yields without requiring purification technique like column chromatography. All the synthesized compounds were evaluated for their in vivo anticonvulsant activity against maximal electroshock test. Six compounds showed maximum activity compared to the standard drug phenytoin. The scope of the new molecules as antimicrobial agents were tested against two bacterial strains (Staphylococcus aureus and Escherichia coli) and one fungal strain (Candida albicans). (C) 2011 Elsevier Ltd. All rights reserved.
• Zn(OTf)2-catalysed indolylation and pyrrolylation of isatins: Efficient synthesis and biochemical assay of 3,3-di(heteroaryl)oxindoles
  作者：C PRAVEEN、S NARENDIRAN、P DHEENKUMAR、P T PERUMAL

  DOI：10.1007/s12039-013-0510-y

  日期：2013.11

  An efficient and cheap synthetic approach to 3,3-di(indolyl)oxindoles and 3,3-di(pyrrolyl)oxindoles has been developed via Zn(OTf)2 catalysed indolylation and pyrrolylation of isatins. A preliminary biochemical assay of the synthesized molecules in rodent models were performed to estimate the serum glutamate oxaloacetate transaminase and malondialdehyde levels.

  通过Zn(OTf)2催化的吲哚化和吡咯化反应，开发出一种高效且经济的3,3-双(吲哚基)氧吲哚和3,3-双(吡咯基)氧吲哚合成方法。在啮齿类动物模型中对合成的分子进行了初步的生化检测，以评估其血清谷氨酸草酰乙酸转氨酶和丙二醛水平。