(3E)-1-methyl-3-[(3,4,5-trimethoxyphenyl)methylidene]indol-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: (3E)-1-methyl-3-[(3,4,5-trimethoxyphenyl)methylidene]indol-2-one
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: PLQNNZRIXIRLMP-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-iodophenyl)propiolamide 在 palladium diacetate sodium hydride 、 三苯基膦 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (3E)-1-methyl-3-[(3,4,5-trimethoxyphenyl)methylidene]indol-2-one
  参考文献：
  名称：

  Tandem Heck–Suzuki–Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4

  摘要：

  A series of compounds related to combretastatin A-4 has been synthesized by a tandem Heck-carbocyclization/Suzuki coupling process. From various alkynamides and 3,4,5-trimethoxyphenyl boronic acid or the corresponding styryl derivative, (E)-3-arylmethyleneoxindoles (type I) and (EE)-3-alkylideneoxindoles (type II) were efficiently obtained in a stereoselective manner. Factors influencing yield and stereoselectivity are detailed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.129

文献信息

• Antitumor Activity of Substituted <i>E</i>-3-(3,4,5-Trimethoxybenzylidene)-1,3-dihydroindol-2-ones
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Mark W. Kunkel

  DOI：10.1021/jm0607808

  日期：2006.11.1

  The design and synthesis of anticancer E-3-( 3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones is reported. Strong COMPARE correlations among the cell line responses suggest that these compounds may be acting similarly through a combination of different mechanisms of action. The 5-methoxy derivative ( 2h) was the most active compound with a mean pGI(50) of 6.34, and it is now under review by Biological Evaluation Committee of the National Cancer Institute for possible further studies.