5,6-dimethoxy-2-(4-methoxyphenyl)indole

• 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: 5,6-dimethoxy-2-(4-methoxyphenyl)indole
• 英文别名: 5,6-dimethoxy-2-(4-methoxyphenyl)-1H-indole
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: RDKVYRUXXLYTDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-2-(4-methoxyphenyl)indole 在 碘 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以88%的产率得到5,6,5',6'-tetramethoxy-2,2'-bis-(4-methoxyphenyl)-1H,1'H-[3,3']biindolyl
  参考文献：
  名称：

  3-芳基苯并呋喃、3-芳基苯并噻吩、2-芳基吲哚及其二聚体的简便合成

  摘要：

  摘要 描述了3-芳基苯并呋喃和苯并噻吩及其2-位二聚体和2-芳基吲哚及其3-位二聚体的制备。图形概要

  DOI：

  10.1080/00397911.2019.1611856
• 作为产物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 、 3,4-二甲氧基苯胺 在 N,N-二甲基苯胺 作用下， 反应 0.75h， 以46%的产率得到5,6-dimethoxy-2-(4-methoxyphenyl)indole
  参考文献：
  名称：

  3-芳基苯并呋喃、3-芳基苯并噻吩、2-芳基吲哚及其二聚体的简便合成

  摘要：

  摘要 描述了3-芳基苯并呋喃和苯并噻吩及其2-位二聚体和2-芳基吲哚及其3-位二聚体的制备。图形概要

  DOI：

  10.1080/00397911.2019.1611856

文献信息

• Methoxy-Substituted 3-Formyl-2-phenylindoles Inhibit Tubulin Polymerization
  作者：Robert Gastpar、Michael Goldbrunner、Doris Marko、Erwin von Angerer

  DOI：10.1021/jm980228l

  日期：1998.12.1

  The aim of this study was the identification of the essential structural elements in the 12-formyl-5,6-dihydroindolo[2,1-a]isoquinoline system required for the inhibition of tubulin polymerization which is understood to be the predominant mode of action of this class of cytostatics. Since 2-phenylindole forms the main fragment of this tetracycle, it was used as the basic structure and modified with respect to the number and positions of the oxygen functions in the aromatic rings. Further modifications related to the nitrogen, which was both replaced by oxygen and sulfur and alkylated. All derivatives were tested for cytostatic activity in human breast cancer cells (MDA-MB 231, MCF-7) and inhibition of tubulin polymerization. The spectrum of activity ranged from inactive to IC50 values of 35 nM (cell growth inhibition) and 1.5 mu M (tubulin polymerization), respectively, for the most active derivative 3e (3-formyl-6-methoxy-2-(4-methoxyphenyl)indole). Although the correlation between antiproliferative activity and inhibition of tubulin polymerization was not very pronounced, all of the potent cytostatic agents in this study disrupted microtubule assembly completely at the standard concentration of 40 mu M. By fluorescence microscopy it was demonstrated that the derivative 3e degrades the cytoskeleton in a similar fashion as colchicine does leading to the condensation of the microtubules around the nucleus after treatment. The comparison between hydroxy and methoxy derivatives revealed st striking difference between the 2-phenylindole derivatives and the indoloisoquinolines. In the 2-phenylindole series, the methoxy compounds were much more effective than the free phenols, whereas in the tetracyclic system the effect of the hydroxy derivatives exceeded that of the methylated compounds by I order of magnitude. Preliminary studies on the binding mode showed that both the 2-phenylindole derivatives and the indoloisoquinolines bind to the colchicine site on tubulin.
• Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers
  作者：Pailla Umareddy、Veera Reddy Arava

  DOI：10.1080/00397911.2019.1611856

  日期：2019.9.2

  Abstract The preparation of 3-aryl benzofuran and benzothiophenes and their dimers at 2-position and, 2-aryl indoles and their 3-position dimers preparation is described. Graphical Abstract

  摘要 描述了3-芳基苯并呋喃和苯并噻吩及其2-位二聚体和2-芳基吲哚及其3-位二聚体的制备。图形概要