(E)-5-methoxy-3-(3,4,5-trimethoxybenzylidene)-indolin-2-one | 872088-46-5

• 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: (E)-5-methoxy-3-(3,4,5-trimethoxybenzylidene)-indolin-2-one
• 英文别名: (3E)-6-methoxy-3-[(3,4,5-trimethoxyphenyl)methylidene]-1H-indol-2-one
• CAS: 872088-46-5
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: YLUHXAHNPQALMQ-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-5-methoxy-3-(3,4,5-trimethoxybenzylidene)-indolin-2-one 在 RPMI 1640 作用下， 以 二甲基亚砜 为溶剂， 反应 88.0h， 生成 (3Z)-6-methoxy-3-[(3,4,5-trimethoxyphenyl)methylidene]-1H-indol-2-one
  参考文献：
  名称：

  Structure–activity-relationship studies of conformationally restricted analogs of combretastatin A-4 derived from SU5416

  摘要：

  A series of combretastatin A-4 analogs derived from the ATP competitive, VEGF receptor tyrosine kinase inhibitor, SU5416 were synthesized. The cytotoxic effects of the analogs were evaluated against PC-3 and MDA-MB-231 cancer cell lines, as well as their abilities to inhibit tubulin polymerization. Results are compared to those of compound 1, our lead compound previously reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.017
• 作为产物：
  描述：

  3-甲氧基苯乙酸 在 copper(I) oxide 、 氯化亚砜 、 溴 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-5-methoxy-3-(3,4,5-trimethoxybenzylidene)-indolin-2-one
  参考文献：
  名称：

  铜催化的（E）-2-（2-溴苯基）-3-芳基丙烯酰胺的内酰胺化反应，用于合成（E）-3-亚芳基吲哚-2-酮

  摘要：

  已经开发了铜催化的（E）-2-（2-溴苯基）-3-芳基丙烯酰胺的无配体分子内C-N偶联。该方案为来自邻溴代苯乙酸和芳族或共轭烯基醛类的具有重要生物意义的（E）-3-芳基亚吲哚啉-2-酮提供了一种有效而实用的合成途径。易于获得的原料，温和无贵金属的条件，高效率以及对酚羟基的良好耐受性使该方法具有吸引力和适用性。

  DOI：

  10.1021/acs.joc.1c00452

文献信息

• Conformationally restricted analogs of Combretastatin A-4 derived from SU5416
  作者：Pui-Kai Li、Zili Xiao、Zhigen Hu、Bulbul Pandit、Yanjun Sun、Dan L. Sackett、Karl Werbovetz、Andrew Lewis、Jayasekar Johnsamuel

  DOI：10.1016/j.bmcl.2005.09.001

  日期：2005.12

  A series of compounds originally derived from the vascular endothelial growth factor receptor tyrosine kinase inhibitor, SU5416, was synthesized and evaluated. The most potent compound in this series, compound 7, structurally resembles the potent anti -microtubule agent Combretastatin A-4, inhibited tubulin polymerization, and showed potent growth inhibitory activities on both prostate and breast cancer lines with IC50 values in low to subnanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.
• Structure–activity-relationship studies of conformationally restricted analogs of combretastatin A-4 derived from SU5416
  作者：Bulbul Pandit、Yanjun Sun、Ping Chen、Dan L. Sackett、Zhigen Hu、Wendy Rich、Chenglong Li、Andrew Lewis、Kevin Schaefer、Pui-Kai Li

  DOI：10.1016/j.bmc.2006.06.017

  日期：2006.10

  A series of combretastatin A-4 analogs derived from the ATP competitive, VEGF receptor tyrosine kinase inhibitor, SU5416 were synthesized. The cytotoxic effects of the analogs were evaluated against PC-3 and MDA-MB-231 cancer cell lines, as well as their abilities to inhibit tubulin polymerization. Results are compared to those of compound 1, our lead compound previously reported. (c) 2006 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Lactamization of (<i>E</i>)-2-(2-Bromophenyl)-3-arylacrylamides for the Synthesis of (<i>E</i>)-3-Arylideneindolin-2-ones
  作者：Xiang Luo、Qianzhong Zhang、Yi Jiang、Chengxin Wang、Xianheng Song、Jianheng Li、Qinfang Yan、Albert S. C. Chan、Yong Zou

  DOI：10.1021/acs.joc.1c00452

  日期：2021.5.7

  A copper-catalyzed, ligand-free intramolecular C–N coupling of (E)-2-(2-bromophenyl)-3-arylacrylamides has been developed. This protocol provides an efficient and practical synthetic route for the biologically important (E)-3-arylideneindolin-2-ones from o-bromophenylacetic acids and aromatic or conjugated alkenyl aldehydes. Readily available starting materials, mild and noble metal-free conditions

  已经开发了铜催化的（E）-2-（2-溴苯基）-3-芳基丙烯酰胺的无配体分子内C-N偶联。该方案为来自邻溴代苯乙酸和芳族或共轭烯基醛类的具有重要生物意义的（E）-3-芳基亚吲哚啉-2-酮提供了一种有效而实用的合成途径。易于获得的原料，温和无贵金属的条件，高效率以及对酚羟基的良好耐受性使该方法具有吸引力和适用性。