5-methoxy-1-(3,4,5-trimethoxy)benzylindoline-2,3-dione | 1447364-18-2

• 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-methoxy-1-(3,4,5-trimethoxy)benzylindoline-2,3-dione
• 英文别名: 5-Methoxy-1-[(3,4,5-trimethoxyphenyl)methyl]indole-2,3-dione；5-methoxy-1-[(3,4,5-trimethoxyphenyl)methyl]indole-2,3-dione
• CAS: 1447364-18-2
• 化学式: C₁₉H₁₉NO₆
• 分子量: 357.363
• InChiKey: LJCUNLFNTURBCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-(3,4,5-trimethoxy)benzylindoline-2,3-dione 在 肼 作用下， 生成 5-methoxy-1-[(3,4,5-trimethoxyphenyl)methyl]-3H-indol-2-one
  参考文献：
  名称：

  Design, synthesis and biological studies of novel tubulin inhibitors

  摘要：

  A series of compounds originally derived from the vascular endothelial growth factor receptor tyrosine kinase inhibitor, SU5416, were synthesized and evaluated. The most potent compound in this series, compound 3, which 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 the low nanomolar range. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.078
• 作为产物：
  描述：

  5-甲氧基靛红 、 5-溴甲基-1,2,3-三甲氧基苯 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-methoxy-1-(3,4,5-trimethoxy)benzylindoline-2,3-dione
  参考文献：
  名称：

  Design, synthesis and biological studies of novel tubulin inhibitors

  摘要：

  A series of compounds originally derived from the vascular endothelial growth factor receptor tyrosine kinase inhibitor, SU5416, were synthesized and evaluated. The most potent compound in this series, compound 3, which 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 the low nanomolar range. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.078

文献信息

• Exploration of Some Thiazolidine-2,4-dione and 2-Oxoindoline Derivatives Incorporating 3,4,5-Trimethoxybenzyl Moiety as Novel Anticancer Agents
  作者：Le Cong Huan、Hai Pham-The、Huong Le-Thi-Thu、Tran Phuong Thao、Do Nguyet Que、Nguyen-Thu Trang、Phan Thi Phuong Dung、Minji Pyo、Sang-Bae Han、Nguyen Thi Thuan、Nguyen-Hai Nam

  DOI：10.2174/1570180814666170605122552

  日期：2018.3.12

  Thus, continuing effort is needed in developing CA-4 analogues with improved pharmacological properties. Methods: In this study, two series of thiazolidine-2,4-dione and 2-oxoindoline derivatives incorporating 3,4,5-trimethoxybenzyl scaffold were designed and synthesized as CA-4 analogues. Results: Numerous CA-4 analogues bearing thiazolidine-2,4-dione/2-oxoindoline have been synthesized. These compounds

  背景：Combrestastatin A-4（CA-4）是一种有效的抗肿瘤和抗血管生成天然物质，从Combretum aff骨中分离出来。在过去的二十年中，已经发现了许多CA-4衍生物。但是，这些衍生物均未达到临床阶段。因此，需要持续的努力来开发具有改善的药理学性质的CA-4类似物。 方法：在这项研究中，设计并合成了包含3,4,5-三甲氧基苄基支架的两个系列的噻唑烷-2,4-二酮和2-氧代吲哚啉衍生物作为CA-4类似物。 结果：已经合成了许多带有噻唑烷-2,4-二酮/ 2-氧代吲哚啉的CA-4类似物。这些化合物针对几种人类癌细胞系进行了评估。发现一系列5 / 7-取代的-1-（3,4,5-三甲氧基）苄基吲哚啉-2,3-二酮（2a-g）表现出明显的细胞毒性。尤其是带有5个溴取代基的化合物2d在测试的4种人类癌细胞系中表现出最佳活性，其IC50值以亚微克/毫升为单位。该化合物还显示出有效的微管