(E)-2-(3,4,5-trimethoxystyryl)-1H-indole | 1422647-66-2

• 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: (E)-2-(3,4,5-trimethoxystyryl)-1H-indole
• 英文别名: 2-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]-1H-indole
• CAS: 1422647-66-2
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: NRQPBQQHZMXPRE-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 三苯基-(3,4,5-三甲氧基-苄基)-溴化膦 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (E)-2-(3,4,5-trimethoxystyryl)-1H-indole
  参考文献：
  名称：

  Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents

  摘要：

  Heteroaromatic analogs of DMU-212 (8-15) have been synthesized and evaluated for their anti-cancer activity against a panel of 60 human cancer cell lines. These novel analogs contain a trans-3,4,5-trimethoxystyryl moiety attached to the C2 position of indole, benzofuran, benzothiazole or benzothiophene ring (8, 11, 13 and 14, respectively) and showed potent growth inhibition in 85% of the cancer cell lines examined, with GI(50) values <1 mu M. Interestingly, trans-3,4-and trans-3,5-dimethoxystyryl DMU-212 analogs 9, 10, 12 and 15 exhibited significantly less growth inhibition than their 3,4,5-trimethoxystyryl counterparts, suggesting that the trans-3,4,5-trimethoxystyryl moiety is an essential structural element for the potent anti-cancer activity of these heterocyclic DMU-212 analogs. Molecular modeling studies showed that the four most active compounds (8, 11, 13 and 14) all bind to the colchicine binding site on tubulin, and that their binding modes are similar to that of DMU-212. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.019

文献信息

• Synthesis of (Z) isomers of benzoheterocyclic derivatives of combretastatin A-4: a comparative study of several methods
  作者：Thi Thanh Binh Nguyen、Thierry Lomberget、Ngoc Chau Tran、Roland Barret

  DOI：10.1016/j.tet.2013.01.005

  日期：2013.3

  monobromoalkene, a combination of hydrosilylation/vinylsilane hydrolysis and a palladium-catalyzed semi-hydrogenation step, using DMF/KOH as the hydrogen source. Our studies led us to prepare a series of diarylacetylene derivatives via a Sonogashira coupling reaction, and also to find out a copper-free basic cyclization leading to benzo[b]thiophenes. The final choice for the synthesis method of 1 strongly depends

  研究了几种制备（Z）三甲氧基苯乙烯衍生物1的方法。在发现Wittig反应导致不满意的结果后，考虑了三种不同的策略：使用DMF / KOH作为氢源的Suzuki偶联与立体定义的单溴烯烃，氢化硅烷化/乙烯基硅烷水解和钯催化的半氢化步骤的组合。我们的研究使我们通过Sonogashira偶联反应制备了一系列二芳基乙炔衍生物，并且发现了无铜的碱性环化反应，从而生成了苯并[ b ]噻吩。1的合成方法的最终选择 强烈依赖于目标化合物，但通常应优先选择避免使用有毒锡还原剂的半氢化反应。
• Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents
  作者：Narsimha Reddy Penthala、Shraddha Thakkar、Peter A. Crooks

  DOI：10.1016/j.bmcl.2015.05.019

  日期：2015.7

  Heteroaromatic analogs of DMU-212 (8-15) have been synthesized and evaluated for their anti-cancer activity against a panel of 60 human cancer cell lines. These novel analogs contain a trans-3,4,5-trimethoxystyryl moiety attached to the C2 position of indole, benzofuran, benzothiazole or benzothiophene ring (8, 11, 13 and 14, respectively) and showed potent growth inhibition in 85% of the cancer cell lines examined, with GI(50) values <1 mu M. Interestingly, trans-3,4-and trans-3,5-dimethoxystyryl DMU-212 analogs 9, 10, 12 and 15 exhibited significantly less growth inhibition than their 3,4,5-trimethoxystyryl counterparts, suggesting that the trans-3,4,5-trimethoxystyryl moiety is an essential structural element for the potent anti-cancer activity of these heterocyclic DMU-212 analogs. Molecular modeling studies showed that the four most active compounds (8, 11, 13 and 14) all bind to the colchicine binding site on tubulin, and that their binding modes are similar to that of DMU-212. (C) 2015 Elsevier Ltd. All rights reserved.