(E)-2-(3,4,5-trimethoxystyryl)benzofuran | 1415089-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (E)-2-(3,4,5-trimethoxystyryl)benzofuran
• 英文别名: (E)-2-(3,4,5-tri methoxystyryl)benzofuran；2-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]-1-benzofuran
• CAS: 1415089-12-1
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: KGQOYGBSVPZZNQ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘苯并呋喃 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-benzofuran 、 (E)-2-(3,4,5-trimethoxystyryl)benzofuran
  参考文献：
  名称：

  康他汀A-4苯并杂环衍生物的（Z）异构体的合成：几种方法的比较研究

  摘要：

  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。

  DOI：

  10.1016/j.tet.2013.01.005

文献信息

• COMBRETASTATIN ANALOGS
  申请人：PENTHALA Narsimha Reddy

  公开号：US20160068506A1

  公开（公告）日：2016-03-10

  The present invention relates novel heterocyclic analogs of combretastatin, their synthesis, and their use as anti-cancer compounds. In particular, compounds of Formula (I), Formula (II), and Formula (V) are provided.

  本发明涉及新型的杂环类似物，即康柏他静的衍生物，它们的合成以及它们作为抗癌化合物的用途。具体来说，提供了式(I)、式(II)和式(V)的化合物。
• Combretastatin analogs
  申请人：BioVentures, LLC

  公开号：US10100029B2

  公开（公告）日：2018-10-16

  The present invention relates novel heterocyclic analogs of combretastatin, their synthesis, and their use as anti-cancer compounds. In particular, compounds of Formula (I), Formula (II), and Formula (V) are provided.

  本发明涉及新的康瑞他汀杂环类似物、其合成及其作为抗癌化合物的用途。特别是提供了式(I)、式(II)和式(V)化合物。
• [EN] COMBRETASTATIN ANALOGS<br/>[FR] ANALOGUES DE LA COMBRÉTASTATINE
  申请人：UNIV ARKANSAS

  公开号：WO2014172363A3

  公开（公告）日：2014-12-31
• Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4
  作者：Thi Thanh Binh Nguyen、Thierry Lomberget、Ngoc Chau Tran、Evelyne Colomb、Lore Nachtergaele、Sylviane Thoret、Joëlle Dubois、Joren Guillaume、Rawad Abdayem、Marek Haftek、Roland Barret

  DOI：10.1016/j.bmcl.2012.09.047

  日期：2012.12

  A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis 3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis 3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.