(E)-1-(4-aminophenyl)-2-(3,4,5-trimethoxyphenyl)ethene | 134029-73-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(4-aminophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: (E)-4-(3,4,5-trimethoxystyryl)aniline；3,4,5-trimethoxy-4'-amino-trans-stilbene；(E)-4'-amino-3,4,5-trimethoxystilbene；4-[2-(3,4,5-Trimethoxy-phenyl)-vinyl]-phenylamine；4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]aniline
• CAS: 134029-73-5
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: MWXBWYJFAGYFKS-SNAWJCMRSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯乙基异氰酸酯 、 (E)-1-(4-aminophenyl)-2-(3,4,5-trimethoxyphenyl)ethene 以 二氯甲烷 为溶剂， 以68%的产率得到(E)-1-(2-chloroethyl)-3-(4-(3,4,5-trimethoxystyryl)phenyl)urea
  参考文献：
  名称：

  Styryl-N-phenyl-N′-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model

  摘要：

  Combretastatin A-4 (CA-4) is a well-studied and attractive molecular template to develop new antimitotics. Several thousand of modifications were performed on the ring B and the ethenyl bridge of CA-4 but only a few involved the trimethoxyphenyl moiety (TMP, ring A) often considered essential to the antiproliferative and antimicrotubule activities. In this study, we described the design, the preparation, the characterization and the biological evaluation of three new series of CA-4 analogs namely styryl-N-phenyl-N'-ethylureas (SEUs), styryl-N-phenyl-N'-(2-chloroethyl)ureas (SCEUs) and styrylphenylimidazolidin-2-ones (SIMZs) bearing a 3-Cl (series a), 3,5-Me (series b) and TMP (series c) substituents, respectively. All SCEU and SIMZ Z-isomers were active in the high and the low nanomolar range, respectively. Conversely to SEUs and their E-isomers that were significantly less active or inactive. Interestingly, the IMP moiety is giving rise to derivatives exhibiting the lowest antiproliferative activity in the SCEU series (10c) and the most active compound in the SIMZ series (12c). Moreover, SIMZ Z-isomers bearing either a 3-Cl (12a) or a 3,5-Me (12b) exhibited antiproliferative activities that are also in the same order of magnitude as 12c. All SCEU and SIMZ Z-isomers also arrested the cell cycle progression in G2/M phase, bound to the colchicine-binding site and disrupted the cytoskeleton of cancer cells. In addition to the promising and innovative microtubule-disrupting properties of SCEUs and SIMZs, these results show that the IMP moiety is not essential for the cytocidal activity of these new CA-4 analogs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.034
• 作为产物：
  描述：

  4-硝基苄基三苯基溴蓊盐 在 盐酸 、 铁粉 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 (E)-1-(4-aminophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
  参考文献：
  名称：

  Styryl-N-phenyl-N′-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model

  摘要：

  Combretastatin A-4 (CA-4) is a well-studied and attractive molecular template to develop new antimitotics. Several thousand of modifications were performed on the ring B and the ethenyl bridge of CA-4 but only a few involved the trimethoxyphenyl moiety (TMP, ring A) often considered essential to the antiproliferative and antimicrotubule activities. In this study, we described the design, the preparation, the characterization and the biological evaluation of three new series of CA-4 analogs namely styryl-N-phenyl-N'-ethylureas (SEUs), styryl-N-phenyl-N'-(2-chloroethyl)ureas (SCEUs) and styrylphenylimidazolidin-2-ones (SIMZs) bearing a 3-Cl (series a), 3,5-Me (series b) and TMP (series c) substituents, respectively. All SCEU and SIMZ Z-isomers were active in the high and the low nanomolar range, respectively. Conversely to SEUs and their E-isomers that were significantly less active or inactive. Interestingly, the IMP moiety is giving rise to derivatives exhibiting the lowest antiproliferative activity in the SCEU series (10c) and the most active compound in the SIMZ series (12c). Moreover, SIMZ Z-isomers bearing either a 3-Cl (12a) or a 3,5-Me (12b) exhibited antiproliferative activities that are also in the same order of magnitude as 12c. All SCEU and SIMZ Z-isomers also arrested the cell cycle progression in G2/M phase, bound to the colchicine-binding site and disrupted the cytoskeleton of cancer cells. In addition to the promising and innovative microtubule-disrupting properties of SCEUs and SIMZs, these results show that the IMP moiety is not essential for the cytocidal activity of these new CA-4 analogs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.034

文献信息

• A Highly Stereoselective Synthesis and Crystal Structure of (E)-4'-Amino-3,4,5- trimethoxystilbene
  作者：Xia-Bing Li、Xi-Quan Zhang、Hong-Mei Gu、Bao-Lin Li

  DOI：10.5012/jkcs.2011.55.2.251

  日期：2011.4.20

  3,4,5-Trimethoxybenzaldehyde과 p-nitrotoluene을 출발물질로 하여 두 단계 반응으로 (E)-4'-amino-3,4,5-trimethoxystilbene을 합성할 수 있는 합성 방법을 개발하였으며, 이 화합물에 대한 결정 구조를 X-ray 회절분석법으로 결정하였다. A new and highly stereoselective synthesis of (E)-4'-amino-3,4,5-trimethoxystilbene was achieved by using 3,4,5-trimethoxybenzaldehyde and p-nitrotoluene as starting materials through condensation under solvent-free condition and followed by the reducing of nitro group with the system of $NH_2NH_2/FeCl_3$/C in ethanol. The crystal structure of (E)-4'-amino-3,4,5-trimethoxystilbene was also determined by X-ray diffraction analysis.

  我们开发了一种新的合成方法，能够以3,4,5-三甲氧基苯甲醛和p-硝基甲苯为起始物，通过两步反应合成(E)-4'-氨基-3,4,5-三甲氧基芪，并利用X射线衍射分析法确定了该化合物的晶体结构。 一种新的、高度立体选择性的(E)-4'-氨基-3,4,5-三甲氧基芪的合成方法被实现，该方法使用3,4,5-三甲氧基苯甲醛和p-硝基甲苯作为起始材料，在无溶剂条件下进行缩合反应，随后在乙醇中使用$NH_2NH_2/FeCl_3$/C体系还原硝基。通过X射线衍射分析也确定了(E)-4'-氨基-3,4,5-三甲氧基芪的晶体结构。
• Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
  申请人：——

  公开号：US20030073712A1

  公开（公告）日：2003-04-17

  Cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.

  细胞保护化合物，其中许多是酚类衍生物，其特点是具有特定共轭键的取代酚，对于治疗某些缺血或炎症性疾病非常有用，包括但不限于中风、心肌梗死、充血性心力衰竭以及以炎症或氧化损伤为特征的皮肤疾病。它们还可用于制造用于治疗这些疾病的药物和化妆品配方。
• Stilbene derivatives as anticancer agents
  申请人：Research Corporation Technologies, Inc.

  公开号：US05430062A1

  公开（公告）日：1995-07-04

  The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds among those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.

  本发明涉及一种具有抗癌作用的苯乙烯衍生物。这些化合物可用于治疗易于通过其治疗的癌症，并可用于治疗这些癌症的方法中。本文还披露了含有这些化合物的制药组合物。在披露的化合物中，有三种优选的化合物，分别为(Z)-1-(4-甲氧基苯基)-2-(3,4,5-三甲氧基苯基)乙烯，(Z)-1-(4-甲基苯基)-2-(3,4,5-三甲氧基苯基)乙烯和4-甲基-3',4',5'-三甲氧基苯乙胺盐酸盐。
• 一种小分子NQO2抑制剂及其制备方法与应用
  申请人：山东大学

  公开号：CN115872870A

  公开（公告）日：2023-03-31

  本发明属于生物医药领域，涉及一种小分子NQO2抑制剂及其制备方法与应用。其为式(I)、(II)或(III)所示的化合物或其药学上可接受的盐， 本发明提供的小分子NQO2抑制剂具有靶点明确、结构新颖、活性效果突出和制备成本低廉等优势，可以作为针对肿瘤疾病的很有前景的化学预防剂。
• Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents
  作者：Jun Yan、Yueyan Guo、Yali Wang、Fei Mao、Ling Huang、Xingshu Li

  DOI：10.1016/j.ejmech.2015.03.030

  日期：2015.5

  To identify novel multi-target-directed drug candidates for the treatment of cancer, a series of benzoselenazole-stilbene hybrids were synthesised by combining the pharmacophores of resveratrol and ebselen. The biological assay indicated that all of the hybrids exhibited antiproliferative activities against four human cancer cell lines and demonstrated good TrxR inhibitory activities. The mechanism of cell apoptosis was investigated in G2/M cell cycle arrest induced by compound 6e and the apoptosis of the human liver carcinoma Bel-7402 cell line. The significant increase in intracellular ROS confirmed that compound 6e was capable of causing oxidative stress-induced apoptosis in cancer cells. Our results support the potential of compound 6e as a candidate for further studies examining the development of novel drugs for cancer treatment. (C) 2015 Elsevier Masson SAS. All rights reserved.