1,2,3-Trimethoxy-5-[2-(4-nitro-phenyl)-vinyl]-benzene | 134029-66-6

• 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: 1,2,3-Trimethoxy-5-[2-(4-nitro-phenyl)-vinyl]-benzene
• 英文别名: (E)-1-nitro-4-[2-(3,4,5-trimethoxyphenyl)ethenyl]benzene；(E)-1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene；(E)-1-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)ethene；(E)-1,2,3-trimethoxy-5-(4-nitrostyryl)benzene；3,4,5-trimethoxy-4'-nitro-trans-stilbene；trans-3,4,5-trimethoxy-4'-nitrostilbene；(E)-3,4,5-Trimethoxy-4'-nitrostilbene；1,2,3-trimethoxy-5-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 134029-66-6
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: UDXWNMYENXAKPA-SNAWJCMRSA-N

物化性质

• 熔点：
  192-193 °C
• 沸点：
  445.3±40.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 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：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3-Trimethoxy-5-[2-(4-nitro-phenyl)-vinyl]-benzene 在 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 (E)-2-(4-(3,4,5-trimethoxystyryl)phenyl)benzo[d][1,2]selenazol-3(2H)-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.03.030
• 作为产物：
  描述：

  5-溴甲基-1,2,3-三甲氧基苯 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 1,2,3-Trimethoxy-5-[2-(4-nitro-phenyl)-vinyl]-benzene
  参考文献：
  名称：

  Synthesis and Bioactivity of Resveratrol Analogues

  摘要：

  据报道，白藜芦醇能够增强SIRT1的表达，并通过刺激与哺乳动物SIRT1具有高度同源性的Sir2，显著模拟热量限制的效果。设计并合成了系列新型白藜芦醇衍生物，作为新型SIRT1激动剂的候选物质。通过核磁共振(1H NMR)光谱分析对合成的化合物进行了表征，并利用Bioscreen C MBR机器在100 μM/L浓度下检测了这些化合物对酵母亲本菌株BY4743的Sir2激活作用。与白藜芦醇相比，多个化合物表现出良好的Sir2激活活性。同时，还讨论了这些化合物的结构-活性关系与Sir2激活活性的相关性。

  DOI：

  10.14233/ajchem.2014.16226

文献信息

• A Highly Stereoselective Synthesis of Stilbenes under Solvent-Free Conditions
  作者：Xia-Bing Li、Li Wang、Xi-Quan Zhang、Hong-Mei Gu、Jian Guo、Bao-Lin Li

  DOI：10.3184/030823410x12814419570511

  日期：2010.10

  A highly stereoselective synthesis of stilbenes ( trans-1,2-diarylethylenes) was achieved under solvent-free conditions from aryl-aldehydes and aromatic substances bearing an activated methyl group in the presence of anhydrous K₂CO₃ and poly(ethylene glycol). This method avoided the need for completely anhydrous condition and use of a noxious organic solvent.

  在无溶剂条件下，在无水 K2CO3 和聚（乙二醇）的存在下，从芳基醛和带有活化甲基的芳香物质中实现了高立体选择性合成二苯乙烯（反式-1,2-二乙烯基）。这种方法避免了在完全无水的条件下使用有毒的有机溶剂。
• 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。
• Microwave-Assisted Solvent-Free Synthesis of (<i>E</i>)-Stilbenes
  作者：Liu-chang Wang、Jiang Li、Xi-quan Zhang、Hong-mei Gu、Bao-lin Li

  DOI：10.3184/174751912x13320888894748

  日期：2012.4

  An efficient synthesis of a series of stilbenes is reported using 4-nitrotoluene and substituted arylaldehydes as starting materials in the presence of Cs₂CO₃ and polyethylene glycol under solvent-free microwave irradiation. Compared with conventional method, this strategy exhibited higher stereoselectivity, shorter reaction times and has a lower environmental impact.

  报告以 4-硝基甲苯和取代的芳基醛为起始原料，在 Cs2CO3 和聚乙二醇存在下，在无溶剂微波辐照条件下高效合成了一系列二苯乙烯类化合物。与传统方法相比，该策略具有更高的立体选择性、更短的反应时间和更低的环境影响。
• 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。
• Method of inhibiting amyloid protein aggregation and imaging amyloid deposits
  申请人：——

  公开号：US20040220235A1

  公开（公告）日：2004-11-04

  The present invention provides a method of treating Alzheimer's disease using a compound of Formula I 1 Also provided is a method of inhibiting the aggregation of amyloid proteins using a compound of Formula I and a method of imaging amyloid deposits, as well as new compounds of Formula I.

  本发明提供了一种利用I1式化合物治疗阿尔茨海默病的方法。还提供了一种利用I式化合物抑制淀粉样蛋白聚集的方法，以及一种成像淀粉样沉积物的方法，以及新的I式化合物。