2-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,4-benzenediol | 1093198-83-4

• 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: 2-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,4-benzenediol
• 英文别名: (E)-2,4’,5-trihydroxystilbene；(E)-2-(4-hydroxystyryl)benzene-1,4-diol；trans-2,5,4′-trihydoxystilbene；(E)-2',4,5'-trihydroxystilbene；2-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,4-diol
• CAS: 1093198-83-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ORQPEHPLPTVVDX-DAFODLJHSA-N

物化性质

• 沸点：
  472.3±33.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,4-benzenediol 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到(E)-2-(4-hydroxystyryl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Hydroquinone–quinone oxidation by molecular oxygen: a simple tool for signal amplification through auto-generation of hydrogen peroxide

  摘要：

  信号放大方法对于各种诊断检测显然非常重要。我们开发了一种基于小分子的新型探针，这种探针在亚几何量的过氧化氢激活后会产生自动感应放大反应。信号是通过对苯二酚在分子氧的作用下氧化成相应的醌衍生物而产生的。这种氧化反应伴随着过氧化氢的形成，过氧化氢可进入扩增序列并启动新的诊断循环。生成的醌由供体-受体共轭对组成，并在不同的波长发出荧光，因此可以通过方便的荧光检测来监测其形成。

  DOI：

  10.1039/c3ob40962g
• 作为产物：
  描述：

  1,4-diethoxy-2-chloromethyl-benzene 在 aluminum (III) chloride 、 N,N-二甲基苯胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 2-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,4-benzenediol
  参考文献：
  名称：

  Stilbenoid衍生物作为强大的血管松弛药的体外研究和结构-活性关系分析：发现新的铅化合物

  摘要：

  血管舒张剂作为抗高血压药的发展很重要，因为它对血管肌肉产生快速直接的松弛作用。白藜芦醇（RV），作为最广泛研究的类雌二醇和先导化合物，通过多种信号途径诱导优异的血管舒张作用。在这项研究中，主要通过使用去氧肾上腺素（PE）预收缩的内皮完整分离的主动脉环来评估合成的反式-类类植物衍生物SB 1-8e的体外血管反应。本文中我们报道了反式-3,4,4'-三羟基sti （SB 8b）的最大弛豫（RRV的最大值）。本文还重点介绍了在1 H NMR中芳香族质子的独特裂解方式。

  DOI：

  10.1016/j.bioorg.2020.104239

文献信息

• A facile and rapid access to resveratrol derivatives and their radioprotective activity
  作者：Saori Uzura、Emiko Sekine-Suzuki、Ikuo Nakanishi、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1016/j.bmcl.2016.07.018

  日期：2016.8

  A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes

  基于芳基硼酸与苯乙烯的钯催化氧化Heck反应，然后以中等至良好的产率脱甲基，可以轻松快速地获得白藜芦醇衍生物。易于合成一系列具有各种官能团的白藜芦醇衍生物。还已经使用大鼠胸腺细胞评估了合成化合物的放射防护活性。结果表明，一些白藜芦醇衍生物有效地保护了胸腺细胞免受辐射诱导的细胞凋亡。
• Resveratrol Derived Butyrylcholinesterase Inhibitors
  作者：René Csuk、Sabrina Albert、Ralph Kluge、Dieter Ströhl

  DOI：10.1002/ardp.201300051

  日期：2013.7

  (E)‐stilbenes were synthesized by Mizoroki–Heck reactions and tested for their ability to inhibit the enzymes acetyl‐ and butyrylcholinesterase. Several of them are good inhibitors of butyrylcholinesterase; one of them carrying an extra fluorine substituent is a 94‐fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase.

  通过 Mizoroki-Heck 反应合成了新型多羟基化 (E)-二苯乙烯，并测试了它们抑制乙酰胆碱酯酶和丁酰胆碱酯酶的能力。其中一些是丁酰胆碱酯酶的良好抑制剂；其中一种带有额外氟取代基的丁酰胆碱酯酶抑制剂是乙酰胆碱酯酶抑制剂的 94 倍。
• Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450 from<i>Thermobifida fusca</i>YX
  作者：Ansgar Rühlmann、Dragutin Antovic、Thomas J. J. Müller、Vlada B. Urlacher

  DOI：10.1002/adsc.201601168

  日期：2017.3.20

  synthesis of (E)‐4,4′‐dihydroxystilbene via direct double hydroxylation of (E)‐stilbene. The construction of a triple mutant led to a more than six‐fold increased catalytic efficiency compared to the wild type enzyme. CYP154E1 and variants thereof accepted not only (E)‐stilbene but also possessed remarkable activity towards ortho‐ and meta‐substituted hydroxystilbenes leading to resveratrol, (E)‐2,4′‐dihydroxystilbene

  自从过去的几十年以来，植物中的白藜芦醇白藜芦醇因其广泛的药用特性而受到了公众和研究界的广泛关注。除白藜芦醇外，由于其他潜在的生物活性不同，对其他植物类芪也有越来越高的兴趣。为了满足对类胡萝卜素的不断增长的需求，需要替代和可持续的生产方法。我们确定了细胞色素P450单加氧酶154E1从嗜热裂孢菌YX（CYP154E1），使（合成ë）-4,4'- dihydroxystilbene通过（的直管型双羟化ësti二苯乙烯。与野生型酶相比，三重突变体的构建使催化效率提高了六倍以上。CYP154E1及其变体不仅接受（E）-二苯乙烯，而且对邻位和间位取代的羟基苯乙烯有明显的活性，导致白藜芦醇，（E）-2,4'-二羟基二苯乙烯，（E）-2,4'，5 -三羟基sti和（E）-3,4'-二羟基sti。蛋白质工程和甲基-β-环糊精作为底物增溶剂的结合，使产品效价高达4.2 g L -1，酶总周转数（TTN）高达20
• Synthesis and antimicrobial activity of (E) stilbene derivatives
  作者：Sabrina Albert、Ralf Horbach、Holger B. Deising、Bianka Siewert、René Csuk

  DOI：10.1016/j.bmc.2011.07.015

  日期：2011.9

  Plants use multiple defence mechanisms comprising both constitutive and inducible barriers to prevent entering of phytopathogenic micro-organisms. In many plant species one of the most efficient responses to combat attacking microbes is the rapid synthesis of antimicrobial low molecular weight phytoalexins, for example, resveratrol, 3,5,4'-trihydroxystilbene (1). Resveratrol and its natural derivatives, however, display only moderate antimicrobial effects. Nevertheless, resveratrol may be a useful lead structure for the chemical synthesis of antimicrobials. In this study, several series of stilbenes have been synthesized, starting from the aldehydes using Wittig reactions to access the corresponding styrenes that were subjected to Mizoroki-Heck reactions to yield the stilbenes in good yields. The stilbenes were tested in an agar diffusion assay against several bacteria and fungi. For some of these compounds the inhibiting zones for bacteria and fungi were comparable with those of the antibiotics tetracycline, streptomycin, ampicillin, or kanamycin, directed against prokaryotes, and nourseothricin or hygromycin controlling fungi, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of novel (E) stilbene-based antitumor agents
  作者：René Csuk、Sabrina Albert、Bianka Siewert、Stefan Schwarz

  DOI：10.1016/j.ejmech.2012.06.015

  日期：2012.8

  Several new (E) stilbenes were synthesized by a combination of a Wittig olefination followed by Mizoroki-Heck coupling reactions. These compounds were screened for antitumor activity in a panel of 8 human cancer cell lines by a colorimetric SRB assay. Several of these compounds exhibit strong cytotoxicity. The most active compound of this series showed an average IC50 value of 0.03 mu mol; it acts by apoptosis as shown by a dye-exclusion test, an extra acridine orange/ethidium bromide staining and DNA-laddering experiments. (C) 2012 Elsevier Masson SAS. All rights reserved.