(E)-4-methoxy-2',3,5'-trihydroxystilbene | 1335242-40-4

• 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: (E)-4-methoxy-2',3,5'-trihydroxystilbene
• 英文别名: 2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,4-diol
• CAS: 1335242-40-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: XDRRBFSAHVUUON-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异香兰素 在 三乙醇胺 、 potassium tert-butylate 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (E)-4-methoxy-2',3,5'-trihydroxystilbene
  参考文献：
  名称：

  白藜芦醇衍生的丁酰胆碱酯酶抑制剂

  摘要：

  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。

  DOI：

  10.1002/ardp.201300051

文献信息

• 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.
• 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。