(E)-3-hydroxy-2',4,4'-trimethoxystilbene | 1335242-41-5

• 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)-3-hydroxy-2',4,4'-trimethoxystilbene
• 英文别名: 5-[(E)-2-(2,4-dimethoxyphenyl)ethenyl]-2-methoxyphenol
• CAS: 1335242-41-5
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: FZSVYBYDYVAQRI-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二甲氧基碘苯 、 3-羟基-4-甲氧基苯乙烯 在 三乙醇胺 、 palladium diacetate 作用下， 反应 24.0h， 以54.7%的产率得到(E)-3-hydroxy-2',4,4'-trimethoxystilbene
  参考文献：
  名称：

  Synthesis and antimicrobial activity of (E) stilbene derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.07.015

文献信息

• 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.