(E)-1-hydroxy-2-(2-methoxy)styrylbenzene | 89122-68-9

• 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-hydroxy-2-(2-methoxy)styrylbenzene
• 英文别名: (E)-2-(2-methoxystyryl)phenol；2-[(E)-2-(2-methoxyphenyl)ethenyl]phenol
• CAS: 89122-68-9
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: ACYGWOLSXFBZMR-ZHACJKMWSA-N

物化性质

• 熔点：
  105-106 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  375.2±11.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-hydroxy-2-(2-methoxy)styrylbenzene 在 氢氧化钾 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 11.0h， 生成 4-[2-[(E)-2-(2-methoxyphenyl)ethenyl]phenoxy]-N,N-dimethylbutan-1-amine
  参考文献：
  名称：

  取代的（ω-氨基烷氧基）二苯乙烯衍生物作为一类新的抗惊厥药。

  摘要：

  已合成了一系列取代的（ω-氨基烷氧基）二苯乙烯衍生物，并筛选了其抗惊厥活性。已经系统地检查了这些分子的结构修饰对活性的影响。2- [4-（4-甲基-1哌嗪基）丁氧基] sti烯（20）和某些2- [4-（3-烷氧基-1-哌啶基）丁氧基] sti烯衍生物（21，37， 38和40），通过最大电击惊厥（MES）和戊四氮诱发的小鼠惊厥试验确定。在大鼠的进一步药理试验中，化合物21的抗MES活性比二苯乙内酰脲和卡马西平更强，其治疗指数优于两种抗癫痫药。

  DOI：

  10.1021/jm00371a015
• 作为产物：
  描述：

  2-甲氧基溴苄 在 18-冠醚-6 、 sodium methylate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 (E)-1-hydroxy-2-(2-methoxy)styrylbenzene
  参考文献：
  名称：

  Synthesis, Antitumor Evaluation, and Apoptosis-Inducing Activity of Hydroxylated (E)-Stilbenes

  摘要：

  The parallel solution-phase synthesis of a series of 30 monohydroxylated (E)-stilbene analogues is described. In vitro screening revealed low micromolar activity (GI(50)) against the MDA MB 468 breast cancer cell line. Activity in MDA MB 468 cells correlated with the ability to induce apoptosis following drug treatment by the most potent agents in the series, e.g., 5dy and 5jy, an observation further reinforced by AnnexinV-FITC analysis and fluorescence microscopy.

  DOI：

  10.1021/jm049238e

文献信息

• An Efficient Method to Synthesize Benzofurans and Naphthofurans
  作者：Zhiyong Wang、Chongfeng Pan、Jie Yu、Yuqing Zhou、Ming-Ming Zhou

  DOI：10.1055/s-2006-944204

  日期：2006.7

  A new method for synthesis of benzofurans and naphthofurans from 2-hydroxystilbene derivatives via an intermolecular ­cyclization is reported in this study with up to 94% isolated yield.

  本研究报道了一种通过分子间环化反应从2-羟基二苯乙烯衍生物合成苯并呋喃和萘并呋喃的新方法，分离产率高达94%。
• Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes
  作者：Rosa Martí-Centelles、Eva Falomir、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.ejmech.2015.09.014

  日期：2015.10

  A group of thirty-nine stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity, as well as for their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and to downregulate the expression of the VEGF, hTERT and c-Myc genes, the two latter involved in the control of the activation of telomerase. One of the synthetic stilbenes, (E)-4-(4-methoxystyryl)aniline, showed strong cytotoxicity and proved able to cause a marked decrease both in the secretion of VEGF and in the expression of the hTERT and c-Myc genes, in all cases at concentrations in the low nanomolar range. (C) 2015 Elsevier Masson SAS. All rights reserved.