4-[2-(3,5-二甲氧基苯基)乙基]苯酚 | 116518-94-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-[2-(3,5-二甲氧基苯基)乙基]苯酚
• 英文名称: 3,5-di-O-methyldihydroresveratrol
• 英文别名: 4-(3,5-dimethoxyphenethyl)phenol；dihydropterostilbene；4'-hydroxy-3,5-dimethoxy-bibenzyl；4-(3,5-Dimethoxy-phenaethyl)-phenol；4-[2-(3,5-Dimethoxyphenyl)ethyl]phenol
• CAS: 116518-94-6
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: WOOTZIKTRHIJPN-UHFFFAOYSA-N

物化性质

• 沸点：
  400.1±35.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  紫檀芪 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以83.6%的产率得到4-[2-(3,5-二甲氧基苯基)乙基]苯酚
  参考文献：
  名称：

  基于龙血中支架的成人海马神经发生有效刺激物的发现

  摘要：

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。

  DOI：

  10.1016/j.ejmech.2017.05.025

文献信息

• Resveratrol Derivatives and Their Role as Potassium Channels Modulators
  作者：F. Orsini、L. Verotta、M. Lecchi、R. Restano、G. Curia、E. Redaelli、E. Wanke

  DOI：10.1021/np0303153

  日期：2004.3.1

  a stilbenic or a bibenzylic skeleton have been prepared by partial synthesis from resveratrol and dihydroresveratrol. The synthesized compounds have been evaluated for their ability to modulate voltage-gated channels.

  通过白藜芦醇和二氢白藜芦醇的部分合成，已经制备了具有白藜芦醇或联苄骨架的一系列白藜芦醇（反式3，4'，5-三羟基lb）的Stilbenoid类似物。已经评估了合成化合物调节电压门控通道的能力。
• PREVENTION AND TREATMENT OF COLON CANCER
  申请人：Rimando Agnes M.

  公开号：US20120178704A1

  公开（公告）日：2012-07-12

  Stilbene compounds for the prevention and treatment of colon cancer or colon inflammation and methods of using same are provided.

  提供了用于预防和治疗结肠癌或结肠炎的双苯乙烯化合物及其使用方法。
• Identification of dihydrostilbenes in Pholidota chinensis as a new scaffold for GABAA receptor modulators
  作者：Diana C. Rueda、Angela Schöffmann、Maria De Mieri、Melanie Raith、Evelyn A. Jähne、Steffen Hering、Matthias Hamburger

  DOI：10.1016/j.bmc.2014.01.008

  日期：2014.2

  A dichloromethane extract of stems and roots of Pholidota chinensis (Orchidaceae) enhanced GABA-induced chloride currents (I-GABA) by 132.75 +/- 36.69% when tested at 100 mu g/mL in a two-micro-electrode voltage clamp assay, on Xenopus laevis oocytes expressing recombinant alpha(1)beta(2)gamma S-2 GABA(A) receptors. By means of an HPLC-based activity profiling approach, the three structurally related stilbenoids coelonin (1), batatasin III (2), and pholidotol D (3) were identified in the active fractions of the extract. Dihydrostilbene 2 enhanced I-GABA by 1512.19 +/- 176.47% at 300 mu M, with an EC50 of 52.51 +/- 16.96 mu M, while compounds 1 and 3 showed much lower activity. The relevance of conformational flexibility for receptor modulation by stilbenoids was confirmed with a series of 13 commercially available stilbenes and their corresponding semisynthetic dihydro derivatives. Dihydrostilbenes showed higher activity in the oocyte assay than their corresponding stilbenes. The dihydro derivatives of tetramethoxy-piceatannol (12) and pterostilbene (20) were the most active among these derivatives, but they showed lower efficiencies than compound 2. Batatasin III (2) showed high efficiency but no significant subunit specificity when tested on the receptor subtypes alpha(1)beta(2)gamma(2)s, alpha(2)beta(2)gamma(2)s, alpha(3)beta(2)gamma(2)s, alpha(4)beta(2)gamma(2)s, alpha(5)beta(2)gamma(2)s, alpha(1)beta(1)gamma(2)s, and alpha(1)beta(3)gamma(2)s. Dihydrostilbenes represent a new scaffold for GABAA receptor modulators. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARα
  作者：Cassia S. Mizuno、Guoyi Ma、Shabana Khan、Akshay Patny、Mitchell A. Avery、Agnes M. Rimando

  DOI：10.1016/j.bmc.2008.01.051

  日期：2008.4.1

  Pterostilbene, a naturally occurring analog of resveratrol, has previously shown PPAR alpha activation in H4IIEC3 cells and was found to decrease cholesterol levels in animals. In this study, analogs of pterostilbene were synthesized and their ability to activate PPARa was investigated. Among analogs that was synthesized (E)-4-(3,5-dimethoxystyryl) phenyl dihydrogen phosphate showed activity higher than pterostilbene and control drug ciprofibrate. Docking of the stilbenes inside PPARa showed the presence of important hydrogen bond interactions for PPAR alpha activation. (C) 2008 Elsevier Ltd. All rights reserved.
• WO2008/70872
  申请人：——

  公开号：——

  公开（公告）日：——