(E)-4,4'-dihydroxy-3'-(hydroxycarbonyl)stilbene

• 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)-4,4'-dihydroxy-3'-(hydroxycarbonyl)stilbene
• 英文别名: (E)-2-hydroxy-5-[2-(4-hydroxyphenyl)-vinyl]-benzoic acid；2-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]benzoic acid；2-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoic acid
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: NQJNFLIEJNBROH-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4,4'-dihydroxy-3'-(hydroxycarbonyl)stilbene 、 乙酸酐 在 吡啶 作用下， 以76%的产率得到(E)-4,4'-diacetoxy-3'-(hydroxycarbonyl)stilbene
  参考文献：
  名称：

  Design and synthesis of resveratrol–salicylate hybrid derivatives as CYP1A1 inhibitors

  摘要：

  Resveratrol and aspirin are known to exert potential chemopreventive effects through modulation of numerous targets. Considering that the CYP450 system is responsible for the activation of environmental procarcinogens, the aim of this study was to design a new class of hybrid resveratrol-aspirin derivatives possessing the stilbene and the salicylate scaffolds. Using HepG2 cells, we evaluated (a) the inhibition of TCDD-mediated induction of CYP1A1 exerted by resveratrol-aspirin derivatives using the EROD assay, and (b) CYP1A1 mRNA in vitro. We observed significant inhibition (84%) of CYP1A1 activity and a substantial decrease in CYP1A1 mRNA with compound 3, compared to control. Resveratrol did not exert inhibition under the same experimental conditions. This inhibitory profile was supported by docking studies using the crystal structure of human CYP1A1. The potential effect exerted by compound 3 (the most active), provide preliminary evidence supporting the design of hybrid molecules combining the chemical features of resveratrol and aspirin.

  DOI：

  10.3109/14756366.2014.979347
• 作为产物：
  描述：

  4-甲氧基苄基三苯基膦溴化盐 在 正丁基锂 、 三溴化硼 、 二苯二硫醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-4,4'-dihydroxy-3'-(hydroxycarbonyl)stilbene
  参考文献：
  名称：

  Design and synthesis of resveratrol–salicylate hybrid derivatives as CYP1A1 inhibitors

  摘要：

  Resveratrol and aspirin are known to exert potential chemopreventive effects through modulation of numerous targets. Considering that the CYP450 system is responsible for the activation of environmental procarcinogens, the aim of this study was to design a new class of hybrid resveratrol-aspirin derivatives possessing the stilbene and the salicylate scaffolds. Using HepG2 cells, we evaluated (a) the inhibition of TCDD-mediated induction of CYP1A1 exerted by resveratrol-aspirin derivatives using the EROD assay, and (b) CYP1A1 mRNA in vitro. We observed significant inhibition (84%) of CYP1A1 activity and a substantial decrease in CYP1A1 mRNA with compound 3, compared to control. Resveratrol did not exert inhibition under the same experimental conditions. This inhibitory profile was supported by docking studies using the crystal structure of human CYP1A1. The potential effect exerted by compound 3 (the most active), provide preliminary evidence supporting the design of hybrid molecules combining the chemical features of resveratrol and aspirin.

  DOI：

  10.3109/14756366.2014.979347

文献信息

• Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases
  申请人：Wong C.W. Norman

  公开号：US20060205792A1

  公开（公告）日：2006-09-14

  The present disclosure provides non-naturally occurring polyphenol compounds that upregulate the expression of Apolipoprotein A-I (ApoA-I). The disclosed compositions and methods can be used for treatment and prevention of cardiovascular disease and related disease states, including cholesterol or lipid related disorders, such as, e.g., atherosclerosis.

  本公开提供了一些非天然的多酚化合物，这些化合物可以上调载脂蛋白A-I（ApoA-I）的表达。所述的组合物和方法可用于治疗和预防心血管疾病及相关疾病状态，包括胆固醇或脂质相关紊乱，例如动脉粥样硬化。
• Stilbenes and Chalcones for the Prevention and Treatment of Cardiovascular Diseases
  申请人：Wong Norman C.W.

  公开号：US20110082176A1

  公开（公告）日：2011-04-07

  The present disclosure provides non-naturally occurring polyphenol compounds that upregulate the expression of Apolipoprotein A-I (ApoA-I). The disclosed compositions and methods can be used for treatment and prevention of cardiovascular disease and related disease states, including cholesterol or lipid related disorders, such as, e.g., atherosclerosis.

  本公开提供非自然产生的多酚化合物，可以上调载脂蛋白A-I（ApoA-I）的表达。所披露的组合物和方法可用于治疗和预防心血管疾病和相关疾病状态，包括胆固醇或脂质相关的疾病，例如动脉粥样硬化。
• WO2006/45010
  申请人：——

  公开号：——

  公开（公告）日：——
• Stilbene analogs as inducers of apolipoprotein-I transcription
  作者：Henrik C. Hansen、Fabrizio S. Chiacchia、Reena Patel、Norman C.W. Wong、Vladimir Khlebnikov、Renata Jankowska、Kalpesh Patel、M. Madhava Reddy

  DOI：10.1016/j.ejmech.2009.12.076

  日期：2010.5

  Based on the naturally occurring stilbene, Resveratrol, a series of novel stilbene derivatives were synthesized, which have the ability to induce the expression of the ApoA-I gene. Several compounds equally or more potent than Resveratrol were identified. trans-4,4'-Dihydroxy-2-methoxystilbene was the most potent (4.6x more potent than Resveratrol). These compounds provide an early lead into new drugs to treat atherosclerosis. (C) 2010 Elsevier Masson SAS. All rights reserved.
• US7846915B2
  申请人：——

  公开号：US7846915B2

  公开（公告）日：2010-12-07