Acetic acid 4-[(Z)-2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl ester | 51115-00-5

• 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: Acetic acid 4-[(Z)-2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl ester
• CAS: 51115-00-5
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: WBYZMJDJRZEOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 4-[(Z)-2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl ester 在 二苯二硫醚 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以0.5 g的产率得到(E)-4'-acetoxy-3,3',5-trimethoxystilbene
  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：

  (3,5-二甲氧基苯基)乙酸 生成 Acetic acid 4-[(Z)-2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl ester
  参考文献：
  名称：

  薯蓣生长抑制剂batatasin I的结构与合成

  摘要：

  摘要 描述了 6-羟基-2,4,7-三甲氧基菲的合成，并证实了其与生长抑制剂 batatasin I 的同一性。

  DOI：

  10.1016/0031-9422(73)85100-3