(E)-ethene-1,2-diylbis(4,1-phenylene) bis(3,4,5-trihydroxybenzoate)

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (E)-ethene-1,2-diylbis(4,1-phenylene) bis(3,4,5-trihydroxybenzoate)
• 英文别名: [4-[(E)-2-[4-(3,4,5-trihydroxybenzoyl)oxyphenyl]ethenyl]phenyl] 3,4,5-trihydroxybenzoate
• 化学式: C₂₈H₂₀O₁₀
• 分子量: 516.461
• InChiKey: ZPTVKNSOPWKEFO-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-碘乙酰基苯酚 在 4-二甲氨基吡啶 、 氟化铵 、 palladium diacetate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (E)-ethene-1,2-diylbis(4,1-phenylene) bis(3,4,5-trihydroxybenzoate)
  参考文献：
  名称：

  Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells

  摘要：

  Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111597

文献信息

• Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells
  作者：Yu-Jia Tan、Azhar Ali、Sheng-Yang Tee、Jun-Ting Teo、Yu Xi、Mei-Lin Go、Yulin Lam

  DOI：10.1016/j.ejmech.2019.111597

  日期：2019.11

  Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability. (C) 2019 Elsevier Masson SAS. All rights reserved.