1-(3,4-dichlorophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one | 1017263-27-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3,4-dichlorophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1017263-27-2
• 化学式: C₁₈H₁₆Cl₂O₄
• 分子量: 367.229
• InChiKey: NKQDENCNZZTUCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 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：
  0.17
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 、 3,4-二氯苯乙酮 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以76%的产率得到1-(3,4-dichlorophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  A Synthetic Chalcone as a Potent Inducer of Glutathione Biosynthesis

  摘要：

  Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2',5'-dihydroxychalcone (2',5'-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F andCl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4',6'-dimethoxy-2'-hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.

  DOI：

  10.1021/jm2016073

文献信息

• A Synthetic Chalcone as a Potent Inducer of Glutathione Biosynthesis
  作者：Remy Kachadourian、Brian J. Day、Subbiah Pugazhenti、Christopher C. Franklin、Estelle Genoux-Bastide、Gregory Mahaffey、Charlotte Gauthier、Attilio Di Pietro、Ahcène Boumendjel

  DOI：10.1021/jm2016073

  日期：2012.2.9

  Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2',5'-dihydroxychalcone (2',5'-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F andCl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4',6'-dimethoxy-2'-hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.