(2E)-1-[2,4-bis(benzyloxy)phenyl]-3-(2-methoxyphenyl)prop-2-en-1-one

• 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: (2E)-1-[2,4-bis(benzyloxy)phenyl]-3-(2-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-[2,4-bis(phenylmethoxy)phenyl]-3-(2-methoxyphenyl)prop-2-en-1-one
• 化学式: C₃₀H₂₆O₄
• 分子量: 450.534
• InChiKey: UNYZJXADZYUKFY-KNTRCKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-1-[2,4-bis(benzyloxy)phenyl]-3-(2-methoxyphenyl)prop-2-en-1-one 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到2',4'-二羟基-2-甲氧基查耳酮
  参考文献：
  名称：

  Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

  摘要：

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).

  DOI：

  10.3109/14756366.2010.543420
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 生成 (2E)-1-[2,4-bis(benzyloxy)phenyl]-3-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

  摘要：

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).

  DOI：

  10.3109/14756366.2010.543420

文献信息

• Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
  作者：Lei Ma、Zhengyi Yang、Chenjing Li、Zhiyuan Zhu、Xu Shen、Lihong Hu

  DOI：10.3109/14756366.2010.543420

  日期：2011.10.1

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).