(E)-1-(2,4-dihydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one | 182686-51-7

• 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: (E)-1-(2,4-dihydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one
• 英文别名: (E)-1-(2,4-dihydroxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one；(E)-1-(2,4-dihydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one (7)
• CAS: 182686-51-7
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: PZNSXDODRVGONW-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 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：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到(E)-1-(2,4-dihydroxyphenyl)-3-(2-nitrophenyl)-2-propen-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

• Synthesis and evaluation of antiinflammatory activity of substituted chalcone derivatives
  作者：Xue-Wu Zhang、Dong-Hai Zhao、Ying-Chun Quan、Liang-Peng Sun、Xiu-Mei Yin、Li-Ping Guan

  DOI：10.1007/s00044-009-9202-z

  日期：2010.5

  In an effort to develop potent antiinflammatory agents, a series of substituted chalcone derivatives was synthesized and evaluated for antiinflammatory activity through monitoring of their ability to inhibit xylene-induced ear edema in mice. Some of the tested compounds exhibited significant activity, and compounds 3f [(E)-1-(2,4-dihydroxyphenyl)-3-(4-dimethylamino)phenyl)prop-2-en-1-one] and 3h [

  为了开发有效的抗炎药，合成了一系列取代的查尔酮衍生物，并通过监测其抑制小鼠二甲苯诱导的耳水肿的能力来评估其抗炎活性。一些测试的化合物显示出显着的活性，化合物3f [（E）-1-（2,4-二羟基苯基）-3-（4-二甲基氨基）苯基）prop-2-en-1-one]和3h [（E）-3-（4-氯苯基）-1-（2,4-二羟基苯基）丙-2-烯-1-酮]显示最高的抗炎活性（给药前2小时分别抑制62％和68％），与参考药物布洛芬（53％）相比甚至更有效。此外，这些取代的查耳酮衍生物的结构活性关系得到了证明。
• 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).