2′,4,4′,5′-tetrahydroxychalcone | 1014976-78-3

• 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: 2′,4,4′,5′-tetrahydroxychalcone
• 英文别名: Isoliquiritigenin metabolite M2；(E)-3-(4-hydroxyphenyl)-1-(2,4,5-trihydroxyphenyl)prop-2-en-1-one
• CAS: 1014976-78-3
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: BWFBUWODVNLGFS-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2,4,5-三羟基苯基)乙酮 、 对羟基苯甲醛 在 氯甲基甲基醚 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 乙腈 、 乙醇 为溶剂， 反应 3.0h， 以47%的产率得到2′,4,4′,5′-tetrahydroxychalcone
  参考文献：
  名称：

  The comparison of neuroprotective effects of isoliquiritigenin and its Phase I metabolites against glutamate-induced HT22 cell death

  摘要：

  It is becoming increasingly important to investigate drug metabolites to evaluate their toxic or preventive effects after administration of the parent compound. In our previous study, isoliquiritigenin isolated from Glycyrrhizae Radix effectively protected mouse-derived hippocampal neuronal cells (HT22) against 5 mM glutamate-induced oxidative stress. However, there is little information on the protective effects of the metabolites of isoliquiritigenin on HT22 cells. In this study, isoliquiritigenin and its Phase I metabolites were prepared and their neuroprotective activities on glutamate-treated HT22 cells were compared. The prepared metabolites were liquiritigenin (1), 20,4,40,50-tetrahydroxychalcone (2), sulfuretin (3), butein (4), davidigenin (5), and cis-6,40-dihydroxyaurone (6). Among the six metabolites, 4 showed better neuroprotective effects than the parent compound, isoliquiritigenin. Our study suggests that the neuroprotective effect of isoliquiritigenin could be elevated by its active metabolite 4, which is a chalcone containing a catechol group in the B ring. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.072

文献信息

• The comparison of neuroprotective effects of isoliquiritigenin and its Phase I metabolites against glutamate-induced HT22 cell death
  作者：Eun-Ju Yang、Minjun Kim、Ji Eun Woo、Taeho Lee、Jong-Wha Jung、Kyung-Sik Song

  DOI：10.1016/j.bmcl.2016.10.072

  日期：2016.12

  It is becoming increasingly important to investigate drug metabolites to evaluate their toxic or preventive effects after administration of the parent compound. In our previous study, isoliquiritigenin isolated from Glycyrrhizae Radix effectively protected mouse-derived hippocampal neuronal cells (HT22) against 5 mM glutamate-induced oxidative stress. However, there is little information on the protective effects of the metabolites of isoliquiritigenin on HT22 cells. In this study, isoliquiritigenin and its Phase I metabolites were prepared and their neuroprotective activities on glutamate-treated HT22 cells were compared. The prepared metabolites were liquiritigenin (1), 20,4,40,50-tetrahydroxychalcone (2), sulfuretin (3), butein (4), davidigenin (5), and cis-6,40-dihydroxyaurone (6). Among the six metabolites, 4 showed better neuroprotective effects than the parent compound, isoliquiritigenin. Our study suggests that the neuroprotective effect of isoliquiritigenin could be elevated by its active metabolite 4, which is a chalcone containing a catechol group in the B ring. (C) 2016 Elsevier Ltd. All rights reserved.