1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one | 944828-65-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one
• CAS: 944828-65-3
• 化学式: C₂₂H₂₄O₉
• 分子量: 432.427
• InChiKey: AQOVDNFCJFNLTR-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以84%的产率得到1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-3-(1,3-benzodioxol-5-yl)-2,3-oxiranylpropan-1-one
  参考文献：
  名称：

  Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage

  摘要：

  An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl ( DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O-2(center dot-) and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (+/-)-3e demonstrated remarkable inhibition to LPO with an IC50 value of 1.9 +/- 0.3 mu M, which was apparently stronger than that of quercetin (IC50 = 6.0 +/- 0.4 mu M). trans-Configurated dihydroflavonol (+/-)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC50 value of 41.5 +/- 5.3 mu M, more effective compared to that of quercetin (EC50 = 81.8 +/- 8.7 mu M). The 6-OH-5,7-dimethoxy analogue (+/-)-3d showed significant inhibition of xanthine oxidase with an IC50 value of 16.0 +/- 0.8 mu M, which is superior to that of allopurinol (IC50 = 23.5 +/- 2.0 mu M). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.032
• 作为产物：
  描述：

  胡椒醛 、 1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-ethanone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以74%的产率得到1-(2,4-dimethoxy-3,6-dimethoxymethoxyphenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one
  参考文献：
  名称：

  Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage

  摘要：

  An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl ( DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O-2(center dot-) and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (+/-)-3e demonstrated remarkable inhibition to LPO with an IC50 value of 1.9 +/- 0.3 mu M, which was apparently stronger than that of quercetin (IC50 = 6.0 +/- 0.4 mu M). trans-Configurated dihydroflavonol (+/-)-4h exhibited significant protective effect on PC12 cells against oxidative damage with an EC50 value of 41.5 +/- 5.3 mu M, more effective compared to that of quercetin (EC50 = 81.8 +/- 8.7 mu M). The 6-OH-5,7-dimethoxy analogue (+/-)-3d showed significant inhibition of xanthine oxidase with an IC50 value of 16.0 +/- 0.8 mu M, which is superior to that of allopurinol (IC50 = 23.5 +/- 2.0 mu M). In addition to the hypothesized action mechanism of the bio-active compounds, 3D modeling was used to analyze the relationship between the minimized-energy structures and antioxidant activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.032