4'-(1-methyl-1-(ethoxycarbonyl)ethoxy)-7-hydroxyisoflavone | 1204747-77-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4'-(1-methyl-1-(ethoxycarbonyl)ethoxy)-7-hydroxyisoflavone
• 英文别名: Ethyl 2-[4-(7-hydroxy-4-oxochromen-3-yl)phenoxy]-2-methylpropanoate
• CAS: 1204747-77-2
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: AREYUZJPXNVQNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4'-(1-methyl-1-(ethoxycarbonyl)ethoxy)-7-hydroxyisoflavone 在 水 、 potassium carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 4'-(1-methyl-1-carboxylethoxy)-7-hydroxyisoflavone
  参考文献：
  名称：

  Novel phenoxyalkylcarboxylic acid derivatives as hypolipidaemic agents

  摘要：

  Novel phenoxyalkylcarboxylic acid derivatives based on the natural scaffolds, flavonoids, or resveratrol were designed, synthesized, and evaluated for hypolipidaemic activity. Among the compounds, 30b lowered the triglycerides by 48.5% (P < 0.05) and total cholesterol by 44.2% (P < 0.05), respectively, and was more effective than the reference drug fenofibric acid in a Triton WR-1339-induced hyperlipidaemic mice model orally (300 mg/kg body weight). 30b also showed 59.4% triglycerides lowering in an alloxan-induced diabetic mice model orally (150 mg/kg body weight). Receptor docking studies revealed that compound 30b could interact with the amino acid residues in the ligandbinding domain essential for the activation of the PPAR alpha. The results indicate that resveratrol should be a better scaffold to derive a new class of hypolipidaemic agents in comparison with a flavonoid scaffold.

  DOI：

  10.3109/14756366.2011.589840
• 作为产物：
  描述：

  大豆甙元 在 盐酸 、 水 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.5h， 生成 4'-(1-methyl-1-(ethoxycarbonyl)ethoxy)-7-hydroxyisoflavone
  参考文献：
  名称：

  Novel phenoxyalkylcarboxylic acid derivatives as hypolipidaemic agents

  摘要：

  Novel phenoxyalkylcarboxylic acid derivatives based on the natural scaffolds, flavonoids, or resveratrol were designed, synthesized, and evaluated for hypolipidaemic activity. Among the compounds, 30b lowered the triglycerides by 48.5% (P < 0.05) and total cholesterol by 44.2% (P < 0.05), respectively, and was more effective than the reference drug fenofibric acid in a Triton WR-1339-induced hyperlipidaemic mice model orally (300 mg/kg body weight). 30b also showed 59.4% triglycerides lowering in an alloxan-induced diabetic mice model orally (150 mg/kg body weight). Receptor docking studies revealed that compound 30b could interact with the amino acid residues in the ligandbinding domain essential for the activation of the PPAR alpha. The results indicate that resveratrol should be a better scaffold to derive a new class of hypolipidaemic agents in comparison with a flavonoid scaffold.

  DOI：

  10.3109/14756366.2011.589840

文献信息

• Novel phenoxyalkylcarboxylic acid derivatives as hypolipidaemic agents
  作者：Wei Li、Hao-yan Jia、Xin-hua He、Wei-guo Shi、Bo-hua Zhong

  DOI：10.3109/14756366.2011.589840

  日期：2012.4.1

  Novel phenoxyalkylcarboxylic acid derivatives based on the natural scaffolds, flavonoids, or resveratrol were designed, synthesized, and evaluated for hypolipidaemic activity. Among the compounds, 30b lowered the triglycerides by 48.5% (P < 0.05) and total cholesterol by 44.2% (P < 0.05), respectively, and was more effective than the reference drug fenofibric acid in a Triton WR-1339-induced hyperlipidaemic mice model orally (300 mg/kg body weight). 30b also showed 59.4% triglycerides lowering in an alloxan-induced diabetic mice model orally (150 mg/kg body weight). Receptor docking studies revealed that compound 30b could interact with the amino acid residues in the ligandbinding domain essential for the activation of the PPAR alpha. The results indicate that resveratrol should be a better scaffold to derive a new class of hypolipidaemic agents in comparison with a flavonoid scaffold.