7-methoxy-2-(4-nitrobenzyl)-4H-1-benzopyran-4-one-3-carboxylic acid | 396665-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-methoxy-2-(4-nitrobenzyl)-4H-1-benzopyran-4-one-3-carboxylic acid
• 英文别名: 7-Methoxy-2-[(4-nitrophenyl)methyl]-4-oxochromene-3-carboxylic acid
• CAS: 396665-78-4
• 化学式: C₁₈H₁₃NO₇
• 分子量: 355.304
• InChiKey: DZRHYRWHFVIOGH-UHFFFAOYSA-N

物化性质

• 沸点：
  583.3±50.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-(4-nitrobenzyl)-4H-1-benzopyran-4-one-3-carboxylic acid 以 喹啉 为溶剂， 反应 0.17h， 以71%的产率得到7-methoxy-2-(4-nitrobenzyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  7-Hydroxy-2-substituted-4-H-1-benzopyran-4-one derivatives as aldose reductase inhibitors: a SAR study

  摘要：

  On the basis of the results of molecular modelling studies performed on the aldose reductase (ALR2) inhibitor 7-hydroxy-2-(4'-hydroxybenzyl)-4H-1-benzopyran-4-one (compound A) bound at the active site of the enzyme, we synthesised and tested on bovine and human ALR2 several derivatives modified at position 2 of the benzopyran moiety, in order to confirm the hypothesised binding mode of this compound. The substitution of the methylene bridge with the isosteric sulphur substituent gives an active derivative, while substitution with a polar NH causes a decrease in inhibitory activity; this is in accordance to the previously reported structure in which the methylene linker was found to be adjacent to a hydrophobic aminoacid (Leu300). Among the substituents at 4' position examined, the most favourable for inhibitory activity are those able to act as hydrogen bond donors, supporting the hypothesis of the importance of the interaction with Thr113 for the inhibition of the enzyme. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01272-7
• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 氢溴酸 、 magnesium ethylate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 7-methoxy-2-(4-nitrobenzyl)-4H-1-benzopyran-4-one-3-carboxylic acid
  参考文献：
  名称：

  7-Hydroxy-2-substituted-4-H-1-benzopyran-4-one derivatives as aldose reductase inhibitors: a SAR study

  摘要：

  On the basis of the results of molecular modelling studies performed on the aldose reductase (ALR2) inhibitor 7-hydroxy-2-(4'-hydroxybenzyl)-4H-1-benzopyran-4-one (compound A) bound at the active site of the enzyme, we synthesised and tested on bovine and human ALR2 several derivatives modified at position 2 of the benzopyran moiety, in order to confirm the hypothesised binding mode of this compound. The substitution of the methylene bridge with the isosteric sulphur substituent gives an active derivative, while substitution with a polar NH causes a decrease in inhibitory activity; this is in accordance to the previously reported structure in which the methylene linker was found to be adjacent to a hydrophobic aminoacid (Leu300). Among the substituents at 4' position examined, the most favourable for inhibitory activity are those able to act as hydrogen bond donors, supporting the hypothesis of the importance of the interaction with Thr113 for the inhibition of the enzyme. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01272-7