[5-(4-Hydroxy-3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [5-(4-Hydroxy-3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
• 英文别名: 2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetic acid
• 化学式: C₁₃H₁₁NO₆S
• 分子量: 309.299
• InChiKey: JYPGFVKSBHLKEF-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2-(2,4-dioxothiazolidin-3-yl)acetate 在 哌啶 、 盐酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 [5-(4-Hydroxy-3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
  参考文献：
  名称：

  Evaluation of in vitro aldose redutase inhibitory activity of 5-arylidene-2,4-thiazolidinediones

  摘要：

  A number of 5-arylidene-2,4-thiazolidinediones containing a hydroxy or a carboxymethoxy group in their 5-benzylidene moiety have been synthesised and evaluated as in vitro aldose reductase (ALR2) inhibitors. Most of them exhibited strong inhibitory activity, with IC50 values in the range between 0.20 and 0.70 mu M. Molecular docking simulations into the ALR2 active site highlighted that the phenolic or carboxylic substituents of the 5-benzylidene moiety can favourably interact, in alternative poses, either with amino acid residues lining the lipophilic pocket of the enzyme, such as Leu300, or with the positively charged recognition region of the ALR2 active site. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.109