5-(2-carboxymethoxybenzylidene)-3-methyl-4-oxo-2-thioxothiazolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-carboxymethoxybenzylidene)-3-methyl-4-oxo-2-thioxothiazolidine
• 英文别名: 2-[2-[(Z)-(3-methyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetic acid
• 化学式: C₁₃H₁₁NO₄S₂
• 分子量: 309.367
• InChiKey: KOOLFMQLFUZBPA-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 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：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基罗丹宁 、 2-甲酰苯氧乙酸 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 以77%的产率得到5-(2-carboxymethoxybenzylidene)-3-methyl-4-oxo-2-thioxothiazolidine
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of a new series of 5-[[2-(ω-carboxyalkoxy)aryl]methylene]-4-oxo-2-thioxothiazolidine derivatives

  摘要：

  A new series of 5-[[2-(omega-carboxyalkoxy)aryl]methylene]-4-oxo-2-thioxothiazolidine derivatives was synthesized and evaluated for their potency as aldose reductase inhibitors (ARIs). Their activities were examined in terms of their inhibitory effect on rat lens aldose reductase in vitro and in terms of the preventive effect on sorbitol accumulation in the sciatic nerve of streptozotocin (STZ)-induced diabetic rats in vivo. Of these compounds, some of the naphthylmethylene thiazolidine derivatives were comparable to Zenarestat in the inhibitory potency in vitro and in vivo. In particular, compound 30 was 1.5 times more potent than Zenarestat in the in vivo activity, and had an adequate potency for clinical development. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00128-2

文献信息

• Synthesis and aldose reductase inhibitory activity of a new series of 5-[[2-(ω-carboxyalkoxy)aryl]methylene]-4-oxo-2-thioxothiazolidine derivatives
  作者：Makoto Murata、Buichi Fujitani、Hiroyuki Mizuta

  DOI：10.1016/s0223-5234(99)00128-2

  日期：1999.12

  A new series of 5-[[2-(omega-carboxyalkoxy)aryl]methylene]-4-oxo-2-thioxothiazolidine derivatives was synthesized and evaluated for their potency as aldose reductase inhibitors (ARIs). Their activities were examined in terms of their inhibitory effect on rat lens aldose reductase in vitro and in terms of the preventive effect on sorbitol accumulation in the sciatic nerve of streptozotocin (STZ)-induced diabetic rats in vivo. Of these compounds, some of the naphthylmethylene thiazolidine derivatives were comparable to Zenarestat in the inhibitory potency in vitro and in vivo. In particular, compound 30 was 1.5 times more potent than Zenarestat in the in vivo activity, and had an adequate potency for clinical development. (C) 1999 Editions scientifiques et medicales Elsevier SAS.