4-羟基-5-氧代-1-(2-噻吩基甲基)-2,5-二氢-1H-吡咯-3-羧酸乙酯 | 131436-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 4-羟基-5-氧代-1-(2-噻吩基甲基)-2,5-二氢-1H-吡咯-3-羧酸乙酯
• 英文名称: 4-Hydroxy-5-oxo-1-thiophen-2-ylmethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-hydroxy-5-oxo-1-(2-thienylmethyl)-2,5-dihydro-1H-pyrrole-3-carboxylate；ethyl 4-hydroxy-5-oxo-1-(thiophen-2-ylmethyl)-2H-pyrrole-3-carboxylate
• CAS: 131436-78-7
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: LCDLJTYTVMVKMU-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  2-噻吩甲胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-羟基-5-氧代-1-(2-噻吩基甲基)-2,5-二氢-1H-吡咯-3-羧酸乙酯
  参考文献：
  名称：

  A highly specific aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate and its congeners

  摘要：

  Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate (1, EBPC) is a potent and specific inhibitor of aldose reductase. It was > 4000 x more potent in its inhibition of rat lens aldose reductase than the closely related rat or pig kidney aldehyde reductase, thus making it the most selective inhibitor of a NADPH-dependent carbonyl reductase identified to date. In agreement with this observation, it was found to be a highly potent inhibitor of aldose reductase from rat sciatic nerve with > 98% inhibition at 1-mu-M, but it was practically devoid of activity against aldehyde reductases from rat liver and brain. Inhibition of aldose reductase was mixed type for glyceraldehyde (K(i) = 8.0 x 10(-8) M) and noncompetitive for NADPH (K(i) = 1.70 x 10(-8) M). Its potential as an in vitro tool to quantitate monomeric aldo/keto reductase activities in crude tissue extracts is presented. Structure-activity relationships emerging from synthetic modifications of EBPC are discussed. Several modifications were found to be active in vitro against aldose reductase from human placenta and in vivo in a rat model of diabetic complications, but none was more potent than EBPC.

  DOI：

  10.1021/jm00107a020

文献信息

• MYLARI, BANAVARA L.;BEYER, THOMAS A.;SIEGEL, TODD W., J. MED. CHEM., 34,(1991) N, C. 1011-1018
  作者：MYLARI, BANAVARA L.、BEYER, THOMAS A.、SIEGEL, TODD W.

  DOI：——

  日期：——