ethyl 1-(methylthio)acrylate | 131436-92-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 1-(methylthio)acrylate
• 英文别名: Ethyl 2-methylsulfanylbut-3-enoate
• CAS: 131436-92-5
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: XQVUBTXYPZRLTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(methylthio)acrylate 、 苄胺 以 乙醇 为溶剂， 反应 4.0h， 以79%的产率得到ethyl 3-(benzylamino)-2-(methylthio)propionate
  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