{[2-(4-Fluoro-phenyl)-8-trifluoromethyl-quinoline-4-carbothioyl]-methyl-amino}-acetic acid ethyl ester | 148887-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: {[2-(4-Fluoro-phenyl)-8-trifluoromethyl-quinoline-4-carbothioyl]-methyl-amino}-acetic acid ethyl ester
• 英文别名: Ethyl 2-[[2-(4-fluorophenyl)-8-(trifluoromethyl)quinoline-4-carbothioyl]-methylamino]acetate
• CAS: 148887-81-4
• 化学式: C₂₂H₁₈F₄N₂O₂S
• 分子量: 450.457
• InChiKey: MEBLKDIXRAWLAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {[2-(4-Fluoro-phenyl)-8-trifluoromethyl-quinoline-4-carbothioyl]-methyl-amino}-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 以60%的产率得到{[2-(4-Fluoro-phenyl)-8-trifluoromethyl-quinoline-4-carbothioyl]-methyl-amino}-acetic acid
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of N-(quinolinyl thiocarbonyl) glycine derivatives

  摘要：

  The onset of diabetic complications may be prevented by the inhibition of aldose reductase. Derivatives of N-(quinolinyl thiocarbonyl) glycine were prepared and their in vitro and ex vivo aldose reductase inhibitory activities were tested on rat lens. The cincophen derivatives were the most potent in vitro with an enzyme inhibition value of 29% at 10(-8) M and 91% at 10(-7) M for the N-[(2-phenylquinolin-4-yl)thiocarbonyl]-N-methylglycine compound 10a This activity was shown to be dependent on the nature of the substituents and seems to be optimal for the acids; esters were found to be inactive. No compound have shown ex vivo inhibitory activity. It is concluded that the lack of ex vivo activity is likely due to a poor bioavailability or a bad penetration of the compounds in target tissue (lens).

  DOI：

  10.1016/0223-5234(92)90032-v
• 作为产物：
  描述：

  7-三氟甲基靛红 在 劳森试剂 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 21.0h， 生成 {[2-(4-Fluoro-phenyl)-8-trifluoromethyl-quinoline-4-carbothioyl]-methyl-amino}-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of N-(quinolinyl thiocarbonyl) glycine derivatives

  摘要：

  The onset of diabetic complications may be prevented by the inhibition of aldose reductase. Derivatives of N-(quinolinyl thiocarbonyl) glycine were prepared and their in vitro and ex vivo aldose reductase inhibitory activities were tested on rat lens. The cincophen derivatives were the most potent in vitro with an enzyme inhibition value of 29% at 10(-8) M and 91% at 10(-7) M for the N-[(2-phenylquinolin-4-yl)thiocarbonyl]-N-methylglycine compound 10a This activity was shown to be dependent on the nature of the substituents and seems to be optimal for the acids; esters were found to be inactive. No compound have shown ex vivo inhibitory activity. It is concluded that the lack of ex vivo activity is likely due to a poor bioavailability or a bad penetration of the compounds in target tissue (lens).

  DOI：

  10.1016/0223-5234(92)90032-v

文献信息

• Synthesis and aldose reductase inhibitory activity of N-(quinolinyl thiocarbonyl) glycine derivatives
  作者：E Nicolaï、T Güngör、J Goyard、G Cure、A Fouquet、JM Teulon、C Delchambre、A Cloarec

  DOI：10.1016/0223-5234(92)90032-v

  日期：1992.12

  The onset of diabetic complications may be prevented by the inhibition of aldose reductase. Derivatives of N-(quinolinyl thiocarbonyl) glycine were prepared and their in vitro and ex vivo aldose reductase inhibitory activities were tested on rat lens. The cincophen derivatives were the most potent in vitro with an enzyme inhibition value of 29% at 10(-8) M and 91% at 10(-7) M for the N-[(2-phenylquinolin-4-yl)thiocarbonyl]-N-methylglycine compound 10a This activity was shown to be dependent on the nature of the substituents and seems to be optimal for the acids; esters were found to be inactive. No compound have shown ex vivo inhibitory activity. It is concluded that the lack of ex vivo activity is likely due to a poor bioavailability or a bad penetration of the compounds in target tissue (lens).