4-[(4-fluorophenyl)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid | 147433-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[(4-fluorophenyl)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
• CAS: 147433-66-7
• 化学式: C₁₄H₁₄FNO₂
• 分子量: 247.269
• InChiKey: FJXDQFGQCIWVPE-UHFFFAOYSA-N

物化性质

• 沸点：
  426.6±45.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53.09
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-[(4-fluorophenyl)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid 在 盐酸 、 tetraphosphorus decasulfide 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.67h， 生成 [6-(4-Fluoro-benzyl)-5,7-dimethyl-3-oxo-1-thioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8
• 作为产物：
  描述：

  3,5-二甲基-1H-吡咯-2-甲酸乙酯 在 三乙基硅烷 、 sodium hydroxide 、 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 、 三氟乙酸 为溶剂， 反应 20.0h， 生成 4-[(4-fluorophenyl)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8

文献信息

• Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole
  作者：I Yamawaki、Y Matsushita、N Asaka、K Ohmori、N Nomura、K Ogawa

  DOI：10.1016/0223-5234(93)90016-8

  日期：1993.1

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.