3,5-dimethyl-4-propyl-1H-pyrrole-2-carboxylic acid | 147433-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,5-dimethyl-4-propyl-1H-pyrrole-2-carboxylic acid
• CAS: 147433-72-5
• 化学式: C₁₀H₁₅NO₂
• mdl: MFCD20547709
• 分子量: 181.235
• InChiKey: LVUKAQMHVVKNIH-UHFFFAOYSA-N

物化性质

• 沸点：
  340.7±30.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-4-propyl-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 2-(5,7-Dimethyl-3-oxo-6-propyl-1-sulfanylidenepyrrolo[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：

  ethyl 3,5-dimethyl-4-propylpyrrole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3,5-dimethyl-4-propyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  仅含一个丙酸基团的胆红素类似物的对映体选择

  摘要：

  仅具有单个β-甲基丙酸基团的对映体合成胆红素类似物（1和2）采用通过分子内氢键稳定的折叠的，脊-峰构象。β-甲基基团迫使颜料采取左旋（M）螺旋构象，如激子圆二色性光谱所表明的那样，表明一个丙酸基团足以控制颜料的构象。

  DOI：

  10.1016/s0957-4166(97)00481-3

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.
• Enantioselection in bilirubin analogs with only one propionic acid group
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1016/s0957-4166(97)00481-3

  日期：1997.11

  Enantiopure synthetic bilirubin analogs (1 and 2) with only a single β-methyl propionic acid group adopt a folded, ridge-tile conformation stabilized by intramolecular hydrogen bonding. The β-methyl group forces the pigment to adopt a left-handed (M) helical conformation, as evidenced by exciton circular dichroism spectra and indicating that one propionic acid group is sufficient to control the pigment's

  仅具有单个β-甲基丙酸基团的对映体合成胆红素类似物（1和2）采用通过分子内氢键稳定的折叠的，脊-峰构象。β-甲基基团迫使颜料采取左旋（M）螺旋构象，如激子圆二色性光谱所表明的那样，表明一个丙酸基团足以控制颜料的构象。