1H-pyrrole-3-carboxylic acid, 2,5-dihydro-1-methyl-4-phenyl-, ethyl ester | 137569-75-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1H-pyrrole-3-carboxylic acid, 2,5-dihydro-1-methyl-4-phenyl-, ethyl ester
• 英文别名: ethyl 1-methyl-4-phenyl-2,5-dihydropyrrole-3-carboxylate
• CAS: 137569-75-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: LZTGRCFDNPLACX-UHFFFAOYSA-N

物化性质

• 沸点：
  337.4±42.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1H-pyrrole-3-carboxylic acid, 2,5-dihydro-1-methyl-4-phenyl-, ethyl ester 在 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 1H-pyrrole-3-carboxylic acid, 2,5-dihydro-4-phenyl-, ethyl ester, monohydrochloride
  参考文献：
  名称：

  .beta.-Proline analogs as agonists at the strychnine-sensitive glycine receptor

  摘要：

  3-Carboxy-3,4-dehydropyrrolidine was found to bind with affinity equal to that of glycine in a [H-3]strychnine binding assay. Simple substitution of the 1-, 2-, 4-, or 5-position resulted in marked loss of affinity. A decline in affinity was also found upon enlargement, contraction, or saturation of the 5-membered ring. However, beta-proline and azetidine-3-carboxylic acid retained significant binding affinity. Despite its good affinity in [H-3]strychnine binding, 3-carboxy-3,4-dehydropyrrolidine showed only weak agonist activity in intracellular recordings of cultured murine spinal cord neurons. This apparent lack of correlation between binding and functional results is discussed in light of the current models of the strychnine-sensitive glycine receptor.

  DOI：

  10.1021/jm00080a006
• 作为产物：
  描述：

  聚合甲醛 、 肌氨酸 、 苯丙炔酸乙酯 在 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以20.2%的产率得到1H-pyrrole-3-carboxylic acid, 2,5-dihydro-1-methyl-4-phenyl-, ethyl ester
  参考文献：
  名称：

  .beta.-Proline analogs as agonists at the strychnine-sensitive glycine receptor

  摘要：

  3-Carboxy-3,4-dehydropyrrolidine was found to bind with affinity equal to that of glycine in a [H-3]strychnine binding assay. Simple substitution of the 1-, 2-, 4-, or 5-position resulted in marked loss of affinity. A decline in affinity was also found upon enlargement, contraction, or saturation of the 5-membered ring. However, beta-proline and azetidine-3-carboxylic acid retained significant binding affinity. Despite its good affinity in [H-3]strychnine binding, 3-carboxy-3,4-dehydropyrrolidine showed only weak agonist activity in intracellular recordings of cultured murine spinal cord neurons. This apparent lack of correlation between binding and functional results is discussed in light of the current models of the strychnine-sensitive glycine receptor.

  DOI：

  10.1021/jm00080a006

文献信息

• .beta.-Proline analogs as agonists at the strychnine-sensitive glycine receptor
  作者：Graham Johnson、James T. Drummond、Peter A. Boxer、Robert F. Bruns

  DOI：10.1021/jm00080a006

  日期：1992.1

  3-Carboxy-3,4-dehydropyrrolidine was found to bind with affinity equal to that of glycine in a [H-3]strychnine binding assay. Simple substitution of the 1-, 2-, 4-, or 5-position resulted in marked loss of affinity. A decline in affinity was also found upon enlargement, contraction, or saturation of the 5-membered ring. However, beta-proline and azetidine-3-carboxylic acid retained significant binding affinity. Despite its good affinity in [H-3]strychnine binding, 3-carboxy-3,4-dehydropyrrolidine showed only weak agonist activity in intracellular recordings of cultured murine spinal cord neurons. This apparent lack of correlation between binding and functional results is discussed in light of the current models of the strychnine-sensitive glycine receptor.