5-(aminomethyl)-1H-pyrrole-2-carboxylic acid;hydrochloride | 1401555-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(aminomethyl)-1H-pyrrole-2-carboxylic acid;hydrochloride
• CAS: 1401555-64-3
• 化学式: C₆H₈N₂O₂*ClH
• 分子量: 176.603
• InChiKey: CPVROAJAKXCAOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.1
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 5-((hydroxyimino)methyl)-1H-pyrrole-2-carboxylate 在 盐酸 、 lithium hydroxide monohydrate 、 10% Pd/C 、 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 5-(aminomethyl)-1H-pyrrole-2-carboxylic acid;hydrochloride
  参考文献：
  名称：

  Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase

  摘要：

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.009