2-(2-氨基-乙基)-[1,2,4]噁二唑-3,5-二酮 | 68373-11-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(2-氨基-乙基)-[1,2,4]噁二唑-3,5-二酮
• 英文名称: Quisqualamine
• 英文别名: 2-(2-azaniumylethyl)-3-oxo-1,2,4-oxadiazol-5-olate
• CAS: 68373-11-5
• 化学式: C₄H₇N₃O₃
• mdl: MFCD00673868
• 分子量: 145.118
• InChiKey: LIPCXBVXQUFCSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione hydrobromide 在 氢氧化钾 作用下， 反应 0.5h， 以78%的产率得到2-(2-氨基-乙基)-[1,2,4]噁二唑-3,5-二酮
  参考文献：
  名称：

  A Selective and Efficient Synthesis of Quisqualamine, a Novel GABA-Related Depressant Amino Acid

  摘要：

  DOI：

  10.1055/s-1982-29944

文献信息

• Quisqualamine, a novel γ-aminobutyric acid (GABA)-related depressant amino acid
  作者：R H Evans、A A Francis、K Hunt、M R Martin、J C Watkins

  DOI：10.1111/j.2042-7158.1978.tb13257.x

  日期：2011.4.12

  A new substance, quisqualamine, the decarboxylated analogue of quisqualic acid, predictably depressed electrical activity of neurons of the frog and rat spinal cord in vitro and of the mouse spinal cord in vivo. In the in vitro preparations, the action of quisqualamine was associated with a prolonged depolarization of primary afferent terminals which was sensitive to blockade by picrotoxin and bicuculline and which was also depressed by strychnine. This suggests an interaction of quisqualamine with presynaptic receptors for both GABA and β-alanine. Post-synaptic actions of quisqualamine, which were less marked than those at pre-synaptic sites, also appeared to be predominantly GABA-mimetic in vitro, though a sensitivity to the GABA-antagonist bicuculline could not be demonstrated in vivo.

  一种新物质，Quisqualamine，是Quisqualic酸的脱羧类似物，在体外抑制了青蛙和大鼠脊髓神经元的电活动，在体内也抑制了小鼠脊髓的电活动。在体外制备中，Quisqualamine的作用与初级传入末梢的长时程去极化有关，该去极化对Picrotoxin和Bicuculline的阻断敏感，也被Strychnine抑制。这表明Quisqualamine与GABA和β-丙氨酸的突触前受体相互作用。Quisqualamine的神经元后突触作用在体外比突触前作用更少，虽然在体内不能证明其对GABA拮抗剂Bicuculline的敏感性，但主要表现为GABA类似物。

• A Selective and Efficient Synthesis of Quisqualamine, a Novel GABA-Related Depressant Amino Acid
  作者：Philippe Dugenet、Jean Jacques Yaouanc、Georges Sturtz

  DOI：10.1055/s-1982-29944

  日期：——