3-(2,4-二氧代咪唑烷-1-基)丙氨酸 | 95657-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-(2,4-二氧代咪唑烷-1-基)丙氨酸
• 英文名称: 2-Amino-3-(2,4-dioxo-imidazolidin-1-yl)-propionic acid
• 英文别名: 3-(2,4-Dioxoimidazolidin-1-yl)alanine；2-amino-3-(2,4-dioxoimidazolidin-1-yl)propanoic acid
• CAS: 95657-12-8
• 化学式: C₆H₉N₃O₄
• 分子量: 187.155
• InChiKey: UROMBTYUGMWQMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 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：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2(S)--3-propanoate 在 氢氧化钾 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-(2,4-二氧代咪唑烷-1-基)丙氨酸
  参考文献：
  名称：

  Quisqualic acid analogs: synthesis of .beta.-heterocyclic 2-aminopropanoic acid derivatives and their activity at a novel quisqualate-sensitized site

  摘要：

  Hippocampal CA1 pyramidal cell neurons are sensitized over 30-fold to depolarization by L-2-amino-4-phosphonobutanoic acid (L-AP4) following exposure to L-quisqualic acid. This phenomenon has been termed the QUIS effect. In the present study several novel L-quisqualic acid analogues have been synthesized and tested for their interaction with the different components of the QUIS-effect system. Replacement of the oxadiazolidinedione ring Of L-quisqualic acid with several other types of heterocyclic rings yielded the following quisqualic acid analogues: maleimide 2, N-methylmaleimide 3, N-(carboxymethyl)maleimide 4, succinimides 5A and 5B, and imidazolidinedione 6. None of these analogues were able to mimic the effects Of L-quisqualic acid and sensitize hippocampal CA1 neurons to depolarization by L-AP4. Also, unlike L-serine O-sulfate, L-homocysteinesulfinic acid, or L-alpha-aminoadipic acid, none of the analogues were able to preblock or reverse the QUIS effect. However, when the IC50 values for inhibition of the CA1 synaptic field potential of analogues 2-6 were determined both before and after hippocampal slices were exposed to L-quisqualic acid, the IC50 values of analogues 3 and 4 were found to decrease more than 7-fold. Thus, these two compounds behave like L-AP4 rather than L-quisqualic acid in this system in that they exhibit increased potencies in slices that have been pretreated with L-quisqualic acid even though they cannot themselves induce this sensitization. Compounds 3 and 4, therefore, represent the first non-phosphorus-containing compounds to which hippocampal neurons become sensitized following exposure to L-quisqualic acid. No change in the IC50 values was observed for 5A or 5B. Analogues 2 and 6, on the other hand, displayed a high potency for inhibition of the evoked field potential even prior to treatment of the slices with L-quisqualic acid.

  DOI：

  10.1021/jm00102a014

文献信息

• A convenient synthesis of the neuroexcitatory amino acid quisqalic acid and its analogues
  作者：Barrie W. Bycroft、Siri Ram Chhabra、Raymond J. Grout、Patrick J. Crowley

  DOI：10.1039/c39840001156

  日期：——

  Reaction of the enol 4 with hydroxylamines, hydrazines and glycine esters provides convenient intermediates for the synthesis of quisqualic acid 1 and its analogues 2 and 3.

  烯醇4与羟胺，肼和甘氨酸酯的反应为合成喹喹酸1及其类似物2和3提供了方便的中间体。
• Quisqualic acid analogs: synthesis of .beta.-heterocyclic 2-aminopropanoic acid derivatives and their activity at a novel quisqualate-sensitized site
  作者：Nalin Subasinghe、Marvin Schulte、Robert J. Roon、James F. Koerner、Rodney L. Johnson

  DOI：10.1021/jm00102a014

  日期：1992.11

  Hippocampal CA1 pyramidal cell neurons are sensitized over 30-fold to depolarization by L-2-amino-4-phosphonobutanoic acid (L-AP4) following exposure to L-quisqualic acid. This phenomenon has been termed the QUIS effect. In the present study several novel L-quisqualic acid analogues have been synthesized and tested for their interaction with the different components of the QUIS-effect system. Replacement of the oxadiazolidinedione ring Of L-quisqualic acid with several other types of heterocyclic rings yielded the following quisqualic acid analogues: maleimide 2, N-methylmaleimide 3, N-(carboxymethyl)maleimide 4, succinimides 5A and 5B, and imidazolidinedione 6. None of these analogues were able to mimic the effects Of L-quisqualic acid and sensitize hippocampal CA1 neurons to depolarization by L-AP4. Also, unlike L-serine O-sulfate, L-homocysteinesulfinic acid, or L-alpha-aminoadipic acid, none of the analogues were able to preblock or reverse the QUIS effect. However, when the IC50 values for inhibition of the CA1 synaptic field potential of analogues 2-6 were determined both before and after hippocampal slices were exposed to L-quisqualic acid, the IC50 values of analogues 3 and 4 were found to decrease more than 7-fold. Thus, these two compounds behave like L-AP4 rather than L-quisqualic acid in this system in that they exhibit increased potencies in slices that have been pretreated with L-quisqualic acid even though they cannot themselves induce this sensitization. Compounds 3 and 4, therefore, represent the first non-phosphorus-containing compounds to which hippocampal neurons become sensitized following exposure to L-quisqualic acid. No change in the IC50 values was observed for 5A or 5B. Analogues 2 and 6, on the other hand, displayed a high potency for inhibition of the evoked field potential even prior to treatment of the slices with L-quisqualic acid.