4-{[(7-amino-2-oxo-2H-1-benzopyran-4-yl)methyl]amino}butanoic acid | 873950-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-{[(7-amino-2-oxo-2H-1-benzopyran-4-yl)methyl]amino}butanoic acid
• 英文别名: 4-{[(7-Amino-2-oxo-2H-1-benzopyran-4-yl)methyl]amino}butanoic acid；4-[(7-amino-2-oxochromen-4-yl)methylamino]butanoic acid
• CAS: 873950-23-3
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: ABBDKCYIEDGOTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  562.6±50.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3-羟基-苯基)-氨基甲酸乙酯 在 硫酸 、 溶剂黄146 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 4-{[(7-amino-2-oxo-2H-1-benzopyran-4-yl)methyl]amino}butanoic acid
  参考文献：
  名称：

  Synthesis, Photophysical, Photochemical and Biological Properties of Caged GABA, 4-[[(2H-1-Benzopyran-2-one-7-amino-4-methoxy) carbonyl] amino] Butanoic Acid¶

  摘要：

  The photorelease of a caged neurotransmitter can be used to investigate the function of neuronal circuits in tissues. We have designed and synthesized a stable, caged gamma-aminobutyric acid (GABA) derivative, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy)carbonyl]amino] butanoic acid (BC204), that releases the neurotransmitter in physiological medium when irradiated with UV light at 300-400 mn in PBS at pH 7.4. The release of GABA occurs with the formation of the major photoproduct, 7-amino-4-(hydroxymethyl)-2H-1-benzopyran-2-one, via a solvolytic photodegradation mechanism of the coumarin moiety and was confirmed by electrospray mass spectrometry/mass spectrometry (ESI MS/MS). BC204 is chemically stable and shows no intrinsic activity after many hours under physiological dark conditions. These properties suggest that BC204 is an excellent form of caged GABA that is well suited for long-term biological studies.

  DOI：

  10.1562/2004-07-08-ra-226.1

文献信息

• Synthesis, Photophysical, Photochemical and Biological Properties of Caged GABA, 4-[[(2H-1-Benzopyran-2-one-7-amino-4-methoxy) carbonyl] amino] Butanoic Acid¶
  作者：Beate Cürten、Paul H. M. Kullmann、Mark E. Bier、Karl Kandler、Brigitte F. Schmidt

  DOI：10.1562/2004-07-08-ra-226.1

  日期：——

  The photorelease of a caged neurotransmitter can be used to investigate the function of neuronal circuits in tissues. We have designed and synthesized a stable, caged gamma-aminobutyric acid (GABA) derivative, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy)carbonyl]amino] butanoic acid (BC204), that releases the neurotransmitter in physiological medium when irradiated with UV light at 300-400 mn in PBS at pH 7.4. The release of GABA occurs with the formation of the major photoproduct, 7-amino-4-(hydroxymethyl)-2H-1-benzopyran-2-one, via a solvolytic photodegradation mechanism of the coumarin moiety and was confirmed by electrospray mass spectrometry/mass spectrometry (ESI MS/MS). BC204 is chemically stable and shows no intrinsic activity after many hours under physiological dark conditions. These properties suggest that BC204 is an excellent form of caged GABA that is well suited for long-term biological studies.