4-amino-3-(indol-3-yl)butanoic acid | 16960-34-2

• 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-amino-3-(indol-3-yl)butanoic acid
• 英文别名: 4-Amino-3-indolyl-(3)-buttersaeure；4-amino-3-indol-3-yl-butyric acid；4-amino-3-(1H-indol-3-yl)butanoic acid
• CAS: 16960-34-2
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: OAUILGHHTGBUGY-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 沸点：
  460.4±35.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-amino-3-(indol-3-yl)butanoic acid 在 氯化亚砜 作用下， 反应 18.0h， 生成 4-Amino-3-(1H-indol-3-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022
• 作为产物：
  描述：

  3-Cyan-3-(3-Indolyl)propionsaeure-ethylester 在 Raney Ni (W-4) sodium hydroxide 、 氢气 作用下， 反应 8.0h， 生成 4-amino-3-(indol-3-yl)butanoic acid
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022

文献信息

• Synthesis and Neuropsychotropic Activity of Indole-Containing Gamma-Aminobutyric Acid Derivatives
  作者：V. M. Berestovitskaya、O. S. Vasil’eva、E. S. Ostroglyadov、S. M. Aleksandrova、I. N. Tyurenkov、O. V. Merkushenkova、V. V. Bagmetova

  DOI：10.1007/s11094-018-1827-0

  日期：2018.8

  A series of indole-containing γ-aminobutyric acids (GABA) were synthesized via alkaline hydrolysis of 4-(indol-3-yl)-2-pyrrolidones. Their structures were confirmed by IR, PMR, and 13C NMR spectroscopy. Studies of the pharmacological properties of 4-amino-3-indolylbutanoic acids (GABA derivatives) showed that they possessed neuropsychotropic activity, the spectrum of which depended on the acid molecular structure. Nootropic properties prevailed for 4-amino-3-(indol-3-yl)butanoic acid; anxiolytic activity, for 4-amino-3-(1-benzylindol-3-yl)butanoic acid.

  一系列含吲哚的γ-氨基丁酸（GABA）通过对4-(吲哚-3-基)-2-吡咯烷酮的碱性水解合成。它们的结构通过红外光谱（IR）、质子核磁共振（PMR）和碳-13核磁共振（13C NMR）得到了确认。对4-氨基-3-吲哚基丁酸（GABA衍生物）药理特性的研究表明，它们具有神经精神药理活性，其谱系依赖于酸的分子结构。4-氨基-3-(吲哚-3-基)丁酸的认知促进特性较为突出；而4-氨基-3-(1-苯基吲哚-3-基)丁酸则表现出较强的抗焦虑活性。