4-amino-3-(4-bromothien-2-yl)butanoic acid | 133933-80-9

• 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-(4-bromothien-2-yl)butanoic acid
• 英文别名: 4-amino-3-(4-bromo-2-thienyl)butyric acid；4-Amino-3-(4-bromo-thiophen-2-yl)-butyric acid；4-amino-3-(4-bromothiophen-2-yl)butanoic acid
• CAS: 133933-80-9
• 化学式: C₈H₁₀BrNO₂S
• 分子量: 264.143
• InChiKey: VQHITWOESIJQLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 在 镍 sodium hydroxide 、 氢气 、 苄基三甲基氢氧化铵 作用下， 以 苯 为溶剂， 反应 26.0h， 生成 4-amino-3-(4-bromothien-2-yl)butanoic acid
  参考文献：
  名称：

  3-Thienyl- and 3-furylaminobutyric acids. Synthesis and binding GABAB receptor studies

  摘要：

  Baclofen (beta-(p-chlorophenyl)-GABA) is a selective agonist for the bicuculline-insensitive GABA(B) receptor. The search for new compounds that bind to the GABA(B) receptor is very important to clarify structural requirements. We report herein the synthesis and the binding studies of variously substituted 3-thienyl- and 3-furylaminobutyric acids. 4-Amino-3-(5-methyl-2-thienyl)butyric acid (5d) and 4-amino-3-(5-chloro-2-thienyl)butyric acid (5h) are potent and specific ligands for GABA(B) receptor. The IC50 values for the displacement of (R)-(-)-[H-3]baclofen are 1.34 and 0.61-mu-M for 5d and 5h, respectively, as compared to 0.33-mu-M for baclofen.

  DOI：

  10.1021/jm00112a033

文献信息

• 3-Thienyl- and 3-furylaminobutyric acids. Synthesis and binding GABAB receptor studies
  作者：Pascal Berthelot、Claude Vaccher、Nathalie Flouquet、Michel Debaert、Michel Luyckx、Claude Brunet

  DOI：10.1021/jm00112a033

  日期：1991.8

  Baclofen (beta-(p-chlorophenyl)-GABA) is a selective agonist for the bicuculline-insensitive GABA(B) receptor. The search for new compounds that bind to the GABA(B) receptor is very important to clarify structural requirements. We report herein the synthesis and the binding studies of variously substituted 3-thienyl- and 3-furylaminobutyric acids. 4-Amino-3-(5-methyl-2-thienyl)butyric acid (5d) and 4-amino-3-(5-chloro-2-thienyl)butyric acid (5h) are potent and specific ligands for GABA(B) receptor. The IC50 values for the displacement of (R)-(-)-[H-3]baclofen are 1.34 and 0.61-mu-M for 5d and 5h, respectively, as compared to 0.33-mu-M for baclofen.