ethyl 3-(5-chloro-2-thienyl)-prop-2-enoate | 133933-42-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(5-chloro-2-thienyl)-prop-2-enoate
• 英文别名: Ethyl 3-(5-chlorothiophen-2-yl)prop-2-enoate
• CAS: 133933-42-3
• 化学式: C₉H₉ClO₂S
• 分子量: 216.688
• InChiKey: LYTPGYGIDXTNBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(5-chloro-2-thienyl)-prop-2-enoate 在 镍 sodium hydroxide 、 氢气 、 苄基三甲基氢氧化铵 作用下， 反应 19.0h， 生成 4-amino-3-(5-chlorothien-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
• 作为产物：
  描述：

  5-氯噻吩-2-甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 7.0h， 以78%的产率得到ethyl 3-(5-chloro-2-thienyl)-prop-2-enoate
  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