4-(5-methylbenzo[b]thiophen-2-yl)pyrrolidin-2-one | 179729-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4-(5-methylbenzo[b]thiophen-2-yl)pyrrolidin-2-one
• 英文别名: 4-(5-Methyl-1-benzothiophen-2-yl)pyrrolidin-2-one
• CAS: 179729-33-0
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: BYAOGIGFPWXMAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(5-methylbenzo[b]thiophen-2-yl)pyrrolidin-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以54%的产率得到4-Amino-3-(5-methyl-benzo[b]thiophen-2-yl)-butyric acid
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8
• 作为产物：
  描述：

  5-甲基-1-苯并噻吩-2-甲醛 在 镍 氢气 、 苄基三甲基氢氧化铵 作用下， 以 乙醇 、 苯 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 4-(5-methylbenzo[b]thiophen-2-yl)pyrrolidin-2-one
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8