4-(6-Methoxy-2,3-dihydro-benzofuran-2-yl)-pyrrolidin-2-one | 136138-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(6-Methoxy-2,3-dihydro-benzofuran-2-yl)-pyrrolidin-2-one
• 英文别名: 4-(6-methoxy-2,3-dihydro-1-benzofuran-2-yl)pyrrolidin-2-one
• CAS: 136138-98-2
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: BHENRXHNQGHCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(6-Methoxy-2,3-dihydro-benzofuran-2-yl)-pyrrolidin-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以72%的产率得到4-Amino-3-(6-methoxy-2,3-dihydro-benzofuran-2-yl)-butyric acid
  参考文献：
  名称：

  Synthesis, pharmacology and X-ray studies of baclofen analogues

  摘要：

  Baclofen (beta-p-chlorophenyl-GABA) is the reference selective agonist for the bicuculline-insensitive GABA(B) receptor. The search for new compounds having a high affinity for the GABA(B) receptor is very important to clarify structural requirements. In that sense, we report the synthesis, binding studies and X-ray determinations of various 3-heteroaromatic gamma-aminobutyric acids. Biochemical investigations concerning their abilities to displace [H-3] muscimol (GABAA) and [H-3] baclofen (GABA(B)) in binding studies showed that the 4-amino-3-(5-methoxybenzo[b]furan-2-yl)butanoic acid 6a (IC50 = 22.16-mu-M/R (-) [H-3] baclofen; IC50 = 5.6-mu-M/RS [H-3] baclofen) has a specific affinity for the GABA(B) receptor. The crystal structure of compounds 6a and 6b associated with computer graphics molecular superimpositions allows some structural requirements for GABA(B) receptor ligands to be proposed.

  DOI：

  10.1016/0223-5234(91)90100-2
• 作为产物：
  描述：

  (E)-3-(6-Methoxy-benzofuran-2-yl)-but-2-enoic acid ethyl ester 在 镍 N-溴代丁二酰亚胺(NBS) 、 氨 、 氢气 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 为溶剂， 45.0 ℃ 、3.04 MPa 条件下， 反应 55.0h， 生成 4-(6-Methoxy-2,3-dihydro-benzofuran-2-yl)-pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis, pharmacology and X-ray studies of baclofen analogues

  摘要：

  Baclofen (beta-p-chlorophenyl-GABA) is the reference selective agonist for the bicuculline-insensitive GABA(B) receptor. The search for new compounds having a high affinity for the GABA(B) receptor is very important to clarify structural requirements. In that sense, we report the synthesis, binding studies and X-ray determinations of various 3-heteroaromatic gamma-aminobutyric acids. Biochemical investigations concerning their abilities to displace [H-3] muscimol (GABAA) and [H-3] baclofen (GABA(B)) in binding studies showed that the 4-amino-3-(5-methoxybenzo[b]furan-2-yl)butanoic acid 6a (IC50 = 22.16-mu-M/R (-) [H-3] baclofen; IC50 = 5.6-mu-M/RS [H-3] baclofen) has a specific affinity for the GABA(B) receptor. The crystal structure of compounds 6a and 6b associated with computer graphics molecular superimpositions allows some structural requirements for GABA(B) receptor ligands to be proposed.

  DOI：

  10.1016/0223-5234(91)90100-2