(Z)-4-Bromo-3-(6-methoxy-benzofuran-2-yl)-but-2-enoic acid ethyl ester | 136138-92-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-4-Bromo-3-(6-methoxy-benzofuran-2-yl)-but-2-enoic acid ethyl ester
• CAS: 136138-92-6
• 化学式: C₁₅H₁₅BrO₄
• 分子量: 339.186
• InChiKey: JONPQYUEHDLXJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-Bromo-3-(6-methoxy-benzofuran-2-yl)-but-2-enoic acid ethyl ester 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以58%的产率得到4-(6-Methoxy-benzofuran-2-yl)-1,5-dihydro-pyrrol-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
• 作为产物：
  描述：

  1-(6-甲氧基-2-苯并呋喃基)乙酮 在 N-溴代丁二酰亚胺(NBS) 、 phosphorus pentoxide 、 锌 作用下， 以 四氯化碳 、 甲苯 、 苯 为溶剂， 反应 51.0h， 生成 (Z)-4-Bromo-3-(6-methoxy-benzofuran-2-yl)-but-2-enoic acid ethyl ester
  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