4-(5-甲氧基-1-苯并呋喃-2-基)吡咯烷-2-酮 | 88221-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 4-(5-甲氧基-1-苯并呋喃-2-基)吡咯烷-2-酮
• 英文名称: 4-(5-methoxybenzo[b]furan-2-yl)pyrrolidin-2-one
• 英文别名: 4-(5-Methoxy-1-benzofuran-2-yl)pyrrolidin-2-one
• CAS: 88221-15-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: AMGIPIPWHIWHGB-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  458.6±45.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-甲氧基-1-苯并呋喃-2-基)吡咯烷-2-酮 以72%的产率得到
  参考文献：
  名称：

  MAILLARD, J.;LANGLOIS, M.;TRI, VO, VAN;GUILLONNEAU, C.;LEGEA, J.;BENHARKA+, EUR. J. MED. CHEM., 1983, 18, N 4, 353-358

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基苯并呋喃-2-甲醛 在 镍 氢气 、 苄基三甲基氢氧化铵 作用下， 以 乙醇 为溶剂， 生成 4-(5-甲氧基-1-苯并呋喃-2-基)吡咯烷-2-酮
  参考文献：
  名称：

  Maillard; Langlois; Vo Van, European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 353 - 358

  摘要：

  DOI：

文献信息

• Synthesis of novel pyrrolidin-2-ones: γ-aminobutyric acid cyclic analogues
  作者：S. Al Akoum Ebrik、B. Rigo、C. Vaccher、M-P. Vaccher、N. Flouquet、M. Debaert、P. Berthelot

  DOI：10.1002/jhet.5570350314

  日期：1998.5

  Some new N-substituted pyrrolidin-2-ones, cyclic analogues of baclofen and of 3-(5-methoxybenzo-[b]furan-2-yl)-γ-aminobutyric acid, have been prepared and characterized, starting from 4-(4-chlorophenyl)-pyrrolidin-2-one and 4-(5-methoxybenzo[b]furan-2-yl)pyrrolidin-2-one.

  从4-（开始），已经制备并表征了一些新的N-取代的吡咯烷-2-酮，它们是巴氯芬和3-（5-甲氧基苯并-[ b ]呋喃-2-基）-γ-氨基丁酸的环状类似物。4-氯苯基）-吡咯烷-2-酮和4-（5-甲氧基苯并[ b ]呋喃-2-基）吡咯烷-2-酮。
• Synthesis and pharmacological evaluation of .gamma.-aminobutyric acid analogs. New ligand for GABAB sites
  作者：Pascal Berthelot、Claude Vaccher、Amir Musadad、Nathalie Flouquet、Michel Debaert、Michel Luyckx

  DOI：10.1021/jm00387a031

  日期：1987.4

  (beta-p-chlorophenyl-GABA) is the only selective agonist for the bicuculline-insensitive GABAB receptor. We report the synthesis of new GABA analogues and baclofen analogues. In vitro, two compounds, 4-amino-3-benzo[b]furan-2-ylbutanoic acid (9g) and 4-amino-3-(5-methoxybenzo[b]furan-2-yl)butanoic acid (9h), showed an affinity for the GABAB receptor. The results obtained with racemic compounds of benzofuran structure

  巴氯芬（β-对氯苯基-GABA）是双小分子不敏感的GABA B受体的唯一选择性激动剂。我们报告了新的GABA类似物和巴氯芬类似物的合成。在体外，两种化合物4-氨基-3-苯并[b]呋喃-2-基丁酸（9g）和4-氨基-3-（5-甲氧基苯并[b]呋喃-2-基）丁酸（9h）对GABAB受体具有亲和力。用苯并呋喃结构的外消旋化合物获得的结果，对于该系列是新的，以及化合物3a（4-氨基-3-（4-羟基苯基）丁酸）的令人惊讶的无活性，使得可以提出关于与关于GABAB受体。
• 3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies
  作者：M Ansar、S Al Akoum Ebriki、R Mouhoub、P Berthelot、C Vaccher、MP Vaccher、N Flouquet、DH Caignard、P Renard、B Pirard、MC Rettori、G Evrard、F Durant、M Debaert

  DOI：10.1016/0223-5234(96)85165-8

  日期：1996.1

  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.
• BERTHELOT P.; VACCHER C.; MUSADAD A.; FLOUQUET N.; DEBAERT M.; LUYCKX M., J. MED. CHEM., 30,(1987) N 4, 743-746
  作者：BERTHELOT P.、 VACCHER C.、 MUSADAD A.、 FLOUQUET N.、 DEBAERT M.、 LUYCKX M.

  DOI：——

  日期：——
• Synthesis, pharmacology and X-ray studies of baclofen analogues
  作者：P Berthelot、C Vaccher、N Flouquet、M Luyckx、C Brunet、T Boulanger、JP Frippiat、DP Vercauteren、M Debaert、G Evrard、F Durant

  DOI：10.1016/0223-5234(91)90100-2

  日期：1991.6

  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.