4-[4-(4-fluorobenzyl)piperazino]-7-methoxypyrrolo[1,2-a]quinoxaline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[4-(4-fluorobenzyl)piperazino]-7-methoxypyrrolo[1,2-a]quinoxaline
• 英文别名: 4-[4-[(4-Fluorophenyl)methyl]piperazin-1-yl]-7-methoxypyrrolo[1,2-a]quinoxaline
• 化学式: C₂₃H₂₃FN₄O
• 分子量: 390.46
• InChiKey: ACSDLURGGYXLSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-甲氧基-2-(1H-吡咯-1-基)苯胺 在 吡啶 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.0h， 生成 4-[4-(4-fluorobenzyl)piperazino]-7-methoxypyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Novel and Selective Partial Agonists of 5-HT₃ Receptors. 2. Synthesis and Biological Evaluation of Piperazinopyridopyrrolopyrazines, Piperazinopyrroloquinoxalines, and Piperazinopyridopyrroloquinoxalines

  摘要：

  In continuation of our previous work on piperazinopyrrolothienopyrazine derivatives, three series of piperazinopyridopyrrolopyrazines, piperazinopyrroloquinoxalines, and piperazinopyridopyrrolaquinoxalines were prepared and evaluated as 5-HT3 receptor ligands. The chemical modifications performed within these new series led to structure-activity relationships regarding both high affinity and selectivity for the 5-HT3 receptors that are in agreement with those established previously for the pyrrolothienopyrazine series. The best compound (8a) obtained in these new series is in the picomolar range of affinity for 5-HT3 receptors with a selectivity higher than 10(6). Four of the high-affinity 5-HT3 ligands (8a, 15a,b, and 16d) were selected in both the pyridopyrrolopyrazine and the pyrroloquinoxaline series and were characterized in vitro and in vivo as agonists or partial agonists. Compound 8a was also evaluated in the light/dark test where it showed potential anxiolytic-like activity at very low doses per os.

  DOI：

  10.1021/jm960501o

文献信息

• Dérivés de pyrrolopyrazines à activité 5-HT3
  申请人：ADIR ET COMPAGNIE

  公开号：EP0623620A1

  公开（公告）日：1994-11-09

  La présente invention concerne les composés de formule (I) : dans laquelle A et R₁ sont tels que définis dans la description. Médicaments.

  本发明涉及式（I）化合物： 其中 A 和 R₁ 如描述中所定义。 药物。
• US5599812A
  申请人：——

  公开号：US5599812A

  公开（公告）日：1997-02-04
• Novel and Selective Partial Agonists of 5-HT₃ Receptors. 2. Synthesis and Biological Evaluation of Piperazinopyridopyrrolopyrazines, Piperazinopyrroloquinoxalines, and Piperazinopyridopyrroloquinoxalines
  作者：Hervé Prunier、Sylvain Rault、Jean-Charles Lancelot、Max Robba、Pierre Renard、Philippe Delagrange、Bruno Pfeiffer、Daniel-Henri Caignard、René Misslin、Béatrice Guardiola-Lemaitre, and、Michel Hamon

  DOI：10.1021/jm960501o

  日期：1997.6.1

  In continuation of our previous work on piperazinopyrrolothienopyrazine derivatives, three series of piperazinopyridopyrrolopyrazines, piperazinopyrroloquinoxalines, and piperazinopyridopyrrolaquinoxalines were prepared and evaluated as 5-HT3 receptor ligands. The chemical modifications performed within these new series led to structure-activity relationships regarding both high affinity and selectivity for the 5-HT3 receptors that are in agreement with those established previously for the pyrrolothienopyrazine series. The best compound (8a) obtained in these new series is in the picomolar range of affinity for 5-HT3 receptors with a selectivity higher than 10(6). Four of the high-affinity 5-HT3 ligands (8a, 15a,b, and 16d) were selected in both the pyridopyrrolopyrazine and the pyrroloquinoxaline series and were characterized in vitro and in vivo as agonists or partial agonists. Compound 8a was also evaluated in the light/dark test where it showed potential anxiolytic-like activity at very low doses per os.