5-piperazinopyrrolo[1,2-a]thieno[3,2-e]pyrazine | 153628-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-piperazinopyrrolo[1,2-a]thieno[3,2-e]pyrazine
• 英文别名: 8-Piperazin-1-yl-3-thia-1,7-diazatricyclo[7.3.0.02,6]dodeca-2(6),4,7,9,11-pentaene
• CAS: 153628-84-3
• 化学式: C₁₃H₁₄N₄S
• 分子量: 258.347
• InChiKey: XYOILXJZQNPSEP-UHFFFAOYSA-N

物化性质

• 沸点：
  436.2±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 、 5-piperazinopyrrolo[1,2-a]thieno[3,2-e]pyrazine 在 三乙胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到2-{4-[4-(1-thia-4,8a-diaza-as-indacen-5-yl)-piperazin-1-yl]butyl}-isoindole-1,3-dione
  参考文献：
  名称：

  氨基吡咯并[1,2-a]噻吩并[3,2-e]吡嗪衍生物作为5-羟色胺能5-HT7配体的合成

  摘要：

  制备并评估了一系列哌嗪并吡咯并 [1,2-a] 噻吩并 [3,2-e] 吡嗪衍生物，以确定它们对 5-HT7 受体的亲和力。探索了哌嗪上的各种取代以及用其他胺替代哌嗪。

  DOI：

  10.3998/ark.5550190.0011.a11
• 作为产物：
  描述：

  5-chloropyrrolo[1,2-a]thieno[3,2-e]pyrazine 在 sodium hydroxide 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-piperazinopyrrolo[1,2-a]thieno[3,2-e]pyrazine
  参考文献：
  名称：

  Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines

  摘要：

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.

  DOI：

  10.1021/jm950543x

文献信息

• Composés pyrrolothiénopyraziniques comme antagonistes des récepteurs 5-HT3
  申请人：ADIR ET COMPAGNIE

  公开号：EP0573360A1

  公开（公告）日：1993-12-08

  L'invention concerne les composés de formule générale (I) : dans laquelle R₁, R₂, R₃, et A sont tels que définis dans la description, leurs isomères optiques, et leurs sels d'addition à un acide ou une base pharmaceutiquement acceptable. Médicaments.

  本发明涉及通式 (I) 的化合物： 其中 R₁、R₂、R₃ 和 A 如描述中所定义，以及它们的光学异构体、 及其与药学上可接受的酸或碱的加成盐。 药物。
• Synthesis of [11C]-S21007 a novel 5HT3 partial agonist as a potential tracer for PET studies
  作者：S. Guillouet、L. Barre、F. Gourand、M. C. Lasne、S. Rault

  DOI：10.1002/(sici)1099-1344(199604)38:4<367::aid-jlcr846>3.0.co;2-n

  日期：1996.4

  A novel selective and partial agonist S21007 (IC50 = 1nM) for 5HT(3) receptor studies in positron emission tomography, has been labelled with [ C-11]benzyl iodide in 40-50% radiochemical yield and 200-700mCi/mu mol in 60 min synthesis time.
• Prunier; Besret; Dauphin, Pharmaceutical Sciences, 1997, vol. 3, # 5-6, p. 311 - 314
  作者：Prunier、Besret、Dauphin、Lancelot、Bureau、Rault

  DOI：——

  日期：——
• Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines
  作者：Sylvain Rault、Jean-Charles Lancelot、Hervé Prunier、Max Robba、Pierre Renard、Philippe Delagrange、Bruno Pfeiffer、Daniel-Henri Caignard、Béatrice Guardiola-Lemaitre、Michel Hamon

  DOI：10.1021/jm950543x

  日期：1996.1.1

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.
• Synthesis of aminopyrrolo[1,2-a]thieno[3,2-e]pyrazine derivatives as serotoninergic 5-HT7 ligands
  作者：Grégoire Pavé、Saïd Lazar、Aurélien Lesnard、Sylvain Rault、Gérald Guillaumet

  DOI：10.3998/ark.5550190.0011.a11

  日期：——

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]pyrazine derivatives were prepared and evaluated to determine their affinity for the 5-HT7 receptor. Various substitutions on piperazine were explored as well as replacement of the piperazine by other amines.

  制备并评估了一系列哌嗪并吡咯并 [1,2-a] 噻吩并 [3,2-e] 吡嗪衍生物，以确定它们对 5-HT7 受体的亲和力。探索了哌嗪上的各种取代以及用其他胺替代哌嗪。