4-(piperazin-1-yl)-1H-pyrrolo[3,2-c]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(piperazin-1-yl)-1H-pyrrolo[3,2-c]quinoline
• 英文别名: 4-piperazin-1-yl-1H-pyrrolo[3,2-c]quinoline
• 化学式: C₁₅H₁₆N₄
• 分子量: 252.319
• InChiKey: MXYPWAJIIBGPMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴苯磺酰氯 、 4-(piperazin-1-yl)-1H-pyrrolo[3,2-c]quinoline 、 tert-butyl-4-(1-((2-bromophenyl)sulfonyl)-1H-pyrrolo[3,2-c]quinolin-4-yl)piperazine-1-carboxylate 在 (叔丁基亚氨基)三(吡咯烷)膦 、 盐酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 8.0h， 以92%的产率得到1-[(2-bromophenyl)sulfonyl]-4-(piperazin-1-yl)-1H-pyrrolo[3,2-c]quinoline dihydrochloride
  参考文献：
  名称：

  Structure-Based Design and Optimization of FPPQ, a Dual-Acting 5-HT₃ and 5-HT₆ Receptor Antagonist with Antipsychotic and Procognitive Properties

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00224
• 作为产物：
  描述：

  methyl 2,5-dihydro-2-(2-nitrophenyl)-1-tosyl-1H-pyrrole-3-carboxylate 在 palladium on activated charcoal 、 氢气 、 三乙胺 、 sodium t-butanolate 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.0h， 生成 4-(piperazin-1-yl)-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Structure-Based Design and Optimization of FPPQ, a Dual-Acting 5-HT₃ and 5-HT₆ Receptor Antagonist with Antipsychotic and Procognitive Properties

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00224

文献信息

• [EN] PYRROLOQUINOLINE DERIVATIVES AS 5-HT6 ANTAGONISTS, PREPARATION METHOD AND USE THEREOF<br/>[FR] DÉRIVÉS DE PYRROLOQUINOLINE UTILISÉS COMME ANTAGONISTES DE 5-HT6, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION
  申请人：UNIV JAGIELLOŃSKI

  公开号：WO2015012704A1

  公开（公告）日：2015-01-29

  This invention concerns pyrroloquinoline derivatives as antagonists of 5-HT6 receptors, to methods for the preparation of these compounds and to novel intermediates useful for their synthesis. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in schizophrenia, anxiety, depression, maniac depression, epilepsy, obsessive compulsive disorders, mood disorders, migraine, Alzheimer's disease, age related cognitive decline, mild cognitive impairment, sleep disorders, eating disorders, anorexia, bulimia, panic attacks, attention deficit hyperactivity disorder, attention deficit disorder, Parkinson's disease, Huntington's disease, withdrawal from abuse of cocaine, ethanol, nicotine or benzodiazepines, pain, obesity and type-2 diabetes, functional bowel disorder, Irritable Bowel Syndrome. The compounds have the general formula (XIV), wherein the symbols have the meanings given in the description.

  这项发明涉及吡咯喹啉衍生物作为5-HT6受体拮抗剂，以及制备这些化合物的方法和用于它们合成的新型中间体。该发明还涉及这些化合物和组合物的用途，特别是它们在向患者施用以达到治疗精神分裂症、焦虑、抑郁症、躁狂抑郁症、癫痫、强迫性障碍、情绪障碍、偏头痛、阿尔茨海默病、年龄相关认知衰退、轻度认知功能障碍、睡眠障碍、进食障碍、厌食症、贪食症、惊恐发作、注意力缺陷多动障碍、注意力缺陷障碍、帕金森病、亨廷顿病、戒除可卡因、乙醇、尼古丁或苯二氮卓类药物滥用、疼痛、肥胖和2型糖尿病、功能性肠道紊乱、肠易激综合征等方面的用途。这些化合物具有一般式（XIV），其中符号的含义如描述中所述。
• PYRROLOQUINOLINE DERIVATIVES AS 5-HT6 ANTAGONISTS, PREPARATION METHOD AND USE THEREOF
  申请人：UNIWERSYTET JAGIELLONSKI

  公开号：EP3027613B1

  公开（公告）日：2018-03-28
• Pyrroloquinoline Derivatives as 5-HT6 Antagonists, Preparation Method and Use Thereof
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20160159790A1

  公开（公告）日：2016-06-09

  This invention concerns pyrroloquinoline derivatives as antagonists of 5-HT6 receptors, to methods for the preparation of these compounds and to novel intermediates useful for their synthesis. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in schizophrenia, anxiety, depression, maniac depression, epilepsy, obsessive compulsive disorders, mood disorders, migraine, Alzheimer's disease, age related cognitive decline, mild cognitive impairment, sleep disorders, eating disorders, anorexia, bulimia, panic attacks, attention deficit hyperactivity disorder, attention deficit disorder, Parkinson's disease, Huntington's disease, withdrawal from abuse of cocaine, ethanol, nicotine or benzodiazepines, pain, obesity and type-2 diabetes, functional bowel disorder, Irritable Bowel Syndrome. The compounds have the general formula (XIV), wherein the symbols have the meanings given in the description.
• US9676772B2
  申请人：——

  公开号：US9676772B2

  公开（公告）日：2017-06-13
• Structure-Based Design and Optimization of FPPQ, a Dual-Acting 5-HT₃ and 5-HT₆ Receptor Antagonist with Antipsychotic and Procognitive Properties
  作者：Paweł Zajdel、Katarzyna Grychowska、Szczepan Mogilski、Rafał Kurczab、Grzegorz Satała、Ryszard Bugno、Tomasz Kos、Joanna Gołębiowska、Natalia Malikowska-Racia、Agnieszka Nikiforuk、Séverine Chaumont-Dubel、Xavier Bantreil、Maciej Pawłowski、Jean Martinez、Gilles Subra、Frédéric Lamaty、Philippe Marin、Andrzej J. Bojarski、Piotr Popik

  DOI：10.1021/acs.jmedchem.1c00224

  日期：2021.9.23