1-(benzofuran-5-yl)piperazine | 206347-31-1

• 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: 1-(benzofuran-5-yl)piperazine
• 英文别名: 1-(5-benzofuranyl)Piperazine；1-(1-benzofuran-5-yl)piperazine
• CAS: 206347-31-1
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: PYUFUUDEYQJLPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzofuran-5-yl)piperazine 生成 1-(benzofuran-5-yl)-4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazine
  参考文献：
  名称：

  PHENYLPYRIDINE CARBONYL PIPERAZINE DERIVATIVE

  摘要：

  公开号：

  EP1396487B1
• 作为产物：
  描述：

  5-溴苯并呋喃 在 三(邻甲基苯基)磷 、 三氟乙酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1-(benzofuran-5-yl)piperazine
  参考文献：
  名称：

  Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine

  摘要：

  Reaction of a series of bicyclic bromoarenes with N-tert-butoxycarbonylpiperazine (N-Boc-piperazine) under palladium-calalysed coupling conditions followed by routine removal of the Boc group with trifluoroacetic acid in dichloromethane gave the corresponding arylpiperazines in moderate to good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00179-8

文献信息

• Synthesis and Structure−Activity Relationship in a Class of Indolebutylpiperazines as Dual 5-HT_1A Receptor Agonists and Serotonin Reuptake Inhibitors
  作者：Timo Heinrich、Henning Böttcher、Rolf Gericke、Gerd D. Bartoszyk、Soheila Anzali、Christoph A. Seyfried、Hartmut E. Greiner、Christoph van Amsterdam

  DOI：10.1021/jm040793q

  日期：2004.9.1

  Systematic structural modifications of indolealkylphenylpiperazines led to improved selectivity and affinity within this class of 5-HT(1A) receptor agonists. Introduction of electron-withdrawing groups in position 5 on the indole raises serotonin transporter affinity, and the cyano group proved to be the best substituent here. 5-Fluoro and 5-cyano substituted indoles show comparable results in in vitro

  吲哚烷基苯基哌嗪的系统结构修饰导致此类5-HT（1A）受体激动剂的选择性和亲和力提高。在吲哚的5位引入吸电子基团提高了5-羟色胺转运蛋白的亲和力，并且氰基被证明是此处最好的取代基。5-氟和5-氰基取代的吲哚在体外和体内试验中显示出可比的结果，并且通过计算分子静电势和偶极矩来支持这些取代基之间的生物等排。在离体（对氯苯丙胺测定）和体内（超声发声）测试中进一步检查了显示出有希望的体外数据的化合物。芳基哌嗪部分的优化表明，5-苯并呋喃基-2-羧酰胺最适合增加5-HT转运蛋白和5-HT（1A）受体的亲和力并抑制D（2）受体的结合。5- [4- [4-（5-氰基-3-吲哚基）丁基] -1-哌嗪基]苯并呋喃-2-羧酰胺29（维拉唑酮，EMD 68843）被确定为高选择性5-HT（1A）受体激动剂[GTPgammaS，ED（50）= 1.1 nM]，具有亚纳摩尔的5-HT（1A）亲和力[IC（50）= 0
• [EN] 5-[(PIPERAZIN-1-YL)-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS INHIBITORS FOR THE TREATMENT OF OSTEOARTHRITIS<br/>[FR] DÉRIVÉS 5-[(PIPÉRAZINE-1-YL) -3-OXO-PROPYL]-IMIDAZOLIDINE -2,4-DIONE COMME INHIBITEURS D'ADAMTS POUR LE TRAITEMENT DE L'ARTHROSE
  申请人：GALAPAGOS NV

  公开号：WO2016102347A1

  公开（公告）日：2016-06-30

  The present invention discloses compounds according to Formula (I), wherein R, R2, R3a, R3b, and Cy are as defined herein. The present invention discloses compounds inhibiting ADAMTS, methods for their production, pharmaceutical compositions comprising the same and methods for the prophylaxis and/or treatment of inflammatory conditions and/or diseases involving degradation of cartilage and/or disruption of cartilage homeostasis.

  本发明公开了根据式(I)的化合物，其中R、R2、R3a、R3b和Cy如本文所定义。本发明公开了抑制ADAMTS的化合物、其制备方法、包含该化合物的药物组合物以及用于预防和/或治疗涉及软骨降解和/或软骨稳态破坏的炎症状况和/或疾病的方法。
• PROCESS OF A QUATERNARY AMMONIUM SALT USING PHOSPHATE
  申请人：AE Nobuyuki

  公开号：US20110263848A1

  公开（公告）日：2011-10-27

  The present invention relates to a novel process for preparing quaternary ammonium salt derivatives.

  本发明涉及一种制备季铵盐衍生物的新工艺。
• PROCESS OF A QUATERNARY AMMONIUM SALT
  申请人：AE Nobuyuki

  公开号：US20110263847A1

  公开（公告）日：2011-10-27

  The present invention relates to a novel process for preparing quaternary ammonium salt derivatives.

  本发明涉及一种制备季铵盐衍生物的新工艺。
• Process for the Preparation of 5-(4-[4-(5-Cyano-3-Indolyl)Butyl]-1-Piperazinyl)Benzofuran-2-Carboxamide
  申请人：Bathe Andreas

  公开号：US20080293943A1

  公开（公告）日：2008-11-27

  The invention relates to a process for the preparation of 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide and/or one of its physiologically acceptable salts, characterised in that a compound of the formula (I), in which L denotes Cl, Br, I, SO 2 F, SO 2 CF 3 , SO 2 C 2 F 5 , is reacted with 3-(4-piperazin-1-ylbutyl)indole-5-carbonitrile by transition-metal-catalysed coupling by means of Pd complexes, and/or in that the 5-(4[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide formed is converted into one of its acid-addition salts by treatment with an acid, and to a second process, characterised in that a compound of the formula (II), as the base or HX salt (where X=Cl, BR), is reacted with 3-(4-oxobutyl)-1H-indole-5-carbonitrile by reductive amination, and/or in that 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide is converted into one of its acid-addition salts by treatment with an acid.

  本发明涉及一种制备5-(4-[4-(5-氰基-3-吲哚基)丁基]-1-哌嗪基)苯并呋喃-2-羧酰胺和/或其生理上可接受的盐的方法，其特征在于将式(I)的化合物与3-(4-哌嗪-1-基丁基)吲哚-5-碳腈经过Pd配合物的过渡金属催化偶联反应，其中L表示Cl、Br、I、SO2F、SO2CF3、SO2C2F5，或者将形成的5-(4-[4-(5-氰基-3-吲哚基)丁基]-1-哌嗪基)苯并呋喃-2-羧酰胺通过处理酸转化为其酸加成盐中的一种；以及第二种方法，其特征在于将式(II)的化合物作为碱或HX盐（其中X=Cl、BR）与3-(4-氧代丁基)-1H-吲哚-5-碳腈通过还原胺化反应，或者将5-(4-[4-(5-氰基-3-吲哚基)丁基]-1-哌嗪基)苯并呋喃-2-羧酰胺通过处理酸转化为其酸加成盐中的一种。