1-(benzimidazol-5(6)-yl)-4-methylpiperazine

• 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-(benzimidazol-5(6)-yl)-4-methylpiperazine
• 英文别名: 6-(4-methylpiperazin-1-yl)-1H-benzimidazole
• 化学式: C₁₂H₁₆N₄
• 分子量: 216.286
• InChiKey: GMGAOIPGKMEZHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzimidazol-5(6)-yl)-4-methylpiperazine 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 tert-butyl 2-iodo-5-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole-1-carboxylate
  参考文献：
  名称：

  BENZIMIDAZOLE DERIVATIVES AS GPX4 INHIBITORS

  摘要：

  The present disclosure provides a compounds of Formula (I) or a pharmaceutically acceptable salt thereof and its use in,e.g. treating a condition, disease, or disorder in which inhibiting GPX4 in a subject is of therapeutic benefit, specifically in treating cancer or autoimmune diseases. This disclosure also features a composition containing the same as well as methods of using and making the same.

  公开号：

  WO2024129780A1
• 作为产物：
  描述：

  1-(4-methoxybenzyl)-5-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole 在 三氟乙酸 作用下， 反应 3.0h， 生成 1-(benzimidazol-5(6)-yl)-4-methylpiperazine
  参考文献：
  名称：

  [EN] SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
  [FR] BENZIMIDAZOLE CARBOXAMIDES SUBSTITUÉS ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES MÉDICAUX

  摘要：

  这项发明提供了替代苯并咪唑羧酰胺及相关化合物，含有这些化合物的组合物，医疗工具包，以及使用这些化合物和组合物治疗患者的医疗疾病的方法，例如癌症、溶酶体贮积症、神经退行性疾病、炎症性疾病。

  公开号：

  WO2021055591A1

文献信息

• Benzimidazole Derivatives as New Serotonin 5-HT₆ Receptor Antagonists. Molecular Mechanisms of Receptor Inactivation
  作者：Tania de la Fuente、Mar Martín-Fontecha、Jessica Sallander、Bellinda Benhamú、Mercedes Campillo、Rocío A. Medina、Lucie P. Pellissier、Sylvie Claeysen、Aline Dumuis、Leonardo Pardo、María L. López-Rodríguez

  DOI：10.1021/jm901672k

  日期：2010.2.11

  On the basis of our previously described pharmacophore model for serotonin 5-HT6 receptor (5-HT6R) antagonists, we have designed, synthesized, and pharmacologically characterized a series of benzimidazole derivatives 1-20 that represent a new family of potent antagonists at the human 5-HT6R. Site-directed mutagenesis and a beta(2)-adrenoceptor-based homology model of the 5-HT6R were used to predict the mode of binding of antagonist SB-258585 and the new synthesized ligands. Substitution of W6.48, F6.52, or N6.55 by Ala fully impedes compound 4 to block 5-HT-induced activation. Thus, we propose that D3.32 in TM 3 anchors the protonated piperazine ring, the benzimidazole, ring expands parallel to EL 2 to hydrogen bond N6.55 in TM 6, and the aromatic ring is placed between TMs 3 and 5 in CH2-containing compounds and between TMs 3 and 6 in CO-containing compounds. This combined experimental and computational study has permitted to propose the molecular mechanisms by which the new benzimidazole derivatives act as 5-HT6R antagonists.
• Pd(0) Amination of Benzimidazoles as an Efficient Method towards New (Benzimidazolyl)piperazines with High Affinity for the 5-HT1A Receptor
  作者：Marı́a L López-Rodrı́guez、Bellinda Benhamú、David Ayala、J.Luis Rominguera、Marta Murcia、José A Ramos、Alma Viso

  DOI：10.1016/s0040-4020(00)00225-8

  日期：2000.5

  New (benzimidazolyl)amines have been synthesized from 4- and 6-bromobenzimidazole derivatives via palladium-mediated amination reactions. Among them, (benzimidazol-4(7)-yl)piperazine derivatives have been shown to be a new family of high affinity 5-HT1A receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS<br/>[FR] BENZIMIDAZOLE CARBOXAMIDES SUBSTITUÉS ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES MÉDICAUX
  申请人：BIAL BIOTECH INVEST INC

  公开号：WO2021055591A1

  公开（公告）日：2021-03-25

  The invention provides substituted benzimidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

  这项发明提供了替代苯并咪唑羧酰胺及相关化合物，含有这些化合物的组合物，医疗工具包，以及使用这些化合物和组合物治疗患者的医疗疾病的方法，例如癌症、溶酶体贮积症、神经退行性疾病、炎症性疾病。
• BENZIMIDAZOLE DERIVATIVES AS GPX4 INHIBITORS
  申请人：[en]SONATA THERAPEUTICS, INC.

  公开号：WO2024129780A1

  公开（公告）日：2024-06-20

  The present disclosure provides a compounds of Formula (I) or a pharmaceutically acceptable salt thereof and its use in,e.g. treating a condition, disease, or disorder in which inhibiting GPX4 in a subject is of therapeutic benefit, specifically in treating cancer or autoimmune diseases. This disclosure also features a composition containing the same as well as methods of using and making the same.