(1H-benzoimidazol-2-yl)-(3-morpholin-4-yl-propyl)amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (1H-benzoimidazol-2-yl)-(3-morpholin-4-yl-propyl)amine
• 英文别名: N-(3-morpholinopropyl)-1H-benzo[d]imidazol-2-amine；N-(3-morpholin-4-ylpropyl)-1,3-dihydrobenzimidazol-2-imine
• 化学式: C₁₄H₂₀N₄O
• 分子量: 260.339
• InChiKey: PABPIVSFSIPKPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2,4-二氯苯氧基)甲基]环氧乙烷 、 (1H-benzoimidazol-2-yl)-(3-morpholin-4-yl-propyl)amine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2,4-Dichlorophenoxy)-3-[2-(3-morpholin-4-ylpropylamino)benzimidazol-1-yl]propan-2-ol
  参考文献：
  名称：

  Acinetobacter baumannii OxPhos inhibitors as selective anti-infective agents

  摘要：

  The Gram-negative bacterium Acinetobacter baumannii is an opportunistic pathogen in humans and infections are poorly treated by current therapy. Recent emergence of multi-drug resistant strains and the lack of new antibiotics demand an immediate action for development of new anti-Acinetobacter agents. To this end, oxidative phosphorylation (OxPhos) was identified as a novel target for drug discovery research. Consequently, a library of similar to 10,000 compounds was screened using a membrane-based ATP synthesis assay. One hit identified was the 2-iminobenzimidazole 1 that inhibited the OxPhos of A. baumannii with a modestly high selectivity against mitochondrial OxPhos, and displayed an MIC of 25 mu M (17 mu g/mL) against the pathogen. The 2-iminobenzimidazole 1 was found to inhibit the type 1 NADH-quinone oxidoreductase (NDH-1) of A. baumannii OxPhos by a biochemical approach. Among various derivatives that were synthesized to date, des-hydroxy analog 5 is among the most active with a relatively tight SAR requirement for the N'-aminoalkyl side chain. Analog 5 also showed less cytotoxicity against NIH3T3 and HepG2 mammalian cell lines, demonstrating the potential for this series of compounds as anti-Acinetobacter agents. Additional SAR development and target validation is underway. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.020
• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 2-氯苯并咪唑 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 5.0h， 以14%的产率得到(1H-benzoimidazol-2-yl)-(3-morpholin-4-yl-propyl)amine
  参考文献：
  名称：

  [EN] NOVEL ANTI-INFECTIVE COMPOUNDS AND METHODS USING SAME
  [FR] NOUVEAUX COMPOSÉS ANTI-INFECTIEUX ET LEURS MÉTHODES D'UTILISATION

  摘要：

  本发明涉及一种治疗或预防需要的主体中的细菌感染的方法。该方法包括向该主体施用本发明至少一种化合物的治疗有效量。在某些实施方式中，细菌为革兰氏阴性菌。在其他实施方式中，细菌为厌氧菌。

  公开号：

  WO2016077541A1