2-(4-aminophenylamino)benzimidazole | 133929-18-7

• 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: 2-(4-aminophenylamino)benzimidazole
• 英文别名: N-(1H-Benzoimidazol-2-yl)-benzene-1,4-diamine；4-N-(1H-benzimidazol-2-yl)benzene-1,4-diamine
• CAS: 133929-18-7
• 化学式: C₁₃H₁₂N₄
• mdl: MFCD00569560
• 分子量: 224.265
• InChiKey: QTKVVJXYEASQLY-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C(Solv: methanol (67-56-1))
• 沸点：
  482.6±47.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)
• 溶解度：
  25.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenylamino)benzimidazole 在 calcium carbonate 、 mercury(II) oxide 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 N-(2-benzimidazolyl)-N'-(2-benzoxazolyl)-1,4-diaminobenzene
  参考文献：
  名称：

  Garin, Javier; Melendez, Enrique; Merchan, Francisco L., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 2, p. 359 - 363

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基苯并咪唑 在 三氯氧磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 2.25h， 生成 2-(4-aminophenylamino)benzimidazole
  参考文献：
  名称：

  From Cells to Mice to Target: Characterization of NEU-1053 (SB-443342) and Its Analogues for Treatment of Human African Trypanosomiasis

  摘要：

  Human African trypanosomiasis is a neglected tropical disease that is lethal if left untreated. Existing therapeutics have limited efficacy and severe associated toxicities. 2-(2-(((3-((1H-Benzo[d]imidazol-2-yl)amino)propyl)amino)methyl)-4,6-dichloro-1H-indol-1-yl)ethan-1-ol (NEU-1053) has recently been identified from a high-throughput screen of >42,000 compounds as a highly potent and fast-acting trypanocidal agent capable of curing a bloodstream infection of Trypanosoma brucei in mice. We have designed a library of analogues to probe the structureactivity relationship and improve the predicted central nervous system (CNS) exposure of NEU-1053. We report the activity of these inhibitors of T. brucei, the efficacy of NEU-1053 in a murine CNS model of infection, and identification of the target of NEU-1053 via X-ray crystallography.

  DOI：

  10.1021/acsinfecdis.6b00202

文献信息

• GARIN, JAVIER;MELENDEZ, ENRIQUE;MERCHAN, FRANCISCO L.;MERINO, PEDRO;ORDUN+, J. HETEROCYCL. CHEM., 28,(1991) N, C. 359-363
  作者：GARIN, JAVIER、MELENDEZ, ENRIQUE、MERCHAN, FRANCISCO L.、MERINO, PEDRO、ORDUN+

  DOI：——

  日期：——
• BENZIMIDAZOL-2-AMINES AS MIDH1 INHIBITORS
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3105210B1

  公开（公告）日：2019-01-30
• Garin, Javier; Melendez, Enrique; Merchan, Francisco L., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 2, p. 359 - 363
  作者：Garin, Javier、Melendez, Enrique、Merchan, Francisco L.、Merino, Pedro、Orduna, Jesus、Tejero, Tomas

  DOI：——

  日期：——
• From Cells to Mice to Target: Characterization of NEU-1053 (SB-443342) and Its Analogues for Treatment of Human African Trypanosomiasis
  作者：William G. Devine、Rosario Diaz-Gonzalez、Gloria Ceballos-Perez、Domingo Rojas、Takashi Satoh、Westley Tear、Ranae M. Ranade、Ximena Barros-Álvarez、Wim G. J. Hol、Frederick S. Buckner、Miguel Navarro、Michael P. Pollastri

  DOI：10.1021/acsinfecdis.6b00202

  日期：2017.3.10

  Human African trypanosomiasis is a neglected tropical disease that is lethal if left untreated. Existing therapeutics have limited efficacy and severe associated toxicities. 2-(2-(((3-((1H-Benzo[d]imidazol-2-yl)amino)propyl)amino)methyl)-4,6-dichloro-1H-indol-1-yl)ethan-1-ol (NEU-1053) has recently been identified from a high-throughput screen of >42,000 compounds as a highly potent and fast-acting trypanocidal agent capable of curing a bloodstream infection of Trypanosoma brucei in mice. We have designed a library of analogues to probe the structureactivity relationship and improve the predicted central nervous system (CNS) exposure of NEU-1053. We report the activity of these inhibitors of T. brucei, the efficacy of NEU-1053 in a murine CNS model of infection, and identification of the target of NEU-1053 via X-ray crystallography.