5-benzimidazol-1-yl-2-nitroaniline | 131885-66-0

• 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: 5-benzimidazol-1-yl-2-nitroaniline
• 英文别名: 5-(1H-Benzimidazol-1-yl)-2-nitrobenzenamine；5-(benzimidazol-1-yl)-2-nitroaniline
• CAS: 131885-66-0
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: IVPOSGHNQXTIQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzimidazol-1-yl-2-nitroaniline 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-Benzoimidazol-1-yl-benzene-1,2-diamine
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024
• 作为产物：
  描述：

  2-氯-4-氟硝基苯 在 氨 、 sodium hydride 作用下， 以 乙二醇甲醚 为溶剂， 50.0~150.0 ℃ 、3.3 MPa 条件下， 反应 77.0h， 生成 5-benzimidazol-1-yl-2-nitroaniline
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024

文献信息

• Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles
  作者：Timur Gungor、Andre Fouquet、Jean Marie Teulon、Daniel Provost、Michele Cazes、Alix Cloarec

  DOI：10.1021/jm00101a024

  日期：1992.11

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.