3-(1-Imidazolyl)-2-nitroaniline | 131885-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1-Imidazolyl)-2-nitroaniline
• 英文别名: 3-Imidazol-1-yl-2-nitroaniline
• CAS: 131885-46-6
• 化学式: C₉H₈N₄O₂
• 分子量: 204.188
• InChiKey: XAQOYTATNRINLI-UHFFFAOYSA-N

物化性质

• 沸点：
  462.7±35.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  3-(1-Imidazolyl)-2-nitroaniline 在 镍 氢气 作用下， 以 甲醇 为溶剂， 25.0~180.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 4-imidazol-1-yl-2-pyridin-4-yl-1H-benzimidazole
  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-硝基-3-氯-苯甲酰胺 在 氢氧化钾 、 溴 作用下， 反应 25.25h， 生成 3-(1-Imidazolyl)-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

• C-6 ring-substituted pyrido[1,2-a]benzimidazole derivatives useful in treating central nervous system disorders
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06358946B1

  公开（公告）日：2002-03-19

  A C-6 ring-substituted pyrido[1,2-a]benzimidazole derivative of the formula: methods of preparation and pharmaceutical compositions containing a substituted pyrido[1,2-a]benzimidzole derivative as the active ingredient are disclosed. The substituted pyrido[1,2-a]benzimidazole derivatives are useful in the treatment of central nervous system disorders.

  一种C-6环取代的吡啶并[1,2-a]苯并咪唑衍生物的配方：公开了制备方法和含有取代的吡啶并[1,2-a]苯并咪唑衍生物作为活性成分的药物组合物。这些取代的吡啶并[1,2-a]苯并咪唑衍生物在治疗中枢神经系统疾病方面具有用途。
• C-6 RING-SUBSTITUTED PYRIDO[1,2-a]BENZIMIDAZOLE DERIVATIVES USEFUL IN TREATING CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1200433B1

  公开（公告）日：2006-03-22
• C-6 RING-SUBSTITUTED PYRIDO 1,2- i a /i ]BENZIMIDAZOLE DERIVATIVES USEFUL IN TREATING CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1200433A1

  公开（公告）日：2002-05-02
• US6358946B1
  申请人：——

  公开号：US6358946B1

  公开（公告）日：2002-03-19
• [EN] C-6 RING-SUBSTITUTED PYRIDO[1,2-a]BENZIMIDAZOLE DERIVATIVES USEFUL IN TREATING CENTRAL NERVOUS SYSTEM DISORDERS<br/>[FR] DERIVES DE PYRIDO[1,2-a]BENZIMIDAZOLE SUBSTITUES EN C-6 UTILES DANS LE TRAITEMENT DES TROUBLES DU SYSTEME NERVEUX CENTRAL
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2001009132A1

  公开（公告）日：2001-02-08

  A C-6 ring-substituted pyrido[1,2-a]benzimidazole derivative of formula (1): methods of preparation and pharmaceutical compositions containing a substituted pyrido[1,2-a]benzimidazole derivative as the active ingredient are disclosed. The substituted pyrido[1,2-a]benzimidazole derivatives are useful in the treatment of central nervous system disorders.