2-amino-1-(3-amino-3-oxopropyl)-N-cyclohexyl-N-methyl-1H-benzo[d]imidazole-5-carboxamide | 943989-28-4

• 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-amino-1-(3-amino-3-oxopropyl)-N-cyclohexyl-N-methyl-1H-benzo[d]imidazole-5-carboxamide
• CAS: 943989-28-4
• 化学式: C₁₈H₂₅N₅O₂
• 分子量: 343.429
• InChiKey: IVEBGCZFHBHLDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107.24
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-噻吩甲酰氯 、 2-amino-1-(3-amino-3-oxopropyl)-N-cyclohexyl-N-methyl-1H-benzo[d]imidazole-5-carboxamide 在 吡啶 作用下， 生成 1-(3-amino-3-oxopropyl)-N-cyclohexyl-N-methyl-2-(thiophene-2-carboxamido)-1H-benzo[d]imidazole-5-carboxamide
  参考文献：
  名称：

  Hit-to-lead studies on benzimidazole inhibitors of ITK: Discovery of a novel class of kinase inhibitors

  摘要：

  Benzimidazole 1 was identified as a selective inhibitor of ITK by high throughput screening. Hit-to-lead studies defined the SAR at all three substituents. Reversing the amide linkage at C6 led to 16, with a fivefold improvement of potency. This enhancement is rationalized by the conformational preference of the substituent. A model for the binding of the benzimidazoles to the ATP-binding site of ITK is proposed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.045
• 作为产物：
  描述：

  4-((3-amino-3-oxopropyl)amino)-N-cyclohexyl-N-methyl-3-nitrobenzamide 在 palladium on activated charcoal 甲酸铵 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-amino-1-(3-amino-3-oxopropyl)-N-cyclohexyl-N-methyl-1H-benzo[d]imidazole-5-carboxamide
  参考文献：
  名称：

  Hit-to-lead studies on benzimidazole inhibitors of ITK: Discovery of a novel class of kinase inhibitors

  摘要：

  Benzimidazole 1 was identified as a selective inhibitor of ITK by high throughput screening. Hit-to-lead studies defined the SAR at all three substituents. Reversing the amide linkage at C6 led to 16, with a fivefold improvement of potency. This enhancement is rationalized by the conformational preference of the substituent. A model for the binding of the benzimidazoles to the ATP-binding site of ITK is proposed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.045