4-cyano-N-(5-((cyclohexyl(methyl)amino)methyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)benzamide | 1089672-62-7

• 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: 4-cyano-N-(5-((cyclohexyl(methyl)amino)methyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)benzamide
• 英文别名: 4-cyano-N-[5-[[cyclohexyl(methyl)amino]methyl]-1-(3-methoxypropyl)benzimidazol-2-yl]benzamide
• CAS: 1089672-62-7
• 化学式: C₂₇H₃₃N₅O₂
• 分子量: 459.591
• InChiKey: HOWZJLASEFUNIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基环己胺 、 4-cyano-N-(5-formyl-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)benzamide 在 triethyl orthoformate 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以42%的产率得到4-cyano-N-(5-((cyclohexyl(methyl)amino)methyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)benzamide
  参考文献：
  名称：

  5-Aminomethyl-1H-benzimidazoles as orally active inhibitors of inducible T-cell kinase (Itk)

  摘要：

  A series of novel 5-aminomethyl-1H-benzimidazole based inhibitors of Itk were prepared. Structure activity relationships, selectivity and cell activity are reported for this series. Compound 2, a potent and selective antagonist of Itk, inhibited anti-CD3 antibody induced IL-2 production in vivo in mice. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.016

文献信息

• 5-Aminomethyl-1H-benzimidazoles as orally active inhibitors of inducible T-cell kinase (Itk)
  作者：Michael P. Winters、Darius J. Robinson、Hnin Hnin Khine、Steven S. Pullen、Joseph R. Woska、Ernest L. Raymond、Rosemarie Sellati、Charles L. Cywin、Roger J. Snow、Mohammed A. Kashem、John P. Wolak、Josephine King、Paul V. Kaplita、Lisa H. Liu、Thomas M. Farrell、Renee DesJarlais、Gregory P. Roth、Hidenori Takahashi、Kevin J. Moriarty

  DOI：10.1016/j.bmcl.2008.09.016

  日期：2008.10

  A series of novel 5-aminomethyl-1H-benzimidazole based inhibitors of Itk were prepared. Structure activity relationships, selectivity and cell activity are reported for this series. Compound 2, a potent and selective antagonist of Itk, inhibited anti-CD3 antibody induced IL-2 production in vivo in mice. (c) 2008 Elsevier Ltd. All rights reserved.