N-(1-(3-amino-3-oxopropyl)-5-(N-methylacetamido)-1H-benzo[d]imidazol-2-yl)-4-cyanobenzamide | 1091610-53-5

• 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: N-(1-(3-amino-3-oxopropyl)-5-(N-methylacetamido)-1H-benzo[d]imidazol-2-yl)-4-cyanobenzamide
• 英文别名: N-[5-[acetyl(methyl)amino]-1-(3-amino-3-oxopropyl)benzimidazol-2-yl]-4-cyanobenzamide
• CAS: 1091610-53-5
• 化学式: C₂₁H₂₀N₆O₃
• 分子量: 404.428
• InChiKey: CAHMXEROAVSIFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对氰基苯甲酸 、 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-(1-(3-amino-3-oxopropyl)-5-(N-methylacetamido)-1H-benzo[d]imidazol-2-yl)-4-cyanobenzamide
  参考文献：
  名称：

  Discovery, SAR and X-ray structure of 1H-benzimidazole-5-carboxylic acid cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk)

  摘要：

  A series of novel potent benzimidazole based inhibitors of interleukin-2 T-cell kinase (Itk) were prepared. In this report, we discuss the structure-activity relationship (SAR), selectivity, and cell-based activity for the series. We also discuss the SAR associated with an X-ray structure of one of the small-molecule inhibitors bound to ITK. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.015

文献信息

• Crystal structure of the ITK kinase domain
  申请人：Bentzien Martin Joerg

  公开号：US20070032403A1

  公开（公告）日：2007-02-08

  Disclosed are polypeptides encoding the ITK kinase domain and nucleic acids encoding such polypeptides, crystal structures of various polypeptide-ligand complexes comprising the ITK kinase domain bound to a ligand, methods of producing the aforementioned polypeptides and nucleic acids which encode them and methods of producing crystal structures of the aforementioned polypeptides comprising the ITK kinase domain bound to a ligand.
• Discovery, SAR and X-ray structure of 1H-benzimidazole-5-carboxylic acid cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk)
  作者：Kevin J. Moriarty、Hidenori Takahashi、Steven S. Pullen、Hnin Hnin Khine、Rosemarie H. Sallati、Ernest L. Raymond、Joseph R. Woska、Deborah D. Jeanfavre、Gregory P. Roth、Michael P. Winters、Lei Qiao、Declan Ryan、Renee DesJarlais、Darius Robinson、Matthew Wilson、Mark Bobko、Brian N. Cook、Ho Yin Lo、Peter A. Nemoto、Mohammed A. Kashem、John P. Wolak、André White、Ronald L. Magolda、Bruce Tomczuk

  DOI：10.1016/j.bmcl.2008.09.015

  日期：2008.10

  A series of novel potent benzimidazole based inhibitors of interleukin-2 T-cell kinase (Itk) were prepared. In this report, we discuss the structure-activity relationship (SAR), selectivity, and cell-based activity for the series. We also discuss the SAR associated with an X-ray structure of one of the small-molecule inhibitors bound to ITK. (c) 2008 Elsevier Ltd. All rights reserved.