4-benzoyl-N-[5-[benzoyl(methyl)amino]-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazol-2-yl]-1H-pyrrole-2-carboxamide | 1095269-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzoyl-N-[5-[benzoyl(methyl)amino]-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazol-2-yl]-1H-pyrrole-2-carboxamide
• CAS: 1095269-18-3
• 化学式: C₃₄H₃₂N₆O₄
• 分子量: 588.666
• InChiKey: VEVVLZCFRQUSAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[2-amino-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazol-5-yl]-N-methylbenzamide 、 4-苯甲酰基-1H-吡咯-2-羧酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到4-benzoyl-N-[5-[benzoyl(methyl)amino]-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazol-2-yl]-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  2-Aminobenzimidazoles as potent ITK antagonists: de novo design of a pyrrole system targeting additional hydrogen bonding interaction

  摘要：

  Based on information from molecular modeling, a series of 2-aminobenzimidazoles with pyrrole moieties were designed and synthesized as ITK antagonists. Results showed that a significant improvement of intrinsic and cell-based potency was achieved. X-ray crystallographic analysis of an inhibitor complex with ITK confirmed the prediction from the de novo design that the pyrrole moiety of the inhibitor would form an additional hydrogen bonding interaction with Glu436 in the catalytic domain, and hence improve overall binding affinity of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.057

文献信息

• 2-Aminobenzimidazoles as potent ITK antagonists: de novo design of a pyrrole system targeting additional hydrogen bonding interaction
  作者：Ho Yin Lo、Jörg Bentzien、Andre White、Chuk C. Man、Roman W. Fleck、Steven S. Pullen、Hnin Hnin Khine、Josephine King、Joseph R. Woska、John P. Wolak、Mohammed A. Kashem、Gregory P. Roth、Hidenori Takahashi

  DOI：10.1016/j.tetlet.2008.10.057

  日期：2008.12

  Based on information from molecular modeling, a series of 2-aminobenzimidazoles with pyrrole moieties were designed and synthesized as ITK antagonists. Results showed that a significant improvement of intrinsic and cell-based potency was achieved. X-ray crystallographic analysis of an inhibitor complex with ITK confirmed the prediction from the de novo design that the pyrrole moiety of the inhibitor would form an additional hydrogen bonding interaction with Glu436 in the catalytic domain, and hence improve overall binding affinity of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.