N-[1-(3-amino-3-oxopropyl)-5-[benzoyl(methyl)amino]benzimidazol-2-yl]-5-(1-cyanoprop-1-en-2-yl)thiophene-2-carboxamide | 1092486-88-8

• 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-[benzoyl(methyl)amino]benzimidazol-2-yl]-5-(1-cyanoprop-1-en-2-yl)thiophene-2-carboxamide
• CAS: 1092486-88-8
• 化学式: C₂₇H₂₄N₆O₃S
• 分子量: 512.592
• InChiKey: CVIBKQQGYYKXTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  137.34
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-[(2E)-5-[benzene(methyl)amido]-1-(2-carbamoylethyl)-2,3-dihydro-1H-1,3-benzodiazol-2-ylidene]-5-acetylthiophene-2-carboxamide 、 (氰基甲基)三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 N-[1-(3-amino-3-oxopropyl)-5-[benzoyl(methyl)amino]benzimidazol-2-yl]-5-(1-cyanoprop-1-en-2-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  2-Aminobenzimidazoles as potent ITK antagonists: trans-stilbene-like moieties targeting the kinase specificity pocket

  摘要：

  Based on the information from molecular modeling and X-ray crystal structures, the kinase specificity pocket of ITK could be occupied upon extension of the right-hand-side of the 2-benzimidazole core of the inhibitors. 2-Aminobenzimidazoles with a trans-stilbene-like extension were designed and synthesized as novel ITK antagonists. Significant improvement on binding affinity and cellular activity were obtained through the trans-stilbene-like antagonists. Several compounds showed inhibitory activity in an IL-2 functional assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.098

文献信息

• 2-Aminobenzimidazoles as potent ITK antagonists: trans-stilbene-like moieties targeting the kinase specificity pocket
  作者：Ho Yin Lo、Jörg Bentzien、Roman W. Fleck、Steven S. Pullen、Hnin Hnin Khine、Joseph R. Woska、Stanley Z. Kugler、Mohammed A. Kashem、Hidenori Takahashi

  DOI：10.1016/j.bmcl.2008.09.098

  日期：2008.12

  Based on the information from molecular modeling and X-ray crystal structures, the kinase specificity pocket of ITK could be occupied upon extension of the right-hand-side of the 2-benzimidazole core of the inhibitors. 2-Aminobenzimidazoles with a trans-stilbene-like extension were designed and synthesized as novel ITK antagonists. Significant improvement on binding affinity and cellular activity were obtained through the trans-stilbene-like antagonists. Several compounds showed inhibitory activity in an IL-2 functional assay. (C) 2008 Elsevier Ltd. All rights reserved.