4-(3-benzyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(trifluoromethyl)benzonitrile | 1363401-30-2

• 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-(3-benzyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(trifluoromethyl)benzonitrile
• 英文别名: 4-(3-Benzyl-2-oxobenzimidazol-1-yl)-2-(trifluoromethyl)benzonitrile
• CAS: 1363401-30-2
• 化学式: C₂₂H₁₄F₃N₃O
• 分子量: 393.368
• InChiKey: HWNIORKTZJWAAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟-2-(三氟甲基)苯甲腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 169.0h， 生成 4-(3-benzyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  Design of oxobenzimidazoles and oxindoles as novel androgen receptor antagonists

  摘要：

  Oxobenzimidazoles (e.g., 1), a novel series of androgen receptor (AR) antagonists, were discovered through de novo design guided by structure-based drug design. The compounds in this series were reasonably permeable and metabolically stable, but suffered from poor solubility. The incorporation of three dimensional structural features led to improved solubility. In addition, the observation of a 'flipped' binding mode of an oxobenzimidazole analog in an AR ligand binding domain (LBD) model, led to the design and discovery of the novel oxindole series (e.g., 2) that is a potent full antagonist of AR.[GRAPHICS]. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.116

文献信息

• Design of oxobenzimidazoles and oxindoles as novel androgen receptor antagonists
  作者：Chuangxing Guo、Mason Pairish、Angelica Linton、Susan Kephart、Martha Ornelas、Asako Nagata、Benjamin Burke、Liming Dong、Jon Engebretsen、Andrea N. Fanjul

  DOI：10.1016/j.bmcl.2012.01.116

  日期：2012.4

  Oxobenzimidazoles (e.g., 1), a novel series of androgen receptor (AR) antagonists, were discovered through de novo design guided by structure-based drug design. The compounds in this series were reasonably permeable and metabolically stable, but suffered from poor solubility. The incorporation of three dimensional structural features led to improved solubility. In addition, the observation of a 'flipped' binding mode of an oxobenzimidazole analog in an AR ligand binding domain (LBD) model, led to the design and discovery of the novel oxindole series (e.g., 2) that is a potent full antagonist of AR.[GRAPHICS]. (C) 2012 Elsevier Ltd. All rights reserved.