4-[1-(4-cyano-3-methoxyphenyl)-3,3-dimethyl-2-oxoindol-5-yl]-2-fluoro-N-methylbenzamide | 1363401-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[1-(4-cyano-3-methoxyphenyl)-3,3-dimethyl-2-oxoindol-5-yl]-2-fluoro-N-methylbenzamide
• CAS: 1363401-55-1
• 化学式: C₂₆H₂₂FN₃O₃
• 分子量: 443.477
• InChiKey: HGIKJIYTWFZEGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴-2-甲氧基苯腈 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 copper(l) iodide 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 溴 、 sodium acetate 、 cesium fluoride 作用下， 以 水 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.67h， 生成 4-[1-(4-cyano-3-methoxyphenyl)-3,3-dimethyl-2-oxoindol-5-yl]-2-fluoro-N-methylbenzamide
  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