(4-Bromo-phenyl)-[6-methoxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzoimidazol-5-yl]-methanone | 724768-06-3

• 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-Bromo-phenyl)-[6-methoxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzoimidazol-5-yl]-methanone
• CAS: 724768-06-3
• 化学式: C₂₂H₂₇BrN₂O₃Si
• 分子量: 475.457
• InChiKey: AOLGJTRKRGRPDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4-Bromo-phenyl)-[6-methoxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzoimidazol-5-yl]-methanone 在 盐酸 、 palladium diacetate 、 caesium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.33h， 生成 [4-(2,4-Difluoro-phenylamino)-phenyl]-(6-methoxy-2-methyl-3H-benzoimidazol-5-yl)-methanone
  参考文献：
  名称：

  SAR of benzoylpyridines and benzophenones as p38α MAP kinase inhibitors with oral activity

  摘要：

  Benzoylpyridines and benzophenones were synthesized and evaluated in vitro as p38alpha inhibitors and in vivo in several models of rheumatoid arthritis. Oral activity was found to depend upon substitution: 1,1-dimethylpropynylamine substituted benzophenone 10b (IC50: 14 nM) and pyridinoyl substituted benzimidazole 17b (IC50: 21 nM) showed highest efficacy and selectivity with ED50S of 9.5 and 8.6 mg/kg po in CIA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.111
• 作为产物：
  描述：

  1,4-二溴苯 在 manganese(IV) oxide 、 正丁基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.58h， 生成 (4-Bromo-phenyl)-[6-methoxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzoimidazol-5-yl]-methanone
  参考文献：
  名称：

  SAR of benzoylpyridines and benzophenones as p38α MAP kinase inhibitors with oral activity

  摘要：

  Benzoylpyridines and benzophenones were synthesized and evaluated in vitro as p38alpha inhibitors and in vivo in several models of rheumatoid arthritis. Oral activity was found to depend upon substitution: 1,1-dimethylpropynylamine substituted benzophenone 10b (IC50: 14 nM) and pyridinoyl substituted benzimidazole 17b (IC50: 21 nM) showed highest efficacy and selectivity with ED50S of 9.5 and 8.6 mg/kg po in CIA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.111