1-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]ethanone | 1401224-73-4

• 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: 1-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]ethanone
• CAS: 1401224-73-4
• 化学式: C₁₅H₂₂N₂O₂Si
• 分子量: 290.437
• InChiKey: VXLHQKXVYZHKSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 ammonium carbonate monohydrate 、 1-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]ethanone 在 水 作用下， 以 乙醇 为溶剂， 反应 93.0h， 生成 5-methyl-5-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]imidazolidine-2,4-dione
  参考文献：
  名称：

  Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator

  摘要：

  Structural modification performed on a 4-methyl-4-(4-hydroxyphenyphyl)hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. This led to the identification of (S)-(-)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile ((S)-(-)-18a, GLPG0492) evaluated in vivo in a classical model of orchidectomized rat. In this model, (-)-18a exhibited anabolic activity on muscle, strongly dissociated from the androgenic activity on prostate after oral dosing. (-)-18a has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm300281x
• 作为产物：
  描述：

  1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazole-5-carboxylic acid methoxy methyl amide 、 甲基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 1-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]ethanone
  参考文献：
  名称：

  Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator

  摘要：

  Structural modification performed on a 4-methyl-4-(4-hydroxyphenyphyl)hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. This led to the identification of (S)-(-)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile ((S)-(-)-18a, GLPG0492) evaluated in vivo in a classical model of orchidectomized rat. In this model, (-)-18a exhibited anabolic activity on muscle, strongly dissociated from the androgenic activity on prostate after oral dosing. (-)-18a has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm300281x