4-{4-methyl-2,5-dioxo-4-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]imidazolidin-1-yl}-2-(trifluoromethyl)benzonitrile | 1401224-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-{4-methyl-2,5-dioxo-4-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]imidazolidin-1-yl}-2-(trifluoromethyl)benzonitrile
• 英文别名: 4-[4-Methyl-2,5-dioxo-4-[1-(2-trimethylsilylethoxymethyl)benzimidazol-5-yl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
• CAS: 1401224-91-6
• 化学式: C₂₅H₂₆F₃N₅O₃Si
• 分子量: 529.594
• InChiKey: XLYNMOYBEKPECV-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-{4-methyl-2,5-dioxo-4-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]imidazolidin-1-yl}-2-(trifluoromethyl)benzonitrile 、 碘甲烷 在 sodium hydride 、 盐酸 作用下， 以 N,N-二甲基乙酰胺 、 mineral oil 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 24.0h， 以0.33 g的产率得到4-[4-(1H-benzoimidazol-5-yl)-3,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
  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：

  4-溴-2-(三氟甲基)苯甲腈 、 5-methyl-5-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]imidazolidine-2,4-dione 在 copper(I) oxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以0.37 g的产率得到4-{4-methyl-2,5-dioxo-4-[1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazol-5-yl]imidazolidin-1-yl}-2-(trifluoromethyl)benzonitrile
  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