5-(tert-butyldimethylsilanyloxymethyl)-5-phenylimidazolidine-2,4-dione | 1401226-49-0

• 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: 5-(tert-butyldimethylsilanyloxymethyl)-5-phenylimidazolidine-2,4-dione
• 英文别名: 5-(((Tert-butyldimethylsilyl)oxy)methyl)-5-phenylimidazolidine-2,4-dione；5-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenylimidazolidine-2,4-dione
• CAS: 1401226-49-0
• 化学式: C₁₆H₂₄N₂O₃Si
• 分子量: 320.464
• InChiKey: GQLLPPAGTKNKLY-UHFFFAOYSA-N

物化性质

• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilanyloxymethyl)-5-phenylimidazolidine-2,4-dione 在 copper(I) oxide 、 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.83h， 生成 5-(4-hydroxymethyl-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)thiophene-2-carbonitrile
  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：

  potassium cyanide 、 ammonium carbonate monohydrate 、 乙酮,2-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-1-苯基- 在 水 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以100%的产率得到5-(tert-butyldimethylsilanyloxymethyl)-5-phenylimidazolidine-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