5-(tert-butyldimethylsilanyloxymethyl)-3-(5-nitropyridin-2-yl)-5-phenylimidazolidine-2,4-dione | 1401226-51-4

• 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: 5-(tert-butyldimethylsilanyloxymethyl)-3-(5-nitropyridin-2-yl)-5-phenylimidazolidine-2,4-dione
• CAS: 1401226-51-4
• 化学式: C₂₁H₂₆N₄O₅Si
• 分子量: 442.547
• InChiKey: HSAALIPNYJTEAT-UHFFFAOYSA-N

物化性质

• 密度：
  1.219±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  114.67
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilanyloxymethyl)-3-(5-nitropyridin-2-yl)-5-phenylimidazolidine-2,4-dione 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 5-hydroxymethyl-1-methyl-3-(5-nitropyridin-2-yl)-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
• 作为产物：
  描述：

  2-溴-5-硝基吡啶 、 5-(tert-butyldimethylsilanyloxymethyl)-5-phenylimidazolidine-2,4-dione 在 copper(I) oxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.17h， 以31%的产率得到5-(tert-butyldimethylsilanyloxymethyl)-3-(5-nitropyridin-2-yl)-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