3-(2-trimethylsilylethoxymethyl)benzimidazole-5-carboxylic acid | 1401225-22-6

• 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: 3-(2-trimethylsilylethoxymethyl)benzimidazole-5-carboxylic acid
• CAS: 1401225-22-6
• 化学式: C₁₄H₂₀N₂O₃Si
• 分子量: 292.41
• InChiKey: IJDOGZKBELAJIR-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±53.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 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：
  0.43
• 拓扑面积：
  64.35
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(三甲基硅烷基)乙氧甲基氯 、 苯并咪唑-5-羧酸甲酯 在 sodium hydride 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 甲醇 为溶剂， 反应 18.5h， 生成 1-(2-(trimethylsilanyl)ethoxymethyl)-1H-benzoimidazole-5-carboxylic acid 、 3-(2-trimethylsilylethoxymethyl)benzimidazole-5-carboxylic acid
  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