3,6-Dimethyl-2-(5-methyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phenylamine | 106746-94-5

• 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: 3,6-Dimethyl-2-(5-methyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phenylamine
• CAS: 106746-94-5
• 化学式: C₁₇H₁₉N₃S
• 分子量: 297.424
• InChiKey: HMJVDXHSYWOFLV-UHFFFAOYSA-N

物化性质

• 沸点：
  539.4±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54.7
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,6-Dimethyl-2-(5-methyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phenylamine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以16%的产率得到2-[[(5-methyl-1H-benzimidazol-2-yl)sulfinyl]-methyl]-5,6-dimethylbenzenamine
  参考文献：
  名称：

  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase

  摘要：

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.

  DOI：

  10.1021/jm00401a024
• 作为产物：
  描述：

  2-(Chloromethyl)-3,6-dimethylaniline 、 2-巯基-5-甲基苯并咪唑 以 乙醇 为溶剂， 反应 2.0h， 以73%的产率得到3,6-Dimethyl-2-(5-methyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phenylamine
  参考文献：
  名称：

  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase

  摘要：

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.

  DOI：

  10.1021/jm00401a024