3,6-Dimethyl-2-(5-trifluoromethyl-1H-benzoimidazole-2-sulfinylmethyl)-phenylamine | 106747-32-4

• 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-trifluoromethyl-1H-benzoimidazole-2-sulfinylmethyl)-phenylamine
• 英文别名: 3,6-dimethyl-2-[[6-(trifluoromethyl)-1H-benzimidazol-2-yl]sulfinylmethyl]aniline
• CAS: 106747-32-4
• 化学式: C₁₇H₁₆F₃N₃OS
• 分子量: 367.395
• InChiKey: KSVYVVBXEROINW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-三氟甲基-1H-苯并[d]咪唑-2-硫醇 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.5h， 生成 3,6-Dimethyl-2-(5-trifluoromethyl-1H-benzoimidazole-2-sulfinylmethyl)-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

文献信息

• 2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-benzenamines
  申请人：G.D. Searle & Co.

  公开号：EP0204215A1

  公开（公告）日：1986-12-10

  This invention relates to 2-[(1H-benzimidazol-2- ylsulfinyllmethyl]benzenamines of the formula wherein R' is hydrogen, alkyl, alkoxy, halogen or fluorinated alkyl; R2 is hydrogen, alkyl, alkoxy, fluorinated alkyl or alkoxycarbonyl; R3, R4, R6 and R6 are hydrogen, alkyl, alkoxy, halogen, fluorinated alkyl or alkoxycarbonyl; R7 is hydrogen, alkyl or alkanoyl; and R6 is hydrogen or alkyl. The compounds are useful in the treatment and prevention of ulcers.

  本发明涉及式中的 2-[(1H-苯并咪唑-2-亚磺酰甲基]苯胺，其中 R' 是氢、烷基、烷氧基、卤素或氟化烷基；R2 是氢、烷基、烷氧基、氟化烷基或烷氧基羰基；R3、R4、R6 和 R6 是氢、烷基、烷氧基、卤素、氟化烷基或烷氧基羰基；R7 是氢、烷基或烷酰基；R6 是氢或烷基。 这些化合物可用于治疗和预防溃疡。
• ADELSTEIN, GILBERT W.;YEN, CHUNG H.;HAACK, RICHARD A.;YU, STELLA;GULLIKSO+, J. MED. CHEM., 31,(1988) N 6, 1215-1220
  作者：ADELSTEIN, GILBERT W.、YEN, CHUNG H.、HAACK, RICHARD A.、YU, STELLA、GULLIKSO+

  DOI：——

  日期：——
• Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase
  作者：Gilbert W. Adelstein、Chung H. Yen、Richard A. Haack、Stella Yu、Gary Gullikson、Doreen V. Price、Charles Anglin、Dennis L. Decktor、Henry Tsai、Robert H. Keith

  DOI：10.1021/jm00401a024

  日期：1988.6

  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.