3,6-Dimethyl-2-(5-trifluoromethyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phenylamine | 106746-95-6

• 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: 3,6-Dimethyl-2-(5-trifluoromethyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phenylamine
• 英文别名: 3,6-dimethyl-2-[[6-(trifluoromethyl)-1H-benzimidazol-2-yl]sulfanylmethyl]aniline
• CAS: 106746-95-6
• 化学式: C₁₇H₁₆F₃N₃S
• 分子量: 351.395
• InChiKey: NTQVQRDSSVFQOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 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：
  80
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-Dimethyl-2-(5-trifluoromethyl-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21%的产率得到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
• 作为产物：
  描述：

  5-三氟甲基-1H-苯并[d]咪唑-2-硫醇 、 2-(Chloromethyl)-3,6-dimethylaniline 以 乙醇 为溶剂， 反应 2.0h， 以69%的产率得到3,6-Dimethyl-2-(5-trifluoromethyl-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

文献信息

• Method of using (H+/K+) ATPase inhibitors as antiviral agents
  申请人：——

  公开号：US20010047038A1

  公开（公告）日：2001-11-29

  A class of compounds which are (H + /K + )ATPase inhibitors can be used for the treatment of viral infections. Compounds of particular interest are defined by Formula III: 1 wherein D is N or CH; wherein R 7 is one or more radicals selected from hydrido, alkoxy, amino, cyano, nitro, hydroxyl, alkyl, halo, haloalkyl, carboxyl, alkanoyl, nitro, amino, alkylamino, amide, alkylamide, alkoxycarbonyl, alkylthio, alkylsulfinyl and alkylsulfonyl; wherein R 9 is one or more radicals selected from hydrido, alkoxy, amino, alkyl, halo, cyano, nitro, hydroxyl, haloalkyl, carboxyl, alkanoyl, nitro, amine, alkylamine, dialkylamine, amide, alkylamide, alkoxycarbonyl, alkylthio, alkylsulfinyl and alkylsulfonyl; and wherein R 10 and R 11 are independently selected from hydrido and alkyl; or a pharmaceutically acceptable salt thereof.

  一类(H+/K+)ATP酶抑制剂类化合物可用于治疗病毒感染。特别感兴趣的化合物由公式III:1定义，其中D为N或CH; R7为一个或多个基团，选自氢，烷氧基，氨基，氰基，硝基，羟基，烷基，卤素基，卤代烷基，羧基，烷酰基，硝基，氨基，烷基氨基，酰胺，烷基酰胺，烷氧羰基，烷基硫醇基，烷基亚砜基和烷基磺酰基; R9为一个或多个基团，选自氢，烷氧基，氨基，烷基，卤素基，氰基，硝基，羟基，卤代烷基，羧基，烷酰基，硝基，胺基，烷基胺基，二烷基胺基，酰胺，烷基酰胺，烷氧羰基，烷基硫醇基，烷基亚砜基和烷基磺酰基; R10和R11独立选择自氢和烷基; 或其药学上可接受的盐。
• 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：——
• US6906078B2
  申请人：——

  公开号：US6906078B2

  公开（公告）日：2005-06-14
• 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.