2-(5,6-Dimethoxy-1H-benzoimidazole-2-sulfinylmethyl)-phenylamine | 106747-37-9

• 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: 2-(5,6-Dimethoxy-1H-benzoimidazole-2-sulfinylmethyl)-phenylamine
• 英文别名: 2-[(5,6-dimethoxy-1H-benzimidazol-2-yl)sulfinylmethyl]aniline
• CAS: 106747-37-9
• 化学式: C₁₆H₁₇N₃O₃S
• 分子量: 331.395
• InChiKey: CUKRMXRKRYEOFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,6-dimethoxy-1,3-dihydrobenzimidazole-2-thione 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 2-(5,6-Dimethoxy-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

• 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：——
• LANG, HANS-JOCHEN;RACKUR, GERHARD;ROSNER, MANFRED;HERLING, ANDREAS W.
  作者：LANG, HANS-JOCHEN、RACKUR, GERHARD、ROSNER, MANFRED、HERLING, ANDREAS W.

  DOI：——

  日期：——
• ——
  作者：LANG H. -J.、 RACKUR G.、 ROSNER M.、 HERLING A.

  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.