Journal of Medicinal Chemistry p. 1215 - 1220 (1988)
Update date:2022-08-03
Topics:
Adelstein, Gilbert W.
Yen, Chung H.
Haack, Richard A.
Yu, Stella
Gullikson, Gary
et al.
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 unubstituted 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.
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