2-[[(4-Amino-2-pyridyl) methyl] sulfinyl] benzimidazole H+/K+-ATPase inhibitors. The relationship between pyridine basicity, stability, and activity

…, CA Price, CJ Theobald, AH Underwood

文献索引：Ife; Dyke; Keeling; Meenan; Meeson; Parsons; Price; Theobald; Underwood Journal of Medicinal Chemistry, 1989 , vol. 32, # 8 p. 1970 - 1977

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被引用次数: 46

摘要

The benzimidazole sulfoxide class of antisecretory Ht/Kt-ATPase inhibitors need to possess high stability under neutral physiological conditions yet rearrange rapidly at low pH to the active sulfenamide 2. Since the initial reaction involves internal nucleophilic attack by the pyridine nitrogen, control of the pyridine pK, is critical. In this paper we show that by utilizing the powerful electron-donating effect of a 4-amino substituent on the pyridine, moderated ...