Ife, Robert J. published the artcile2-[[(4-Amino-2-pyridyl)methyl]sulfinyl]benzimidazole H+/K+-ATPase inhibitors. The relationship between pyridine basicity, stability, and activity, Safety of 4-Amino-2-picoline, the publication is Journal of Medicinal Chemistry (1989), 32(8), 1970-7, database is CAplus and MEDLINE.
The benzimidazole sulfoxide class of antisecretory H+/K+-ATPase inhibitors need to possess high stability under neutral physiol. conditions yet rearrange rapidly at low pH to the active sulfenamide. Since the initial reaction involves internal nucleophilic attack by the pyridine nitrogen, control of the pyridine pKa is critical By utilizing the powerful electron-donating effect of a 4-amino substituent on the pyridine, moderated by the electron-withdrawing effect of a 3- or 5-halogen substituent, a combination of high potency (as inhibitors of histamine-stimulated gastric acid secretion) and good stability under physiol. conditions can be obtained in the title compounds I (NR2 = morpholino, NMe2, etc.; R1 = H, halo, Me; R2 = H, halo). Furthermore, the role of the steric interaction between the 3/5-substituents and the 4-substituent in modifying the electron-donating ability of the 4-amino group is exemplified, and addnl. factors affecting stability are identified. One compound, in particular, 2-[[(3-chloro-4-morpholino-2-pyridyl)methyl]sulfinyl]-5-methoxy-(1H)-benzimidazole was chosen for further development and evaluation in man. I were prepared by reaction of aminopyridines II with 5-methoxy-2-mercaptobenzimidazole, followed by oxidation
Journal of Medicinal Chemistry published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Safety of 4-Amino-2-picoline.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem