![]() This protonation results in reaction of the C-2 with the unprotonated fraction of the pyridine ring to form the reactive derivatives. However, the data obtained here show that their conversion to the reactive cationic thiophilic sulfenic acid or sulfenamide depends mainly not on pyridine protonation but on a second protonation of the imidazole component that increases the electrophilicity of the C-2 position on the imidazole. This unique acid-catalysis mechanism had been ascribed to the nucleophilicity of the pyridine ring. They are all prodrugs that inhibit the acid-secreting gastric (H +, K +)-ATPase by acid activation to reactive thiophiles that form disulfide bonds with one or more cysteines accessible from the exoplasmic surface of the enzyme. Proton pump inhibitors (PPIs), drugs that are widely used for treatment of acid related diseases, are either substituted pyridylmethylsulfinyl benzimidazole or imidazopyridine derivatives.
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