181822-32-2

Upstream product

• 504-24-5 4-aminopyridine 
• 181823-27-8 2-(2,4-Dimethoxy-benzylsulfanyl)-nicotinic acid 
• 38521-46-9 3-carboxy-2-mercaptopyridine 
• 7314-44-5 2,4-dimethoxylbenzyl alcohol 

Downstream Products

• 181820-89-3 2-(2,4-Dimethoxy-phenylmethanesulfinyl)-N-pyridin-4-yl-nicotinamide 

Relevant academic research and scientific papers

Nicotinamide derivatives as a new class of gastric H+/K+-ATPase inhibitors. 1. Synthesis and structure-activity relationships of N- substituted 2-(benzhydryl- and benzylsulfinyl)nicotinamides

A new series of N-Substituted 2-(benzhydryl- and benzylsulfinyl)nicotinamides 7 and 8 were synthesized. Upon acid activation in the acidic environment of the parietal cell, these compounds are converted into their active forms, 2,3-dihydro-3-oxoisothiazolo[5,4-b]pyridines 5, which inhibit gastric H+/K+-ATPase. Inhibitory activities against [14C]aminopyrine accumulation stimulated by dibutyryl cAMP in isolated rabbit parietal cells in vitro and histamine-induced gastric acid secretion in pylorus-ligated rats by intraduodenal administration in vivo were evaluated, and the structure-activity relationships were examined. Among the compounds synthesized, 2-[(2,4-dimethoxybenzyl)sulfinyl]-N-(4- pyridyl)nicotinamide (8b) showed potent inhibitory activities in vitro and in vivo equivalent to those of omeprazole, a typical H+/K+-ATPase inhibitor. Moreover, 8b was much more stable at neutral and weakly acidic pH than omeprazole, lansoprazole, and pantoprazole. Compound 8b is considered to be a promising agent for treating acid-related gastrointestinal disorders.

A convenient synthesis of n-substituted 2,3-dihydro-3-oxoisothiazolo[5,4-b]pyridines in acidic conditions

A novel and convenient synthesis of N-substituted 2,3-dihydro-3-oxoisothiazolo[5,4-b]pyridines which possess potent in vitro inhibitory activity against gastric (H+/K+)-ATPase is reported. Compared with the methods reported previously, the compounds were synthesized more readily in relatively high yields by conversion of N-substituted 2-(benzyl-, 1-phenylethyl-, and benzhydrylsulfinyl)nicotinamides (17d-l) in a diluted hydrochloric acid-methanol solution at room temperature.