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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

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

H Terauchi, A Tanitame, K Tada, K Nakamura, Y Seto, Y Nishikawa

J Med Chem. 1997 Jan 31;40(3):313-21.

PMID: 9022797

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP102625649	Pantoprazole Related Compound B	102625-64-9	Price
AP103577408	Lansoprazole Related Compound B	103577-40-8	Price
AP127780169	Pantoprazole Related Compound A	127780-16-9	Price

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