4-Substituted 1-(2-methylphenyl)thieno[2,3-c]-1,5-naphthyridines as possible reversible inhibitors of gastric M+,K+-ATPase

Article abstract of DOI:10.1016/0223-5234(96)89168-9

Seven 1-(2-methylphenyl)thieno[2,3-c]-1,5-naphthyridines substituted in the 4-position with different amino-containing groups have been prepared. The reaction route to these compounds consisted of a palladium(0)-catalyzed cross-coupling between 1-bromothieno[2,3-c]-1,5-naphthyridine and 2-methyl-1-trimethylstannylbenzene, then oxidation of the 5-nitrogen, followed by treatment with thionyl chloride to give the 4-chloro derivative. The compounds obtained after nucleophilic substitution were tested with regard to their effects on H⁺,K⁺-ATPase activity and on acid formation in gastric glands. However, the inhibitory potency in vitro of the substituted naphthyridines was not high enough to be of interest from a pharmacological point of view.