166390-96-1Relevant academic research and scientific papers
2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors
Yamada,Yura,Morimoto,Harada,Yamada,Honma,Kinoshita,Sugiura
, p. 596 - 604 (2007/10/03)
Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.
A novel synthesis of methyl 1,5-disubstituted imidazole-4-carboxylates using 3-bromo-2-isocyanoacrylates
Nunami,Yamada,Fukui,Matsumoto
, p. 7635 - 7642 (2007/10/02)
Methyl 1,5-disubstituted imidazole-4-carboxylates 1 were synthesized using methyl 3-substituted 3-bromo-2-isocyanoacrylates 3 (BICA), and the reaction mechanism was elucidated. Reactions of 3, which were prepared by bromination of 3-substituted 2-(formyla
