YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of N-[2-(3,5-dimethyl-4-methoxypyridyl)alkyl]oxazolidinone Analogues and Evaluation of their Proton Pump Enzyme Inhibitions

N-[2-(3,5-디메틸-4-메톡시피리딜)알킬]옥사졸리디논 유도체의 합성 및 프로톤 펌프 효소 저해 효과

  • 윤성화 (아주대학교 공업화학과) ;
  • 김도영 (아주대학교 공업화학과) ;
  • 황성관 (아주대학교 공업화학과)
  • Published : 1997.04.01
Download PDF
⟨ Previous Next ⟩

Abstract

Four oxazolidinone analogues(6, 7, 8, 9), which are isosters of 5, were synthesized by the reaction of 2-chloroalkyl-3,5-dimethyl-4-methoxypyridine with the corresponding benzox azolidinone or oxazolidinone, respectively, and were evaluated for their inhibitory activities toward proton pump enzyme under in vitro condition. Isosteric substitution of the benzothiazolidine moiety in 5 with benzoxazolidinone rendered the molecule relatively inactive.

Keywords

References

  1. Drug News Prospect v.1 no.1 The year's new drugs Prous, J. R.
  2. Progress in Medicinal Chemistry v.31 Gastric $H^+$/$K^+$-ATPase inhibitors General review by andres, W.;Herling, D. V. M.;Klaus, W.
  3. Eur. J. Clin. Invest. v.20 no.Sup. 1 Proposed mechanism of introduction of gastric carcinoids: The gastric hypothesis Hakanson, R.;Sundler, F.
  4. Digestion v.35 no.Sup.1 Effect of short-and long-term feeding of omeprazole on rat gastric endocrine cells Creutzfeldt, W.;Stockmann, F.;Conon, J. M.;Folsch, U. R.;bonatz, G.;Wulfrath, M.
  5. J. Chem. Soc. chem. Commun. v.125 Acid activation of ($H^+$/$K^+$)-AT-Pase inhibiting 2-[(2-pyridylmethyl)sulfinyl]-benzimidazoles : Isolation and characterization of the thiophilic 'active principle' and its reaction Figala, V.;Klemm, K.;Kohl, B.;Kruger, U.;Rainer, G.;Schaefer, H.;Senn-Bilfinger, J.;Strurm, E.
  6. J. Org. Chem. v.52 ($H^+$/$K^+$)-ATPase inhibiting 2-[(2-pyridyl-methyl)sulfinyl]benzimidazoles, 1.: Their Reaction with thiols under acidic conditions. Disulfide containing 2-pyridiniobenzimidazolides ans mimics for the inhibited enzyme Sturm. E.;Kruger, U.;Senn-Bilfinger, J.;Figala, V.;Klemm, K.;Kohl, B.;Rainer, G.;Scharfer, H.
  7. J. Org. Chem. v.52 ($H^+$/$K^+$)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl] benzimidazoles. 2. : The reaction cascade induced by treatment with acids. Formation of 5H-pyridyl[1' 2',4,5][1,2,4]thiadiazino-[2,3a]benzimidazol-13-ium salts and their reactions with thiols Senn-Bilfinger, J.;Kruger, U.;Sturm, E.;Figala, V.;Klemm, K.;Kohl, B.;Rainer, G.;Schaefer, H.;Huttner, G.;Zsolnai,L.
  8. J. Org. Chem. v.55 ($H^+$/$K^+$)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl] benzimidazoles. 3. : Evidence for the involvement of a sulfenic acid in their reactions kruger, U.;Senn-Bilfinger, J.;Sturm, E.;Figala,V.;Klemm, K.;Kohl, B.;Rainer, G.;Schaefer, H.;Blake, T. J.;Darkin, D. W.;Ife, R. J.;Leach, C. A.;Mitchell, R. C.;Pepper, E. S.;Salter, C. J.;Viney, N. J.
  9. J. Med. Chem. v.35 ($H^+$/$K^+$)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl] benzimidazoles. 4. : A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity. The selectionof pantoprazole as a clinical candidate Kohl, B.;Sturm, E.;Senn-Bilfinger, J.;alexander Simon, W.;Kruger, U.;Schaefer, H.;Rainer, G.;Figala, V.;Klemm, K.;Ife, R. J.;Leach, C. A.
  10. Chem. Phar. bull. v.39 Synthesis and structure-activity relationships of N-substituted 2-[(2-imidazoylsul-fyril)methyl]aniline as a new class of ($H^+$/$K^+$)-ATPase inhibitors Yamakawa, T.;Matsukura, H.;Nomura,Y.;Yoshioka, M.;Massaki, M.;Igata, H.;Okabe, S.
  11. J. Med. Chem. v.39 2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6,-tetrahydrocyclopent[d]imidazole as a novel class of gastric ($H^+$/$K^+$)-AT-Pase inhibitors Massaki, Y.;Takeshi, Y.;Mashamichi, M.;Tsunehiro,H.;Koichiro, Y.;Yasushi,H.;Mine, K.;Massaki,S.
  12. Syntheses and biological evaluations of 2-(3,5-dimethyl-4-methoxypyridyl) benzo-thiazolidines as a novel class of gastric $H^+$/$K^+$-ATPase inhibitors Yoon, S. H.;Seo, s.;Lee, Y.;Hwang, S.
  13. National academy of science-national research council Influence of isosteric replacement upon biological activity. Symposium on chemical-biological corelation Fridmann, H. L.
  14. Japan J. Pharmacol. v.40 Biochemical and pharmacological analysis of 2-[(2-dimethylaminobenzy)sulfinyl] benzimidazole(NC-1300) Okabe, S.;Higaki, E.;Higuchi, T.;Sato, M.;Hara, K.
  15. Biochem. Biophys. Acta v.465 Characterization of gastric mucosal membrane. Ⅸ. Fractionation and purification of $H^+$/$K^+$-ATPase contraining vesicles by zone centrifugation and free-flow electrophoresis technique Lewin, M.;Sachs, G.
  16. Anal. Biochem. v.9 A micro-biuret method for estimating proteins Itzhaki, R. F.;Gill, D. M.
  17. J. Biol. Chem v.202 A microco-lorimetric method for the determination of phos-phorous Taussky, H. H.;Shorr, E.