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Synthesis and antiulcer activity of 4-substituted 8-[(2-benzimidazolyl)sulfinylmethyl]-1,2,3,4-tetrahydroquinoli nes and related compounds.

Abstract
A series of 4-substituted 8-[(2-benzimidazolyl)sulfinylmethyl]-1,2,3,4-tetrahydroquinolin es was synthesized and examined for their (H+ + K+)adenosine triphosphatase (ATPase)-inhibitory and antisecretory activities against histamine-induced gastric acid secretion in rats. Many compounds tested were potent inhibitors of (H+ + K+)ATPase. Most compounds showed antisecretory activity. The antiulcer activity against water-immersion stress-induced gastric ulcer, aspirin-induced gastric ulcer and gastric necrosis induced by hydrochloric acid also were tested in the rat. Some of these compounds, in particular, 4-(N-allyl-N-methylamino)-1-ethyl-8-[(5-fluoro-6-methoxy-2-benzimidazoly l) sulfinylmethyl]-1-ethyl-1,2,3,4-tetrahydroquinoline (XVIIx) were found to have potent activity. The structure-activity relationships are discussed.
AuthorsM Uchida, M Chihiro, S Morita, H Yamashita, K Yamasaki, T Kanbe, Y Yabuuchi, K Nakagawa
JournalChemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 38 Issue 6 Pg. 1575-86 (Jun 1990) ISSN: 0009-2363 [Print] Japan
PMID2170036 (Publication Type: Journal Article)
Chemical References
  • Anti-Ulcer Agents
  • Benzimidazoles
  • Quinolines
  • Sulfides
  • Adenosine Triphosphatases
  • H(+)-K(+)-Exchanging ATPase
Topics
  • Adenosine Triphosphatases (antagonists & inhibitors)
  • Animals
  • Anti-Ulcer Agents (chemical synthesis)
  • Benzimidazoles (chemical synthesis, pharmacology)
  • Chemical Phenomena
  • Chemistry
  • H(+)-K(+)-Exchanging ATPase
  • Male
  • Quinolines (chemical synthesis, pharmacology)
  • Rats
  • Rats, Inbred Strains
  • Sulfides (chemical synthesis, pharmacology)

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