Studies on proton pump inhibitors. II. Synthesis and antiulcer activity of 8-((2-benzimidazolyl)-sulfinylmethyl)-1,2,3,4-tetrahydroquinolines and related compounds.

Abstract

Many 8-[(2-benzimidazolyl)sulfinylmethyl]-1,2,3,4-tetrahydroquinolin e derivatives were synthesized and tested for their (H+ + K+)adenosine triphosphatase (ATPase)-inhibitory and antisecretory activities against histamine-induced gastric acid secretion in rats. These sulfinyl compounds were synthesized by the oxidation of the corresponding sulfides, which were obtained from the reaction of 8-chloromethyl-1,2,3,4-tetrahydroquinolines and 2-mercaptobenzimidazoles in the presence of potassium carbonate. All compounds tested were potent inhibitors of (H+ + K+)ATPase. Most of the compounds showed antisecretory activity. Among them, 8-[(2-benzimidazolyl)sulfinylmethyl]-1-ethyl-1,2,3,4-tetrahydro quinoline (IXa) was found to have the most potent activity. The structure-activity relationships are discussed.

Solvent Dependent Regioselective Hydrogenation of Substituted Quinolines

“…This product is known to be difficult to reduce. 18 Moreover, it was the first time we obtained such an isomer. This reactivity is notable as, usually, the same acidic conditions are required to obtain either 5,6,7,8-tetrahydro or decahydro derivatives.…”

4-[1-(Phenylsulfonyl)indol-3-yl]-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline

“…exhibit antitumour activities (Jaton et al, 1997) and also act as potent antipsychotic agents (Norman et al, 1996), and a compound containing the tetrahydroquinoline moiety acts as an antischistosomal drug (Billings & Heidelberger, 1982). They also possess anti-in¯ammatory (Ohnishi et al, 1981), antiamúbic (Bailey et al, 1979), antiulcer (Uchida et al, 1989) and analgesic (Shaaban et al, 1977) activities. In order to obtain detailed information on molecular conformation, the X-ray structure determination of the title compound, (I), has been carried out and the results are presented here.…”

Quinolines, Isoquinolines, Angustureine, and Congeneric Alkaloids — Occurrence, Chemistry, and Biological Activity

“…1,2,3,4-Tetrahydroquinoline-4-carboxylic acid is used in tissue-irrigating solutions [18]. A wide array of other biological activities have been reported, including inter alia inhibition of (H + /K + )-ATPase [19], blood serum monoamine oxidase [20], angiotensin I converting enzyme [21], lipoxygenase [22], lipid peroxidation [23], bone resorption [24], leukotriene synthesis [25,26], and bacterial dihydrofolate reductase [27]. Relevance to many other indications has also been noted .…”