Gastric antisecretory 9H-xanthen-9-amines

A series of 9H-xanthen-9-amines possessing a wide variety of nitrogen substituents at C-9 was prepared for evaluation of gastric antisecretory activity. These substituents included the acetamidine, imidate, pyrimidine, thiazoline, quinuclidine, 2-hydrazinopyridine, aminopiperidine, aminoalkylimidazo...

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Bibliographic Details
Published in:	Journal of medicinal chemistry Vol. 26; no. 9; pp. 1218 - 1223
Main Authors:	Bender, Paul E, Perchonock, Carl D, Groves, William G, Smith, Robert C, Stringer, Orum D, Sneed, Rayvon, Schlosser, Jack H, Hostelley, Linda S, Hwang, Bruce Y. H
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 01-09-1983
Subjects:	Animals Dogs Gastric Acid - metabolism Half-Life Male Pentagastrin - pharmacology Rats Xanthenes - chemical synthesis Xanthenes - pharmacology
Online Access:	Get full text
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Summary:	A series of 9H-xanthen-9-amines possessing a wide variety of nitrogen substituents at C-9 was prepared for evaluation of gastric antisecretory activity. These substituents included the acetamidine, imidate, pyrimidine, thiazoline, quinuclidine, 2-hydrazinopyridine, aminopiperidine, aminoalkylimidazole, and aminoalkylpyridine moieties. The majority of compounds in this series inhibited gastric acid secretion when tested orally in the pylorus-ligated rat. Potency was increased by intraduodenal administration and diminished by incubation with gastric juice, suggesting partial degradation of the compounds in the gastric environment. A representative example, 3-(9H-xanthen-9-ylamino)-1-ethylpiperidine, exhibited similar activity in dogs, although no free compound could be detected in the blood. It is therefore hypothesized that this compound is either rapidly bound to tissue and/or metabolized to an active species.
Bibliography:	istex:E61943BECC1628BF820785E75D1E7030E2106EBE ark:/67375/TPS-D06XLZWP-2 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00363a003