Studies on antipeptic ulcer agents: a structure-activity relationship analysis of aldehyde semicarbazones and aryl hydrazones.
Twenty-eight condensation products of heterocyclic-a-carboaldehydes with N-aminooxazolidones, semicarbazides, thiosemicarbazides and benzoxycarbonyl hydrazide were synthesized so as to deduce the antiulcer pharmacophore or fragment of furazolidone (I), a prototype which has shown therapeutic efficacy in patients with gastric and duodenal ulcers. SAR analysis of the compounds indicated that the substitution of furan, thiophene, pyrrole or N-methyl pyrrole rings for 5-nitrofuran and the cleavage of the oxazolidone ring did not fully destroy the activity. The electron density of the carbonyl group was found to be of importance. A lead structure, therefore, was derived for further optimization.
Guo
Z
Z
Institute of Materia Medica, CAMS, Beijing.
Yang
G
G
Chu
F
F
Xu
G
G
Zhang
J
J
Zhang
S
S
Yu
Y
Y
D000818:Animals; D000897:Anti-Ulcer Agents; D055598:Chemical Phenomena; D002621:Chemistry; D005664:Furazolidone / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology; D051379:Mice; D051381:Rats; D013329:Structure-Activity Relationship
D000897:Anti-Ulcer Agents; D005664:Furazolidone