[Studies on antipeptic ulcer agents: the synthesis and structure-activity relationship analysis of heterocycle aldehyde (thio) semicarbazones and acyl hydrazones].
Twenty-eight condensation products of heterocycle-alpha-carboaldehydes with N-aminooxazolidones, semicarbazides, thiosemicarbazides, aminoguanidines, aromatic hydrazides and benzoxycarbonyl hydrazide were synthesized so as to deduce the antiulcer pharmacophore or fragment of furazolidone(I), the prototype, which shows therapeutic efficacy for patients with gastric ulcer. Analysis of the SAR of the compounds indicate that the substitution of furan, thiophene, pyrrole and N-methyl pyrrole rings for the 5-nitrofuran and the cleavage of the oxazolidone ring obtain the activity to some extent. The necessary electronic density of carbonyl group of compounds is of importance. A lead structure, therefore, is derived for further optimization.
Guo
Z R
ZR
Yang
G Z
GZ
Chu
F M
FM
Xu
G S
GS
Zhang
J J
JJ
Zhang
S R
SR
Yu
Y W
YW
D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis*; D051379:Mice; D051381:Rats; D012663:Semicarbazides / Q000138:chemical synthesis*; D012664:Semicarbazones / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000897:Anti-Ulcer Agents; D012663:Semicarbazides; D012664:Semicarbazones