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Synthesis and Anti‐inflammatory Activity Evaluation of Novel 7‐Alkoxy‐1‐amino‐4,5‐dihydro[1,2,4]triazole[4,3‐ a ]quinolines
Author(s) -
Sun XianYu,
Wei ChengXi,
Chai KyuYun,
Piao HuRi,
Quan ZheShan
Publication year - 2008
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200700182
Subject(s) - chemistry , amine gas treating , 1,2,4 triazole , alkoxy group , ibuprofen , triazole , stereochemistry , anti inflammatory , quinolone , structure–activity relationship , xylene , pharmacology , combinatorial chemistry , medicinal chemistry , biochemistry , organic chemistry , in vitro , toluene , medicine , antibiotics , alkyl
In this study, a novel series of 7‐alkoxy‐1‐amino‐4,5‐dihydro[1,2,4]triazole[4,3‐ a ]quinolines were synthesized by using 6‐hydroxy‐3,4‐dihydro‐2(1 H )‐quinolone as the starting material. These compounds were evaluated for anti‐inflammatory activity through monitoring their ability to inhibit xylene‐induced ear edema in mice. Some of the tested compounds exhibited significant activity, and the compounds 5f (7‐(benzyloxy)‐4,5‐dihydro[1,2,4]triazolo[4,3‐ a ]quinolin‐1‐amine) and 5i (7‐( p ‐chlorobenzyloxy)‐4,5‐dihydro[1,2,4]triazolo[4,3‐ a ]quinolin‐1‐amine) showed the highest anti‐inflammatory activity (52% and 58% inhibition, respectively, at 2 h pre‐administration) which were comparable to or even slightly more potent than the reference drug ibuprofen (55%). Furthermore, the structure‐activity relationship of these 1,2,4‐triazole quinolines was demonstrated.