Synthesis and Anti‐inflammatory Activity Evaluation of Novel 7‐Alkoxy‐1‐amino‐4,5‐dihydro[1,2,4]triazole[4,3‐a]quinolines

Abstract

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(1H)‐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.