Synthesis of Halogenated 1,5-Diarylimidazoles and Their Inhibitory Effects on LPS-Induced PGE2 Production in RAW 264.7 Cells |
| |
| Authors: | Zunhua Yang Yuanying Fang Jae-Min Kim Kyung-Tae Lee Haeil Park |
| |
| Institution: | 1.College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China; (Z.Y.); (Y.F.);2.College of Pharmacy, Kyung Hee University, Seoul 02453, Korea; (J.-M.K.); (K.-T.L.);3.College of Pharmacy, Kangwon National University, Chuncheon 24341, Korea |
| |
| Abstract: | A series of halogenated 1,5-diarylimidazole compounds were synthesized and their inhibitory effects on LPS-induced PGE2 production in RAW 264.7 cells were evaluated. A wide variety of 2,4-, 4-, and 2-halogenated 5-aryl-1-(4-methylsulfonylphenyl)imidazoles were synthesized for SAR study via two different pathways. Overall, 4-halogenated 5-aryl-1-(4-methylsulfonylphenyl)imidazoles, regardless of the species of halogen, exhibited very strong inhibitory activities of PGE2 production. Among them, 4-chloro-5-(4-methoxyphenyl)-1-(4-methylsulfonylphenyl)imidazole (3, IC50 3.3 nM ± 2.93), and 4-chloro-5-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)imidazole (13, IC50 5.3 nM ± 0.23) showed the best results. |
| |
| Keywords: | 1 5-diarylimidazole halogenation COX-2 PGE2 production anti-inflammatory |
|
|
