4892-23-3Relevant articles and documents
Novel imidazole derivatives with anti-inflammatory activity
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, (2008/06/13)
Novel imidazole derivatives of formula I and their salts, solvates and prodrugs, wherein the meanings of the different radicals are as shown in the description. Said compounds are useful as anti-inflammatory agents.
Synthesis of (1R,2S)-1-(3′-chloro-4′-methoxyphenyl)-1,2- propanediol (trametol) and (1R,2S)-1-(3′,5′-dichloro-4′- methoxyphenyl)-1,2-propanediol, chlorinated fungal metabolites in the natural environment
Kousaka, Takeshi,Mori, Kenji
, p. 697 - 701 (2007/10/03)
(1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2-propanediol (Trametol, 3), a metabolite of the fungus Trametes sp. IVP-F640 and Bjerkandera sp. BOS55, was synthesized by employing Sharpless asymmetric dihydroxylation as the key step. Similarly, the (1R,2S)-isomer of 1-(3′,5′-dichloro- 4′-methoxyphenyl)-1,2-propanediol (4), another metabolite of Bjerkandera sp. BOS55, was synthesized by asymmetric dihydroxylation.
1,2-Diarylimidazoles as potent, cyclooxygenase-2 selective, and orally active antiinflammatory agents
Khanna, Ish K.,Weier, Richard M.,Yu, Yi,Xu, Xiang D.,Koszyk, Francis J.,Collins, Paul W.,Koboldt, Carol M.,Veenhuizen, Amy W.,Perkins, William E.,Casier, Jacquelen J.,Masferrer, Jaime L.,Zhang, Yan Y.,Gregory, Susan A.,Seibert, Karen,Isakson, Peter C.
, p. 1634 - 1647 (2007/10/03)
Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mpk for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mpk) and hyperalgesia (ED50 = 11- 40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.