265113-46-0

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 578727-01-2 5-(4-fluorophenyl)-1-(4-methylthiophenyl)-1H-imidazole 
• 104-96-1 4-methylsulfanylaniline 
• 459-57-4 4-fluorobenzaldehyde 
• 5470-49-5 4-methanesulfonylphenylamine 

Downstream Products

• 372107-27-2 1-(4-methylsulfonylphenyl)-5-[4-(1-pyrrolidinyl)phenyl]imidazole 
• 265113-76-6 4-chloro-5-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)imidazole 

Relevant academic research and scientific papers

1,5-Diarylimidazoles with strong inhibitory activity against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells

A series of 1,5-diarylimidazoles with 4-methylsulfonylphenyl group were prepared and evaluated for the inhibitory activities against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells. Most of synthesized 1,5-diarylimidazoles exhibited strong inhibitory activities regardless of the position of the 4-methylsulfonylphenyl group. The 1,5-diarylimidazoles with a halogen atom (3c-3h, 3n-3p) gave mostly excellent inhibitory activities regardless of the position and species of the halogen atom. Whereas the 1,5-diarylimidazoles with two fluorine atoms (3k, 3l, 3r, 3s) showed rather reduced inhibitory activities.

Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-Diarylimidazoles

The synthesis and the pharmacological activity of a series of 1,5-diarylimidazoles developed as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema, air-pouch, and hyperalgesia tests). Modification of all the positions of two regioisomeric imidazole cores led to the identification of 4-[4-chloro-5-(3-fluoro4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide (UR-8880, 51f) as the best candidate, which is now undergoing Phase I clinical trials.

NOVEL IMIDAZOLES WITH ANTI-INFLAMMATORY ACTIVITY

Compounds of formula I wherein: one of X or Y represents N and the other represents C; R1 represents hydrogen, methyl, halogen, cyano, nitro, -CHO, -COCH3 or -COOR4; R2 represents optionally-substituted aryl or heteroaryl; R3 represents C1-8 alkyl, C1-8 haloalkyl or -NR4R6; R4 represents hydrogen, C1-8 alkyl or arylC0-8 alkyl; R6 represents hydrogen, C1-8 alkyl, arylC1-8 alkyl, -COR8 or -COOR8; R8 represents C1-8 alkyl or C1-8 haloalkyl; aryl in the above definitions represents phenyl or naphthyl; and heteroaryl in the above definitions represents pyridine, pyrazine, pyrimidine or pyridazine, which can be optionally fused to a benzene ring. These compounds are useful as cyclooxygenase-2 inhibitors.