189501-41-5

Upstream product

• 59214-95-8 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-propanol 
• 352-13-6 4-flourophenylmagnesium bromide 
• 58697-03-3 3-(5,5-dimethyl-1,3-dioxanyl)-propionaldehyde 

Downstream Products

• 189500-93-4 1-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-pyrrole 
• 189501-43-7 3-(5.5-dimethyl-1,3-dioxan-2-yl)-1-[4-(methylsulfonyl)phenyl]propan-1-one 
• 189501-42-6 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one 

Relevant academic research and scientific papers

Prodrugs of benzenesulfonamide-containing COX-2 inhibitors

Prodrugs of COX-2 inhibitors are described as being useful in treating inflammation and inflammation-related disorders.

Substituted pyrrolyl compounds for the treatment of inflammation

A class of pyrrolyl derivatives is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I STR1 wherein R1, R2, R3 and R4 are as described in the specification.

1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase- 2

Series of 1,2-diarylpyrroles has been synthesized and found to contain very potent and selective inhibitors of the human cyclooxygenase-2 (COX-2) enzyme. The paper describes short and practical syntheses of the target molecules utilizing the Paal-Knorr reaction. Electrophilic substitution on 1 proceeds in a regioselective fashion, and the method was used to generate a number of tetrasubstituted pyrroles. Detailed SAR on the series has been studied by modifications of the aryl rings and the substituents in the pyrrole ring. Diarylpyrrole 1 is a very potent (COX-2, IC50 = 60 nm) and selective (COX-1/COX-2 = > 1700) inhibitor whereas the isomeric 2 is completely inactive against COX-2. Modifications of the substituents on the fluorophenyl ring in 1 yields very potent inhibitors of COX-2 (IC50 = 40- 80 nm) with excellent selectivity(1200 to >2500) vs COX-1, Analog 20 containing a sulfonamide group is an excellent inhibitor of COX-2 with an IC50 of 14 nm. Tetrasubstituted pyrroles containing groups such as COCF3, SO2CF3, or CH2OAr at position 3 in the pyrrole ring give excellent inhibitors (COX-2, IC50 = 30-120 nm). In vivo testing in the carrageenan- induced paw edema model in the rat establishes that the 1,2-diarylpyrroles are orally active antiinflammatory agents. Compound 3 is the most potent inhibitor of edema with an ED50 of 4.7 mpk.