Synthesis of 4,5-diaryl-1H-pyrazole-3-ol derivatives as potential COX-2 inhibitors.

doi:10.1021/JO049264K

Paper

Synthesis of 4,5-diaryl-1H-pyrazole-3-ol derivatives as potential COX-2 inhibitors.

Published Sep 17, 2004 · Meena V Patel, R. Bell, S. Majest

The Journal of organic chemistry

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83

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1

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Abstract

4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

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Study Snapshot

4,5-diaryl-1H-pyrazole-3-ol derivatives show good selectivity for COX-2 enzyme compared to COX-1 enzyme, offering potential as COX-2 inhibitors.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of 4,5-diaryl-1H-pyrazole-3-ol derivatives as potential COX-2 inhibitors.

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References

Citations

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Synthesis of Novel Pyrazolyl and Isoxazolyl 3-(Furan-2-yl)-5-Methyl-1-(4-Nitrophenyl)-1H-Pyrazol-4-yl Derivatives via Regioselectivity of the 1,3-Dipolar Cycloaddition

This study demonstrates the synthesis of novel pyrazolyl and isoxazolyl derivatives using 1,3-dipolar cycloaddition, resulting in pyrazolopyridazines and isoxazolopyridazines.

Novel Bipyrazole and Pyrazolopyridazinone derivatives via Regioselective Cycloaddition Reaction of Nitrilimines to Enaminone: Synthesis and Structural Elucidation

Novel bipyrazole and pyrazolopyridazinone derivatives were synthesized and confirmed by spectral data, elemental analyses, and single-crystal X-ray diffraction.