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Paper | Regular issue | Vol 98, No. 3, 2019, pp.416-428
Published online, 22nd March, 2019
DOI: 10.3987/COM-19-14048
One-Pot Cascade Synthesis of Pyrazole Based Isosteres of Valdecoxib by a [3+2] Cycloaddition Sequence and Evaluation of Their Cox Inhibitory Activity

Silvia Roscales,* Nicole Bechmann, Jens Pietzsch, and Torsten Kniess*

*Department of Radiopharmaceutical and Chemical Biology, Institute of Radiopharmaceutical Cancer Research, Helmholtz-Zentrum Dresden-Rossendorf, Bautzner Landstraße 400, 01328 Dresden, Germany


A series of 5-methyl-3,4-diaryl-substituted 1H-pyrazoles, N-isosteres of valdecoxib, was synthesized by a [3+2] cycloaddition/[1,5] sigmatropic rearrangement sequence starting from tosylhydrazine, aryl methyl ketones and terminal aryl alkynes bearing various substituents (H, Me, OMe, F, SO2Me, SO2NH2). New pyrazoles were prepared regioselectively in a one-pot process with moderate-good yields. All compounds were used in in vitro cyclooxygenase (COX) assays to determine inhibitory potency and selectivity to COX-1 and COX-2. In general, these new pyrazoles are characterized by selective COX-2 inhibition activity in a micromolar range.