One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by A [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
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, SO2NH...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2019 |
| País: | España |
| Institución: | Universidad Complutense de Madrid (UCM) |
| Repositorio: | Docta Complutense |
| Idioma: | inglés |
| OAI Identifier: | oai:docta.ucm.es:20.500.14352/126401 |
| Acceso en línea: | https://hdl.handle.net/20.500.14352/126401 |
| Access Level: | acceso abierto |
| Palabra clave: | 547 Química orgánica (Química) 2306 Química Orgánica |
| Sumario: | 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. |
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