Design, synthesis and evaluation of tetrahydropyran based COX-1/-2 inhibitors

Chiral tetrahydropyrans were designed and synthesized by allylations of enantiomerically enriched β-hydroxy ketones followed by iodocyclisations and nucleophilic replacement of iodo group with C2H5S− and SCN−. In vitro COX-1/-2 inhibitory activities and the docking studies of these compounds identify some of them as moderate inhibitors of COX-1 and COX-2 enzymes.

Graphical abstractEnantioselective β-hydroxy ketones, obtained by the reactions of substituted benzaldehydes and acetone in presence of l-proline, on allylations followed by iodocyclisations and nucleophilic replacement reactions provided highly substituted tetrahydropyrans which act as moderate inhibitors of COX-1 and COX-2.Figure optionsDownload full-size imageDownload as PowerPoint slide