2,3,5-Substituted tetrahydrofurans: COX-2 inhibitory activities of 5-hydroxymethyl-/carboxyl-2,3-diaryl-tetrahydro-furan-3-ols

5-Hydroxymethyl-/carboxyl-2,3-diaryl-tetrahydro-furan-3-ols have been investigated for their COX-1 and COX-2 inhibitory activities. Compounds 17, 18 and 20 have been identified as showing appreciable COX-2 inhibition and selectivity. The group present at C-5 of tetrahydrofuran and the substituents at the two phenyl rings, through their interactions with active site amino acid residues, significantly affect the activities of these molecules. The quantitative structure–activity relationship studies indicate the role of log P, TPSA, molecular connectivity and valence connectivity towards the activities of these molecules.

Graphical abstract5-Hydroxymethyl-/carboxyl-2,3-diaryltetrahydrofuran-3-ols with appreciable COX-2 inhibitory activities have been developed.Figure optionsDownload full-size imageDownload as PowerPoint slide