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

  • Eur J Med Chem. 2008 Dec;43(12):2792-9. doi: 10.1016/j.ejmech.2007.12.017.
Palwinder Singh  1 ,  Anu Mittal ,  Satwinderjeet Kaur ,  Subodh Kumar
Affiliations
  • 1. Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India. [email protected]
PMID: 18262309 DOI: 10.1016/j.ejmech.2007.12.017
Abstract

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 logP, TPSA, molecular connectivity and valence connectivity towards the activities of these molecules.