5-Substituted-2,3-diphenyltetrahydrofurans: a new class of moderately selective COX-2 inhibitors

Bioorg Med Chem. 2006 Dec 1;14(23):7910-6. doi: 10.1016/j.bmc.2006.07.044. Epub 2006 Aug 10.

Abstract

The nature of C-5 substituent and the configuration at C-5 carbon of 2,3-diphenyltetrahydrofurans, with chiral centres at C-2, C-3 and C-5, show a remarkable influence on their COX-2 inhibition and selectivity. Out of the eight compounds investigated here, 1b with COOH group and R* configuration at C-5, and 2d with CH2SCH2CH3 group and S* configuration at C-5 have been identified as lead molecules for further studies on COX-2 inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclooxygenase 2 Inhibitors / chemical synthesis*
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / pharmacology*
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / pharmacology*
  • Humans
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Cyclooxygenase 2 Inhibitors
  • Furans