Synthesis of new methoxy derivatives of trans 2,3-diaryl-2,3-dihydrobenzofurans and evaluation of their anti-inflammatory activity

In the present study we synthesized new methoxy derivatives of trans 2,3-diaryl-2,3-dihydrobenzofurans, starting from suitable trans 2,3-diaryloxiranes, using regio- and stereoselective nucleophilic oxiranyl ring-opening reactions. The compounds were tested as anti-inflammatories in U937 cells. All compounds showed a significant role in inhibiting the NF-kappa B pathway and were able to restore normal ROS and NO level upon LPS activation. Moreover, regarding inhibition of ACLY, enantioenriched (50% ee) 7a(50) showed more potency than the racemic counterpart 7arac, together with a higher reduction of prostaglandin E-2 production, thus suggesting a stereoselective interaction in this pathway.