3,3'-BI(1,3-THIAZOLIDIN-4-ONE) SYSTEM .8. 3,3'-(1,2-ETHANEDIYL) DERIVATIVES AND CORRESPONDING 1,1'-DISULFONES - SYNTHESIS, STEREOCHEMISTRY AND ANTIINFLAMMATORY ACTIVITY

To deeply investigate the influence of lipophilicity, phenyl substitut ion patterns and stereochemistry on pharmacological profiles of chiral bisarylthiazolidinones, frequently endowed with stereoselec tive anti inflammatory, analgesic, antihistaminic activities, we synthesized and explored some 3,3'-(1,2-ethanediyl) analogues 1-4, along with their S -oxidized derivatives 5-8. Each derivative can be isolated as 2R, 2'R/ 2S, 2'S (a) and 2R, 2'S- or 2S, 2'R- meso (b) diastereomers, which wer e explored by means of carrageenin edema test, acetic acid writhing an d hot plate tests, and also tested for gastrolesive potential and LD50 Independently of lipophilic and electronic features, disulfides 3b, 4 b and disulfones 7a, 8a, 8b displayed interesting activity levels whic h appear to be mainly linked to the disubstitution pattern on benzenic rings.