title: 3,3'-Bi(1,3-thiazolidin-4-one) system. VIII. 3,3'-(1,2-Ethanediyl) derivatives and corresponding 1,1'-disulfones: synthesis, stereochemistry and antiinflammatory activity.
abstract: To deeply investigate the influence of lipophilicity, phenyl substitution patterns and stereo-chemistry on pharmacological profiles of chiral bisarylthiazolidinones, frequently endowed with stereoselective antiinflammatory, 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 were explored by means of carrageenin edema test, acetic acid writhing and hot plate tests, and also tested for gastrolesive potential and LD50. Independently of lipophilic and electronic features, disulfides 3b, 4b and disulfones 7a, 8a, 8b displayed interesting activity levels which appear to be mainly linked to the disubstitution pattern on benzenic rings.
authors.affiliation: Dipartimento Farmaco-chimico, Facoltà di Farmacia, Università di Messina, Italy.
authors.forename: M G
authors.initials: MG
authors.lastname: Vigorita
authors.forename: T
authors.initials: T
authors.lastname: Previtera
authors.forename: R
authors.initials: R
authors.lastname: Ottanà
authors.forename: I
authors.initials: I
authors.lastname: Grillone
authors.forename: F
authors.initials: F
authors.lastname: Monforte
authors.forename: M T
authors.initials: MT
authors.lastname: Monforte
authors.forename: A
authors.initials: A
authors.lastname: Trovato
authors.forename: A
authors.initials: A
authors.lastname: Rossitto
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000138:chemical synthesis* / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D013450:Sulfones; D013844:Thiazoles