Synthesis and in vitro evaluation of 5-arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones with antidegenerative activity on human chondrocyte cultures

• Published in: Bioorganic & medicinal chemistry 2007-12, Vol.15 (24), p.7618-7625
• Main Authors: Ottanà, Rosaria, Maccari, Rosanna, Ciurleo, Rosella, Vigorita, Maria Gabriella, Panico, Anna Maria, Cardile, Venera, Garufi, Floriana, Ronsisvalle, Simone
• Format: Article
• Language: English
• Subjects: 2-Phenylimino-4-thiazolidinones; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Antidegenerative activity; Arthritis - drug therapy; Biological and medical sciences; Bones, joints and connective tissue. Antiinflammatory agents; Cell Survival - drug effects; Cells, Cultured; Chondrocytes - drug effects; Chondrocytes - immunology; Drug Evaluation, Preclinical; Human chondrocyte; Humans; Imines - chemical synthesis; Imines - pharmacology; Indomethacin - pharmacology; Interleukin-1beta - pharmacology; Medical sciences; Models, Biological; Osteoarthritis; Pharmacology. Drug treatments; Reference Standards; Thiazolidines - chemical synthesis; Thiazolidines - pharmacology
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2007.09.001

5-Arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones ( 7, 8) were synthesized and evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1β. This in vitro model has proven to be a useful experimental model to reproduce the mechanisms involved in arthritic diseases. The cell viability, the amount of GAGs, the production of NO and PGE 2 and the inhibition of MMP-3 were measured. Several thiazolidinones 7 and 8 exhibited the ability to block the production or action of the degenerative factors induced by IL-1β.