The synthesis and pharmacological activity of 5-arylidene-2-imino-4-thiazolidinones (3a–8a) are described. All derivatives exhibited significant activity levels in models of acute inflammation such as carrageenan-induced paw and pleurisy edema in rats. In particular, 5-(3-methoxyphenylidene)-2-phenylimino-3-propyl-4-thiazolidinone (3a) displayed high levels of carrageenan-induced paw edema inhibition comparable to those of indomethacin. In addition the ability of such a new class of anti-inflammatory agents to inhibit COX isoforms was assessed in murine monocyte/macrophage J774 cell line assay. 5-(4-Methoxyphenylidene)-2-phenylimino-3-propyl-4-thiazolidinone (6a), the most interesting compound in such an experiment, was docked in the known active site of COX-2 protein and showed that its 4-methoxyarylidene moiety can easily occupy the COX-2 secondary pocket considered as the critical interaction for COX-2 selectivity.

5-Arylidene-2-imino-4-thiazolidinones: Design and synthesis of novel anti-inflammatory agents

OTTANA', Rosaria;MACCARI, Rosanna;BARRECA, Maria Letizia;BRUNO, Giuseppe;ROTONDO, Archimede;CHIRICOSTA, giuseppa;CUZZOCREA, Salvatore;VIGORITA, Maria;DI PAOLA, ROSANNA
2005

Abstract

The synthesis and pharmacological activity of 5-arylidene-2-imino-4-thiazolidinones (3a–8a) are described. All derivatives exhibited significant activity levels in models of acute inflammation such as carrageenan-induced paw and pleurisy edema in rats. In particular, 5-(3-methoxyphenylidene)-2-phenylimino-3-propyl-4-thiazolidinone (3a) displayed high levels of carrageenan-induced paw edema inhibition comparable to those of indomethacin. In addition the ability of such a new class of anti-inflammatory agents to inhibit COX isoforms was assessed in murine monocyte/macrophage J774 cell line assay. 5-(4-Methoxyphenylidene)-2-phenylimino-3-propyl-4-thiazolidinone (6a), the most interesting compound in such an experiment, was docked in the known active site of COX-2 protein and showed that its 4-methoxyarylidene moiety can easily occupy the COX-2 secondary pocket considered as the critical interaction for COX-2 selectivity.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/1711748
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