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. © 2005 Elsevier Ltd. All rights reserved.
5-ARYLIDENE-2-IMINO-4-THIAZOLIDINONES: DESIGN AND SYNTHESIS OF NOVEL ANTI-INFLAMMATORY AGENTS / Ottana, R.; Maccari, R.; Barreca, M. L.; Bruno, G.; Rotondo, A.; Rossi, Antonietta; Chiricosta, G.; DI PAOLA, R.; Sautebin, Lidia; Cuzzocrea, S.; Vigorita, M. G.. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 13:13(2005), pp. 4243-4252. [10.1016/j.bmc.2005.04.058]
5-ARYLIDENE-2-IMINO-4-THIAZOLIDINONES: DESIGN AND SYNTHESIS OF NOVEL ANTI-INFLAMMATORY AGENTS.
ROSSI, ANTONIETTA;SAUTEBIN, LIDIA;
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. © 2005 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
