Issue in Honor of Prof. Vincenzo Tortorella ARKIVOC 2004 (v) 364-374
Aromatic Schiff bases and 2,3-disubstituted-1,3-thiazolidin-4-one derivatives as antiinflammatory agents
Iana Vazzanaa, Emanuela Terranovaa, Francesca Mattiolib, and Fabio Sparatorea*
a Dipartimento di Scienze Farmaceutiche, Università di Genova, Viale Benedetto XV, 3 – 16132 Genova, Italy and b Dipartimento di Medicina Interna, Sezione di Farmacologia e Tossicologia Clinica, Università di Genova, Viale Benedetto XV, 2 -16132 Genova, Italy E-mail: sparator@unige.it
Dedicated to Professor Vincenzo Tortorella, University of Bari, in the occasion of his “fuori ruolo” status (received 14 Jan 04; accepted 12 May 04; published on the web 16 May 04)
Abstract
Two small sets of aromatic Schiff bases and 2,3-diaryl-1,3-thiazolidin-4-one derivatives have been prepared and tested for antiinflammatory and antinociceptive activities. The thiazolidinone derivatives have been obtained from the azomethines through the addition of a-mercaptoacetic acid. Both types of compounds displayed good level of activity against carrageenan induced edema in rat hind paw, while only moderate activity was observed in the writhing test in mice.
Keywords: Aromatic Schiff bases, 2,3-diaryl-1,3-thiazolidinon-4-one derivatives, antiinflammatory agents, anti-nociceptive agents
Introduction
For a long time we have described1 sets of Schiff bases (diaryl- and arylheteroaryl azomethines) endowed with strong and long lasting antiinflammatory activity against the rat hind paw edema induced by carrageenan. The N-(2/3/4-pyridinylmethylene)-3-trifluoromethylbenzenamines 1-3 were of particular interest. The observed activity was clearly exceeding that of the starting amines and aldehydes, as intensity and duration is concerned, and could be related either to a latentiation of the active amine with an improved site-specific delivery, or better to a direct interaction of the azomethine itself with some enzymatic or receptorial protein, maybe at the level of thiol groups. Indeed active azomethines had been previously obtained starting from surely inactive amines and aldehydes.2
ISSN 1424-6376 Page 364 ©ARKAT USA, Inc
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