Synthesis and anti-inflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole

This work describes recent results from our research program aiming at the synthesis and evaluation of new compounds acting as potential anti-inflammatory drugs. A series of novel acyl-hydrazones bearing 2-aryl-thiazole moiety were synthesized by the condensation between derivatives of 4-[2-(4-methyl-2-phenyl-thiazole-5-yl)-2-oxo-ethoxy]-benzaldehyde and 2, 3 or 4-(2-aryl-thiazol-4-ylmethoxy)-benzaldehyde, respectively and different carboxylic acid hydrazides. The structures of newly synthesized compounds were established by the combined use of IR, 1H NMR, mass spectral data and elemental analysis. These compounds were tested in vivo for their anti-inflammatory activity, in an acute experimental inflammation. The acute phase bone marrow response, phagocytes’ activity and NO synthesis were evaluated. Compounds 10, 15, 17, 18 and 22 reduced the absolute leukocytes count due to the lower neutrophils percentage. Phagocitary index was decreased by all the compounds. Seven of them reduced the phagocitary activity. Five compounds inhibited NO synthesis, 3, 4, 16 and 22 stronger than Meloxicam, the anti-inflammatory reference drug.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► Various substituted 2-aryl-thiazole hydrazone derivatives were synthesized. ► Compounds 3, 4, 11, 13, 15, 20 and 22 were more potent inhibitors of PI than Meloxicam. ► Compounds 3, 11, 20 and 22 were more potent inhibitors of PA than Meloxicam. ►The NO synthesis was significantly reduced by 3, 4, 16, 21 and 22.