Synthesis and antiviral activity of new pyrazole and thiazole derivatives

New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from α,β-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel pyrazolothiazol-4(5H)-ones (13-16) or pyrazolothiazoles (17-24). The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC50) value of 7 μg/ml. © 2009 Elsevier Masson SAS. All rights reserved.