The five-membered heterocyclic group of pyrazoles/pyrazolines plays an important role in drug discovery besides to their wide range of the biological, agrochemical and pharmacological properties. The synthesis of the pyrazole derivative 2 was achieved via the reaction between oxoketene gem-dithiol 1 and phenylhydrazine. Subsequently, the key synthon mercaptopyrazole derivative 2 was qualified to react with some reagents e.g. DMF/POCl3 and/or sulfanilic acid to afford pyrazolecarbaldehyde 3 and/or pyrazolyl aminobenzenesulfonic acid derivative 4. The Schiff bases 5a-c and/or the cyclic adducts 7, 8a,b and/or 9 resulted from the condensation of the formylated adduct 3 with the appropriate substituted amines such as p-nitroaniline, p-chloroaniline, sulfanilic acid, guanidine sulfate, thiourea and/or acetophenone. The celecoxib analog 6 was obtained by the condensation of the terminal sulfonic acid group in the adduct 4 with 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one. The previously prepared compounds 2, 4-9 were obtained in both conventional and/or microwave conditions and they were screened for their in vivo and in vitro activities. The structures of the newly prepared compounds have been confirmed by means of elemental analyses, FT-IR, MS, 1H-NMR and/or 13C-NMR.