Conventional and microwave-assisted synthesis, anticancer and antimicrobial evaluation of some new pyrazolone, pyrazole and pyrimidine derivatives

Abstract

Under conventional and microwave methods, reactions of ethyl 2-((4-nitrophenyl)diazenyl)-3-oxobutanoate 2 with nicotinohydrazide and thiosemicarbazide furnished the pyrazolone 5 and pyrimidine 7 derivatives, respectively. Treatment of compound 7 with acetic anhydride, phenyl isothiocyanate, ethyl bromoacetate, and phenacyl bromide produced the corresponding pyrimidine derivatives 8–11. Similarly, the reaction of 2-((4-nitrophenyl)diazenyl)malononitrile 3 with nicotinohydrazide and thiosemicarbazide gave the corresponding pyrazole 12 and pyrimidine 14 derivatives, respectively. Also, the addition reaction of ethyl 2-cyano-2-((4-nitrophenyl)diazenyl)acetate 4 with 2-aminobenzohydrazide and nicotinohydrazide give the corresponding pyrazolone derivatives 15 and 16, respectively. These entire novel scaffolds have been proved using elemental analysis, spectral data including IR, 1H-NMR in addition to mass spectra. These new scaffolds were screened for in vitro anticancer and antimicrobial activities. Most analogs revealed excellent to good results.