Design, Synthesis, and Biological Evaluation of Novel Pyrazole, Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone

New pyrazole, oxazole, and pyridine derivatives bearing naphthalene and furan moieties have been prepared by condensing 3-(furan-2-yl)-1-(naphthalen-2-yl)prop-2-en-1-one 1 with different nitrogen and carbon nucleophiles such as hydrazine, hydroxylamine, cyclohexanone, cyclopentanone, ethyl cyanoacetate, and malononitrile, respectively. Cyclization of chalcone 1 with malononitrile in refluxing ethanol and ammonium acetate gave the corresponding dihydropyridine, which was condensed with different carbon electrophilic reagents such as ethyl cyanoacetate, ethyl acetoacetate, formamide, and acetic anhydride to yield the pyridine derivatives 13-16. Elemental and spectroscopic evidences characterized all the newly synthesized compounds. All of the newly synthesized compounds were tested in vitro for their anti-proliferative activities against HePG-2 and MCF-7 cell lines. Compounds 11, 8, and 15 displayed promising growth inhibitory effect toward the two cell lines compared with the standard drug doxorubicin.