Synthesis and Anticancer Activity of New 2-methylquinoline with Pyridine, Thiazole and Pyrazole Derivatives

This work presents a novel class of 2-methylquinoline derivatives that combine pyridine, thiazole, pyrazole ring systems. The precursor 1-(2-methylquinolin-3-yl) ethanone (1) is combined with aldehydes, malononitrile and ethyl cyanoacetate in a one-pot synthesis to produce 2-amino-6-(2-methylquinolin-3-yl)-4-phenylpyridine hybrids 2 and 3. Synthetic approaches to the (E)-1-(1-(2-methylquinolin-3-yl) ethylidene) hybrids 5, 6, to treat 1 with thiosemicarbazide and 1-chloropropan-2-one and to get 7, 8, the compound 1 is treated with bromine and thiourea. Then by using 2-chloroacetyl chloride and ammonium thiocyanate compounds 9, 10 were prepared. Furthermore compound 11 is formed when dimethoxy-N,N-dimethylmethanamine and xylene are treated with compound 1. The 2-methyl-3-(1H-pyrazol-3-yl) quinoline motif 12 was prepared by reacting 1 with dimethylamine and then treating the mixture with hydrazine. When examined in vitro on A549 and MCF-7 cancer cell lines, the anti-cancer effects were comparable to those of doxorubicin.