Synthesis and in vitro anticancer evaluation of 1,4-phenylene-bis-pyrimidine-2-amine derivatives

Authors : Meliha Burcu Gürdere, Erdoğan Kamo, Ayşe Şahin Yağlioğlu, Yakup Budak, Mustafa Ceylan

Pages : 263-271

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Publication Date : 9999-12-31

Article Type : Makaleler

Abstract :A series of 1,4-phenylene-bis-chalcones 3a-3h were synthesized by the reaction of terephthalaldehyde with substituted arylketones in this study. The novel 1,4-phenylene-bis-pyrimidine-2-amine derivatives 5a-5h were obtained by the addition of guanidine hydrochloride to 1,4-phenylene-bis-chalcone 3a-3h in ethanolic KOH under reflux conditions. The structure of the compounds was explained by means of IR, $^{1}$H NMR, $^{13}$C NMR, and elemental analyses. The anticancer activities of 3a-3h and 5a-5h were investigated against rat brain tumor cells and human uterus carcinoma in vitro$.$ Activity tests were performed as dose-dependent assays at eight concentrations. The positive control was 5-fluorouracil (5-FU). Compounds 3c and 3d were examined and they showed high activities as compared to 5-FU against C6 (rat brain tumor) and HeLa (human uterus carcinoma) cells. The anticancer activity of 5h was better than that of 5-FU at high concentrations cell-selectively against C6 cells.
Keywords : 1, 4-Phenylene-bis-chalcone, 1, 4-phenylene-bis-pyrimidine, HeLa, C6, anticancer activity, 5-fluorouracil