Abstract
The synthesis and cytotoxicity evaluation of fourteen new chalcones containing 5-fluorouracil were introduced in which nine chalcones as Mannich bases 8a-i were synthesized from 2'-hydroxyacetophenone (1) in three steps including chloromethylation, N-alkylation and Claisen-Schmidt reactions. Other chalcones 14a-e were obtained from Click reaction between 1,3-dipropargyl-5-fluorouracil and azide derivatives of 2',4'-dihydroxychalcone. The bio-assay results showed that 11 chalcones (excluding 8d, 8f and 8h) exhibited cytotoxicity against four human cancer cell lines including Hep-G2, RD, LU-1 and FL in which compound 14e exhibited the most potent cytotoxicity against Hep-G2, RD, LU-1 and FL with IC50 values of 1.48, 10.59, 3.64 and 7.02 μg/mL, respectively.
Keywords: Chalcone, 5-fluorouracil, N-alkylation, click reaction and cytotoxicity.
Graphical Abstract
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