Design and Synthesis of a Novel Propargylated Imidazole–Chalcone Hybrid and Its Preliminary Cytotoxic Evaluation Against MCF-7 Breast Cancer Cells

الملخص

Breast cancer remains one of the most common types of cancer affecting women worldwide, and despite
the progress in treatment, there is still a continuous need to search for new compounds that may help in
improving therapeutic outcomes. In this work, a series of imidazole–chalcone hybrid compounds (PIM
1–PIM-5) were synthesized through a simple multistep procedure. The synthetic route started with N
alkylation of imidazole (1) using propargyl bromide (2) to form a propargyl-substituted imidazole
intermediate, followed by formylation at the 4-position of the imidazole ring. The resulting aldehyde was
then subjected to Claisen–Schmidt condensation with different substituted acetophenones (3) to afford the
target chalcone derivatives. The cytotoxic activity of the synthesized compounds was evaluated against
MCF-7 using the MTT assay. The results showed that the compounds exhibited different levels of growth
inhibition depending on the substituent on the aromatic ring. Among the tested derivatives, PIM-4
displayed the highest activity with an IC₅₀ value of about 7.4 µM, while the other compounds showed
moderate to lower activity. The structures of the synthesized compounds were confirmed using
spectroscopic techniques including FT-IR, ¹H NMR and ¹³C NMR.