Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents

Abstract

Syntheses of 2-methoxyestradiol (1) and eugenol (6) template based conformationally flexible and rigid diarylpropenes, 14(a–l) and 20(a–e), as nonsteroidal anticancer agents have been performed. The synthesized compounds were evaluated for their anticancer activity in in vitro using a panel of human cancer cell lines viz. MCF-7, A549, DU 145, KB and MDA-MB-231by SRB assay. Compounds 14i, 14k and 15a showed significant anticancer activity at IC₅₀ between 10.27 μM to 27.91 μM in different cancer cell lines. The most active molecule, 14k, inhibited proliferation of cells by inducing apoptosis and arresting the cell cycle at the G2/M phase. In vitro toxicity of these compounds (14i, 14k and 15a) in healthy hepatic monocyte (THP-1) cells showed high selectivity of compounds towards cancerous vs. healthy cells.