Uncovering the Potential of O-Prenylated 3-aryl-benzopyran Derivatives as Osteogenic and Cancer Cell Growth Inhibitory Agents

Naturally, O-prenylation of 3-aryl-benzopyrans enhances the biological activities of these compounds. In this study, substituted O-prenylated 3-aryl-benzopyrans (21a-c, 22a-c, 23a-c, 24a-c 25a-c, 27 and 28) were synthesized and evaluated for osteogenic and cancer cell growth inhibitory potentials using cell-based in-vitro models. Amongst the target compounds, 21a, 22b, 23c, and 24c showed good osteogenic activity at 1 pM concentration, whereas 26 and 27 showed osteogenic activity at 100 pM and 10 nM, respectively. Compounds 21a, 22b, and 23c showed good cancer cell growth inhibitory activity against breast cancer cells (MCF-7 and MBA-231). Amongst active compounds, 27 presented the best anticancer activity against MDAMB-231 cells with selectivity towards non-cancerous cells [IC₅₀ 3.76 μM with SI 13.3]. The in-silico study of compounds showed their structural complementarities with the LBD of estrogen receptors and compliance with dragability parameters.