Synthesis and preliminary biological evaluation of quinoline-chrysin hybrids against head and neck squamous cell carcinoma

Chrysin belongs to natural flavonoids characterized wide spectrum of biological activity. Its use in treatment is limited by low bioavailability and rapid metabolism. The structure-activity relationship shows that introduction of substituent at C7 position of flavone scaffold increase the activity and bioavailability. In this study, a series of quinoline-chrysin hybrids was obtained. The structure of compounds was determined using spectroscopic methods. The anticancer activity of compounds was tested against neck and head squamous cell carcinoma lines (HNSCC), while the antioxidant activity was determined using DPPH method. The biological effect depends on the type of quinoline moiety. For the most active compounds, IC₅₀ values as low as ~ 13.8 µM for anticancer activity and ~ 24.5 µM for antioxidant activity were observed. For the most active compounds, their effect on the expression levels of TP53, BAX, and BCL2 genes was examined.