One-pot synthesis of fused benzoxazino[1,2,3]triazolyl[4,5-c]quinolinone derivatives and their anticancer activity

Abstract

A one pot strategy for the synthesis of fused benzoxazino[1,2,3]triazolyl[4,5-c]quinolinone derivatives 4a–4k via the reaction of 5-iodo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one (3) with different aryl azides under copper and palladium catalysis in a ligand free condition is achieved. The reaction provided the desired fused triazoles in good to excellent yields. The synthesized derivatives were evaluated for their in vitro cytotoxic activity against MCF-7, A-549 and HeLa cancer cell lines using MTT assay. The cytotoxic activity results revealed that, compound 4d has shown a broad spectrum of activity against MCF-7 and A-549 with IC₅₀ values of 11.18 ± 0.8 and 17.81 ± 0.6 μM, which are comparable to the standard drug, cisplatin. The remaining compounds have shown good to moderate activity against the tested cell lines. Based on the results obtained, a structure activity relationship (SAR) is discussed.