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Copper‐Catalyzed Multicomponent Reaction to Construct Fluorinated Indole‐quinoxalin‐2(1H)‐ones and Their Biological Evaluation

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A practical and mild multicomponent approach for 3-heterocyclation 2-trifluoromethylation of indoles with quinoxalin-2(1H)-ones and CF3SO2Na was reported by using low-cost and catalytic amount of CuF2 as the catalyst. Various indoles and quinoxalin-2(1H)-ones were well tolerated and the desired products were obtained. Moreover, morphological study indicated hydrochloride 6-CO2Me derivative was capable to induce apoptosis of A549 cancer cells.


A practical and mild three-component reaction of indoles, quinoxalin-2(1H)-ones, and CF3SO2Na is disclosed for the facile access of various 3-[2-(trifluoromethyl)1H-indol-3-yl]quinoxalin-2(1H)-ones using low-cost and catalytic amount of CuF2 as the catalyst. This strategy exhibits high site-selectivity, step economy, and broad substrates scope. Synthetic utility was demonstrated by the one-pot two-step synthesis of N-alkyl triazoles compounds via a click chemistry. To evaluate the antiproliferative activity of these compounds, A549 s (human lung adenocarcinoma cells) and HUVECs, as a model of toxicity, were used in MTT assay. The outcomes disclosed for 6-CO2Me and a N-alkyl triazole derivatives were of potent antiproliferative effect against A549 s (IC50 = 4.7 and 14.9 μM, respectively) with slight cytotoxicity in HUVECs. Morphological study was conducted by AO/EB dual staining, indicated hydrochloride 6-CO2Me derivative was capable of inducing apoptosis of A549 cells.

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