Reaction of quercetin (QR) (1) with bromine under various conditions was studied. Interaction of QR with 2–3 equiv. of bromine in glacial acetic acid at 35–40°C for 2–4 h and 20–22°C for 24 h led to the formation of QR 6,8-dibromide (2) (52–54% yields, 96–98% purity by HPLC). Interaction of QR with 2–5 equiv. bromine in absolute ethanol at 0–5°C and 20–22°C for 24 h led to the formation of 3-O-ethyl-QR-2,3,6,8,5′-pentabromide (3) (95–97% purity by HPLC) the output of which depends on the quantity of bromine. It was shown in MDCK cell culture that compound 2 exhibits a moderate inhibitory activity against pandemic influenza virus A/H1N1/pdm09 (EC50 6.0 μg/mL, CTD50 97.7 μg/mL, SI 16). Compound 3 was inactive.
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