Synthesis and biological evaluation of a series of tangeretin-derived chalcones

A series of chalcones polyoxygenated on the ring A ( with pentamethoxy or 2''-hydroxy-3',4',5',6'-tetramethoxy substitution patterns) was synthesized from tangeretin, a natural Citrus flavonoid. These chalcones were evaluated for their antiproliferative, activation of apoptosis, inhibition of tubulin assembly and antileishmanial activities. Comparison with the reference analogous 3',4',5'-trimethoxylated chalcones showed that such peroxygenated substitution patterns on the ring A were less beneficial to these activities. (C) 2008 Elsevier Ltd. All rights reserved.