Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.

Abstract Eighteen new analogues of 5,3′-dihydroxy-3,6,7,8,4′-pentamethoxy-flavone, a potent natural cytotoxic and antimitotic flavone, were synthesized from calycopterin, the major flavonoid of Calycopteris floribunda Lamk., a traditional Asian medicinal plant. One of them, the 3′-amino substituted analogue, displayed almost the same activity as the reference compound. Pharmacomodulation at C-3′ on the B-ring, and at C-5,6,7 and 8 on the A-ring allowed to refine structure–activity relationships within the cytotoxic flavones series.