It was found that psoralen derivative could perform a Friedel-Crafts acylation smoothly with acetic anhydride to give 5'-acetylpsoralen in a 73% yield. In the presence of boron trifluoride etherate, 5'-acetylpsoralen reacted with both aromatic amines and aliphatic amine smoothly to afford 5'-Schiff-base group substituted psoralen derivatives in 72%-92% yields. The novel synthetic method has the advantages of cheap materials, mild reaction conditions, good yields and high regioselectivity in the Friedel-Crafts acylation. Cell viability assay by MTT demonstrates that some of the psoralen derivatives 6 have antiproliferative activities.
Acylation ; Boranes ; chemistry ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Furocoumarins ; chemical synthesis ; chemistry ; pharmacology ; Humans ; Molecular Structure ; Schiff Bases ; chemistry