title: Synthesis and antiproliferative activities of novel 5'-Schiff-base group substituted psoralen derivatives.
abstract: 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.
authors.affiliation: School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
authors.forename: Chao-Yue
authors.initials: CY
authors.lastname: Chen
authors.forename: Jian-Guo
authors.initials: JG
authors.lastname: Sun
authors.forename: Zhi-Zhen
authors.initials: ZZ
authors.lastname: Huang
authors.forename: Tim-Tak
authors.initials: TT
authors.lastname: Kwok
authors.forename: Kwok-Pui
authors.initials: KP
authors.lastname: Fung
authors.forename: Ping
authors.initials: P
authors.lastname: Wu
authors.forename: Fei-Yan
authors.initials: FY
authors.lastname: Liu
mesh_terms: D000215:Acylation; D001880:Boranes / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D012545:Schiff Bases / Q000737:chemistry
chemical_list: D001880:Boranes; D011564:Furocoumarins; D012545:Schiff Bases; C101707:boron trifluoride etherate