title: Synthesis and biological activities of fluorinated chalcone derivatives.
abstract: We have designed and synthesized new 5-lipoxygenase inhibitors, fluorinated 3,4-dihydroxychalcones, and evaluated their biological activities with respect to antiperoxidation activity and in vitro antitumor activities. All fluorinated chalcones tested showed 5-lipoxygenase inhibition on rat basophilic leukemia-1 (RBL-1) cells and inhibitory action on Fe(3+)-ADP induced NADPH-dependent lipid peroxidation in rat liver microsomes. The potencies were comparable or better to that of the lead 3,4-dihydroxychalcone. 6-Fluoro-3,4-dihydroxy-2',4'-dimethoxy chalcone (7) was the most effective compound in the in vitro assay using a human cancer cell line panel (HCC panel) consisting of 39 systems.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770-8514, Japan.
authors.forename: Chika
authors.initials: C
authors.lastname: Nakamura
authors.forename: Nobuhide
authors.initials: N
authors.lastname: Kawasaki
authors.forename: Hideki
authors.initials: H
authors.lastname: Miyataka
authors.forename: Ezhuthachan
authors.initials: E
authors.lastname: Jayachandran
authors.forename: In Ho
authors.initials: IH
authors.lastname: Kim
authors.forename: Kenneth L
authors.initials: KL
authors.lastname: Kirk
authors.forename: Takeo
authors.initials: T
authors.lastname: Taguchi
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Takeuchi
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Hori
authors.forename: Toshio
authors.initials: T
authors.lastname: Satoh
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D002599:Chalcone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015227:Lipid Peroxidation / Q000187:drug effects; D016859:Lipoxygenase Inhibitors; D008297:Male; D008862:Microsomes, Liver / Q000201:enzymology; D009928:Organ Specificity; D051381:Rats; D017208:Rats, Wistar; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D006845:Hydrocarbons, Fluorinated; D016859:Lipoxygenase Inhibitors; D002599:Chalcone