title: Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities.
abstract: Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3'-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.
authors.affiliation: Department of Natural Product Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan. midori_arai@chiba-u.jp mish@chiba-u.jp.
authors.forename: Midori A
authors.initials: MA
authors.lastname: Arai
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Kofuji
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Tanaka
authors.forename: Natsuki
authors.initials: N
authors.lastname: Yanase
authors.forename: Kazuki
authors.initials: K
authors.lastname: Yamaku
authors.forename: Rolly G
authors.initials: RG
authors.lastname: Fuentes
authors.forename: Utpal Kumar
authors.initials: UK
authors.lastname: Karmakar
authors.forename: Masami
authors.initials: M
authors.lastname: Ishibashi
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002934:Cinnamates / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry; D057809:HEK293 Cells; D006801:Humans; D008958:Models, Molecular; D051153:Wnt Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D060449:Wnt Signaling Pathway / Q000187:drug effects*
chemical_list: C514039:3'-hydroxymethylrocaglate; D001572:Benzofurans; D001688:Biological Products; D002934:Cinnamates; D005419:Flavonoids; D051153:Wnt Proteins; C029010:cinnamic acid; C107772:rocaglamide; C041477:3-hydroxyflavone