title: Antiangiogenic activity of synthetic dihydrobenzofuran lignans.
abstract: A series of synthetic dihydrobenzofuran lignans, obtained by biomimetic oxidative dimerization of caffeic or ferulic acid methyl ester followed by derivatization reactions, was tested for its antiangiogenic activity in the CAM (chorioallantoic membrane) assay. The dimerization product of caffeic acid methyl ester (2a) (methyl (E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate) showed a pronounced antiangiogenic activity, especially the 2R,3R-enantiomer.
authors.affiliation: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium.
authors.forename: Sandra
authors.initials: S
authors.lastname: Apers
authors.forename: Dietrich
authors.initials: D
authors.lastname: Paper
authors.forename: Jutta
authors.initials: J
authors.lastname: Bürgermeister
authors.forename: Slavka
authors.initials: S
authors.lastname: Baronikova
authors.forename: Stefaan
authors.initials: S
authors.lastname: Van Dyck
authors.forename: Guy
authors.initials: G
authors.lastname: Lemière
authors.forename: Arnold
authors.initials: A
authors.lastname: Vlietinck
authors.forename: Luc
authors.initials: L
authors.lastname: Pieters
mesh_terms: D020533:Angiogenesis Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002109:Caffeic Acids / Q000737:chemistry; D002384:Catalysis; D002823:Chorion / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D020533:Angiogenesis Inhibitors; D001572:Benzofurans; D002109:Caffeic Acids; D017705:Lignans; D011422:Propionates; C461040:methyl-3-(2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl)prop-2-enoate