title: Synthesis and DPPH radical scavenging activity of prenylated phenol derivatives.
abstract: The synthesis of twenty six prenylated phenols derivatives is reported. These compounds were obtained under mild conditions via Electrophilic Aromatic Substitution (EAS) coupling reactions between phenol derivatives containing electron-donor subtituents and 3-methyl-2-buten-1-ol using BF(3)×OEt(2). Dialkylations were also produced with this method. The formation of a chroman ring by intramolecular cyclization between a sp2 carbon from the prenyl group with the hydroxyl substituent in the ortho position occurred with some phenols. All the synthesized compounds were evaluated as antioxidants according to a DPPH radical scavenging activity assay. IC(50) values of five synthesized compounds indicated they were as good antioxidants as Trolox™.
authors.affiliation: Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso, Chile. mauricio.osorio@usm.cl
authors.forename: Mauricio
authors.initials: M
authors.lastname: Osorio
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Aravena
authors.forename: Alejandra
authors.initials: A
authors.lastname: Vergara
authors.forename: Lautaro
authors.initials: L
authors.lastname: Taborga
authors.forename: Evelyn
authors.initials: E
authors.lastname: Baeza
authors.forename: Karen
authors.initials: K
authors.lastname: Catalán
authors.forename: Cesar
authors.initials: C
authors.lastname: González
authors.forename: Marcela
authors.initials: M
authors.lastname: Carvajal
authors.forename: Héctor
authors.initials: H
authors.lastname: Carrasco
authors.forename: Luis
authors.initials: L
authors.lastname: Espinoza
mesh_terms: D000975:Antioxidants / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D019800:Phenol / Q000138:chemical synthesis* / Q000737:chemistry*; D010851:Picrates / Q000737:chemistry*; D054876:Prenylation
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; D019800:Phenol; C004931:1,1-diphenyl-2-picrylhydrazyl