title: Synthesis and "double-faced" antioxidant activity of polyhydroxylated 4-thiaflavans.
abstract: A simple synthetic methodology, based on the inverse electron demand hetero Diels-Alder reaction of electron-poor dienic o-thioquinones with electron-rich styrenes used as dienophiles, allowed the preparation of several polyhydroxylated 4-thiaflavans. Such compounds, as a function of the nature and position of the substituents on the aromatic rings, as well as of the oxidation state of the sulfur atom, are able to behave in vitro as efficient antioxidants mimicking the action of catechol containing flavonoids or/and tocopherols. The possibility of joining together the potentialities of two relevant families of natural polyphenolic antioxidants appears particularly appealing since an efficient protection against free radicals and other reactive oxygen species (ROS) depends in vivo upon the synergic action of different antioxidant derivatives.
authors.affiliation: Dipartimento di Chimica Organica, Polo Scientifico-Università di Firenze, via della Lastruccia 13, 50019, Sesto Fiorentino, Florence, Italy. stefano.menichetti@unifi.it
authors.forename: Stefano
authors.initials: S
authors.lastname: Menichetti
authors.forename: Maria Chiara
authors.initials: MC
authors.lastname: Aversa
authors.forename: Francesco
authors.initials: F
authors.lastname: Cimino
authors.forename: Alessandro
authors.initials: A
authors.lastname: Contini
authors.forename: Caterina
authors.initials: C
authors.lastname: Viglianisi
authors.forename: Antonio
authors.initials: A
authors.lastname: Tomaino
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D005419:Flavonoids / Q000138:chemical synthesis* / Q000494:pharmacology; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D059808:Polyphenols
chemical_list: D000975:Antioxidants; D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols