Synthesis and "double-faced" antioxidant activity of polyhydroxylated 4-thiaflavans.
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.
Menichetti
Stefano
S
Dipartimento di Chimica Organica, Polo Scientifico-Università di Firenze, via della Lastruccia 13, 50019, Sesto Fiorentino, Florence, Italy. stefano.menichetti@unifi.it
Aversa
Maria Chiara
MC
Cimino
Francesco
F
Contini
Alessandro
A
Viglianisi
Caterina
C
Tomaino
Antonio
A
D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D005419:Flavonoids / Q000138:chemical synthesis* / Q000494:pharmacology; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D059808:Polyphenols
D000975:Antioxidants; D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols