Synthesis and Biological Evaluation of Halogenated <i>E</i>-Stilbenols as Promising Antiaging Agents
Ester Sara Di Filippo,
Letizia Giampietro,
Barbara De Filippis,
Marwa Balaha,
Vincenzo Ferrone,
Marcello Locatelli,
Tiziana Pietrangelo,
Angela Tartaglia,
Rosa Amoroso,
Stefania Fulle
Affiliations
Ester Sara Di Filippo
Department of Neuroscience Imaging and Clinical Sciences, Interuniversity Institute of Myology, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Letizia Giampietro
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Barbara De Filippis
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Marwa Balaha
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Vincenzo Ferrone
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Marcello Locatelli
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Tiziana Pietrangelo
Department of Neuroscience Imaging and Clinical Sciences, Interuniversity Institute of Myology, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Angela Tartaglia
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Rosa Amoroso
Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
Stefania Fulle
Department of Neuroscience Imaging and Clinical Sciences, Interuniversity Institute of Myology, University “G. d’Annunzio” of Chieti-Pescara, 66100 Chieti, Italy
The increased risk of illness and disability is related to the age inevitable biological changes. Oxidative stress is a proposed mechanism for many age-related diseases. The crucial importance of polyphenol pharmacophore for aging process is largely described thanks to its effects on concentrations of reactive oxygen species. Resveratrol (3,5,4′-trihydroxy-trans-stilbene, RSV) plays a critical role in slowing the aging process but has a poor bioavailabity after oral intake. In this present work, a series of RSV derivatives was designed, synthesized, and evaluated as potential antioxidant agents. These derivatives contain substituents with different electronic and steric properties in different positions of aromatic rings. This kind of substituents affects the activity and the bioavailability of these compounds compared with RSV used as reference compound. Studies of Log P values demonstrated that the introduction of halogens gives the optimum lipophilicity to be considered promising active agents. Among them, compound 6 showed the higher antioxidant activity than RSV. The presence of trifluoromethyl group together with a chlorine atom increased the antioxidant activity compared to RSV.