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 eects on concentrations of reactive oxygen species. Resveratrol (3,5,40-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 dierent electronic and steric properties in dierent positions of aromatic rings. This kind of substituents aects 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.

Synthesis and Biological Evaluation of Halogenated E-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
2020-01-01

Abstract

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 eects on concentrations of reactive oxygen species. Resveratrol (3,5,40-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 dierent electronic and steric properties in dierent positions of aromatic rings. This kind of substituents aects 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.
File in questo prodotto:
File Dimensione Formato  
Molecules (2020) 5770 25(23) 1-17.pdf

accesso aperto

Descrizione: Article
Tipologia: PDF editoriale
Dimensione 3.69 MB
Formato Adobe PDF
3.69 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11564/739501
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 9
social impact