Synthesis and biological activity of C-glycosyl 3-vinylchromones: Toward novel antioxidant drugs

4H-Chromen-4-ones (chromones) are a well-known class of oxygenated heterocyclic derivatives widely distributed in natural products. Due to their impressive pharmacological potential, chromones have attracted much attention. The extensive search for chromone derivatives resulted in the discovery of 3-(2-phenylvinyl)chromones, a small family of naturally occurring chromones characterized by a potent antioxidant activity.

Free radicals have been noted as a cause of many diseases, including inflammation, cancer, diabetes mellitus, and neurodegenerative diseases. In this regard, 3-vinylchromone derivatives of improved pharmacological profile are synthetic targets of prime importance for the development of novel antioxidant drugs for the prevention and treatment of diseases related to free radical pathology.

Naturally occurring chromones are usually glycosylated, which have a critical impact in their pharmacokinetics. The incorporation of a sugar moiety is capable of radically altering parent compound bioavailability following oral consumption, by modulating critical physicochemical parameters such as polarity. Even though O-glycosyl chromones are more common, their C-glycosyl counterparts attracted much recent interest on account of their enhanced stability and bioactivity. Over the last decade many C-glycosylflavonoids have been isolated and showed, in most cases, higher antioxidant potential than the corresponding O-glycosylflavonoids and aglycones.

Taking into account the above-mentioned considerations, this study is aimed at the synthesis of a novel family of C-glycosyl 3-vinylchromones and the in vitro evaluation of their antioxidant activity. The main goal of this research is to shed some light on the structure-radical scavenging activity relationship with the aim of developing new leads in the discovery of antioxidant drugs.