Análogos de desoxirapontigenina: síntese, estudos de glicosilação com monossacarídeos raros e avaliação biológica

Abstract

Deoxyrhapontigenin (DRG) is a natural stilbenoid found in trace amounts and possesses distinct biological activities than those of resveratrol, from which it differs from by only a methyl group. Among the little reported, DRG exhibits anti-inflammatory, antimicrobial, and antineoplastic activities, and is an important in vivo metabolite of resveratrol in Alzheimer disease’s animal models. To further study DRG it is necessary to have a scalable efficient synthesis to produce it. In this work we prepared DRG in seven steps, from α-resorcylic acid, with 71% global yield and purity over 98% - as per quantitative nuclear magnetic resonance. On the course of synthesis, six advanced intermediaries were also prepared, and passable to use in other synthetic strategies, in high yield – over 90% global. To study the influence of varying the alkyl chain in DRG, six adducts were also synthesized, among them four novel compounds and a fluorescent derivative for histological studies. Glycosylation with rare sugars, D-allose and D-psicose, was also studied; synthesizing along the way three never reported saccharidic derivatives, thus opening new doors in the chemistry of these carbohydrates. The synthesized stilbenoid derivatives were assessed as to its anti-ureolytic, anti-fungal activities and the possibility of antiviral properties against SARS-CoV-2, the virus responsible for the COVID-19 pandemic in 2020-2022, with some promising results, that requires further studies.