Synthesis And Bioactivity Of Resveratrol And Its Analogues

Resveratrol (3,4',5-trihydroxystilbene) is a phytoalexin which is present in a number of plant species. In recent years, many reports on the biological activities of resveratrol have been published, including antibacterium, antioxidation, antiplatelet aggregation, modulation of lipid metabolism, antitumor activity, and so on. Resveratrol is. the focus of the attention for its outstanding biological activities and excellent prospect in application.For the limited natural resources of resveratrol has restricted the research about its activities and applications, it becomes much more important to search for the synthetic methods for preparation of resveratrol. In this dissertation, we have investigated the synthetic method and operation process of resveratrol. According to the designed routine, we synthesized the target compound starting with 3,5-dimethoxybenzoic acid, which undergoes five steps including reduction, bromination, Arbuzov rearranment, Wittig-Horner reaction and demethylation with an overall yield of 35.0%. This synthetic routine is reasonable and applicable for resveratrol with available reagents, mild condition and shorter steps.Also, the problems in protecting phenolic hydroxy and removing protective groups, the method for bromination of alcohol, the influencing factor in Wittig-Horner reaction were discussed. Thesynthetic method for resveratrol would be the foundations of synthesis and applications for other polyhydroxystilbenes.Considering that resveratrol is similar to diethylstilbestrol in structure, it was reported that resveratrol had estrogen activity in vitro. In order to seek more estrogen-like compounds, we design and synthesize twenty resveratrol analogues S01-S20 based on replacing the groups in different position of two benzene rings. The results showed that S12 had the strongest effect on promoting MCF-7 cell growth, whose relative proliferative effect was close to 17 $ -Estradiol and Diethylstibestrol. The results of this study suggest that resveratrol analogues could be a new source of estrogenic agents, and a further investigation of its estrogen-like activity is worthwhile.