Studies On The Synthesis And Biological Activity Of Resveratrol Analogues And New Resveratral Glucosides

Resveratrol compounds are a class of natural products widely found in nature. These compounds have important biological activity, such as anticancer, antioxidant, lower blood lipids, protective role of the nervous system. In recent years people have paid attention to them. But their content in plants is low and difficult to extract. The results show that these compounds of chemical synthesis and natural product of extract have the same biological activity. In order to meet the biological activity of research and drug development needs, the thesis aims at the studies on total synthesis, structural modification and testing of biological activity testing of the resveratrol derivatives and its O-β-D glycosides.1. Five compounds resveratrol derivatives 1-5 are obtained by using 3,5-dihydroxybenzoic acid for raw material by methylation, LiAlH4 reduction, bromination, Arbuzov rearrangement, MOMO hydroxyl protection and Wittig-Horner reactions. Target compounds are made up of the aromatic A ring by the 3,5-dimethoxy group as substituent, aromatic B ring by the methoxy and hydroxy as substituent.2. Studies show that O-farnesene glycosylation can increase the biological activity of lipophilic, it is easier in the organisms through the cell membrane and enhance its biological activity. Resveratrol were treated with trans-farnesyl bromide and anhydrous potassium carbonate in anhydrous acetone at ambient temperature, two new compounds 6,7 were synthesized. These two compounds have been not reported in any literature.3. Resveratrol-O-acetyl glucosides 16-24 were synthesized by these resveratrol. Acetyl bromide glucose, galactose, acetyl bromide, acetyl bromide lactose, maltose acetyl bromide as glycosyl donor, using tetrabutylammonium bromide (TBBA) as phase transfer catalyst, the reaction was taken under the mild reaction conditions in strong alkaline sodium hydroxide of the water/chloroform system. The reaction in the Deacetylation was carried out in methanol/sodium methoxide system. The synthesis method was better than other methods with the mild reaction conditions, simple and three-dimensional post-processing advantages such as selectivity, and the relatively higher production rate. Finally glucose resveratrol glucoside, galactose glucoside, lactose glucoside, maltose glycoside 25-33 targeting the role of biological cells were synthesized in this study. These compounds have been not reported in literatures until now.The synthetic compounds structure has been confirmed by 1H NMR, MS and IR.