Synthesis Of Bioactive Benzofunan Natural Products And Its Derivatives

1,4-Benzodioxane neolignans and benzofuran neolignans are potent ingredients of many medicinal plants, exhibit important biological activities. In order to meet the needs for selecting the substances with biological activities and developing new drugs, this thesis aims at the studies on synthesis 1,4-benzodioxane neolignans and benzofuran neolignans, structural modification and biological activity screening of benzofuran neolignan compounds.1. Aiming at constructing 1,4-benzodioxane skeleton, the synthetic routes were devised; through the following reaction process two 1,4-benzodioxane neolignans have been synthesized. Starting from Vanillin, via bromination reaction, hydrolysis reactions, Knoevenagel reaction, esterification reaction, Ag2O-catalyzed biomimetic oxidative coupling reaction in five steps, the compounds 1 containing a 1,4-benzodioxane skeleton was synthesized. The nature product 2 were synthesized via reduction of compounds 1 with lithium aluminium hydride.2. Starting from 3-methoxy-4-dihydroxyphenylmethacrylate and 3-methoxy-4,5-dihydroxyphenylmethacrylate, compound 3 containing a dihydro- benzofuran skeleton was synthesized via Ag2O-catalyzed biomimetic oxidative coupling reaction as the key step. Compound 4 were synthesized via reduction of compounds 3 with lithium aluminium hydride. Compound containing a dihydro-benzofuran skeleton was synthsized by cross coupling firstly. Compound 4 has an inhibitory effect on the HL-60.3. Aiming at constructing dihydrobenzofuran skeleton, the synthetic routes were devised. Starting from Vanillin, via Knoevenagel reaction, esterification reaction, Ag2O-catalyzed biomimetic oxidative coupling reaction, acetylized reaction, DDQ dehydrogenate reaction, reduction with H2/Pd-C, oxidation with MnO2/SiO2, the nature product 10(XH-14) with biological activities was synthesized, providing new synthetic routes for XH-14. The key steps was the Ag2O-catalyzed biomimetic oxidative coupling.4. The synthetic benzofuran neolignans as substrate, of which 4'-OH were replaced by a series of other functional group. Benzofuran neolignans with prenyl bromide or trans, trans-farnesyl bromide and anhydrous potassium carbonate in anhydrous acetone was to give four benzofurans neolignans-O-prenyl and-O-farnesyl compounds 29-33. The benzofuran neolignans acetyl-glucosides 34-40 were achieved via glycosidation with anhydrous potassium carbonate in anhydrous acetone at room temperature. The benzofuran neolignans glycosides 41-43 were achieved via deacetylation with a weak base (ammonia) for hydrolysis reagent.5. The compounds whicth have been achieved were evaluated for potential anticancer cell activity to PANC-1 (pancreatic cancer cell), SMMC-7721(hepatoma cell), SK-BR-3 (breast cancer cell) and HL-60(leukemia cells) by using the method of MTT.All of the synthesized new compounds 1-4,29-43 have been confirmed by 1H NMR, MS and IR.