The Synthesis, Characterization And Biological Activity Of A Series Of Compounds Which Are Similar To Natural Product Sinapine

The study of the synthesis of natural products is the most remarkable fields in organic chemistry. The natural product sinapine widely exists in crucifer such as white mustard seed, yellow mustard seed, radish seed, pepperweed seed etc, and gets together in the form of shinapine thiocyanate in the plants. The sinapine plays an important role in the control of metabolism, improvement of disease resistance in plants and the nutrition quality. The sinapine has the bioactivity of antioxygen, anti-aging, resisting radiation, falling blood pressure etc, and plays an important role in these drug research.In this paper,10 kinds of analogues of sinapine are synthesized by the reaction of Doebner-Knoevenagel condensation, esterification, getting into quaternary ammonium salt, ion exchange using substituted benzaldehyde and malonate as the starting materials.All 10 target products and the other 10 intermediates are new compounds, a total of 20 compounds are not reported, the structure of which are characterized by IR,1HNMR and the other modern test methods.The water solubility of the sinapine thiocyanate extracting from the natural plants is not good, and is not conducive to some research of activity test, so the thiocyanate ion is replaced by the chloride ion which has a good water solubility using ion exchange technology and this compound is used to research its biological activity test accompany with the target compounds we have synthesized. The effects of the sinapine analogues on the smooth muscle isolated from rabbit are studied, and the experimental results showe that some compounds have loser and anesthetic effect on smooth muscle isolated from rabbit.The inhibitory effect of the synthetic sinapine analogues on cancer cells are studied using MCF-7 breast cancer cells as the model, and the role of the minimum effective concentration and optimal time points are explored using the target compound 1a for example. Respectively, 0.25 mg/L,0.5 mg/L,1 mg/L,2 mg/L,4 mg/L and 8 mg/L final concentration are prepared, and the survival rates of MCF-7 breast cancer cells are observed under each concentration in 24h, the results show that some target compounds can inhibite MCF-7 breast cancer cells.