Synthesis And Bioactivities Of Flavanone Derivatives

To optimizate the structure of natural biological activity compounds and to find the lead compounds are the effective methods to develop new drugs with novel structures. As one kind of flavone family compounds, Flavanone is the plant second metabolites and distributed widespread in nature. These compounds always have been found in high plant and the root stem leaf flower and fruit of bracken plants. Most compounds of flavanone are the active ingredients of Chinese herbal medicine, as well this kind of compounds existed higher biological activities and lower toxicity. In recent years, the research on these compounds was the hot spots in the hemisphere of pharmacy. For the lower contents in natural plants and the complicated extraction craft, the investigation on reform, modification or SAR were relatively less.Farrerol, the extraction of Rhododendron dauricum L plants, was the flavanone family compounds. Nowadays, the research certificated that this compound could be used to cure the chronic bronchitis and also had the activity of antibiosis. We first found that this compound could inhibite the growth of SGC-7901 human gastric cancer cells significantly and the molecular mechanisms were investigated. So in this topic we designed to synthesis the Farrerol, and choose the B rings as the new derivation spot to synthesis a series of flavanone derivates, and investigated their biological activity and described the structure-activity relationship (SAR) preliminarily.The experiment starting with m-xylene, followed by nitration, reduction, hydrolysis and condensation, the type of flavanone compounds were synthesized, Structures of target compounds were confirmed by 1H-NMR,13C-NMR and ESI-MS.The activities were evaluated by the model of anti-tumor,anti-PTK,anti-vascular smooth muscle cells(VSMCs) vegetation,cytoprotective activity against H2O2-induced HUVEC injury and DPPH radical-scavenging activity.The results showed that the compounds 5b,5c 5d,5f,5i showed strong antitumor activity and the compound 5f,5i have significant anti-VSMCs vegetation activity. Meanwhile, The results strongly implied that the ortho-substituted electron-withdrawing groups are crucial for effective activity of these compounds. The results provided scientific bases for the further designing and synthesizing the flavanone derivatives.