Studies On Synthesis Of New Chalcones, Flavonols And Their Biological Activities

Flavonoids, also called bioflavoinoids, are ubiquitous in nature plant kingdom.The immediate family members of flavonoids include flavones, chalcones, flavanones, and flavonols. In order to find new compounds being have biological activities and investigate Structure-activity relationships (SAR), we report the synthesis and antitumor activities in this paper for 3 series of natural and new chalcones, flavonone and flavonols.1. The simple and best feasible synthetic routes of flavonoids derivatives were proposed. That is chalcones acted as the key intermediates. We used resorcinol 7 and different aldehyde 8a-8g as our material, and then it was very easy to get chalcones 1a-1g by aldol condensation with yield of 60-89%. Then compounds (1a)-(1g) were depotected by 3mol/L HCl and O-prenylated to get hydroxylated chalcones (2a)-(2g) with high yield of 88-94% and O-prenylated chalcones with yield of 60-91%. Chalcones 1c was cyclizated differently to get flavanones 4c and flavonols 5c and hydrolysate 6c. Chalcones 1g was cyclizated to afford 5g and hydrolysate 6g. On the basis of the designation, thirty compounds were synthesized, including elven novel target compounds (three series) and nineteen intermediates.2. Synthesis method has been studied, such as, possible mechanism of condensation of ketone with aldehyde; An improvement of traditional synthesis method; Selectively synthesizing O-prenylated flavonoids from differently active multihydroxyl by controlling proportion between alkali and substrate.3. Three international standard molels, MDA-MB-231 (human breast cancer cell) , U251 (glia cancer cell) and MMP-9 (antiosteoporosis model) were chose. The biological activities of synthesized compounds against two tumor cells were tested. The results showed that some compounds were active in against tumor cells.4. All of the synthesized compounds have been confirmed by MS, IR, 1H NMR.