The Study On Synthesis Of Oral Physiological Active Isofavonoids And Isoflavone-O-glucosides

Isoflavones are a class of compounds mainly occurring in species of the Legumino- sae family.These compounds have received much attention recently due to their interesting biological activities. Many isoflavones exist naturally as O-glycoside conjugates. Isoflavonoid glycosides are common dietary phenolics which may be absorbed from the small intestine of humans,and have been reported to exhibit antitumor ,antioxidative ,antifungal ,and antihaemolytic activities. Nowadays, synthe- sis of sugar compounds to modify nature drugs has become an important field of pharmaceutical chemistry. This thesis aims at the studies on the syntheses of oral isoflavonoids and 7-O-Isoflavonoid glycosides.1. The second part reports the successful"one-pot"synthesis of isoflavones conveniently instead of the traditional two-step synthetic methods of isoflavones. In the improved method DMF/PCl5 is used to C1 reagent and BF3/Et2O is used to solvent and catalyzer. Three isoflavone compounds are synthesized with hydroxybenzene and phenylacetic acid in the improved method and four isoflavone derivatives are synthesized by modifying phenolic hydroxyl in B-ring and C-ring. All of these synthesized isoflavone compounds have been determined by means of MS, IR and 1H NMR spectroscopic methods.2. Isoflavone-O-glucosides were synthesized by these isoflavones. Previous methods for the synthesis of isoflavone-O-glucosides are low-yielding. In this work, a series of 7-hydroxy isoflavonoid glycosides have been synthesized from sugar (glucose,galactose and maltose) by a series synthetic steps including acetylation,bromization,glycosidation,deacetylation reaction. The synthetic procedure of glycosidation was modified by using anhydrous K2CO3 in a solvent mixture of DMF/acetone [V(DMF)/V(acetone)=(3:2)] and TBBA as a phase transfer catalyst. This method has advantages of mild reaction conditions, easy separation of products and high stereospecificticy; the higher yields were obtained in the synthesis of isoflavonoid glycosides.3. We have synthesized 16 Isolavonoids and isoflavone-O-glucosides compounds,9 of them were not reported in literatures until now. All of the synthesized compounds have been confirmed by 1H NMR, MS and IR spectra. The bioactivities of them have been evaluating .