Synthesis Of Isoflavones And Isoflavone Glycosides

Isoflavones, a subgroup of the flavonoid family, occur naturally in legumes and are consumed regularly in the human diet. They are known for their beneficial role in the prevention of hormone based cancers and coronary heart disease, as well as being potent antioxidant compounds. Isoflavones exist naturally as O-glycoside conjugates which posess antitumor, antioxidative, antifungal and especially reducing the levels of breast cancer risk factors including 17β-estradiol and progesterone.For the purpose of providing different substituted isoflavone glycosides for further study, in this thesis, the routes and conditions of the synthesis of isoflavones and isoflavone glycosides have been studied. Different deoxybenzoins were prepared by Hoesch and Friedel-Craft reaction respectively and followed by cyclisation to yield isoflavones. Then, the corresponding isoflavone-7-O-glucosides were synthesized by condensation of the compounds with 1-bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose in the presence of phase-transfer catalyst followed by the deprotection of acyl groups, under literature conditions and improved conditions respectively.In this thesis, 9 isoflavones, 5 isoflavone-7-O-(tetra-O-acetyl-β-D-glycopyranosides), 3 isoflavone-7-O-β-D-glucosides have been synthesized. The structures synthesized, in which three were new compounds, were confirmed by 1HNMR spectra.