Synthesis And Structural Identification Of The Isoflavone Derivatives Liu Xiao-hong

Daidzein(4',7-dihydroxy isoflavone) is the main active constituent of Pueraria lobata (Willd) Ohwi, and it has many pharmacyological activities. Because of the poor solubility, the curative effect of daidzein is slowly.To solve this problem, we modify daidzein with chemical methods. Fourteen new derivatives are obtained. The structures of them are identified by modern spectroscopy. The new compounds are : 7-methoxy-4'- hydroxy -3'-sodium sulfonate isoflavone and zinc cobalt copper, calcium, lanthanum sulfonate isoflavone and so on(I-XII), 7-methoxy-4'-hydroxy-3'-nitro isoflavone(XIII), 7-methoxy-8-glycoside-4'-hydroxy-3'-nitro isoflav- one(XIV).The crystal structure of 7-methoxy-4'-hydroxy-3'- cobalt sulfonate isoflavone(V) is studied. It has been determined by single crystal X-ray analysis. The crystals are triclinic, a = 0.7352(2)nm, b = 0.9936(2)nm, c =1.6301(4)nm. a =91.21(2) , =92.05(2) ,Y= 106.55(2) . V = 1140.1(5)nm3, Z = 2, Dc =1.517g/cm3, = 0.566mm"', space group P-l. The molecular structure of this compound is centrosymmetrical and it is not planar. The dihedral angle between the phenyl ring and the gamma- benzopyrone ring is 3.6-degrees. The structures of isoflavone are linked layer by layer, in which upper and down layers are connected by the hydrogen bonds of O(1}-H...O(15) and O(15)-H(15B)...O(7) each other. Furthermore, the rings of two isoflavone structures are stacking. Among them, A and C rings of an isoflavone structure is stacking with C and A rings of another isoflavone structure, the distance of them is 0.3560 nm.In the meanwhile, A ring of an isoflavone is stacking with A ring of another isoflavone. The distance of them is 0.3507nm. The 7-methoxyl-4'-hydroxyl isoflavone-3'-sulfonate anion and the six-coordinated Co(II) cation, water molecule, the oxygen atom of sulfonate, carbonyl and phenol group are hydrophilic, and the distance of them is near. There are 3D-network hydrogen bonds among them. On the contrary, in the area where are surrounded by two isoflavone structures, there is not hydrophilic groups and hydrogen bond. This area is like a large hole in the crystal of 7-methoxy-4'-hydroxy-3'- cobalt isoflavone sulfonate, and the formation of the crystal structure is due to the absence of the hydrophobic groups in the areas.The biological activities of resistance to hypoxia and anoxemia of 7 - methoxy-4'-hydroxy-3l-sodium(I)N cobalt(V) sulfonate isoflavones are tested. The results show that the biological activities of resistance to hypoxia and anoxemia of them are same as daidzein's.