Syntheses,Crystal Structures and Biological Activity of Bimethylation Daidzein Sulfonates

Abstract

Abstract:

The water soluble derivatives of daidzein sodium 7,4′-bimethoxylisoflavone-3′-sulfonate(1) and copper(Ⅱ) 7,4′-bimethoxylisoflavone-3′-sulfonate(2) were synthesized and their structures were characterized by IR, NMR, ESI-MS and X-ray diffraction analyses. In the crystal structure of compound 1, each sodium ion is six-coordinated by oxygens from the methoxyl and suflo-group of 7,4′-bimethoxylisoflavone-3′-sulfonate and H2O. Two adjacent sodium ions were bridged by the oxygen atoms from suflo-group and a six-membered ring is formed. The six-membered ring consists of two sodium ions, three oxygen atoms from two suflo-groups and a sulfur atom. The Na—O bonds of adjacent rings are paralleled with each other and form an one-dimensional zigzag sodium polyion chain along axis c of the unit cell. The sodium ions chains are also connected by the hydrogen bonds among coordination water molecules, between coordination water molecules and oxygen from suflo-group. The coordination interaction, hydrogen bonds and the electrostatic interaction between sodium ion and —SO^-₃ made compound 1 assemble supramolecular ion polymer with two-dimensional structure. The crystal of compound 2 consists of [Cu(H₂O)₆]²⁺, C₁₇H₁₃O₄SO^-₃ and H₂O. Cu(Ⅱ) is at the symmetry center of structure of compound 2 and octahedrally coordinated by six water molecule. [Cu(H₂O)₆]²⁺, C₁₇H₁₃O₄SO^-₃ and H₂O form several kinds of hydrogen bonds. The distance of 0.358 2 nm between anti-parallel isoflavone rings shows a π…π stacking interaction. The hydrogen bonds and π…π stacking interaction lead to supramolecular formation with three-dimensional network structure. The biological activities of resistance to hypoxia and anoxemia were tested, the results show that the biological activities of resistance to hypoxia and anoxemia of compounds 1 and 2 were better than that of daidzein.

Key words: Daidzein; Sodium 7,4′-bimethoxylisoflavone-3′-sulfonate; Copper(Ⅱ) 7,4′-bimethoxylisoflavone-3′-sulfonate; Crystal structure; Resistance to hypoxia and anoxemia, Daidzein, Sodium 7,4'-bimethoxylisoflavone-3'-sulfonate, Copper(Ⅱ) 7,4'-bimethoxylisoflavone-3'-sulfonate, Crystal structure, Resistance to hypoxia and anoxemia

CLC Number:

O624

TrendMD:

ZHANG Zun-Ting, WANG Qiu-Ya, HE Yun, WANG Xiao-Bing, XUE Dong, ZHENG Jian-Bin. Syntheses,Crystal Structures and Biological Activity of Bimethylation Daidzein Sulfonates[J]. Chem. J. Chinese Universities, 2005, 26(12): 2247.

References

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