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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (1): 39-43. 上一篇    下一篇

研究论文

两种4’-对甲苯磺酰基异黄酮衍生物的合成及抗氧化性质研究

延玺*，夏玲玲，于静，丁万见   

  1. 北京师范大学化学系
  • 投稿日期:2007-03-26 修回日期:2007-08-02 发布日期:2008-01-14
  • 通讯作者: 延玺

Synthesis, and Studies on Antioxidation Properties of two 4’-p-toluenesulfonylisoflavone Derivatives

YAN Xi* XIA Ling-Ling YU Jing DING Wan-Jian   

  1. (College of Chemistry, Beijing Normal University, Beijing 100875)
  • Received:2007-03-26 Revised:2007-08-02 Published:2008-01-14
  • Contact: YAN Xi

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摘要 合成了未见文献报道的脂溶性较好的7-甲氧基-4’-对甲苯磺酰基异黄酮（L1）和7-氧乙酸乙酯-4’-对甲苯磺酰基异黄酮（L2），并得到了L1的单晶结构，采用IR、1H NMR、元素分析和X射线单晶衍射对L1进行了结构表征. 利用紫外分光光度法研究了化合物L1和L2对DPPH•自由基的清除作用，并采用量子化学半经验法（AM1）和Hartree-Fock 从头算的方法，计算了化合物分子中相关原子的电荷密度，探讨了它们与DPPH•自由基反应的可能活性位点. 获得了理论计算和光谱实验相一致的结果. 晶体结构测定表明, L1晶体属单斜晶系，P2 (1)/c点群， a=20.041(5)Å ，b=6.0876(17)Å ，c=16.516(4)Å. 理论推断和光谱实验表明，L2对DPPH自由基的清除效果好于L1.

关键词: 7-甲氧基-4'-对甲苯磺酰氧基异黄酮, 7-氧乙酸乙酯-4'-对甲苯磺酰氧基异黄酮, 晶体结构, 抗氧化, 量子化学

Abstract 7-methoxy-4’-p-toluenesulfonylisoflavone(L1) and 7- ethyl oxyacetate-4’-p-toluene -sulfonylisoflavone (L2) were synthesized and characterized by IR, 1H NMR and elemental analysis. Single crystals of L1 were determined by X-ray single crystal diffraction. The scavenging effect of L1 and L2 on DPPH• radical were detected by ultraviolet spectrophotometry. In addition , the semi-empirical method of quantum chemistry（AM1）and HF ab initio methods were used for calculating charge density of atoms in the molecule. The possible mechanism of eliminating DPPH• radical was explained. The experiment result shows that, the crystal [C23 H18 O6S] belongs to monoclinic space group P2 (1)/c with unit cell constants a = 20.041(5) Å , b = 6.0876(17) Å , c = 16.516(4) Å . The compound L2 can scavenge DPPH• radical more effectively than L1.

Key words: 7-methoxy-4'-p-toluenesulfonyloxyisoflavone, 7-ethoxyl carbonylmethoxy-4'-p-toluenesul- fonyloxyisoflavone, crystal structure, antioxidant, quantum chemistry