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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 693-699. 上一篇    下一篇

研究论文

焦脱镁叶绿酸-a甲酯20-meso-1-位的亲电取代反应

王进军a,b，李家柱b,c， 殷军港b，刘永军*,a   

  1. (a中国科学院西北高原研究所 西宁 810001)
    (b烟台大学化学生物理工学院 烟台 264005)
    (c烟台大学药学院 烟台 264005)
  • 收稿日期:2007-04-13 修回日期:2007-09-10 发布日期:2008-04-17
  • 通讯作者: 刘永军

Electrophilic Reaction of Methyl Pyropheophorbide-a at 20-meso-1-Position

WANG Jin-Juna,b,LI Jia-Zhub,c,YIN Jun-Gangb,LIU Yong-Jun*,a   

  1. (a Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810001)
    (b Science and Engineering College of Chemistry and Biology, Yantai Univer-sity, Yantai 264005)
    (c College of Pharmacy, Yantai University, Yantai 264005)
  • Received:2007-04-13 Revised:2007-09-10 Published:2008-04-17
  • Contact: LIU Yong-Jun

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利用焦脱镁叶绿酸-a甲酯与亲电试剂发生的取代反应, 在焦脱镁叶绿酸-a甲酯的20-meso-位上分别引进硝基和卤原子, 得到了20-meso位取代的焦脱镁叶绿酸衍生物. 所合成的新叶绿素-a衍生物均经UV, IR, 1H NMR及元素分析证明其结构. 另外, 对叶绿素-a卟吩环上的芳香性和相应的化学反应活性也进行了讨论, 提出了可能的亲电取代反应机理.

关键词: 焦脱镁叶绿酸-a甲酯, 亲电取代反应, 叶绿素-a衍生物, 光动力疗法

By using the electrophilic reaction of methyl pyropheophorbide-a with various electrophilic reagents, the new 20-meso-(nitro and halogen)-substituted pyropheophorbide derivatives were obtained, the structures of which were characterized by UV, IR, 1H NMR spectra and elemental analysis. The aromaticity and reactive activity of the chlorin ring in the chlorophyll-a derivatives were discussed and the possible mechanism for the electrophilic reaction was tentatively proposed as well.

Key words: electrophilic substitution reaction, methyl pyropheophorbide-a, chlorophyll-a derivative, photodynamic therapy