有机化学 ›› 2006, Vol. 26 ›› Issue (01): 43-50. 上一篇    下一篇

研究论文

红紫素-18酰亚胺衍生物的化学修饰

韩光范*,1,王进军2,瞿燕1,沈荣基3   

  1. (1江苏科技大学材料科学与工程学院 镇江 212003)
    (2烟台大学应用化学系 烟台 264005)
    (3韩国化学研究所生物有机化学部 大田 韩国)
  • 收稿日期:2005-01-17 修回日期:2005-07-01 发布日期:2005-12-31
  • 通讯作者: 韩光范

Chemical Modification of Derivatives of Purpurin-18 Imide

HAN Guang-Fan*,1,WANG Jin-Jun2,QU Yan1,SHIM Young Key3   

  1. (1 School of Material Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003)
    (2 Department of Chemistry, Yantai University, Yantai 262005)
    (3 Division of Bio-organic Chemistry, Korea Research Institute of Chemical and Technology, Dajen, Korea)
  • Received:2005-01-17 Revised:2005-07-01 Published:2005-12-31
  • Contact: HAN Guang-Fan

以脱镁叶绿酸-a甲酯为原料, 通过对其3-位乙烯基的氧化, 得到了3-甲酰基脱镁叶绿酸甲酯, 利用Wittig反应合成了对应的3-(2-取代的乙烯基)脱镁叶绿酸甲酯. 结合E环的改造, 将其转变成酸酐环进而转变成N-取代的酰亚胺环. 目标化合物具有亲水区和疏水区两部分, 吸收波长明显向红位移. 合成得到的红紫素-18酰亚胺衍生物有可能成为光动力疗癌的理想光敏剂. 合成的新化合物均由核磁共振、红外光谱、元素分析和质谱予以证实.

关键词: 脱镁叶绿酸-a甲酯, 红紫素-18酰亚胺, 光敏剂, 光动力疗法

Starting from methyl pheophorbide-a, 3-formyl substituted compound was synthesized through oxidation of its vinyl at 3-position. The Wittig reaction of the formyl group at 3-position was carried out to yield the corresponding methyl 3-(2-substituted ethenyl)pheophorbide-a. In basic conditon, E-ring was converted into the six membered cyclic anhydride to form N-substituted imide ring. The title compound has both hydrophilic and hydrophobic regions to demonstrate a considerable bathochromic shift of the major absorp-tion band in the red region of the optical spectrum. The derivatives of purpurin-18 imide were potentially ideal photosensitizers. The structures of all new compounds were characterized by elemental analysis, UV, IR, and 1H NMR spectra.

Key words: photosensitizer, photodynamic therapy, purpurin-18 imide, methyl pheophorbide-a