Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (2): 187-194. Previous Articles     Next Articles

红紫素-18酰亚胺衍生物的合成及其可见光谱的研究

韩光范*,a, 王进军b, 常秀娟a   

  1. a华东船舶工业学院材料科学与工程学院 镇江 212003
    b烟台大学应用化学系 烟台 262005
  • 收稿日期:2003-05-26 修回日期:2003-07-01 接受日期:2003-08-27 发布日期:2022-09-20

Synthesis of Derivatives of Purpurin-18 Imide and Research on the Visible Spectra

HAN, Guang-Fan*,a, WANG, Jin-Junb, CHANG, Xiu-Juana   

  1. aSchool of Material and Engineering, East China Shipbuilding Institute,Zhenjiang 212003
    bDepartment of Applied Chemistry, Yantai University, Yantai 264005
  • Received:2003-05-26 Revised:2003-07-01 Accepted:2003-08-27 Published:2022-09-20
  • Contact: * E-mail: gf552002@yahoo.com.cn

Methyl pheophorbide-a was used as a starting material for modifications at 3-position and transformation on E-ring. The introduction of biphenylyloxy was performed by addition of HBr and nucleophilic substitution with phenylphenol on vinyl group at 3-position. In basic condition E-ring was converted into the cyclohexanedicarboxylic anhydride to form purpurin-18 derivatives by the air-oxidation. The oxidized products were reacted with hydroxylamine hydrochloride to generate purpurin-18 imide by ammonolysis andrecondensation. The alkylation and acylation for hydroxyl group linked with nitrogen were accomplished to give N-alkoxy and N-acyloxy purpurin-18 imides, respectively. The effect on their visible spectra by variation of chemicalconstruction was discussed. The structures of all new compounds were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: methyl pheophorbide-a, purpurin-18 methyl ester, photosensitizer, visible spectra, photodynamic therapy