Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2300-2308.DOI: 10.6023/cjoc201207022 Previous Articles     Next Articles



王振a, 杨泽a, 刘洋a, 徐希森a, 祁彩霞b, 王进军a,b   

  1. a 烟台大学化学化工学院 烟台 264005;
    b 山东省黄金工程技术研究中心工业应用 烟台 264005
  • 收稿日期:2012-07-17 修回日期:2012-08-20 发布日期:2012-08-22
  • 通讯作者: 王进军
  • 基金资助:
    中匈政府间科技合作(No. 2008-333-4-32)和山东黄金工程技术研究中心(2011年度)资助项目.

Chemical Modification of Methyl Pyropheophorbide-d and Synthesis of Chlorophyllous Chlorin Derivatives

Wang Zhena, Yang Zea, Liu Yanga, Xu Xisena, Qi Caixiab, Wang Jinjuna,b   

  1. a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005
  • Received:2012-07-17 Revised:2012-08-20 Published:2012-08-22
  • Supported by:
    Project supported by the Project of Technology Cooperation between Covernments of China and Hungary (No. 2008-333-4-32) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).

Chlorophyllous degraded products are ideal synthetic precursors for the synthesis of photodynamic therapy drugs. To obtain chlorophyllous photosensitizer, methyl pyropheophorbide-d was used as starting material, and its formyl and carbonyl groups on E-ring were modified by allomerization, Knoevenagel reaction, Hener reaction, Tiffeneau-Demjano rearrangement, Friedlaender condensation and reduction to build different chemical structures at 3-position and exocyclic E-ring. A series of chlorins with basic skeleton of chlorophyll were synthesized, and the relations between the molecular structures and their UV-Vis spectra were discussed. The possible mechanisms about corresponding reactions were tentatively proposed. The structures of new-reported chlorophyll derivatives were characterized by UV, IR, 1H NMR and elemental analysis.

Key words: chlorophyll-a, chlorin, methyl pyropheophorbide-d, chemical modification