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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 12: 2300 - 2308

DOI: https://doi.org/10.6023/cjoc201207022

Articles

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

  • Wang Zhen ,
  • Yang Ze ,
  • Liu Yang ,
  • Xu Xisen ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005

Received date: 2012-07-17

  Revised date: 2012-08-20

  Online 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).

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Abstract

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

Cite this article

Wang Zhen , Yang Ze , Liu Yang , Xu Xisen , Qi Caixia , Wang Jinjun . Chemical Modification of Methyl Pyropheophorbide-d and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(12) : 2300 -2308 . DOI: 10.6023/cjoc201207022

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