Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (12): 1714-1719. Previous Articles     Next Articles




  1. (a通化师范学院化学系 通化 134002)
    (b烟台大学应用化学系 烟台 264005)
    (c江苏科技大学材料科学与工程学院 镇江 212003)
    (d仁济大学微工程学院 釜山 韩国)
  • 收稿日期:2006-03-14 修回日期:2006-06-09 发布日期:2006-11-21
  • 通讯作者: 王进军

1,3-Dipolar Cycloaddition of Methyl Pheophorbide-a andSyn-thesis of Chlorophyll Derivative

JI Jian-Yea,LI Jia-Zhub,WANG Hub,LI Fu-Guob,HAN Guang-Fanc
SHIM Young Keyd,WANG Jin-Jun*,b   

  1. (a Departement of Chemistry, Tonghua Teachers College, Tonghua 134002)
    (b Department of Applied Chemistry, Yantai University, Yantai 264005, China)
    (c School of Material and Environmental Engineering, Jiangsu Uni-versity of Science and Technology, Zhenjiang 212003)
    (d School of Nano Engineer-ing, Inji University, Pusan, Korea)
  • Received:2006-03-14 Revised:2006-06-09 Published:2006-11-21
  • Contact: WANG Jin-Jun

From methyl pheophorbide-a (MPa, 1), the pheophorbide-a derivative substituted with hydro-pyrazol 2 was obtained by the 1,3-dipolar cycloaddition of vinyl group at 3-position with diazomethane. Ring opening of this chlorin was performed by heating to rearrange the hydropyrzaol ring into the cyclopropyl group. In basic condition the cyclopropyl-substituted chlorin 3 was converted into pyropheophorbide 4 by demethoxyformylation. The diazoethane was chosen as another dipole and reacted with chlorin 1 in 1,3-dipolar cycloaddition style to give 2-methylcyclopropyl-substituted stereoisomer chlorin 5. The treatment for demethoxyformylation like chlorin 2 yielded pyropheophorbide 6. The structures of all new chlorophyll-a deriva-tives 26 were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: pheophorbide, chlorophyll-a, pyropheophorbide, photodynamic therapy, 1,3-dipolar cycloaddition