Chinese Journal of Organic Chemistry >
Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives
Received date: 2013-10-06
Revised date: 2013-11-08
Online published: 2013-11-20
Supported by
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).
Pheophorbide-a methyl ester, as a degraded product from chlorophyll-a, was used as a starting material, and the modifications for functional groups along N21-N23-axis were completed by making use of reactive regions. The tri-membered ring structures were introduced to the macrocyclic chromophore in different position by 1,3-polar cycloaddition, Grignard reaction and reconstructions for exocyclic ring. A series of unreported chlorins related to chlorophyll were synthesized and their chemical structures were characterized by UV, IR, 1H NMR, MS techniques and elemental analysis. The different effects on the physical and chemical properties of chlorophyllous chlorins by introduction of cyclopropyl group were discussed and in vitro photodynamic activities of some new compounds were determined.
Key words： chlorophyll-a; chlorin; chemical modification; cyclopropylation; synthesis
Liu Yang , Xu Xisen , Li Jiazhu , Yin Jungang , Qi Caixia , Wang Jinjun . Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 552 -560 . DOI: 10.6023/cjoc201310002
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