Chinese Journal of Organic Chemistry >
Synthesis of Cyanided Chlorophyllous Chlorin Derivatives and Study on Their Photodynamic Activities
Received date: 2015-06-30
Revised date: 2015-11-16
Online published: 2015-11-16
Supported by
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reasearch Centre of Gold Nanotechnology (2011).
Pyropheophorbide-a methyl ester was used as a starting material, and its oxygenations were carried out by thaillum nitrate and air as oxidizing agent to introduce the formyl group and the formylmethyl group at 3-, 12-or 15-postion of chlorin periphery, respectively. After oximation these aldehyde groups were converted into cyano group under the reaction mediated from N,N-dimethylformamide and 2,4,6-trichloro-1,3,5-triazine. Dicyanomethylene moiety was established by Knoevenagel reaction of malononitrile with formyl group and 131-carbounyl group on the exocyclic ring. Mulcyano-substitutions on the chromophore were accomplished by further structure modifications. A series of unreported chlorins related to chlorophyll substituted with cyano-group were synthesized making use of cyanation at different positions on the periphery of chlorophyll degradation products. Their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The reaction mechanisms on the cyanation for the chlorophyllous chlorins were discussed and in vitro photodynamic activities of some new compounds were determined.
Gao Na , Wang Zhen , Wu Jin , Liu Chao , Wang Jinjun . Synthesis of Cyanided Chlorophyllous Chlorin Derivatives and Study on Their Photodynamic Activities[J]. Chinese Journal of Organic Chemistry, 2016 , 36(3) : 580 -589 . DOI: 10.6023/cjoc201506037
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