Citation: 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 shu

Synthesis of Cyanided Chlorophyllous Chlorin Derivatives and Study on Their Photodynamic Activities

Gao Na ^a ,
Wang Zhen ^b ,
Wu Jin ^b ,
Liu Chao ^b ,
Wang Jinjun ^a,b,*,,

a.
Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005
b.
College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Corresponding author: Wang Jinjun, wjj1955@163.com
Received Date: 30 June 2015
Revised Date: 16 November 2015

Fund Project: the National Natural Science Foundations of China 21272048

Figures(4)

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 and¹H 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.
- chlorophyll-a,
- chlorin,
- chemical modification,
- cyanation reaction,
- photodynamic activity
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