Synthesis of Derivatives of Purpurin-18 Imide and Research on  the Visible Spectra

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (2): 187-194. Previous Articles Next Articles

红紫素-18酰亚胺衍生物的合成及其可见光谱的研究

韩光范^*,a, 王进军^b, 常秀娟^a

^a华东船舶工业学院材料科学与工程学院镇江 212003
^b烟台大学应用化学系烟台 262005

收稿日期:2003-05-26 修回日期:2003-07-01 接受日期:2003-08-27 发布日期:2022-09-20

Synthesis of Derivatives of Purpurin-18 Imide and Research on the Visible Spectra

HAN, Guang-Fan^*,a, WANG, Jin-Jun^b, CHANG, Xiu-Juan^a

^aSchool of Material and Engineering, East China Shipbuilding Institute,Zhenjiang 212003
^bDepartment of Applied Chemistry, Yantai University, Yantai 264005

Received:2003-05-26 Revised:2003-07-01 Accepted:2003-08-27 Published:2022-09-20
Contact: * E-mail: gf552002@yahoo.com.cn

Abstract

Methyl pheophorbide-a was used as a starting material for modifications at 3-position and transformation on E-ring. The introduction of biphenylyloxy was performed by addition of HBr and nucleophilic substitution with phenylphenol on vinyl group at 3-position. In basic condition E-ring was converted into the cyclohexanedicarboxylic anhydride to form purpurin-18 derivatives by the air-oxidation. The oxidized products were reacted with hydroxylamine hydrochloride to generate purpurin-18 imide by ammonolysis andrecondensation. The alkylation and acylation for hydroxyl group linked with nitrogen were accomplished to give N-alkoxy and N-acyloxy purpurin-18 imides, respectively. The effect on their visible spectra by variation of chemicalconstruction was discussed. The structures of all new compounds were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

Key words: methyl pheophorbide-a, purpurin-18 methyl ester, photosensitizer, visible spectra, photodynamic therapy

Cite this article

HAN, Guang-Fan, WANG, Jin-Jun, CHANG, Xiu-Juan. Synthesis of Derivatives of Purpurin-18 Imide and Research on the Visible Spectra[J]. Chinese Journal of Organic Chemistry, 2004, 24(2): 187-194.

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红紫素-18酰亚胺衍生物的合成及其可见光谱的研究

Synthesis of Derivatives of Purpurin-18 Imide and Research on the Visible Spectra

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