Synthesis of Purpurin Imide Derivatives by Modification of Peripheral Functional Groups of Methyl Pheophorbide-a  

作　　者：韩光范 王进军 吕俊华 汪芳明 瞿燕 沈荣基 

机构地区：[1]School of Material Science and Engineering, Jiangsu Universi~' of Science and Technology, Zhenjiang, Jiangsu 212003, China [2]Department of Applied Chemistry Yantai University Yantai, Shandong 264005, China [3]School of Pharmaceutical Sciences, Jinan University, Guangzhou, Guangdong 510632, China [4]School of Nano Engineering. Inji University, Gyongnam 621-749, Korea

出　　处：《Chinese Journal of Chemistry》2006年第8期1069-1076,共8页中国化学（英文版）

摘　　要：A series of novel purpurin- 18 imide derivatives exhibiting long wavelength absorption and amphiphilicity were obtained from methyl pheophorbide-a （MPa） by modification of the peripheral functional groups. The vinyl group at 3-position was oxidized with OsO4 and NalO4 to form the formyl group and the Grignard reaction of this aldehyde with the alkyl magnesium bromide was carried out to give the corresponding 3-（1-hydroxylalkyl） pheophorbide-a. The E-ring of these chlorines was converted into anhydride ring to give purpurin derivatives by air oxidation The trans-3^2-alkyl purpurin derivatives were obtained by dehydration of hydroxyl group at 3^1-position. The N-hydroxyl purpurin imide was generated by treatment of the anhydride ring with hydroxylamine hydrochloride. The 3^1-alkylacyl-N-hydroxyl purpurin imides were obtained by oxidation of hydroxyl group at 3^1-position. The acylation of N-hydroxyl group was completed to afford N-acyloxy purpurin imides. The photocytoxicity of several compounds in vitro were tested.A series of novel purpurin- 18 imide derivatives exhibiting long wavelength absorption and amphiphilicity were obtained from methyl pheophorbide-a （MPa） by modification of the peripheral functional groups. The vinyl group at 3-position was oxidized with OsO4 and NalO4 to form the formyl group and the Grignard reaction of this aldehyde with the alkyl magnesium bromide was carried out to give the corresponding 3-（1-hydroxylalkyl） pheophorbide-a. The E-ring of these chlorines was converted into anhydride ring to give purpurin derivatives by air oxidation The trans-3^2-alkyl purpurin derivatives were obtained by dehydration of hydroxyl group at 3^1-position. The N-hydroxyl purpurin imide was generated by treatment of the anhydride ring with hydroxylamine hydrochloride. The 3^1-alkylacyl-N-hydroxyl purpurin imides were obtained by oxidation of hydroxyl group at 3^1-position. The acylation of N-hydroxyl group was completed to afford N-acyloxy purpurin imides. The photocytoxicity of several compounds in vitro were tested.

关 键 词：methyl pheophorbide-a purpurin-18 imide PHOTOSENSITIZER photodynamic therapy 

分 类 号：R454.2[医药卫生—治疗学] R730.5[医药卫生—临床医学]