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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (2): 187-194. 上一篇    下一篇

研究论文

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   

  1. 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-Junb, CHANG, Xiu-Juana   

  1. 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

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选择脱镁叶绿酸-a甲酯为原料进行3-位化学修饰和E环改造.经3-乙烯基的溴化氢加成和与联苯酚的亲核取代反应,完成了3-位联苯氧基的引入;在碱性条件下,通过空气氧化将E环转变为环己二羧酸酐形成红紫素-18甲酯衍生物;所得氧化产物进而和盐酸羟胺反应,经胺解开环和再缩合成环构成N-羟基红紫素-18酰亚胺衍生物;对其羟基进行烷基化和酰基化,合成出N-取代红紫素-18酰亚胺衍生物.同时讨论了化学结构变化对分子可见光谱的影响.所合成新化合物的结构均经UV, IR, 1H NMR光谱和元素分析予以确认.

关键词: 脱镁叶绿酸-a甲酯, 红紫素-18甲酯, 光敏剂, 可见光谱, 光动力疗法

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