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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (5): 537-542. 上一篇    下一篇

研究论文

焦脱镁叶绿酸-a甲酯的溴化反应

王进军*,a, 韩光范b, 邬旭然a, 王鲁敏a, 沈荣基c   

  1. a烟台大学应用化学系 烟台 264005
    b华中船舶工业学院材料科学与工程学院 镇江 212003
    c仁济大学 釜山 韩国
  • 收稿日期:2003-07-23 修回日期:2003-10-13 接受日期:2003-11-26 发布日期:2022-09-20
  • 基金资助:
    国家科技部中韩政府间合作研究(2002)资助项目.

Bromination Reaction of Methyl Pyropheophorbide-a

WANG, Jin-Jun*,a, HAN, Guang-Fanb, WU, Xu-Rana, WANG, Lu-Mina, SHIM, Young-Keyc   

  1. aDepartment of Applied Chemistry, Yantai University, Yantai 264005
    bSchool of Material and Environmental Engineering, East China Shipbuilding, Zhenjiang 212003
    cLnie University, Pusan, Korea
  • Received:2003-07-23 Revised:2003-10-13 Accepted:2003-11-26 Published:2022-09-20
  • Contact: *E-mail: wjj1955@163.com

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以焦脱镁叶绿酸-a甲酯为起始原料,通过与各种溴化剂的加成和取代反应,在3-位和meso-位上引进溴原子,分别得到单取代、三取代和四取代的溴化卟吩;其3-位乙烯基与溴化氢的加成则分别生成正常溴代产物和水解产物及其酯化产物.用四氧化锇和高碘酸钠将焦脱镁叶绿酸甲酯的3-位乙烯基氧化成醛,进而与四溴化碳和三苯基磷反应,生成3-位偕二溴取代焦脱镁叶绿酸衍生物.所合成的叶绿酸溴代衍生物均经UV, IR, 1H NMR及元素分析证明其结构.

关键词: 焦脱镁叶绿酸-a甲酯, 溴化反应, 可见光, 光动力疗法

Methyl pyropheophorbide-a (MPP-a) was usedas starting material for the synthesis of new bromine-substituted chlorin compounds. The bromines were introduced into 3-position and meso-position of the chlorin chromophore by addition reaction and substitution reaction with the bromide reagents to give mono-bromine- and tri-bromine-substituted chlorines.The formal addition product, hydrolyzate and esterified product were obtained by addition reaction with 30% hydrogen bromide in acetic acid. MPP-a was oxidized with OsO4 in THF containing catalytic pyridine at 0 ℃ and followed by glycol cleavage with sodium periodate in aqueous THF to give the methyl pyropheophorbide-d (MPP-d) which was reacted with carbon tetrabromide and triphenylphosphine to generate gem-dibromine substituted product at 3b-position. The structures of all new compounds were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: methyl pyropheophorbide-a, bromination reaction, visiblespectra, photodynamic therapy (PDT)