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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (10): 1598-1605. 上一篇    下一篇

研究论文

具有叶绿素-a基本碳架的氯代二氢卟吩衍生物的合成

王进军* 赵丽丽 李家柱   

  1. (烟台大学化学生物理工学院 烟台 264005)
  • 收稿日期:2009-01-11 修回日期:2009-03-30 发布日期:2009-05-18

Synthesis of Chloro-substituted Chlorin Derivatives with Basic Skeleton of Chlorophyll-a

Wang, Jinjun* Zhao, Lili Li, Jiazhu   

  1. (Department of Applied Chemistry, Yantai University, Yantai 264005)
  • Received:2009-01-11 Revised:2009-03-30 Published:2009-05-18

PDF

1435

被引次数

23

选择脱镁叶绿酸-a甲酯为起始原料, 经过化学结构修饰转换成其他叶绿素-a衍生物. 以过氧化氢/盐酸、N-氯代丁二酰亚胺(NCS)、氯化氢(或者浓盐酸)为氯化剂, 根据3-乙烯基和20-meso-位的不同化学反应活性, 通过亲电加成和亲电取代反应, 在二氢卟吩环上选择性地引进氯原子, 完成8种未见报道的具有叶绿素-a基本碳架的氯代二氢卟吩衍生物的合成. 所合成的新化合物均经UV, IR, 1H NMR及元素分析证明其结构.

关键词: 脱镁叶绿酸-a甲酯, 亲电反应, 选择性氯代, 氯代二氢卟吩, 光动力治疗

Methyl pheophorbide-a was chosen as a starting material and converted into other chlorophyll-a derivatives by chemical modification. Chlorine atoms were selectively introduced into the chlorin ring based on different reactivity between vinyl group at 3-position and 20-meso position by electrophilic addition and electrophilic substitution using hydrogen peroxide/hydrochloric acid, N-chlorosuccinimide (NCS), hydrogen chloride (or concentrated hydrochloric acid) as chlorinating reagent. Eight new chlorosubstituted chlorin de-rivatives with skeleton of chlorophyll-a were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: methyl pyropheophorbide-a, electrophilic reaction, selective chlorination, chlorinated chlorin, photodynamic therapy