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

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (10): 1598-1605. Previous Articles Next Articles

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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

(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

(Department of Applied Chemistry, Yantai University, Yantai 264005)

Received:2009-01-11 Revised:2009-03-30 Published:2009-05-18

Abstract

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

Cite this article

WANG Jin-Jun, Diao-Li-Li, LI Jia-Zhu. Synthesis of Chloro-substituted Chlorin Derivatives with Basic Skeleton of Chlorophyll-a [J]. Chin. J. Org. Chem., 2009, 29(10): 1598-1605.

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具有叶绿素-a基本碳架的氯代二氢卟吩衍生物的合成

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

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