Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc1105231

Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 544-551.DOI: 10.6023/cjoc1105231 Previous Articles Next Articles

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红紫素-18 的卤化反应及其二氢卟吩类衍生物的合成

刘冉冉^a, 殷军港^a, 李家柱^a, 武进^a, 陈冠龙^a, 金英学^b, 王进军^a

a 烟台大学化学化工学院烟台 264005;
b 哈尔滨师范大学化学化工学院哈尔滨 150025

收稿日期:2011-05-23 修回日期:2011-07-16 发布日期:2012-03-24
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
山东省自然科学基金(No. Y2008B49)、科技部中匈政府间科技合作(No. 2009-2010 年度)资助项目.

Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives

Liu Ranran^a, Yin Jungang^a, Li Jiazhu^a, Wu Jin^a, Chen Guanlong^a, Jin Yingxue^b, Wang Jinjun^a

a Colledge of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025

Received:2011-05-23 Revised:2011-07-16 Published:2012-03-24
Supported by:
Project supported by the Natural Science Foundation of Shandong Province of China (No. Y2008B49) and the International Science and Technology Project between the Government of China and Hungary (No. 2008-444-4-32)

From purpurin-18 methyl ester the electrophilic addition of C(3)-vinyl group and electrophilic substitution at 20-meso-position produced regioselectively corresponding chloro-substituted or bromo-substituted products. The 3-pyrazolinylpurpurin- 18 ester, obtained by 1,3-dipolar cycloaddition of purpurin-18 with diazomethane, reacted with N-bromosuccinimide (NCS) or N-chlorosuccinimide (NBS) to generate halogenated pyrazolinyl-substituted chlorins. After pyrolysis the halogenations of 3-pyrazolinylpurpurin-18 ester gave 20-halogenated 3-cyclopropylchlorins. Methyl pheophorbide-a was used another starting material and converted into 20-bromopurpurin-18 derivatives by a series of chemical conversion for C(3)- vinyl group and bromination at 20-position. The structures of newly-reported title compounds were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

Key words: chlorophyll-a, purpurin-18, methyl pyropheophorbide-a, chemical modification, chlorin, photodynamic therapy (PDT)

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Liu Ranran, Yin Jungang, Li Jiazhu, Wu Jin, Chen Guanlong, Jin Yingxue, Wang Jinjun. Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives[J]. Chin. J. Org. Chem., 2012, (03): 544-551.

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红紫素-18 的卤化反应及其二氢卟吩类衍生物的合成

Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives

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