Synthesis of Multi-ester Substitutied Chlorin Derivatives Related to Chlorophyll-a

doi:10.6023/cjoc1108301

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (02): 360-367 .DOI: 10.6023/cjoc1108301 Previous Articles Next Articles

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多酯基取代的叶绿素类二氢卟吩衍生物的合成

殷军港^a, 王振^b, 杨泽^a, 刘超^b, 赵丽丽^a, 王进军^a

a 烟台大学化学化工学院烟台 264005;
b 烟台大学药学院烟台 264005

收稿日期:2011-08-30 修回日期:2011-10-09 发布日期:2012-03-09
通讯作者: 王进军 E-mail:wjj1955@153.com
基金资助:
山东省自然科学基(No. Y2008B49)、中匈政府间科技合作(No. 2008-444-4-32)资助项目.

Synthesis of Multi-ester Substitutied Chlorin Derivatives Related to Chlorophyll-a

Yin Jungang^a, Wang Zhen^b, Yang Zea^a, Liu Chao^b, Zhao Lili^a, Wang Jinjun^a

a Colledge of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b Pharmacy College, Yantai University, Yantai 264005

Received:2011-08-30 Revised:2011-10-09 Published:2012-03-09
Supported by:
Project supported by the Natural Science Foundation of Shandong Province of China (No. Y2008B49) and the International Science and Technology Project between Governments of China and Hungary (No. 2008-444-4-32).

From methyl pheophorbide-a which was used as a starting material, purpurin-7 trimethyl ester and chlorin-p₆ trimethyl ester were synthesized by hydrogation-opening ring, allomerization and rearrangement reaction. The synthesis of ten unreported chlorin derivatives related to chlorophyll-a was accomplished by electrophilic adduction, electrophilic substitution, 1,3-dipolar cycloadduction and oxidation-rearrangement reaction to chemical modifications for C(3)-vinyl group, 20-meso-position, methyl group at 12-position and ester moieties at terminal positions. The structures of all new chlorins were characterized by UV, IR, ¹H NMR spectra and elemental analysis.

Key words: chlorophyll-a, methyl pheophorbide-a, chlorophyll degradation, chlorin, chemical modification, synthesis

Cite this article

Yin Jungang, Wang Zhen, Yang Zea, Liu Chao, Zhao Lili, Wang Jinjun. Synthesis of Multi-ester Substitutied Chlorin Derivatives Related to Chlorophyll-a[J]. Chin. J. Org. Chem., 2012, 32(02): 360-367 .

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[1] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.

[2] Grin, M. A.; Titeev, R. A.; Brittal, D. I.; Ulybina, O. V.; Tsiprovskiy, A. G.; Berzina, M. Y.; Lobanova, I. A.; Sivaev, I. B.; Bregadzeb, V. I.; Mironova, A. F. Mendeleev Commun. 2011, 21, 84.

[3] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.)

[4] Haas, R. N. S.; Jong, R. L. P.; Noushazare, M.; Erkelens, K.; Smijs, T. G. M.; Liu, Y.; Gast, P.; Schuitmaker, H. J.; Lugtenhurg, J. Eur. J. Org. Chem. 2004, 4024.

[5] Kozyrev, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949.

[6] Morishita, H.; Tamiaki, H. Bioorg. Med. Chem. 2003, 11, 4049.

[7] Li, J.-J.; Liu, W.-H.; Li, F.-G.; Wang, J.-J.; Suo, Y.-R.; Liu, Y.-J. Chin. J. Org. Chem. 2007, 27, 1594 (in Chinese). (李家柱, 刘万卉, 李付国, 王进军, 索有瑞, 刘永军, 有机化学, 2007, 27, 1594.)

[8] Wang, J.-J.; Li, J.-J.; Yin, J.-G.; Liu, Y.-J. Chin. J. Org. Chem. 2008, 28, 693 (in Chinese). (王进军, 李家柱, 殷军港, 刘永军, 有机化学, 2008, 28, 693.)

[9] Wang, J.-J.; Zhang, P.; Wang, P.; Chen, G.-L.; Li, F. G. Chin. J. Org. Chem. 2010, 30, 1192 (in Chinese ). (王进军, 张朋, 王朋, 陈冠龙, 李付国, 有机化学, 2010, 30, 1192.)

[10] Wang, J.-J.; Li, F.-G.; Li, Y.-W. Chin. J. Org. Chem. 2011, 31, 68 (in Chinese). (王进军, 李付国, 李韵伟, 有机化学, 2011, 31, 68.)

[11] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.

[12] Wang, P. M.S. Thesis, Yantai University, Yantai, 2009 (in Chinese). (王朋, 硕士论文, 烟台大学, 烟台, 2009.)

[13] Wang, J.-J.; Li, J.-Z.; Gryko, D.; Shim, Y.-K. Bull. Korea Chem. 2006, 27, 1083.

[14] Zhang, P. M.S. Thesis, Yantai University, Yantai, 2010 (in Chinese). (张朋, 硕士论文, 烟台大学, 烟台, 2010.)

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多酯基取代的叶绿素类二氢卟吩衍生物的合成

Synthesis of Multi-ester Substitutied Chlorin Derivatives Related to Chlorophyll-a

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