Chemical Modification of Methyl Pyropheophorbide-d and Synthesis of Chlorophyllous Chlorin Derivatives

doi:10.6023/cjoc201207022

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2300-2308.DOI: 10.6023/cjoc201207022 Previous Articles Next Articles

Articles

焦脱镁叶绿酸-d甲酯的化学修饰与叶绿素类二氢卟吩衍生物的合成

王振^a, 杨泽^a, 刘洋^a, 徐希森^a, 祁彩霞^b, 王进军^a,b

a 烟台大学化学化工学院烟台 264005;
b 山东省黄金工程技术研究中心工业应用烟台 264005

收稿日期:2012-07-17 修回日期:2012-08-20 发布日期:2012-08-22
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
中匈政府间科技合作(No. 2008-333-4-32)和山东黄金工程技术研究中心(2011年度)资助项目.

Chemical Modification of Methyl Pyropheophorbide-d and Synthesis of Chlorophyllous Chlorin Derivatives

Wang Zhen^a, Yang Ze^a, Liu Yang^a, Xu Xisen^a, Qi Caixia^b, Wang Jinjun^a,b

a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005

Received:2012-07-17 Revised:2012-08-20 Published:2012-08-22
Supported by:
Project supported by the Project of Technology Cooperation between Covernments of China and Hungary (No. 2008-333-4-32) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).

Chlorophyllous degraded products are ideal synthetic precursors for the synthesis of photodynamic therapy drugs. To obtain chlorophyllous photosensitizer, methyl pyropheophorbide-d was used as starting material, and its formyl and carbonyl groups on E-ring were modified by allomerization, Knoevenagel reaction, Hener reaction, Tiffeneau-Demjano rearrangement, Friedlaender condensation and reduction to build different chemical structures at 3-position and exocyclic E-ring. A series of chlorins with basic skeleton of chlorophyll were synthesized, and the relations between the molecular structures and their UV-Vis spectra were discussed. The possible mechanisms about corresponding reactions were tentatively proposed. The structures of new-reported chlorophyll derivatives were characterized by UV, IR, ¹H NMR and elemental analysis.

Key words: chlorophyll-a, chlorin, methyl pyropheophorbide-d, chemical modification

Cite this article

Wang Zhen, Yang Ze, Liu Yang, Xu Xisen, Qi Caixia, Wang Jinjun. Chemical Modification of Methyl Pyropheophorbide-d and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chin. J. Org. Chem., 2012, 32(12): 2300-2308.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Lash, T. D. J. Porphyrins Phthalocyanines 2011, 15, 1093.
(b) Washington, I.; Zhou, J.-L.; Jockusch, S.; Turro, N. J.; Nakanishi, K.; Sparrowb, J. R. Photochem. Photobiol. Sci. 2007, 6, 775.
[2] (a) Kozyrev, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, P. K. J. Org. Chem. 2006, 71, 1949.
(b) Hynninen, P. H.; Hyvärinen, K. H. J. Org. Chem. 2002, 67, 4055.
[3] (a) Springer, J. W.; Faries, K. M.; Diers, J. R.; Muthiah, C.; Mass, O.; Kee, H. L.; Kirmaier, C.; Jonathan, S.; Lindsey, J. S.; Bocian, D. F.; Dewey Holten, D. Photochem. Photobiol. 2012, 88, 651.
(b) Washington, I.; Brooks, C.; Turro, N. J.; Nakanishi, K. J. Am. Chem. Soc. 2004, 126(32), 9893.
[4] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese).
(王进军, 有机化学, 2005, 25, 1353.)
[5] (a) Goswami, L. N.; Ethirajan, M.; Dobhal, M. P.; Zhang, M.; Missert, J. R.; Shibata, M.; Kadish, K. M.; Pandey, R. K. J. Org. Chem. 2009, 74, 568.
(b) Kunieda, M.; Tamiaki, H. J. Org. Chem. 2008, 73, 7686.
(c) Jinadasa, R. G. W.; Hu, X,-K.; Vicente, M. G.; Smith, K. M. J. Med. Chem. 2011, 54, 7464.
(d) Wu, J.; Yin, J.-G.; Liu, R.-R.; Yang, Z.; Wang, Z.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 149 (in Chinese).
(武进, 殷军港, 刘冉冉, 杨泽, 王振, 王进军, 有机化学, 2012, 32, 149.)
[6] (a) Li, J.-Z.; Wang, J.-J.; Yoon, I.; Cui, B.-C.; Shim, Y. K. Bioorg. Med. Chem. Lett. 2012, 22, 1846.
(b) Yin, J.-G.; Wang, Z.; Yang, Z.; Liu, C.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 360 (in Chinese).
(殷军港, 王振, 杨泽, 刘超, 王进军, 有机化学, 2012, 32, 360.)
[7] (a) Sasaki, S.; Yoshizato, M.; Kunieda, M.; Tamiaki, H. Eur. J. Org. Chem. 2010, 5287.
(b) Dougherty, T. J.; Sumlin, A. B.; Greco, W. R.; Weishaupt, K. R.; Vaughan, L. A.; Pandey, R. K. Photochem. Photobiol. 2002, 76(1), 97.
(c) Battersby, A. R. Nat. Prod. Rep. 2000, 17, 507.
[8] Wang, P. M.S. Thesis, Yantai University, Yantai, 2009 (in Chinese).
(王朋, 硕士论文, 烟台大学, 烟台, 2009.)
[9] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[10] Wang, J.-J.; Han, G.-F.; Wu, X.-R.; Shim, Y.-J. Chin. J. Org. Chem. 2005, 25, 101 (in Chinese).
(王进军, 韩光范, 邬旭然, 沈荣基, 有机化学, 2005, 25, 101. )
[11] Han, G.-F.; Wang, J.-J.; Xu, Y.; Shim, Y.-J. Chin. J. Org. Chem. 2006, 26, 43 (in Chinese).
(韩光范, 王进军, 瞿燕, 沈荣基, 有机化学, 2006, 26, 43.)
[12] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40(4), 393.
[13] Wang, J. J.; Ji, J. Y.; Han, G.-F.; Wu, X.-R.; Wang, L.-M.; Shin, R. K. Acta Chim. Sinica 2004, 62(3), 302 (in Chinese).
(王进军, 纪建业, 韩光范, 邬旭然, 王鲁敏, 沈荣基, 化学学报, 2006, 62(3), 302.)
[14] (a) Tamiaki, H.; Kouraba, M. Tetrahedron 1997, 53, 10677.
(b) Wang, J.-J.; Wu, X.-R.; Han, G.-F.; Shim, R.-K. Chin. J. Org. Chem. 2005, 25, 313 (in Chinese).
(王进军, 邬旭然, 韩光范, 沈荣基, 有机化学, 2005, 25, 313.)
[15] Zhang, P. M.S. Thesis, Yantai University, Yantai, 2010 (in Chinese).
(张朋, 硕士论文, 烟台大学, 烟台, 2010.)

焦脱镁叶绿酸-d甲酯的化学修饰与叶绿素类二氢卟吩衍生物的合成

Chemical Modification of Methyl Pyropheophorbide-d and Synthesis of Chlorophyllous Chlorin Derivatives

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jiantao Zhang, Cong Zhang, Nuolin Mo, Jiating Luo, Lianfen Chen, Weibing Liu. Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3098-3106.
[2]	Fen Huang, Weiwei Luo, Jun Zhou. Research Progress of Polychloroalkylation Based on C—H Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2368-2390.
[3]	Na Gao, Xiaohui Chu, Yang Liu, Jiazhu Li, Jinjun Wang. Regio- and Stereoselective Aryl(aroyl)methylenenation of Pyropheophorbide and Syntheses of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1111-1122.
[4]	Yun Zhao, Yanfang Li, Rongxiao Li, Yaqing Wang, Xiaoxia Fan. A New Fluorescent Probe for Hypochlorous Acid Based on Chlorinium Ions Recognition Mechanism and Its Bioimaging Research in Living Cells [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1974-1981.
[5]	Zhu Zhang, Yu Zhao, Xinyue Wang, Jiazhu Li, Jinjun Wang. Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1177-1186.
[6]	Yaoxin Wang, Chen Cui, Xiaohui Yang. Recent Advances in Hydrochlorination of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3808-3815.
[7]	Zhang Zhu, Li Jiazhu, Wang Xinyue, Ma Jihua, Wang Xu, Wang Jinjun. Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2895-2903.
[8]	Zhu Ye, Huang Jinwen, Yang Xianjin. Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide [J]. Chin. J. Org. Chem., 2019, 39(6): 1665-1671.
[9]	Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source [J]. Chin. J. Org. Chem., 2019, 39(5): 1396-1403.
[10]	Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source [J]. Chin. J. Org. Chem., 2018, 38(6): 1454-1461.
[11]	Zhang Zhu, Li Jiazhu, Zhang Shanguo, Wang Zhen, Wang Jinjun. Heterocyclization for the Structures on the Periphery of Py-ropheophorbide and Synthesis of Chlorophyll Derivatives [J]. Chin. J. Org. Chem., 2018, 38(12): 3250-3259.
[12]	Zhang Zhu, Xu Xisen, Li Yanlong, Li Jiazhu, Wang Jinjun. Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives [J]. Chin. J. Org. Chem., 2018, 38(11): 2993-3001.
[13]	Liu Lifen, Zhang Xiao, Xie Xin, Li Ruihan, Gao Congjie. Modification of Polyimide-Urethane Reverse Osimosis Composite Membrane Based on NaA Zeolite [J]. Chin. J. Org. Chem., 2018, 38(11): 3127-3136.
[14]	Jiang Qiyong, Zhang Zhu, Liu Yang, Yao Nannan, Wang Jinjun. Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein [J]. Chin. J. Org. Chem., 2017, 37(7): 1814-1823.
[15]	Ren Shaobo, Zhang Haifeng, Zhang Jian, Zhang Wei, Liu Yunkui. Dichlorinating Reaction of N-Chlorosuccinimide with Isonitriles for the Synthesis of N-Phenyldichloroimides [J]. Chin. J. Org. Chem., 2016, 36(8): 1954-1957.