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2014 , Vol. 34 >Issue 6: 1206 - 1211

DOI: https://doi.org/10.6023/cjoc201401009

研究简报

焦脱镁叶绿酸-a的苯腙和氨基酸席夫碱的合成

  • 杨晓英 ,
  • 谭广慧 ,
  • 曲凤玉 ,
  • 金英学 ,
  • 王进军
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  • a. 哈尔滨师范大学化学化工学院 哈尔滨 150025;
    b. 哈尔滨师范大学生命科学技术学院 哈尔滨 150025;
    c. 烟台大学化学化工学院 烟台 264005

收稿日期: 2014-01-08

  修回日期: 2014-02-11

  网络出版日期: 2014-03-10

基金资助

国家自然科学基金（Nos. 21272048，21171045）和黑龙江省高效科技创新团队建设计划（No. 2011TD010）资助项目.

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Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a

  • Yang Xiaoying ,
  • Tan Guanghui ,
  • Qu Fengyu ,
  • Jin Yingxue ,
  • Wang Jinjun
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  • a. College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025;
    b. College of Life Science and Biotechnology, Haerbin Normal University, Harbin 150025;
    c. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received date: 2014-01-08

  Revised date: 2014-02-11

  Online published: 2014-03-10

Supported by

Project supported by the National Natural Sciences of Foundation of China (Nos. 21272048, 21171045), and the Program for Scientific Technological Innovation, Team Construction in Universites of Heilongjiang Province (No. 211TD010).

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摘要

以焦脱镁叶绿酸-a甲酯为原料，通过E-环羰基分别与苯肼和氨基酸反应合成了焦脱镁叶绿酸-a甲酯苯腙和焦脱镁叶绿酸-a氨基酸席夫碱. 苯腙的最大吸收波长显著红移. 席夫碱最大吸收波长稍有蓝移，而其水溶性明显增大. 所有新化合物的结构经1H NMR，MS或元素分析所证实.

关键词： 光动力治疗; 焦脱镁叶绿酸-a甲酯(Mppa); 苯腙; 氨基酸; 席夫碱; 水溶性

本文引用格式

杨晓英 , 谭广慧 , 曲凤玉 , 金英学 , 王进军 . 焦脱镁叶绿酸-a的苯腙和氨基酸席夫碱的合成[J]. 有机化学, 2014 , 34(6) : 1206 -1211 . DOI: 10.6023/cjoc201401009

Abstract

Methyl pyropheophorbide-a was used as starting material for the synthesis of phenylhydrazone and amino acid Schiff base by reactions of carbonyl group at 131-position. The maximum absorption wavelength of phenylhydrazone caused a red shift. The water-solubility of Schiff base was incremented, and the maximum absorption wavelength shifted hypsochromically. The structures of all these compounds were characterized by 1H NMR, MS and elemental analysis.

Key words： photodynamic therapy (PDT); methyl pyropheophorbide-a (Mppa); phenylhydrazone; amino acid; Schiff base; water-soluble

参考文献

[1] Betz, U. A. Drug Discovery Today 2005, 10, 1057.



[2] Hopkins, A. L.; Groom, C. R. Nat. Rev. Drug Discovery 2002, 1, 727.



[3] Kossodo, S.; Lamuraglia, G. M. Am. J. Cardiovasc. Drugs 2001, 1, 15.



[4] Dolmans, D. E.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380.



[5] Gurfinkel, M.; Thompson, A. B.; Ralston, W.; Troya, T. L.; Moore, L.; Moore, T. A.; Gust, J. D.; Tatman, D.; Reynolds, J. S.; Muggenburg, B.; Nilula, K.; Pandey, R.; Mayer, R. H.; Hawrysz, D. J.; Sevickmuraca, E. M. Photochem. Photobiol. 2000, 72, 94.



[6] Zheng, G.; Li, H..; Zhang, M.; Lund, K. S.; Chance, B.; Glickson, J. D. Bioconjugate Chem. 2002, 13, 392.



[7] Zheng, G.; Chen, Yu.; Intes, X.; Chance, B.; Glickson, J. D. J. Porphyrins Phthalocyanines 2004, 8, 1106.



[8] Mikhail, A. G..; Ivan, S. L.; Sergey, V. F.; Alexander, G. T.; Anton, A. S.; Anatoly, A. T.; Alexander, A. K.; Andery, F. M. Mendeleev Commun. 2007, 17, 209.



[9] (a) Tamiaki, H.; Takeuchi, S.; Tsudzuki, S.; Miyatake, T.; Tanikaga, R. Tetrahydron 1988, 54, 6699.



(b) Machida, S.; Isoda, Y.; Kunieda, M.; Tamiaki, H. Tetrahedron Lett. 2012, 53, 6277.



(c) Oba, T.; Uda, Y.; Matsuda, K.; Fukusumi, T.; Satoshi, I.; Hiratani, K.; Tamiaki, H. Bioorg. Med. Chem. Lett. 2011, 21, 2489.



(d) Gryshuk A. L.; Chen, Y. H.; Potter, W.; Ohulchansky, T.; Oseroff, A.; Pandey, R. K. J. Med. Chem. 2006, 49, 1874.



(e) Sasaki, S. I.; Yoshizato, M.; Kunieda, M.; Tamiaki, H. Eur. J. Org. Chem. 2010, 29, 5287.



(f) Liang, B. Y.; Liu, Y.; Xu, X.; Jin, Y. X.; Qi, C. X.; Wang, J. J. Chin. J. Org. Chem. 2013, 33, 2357.



(g) Yin, J. G.; Wang, Z.; Yang, Z.; Jin, Y. X.; Wang, J. J. Chin. J. Org. Chem. 2012, 32, 1936.



[10] (a) Ohkubo, K.; Kotani, H.; Shao, J. G.; Ou, Z. P.; Kadish, K. M.; Li, G. L.; Pandey, R. K.; Fujitsuka, M.; Ito, O.; Imahori, H.; Fukuzumi, S. Angew. Chem., Int. Ed. 2004, 43, 853.



(b) Liu, X.; Sternberg, E.; Dolphin, D. J. Org. Chem. 2008, 73, 6542.



[11] (a) Li, G.; Graham, A.; Chen, Y. H.; Dobhal, M. P.; Morgan, J.; Zheng, G.; Kozyrev, A.; Oseroff, A.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2003, 46, 5349.



(b) Li, G. L.; Dobhal, M. P.; Graham, A.; Shibata, M.; Zheng, G.; Kozyrev, A.; Pandey, R. K. J. Org. Chem. 2003, 68, 3762.



(c) Graham, A.; Li, G. L.; Chen, Y. H.; Morgan, J.; Oseroff1, A.; Dougherty, T. J.; Pandey. R. K. Photochem. Photobiol. 2003, 77, 561.



[12] (a) Ma, L. F.; Dolphin, D. Tetrahedron Lett. 1995, 36, 7791.



(b) Katterle, M.; Holzwarth, A. R.; Jesorka. A. Eur. J. Org. Chem. 2006, 25, 414.



(c) Kozyrev, A. N.; Thomas J. Dougherty, T. J.; Pandey, R. K. Chem. Commun. 1998, 34, 481.



(d) Liu, X.; Sternberg, E.; Dolphin, D. Chem. Commun. 2004, 40, 852.



(e) Mironov, A. F.; Grin, M. A.; Dzardanov, D. V.; Golovina, K. V.; Shim, Y. K. Mendeleev Commun. 2001, 11, 205.



(f) Grin, M. A.; Titeev, R. A.; Brittal, D. I.; Olga, V.; Ulybina, O. V.; Tsiprovskiy, A. G.; Berzina, M. Y.; Lobanova, I. A.; Sivaev, I. B.; VBregadze, V. I.; Mironov, A. F. Mendeleev Commun. 2011, 21, 84.



[13] (a) Kosaka, N.; Tamiaki, K. Eur. J. Org. Chem. 2004, 23, 2325.



(b) Chen, Y. H.; Gryshuk, A.; Achilefu, S.; Ohulchansky, T.; Potter, W.; Zhong, T. X.; Morgan, J.; Chance, B.; Prasad, P. N.; Henderson, B. W.; Oseroff, A.; Pandey, R. K. Bioconjugate Chem. 2005, 16, 1264.



(c) Chen, Y. H.; Zheng, X.; Dobhal, M. P.; Gryshuk, A.; Morgan, J.; Dougherty, T. J.; Oseroff, A.; Pandey, R. K. J. Med. Chem. 2005, 48, 3692.



[14] (a) Mettath, S.; Gang Zheng.; Zielinski, T. J.; Shibata, M.; Alderfer, J. L.; Dougherty, T. J.; Pandey, R. K. Tetrahedron Lett. 2000, 41, 6289.



(b) Mettath, S.; Li, G. L.; Srikrishnan, T.; Mehta, R.; Grossman, Z. D.; Dougherty, T. J.; Pandey, R. K. Org. Lett. 1999, 1, 1193.



[15] Wang, J.-J.; Ji, W.-Y.; Han, G.-F.; Wu, X.-R.; Wang, L. M.; Shen, R. J. Acta Chim. Sinica 2004, 62, 302 (in Chinese).



(王进军, 纪业伟, 韩光范, 邬旭冉, 王鲁敏, 沈荣基, 化学学报, 2004, 62, 302.)



[16] Pandey, R. K.; Tsuchida, T.; Constantine, S.; Zheng, G.; Medforth, C.; Kozyrev, A.; Molhammad, A.; Rodgers, M. A. J.; Smith, K. M.; Douherty, T. J. Med. Chem. 1997, 40, 3770.



[17] Pandey, R. K.; Sumlin, A.; Shiau, F.-Y.; Dougherty, T.; Smith, K. M. Bioorg. Med. Chem. Lett. 1992, 2, 491.



[18] Rungta, A.; Zheng, G.; Missert, J. R.; Potter, W. R.; Dougherty, T.; Pandey, R. K. Bioorg. Med. Chem. Lett. 2000, 10, 1463.



[19] (a) Wang, J.-J.; Li, J.-Z.; Li, Y.-W.; Jakus, J.; Shim, Y.-K. J. Porphyrins Phthalocyanines 2010, 14, 859.



(b) Wang, J.-J.; Li, Y.-W.; Li, J.-Z.; Yin, J.-G. Chin. J. Org. Chem. 2006, 26, 1714 ( in Chinese).



(王进军, 李韵伟, 李家柱, 殷军港, 有机化学, 2006, 26, 1714.)



(c) Wang, L.-M.; Wang, Z.; Yang. Z.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 2154 (in Chinese).



(王鲁敏, 王振, 杨泽, 金英学, 王进军, 有机化学, 2012, 32, 2154.)



(d) 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.)



(e) Ji, J.-Y.; Xia, S.-W.; Zhao, L.-L.; Li, J.-Z.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2013, 33, 1457 (in Chinese).



(纪建业, 夏尚文, 赵丽丽, 李家柱, 祁彩霞, 王进军, 有机化学, 2013, 33, 1457.)

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