SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 >Issue 03: 544 - 551

DOI: https://doi.org/10.6023/cjoc1105231

Articles

Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives

  • Liu Ranran ,
  • Yin Jungang ,
  • Li Jiazhu ,
  • Wu Jin ,
  • Chen Guanlong ,
  • Jin Yingxue ,
  • Wang Jinjun
Expand
  • a Colledge of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025

Received date: 2011-05-23

  Revised date: 2011-07-16

  Online 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)

Fold

Abstract

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)

Cite this article

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]. Chinese Journal of Organic Chemistry, 2012 , (03) : 544 -551 . DOI: 10.6023/cjoc1105231

References

[1] (a) Bellnier, D. A.; Greco, W. R.; Loewen, G. M.; Nava, H.;Oseroff, A. R.; Pandey, R. K.; Tsuchida, T.; Dougherty, T. J. CancerRes. 2003, 63, 1806.(b) Li, J.-J.; Wang, J.-J.; Yoon, I.; Cui, B.-C.; Shim, Y.-K. Bioorg.Med. Chem. Lett, 2012, 22, 1866.

[2] (a) Steruberg, E. D.; Dolphin, D. Tetrahedron 1998, 54, 4151.(b) Wu, J.; Yin, J.-G.; Zhang, Q.; Sun, C.-M.; Li, F.-G.; Pei. W.;Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1653 (in Chinese).(武进, 殷军港, 张千, 孙传民, 李付国, 王进军, 有机化学,2011, 31, 1653).(c) Wang, P.; Yang, Z.; Li, J.-Z.; Yao, N.-N.; Wang, J.-J. Chin. J.Org. Chem. 2012, 32, 368 (in Chinese).(王朋, 杨泽, 李家柱, 姚楠楠, 王进军, 有机化学, 2012, 32,368.)

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

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

[5] Zheng, G.; Potter, W. R.; Camacho, S. H.; Missert, J. R.; Wang,G.-C.; Bellnier, D. A.; Henderson, B. W.; Michael, H.; Rodgers, M.A. J.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2001, 44,1540.  

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

[7] Wang, J.-J.; Han, G.-F.; Wu, X.-Y.; Shim, Y.-K. 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.)

[8] Wang, J.-J.; Li, J.-Z.; Wu, X.-R.; Shim, Y.-K. Chin. J. Chem. 2006,24, 933.

[9] Wang, J.-J.; Ji, J.-Y.; Jing, J.-R.; Li, J.-Z.; Han, G. F.; Shim, Y.-K.Chin. J. Org. Chem. 2006, 26, 470 (in Chinese).(王进军, 纪建业, 荆济荣, 李家柱, 韩光范, 沈荣基, 有机化学,2006, 26, 470.)

[10] (a) Wang, J.-J.; Wu, X.-R.; Shim, Y.-K. Chin. J. Chem. 2005, 23,76.(b) Liu, R.-R.; Wang, L.-M.; Yin, J.-G.; Wu, J.; Liu, C.; Zhang, P.;Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 318 (in Chinese).(刘冉冉, 王鲁敏, 殷军港, 武进, 刘超, 张朋, 王进军, 有机化学, 2012, 32, 318.)(c) Yin, J.-G.; Wu, X.-R.; Liu, C.-L.; Zhao, L.-L.; Jin, Y.-X.;Wang, J. J. Chin. J. Org. Chem. 2011, 31, 1870 (in Chinese).(殷军港, 邬旭然, 刘春林, 赵丽丽, 金英学, 王进军, 有机化学,2011, 31, 1879.)

[11] Wang, J.-J.; Han, G.-F.; Wu, X.-R.; Wang, L.-M.; Shim, R.-J. Chin.J. Org. Chem. 2004, 24, 537 (in Chinese).(王进军, 韩光范, 邬旭然, 王鲁敏, 沈荣基, 有机化学, 2004,24, 537.)

[12] Tatar, J.; Stojanovic, M. B.; Stojanovic, M.; Markovic, R. TetrahedronLett. 2009, 50, 700.  
Options
Outlines

/

〈 〉