Synthesis of Methyl Pyripheophorbide-a Substituted at 3-Position by Benzo-heterocycle with Nitrogen Atom

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (8): 906-911. Previous Articles Next Articles

3-位苯并含氮杂环取代的焦脱镁叶绿酸-a甲酯的合成

王进军^*,a, 邬旭然^a, 王鲁敏^a, 韩光范^b, 沈荣基^c

^a烟台大学应用化学系烟台 264005
^b华中船舶工业学院材料与工程学院镇江 212003
^c仁济大学微工程学院釜山韩国

收稿日期:2003-10-08 修回日期:2004-02-20 接受日期:2004-02-20 发布日期:2022-09-20
通讯作者: * E-mail: wjj1955@163.com
基金资助:
科技部中韩政府间合作项目(No. 2002)资助项目.

Synthesis of Methyl Pyripheophorbide-a Substituted at 3-Position by Benzo-heterocycle with Nitrogen Atom

WANG Jin-Jun^*,a, WU Xu-Ran^a, WANG Lu-Min^a, HAN Guang-Fan^b, SHIM Yong Key^c

^aDepartment of Applied Chemistry, Yantai University, Yantai 264005
^bSchool of Materials Science and Engineering, East China Shipbulding Institute, Zhenjiang 212003
^cSchool of Nano Engineering, Inji University, Pusan, Korea

Received:2003-10-08 Revised:2004-02-20 Accepted:2004-02-20 Published:2022-09-20

Abstract

Methyl pyropheophorbide-a (MPP-a) (1) was usedas starting material for the synthesis of chlorin compounds. Zinc(II) methyl pyropheophorbide-a (2) was obtained by refluxing with zincacetate in CH₂Cl₂. The palladium-catalyzed coupling reaction of complex 2 with phenylmercuric chloride was carried out to give methyl 3_b-phenyl pyropheophorbide-a (3). The exocyclic ethyleniclinkage of 3 was oxidized with OsO₄ and TPAP/N-methylmorphline N-oxide to afford diketone (4). The condensation of 4 with o-phenylenediamine by TFA catalyzed to givemethyl 3-quinoxalynyl pyropheophorbide-a (5). MPP-a (1) was oxidized by OsO₄ and NaIO₄ to generate methylpyropheophorbide-d (MPP-d) (6). The one pot reaction of 6 with cyclohexadione and naphthylamine was completed to form methyl 3-benzoacridinyl pyropheophorbide-a (7). The structures of the compounds were characterized by elemental analysis, UV, IR and¹H NMR spectra.

Key words: chlorophyll-a, methyl pyropheophorbide-a, chlorin derivatives substituted with heterocycle, photo~dynamic therapy (PDT)

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WANG Jin-Jun, WU Xu-Ran, WANG Lu-Min, HAN Guang-Fan, SHIM Yong Key. Synthesis of Methyl Pyripheophorbide-a Substituted at 3-Position by Benzo-heterocycle with Nitrogen Atom[J]. Chinese Journal of Organic Chemistry, 2004, 24(8): 906-911.

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1 (a) Pandey, R. K.; Sumlin, A.; Shiau, F.-Y.; Dougherty,T.; Smith, K. M. Bioorg. Med. Chem. Lett. 1992, 2,491.
(b) Rungta, A.; Zhang, G.; Missert, J. R.; Potter, W. R.; Dougherty, T.; Pendey,R. K. Bioorg. Med. Chem. Lett. 2000, 10, 1643.
2 (a) Pendey, R. K.; Tsuchida, T.; Constantine, S.; Zheng,G.; Medforth, C.; Kozlyrev, A.; Mohammad, A.; Rodgers, M. A. J.; Smith, K. M.; Dougherty, T. J. Med. Chem. 1997, 40, 3370.
(b) Pendey, R. K.; Constantine, S.; Goff, D. A.; Kozyrev, A.; Dougherty, T.; Smith, K. M. Bioorg. Med. Chem. Lett. 1996, 6, 105.
(c) Pendey, R. K. J. Porphyrins Phthalocyanines 2000, 4, 368.
3 (a) Tamiaki, H. K.; Kouraba, M. Tetrahedron 1997, 53, 10577.
(b) Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
4 Zhang, G.; Aoudia, M.; Lee, D.; Roders, M. A.; Smith, K.M.; Dougherty, T. J.; Pandey, R. K. J. Chem. Soc., Perkin Trans.1 2003, 3113.
5 Wang, J.-J.; Zhao, Y.; Wu, X.-Y.; Han, G.-F.; Shen, R.-J. Chin. J. Org. Chem. 2002, 22(8), 565 (in Chinese).
(王进军, 赵岩, 邬旭然, 韩光范, 沈荣基, 有机化学, 2002, 22(8), 565.)
6 (a) Wang, J.-J.; Han, G.-F.; Yin, J.-G.; Wu, X.-R.; Zhao, Y.;Gong, B.-A.; Shim, R.-J. Acta Chim. Sinica 2003, 61(6), 907 (in Chinese).
(王进军, 韩光范, 殷军港, 邬旭然, 赵岩, 宫宝安, 沈荣基, 化学学报, 2003, 61(6), 907.)
(b) Wang, J. J.; Ji, J. Y.; Han, G. F.; Shim, Y. K.; Mori, A.; Hatsui, T. Chin. J. Org. Chem. 2004, 24(1), 53 (in Chinese).
(王进军, 纪建业, 韩光范, 沈荣基, 森章, 初井敏一, 有机化学, 2004, 24(1), 53.)
(c) Han, G. F.; Wang, J. J.; Chang, X. J. Chin. J. Org. Chem. 2004, 24(2), 187 (in Chinese).
(韩光范, 王进军, 常秀娟, 有机化学, 2004, 24(2), 187.)
7 Wang, J.-J.; Han, G.-F.; Yin, J.-G.; Wu, X.-R.; Zhao,Y.; Gong, B.-A.; Shim, Y.-K. Chin. J. Chem. 2003, 21, 674.
8 Tamiaki, H.; Amakawa, M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92.
9 (a) Pandey, R. K.; Isaac, M.; Donald, I. M.; Medforth, C.J.; Senge, M. O.; Dougherty, T. J.; Smith, K. M. J. Org. Chem. 1997, 62, 1463.
(b) Shiau, F. Y.; Pandey, R. K.; Rasaprasad, S.; Dougherty, T. J.; Smith, K. M.J. Org. Chem. 1990, 55, 2190.
10 Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421.
11 Han, G.-F.; Wang, J.-J.; Jiang, G.-J. Chin. J. Org. Chem.2003, 23(9), 1004 (in Chinese).
(韩光范, 王进军, 姜贵基, 有机化学, 2003, 23(9), 1004.)

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3-位苯并含氮杂环取代的焦脱镁叶绿酸-a甲酯的合成

Synthesis of Methyl Pyripheophorbide-a Substituted at 3-Position by Benzo-heterocycle with Nitrogen Atom

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