Chinese Journal of Organic Chemistry >
Synthesis of (Methylenated)vinylated Chlorophyllous Chlorins and Study on Their Photosensitive Bactericidal Activities
Received date: 2015-08-31
Revised date: 2015-11-10
Online published: 2015-11-20
Supported by
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Resarch Centre of Gold Nanotechnology (2011).
Pheophorbide-a and b methyl esters, as initial degraded products from chlorophyll-a and b, were used as starting materials, and the hydroxylmethylic or formylic structures were established making use of the active reaction regions on chlorin periphery by some common reactions, such as aldol condensation, allomerization, oxidant oxidation. The methylene or vinyl groups possessing higher reactivity were introduced at different site around chlorin pericycle by Grignard reavtion, acid-catalyzed dehydration and rearrangement reaction in E-ring. A series of unreported chlorophyllous chlorins substituted by multi-terminal alkenyl group were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The in vitro photosensitive bactericidal activities of new chlorins were discussed and the possible mechanisms about corresponding reactions were tentatively proposed.
Li Yanlong , Li Jiazhu , Zhang Shanguo , Wang Jinjun . Synthesis of (Methylenated)vinylated Chlorophyllous Chlorins and Study on Their Photosensitive Bactericidal Activities[J]. Chinese Journal of Organic Chemistry, 2016 , 36(3) : 562 -571 . DOI: 10.6023/cjoc201508032
[1] Scheer, H. In Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, Vol. 1, Eds.: Grimm, B.; Porra, R. J.; Rüdiger, W.; Scheer, H, Springer, 2006, p. 1.
[2] Tsuchiya, T.; Mizoguchi, T.; Akimoto, S.; Tomo, T.; Tamiaki, H.; Mimuro, M. Plant Cell Physiol. 2012, 53(3), 518.
[3] (a) Hoober, J. K.; Eggink, L. L.; Chen, M. Photosynth. Res. 2007, 94, 387.
(b) Mizoguchi, T.; Shoji, A.; Kunieda, M.; Miyashita, H.; Tsuchiya, T.; Mimuro, M.; Tamiaki, H. Photochem. Photobiol. Sci. 2006, 5, 291.
[4] (a) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 ( in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
(b) Xu, X.-S.; Yao, N-N.; Liu, Y.; Yin, J.-G.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 938 (in Chinese). (徐希森, 姚楠楠, 刘洋, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 938.)
[5]
(c) Liu, Y.; Xu, X.-S.; Li, J.-Z.; Yin, J.-G.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 552 ( in Chinese). (刘洋, 徐希森, 李家柱, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 552.)
[6] (a) Chen, Y. H.; Li, G. L.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105.
(b) Morishita, H.; Tamiaki, H. Tetrahedron 2005, 61, 6097.
[7] Ji, J.-Y.; Xia, C.-W.; Liu, Y.; Yin, J.-G.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 1138 ( in Chinese). (纪建业, 夏尚文, 刘洋, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 1138.)
[8] (a) Bellnier, D. A.; Greco, W. R.; Loewen, G. M.; Nava, H.; Oseroff, A. R.; Pandey, R. K.; Tsuchida, T.; Dougherty, T. J. Cancer Res. 2003, 63.
(b) Wang, J.-J.; Li, J.-Z.; Li, Y.-W.; Jakus, J.; Shim, Y.-K. J. Porphyrins Phthalocyanines 2010, 14, 859.
(c) Wang, J.-J.; Li, J.-Z.; Jakus. J.; Shim, Y. K. J. Porphyrins Phthalocyanines 2012, 16, 122
[9] Ethirajan, M.; Chen, Y.-H.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011, 40, 340.
[10] Kozyrev, R. K.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71. 1949
[11] Li, J.-Z.; Zhang, P.; Zhang, S.-G.; Yin, J.-G.; Wang, J.-J. Org. Biol. Chem. 2015, 13, 1992.
[12] (a) Wainwringht, M.; Phoenix, D. A.; Marland, J. FEMS Immunol. Med. Microbiol. 1997, 19(1), 75.
(b) Wilson, M.; Burns, T.; Pratten, J. J. Appl. Bacteriol. 1995, 78, 569.
[13] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[14] 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, 裴文, 王进军, 有机化学, 2011, 31, 1653.)
[15] Yin, J.-G.; Wang, Z.; Yang, Z.; Liu, C.; Zhao, L.-L.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 360 ( in Chinese). (殷军港, 王振, 杨泽, 刘超, 赵丽丽, 王进军, 有机化学, 2012, 32, 360.)
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