Chinese Journal of Organic Chemistry >
Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein
Received date: 2016-10-31
Revised date: 2017-01-16
Online published: 2017-03-03
Supported by
Project supported by the National Natural Science Foundations of China (No.21272048) and the University Science and Technology Plan Projects of Shandong Province (No.J15LC51).
Pyropheophorbide-a (b) methyl esters were used as starting materials to form different chlorophyll degradation products by the modification of the exocyclic ring and the metallization of the chromophore. The new functional groups were introduced at 20-position via the Vilsmeier acylation and the Blanc hydroxymethylation. The active structures of chlorin peripheries were oxidized using osmium tetroxide, thaillum nitrate and air as oxidizing agent to introduce the formyl group and the formylmethyl group at 3-, 7-or 12-postion and on the exocyclic ring, respectively. A series of unreported chlorin aldehydes related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The reaction mechanisms on the hydroformylation for the chlorophyllous chlorins were discussed and the interactions of new compounds with bovine serum albumins were researched.
Jiang Qiyong , Zhang Zhu , Liu Yang , Yao Nannan , Wang Jinjun . Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein[J]. Chinese Journal of Organic Chemistry, 2017 , 37(7) : 1814 -1823 . DOI: 10.6023/cjoc201610045
[1] (a) Nyman, E. S.; Hynninen, P. H. J. Photochem. Photobiol. A 2004, 73, 1.
(b) Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
(c) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353(in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
(d) 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, 73, 568
[2] (a) Okamoto, Y.; Tamiaki, H. J. Photochem. Photobiol. A 2011, 209, 250.
(b) Li, J.; Liu, Y.; Xu, X.-S.; Li, Y.-L.; Zhang, S.-G.; Yoon, I.; Shim, Y.K.; Wang, J.-J.; Yin, J.-G. Org. Biomol. Chem. 2015, 13, 1992.
(c) Li, Y.-L.; Li, J.-Z.; Zhang, S.-G.; Wang, J.-J. Chin. J. Org. Chem. 2016, 36, 562(in Chinese). (李彦龙, 李家柱, 张善国, 王进军, 有机化学, 2016, 36, 562.)
(d) Li, J.; He, N.; Liu, Y.; Zhang, Z.; Zhang, X.; Han, X.; Gai, Y.; Liu, Y.; Yin, J.; Wang, J. Dyes Pigm. 2017, 146, 189.
[3] (a) Li, J.-Z.; Wang, J.-J.; Yoon, I.; Cui, B.-C.; Shim, Y. K. Bioorg. Med. Chem. Lett. 2012, 22, 1846.
(b) Liu, H.-Y.; Zhu, G.-H.; Liu, Y.-Y.; Jin, Y.-X.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2015, 35, 1320(in Chinese). (刘红瑶, 朱国华, 刘冉冉, 金英学, 祁彩霞, 王进军, 有机化学, 2015, 35, 1320.)
[4] Ali, H.; Vanlier, J. E. In Handbook of Porphyrin Science, Vol. 4, Eds.:Kadish, K. M.; Smith, K. M.; Guilard, R., World Scientific Publishing Company, Singapore, 2010, pp. 1~119.
[5] Ethirajan, M.; Patel, N. J.; Pandey, R. K. In Handbook of Porphyrin Science, Vol. 4, Eds.:Kadish, K. M.; Smith, K. M.; Guilard, R., World Scientific Publishing Company, Singapore, 2010, pp. 249~323.
[6] Wang, X. F.; Tamiaki, H. Energy Environ. Sci. 2010, 3, 94
[7] (a) 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, 1870.)
(b) 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, 金英学, 王进军, 有机化学, 2012, 32, 360.)
[8] (a) Wang, J.-J.; Shim, Y. K.; Jiang, G.-J.; Imafuku, K. J. Heterocycl. Chem. 2004, 41, 29.
(b) Wang, J.-J.; Li, J.-Z.; Wu, X.-R.; Shim, Y. K. Chin. J. Chem. 2006, 24, 933.
[9] (a) 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.)
(b) Ji, J.-Y.; Xia, S.-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.)
[10] Liu, Y. M.S. Thesis, Yantai University, Yantai, 2014(in Chinese). (刘洋, 硕士论文, 烟台大学, 烟台, 2014.)
[11] (a) Hu, X.-L.; Cui, S.-Y.; Liu, J.-Q. Spectrochim. Acta A 2010, 77, 548.
(b) Jia, F.-G.; Wang, W.-W.; Wang, J.; Yin, J.-G.; Liu, Y.-M.; Liu, Z.-B. Anal. Methods 2012, 4, 449.
[12] (a) Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
(b) Schenk, J.; Daessler, H. G. Pharmazie 1969, 24, 419.
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