Chinese Journal of Organic Chemistry >
Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a
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).
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.
Yang Xiaoying , Tan Guanghui , Qu Fengyu , Jin Yingxue , Wang Jinjun . Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1206 -1211 . DOI: 10.6023/cjoc201401009
[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.)
/
| 〈 |
|
〉 |
