Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a

doi:10.6023/cjoc201401009

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1206-1211.DOI: 10.6023/cjoc201401009 Previous Articles Next Articles

Notes

焦脱镁叶绿酸-a的苯腙和氨基酸席夫碱的合成

杨晓英^a, 谭广慧^a,b, 曲凤玉^a,b, 金英学^a, 王进军^c

a. 哈尔滨师范大学化学化工学院哈尔滨 150025;
b. 哈尔滨师范大学生命科学技术学院哈尔滨 150025;
c. 烟台大学化学化工学院烟台 264005

收稿日期:2014-01-08 修回日期:2014-02-11 发布日期:2014-03-10
通讯作者: 金英学, 王进军 E-mail:yenghak@hrbnu.edu.cn
基金资助:
国家自然科学基金（Nos. 21272048，21171045）和黑龙江省高效科技创新团队建设计划（No. 2011TD010）资助项目.

Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a

Yang Xiaoying^a, Tan Guanghui^a,b, Qu Fengyu^a,b, Jin Yingxue^a, Wang Jinjun^c

a. College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025;
b. College of Life Science and Biotechnology, Haerbin Normal University, Harbin 150025;
c. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2014-01-08 Revised:2014-02-11 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.

Key words: photodynamic therapy (PDT), methyl pyropheophorbide-a (Mppa), phenylhydrazone, amino acid, Schiff base, water-soluble

Cite this article

Yang Xiaoying, Tan Guanghui, Qu Fengyu, Jin Yingxue, Wang Jinjun. Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a[J]. Chin. J. Org. Chem., 2014, 34(6): 1206-1211.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.)

焦脱镁叶绿酸-a的苯腙和氨基酸席夫碱的合成

Synthesis of Phenylhydrazone and Amino acid Schiff Base of Pyropheophorbide-a

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Haoruo Shangguan, Ping Huang, Zhenya Dai, Ping Wang. Synthesis and Application of β-Thiolated Amino Acids [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3089-3097.
[2]	Zhangtao Zhou, Yang Wang, Bingxin Cheng, Weiping Ye. [RuCl(p-cymene)-(S)-BINAP]Cl Catalyzed Asymmetric Preparation of trans-3-Amino-bicyclo[2.2.2]octane-2-carboxylic Acid Ethyl Ester [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2961-2967.
[3]	Sifan Dong, Haolong Li, Yuan Qin, Shiming Fan, Shouxin Liu. Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2351-2367.
[4]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[5]	Na Li, Xiaofeng Tan, Qinglai Yang. Recent Progress on Strategies and Applications of Imaging for Intestinal Microflora [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1375-1386.
[6]	Jiayu Hu, Zhiqiang Zhu, Zongbo Xie, Zhanggao Le. Recent Advances in Visible-Light-Induced Decarboxylative Coupling Reactions of α-Amino Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 978-1001.
[7]	Xiaolong Zhao, Yuqing Li, Liangwu Guo, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. A Highly Selective and High-Contrast Colorimetric “Off-On” Chemosensor for Cu^2＋ Based on Boron-Dipyrromethene (BODIPY) Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3757-3765.
[8]	Ting Wang, Jingchao Chen, Lun Wang, Zheting Wang, Baomin Fan. Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3693-3703.
[9]	Nana Wang, Jingcheng Xu, Haibo Mei, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, Jianlin Han. Electrochemical Approaches for Preparation of Tailor-Made Amino Acids [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3034-3049.
[10]	Li Sheng, Haoling Gao, Xufeng Wu, Gang Fan, Pengcheng Liu. Rhodium/(2S,2'S,3S,3'S)-3,3'-Di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) Catalyzed Synthesis of (R)-3-tert-Butoxy-carbonylamino-4-(2,4,5-trifluorophenyl)butyric Acid by Asymmetric Reduction of Enamines [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2105-2111.
[11]	Yang Yunhan, Bao Qiulian, Luo Jianping, Yang Junli, Li Canhua, Wei Keke, Chuan Yongming, Yang Lijuan. Competitive Fluorescence Sensing for Paraquat Based on Methylene Blue/Water-Soluble Phosphate Salt Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1680-1688.
[12]	Wang Jing, Jin Zhaohui, Ma Rong, Hao Yinjian, Wang Yijun, Li Ningbo, Xu Xinhua. Efficient Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines Catalyzed by Novel Schiff Base Zirconium Lewis Acid [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 969-977.
[13]	Zhang Chenglu, Wang Huayu, Yu Xiangkun, Yang Jingyi, Li Chuanyin, Gong Rongqin, Song Fulu, Sun Yuedong. Synthesis of Amide Thioether Bridged 1,3-Selenazole and 1,2,4-Triazole Derivatives and Their Inhibitory Activity against Cell Division Cycle Phosphatase B (Cdc25B) [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 432-439.
[14]	Zhao Xiaolong, Li Na, Liu Fayu, Gao Chao, Feng Jiubiao, Liu Leping, Guan Xiaolin, Yan Na. Synthesis and Application of Water-Soluble Reaction-Based Boron-Dipyrromethene (BODIPY) Probes for Fluorescent Detection of Peroxynitrite with High Selectivity [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4339-4343.
[15]	Wei Liang, Xiao Lu, Hu Yuanzheng, Wang Zuofei, Tao Haiyan, Wang Chunjiang. Recent Advances in Metallated Azomethine Ylides for the Synthesis of Chiral Unnatural α-Amino Acids [J]. Chin. J. Org. Chem., 2019, 39(8): 2119-2130.