Synthesis of C-3-isoxazolyl Chlorins with Basic Skeleton of Chloro-phyll-a

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (12): 2074-2081. Previous Articles Next Articles

Full Papers

具有叶绿素基本碳架的C-3-异噁唑啉基二氢卟吩类衍生物的合成

王进军*，李韵伟，李家柱，殷军港

(烟台大学化学生物理工学院烟台 264005)

收稿日期:2010-12-19 修回日期:2011-01-06 发布日期:2011-07-28
通讯作者: 王进军 E-mail:wjj1955@163.com

Synthesis of C-3-isoxazolyl Chlorins with Basic Skeleton of Chloro-phyll-a

WANG Jin-Jun, LI Yun-Wei, LI Jia-Zhu, YIN Jun-Gang

(Science and Engineering College of Chemistry and Biology, Yantai University, Yantai 264005)

Received:2010-12-19 Revised:2011-01-06 Published:2011-07-28

Methyl pheophorbide-a was used as starting material, and C-3-isoxazolyl-substituted chlorins and other adducts were obtained by 1,3-dipolar cycloadditions of the vinyl group at 3-position with benzonitrile oxide and 4-nitrobenzonitrile oxide, respectively. The 3-isoxazolylpheophorbide-a was converted into rele-vant chlorin-p₆ derivative by the modification for the E-ring. The allomerization and rearrangement of the starting material produced purpurin-18 imide which was converted into title compound in desirable yield via same cycloaddition with 4-subatituted benzonitrile oxide. The structures of new chlorophyll derivatives were characterized by UV, IR, ¹H NMR spectra and elemental analysis. The possible mechanisms about corresponding oxidation, substitution and rearrangement reactions were tentatively proposed.

Key words: chlorophyll-a, methyl pheophorbide-a, C-3-isoxazolyl-chlorin, 1,3-dipolar cycloiddtion, photodynamic therapy (PDT)

Cite this article

WANG Jin-Jun, LI Yun-Wei, LI Jia-Zhu, YIN Jun-Gang. Synthesis of C-3-isoxazolyl Chlorins with Basic Skeleton of Chloro-phyll-a[J]. Chin. J. Org. Chem., 2011, 31(12): 2074-2081.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

References

1 (a) Shibata, R.; Tamiaki, H. Bioorg. Med. Chem. 2006; 14, 2235.

(b) Wang, J.-J.; Han, G.-F.; Wu, X.-Y.; Shim, Y.-K. Chin. J. Org. Chem. 2005, 25, 101 ( in Chinese ).

(王进军，韩光范，邬旭然，沈荣基，有机化学，2005, 25, 101. )

(c) Zhan, P.-Y.; Li, D.-F.; Wang, J.-J. Chin. J. Org. Chem. 2008, 28, 2039 ( in Chinese ).

(战佩英，李东风，王进军，有机化学，2008, 28, 2039. )

2 Pavlov, V. Y.; Ponomarev, G. V. Chem. Chem. Heterocycl. Compd, 2004, 40(4), 393-425.

3 Chen, Y.; Grvshuk, A.; Achilefu, S.; Ohulchansky, T.; Potter, W.; Zhong, T.; Morgan, J.; Chance, B.; Prasad, P. N.; Henderson, W.; Oseroff, A.; Pandey, R. K. Bioconjugate Chem, 2005, 16, 1264.

4 Coswami, L. H.; Ethiraian, M.; Dohbhal, M. P.; Zhang, M.; Missert, J. R.; Shibata, M.; Kadish, K. M.; Pandey, R. K. J. Org. Chem, 2009, 74, 568.

5 Sasaki, S.; Mizutani, K.; Kunieda, M.; Tamiaki, H. Tetrahedron Lett. 2008, 49, 4113

6 Wang, J.-J.; Zhang, P.; Wang, P. ; Chen, G.-L.; Li, F.-G.; Chin. J. Org. Chem. 2010, 30, 1192 ( in Chinese ).

(王进军，张朋，王朋，陈冠龙，李付国. 有机化学，2010, 30, 1192. )

7 Ji, J.-Y.; Li, J.-Z.; Wang, H.; Li, F.-G.; Hang, G.-F.; Shen, R.-J.; Wang, J.-J. Chin. J. Org. Chem. 2006, 26, 1714 ( in Chinese ).

(纪建业，李家柱，王虎，李付国，韩光范，沈荣基，王进军. 有机化学，2006, 26, 1714. )

8 Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.

9 Wang, J.-J.; Han, G.-F.; W, X.-R.; Wang, L.-M.; Shim, Y.-K. Chin. J. Org. Chem. 2004, 24, 537 ( in Chinese ).

(王进军，韩光范，邬旭然，王鲁敏，沈荣基，有机化学，2004, 24, 537 )

10 Li, J.-Z. M.S. Thesis, Yantai University, Yantai, 2007 (in Chinese.).

（李家柱，硕士论文，烟台大学，烟台，2007）.

11 Chen, Y.-H.; Li, G.-L.; Pandey, R. K. Curr. Org. Chem, 2004, 8, 1105.

12 Wang, J.-J.; Han, G.-F.; Wu, X.-R.; Shen, R.-J.; Chin. J. Org. Chem. 2005, 25, 101 ( in Chinese ).

(王进军，韩光范，邬旭然，沈荣基，有机化学，2005, 25, 101 )

[1]	Zhang Zhu, Li Jiazhu, Zhang Shanguo, Wang Zhen, Wang Jinjun. Heterocyclization for the Structures on the Periphery of Py-ropheophorbide and Synthesis of Chlorophyll Derivatives [J]. Chin. J. Org. Chem., 2018, 38(12): 3250-3259.
[2]	Zhang Zhu, Xu Xisen, Li Yanlong, Li Jiazhu, Wang Jinjun. Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives [J]. Chin. J. Org. Chem., 2018, 38(11): 2993-3001.
[3]	Li Yanlong, Li Jiazhu, Zhang Shanguo, Wang Jinjun. Synthesis of (Methylenated)vinylated Chlorophyllous Chlorins and Study on Their Photosensitive Bactericidal Activities [J]. Chin. J. Org. Chem., 2016, 36(3): 562-571.
[4]	Gao Na, Wang Zhen, Wu Jin, Liu Chao, Wang Jinjun. Synthesis of Cyanided Chlorophyllous Chlorin Derivatives and Study on Their Photodynamic Activities [J]. Chin. J. Org. Chem., 2016, 36(3): 580-589.
[5]	Zhang Zhu, Jiang Qiyong, Zhang Qian, Wu Jin, Wang Jinjun. Structure Transformations on the Groups Linked with C-Pyrrol Subring of Pheophorbide-a and Synthesis of Chlorin Derivatives [J]. Chin. J. Org. Chem., 2015, 35(9): 1929-1938.
[6]	Gao Na, Zhang Shanguo, Wang Zhen, Wang Jinjun. Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives [J]. Chin. J. Org. Chem., 2015, 35(8): 1715-1725.
[7]	Liu Hongyao, Zhu Guohua, Liu Ranran, Jin Yingxue,Qi Caixia, Wang Jinjun. Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives [J]. Chin. J. Org. Chem., 2015, 35(6): 1320-1329.
[8]	Zhang Shanguo, Li Jiazhu, Zhang Peng, Qi Caixia, Wang Jinjun. Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives [J]. Chin. J. Org. Chem., 2015, 35(5): 1060-1068.
[9]	Yang Xiaoying, Zhang Shanguo, Zhang Peng, Zhang Qian, Wang Zhen, Jin Yingxue, Qi Caixia, Wang Jinjun. Chemical Reactions of 13²-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives [J]. Chin. J. Org. Chem., 2015, 35(1): 181-190.
[10]	Ji Jianye, Xia Shangwen, Liu Yang, Yin Jungang, Qi Caixia, Wang Jinjun. Synthesis of Chlorophyllous Chlorin Derivatives Possessing Stereo-isomeric Character [J]. Chin. J. Org. Chem., 2014, 34(6): 1138-1147.
[11]	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.
[12]	Xu Xisen, Yao Nannan, Liu Yang, Yin Jungang, Qi Caixia, Wang Jinjun. Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives [J]. Chin. J. Org. Chem., 2014, 34(5): 938-947.
[13]	Liu Yang, Xu Xisen, Li Jiazhu, Yin Jungang, Qi Caixia, Wang Jinjun. Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives [J]. Chin. J. Org. Chem., 2014, 34(3): 552-560.
[14]	Yu Shasha, Xu Xisen, Liu Yang, Li Jiazhu, Jin Yingxue, Qi Caixia, Wang Jinjun. Synthesis of Chlorophyllous Chlorins Derivatives Substituted by Aromatic Groups on Their Periphery [J]. Chin. J. Org. Chem., 2014, 34(2): 362-370.
[15]	Ji Jianye, Yin Jungang, Zhao Lili, Yao Nannan, Qi Caixia, Wang Jinjun. Hydroxyla(acyla)tion of Purpurin-18 Imide and Synthesis of Chlorophyllous Chlorin Derivatives [J]. Chin. J. Org. Chem., 2014, 34(11): 2262-2271.

具有叶绿素基本碳架的C-3-异噁唑啉基二氢卟吩类衍生物的合成

Synthesis of C-3-isoxazolyl Chlorins with Basic Skeleton of Chloro-phyll-a

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments