Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc201410047

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1294-1301.DOI: 10.6023/cjoc201410047 Previous Articles Next Articles

Articles

脱镁叶绿酸的C(17)-尾端酯基的化学反应及其二氢卟吩衍生物的合成

李晶华^a, 程建军^a, 张朋^c, 武进^c, 金英学^a, 王进军^b,c

a 哈尔滨师范大学化学化工学院哈尔滨 150025;
b 烟台大学文经学院烟台 264005;
c 烟台大学化学化工学院烟台 264005

收稿日期:2014-10-31 修回日期:2015-01-20 发布日期:2015-02-02
通讯作者: 金英学 E-mail:wjj1955@163.com
基金资助:
国家自然科学基金(No. 21272048)和山东省黄金工程技术研究中心(2011年度)资助项目.

Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives

Li Jinghua^a, Cheng Jianjun^a, Zhang Peng^c, Wu Jin^c, Jin Yingxue^a, Wang Jinjun^b,c

a College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025;
b Wenjing College, Yantai University, Yantai 264005;
c College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2014-10-31 Revised:2015-01-20 Published:2015-02-02
Supported by:
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).

1. Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives.PDF(1990KB)

Abstract

Pyropheophorbide-a methyl ester was used as a starting material. The active reaction regions were constructed by chemical modifications on the five-membered exocyclic ring, and the interconnections through different carbon chain between 13²- and 17-position were carried out by classic reaction, such as intramolecular interesterification, Michael addition and Claisen condensation, to form bicyclic or spirocyclic structures in the side of C-D ring. The aminolysis and acylation were performed making use of chemical activity of end ester group at 17-position to establish the different chemical structures in the far end of chlorin chromophore. The syntheses of 9 unreported chlorins related to chlorophyll with novel carbon skeleton were accomplished and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

Key words: chlorophyll-a, pyropheophorbide, chlorin, chemical reaction, synthesis

Cite this article

Li Jinghua, Cheng Jianjun, Zhang Peng, Wu Jin, Jin Yingxue, Wang Jinjun. Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives[J]. Chin. J. Org. Chem., 2015, 35(6): 1294-1301.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Gupta, A.; Goswansi, L. N.; Ethirajana, M.; Missert, J.; Ohulchanskyy, T. Y.; Roy, I.; Morgan, J.; Prasad, P. N.; Pandey, R. K. J. Porphyrins Phthalocyanines 2011, 15, 1.
[2] (a) Jamesl, N. S.; Ohulchanskyy, T. Y.; Chen, Y.-H.; Joshi, P.; Zheng, X.; Goswami, L.; Pandey, R. K. Theranastics 2013, 3(9), 703. (b) Srivatsan, A.; Ethirajan, M.; Pandey, S. K.; Dubey, S.; Zheng, X.; Liu, T.-H.; Shibata, M.; Missert, J.; Morgan, J.; Pandey, R. K. Mol. Pharmaceutics 2011, 8, 1186.
[3] (a) Ethirajan, M.; Joshi, P.; William, W. H.; Ohkubo, K.; Fukuzumi, S.; Pandey, R. K. Org. Lett. 2011, 8, 1956. (b) Li, J.-Z.; Wang, J.-J.; Yoon, L.; Cui, B.-C.; Shim, Y.-K. Bioorg. Med. Chem. Lett. 2012, 22, 1846. (c) Wang, J. J.; Liu, C.-L.; Li, J.-J. Synth. Commun. 2012, 42, 487. (d) 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.)
[4] (a) Chen, Y. H.; Li, G. L.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105. (b) Joshi, P.; Ethirajan, M.; Goswami, L. N.; Srivatsan, A.; Missert, J. R.; Pandey, R. K. J. Org. Chem. 2011, 76, 8629. (c) Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
[5] (a) Mennenga, A.; Wolfgang Gartner, W.; Lubitz, W.; Gorner, H. Phys. Chem. Chem. Phys. 2006, 8, 5444. (b) Wang, J. J.; Li, J.-J.; Wu, X.-R.; Shim, Y.-K. Chin. J. Chem. 2006, 24, 933. (c) 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, 74, 568.
[6] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
[7] (a) Sasaki, S.; Tamiaki, H. Tetrahedron. Lett. 2006, 47, 4965. (b) Mironov, A. F.; Efremov, A. V.; Efremova, O. A.; Bonnett, R. J. Chem. Soc., Perkin trans. 1 1998, 3601.
[8] (a) Kunieda, M.; Mizoguchi, T.; Tamiaki, H. Tetradehedron 2004, 60, 11349. (b) Wang, J.-J.; Han, G.-F.; Wu, X.-R.; Shin, R.-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.)
[9] (a) Wang, J. J.; Wang, P.; Li, J.-J.; Jakus, J.; Shim, Y.-K. Bull. Korean Chem. Soc. 2011, 32, 3473. (b) Yu, S.-S.; Xu, X.-S.; Liu, Y.; Li, J.-Z.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34. 362 (in Chinese). (于沙沙, 徐希森, 刘洋, 李家柱, 金英学, 祁彩霞, 王进军, 有机化学, 2014, 34, 362.) (c) Ji, J.-Y.; Yin, J.-G.; Zhang, Q.; Liu, C.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34. 2047 (in Chinese). 纪建业, 殷军港, 张千, 刘超, 王进军, 有机化学, 2014, 34, 2047.)
[10] Ma, L.; Dolphin, D. J. Org. Chem. 1996, 61, 2501.
[11] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[12] Wang, J.-J.; Zhao, Y.; Wu, X.-R.; Han, G.-F.; Shim, Y.-K. Chin. J. Org. Chem. 2002, 22, 565 (in Chinese). (王进军, 赵岩, 邬旭然, 韩光范, 沈荣基, 有机化学, 2002, 22, 565.)

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[6]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[7]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[8]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[9]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[10]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[11]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[12]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Jiantao Zhang, Cong Zhang, Nuolin Mo, Jiating Luo, Lianfen Chen, Weibing Liu. Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3098-3106.
[15]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.

脱镁叶绿酸的C(17)-尾端酯基的化学反应及其二氢卟吩衍生物的合成

Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments