Structure Transformations on the Groups Linked with C-Pyrrol Subring of Pheophorbide-a and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc201503050

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1929-1938.DOI: 10.6023/cjoc201503050 Previous Articles Next Articles

Articles

脱镁叶绿酸-aC-吡咯子环连带基团的结构转换及其叶绿素类二氢卟吩衍生物的合成

张珠^a, 姜齐永^a, 张千^b, 武进^b, 王进军^a,b

a 烟台大学文经学院食品与生物工程系烟台 264005;
b 烟台大学化学化工学院烟台 264005

收稿日期:2015-03-31 修回日期:2015-05-15 发布日期:2015-05-26
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
国家自然科学基金(No. 21272048)资助项目.

Structure Transformations on the Groups Linked with C-Pyrrol Subring of Pheophorbide-a and Synthesis of Chlorin Derivatives

Zhang Zhu^a, Jiang Qiyong^a, Zhang Qian^b, Wu Jin^b, Wang Jinjun^a,b

a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2015-03-31 Revised:2015-05-15 Published:2015-05-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272048).

1. Structure Transformations on the Groups Linked with C-Pyrrol Subring of Pheophorbide-a and Synthesis of Chlorin Derivatives.PDF(1328KB)

Abstract

Methyl pheophorbide-a ester was used as starting material, and the chemical reactions, including allomerization, aldol condensation with formaldehyde, nucleophilic addition on the cycloketone, Tiffeneau-demjanov rearrangement with diazomethane, were carried out making use of active reaction regions linked with C-pyrrol subring to establish different carbonyl structures on the exocyclic ring and 12-position. From these new-formed active groups, the novel structures such as nitrogenous heterocycle and spirocycle were formed by condensations with o-phenylenediamine or o-aminobenzaldehyde, 1,3-dipolar cycloaddition with formaldehyde and sarcosine, and other structure transformations. A series of unreported chlorins related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

Key words: chlorophyll-a, chlorin, C-pyrrol subring, chemical modification, synthesis

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Chen, Y. H.; Li, G. L.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105.(b) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese).(王进军, 有机化学, 2005, 25, 1353.)
[2] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
[3] (a) Liu, C.; Dobhal, M. P.; Ethirajan, M.; Missert, J. R.; Pandey, R. K.; Balasubramanian, S.; Sukumaran, D. K.; Zhang, M.; Kadish, K. M.; Ohkubo, K.; Fukuzumi, S. J. Am. Chem. Soc. 2008, 130, 14311.(b) Machida, S.; Isoda, Y.; Kunieda, M.; Tamiaki, H. Tetrahedron Lett. 2012, 53, 6277.(c) Fajer, J. Photosynth. Res. 2004, 80, 165.(d) Bruckner, C.; McCarthy, J. R.; Daniell, H. W.; Pendon, Z. D.; Iiagan, R. P.; Francis, T. M.; Ren, L.; Birge, R. R.; Frank, H. A. Chem. Phys. 2003, 294, 285.
[4] (a) Gil, M.; Bieniaszl, M.; Seshadri, M.; Fisher, D.; Ciesielski, M. J.; Chen, Y.; Pandey, R. K.; Kozbor, D. Brit. J. Cancer 2011, 103(10), 1.(b) Ethirajan, M.; Joshi, P.; William, W. H.; Ohkubo, K.; Fukuzumi, S.; Pandey, R. K. Org. Lett. 2011, 8, 1956 (c) Bellnier, D. A.; Greco, W. R.; Loewen, G. M.; Nava, H.; Oseroff, A. R.; Pandey, R. K.; Tsuchida, T.; Dougherty, T. J. Cancer Res. 2003, 63, 1806.(d) Wang, J.-J.; Li, J.-Z.; Jakus. J.; Shim, Y. K. J. Porphyrins Phthalocyanines 2012, 16, 122
[5] Ethirajan, M.; Joshi, P.; William, W. H.; Ohkubo, K.; Fukuzumi, S.; Pandey, R. K. Org. Lett. 2011, 13, 1956.
[6] (a) Li, J.-Z.; Zhang, P.; Zhang, S.-G.; Yin, J.-G.; Wang, J.-J. Org. Biochem. 2015, 13, 1992.(b) Li, J.-Z.; Zhang, P.; Yao, N.-N.; Zhao, L.-L.; Wang, J.-J.; Shim, Y.-K. Tetrahedron Lett. 2014, 55, 1086.(c) Yang, X.-Y.; Zhang, S.-G.; Zhang, P.; Zhang, Q.; Wang, Z.; Jin, Y.-X.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2015, 35, 181 (in Chinese).(杨晓英, 张善国, 张朋, 张千, 王振, 金英学, 祁彩霞, 王进军, 有机化学, 2015, 35, 181.)
[7] (a) Xu, X.-S.; Yao, N-N.; Liu, Y.; Yin, J.-G.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 938 (in Chinese).(徐希森, 姚楠楠, 刘洋, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 938.)(b) Liu, Y.; Xu, X.-S.; Li, J.-Z.; Yin, J.-G.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 552 (in Chinese).(刘洋, 徐希森, 李家柱, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 552.)(c) Wang, J.-J.; Li, J.-Z.; Li, Y.-W.; Jakus, J.; Shim, Y.-K. J. Porphyrins Phthalocyanines 2010, 14, 859.
[8] (a) Wang, J.-J.; Wang, P.; Li, J.-Z.; Jakus, J.; Shin, Y.-K. Bull. Korean Chem. Soc. 2011, 32, 3473. (b) Wang, J.-J.; Yin, Y.-F.; Yang, Z. J. Iran Chem. Soc. 2013, 10, 583.(c) Wang, J-J.; Ji, J.-Y.; Han, G.F.; Wu, X.-R.; Wang, L.-M.; Shin, Y.-K. Acta Chim. Sinica 2004, 62, 302 (in Chinese).(王进军, 纪建业, 韩光范, 邬旭然, 王鲁敏, 沈荣基, 化学学报, 2004, 62, 302.)
[9] Zhang, Q. M.S. Thesis, Yantai University, Yantai, 2011 (in Chinese). (张千, 硕士论文, 烟台大学, 烟台, 2011.)
[10] (a) Ma, L.; Dolphin, D. J. Org. Chem. 1996, 61, 2501.(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, 姚楠楠, 刘洋, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 1138.)(c) Smith, K. M.; Bissert, G. M. F.; Bushell, M. J. J. Org. Chem. 1980, 45, 2218.(d) Zhang, P. M.S. Thesis, Yantai University, Yantai, 2010 (in Chinese). (张朋, 硕士论文, 烟台大学, 烟台, 2010.)
[11] Liu, Y. M.S. Thesis, Yantai University, Yantai, 2014 (in Chinese). (刘洋, 硕士论文, 烟台大学, 烟台, 2014.)
[12] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[5]	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.
[6]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[13]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[14]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[15]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.

脱镁叶绿酸-aC-吡咯子环连带基团的结构转换及其叶绿素类二氢卟吩衍生物的合成

Structure Transformations on the Groups Linked with C-Pyrrol Subring of Pheophorbide-a and Synthesis of Chlorin Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments