1,3-Dipolar Cycloadditions of (Pyro)pheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

doi:10.6023/cjoc201403067

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2279-2287.DOI: 10.6023/cjoc201403067 Previous Articles Next Articles

(焦)脱镁叶绿酸-a的1,3-偶极环加成反应及其叶绿素类二氢卟吩的合成

杨晓英^a, 殷军港^b, 金英学^a, 祁彩霞^c, 王进军^b,c

a 哈尔滨师范大学化学化工学院哈尔滨 150025;
b 烟台大学化学化工学院烟台 264005;
c 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期:2014-03-31 修回日期:2014-06-05 发布日期:2014-07-11
通讯作者: 金英学;王进军,wjj1955@163.com 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.

1,3-Dipolar Cycloadditions of (Pyro)pheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

Yang Xiaoying^a, Yin Jungang^b, Jin Yingxue^a, Qi Caixia^c, Wang Jinjun^b,c

a College of Chemistry & Engineering, Harbin Normal University, Harbin 150025;
b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
c Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received:2014-03-31 Revised:2014-06-05 Published:2014-07-11
Supported by:
Project supported by the National Natural Science Foundations of China (No.21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (No.2011).

Pheophorbide-a methyl ester was used as a starting material, and new carbon-carbon double bonds were built on the chlorin chromophore by addition, condensation and allomerization. 1,3-Dipolar cycloadditions with different 1,3-dipols for the olefinic bonds at 3-position, 12-position and exocyclic E-ring were performed to synthesize a series of chlorophyllous chlorin derivatives substituted with five-membered heterocycle. The chemical structures of the unreported chlorins were characterized by UV-Vis, ¹H NMR, IR, MS and elemental analysis. The region selectivity of 1,3-dipolar cycloadditions and corresponding reaction mechanisms were also discussed.

Key words: chlorophyll-a, chlorin, 1,3-dipolar cycloaddition, region selectivity, synthesis

Cite this article

Yang Xiaoying, Yin Jungang, Jin Yingxue, Qi Caixia, Wang Jinjun. 1,3-Dipolar Cycloadditions of (Pyro)pheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chin. J. Org. Chem., 2014, 34(11): 2279-2287.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Gil, M.; Bieniaszl, M.; Seshadri, M.; Fisher, D.; Ciesielski, M. J.; Chen, Y.; Pandey, R. K.; Kozbor, D. British J. Cancer 2011, 103(10), 1. (b) Mizoguchi, T.; Kim, T.-Y.; Sawamura, S.; Tamiaki, H. J. Phys. Chem. B 2008, 112, 16759. (c) Pandey, S. K.; Gryshuk, A. L.; Sajjad, M.; Zheng, X.; Chen, Y.-H.; Abouzeid, J. M.; Charamisinau, I.; Nabi, H. A.; Oseroff, A.; Pandey, R. K. J. Med. Chem. 2005, 48, 6286.
[2] (a) Callot, H. J. In The Chlorophylls, Ed.: Scheer, H., CRC Press, Boca Raton, FL, 1991, p. 339. (b) Gryshuk, A. L.; Chen, Y.-H.; Potter, W.; Ohulchansky, T.; Oseroff, A.; Pandey, R. K. J. Med. Chem. 2006, 49, 1874. (c) Srivatsan, A.; Ethirajan, M.; Pandey, S. K.; Dubey, S.; Zheng, X.; Liu, T.-H.; Shibata, M.; Missert, J.; Morgan, J.; Pandey, R. K. Mol. Pharm. 2011, 8, 1186.
[3] (a) Gryshuk, A. L.; Graham, A.; Pandey, S. K.; Potter, W. R.; Missert, J. R.; Oseroff, A.; Dougherty1, T. J.; Pandey, R. K. Photochem. Photobiol. 2002, 76, 194. (b) Gryshuk, A.; Chen, Y.-H.; Goswami, L. N.; Pandey, S.; Missert, J. R.; Ohulchanskyy, T.; Potter, W.; Prasad, P. N.; Oseroff, A.; Pandey, R. K. J. Med. Chem. 2007, 50, 1754. (c) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese).(王进军, 有机化学, 2005, 25, 1353.)
[4] Wang, J.-J.; Li, J.-Z.; Li, Y.-W.; Jakus, J.; Shim, Y.-K. J. Porphyrins Phthalocyanines 2010, 14, 859.
[5] (a) Wang, J.J.; Liu, C.-L.; Li, J.-J. Synth. Commun. 2012, 42, 487. (b) 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.) (c) 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.) (d) Yang, Z.; Wang, Z.; Liu, Y.; Xu, X.-S.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2013, 33, 116 (in Chinese). (杨泽, 王振, 刘洋, 徐希森, 祁彩霞, 王进军, 有机化学, 2013, 33, 116.)
[6] (a) Li, J.-Z.; Wang, J.-J.; Yoon, L.; Cui, B.-C.; Shim, Y.-K. Bioorg. Med. Chem. Lett. 2012, 22, 1846. (b) Wang, J.-J.; Li, J.-Z.; Jakus, J.; Shin, K. J. Porphyrins Phthalocyanines 2012, 16, 122. (c) Wang, J.-J.; Yin, Y.-F.; Tang, Z. J. Iran Chem. Soc. 2013, 10, 583. (d) Li, J.-Z.; Zhang, P.; Yao, N.-N.; Zhao, L.-L.; Wang, J.-J.; Shim, Y.-K. Tetrahedon Lett. 2014, 55, 1086.
[7] (a) Liu, R.-R.; Yin, J.-G.; Li, J. Z.; Wu, J.; Chen, G,-L.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 544 (in Chinese).(刘冉冉, 殷军港, 李家柱, 武进, 金英学, 王进军, 有机化学, 2012, 32, 544.) (b) 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.) (c) Yin, Y.-F.; Zang, Q.; Liu, Y.; Xu, X.-S.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2013, 33. 581 (in Chinese). (殷一樊, 张千, 刘洋, 徐希森, 祁彩霞, 王进军, 有机化学, 2013, 33, 1457.)
[8] (a) Houk, K. N.; Sins, J.; Duck, R. E. J. Am. Chem. Soc. 1973, 95(22), 7287. (b) Houk, K. N.; Sins, J.; Watts, C. R. J. Am. Chem. Soc. 1973, 95(22), 7301.
[9] (a) Wu, X.-R.; Liu, C.; Yang, Z.; Yao, N.-N.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 632 (in Chinese). (邬旭然, 刘超, 杨泽, 姚楠楠, 王进军, 有机化学, 2012, 32, 632.) (b) Wang, P.; Yang, J.; Li, J.-Z.; Yao, N.-N.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 368 (in Chinese). (王朋, 杨泽, 李家柱, 姚楠楠, 王进军, 有机化学, 2012, 32, 368.) (c) 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.) (d) Yu, S.-S.; Xu, X.-S.; Lu, Y.; Li, J.-Z.; Jin, Y.-X.; Qi, C.-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, 552.)
[10] Wang, P. M.S. Thesis, Yantai University, Yantai, 2009 (in Chinese).(王朋, 硕士论文, 烟台大学, 烟台, 2009.)
[11] (a) Wang, L. M.; Wang, P.; Liu, C.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 1700 (in Chinese). (王鲁敏, 王朋, 刘超, 金英学, 王进军, 有机化学, 2012, 32, 1700.) (b) Andrei Kozyrev, A.; Ethirajan, M.; Chen, P.; Ohkubo, K.; Robinson, B. C.; Barkigia, K. M.; Fukuzumi, S.; Kadish, K. M.; Pandey, R. K. J. Org. Chem. 2012, 77, 10260. (c) Tamiaki, H.; Komada. J.; Kunieda, M.; Fukai, K.; Yoshitomi, T.; Harada, J.; Mizoguchi, T. Photosynth. Res. 2011, 107, 133.
[12] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[13] Li, J.-Z.; Liu, W.-H.; Li, F.-G.; Wang, J.-J.; Suo, Y.-R.; Liu, Y. J. Chin. J. Org. Chem. 2007, 27, 1594 (in Chinese). (李家柱, 刘万卉, 李付国, 王进军, 索有瑞, 刘永军, 有机化学, 2007, 27, 1594.)
[14] Yang, Z.; Wang, Z.; Xu, X.-S.; Liu, Y.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 2099 (in Chinese). (杨泽, 王振, 徐希森, 刘洋, 祁彩霞, 王进军, 有机化学, 2012, 32, 2099.)

[1]	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.
[2]	Fen Huang, Weiwei Luo, Jun Zhou. Research Progress of Polychloroalkylation Based on C—H Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2368-2390.
[3]	Na Gao, Xiaohui Chu, Yang Liu, Jiazhu Li, Jinjun Wang. Regio- and Stereoselective Aryl(aroyl)methylenenation of Pyropheophorbide and Syntheses of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1111-1122.
[4]	Yun Zhao, Yanfang Li, Rongxiao Li, Yaqing Wang, Xiaoxia Fan. A New Fluorescent Probe for Hypochlorous Acid Based on Chlorinium Ions Recognition Mechanism and Its Bioimaging Research in Living Cells [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1974-1981.
[5]	Zhu Zhang, Yu Zhao, Xinyue Wang, Jiazhu Li, Jinjun Wang. Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1177-1186.
[6]	Yaoxin Wang, Chen Cui, Xiaohui Yang. Recent Advances in Hydrochlorination of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3808-3815.
[7]	Zhang Zhu, Li Jiazhu, Wang Xinyue, Ma Jihua, Wang Xu, Wang Jinjun. Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2895-2903.
[8]	Zhu Ye, Huang Jinwen, Yang Xianjin. Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide [J]. Chin. J. Org. Chem., 2019, 39(6): 1665-1671.
[9]	Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source [J]. Chin. J. Org. Chem., 2019, 39(5): 1396-1403.
[10]	Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source [J]. Chin. J. Org. Chem., 2018, 38(6): 1454-1461.
[11]	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.
[12]	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.
[13]	Liu Lifen, Zhang Xiao, Xie Xin, Li Ruihan, Gao Congjie. Modification of Polyimide-Urethane Reverse Osimosis Composite Membrane Based on NaA Zeolite [J]. Chin. J. Org. Chem., 2018, 38(11): 3127-3136.
[14]	Jiang Qiyong, Zhang Zhu, Liu Yang, Yao Nannan, Wang Jinjun. Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein [J]. Chin. J. Org. Chem., 2017, 37(7): 1814-1823.
[15]	Ren Shaobo, Zhang Haifeng, Zhang Jian, Zhang Wei, Liu Yunkui. Dichlorinating Reaction of N-Chlorosuccinimide with Isonitriles for the Synthesis of N-Phenyldichloroimides [J]. Chin. J. Org. Chem., 2016, 36(8): 1954-1957.

(焦)脱镁叶绿酸-a的1,3-偶极环加成反应及其叶绿素类二氢卟吩的合成

1,3-Dipolar Cycloadditions of (Pyro)pheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments