Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives

doi:10.6023/cjoc201410003

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1320-1329.DOI: 10.6023/cjoc201410003 Previous Articles Next Articles

Articles

红紫素-18的化学修饰及其叶绿素类二氢卟吩衍生物的合成

刘红瑶^a, 朱国华^a, 刘冉冉^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 烟台大学文经学院烟台 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:2014-10-06 修回日期:2014-12-22 发布日期:2015-01-09
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)和山东省黄金工程技术研究中心(2011年度)资助项目.

Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives

Liu Hongyao^a, Zhu Guohua^a, Liu Ranran^b, Jin Yingxue ^a, Qi Caixia^c, Wang Jinjun^b,c

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

Received:2014-10-06 Revised:2014-12-22 Published:2015-01-09
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 (2011).

Purpurin-18 methyl ester and its imid ester were used as starting materials. The cycloaddition of the 3-vinyl group in purpurin-18 with nitril oxide or azomethine as 1,3-dipole was carried up to established different five-membered heterocyclic structures on the chlorin chromophore. Azadiene, prepared from the condensation of arylamine with aromatic aldehyde, with double bond at 3-position of purpurin-18 conducted hetero-Diels-Alder reaction (Povarov reaction) to generate ring-opening rearranged products substituted with aroyl or aralkyl group. The electrophilic substitution, allomerization and like-Aldol reaction were accomplished making use of the reactivity of C(12)-methyl or 20-meso-hydrogen to introduce various substitutes at 12- and 20-position on the periphery of purpurin-18. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra. The reaction mechanisms involved were also discussed accordingly.

Key words: chlorophyll-a, chlorin, purpurin-18, chemical reaction, synthesis

Cite this article

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.

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.) (c) 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.)
[2] (a) Kozyrev, A.; Ethirajan, M.; Chen, P.; Ohkubo, K.; Robinson, G. C.; Berkigia, K. M.; Fukuzumi, S.; Kadish, K. M.; Pandey, J. J. Org. Chem. 2012, 77, 10260. (b) Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393. (c) Kozyrey, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynaki, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949. (d) Liu, R.-R.; Wang, L.-M.; Yin, J.-G.; Wu, J.; Liu, C.; Zhang, P.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 318 (in Chinese). (刘冉冉, 王鲁敏, 金英学, 武进, 刘超, 王朋, 王进军, 有机化学, 2012, 32, 318.)
[3] (a) Wang, J.-J.; Yin, Y.-F.; Yang, Z. J. Iran. Chem. Soc. 2013, 10, 583. (b) 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.) (c) Yin, J.-G.; Li, Y.-W.; Li, J.-Z.; Zhang, Q.; Pei, W.; Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1213 (in Chinese). (殷军港, 李韵伟, 李家柱, 张千, 裴文, 王进军, 有机化学, 2011, 31, 1213.) (d) Li, J.-Z.; Wang, J.-J.; Yoon, L.; Cui, B.-C.; Shim, Y.-K. Bioorg. Med. Chem. Lett. 2012, 22, 1846. (e) Li, J.-Z.; Zhang, P.; Yao, N.-N.; Zhao, L.-L.; Wang, J.-J.; Shim, Y.-K. Tetrahedron Lett. 2014, 55, 1086
[4] (a) Wang, P.; Yang, Z.; 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.) (b) Grysshuk, A.; Chen, Y.; Goswami, L. N.; Pandey, S.; Missert, J. R.; Qhulchanskyy, T.; Potter, W.; Prasad, P. P.; Oseroff, A.; Pandey, R. K. J. Med. Chem. 2006, 49, 1874. (c) Pandey, S. K.; Sajjad, M.; Chen, Y.; Pandey, A.; Missert, J. R.; Batt, C.; Yao, R.; Nabi, H. A.; Oseroff, A. R.; Pandey, R. K. Bioconijuate Chem. 2009, 20, 274.
[5] Smith, C. D.; Gavrilyuk, J. I.; Lough, A. J.; Batey, R. A. J. Org. Chem. 2010, 75, 72.
[6] (a) Houk, K. N.; Sins, J.; Duck, R. E. J. Am. Chem. Soc. 1973, 95, 7287. (b) Houk, K. N.; Sins, J.; Watts, C. R. J. Am. Chem. Soc. 1973, 95, 7301.
[7] (a) Glusshkov, V. A.; Tolstikov, A. G. Russ. Chem. Rev. 2008, 77, 137. (b) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656.
[8] (a) Yu, S.-S.; Xu, X.-S.; Liu, 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, 362.) (b) Tamiaki, H.; Monobe, R.; Koizumi, S.; Miyatake, T.; Kinoshita, Y. Tetrahedron: Asymmerty 2013, 24, 966. (c) Srivatsan, A.; Wang, Y.-F.; Joshi, P.; Sajjad, M.; Chen, Y.-H.; Liu, C.; Thankcppan, K.; Missert, J. R.; Tracy, E.; Morgan, J.; Rigual, N.; Baumann, H.; Pandey, R. K. J. Med. Chem. 2011, 54, 6859. (d) Yin, Y.-F.; Zhang, 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, 581.)
[9] Wang, J.-J.; Wang, P.; Li, J.-Z.; Jakus, J.; Shin, Y.-K. Bull. Korean Chem. Soc. 2011, 32, 3473
[10] Liu, R.-R.; Wang, L.-M.; Yin, J.-G.; Wu, J.; Liu, C.; Zhang, P.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 318 (in Chinese). (刘冉冉, 王鲁敏, 殷军港, 武进, 刘超, 张朋, 王进军, 有机化学, 2012, 32, 318.)
[11] Liu, C. M.S. Thesis, Yantai University, Yantai, 2010 (in Chinese). (刘超, 硕士论文, 烟台大学, 烟台, 2010.)
[12] Han, G.-F.; Wang, J.-J.; Qu, Y.; Shin, Y.-K. Chin. J. Org. Chem. 2006, 26, 43 (in Chinese). (韩光范, 王进军, 瞿燕, 沈荣基, 有机化学, 2006, 26, 43.)

[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]	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.

红紫素-18的化学修饰及其叶绿素类二氢卟吩衍生物的合成

Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments