Citation: Guo Meichao, Kang Jinfeng, Hou Jiao, Zhang Qianqian, Yu Wenquan, Chang Junbiao. Synthesis and Anti-HBV Evaluation of 5-Halogenated 2'-Deoxy-2'-β-fluoro-4'-azido Pyrimidine Nucleosides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(1): 221-225. doi: 10.6023/cjoc201907054 shu

Synthesis and Anti-HBV Evaluation of 5-Halogenated 2'-Deoxy-2'-β-fluoro-4'-azido Pyrimidine Nucleosides

a.
College of Chemistry, Zhengzhou University, Zhengzhou 450001
b.
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, He'nan 453007

Corresponding author: Yu Wenquan, wenquan_yu@zzu.edu.cn Chang Junbiao, changjunbiao@zzu.edu.cn
Received Date: 30 July 2019
Revised Date: 9 September 2019
Available Online: 18 January 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 81773570, U1804283) and the Young Backbone Teachers Fund of Zhengzhou University (No. 2017ZDGGJS020)the National Natural Science Foundation of China U1804283the National Natural Science Foundation of China 81773570the Young Backbone Teachers Fund of Zhengzhou University 2017ZDGGJS020

Figures(1)

A series of 5-halogenated 2'-deoxy-2'-β-fluoro-4'-azido pyrimidine nucleosides were synthesized from m-chloro-benzoyl protected 2'-deoxy-2'-β-fluoro-4'-azido uridine via ammonium cerium nitrate (CAN)-mediated halogenation, activation by triazole, amination, and deprotection. In vitro biological evaluation demonstrated that 5-chloro (6a) and 5-iodo (6c) nucleoside derivatives possess potent anti-HBV (hepatitis B virus) activity with low cytotoxicity.
- 5-halogenated,
- pyrimidine nucleoside,
- synthesis,
- anti-HBV activity
1. [1]
  World Health Organization Hepatitis B (18 July 2018). https://www.who.int/en/news-room/fact-sheets/detail/hepatitis-b.(accessed on 25 June 2019).
2. [2]
  Hoofnagle, J. H.; di Bisceglie, A. M. New Engl. J. Med. 1997, 336, 347. doi: 10.1056/NEJM199701303360507
3. [3]
  Mailliard, M. E.; Gollan, J. L. Annu. Rev. Med. 2006, 57, 155. doi: 10.1146/annurev.med.57.121304.131422
4. [4]
  Liaw, Y. F.; Chu, C. M. Lancet 2009, 373, 582. doi: 10.1016/S0140-6736(09)60207-5
5. [5]
  Chang, J. EP 2177527, 2013; US 8835615, 2014[Chem. Abstr. 2008, 149, 32518].
6. [6]
  Wang, Q.; Hu, W.; Wang, S.; Pan, Z.; Tao, L.; Guo, X.; Qian, K.; Chen, C.-H.; Lee, K.-H.; Chang, J. Eur. J. Med. Chem. 2011, 46, 4178. doi: 10.1016/j.ejmech.2011.06.020
7. [7]
  Zheng, L.; Wang, Q.; Yang, X.; Guo, X.; Chen, L.; Tao, L.; Dong, L.; Li, Y.; An, H.; Yu, X.; Wang, Q.; Chang, J. Antivir. Ther. 2012, 17, 679. doi: 10.3851/IMP2094
8. [8]
  Zhou, Y.; Zhang, Y.; Yang, X.; Zhao, J.; Zheng, L.; Sun, C.; Jiang, J.; Yang, Q.; Wang, Q.; Chang, J. Antivir. Ther. 2012, 17, 1593. doi: 10.3851/IMP2292
9. [9]
  Yang, Q.; Kang, J.; Zheng, L.; Wang, X.-J.; Wan, N.; Wu, J.; Qiao, Y.; Niu, P.; Wang, S.-Q.; Peng, Y.; Wang, Q.; Yu, W.; Chang, J. J. Med. Chem. 2015, 58, 3693. doi: 10.1021/jm5012963
10. [10]
  Lv, Z.; He, W.; Tian, X.; Kang, J.; Liu, Y.; Peng, Y.; Zheng, L.; Wang, Q.; Yu, W.; Chang, J. Eur. J. Med. Chem. 2015, 101, 103. doi: 10.1016/j.ejmech.2015.06.030
11. [11]
  Asakura, J.; Robins, M. J. J. Org. Chem. 1990, 55, 4928. doi: 10.1021/jo00303a033
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
5. [5]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
6. [6]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
7. [7]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
8. [8]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
9. [9]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
10. [10]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
11. [11]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
12. [12]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
13. [13]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
14. [14]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
15. [15]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
16. [16]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
17. [17]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
18. [18]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
19. [19]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
20. [20]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1137)
HTML views(268)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142