磷酰胺酯前药策略及ProTide技术在抗病毒药物研发中的应用

doi:10.3866/PKU.DXHX202004127

Abstract

Abstract:

Antiviral drug is a powerful weapon for humans to defeat the virus. The spread of 2019 novel coronavirus pneumonia (COVID-19) outbreak has a serious impact on the world. At the same time, it also makes people aware of the importance of antiviral drug development. This article reviews the application of the phosphoramidate prodrug strategy and the application of ProTide technology in the development of antiviral drugs. The synthesis methods of nucleoside-phosphoramidate prodrugs are introduced. The application of nucleoside-phosphoramidate in different antiviral drugs is also summarized. This review can provide a reference for the development of new antiviral drugs in the future.

Key words: Anti-virus drug discovery, Nucleoside-phosphoramidate prodrugs, ProTide technology

MSC2000:

Xiaobin Sun, Zhiwei Miao. Application of Phosphoramidate Prodrugs Strategies and ProTide Technology in Anti-Virus Drug Discovery[J].University Chemistry, 2020, 35(12): 35-43.

Figures/Tables 14

References 21

1	Schinazi, R. F.; Shi, J.; Whitaker, T. In Innovative Drug Synthesis; Li, J. J.; Johnson, D. S. Ed.; John Wiley & Sons Inc.: Hoboken, New Jersey, USA, 2016; p. 61.
2	Thornton P. J. ; Kadri H. ; Miccoli A. ; Mehellou Y. J. Med. Chem. 2016, 59, 10400. doi: 10.1021/acs.jmedchem.6b00523
3	Babusis D. ; Phan T. K. ; Lee W. A. ; Watkins W. J. ; Ray A. S. Mol. Pharm. 2013, 10, 459. doi: 10.1021/mp3002045
4	聂飚; 金传飞; 钟文和; 任青云; 张英俊; 张霁. 有机化学, 2017, 37, 2818.
5	Mehellou Y. ; Balzarini J. ; McGuigan C. ChemMedChem 2009, 4, 1779. doi: 10.1002/cmdc.200900289
6	Corson T. W. ; Crews C. M. Cell 2007, 130, 769. doi: 10.1016/j.cell.2007.08.021
7	Holshue M. L. ; DeBolt C. ; Lindquist S. ; Lofy K. H. ; Wiesman J. ; Bruce H. ; Spitters C. ; Ericson K. ; Wilkerson S. ; Tural A. ; et al N. Engl. J. Med. 2020, 382, 929. doi: 10.1056/NEJMoa2001191
8	Cho A. ; Saunders O. L. ; Butler T. ; Zhang L. J. ; Xu J. ; Vela J. E. ; Feng J. Y. ; Ray A. S. ; Kim C. U. Bioorg. Med. Chem. Lett. 2012, 22, 2705. doi: 10.1016/j.bmcl.2012.02.105
9	McGuigan C. ; Serpi M. ; Bibbo R. ; Roberts H. ; Hughes C. ; Caterson B. ; Gibert A. T. ; Verson C. R. A. J. Med. Chem. 2008, 51, 5807. doi: 10.1021/jm800594c
10	Maiti M. ; Persoons L. ; Andrei G. ; Snoeck R. ; Balzarini J. ; Herdewijn P. ChemMedChem 2013, 8, 985. doi: 10.1002/cmdc.201300035
11	Ross B. S. ; Reddy P. G. ; Zhang H. R. ; Rachakonda S. ; Sofia M. J. J. Org. Chem. 2011, 76, 8311. doi: 10.1021/jo201492m
12	蔡国伟.四氢噻吩螺吡唑酮类衍生物不对称合成和抗丙肝新药索非布韦绿色合成[D].天津:南开大学, 2016.
13	Tran K. ; Beutner G. L. ; Schmidt M. ; Janey J. ; Chen K. ; Ros-so V. ; Eastgate M. D. J. Org. Chem. 2015, 80, 4994. doi: 10.1021/acs.joc.5b00392
14	DiRocco D. A. ; Ji Y. N. ; Sherer E. C. ; Klapars A. ; Reibarkh M. ; Dropinski J. ; Mathew R. ; Maligres P. ; Hyde A. M. ; Limanto J. ; et al Science 2017, 356, 426. doi: 10.1126/science.aam7936
15	Warren T. K. ; Jordan R. ; Lo M. K. ; Ray A. S. ; Mackman R. L. ; Soloveva V. ; Siegel D. ; Perron M. ; Bannister R. ; Hui H. C. ; et al Nature 2016, 531, 381. doi: 10.1038/nature17180
16	Heim M. H. Nat. Rev. Immunol. 2013, 13, 535. doi: 10.1038/nri3463
17	Gardelli C. ; Attenni B. ; Donghi M. ; Meppen M. ; Pacini B. ; Harper S. ; Di Marco A. ; Fiore F. ; Giuliano C. ; Pucci V. ; et al Med. Chem. 2009, 52, 5394. doi: 10.1021/jm900447q
18	Osgerby L. ; Lai Y. C. ; Thornton P. J. ; Amalfitano J. ; Le Duff C. S. ; Jabeen I. ; Kadri H. ; Miccoli A. ; Tucker J. H. R. ; Muqit M. M. K. ; et al J. Med. Chem. 2017, 60, 3518. doi: 10.1021/acs.jmedchem.6b01897
19	Liu C. ; Dumbre S. G. ; Pannecouque C. ; Huang C. S. ; Ptak R. G. ; Murray M. G. ; De Jonghe S. ; Herdewijin P. J. Med. Chem. 2016, 59, 9513. doi: 10.1021/acs.jmedchem.6b01260
20	Velanguparackel W. ; Hamon N. ; Balzarini J. ; McGuigan C. ; Westwell A. D. Bioorg. Med. Chem. Lett. 2014, 24, 2240. doi: 10.1016/j.bmcl.2014.03.092
21	Derudas M. ; Carta D. ; Brancale A. ; Vanpouille C. ; Lisco A. ; Margolis L. ; Balzarini J. ; McGuigan C. J. Med. Chem. 2009, 52, 5520. doi: 10.1021/jm9007856

[1]	Zhuping Xiao, Qiuju Feng. Application of Electronic Density Distribution Analysis in Organic Chemistry Teaching for Developing Organic Chemistry Thinking [J]. University Chemistry, 0, (): 2106046-.
[2]	Qingwang Xue, Shuling Xu, Yuanfu Zhang, Debin Huang, Aifeng Li, Xia Li, Huaisheng Wang. Exploration on the Experimental Teaching Mode Based on Scientific Research Penetration from the Perspective of Ideological and Political Courses [J]. University Chemistry, 0, (): 2107046-.
[3]	Ningning Dong, Linqi Xu, Feng Xiong, Boyu Yan, Kun Li, Dongcai Guo. Design of a Comprehensive Experiment: Titanium Carbide MXenes Mediated In Situ Reduction for Label-Free and Visualized Sensing of Silver Ions [J]. University Chemistry, 0, (): 2111060-.
[4]	Hongwei Zhao, Jiameng Huai, Ze Wang, Xia Chen. Complexometric Titration for the Determination of Zno in Pharmaceutical Preparations: Application of Quantitative Chemical Analysis in Practice [J]. University Chemistry, 0, (): 2111067-.
[5]	Zhixiang Yao, Xin Ma, Jingqing Zhang, Yuting Su, Hui Su. Laboratory Teaching Practice of On-Line Analysis of Aspirin Synthesis Process [J]. University Chemistry, 0, (): 2111076-.
[6]	Jianghua Li, Juntao Tang, Mei Mei, Wansong Chen, Limiao Chen, Fa Zhou, Jianhan Huang, Younian Liu. Preparation and Flame Retardancy Test of Ammonium Polyphosphate: A Comprehensive Applied Chemistry Experiment [J]. University Chemistry, 0, (): 2112001-.
[7]	Lihua Jin, Lei Tian, Chaozhan Wang, Yan Li, Yanli Guo, Hongfang Zhang. The Application Exploitation of Integrating Mind-Mapping into TaskDriven Teaching Method in Analytical Chemistry Course [J]. University Chemistry, 0, (): 2112042-.
[8]	Peijuan Zhang, Bo Zhao, Fengyi He, Hanfei Luo, Qifei Shen, Dongfeng Dang. The Comprehensive Innovation Experiment for Undergraduate: Study on Aggregation-Induced Emission of Tetraphenylethylene and the Application in Fingerprint Imaging [J]. University Chemistry, 0, (): 2112045-.
[9]	Xiaoyan Li, Huaiyu Zhang, Lingpeng Meng, Yanli Zeng. Exploration and Practice of Mixed Online/Offline Teaching in Computational Chemistry Laboratory [J]. University Chemistry, 0, (): 2112054-.
[10]	Yuanfei Li, Xunfang Yang, Guiling Wang, Ying Guo, Xu Wang, Xinru Li, Yanxia Zhou, Ying Xie. Determination of Surface Tension Isotherm of Phospholipid Solution Using Wilhelmy Method [J]. University Chemistry, 0, (): 2201014-.
[11]	Yu Zhang, Tingting Ji, Xinyan Zhang, Chunhao Li, Shuai Wang. Comprehensive Experimental Design of Organic Chemistry Based on Scientific Research Infiltration: Preparation of an Anti-Counterfeiting Ink [J]. University Chemistry, 0, (): 2111080-.
[12]	Ya Wu, Rongmiao Fang, Dan Xue, Wenzhen Wang, Yefei Nan, Biyun Su, Jun Shi. Exploration and Practice of Chemistry Laboratory Skill Competition in Collaboration with Traditional Laboratory Teaching [J]. University Chemistry, 0, (): 2111083-.
[13]	Nan Zhang, Jianyang Zang, Gang Wang, Taihong Liu. Nonlinear Characterization and Related Photophysics of Two-Photon Absorption [J]. University Chemistry, 0, (): 2201037-.
[14]	Liang Shi, Honglan Qi, Lu Zhang, Chengxiao Zhang. Discussion on the Definition and Improving Strategies of Selectivity in Analytical Chemistry [J]. University Chemistry, 0, (): 2111012-.
[15]	Xiaoyun Hu, Ling Ma, Xinran Yin, Dan Chen, Zhongqiang Zhou, Daohong Zhang. Synthesis and Characterization of (2R,3R)-1,4-Dimethoxyl-1,1,4,4- tetraphenyl-2,3-butanediol: A Recommended Comprehensive Chemistry Experiment [J]. University Chemistry, 0, (): 2111036-.

Application of Phosphoramidate Prodrugs Strategies and ProTide Technology in Anti-Virus Drug Discovery

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 14

References 21

Related Articles 15

Metrics

Recommended 0