Citation: Nie Biao, Jin Chuanfei, Zhong Wenhe, Ren Qingyun, Zhang Yingjun, Zhang Ji. Application and Recent Progress of Phosphoramidate Prodrugs Strategies and ProTide Technology in Drug Discovery[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2818-2840. doi: 10.6023/cjoc201705022 shu

Application and Recent Progress of Phosphoramidate Prodrugs Strategies and ProTide Technology in Drug Discovery

Nie Biao ^a ,
Jin Chuanfei ^a ,
Zhong Wenhe ^a ,
Ren Qingyun ^a ,
Zhang Yingjun ^a,b ,
Zhang Ji ^a,b,,

a.
State Key Laboratory of Anti-infective Drug Development, Dongguan 523871
b.
HEC Pharm Group, HEC R&D Center, Dongguan 523871

Corresponding author: Zhang Ji, zhangji@hecpharm.com
Received Date: 16 May 2017
Revised Date: 20 June 2017
Available Online: 14 November 2017
Fund Project: Project supported by the Introduction of Innovative R&D Team Program of Guangdong Province (No. 201301Y0105381261) and the State Key Laboratory of Anti-Infective Drug Development (Sunshine Lake Pharma Co. Ltd) (No. 2015DQ780357)the Introduction of Innovative R&D Team Program of Guangdong Province 201301Y0105381261the State Key Laboratory of Anti-Infective Drug Development (Sunshine Lake Pharma Co. Ltd) 2015DQ780357

Figures(41)

This review provides the brief history for the development and advances of ProTide strategies in the field of antiviral and anticancer pharmaceutical development. A summary is provided for the synthesis of nucleoside phosphoramidates, recent breakthroughs in the stereoselective assembly of chiral prodrugs and its application. This technology is extremely useful and has simplified innovative drug design of phosphorous-containing prodrugs. Simplifying such structural modification may create a new avenue of competition in the invention of new medicines from the parent drug.
- phosphoramidates,
- prodrugs,
- nucleoside and nucleotide,
- antiviral drug,
- phosphate and phosphonate,
- ProTide
1. [1]
  (a) Babusis, D.; Phan, T. K.; Lee, W. A.; Watkins, W. J.; Ray, A. S. Mol. Pharm. 2013, 10, 459.
  (b) Lee, W. A.; He, G. X.; Eisenberg, E.; Cihlar, T.; Swaminathan, S.; Mulato, A.; Cundy, K. C. Antimicrob. Agents. Chemother. 2005, 49, 1898.
  (c) Birkus, G.; Wang, R.; Liu, X. H.; Kutty, N.; MacArthur, H.; Cihlar, T.; Gibbs, C.; Swaminathan, S.; Lee, W.; McDermott, M. Antimicrob. Agents. Chemother. 2007, 51, 543.
2. [2]
  (a) Thornton, P. J.; Kadri, H.; Miccoli, A.; Mehellou, Y. J. Med. Chem. 2016, 59, 10400.
  (b) Jordheim, L. P.; Durantel, D.; Zoulim, F.; Dumontet, C. Nat. Rev. Drug Discovery 2013, 12, 447.
3. [3]
4. [4]
5. [5]
6. [6]
  Corson, T. W.; Crews, C. M. Cell 2007, 130, 769. doi: 10.1016/j.cell.2007.08.021
7. [7]
  Patil, S.; Lis, L. G.; Schumacher, R. J.; Norris, B. J.; Morgan, M. L.; Cuellar, R. A. D.; Blazar, B. R.; Suryanarayanan, R.; Gurvich, V. J.; Georg, G. I. J. Med. Chem. 2015, 58, 9334. doi: 10.1021/acs.jmedchem.5b01329
8. [8]
  Chassaing, C.; Berger, M.; Heckeroth, A.; Ilg, T.; Jaeger, M.; Kern, C.; Schmid, K.; Uphoff, M. J. Med. Chem. 2008, 51, 1111. doi: 10.1021/jm701456r
9. [9]
  Kleeb, S.; Jiang, X. H.; Frei, P.; Sigl, A.; Bezencon, J.; Bamberger, K.; Schwardt, O.; Ernst, B. J. Med. Chem. 2016, 59, 3163. doi: 10.1021/acs.jmedchem.5b01923
10. [10]
  Chowdhury, U. R.; Viker, K. B.; Stolz, K. L.; Holman, B. H.; Fautsch, M. P.; Dosa, P. I. J. Med. Chem. 2016, 59, 6221 doi: 10.1021/acs.jmedchem.6b00406
11. [11]
  Mehellou, Y. C. Chem. Med. Chem. 2016, 11, 1114. doi: 10.1002/cmdc.v11.11
12. [12]
  Pradere, U.; Garnier-Amblard, E. C.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2014, 114, 9154. doi: 10.1021/cr5002035
13. [13]
  (a) McGuigan, C.; Pathirana, R. N.; Mahmood, N.; Hay, A. J. Bioorg. Med. Chem. Lett. 1992, 2, 701.
  (b) Mehellou, Y.; Balzarini, J.; McGuigan, C. Chem. Med. Chem. 2009, 4, 1779.
14. [14]
  Cahard, D.; McGuigan, C.; Balzarini, J. Mini. Rev. Med. Chem. 2004, 4, 371.
15. [15]
  Maiti, M.; Persoons, L.; Andrei, G.; Snoeck, R.; Balzarini, J.; Herdewijn, P. Chem. Med. Chem. 2013, 8, 985 doi: 10.1002/cmdc.201300035
16. [16]
  Piplani, M.; Rana, A. C.; Sharma, P. C. J. Pharm. Pharm. Sci. 2016, 19, 82. doi: 10.18433/J3X61S
17. [17]
  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
18. [18]
  Zhou, L. H.; Zhang, H. W.; Tao, S. J.; Ehteshami, M.; Cho, J. H.; McBrayer, T. R.; Tharnish, P.; Whitaker, T.; Amblard, F.; Coats, S. J.; Schinazi, R. F. ACS Med. Chem. Lett. 2016, 7, 17. doi: 10.1021/acsmedchemlett.5b00402
19. [19]
  Lioux, T.; Mauny, M. A.; Lamoureux, A.; Bascoul, N.; Hays, M.; Vernejoul, F.; Baudru, A. S.; Boularan, C.; Lopes-Vicente, J.; Qushair, G.; Tiraby, G. J. Med. Chem. 2016, 59, 10253. doi: 10.1021/acs.jmedchem.6b01300
20. [20]
  Dabkowski, W.; Skrzypczynski, Z.; Michalski, J.; Piel, N.; McLaughlin, L. W.; Cramer, F. Nucleic Acids Res. 1984, 12, 9123. doi: 10.1093/nar/12.23.9123
21. [21]
  (a) McGuigan, C.; Harris, S. A.; Daluge, S. M.; Gudmundsson, K. S.; McLean, E. W.; Burnette, T. C.; Marr, H.; Hazen, R.; Condreay, L. D.; Johnson, L.; De Clercq, E.; Balzarini, J. J. Med. Chem. 2005, 48, 3504.
  (b) Sari, O.; Bassit, L.; Gavegnano, C.; McBrayer, T. R.; McCormick, L.; Cox, B.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Tetrahedron Lett. 2017, 58, 642.
  (c) Zhou, L. H.; Zhang, H. W.; Tao, S. J.; Ehteshami, M.; Cho, J. H.; McBrayer, T. R.; Tharnish, P.; Whitaker, T.; Amblard, F.; Coats, S. J.; Schinazi, R. F. ACS Med. Chem. Lett. 2016, 7, 17.
22. [22]
  Cho, A.; Zhang, L. J.; Xu, J.; Lee, R.; Butler, T.; Metobo, S.; Aktoudianakis, V.; Lew, W.; Ye, H.; Clarke, M.; Doerffler, E.; Byun, D.; Wang, T.; Babusis, D.; Carey, A. C.; German, P.; Sauer, D.; Zhong, W. D.; Rossi, S.; Fenaux, M.; McHutchison, J. G.; Perry, J.; Feng, J.; Ray, A. S.; Kim, C. U. J. Med. Chem. 2014, 57, 1812. doi: 10.1021/jm400201a
23. [23]
  (a) Kandil, S.; Balzarini, J.; Rat, S.; Brancale, A.; Westwell, A. D.; McGuigan, C. Bioorg. Med. Chem. Lett. 2016, 26, 5618.
  (b) Mehellou, Y.; McGuigan, C.; Brancale, A.; Balzarini, J. Bioorg. Med. Chem. Lett. 2007, 17, 3666.
24. [24]
  Mahmoud, S.; Li, H.; McBrayer, T. R.; Bassit, L.; Hammad, S. F.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Nucleosides Nucleotides Nucleic Acids 2007, 36, 66.
25. [25]
  Gudmundsson, K. S.; Daluge, S. M.; Johnson, L. C.; Jansen, R.; Hazen, R.; Condreay, L. D.; McGuigan, C. Nucleosides Nucleotides Nucleic Acids 2003, 22, 1953. doi: 10.1081/NCN-120025242
26. [26]
  Serpi, M.; Madela, K.; Pertusati, F.; Slusarczyk, M. Current Protocols in Nucleic Acid Chemistry, Wiley, New York, 2013, Chapter 15.
27. [27]
  Vanheusden, V.; Herdewijn, P.; Van Calenbergh, S. J. Pharm. Belg. 2002, 41.
28. [28]
  Gao, L. J.; De Jonghe, S.; Herdewijn, P. Org. Lett. 2016, 18, 5816. doi: 10.1021/acs.orglett.6b02764
29. [29]
  Simmons, B.; Liu, Z. Q.; Klapars, A.; Bellomo, A.; Silverman, S. M. Org. Lett. 2017, 19, 2218. doi: 10.1021/acs.orglett.7b00469
30. [30]
  Liu, C.; Dumbre, S. G.; Pannecouque, C.; Huang, C. S.; Ptak, R. G.; Murray, M. G.; De Jonghe, S.; Herdewijn, P. J. Med. Chem. 2016, 59, 9513. doi: 10.1021/acs.jmedchem.6b01260
31. [31]
  Pertusati, F.; Hinsinger, K.; Flynn, A. S.; Powell, N.; Tristram, A.; Balzarini, J.; McGuigan, C. Eur. J. Med. Chem. 2014, 78, 259. doi: 10.1016/j.ejmech.2014.03.051
32. [32]
  (a) Celewicz, L.; Jozwiak, A.; Ruszkowski, P.; Laskowska, H.; Olejnik, A.; Czarnecka, A.; Hoffmann, M.; Hladon, B. Bioorg. Med. Chem. 2011, 19, 6375.
  (b) Aliouane, L.; Rigaud, B.; Pfund, E.; Jean, L.; Renard, P. Y.; Lequeux, T. Tetrahedron Lett. 2011, 52, 259.
33. [33]
  Pertusati, F.; McGuigan, C. Chem. Commun. 2015, 51, 8070. doi: 10.1039/C5CC00448A
34. [34]
  Ross, B. S.; Reddy, P. G.; Zhang, H. R.; Rachakonda, S.; Sofia, M. J. J. Org. Chem. 2011, 76, 8311. doi: 10.1021/jo201492m
35. [35]
  Ryan, M.; Liu, T.; Dahlquist, F. W.; Griffith, O. H. Biochemistry 2001, 40, 9743. doi: 10.1021/bi010958m
36. [36]
  (a) Eastgate, M. D.; Schmidt, M. A.; Fandrick, K. R. Nat. Rev. Chem. 2017, 1, 0016, DOI: 10.1038/s41570-017-0016.
  (b) Tran, K.; Beutner, G. L.; Schmidt, M.; Janey, J.; Chen, K.; Rosso, V.; Eastgate, M. D. J. Org. Chem. 2015, 80, 4994.
37. [37]
  (a) Liu, S.; Zhang, Z. F.; Xie, F.; Butt, N. A.; Sun, L.; Zhang, W. B. Tetrahedron: Asymmetry 2012, 23, 329.
  (b) Zhang, Z. F.; Xie, F.; Jia, J.; Zhang, W. B. J. Am. Chem. Soc. 2010, 132, 15939.
38. [38]
  DiRocco, D. A.; Ji, Y. N.; Sherer, E. C.; Klapars, A.; Reibarkh, M.; Dropinski, J.; Mathew, R.; Maligres, P.; Hyde, A. M.; Limanto, J.; Brunskill, A.; Ruck, R. T.; Campeau, L.-C.; Davies, I. W. Science 2017, 356, 426. doi: 10.1126/science.aam7936
39. [39]
  McGuigan, C.; Murziani, P.; Slusarczyk, M.; Gonczy, B.; Vande Voorde, J.; Liekens, S.; Balzarini, J. J. Med. Chem. 2011, 54, 7247. doi: 10.1021/jm200815w
40. [40]
  McGuigan, C.; Madela, K.; Aljarah, M.; Gilles, A.; Brancale, A.; Zonta, N.; Chamberlain, S.; Vernachio, J.; Hutchins, J.; Hall, A.; Ames, B.; Gorovits, E.; Ganguly, B.; Kolykhalov, A.; Wang, J.; Muhammad, J.; Patti, J. M.; Henson, G. Bioorg. Med. Chem. Lett. 2010, 20, 4850. doi: 10.1016/j.bmcl.2010.06.094
41. [41]
  Bourdin, C.; McGuigan, C.; Brancale, A.; Chamberlain, S.; Vernachio, J.; Hutchins, J.; Gorovits, E.; Kolykhalov, A.; Muhammad, J.; Patti, J.; Henson, G.; Bleiman, B.; Bryant, K. D.; Ganguly, B.; Hunley, D.; Obikhod, A.; Walters, C. R.; Wang, J.; Ramamurty, C. V. S.; Battina, S. K.; Rao, C. S. Bioorg. Med. Chem. Lett. 2013, 23, 2260. doi: 10.1016/j.bmcl.2012.12.004
42. [42]
  Gardelli, C.; Attenni, B.; Donghi, M.; Meppen, M.; Pacini, B.; Harper, S.; Di Marco, A.; Fiore, F.; Giuliano, C.; Pucci, V.; Laufer, R.; Gennari, N.; Marcucci, I.; Leone, J. F.; Olsen, D. B.; MacCoss, M.; Rowley, M.; Narjes, F. J. Med. Chem. 2009, 52, 5394. doi: 10.1021/jm900447q
43. [43]
  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
44. [44]
  Slusarczyk, M.; Lopez, M. H.; Balzarini, J.; Mason, M.; Jiang, W. G.; Blagden, S.; Thompson, E.; Ghazaly, E.; McGuigan, C. J. Med. Chem. 2014, 57, 1531. doi: 10.1021/jm401853a
45. [45]
  Pertusati, F.; Hinsinger, K.; Flynn, A. S.; Powell, N.; Tristram, A.; Balzarini, J.; McGuigan, C. Eur. J. Med. Chem. 2014, 78, 259. doi: 10.1016/j.ejmech.2014.03.051
46. [46]
  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
47. [47]
  Toti, K. S.; Derudas, M.; Pertusati, F.; Sinnaeve, D.; Van den Broeck, F.; Margamuljana, L.; Martins, J. C.; Herdewijn, P.; Balzarini, J.; McGuigan, C.; Van Calenbergh, S. J. Org. Chem. 2014, 79, 5097. doi: 10.1021/jo500659e
48. [48]
  McGuigan, C.; Derudas, M.; Gonczy, B.; Hinsinger, K.; Kandil, S.; Pertusati, F.; Serpi, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; McHugh, T. D.; Maitra, A.; Akorli, E.; Evangelopoulos, D.; Bhakta, S. Bioorg. Med. Chem. 2014, 22, 2816. doi: 10.1016/j.bmc.2014.02.056
49. [49]
  Jonckers, T. H. M.; Tahri, A.; Vijgen, L.; Berke, J. M.; Lachau-Durand, S.; Stoops, B.; Snoeys, J.; Leclercq, L.; Tambuyzer, L.; Lin, T. I.; Simmen, K.; Raboisson, P. J. Med. Chem. 2016, 59, 5790. doi: 10.1021/acs.jmedchem.6b00382
50. [50]
  McGuigan, C.; Kelleher, M. R.; Perrone, P.; Mulready, S.; Luoni, G.; Daverio, F.; Rajyaguru, S.; Le Pogam, S.; Najera, I.; Martin, J. A.; Klumpp, K.; Smith, D. B. Bioorg. Med. Chem. Lett. 2009, 19, 4250. doi: 10.1016/j.bmcl.2009.05.099
51. [51]
  Derudas, M.; Brancale, A.; Naesens, L.; Neyts, J.; Balzarini, J.; McGuigan, C. Bioorg. Med. Chem. 2010, 18, 2748. doi: 10.1016/j.bmc.2010.02.015
52. [52]
  Derudas, M.; Quintiliani, M.; Brancale, A.; Andrei, G.; Snoeck, R.; Balzarini, J.; McGuigan, C. Antivir. Chem. Chemother. 2010, 21, 15. doi: 10.3851/IMP1661
53. [53]
  McGuigan, C.; Thiery, J. C.; Daverioa, F.; Jiang, W. G.; Davies, G.; Mason, M. Bioorg. Med. Chem. 2005, 13, 3219. doi: 10.1016/j.bmc.2005.02.041
54. [54]
  Siegel, D.; Hui, H. C.; Doerffler, E.; Clarke, M. O.; Chun, K.; Zhang, L. J.; Neville, S.; Carra, E.; Lew, W.; Ross, B.; Wang, Q.; Wolfe, L.; Jordan, R.; Soloveva, V.; Knox, J.; Perry, J.; Perron, M.; Stray, K. M.; Barauskas, O.; Feng, J. Y.; Xu, Y. L.; Lee, G.; Rheingold, A. L.; Ray, A. S.; Bannister, R.; Strickley, R.; Swa-minathan, S.; Lee, W. A.; Bavari, S.; Cihlar, T.; Lo, M. K.; Warren, T. K.; Mackman, R. L. J. Med. Chem. 2017, 60, 1648. doi: 10.1021/acs.jmedchem.6b01594
55. [55]
  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.; Larson, N.; Strickley, R.; Wells, J.; Stuthman, K. S.; Van Tongeren, S. A.; Garza, N. L.; Donnelly, G.; Shurtleff, A. C.; Retterer, C. J.; Gharaibeh, D.; Zamani, R.; Kenny, T.; Eaton, B. P.; Grimes, E.; Welch, L. S.; Gomba, L.; Wilhelmsen, C. L.; Nichols, D. K.; Nuss, J. E.; Nagle, E. R.; Kugelman, J. R.; Palacios, G.; Doerffler, E.; Neville, S.; Carra, E.; Clarke, M. O.; Zhang, L. J.; Lew, W.; Ross, B.; Wang, Q.; Chun, K.; Wolfe, L.; Babusis, D.; Park, Y.; Stray, K. M.; Trancheva, I.; Feng, J. Y.; Barauskas, O.; Xu, Y. L; Wong, P.; Braun, M. R.; Flint, M.; McMullan, L. K.; Chen, S. S.; Fearns, R.; Swaminathan, S.; Mayers, D. L.; Spiropoulou, C. F.; Lee, W. A.; Nichol, S. T.; Cihlar, T.; Bavari, S. Nature 2016, 531, 381. doi: 10.1038/nature17180
56. [56]
  Meneghesso, S.; Vanderlinden, E.; Brancale, A.; Balzarini, J.; Naesens, L.; McGuigan, C. Chem. Med. Chem. 2013, 8, 415. doi: 10.1002/cmdc.v8.3
57. [57]
  Kandil, S.; Balzarini, J.; Rat, S.; Brancale, A.; Westwell, A. D.; McGuigan, C. Bioorg. Med. Chem. Lett. 2016, 26, 5618. doi: 10.1016/j.bmcl.2016.10.077
58. [58]
  Mehellou, Y.; Valente, R.; Mottram, H.; Walsby, E.; Mills, K. I.; Balzarini, J.; McGuigan, C. Bioorg. Med. Chem. 2010, 18, 2439. doi: 10.1016/j.bmc.2010.02.059
59. [59]
  Meneghesso, S.; Vanderlinden, E.; Stevaert, A.; McGuigan, C.; Balzarini, J.; Naesens, L. Antivir. Res. 2012, 94, 35. doi: 10.1016/j.antiviral.2012.01.007
60. [60]
  McGuigan, C.; Bourdin, C.; Derudas, M.; Hamon, N.; Hinsinger, K.; Kandil, S.; Madela, K.; Meneghesso, S.; Pertusati, F.; Serpi, M.; Slusarczyk, M.; Chamberlain, S.; Kolykhalov, A.; Vernachio, J.; Vanpouille, C.; Introini, A.; Margolis, L.; Balzarini, J. Eur. J. Med. Chem. 2013, 70, 326. doi: 10.1016/j.ejmech.2013.09.047
61. [61]
  McGuigan, C.; Madela, K.; Aljarah, M.; Bourdin, C.; Arrica, M.; Barrett, E.; Jones, S.; Kolykhalov, A.; Bleiman, B.; Bryant, K. D.; Ganguly, B.; Gorovits, E.; Henson, G.; Hunley, D.; Hutchins, J.; Muhammad, J.; Obikhod, A.; Patti, J.; Walters, C. R.; Wang, J.; Vernachio, J.; Ramamurty, C. V. S.; Battina, S. K.; Chamberlain, S. J. Med. Chem. 2011, 54, 8632. doi: 10.1021/jm2011673
62. [62]
  Perrone, P.; Luoni, G. M.; Kelleher, M. R.; Daverio, F.; Angell, A.; Mulready, S.; Congiatu, C.; Rajyaguru, S.; Martin, J. A.; Leveque, V.; Pogam, S. L.; Najera, I.; Klumpp, K.; Smith, D. B.; McGuigan, C. J. Med. Chem. 2007, 50, 1840. doi: 10.1021/jm0613370
63. [63]
  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.; Mehellou, Y. J. Med. Chem. 2017, 60, 3518. doi: 10.1021/acs.jmedchem.6b01897
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  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142