Application and Recent Progress of Phosphoramidate Prodrugs Strategies and ProTide Technology in Drug Discovery
- Corresponding author: Zhang Ji, zhangji@hecpharm.com
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
(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.
(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.
Corson, T. W.; Crews, C. M. Cell 2007, 130, 769.
doi: 10.1016/j.cell.2007.08.021
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
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
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
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
Mehellou, Y. C. Chem. Med. Chem. 2016, 11, 1114.
doi: 10.1002/cmdc.v11.11
Pradere, U.; Garnier-Amblard, E. C.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2014, 114, 9154.
doi: 10.1021/cr5002035
(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.
Cahard, D.; McGuigan, C.; Balzarini, J. Mini. Rev. Med. Chem. 2004, 4, 371.
Maiti, M.; Persoons, L.; Andrei, G.; Snoeck, R.; Balzarini, J.; Herdewijn, P. Chem. Med. Chem. 2013, 8, 985
doi: 10.1002/cmdc.201300035
Piplani, M.; Rana, A. C.; Sharma, P. C. J. Pharm. Pharm. Sci. 2016, 19, 82.
doi: 10.18433/J3X61S
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
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
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
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
(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.
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
(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.
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.
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
Serpi, M.; Madela, K.; Pertusati, F.; Slusarczyk, M. Current Protocols in Nucleic Acid Chemistry, Wiley, New York, 2013, Chapter 15.
Vanheusden, V.; Herdewijn, P.; Van Calenbergh, S. J. Pharm. Belg. 2002, 41.
Gao, L. J.; De Jonghe, S.; Herdewijn, P. Org. Lett. 2016, 18, 5816.
doi: 10.1021/acs.orglett.6b02764
Simmons, B.; Liu, Z. Q.; Klapars, A.; Bellomo, A.; Silverman, S. M. Org. Lett. 2017, 19, 2218.
doi: 10.1021/acs.orglett.7b00469
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
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
(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.
Pertusati, F.; McGuigan, C. Chem. Commun. 2015, 51, 8070.
doi: 10.1039/C5CC00448A
Ross, B. S.; Reddy, P. G.; Zhang, H. R.; Rachakonda, S.; Sofia, M. J. J. Org. Chem. 2011, 76, 8311.
doi: 10.1021/jo201492m
Ryan, M.; Liu, T.; Dahlquist, F. W.; Griffith, O. H. Biochemistry 2001, 40, 9743.
doi: 10.1021/bi010958m
(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.
(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.
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Derudas, M.; Quintiliani, M.; Brancale, A.; Andrei, G.; Snoeck, R.; Balzarini, J.; McGuigan, C. Antivir. Chem. Chemother. 2010, 21, 15.
doi: 10.3851/IMP1661
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
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
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
Meneghesso, S.; Vanderlinden, E.; Brancale, A.; Balzarini, J.; Naesens, L.; McGuigan, C. Chem. Med. Chem. 2013, 8, 415.
doi: 10.1002/cmdc.v8.3
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
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
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
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
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
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
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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Reagents and conditions: (a) dibenzyl N, N-dimethylphosphorami-dite, tetrazole, CH2Cl2, CH3CN; (b) 30% H2O2, THF, 0 ℃; (c) TMSBr, DCM; (d) ion exchange using Na+-Dowex resin
From International Workshop on Clinical Pharmacology of HIV & Hepatitis Therapy 2015, Washington, DC, Abst. # 6, J. M. Custodio et al., Gilead Science
Reagents and conditions: (a) POCl3, Et3N, anhydrous Et2O, -78 ℃ for 1 h, then r.t. 1 h; (b) phenyl or 1-naphthyl phosphorodichloridate, Et3N, anhydrous DCM, -78 ℃, 1 ~ 3 h; (c) t-BuMgCl or NMI, anhydrous THF, r.t. 16~18 h.
Reagents and conditions: (a) anhyd. CH2Cl2, HBr (33% in acetic acid, 6.7 equiv.), 0 ℃ to r.t., 2 h; anhyd. CH3CN, KOH (3.0 equiv.), TDA-1 (0.2 equiv.), r.t., 1 h; (b) anhyd. CH2Cl2, BCl3 (10 equiv.), -78 ℃, 2 h then-20 ℃, 2 h, 30 min; (c) anhyd. MeOH, NaOMe (3.0 equiv.), reflux, overnight; (d) anhyd. THF, t-BuMgCl (1.2 equiv.), naphthyl L-alanine ester phospho-chloridate (1.2 equiv.), r.t., overnight.
Reagents and conditions: (a) Et3N, DCM; (b) t-BuMgCl, dry THF; (c) acetone, pTsOH, 71%~87% yield; (d) t-BuMgCl, dry THF.
Reagent and conditions: (a) dimethylfornamide dimethyl acetal, anhydrous DMF, r.t., 1 d; (b) t-BuMgCl, THF, r.t., overnight or NMI, V(THF)/V(pyridine)=3/2, r.t., overnight; (c) 1-propanol, reflux, for 18 h or 2-propanol, reflux, 24~96 h.
Reagents and conditions: (a) octanoyl chloride, DIPEA, anhydrous CH2Cl2, 0 ℃ to 20℃, 2 h; (b) propargyloctanamide, Pd(PPh3)4, CuI, DIPEA, anhydrous DMF, 20 ℃; (c) 149, phosphorochlorides, NMI, anhydrous THF, 20 ℃, 12 h
Reagents and conditions: (a) Et3N (1 equiv.), POCl3 (1 equiv.), dry THF; (b) for symmetrical diamidates, amine (5 equiv.), Et3N (10 equiv.), dry DCM; for asymmetric diamidates, amine 1 (1 equiv.), Et3N (2 equiv.) then amine 2 (5 equiv.), Et3N (10 equiv.), dry DCM.