K. C. Cundy, Clinical pharmacokinetics of the antiviral nucleotide analogues cidofovir and adefovir, Clin Pharmacokinet, vol.36, pp.127-143, 1999.

L. Naesens, R. Snoeck, and G. Andrei, HPMPC (cidofovir), PMEA (adefovir) and related acyclic nucleoside phosphonate analogues: a review of their pharmacology and clinical potential in the treatment of viral infections, Antivir Chem Chemother, vol.8, pp.1-23, 1997.

E. De-clercq, Antiviral drugs in current clinical use, J Clin Virol, vol.30, pp.115-133, 2004.

X. Z. Fu, S. H. Jiang, and C. Li, Design and synthesis of novel bis(L-amino acid) ester prodrugs of 9-2-(phosphonomethoxy)ethyl adenine (PMEA) with improved anti-HBV activity, Bioorg Med Chem Lett, vol.17, pp.465-470, 2007.

P. Lu, J. X. Liu, and Y. Y. Wang, Design, synthesis and evaluation of novel oxazaphosphorine prodrugs of 9-(2-phosphonomethoxyethyl)adenine (PMEA, adefovir) as potent HBV inhibitors, Bioorg Med Chem Lett, vol.19, pp.6918-6921, 2009.

F. Pertusati, K. Hinsinger, and A. S. Flynn, PMPA and PMEA prodrugs for the treatment of HIV infections and human papillomavirus (HPV) associated neoplasia and cancer, Eur J Med Chem, vol.78, pp.259-268, 2014.

A. Merta, I. Votruba, and I. Rosenberg, Inhibition of herpes-simplex virus-DNA polymerase by diphosphates of acyclic phosphonylmethoxyalkyl nucleotide analogs, Antiviral Res, vol.13, pp.209-218, 1990.

S. A. Foster, J. Cerny, and Y. C. Cheng, Herpes-simplex virusspecified DNA-polymerase is the target for the antiviral action, J Biol Chem, vol.9, issue.2, pp.238-244, 1991.

J. M. Cherrington, S. Allen, and N. Bischofberger, Kinetic interaction of the diphosphates of 9-(2-phosphonylmethoxyethyl)adenine and other anti-HIV active purine congeners with HIV reverse-transcriptase and human DNA polymerase-alpha, polymerase-beta and polymerase-gamma, Antivir Chem Chemother, vol.6, pp.217-221, 1995.

J. M. Cherrington, M. D. Fuller, and A. S. Mulato, Comparative kinetic analyses of interaction of inhibitors with rauscher murine leukemia virus and human immunodeficiency virus reverse transcriptases, Antimicrob Agents Chemother, vol.40, pp.1270-1273, 1996.

I. Votruba, M. Travnicek, and I. Rosenberg, Inhibition of avian-myeloblastosis virus reverse-transcriptase by diphosphates of acyclic phosphonylmethyl nucleotide analogs, Antiviral Res, vol.13, pp.287-293, 1990.

G. Birkus, I. Votruba, and A. Holy, 9-2-(phosphonomethoxy)ethyl adenine diphosphate (PMEApp) as a substrate toward replicative DNA polymerases alpha, delta, epsilon, and epsilon*, Biochem Pharmacol, vol.58, pp.487-492, 1999.

T. Cihlar and M. S. Chen, Incorporation of selected nucleoside phosphonates and anti-human immunodeficiency virus nucleotide analogues into DNA by human DNA polymerases alpha, beta and gamma, Antivir Chem Chemother, vol.8, pp.187-195, 1997.

P. Kramata, I. Votruba, and B. Otova, Different inhibitory potencies of acyclic phosphonomethoxyalkyl nucleotide analogs toward DNA polymerases alpha, delta, and epsilon, Mol Pharmacol, vol.49, pp.1005-1011, 1996.

P. Kramata, G. Birkus, and M. Otmar, Structural features of acyclic nucleotide analogs conferring inhibitory effects on cellular replicative DNA polymerases, Collect Czech Chem Commun, vol.61, pp.188-191, 1996.

A. A. Krayevsky, Molecular bases of drug design for AIDS treatment: achievements and prospects, Mol Biol, vol.33, pp.295-303, 1999.

A. Krayevsky, A. Arzumanov, and E. Shirokova, dNTP modified at triphosphate residues: substrate properties towards DNA polymerases and stability in human serum, Nucleosides Nucleotides, vol.17, pp.681-693, 1998.

. Holy and I. Rosenberg, -phosphonylmethoxyethyl)adenine and related-compounds, Collect Czech Chem Commun, vol.9, issue.2, pp.2801-2809, 1987.

C. E. Mckenna and P. D. Shen, Fluorination of methanediphosphonate esters by perchloryl fluoride -synthesis of fluoromethanediphosphonic acid and difluoromethanediphosphonic acid, J Org Chem, vol.46, pp.4573-4576, 1981.

C. E. Mckenna, L. A. Khawli, and W. Y. Ahmad, Synthesis of alpha-halogenated methanediphosphonates, Phosphorus Sulfur Silicon Relat Elem, vol.37, pp.1-12, 1988.

J. Boretto, S. Longhi, and J. M. Navarro, An integrated system to study multiply substituted human immunodeficiency virus type 1 reverse transcriptase, Anal Biochem, vol.292, pp.139-147, 2001.

B. Selmi, J. Boretto, and J. M. Navarro, The valine-tothreonine 75 substitution in human immunodeficiency virus type 1 reverse transcriptase and its relation with stavudine resistance, J Biol Chem, vol.276, pp.13965-13974, 2001.

J. G. Moffatt, General synthesis of nucleoside-5 triphosphates, Can J Chem, vol.42, pp.599-604, 1964.

J. G. Moffatt and H. G. Khorana, Nucleoside polyphosphates.10. The synthesis and some reactions of nucleoside-5' phosphoromorpholidates and related compounds. Improved methods for preparation of nucleoside-5' polyphosphates, J Am Chem Soc, vol.83, pp.649-658, 1961.

D. J. Burton and R. M. Flynn, Preparation of F-methylene bis phosphonates, J Fluorine Chem, vol.15, pp.263-266, 1980.

G. M. Blackburn, D. A. England, and F. Kolkmann, Monofluoro-methylenebisphosphonic and difluoromethylenebisphosphonic acids -isopolar analogs of pyrophosphoric acid, J Chem Soc Chem Commun, vol.15, pp.930-932, 1981.

D. W. Hutchinson and D. M. Thornton, A simple synthesis of monofluoromethylene bisphosphonic acid

, J Organomet Chem, vol.340, pp.93-99, 1988.

H. Dw and G. Semple, Synthesis of alkylated methylene bisphosphonates via organothallium intermediates, J Organomet Chem, vol.291, pp.145-151, 1985.

D. W. Hutchinson and G. Semple, The dehalogenation of dihalogenomethylenebisphosphonates, Phosphorus Sulfur Silicon Relat Elem, vol.21, pp.1-4, 1984.

D. Hebel, K. L. Kirk, and J. Kinjo, Synthesis of a difluoromethylenephosphonate analog of AZT-5'-triphosphate and its inhibition of HIV-1 reverse-transcriptase, Bioorg Med Chem Lett, vol.1, pp.357-360, 1991.

E. Differding and H. Ofner, N-Fluorobenzenesulfonimide -a practical reagent for electrophilic fluorinations, Synlett, pp.187-189, 1991.

R. S. Li, A. Muscate, and G. L. Kenyon, Synthesis, characterization, and inhibitory activities of nucleoside alpha, beta-imido triphosphate analogues on human immunodeficiency virus-1 reverse transcriptase, Bioorg Chem, vol.24, pp.251-261, 1996.

S. Priet, L. Roux, and M. Saez-ayala, Enzymatic synthesis of acyclic nucleoside thiophosphonate diphosphates: effect of the alpha-phosphorus configuration on HIV-1 RT activity, Antiviral Res, vol.117, pp.122-131, 2015.
URL : https://hal.archives-ouvertes.fr/hal-01439000

X. H. Liu, X. R. Zhang, and G. M. Blackburn, Synthesis of three novel supercharged beta, gamma-methylene analogues of adenosine triphosphate, Chem Commun, vol.1, pp.87-88, 1997.

G. M. Blackburn, K. De, and F. Kolkmann, The synthesis and metal-binding characteristics of novel, isopolar phosphonate analogs of nucleotides, J Chem Soc Perkin Trans, vol.1, pp.1119-1125, 1984.

G. M. Blackburn, K. De, and F. Kolkmann, 3 New beta, gamma-methylene analogs of adenosine-triphosphate, J Chem Soc Chem Commun, vol.22, pp.1188-1190, 1981.

L. Arabshahi, N. N. Khan, and M. Butler, Difluoromethylene)phosphates of guanine nucleosides as probes of DNA-polymerases and G-proteins, Biochemistry, vol.29, pp.6820-6826, 1990.

N. Dyatkina, E. Shirokova, and F. Theil, Modified triphosphates of carbocyclic nucleoside analogues: synthesis, stability towards alkaline phosphatase and substrate properties for some DNA polymerases, Bioorg Med Chem Lett, vol.6, pp.2639-2642, 1996.

A. V. Shipitsin, L. S. Victorova, and E. A. Shirokova, New modified nucleoside 5 '-triphosphates: synthesis, properties towards DNA polymerases, stability in blood serum and antiviral activity, J Chem Soc Perkin Trans, vol.1, pp.1039-1050, 1999.

L. A. Alexandrova, A. Y. Skoblov, and M. V. Jasko, 2 '-Deoxynucleoside 5 '-triphosphates modified at alpha-, beta-and gamma-phosphates as substrates for DNA polymerases, Nucleic Acids Res, vol.26, pp.778-786, 1998.

G. Y. Wang, N. Boyle, and F. Chen, Synthesis of AZT 5 '-triphosphate mimics and their inhibitory effects on HIV-1 reverse transcriptase, J Med Chem, vol.47, pp.6902-6913, 2004.

N. A. Boyle, V. K. Rajwanshi, and M. Prhavc, Synthesis of 2 ',3 '-dideoxynucleoside 5 '-alpha-P-borano-beta, gamma-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase, J Med Chem, vol.48, pp.2695-2700, 2005.

S. Tuske, S. G. Sarafianos, and A. D. Clark, Structures of HIV-1 RT-DNA complexes before and after incorporation of the anti-AIDS drug tenofovir, Nat Struct Mol Biol, vol.11, pp.469-474, 2004.