Diastereoselective synthesis of P-chirogenic phosphoramidate prodrugs of nucleoside analogues (ProTides) via copper catalysed reaction

Article English OPEN
Pertusati, Fabrizio ; McGuigan, Christopher (2015)
  • Publisher: RSC Publishing
  • Related identifiers: doi: 10.1039/C5CC00448A
  • Subject: QD | RM
    mesheuropmc: inorganic chemicals

The first copper-catalysed diastereoselective synthesis of P-chiral phosphoramidate prodrugs (ProTides) is reported. This procedure allows the synthesis of diastereomeric-enriched mixtures of ProTides. Application of this methodology to the asymmetric phosphorylation of purine and pyrimidine nucleoside analogues is presented.
  • References (16)
    16 references, page 1 of 2

    1 L. P. Jordheim, D. Durantel, F. Zoulim and C. Dumontet, Nat. Rev. Drug Discov., 2013, 12, 447-464.

    2 (a) S. J. Hecker and M. D. Erion, J. Med. Chem., 2008, 51, 2328-2345; (b) L. W. Peterson and C. E. McKenna, Expert Opin. Drug Delivery, 2009, 6, 405-420.

    3 (a) C. McGuigan, P. Murziani, M. Slusarczyk, B. Gonczy, J. Vande Voorde, S. Liekens and J. Balzarini, J. Med. Chem., 2011, 54, 7247-7258; (b) M. Slusarczyk, M. H. Lopez, J. Balzarini, M. Mason, G. W. Jiang, S. Blagden, E. Thompson, E. Ghazaly and C. McGuigan, J. Med. Chem., 2014, 57, 1531-1542; (c) K. S. Toti, M. Derudas, F. Pertusati, D. Sinnaeve, F. Van den Broeck, L. Margamuljana, J. C. Martins, P. Herdewijn, J. Balzarini, C. McGuigan and S. Van Calenbergh, J. Org. Chem., 2014, 79, 5097-5112; (d) C. McGuigan, M. Derudas, B. Gonczy, K. Hinsinger, S. Kandil, F. Pertusati, M. Serpi, R. Snoeck, G. Andrei, J. Balzarini, T. D. McHugh, A. Maitra, E. Akorli, D. Evangelopoulos and S. Bhakta, Bioorg. Med. Chem., 2014, 22, 2816-2824; (e) W. Wu and R. F. Borch, Mol. Pharmacol., 2006, 3, 451-456; ( f ) W. Wu, J. Sigmond, G. J. Peters and R. F. Borch, J. Med. Chem., 2007, 50, 3743-3746; (g) F. Pertusati, K. Hinsinger, A´. S. Flynn, N. Powell, A. Tristram, J. Balzarini and C. McGuigan, Eur. J. Med. Chem., 2014, 78, 259-268.

    4 ''Approval of Sovaldi (Sofosbuvir) tablets for the treatment of chronic hepatitis C''. FDA. 7 Dec 2013. Retrieved 9 June 2014.

    5 http://clinicaltrials.gov/ct2/show/NCT01621854?term=nuc1031&rank=3.

    6 http://clinicaltrials.gov/ct2/show/NCT01497899?term=gs7340&rank=3.

    7 D. R. Phillips, M. Uramoto, K. Isono and J. A. McCloskey, J. Org. Chem., 1993, 58, 854-859.

    8 M. E. Tate, P. J. Murphy, W. P. Roberts and A. Kerr, Nature, 1979, 280, 697.

    9 M. Serpi, K. Madela, F. Pertusati and M. Slusarczyk, Synthesis of nucleotide prodrugs using the proTide approach, in Curr. Protoc. Nucleic Acid Chem., John Wiley & Sons, Inc., 2013, vol. 53, pp. 15.5.1-15.5.15.

    10 (a) M. K. H. Chapman, E. Prisbe, J. Rohloff, M. Sparacino, T. Terhorst and R. Yu, Nucleosides, Nucleotides Nucleic Acids, 2001, 20, 621-625; (b) M. J. Sofia, D. Bao, W. Chang, J. Du, D. Nagarathnam, S. Rachakonda, P. G. Reddy, B. S. Ross, P. Wang, H.-R. Zhang, S. Bansal, C. Espiritu, M. Keilman, A. M. Lam, H. M. M. Steuer, C. Niu, M. J. Otto and P. A. Furman, J. Med. Chem., 2010, 53, 7202-7218; (c) A. Cho, L. Zhang, J. Xu, R. Lee, T. Butler, S. Metobo, V. Aktoudianakis, W. Lew, H. Ye, M. Clarke, E. Doerffler, D. Byun, T. Wang, D. Babusis, A. C. Carey, P. German, D. Sauer, W. Zhong, S. Rossi, M. Fenaux, J. G. McHutchison, J. Perry, J. Feng, A. S. Ray and C. U. Kim, J. Med. Chem., 2013, 57, 1812-1825.

  • Similar Research Results (1)
  • Metrics
    views in OpenAIRE
    views in local repository
    downloads in local repository

    The information is available from the following content providers:

    From Number Of Views Number Of Downloads
    Online Research @ Cardiff - IRUS-UK 0 72
Share - Bookmark