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Synthesis and Anti-HCV Activity of 3',5'-cyclic SATE Phosphonodiester Nucleoside as a Novel Prodrug

  • Liu, Lian Jin (KAST PHARM CO., LTD. #516 Hanyang University) ;
  • Seo, Rac-Seok (KAST PHARM CO., LTD. Hanyang University) ;
  • Yoo, Seung-Won (KAST PHARM CO., LTD. Hanyang University) ;
  • Choi, Jin (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK21- Project Team, College of Pharmacy, Chosun University)
  • Published : 2010.04.20

Abstract

A novel 2',4'-dimethyl carbocyclic adenosine 5'-phosphonic acid analogue (20) was prepared using acyclic stereoselective route from commercially available 4-hydroxybutan-2-one (4). To improve cellular permeability and enhance the anti-HCV activity of this phosphonic acid, a 3',5'-cyclic SATE phosphonodiester nucleoside prodrug (22) was prepared. The synthesized phosphonic nucleoside analogues, (20) and (22), were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line.

Keywords

References

  1. Choo, Q. L.; Kuo, G.; Weiner, A. J.; Overby, L. R.; Bradley, D. W.;Houghton, M. Science 1989, 244, 359. https://doi.org/10.1126/science.2523562
  2. Wu, J. Z.; Yao, N.; Walker, M.; Hong, Z. Mini. Rev. Med. Chem.2005, 5, 1103-1112. https://doi.org/10.2174/138955705774933310
  3. McHutchison, J. G.; Patel, K. Hepatology 2002, 36 suppl 45.
  4. Pawlotsky, J. M. Antiviral Res. 2003, 59, 1. https://doi.org/10.1016/S0166-3542(03)00088-3
  5. Fried, M. W. Hepatology 2002, 36, suppl 237.
  6. Szabo, E.; Lotz, G.; Paska, C.; Kiss, A.; Schaff, Z. Pathol. Oncol. Res. 2003, 9, 215. https://doi.org/10.1007/BF02893380
  7. Bera, S.; Malik, L.; Bhat, B.; Carroll, S. S.; MacCoss, M.; Olsen,D. B.; Tomassini, J. E.; Eldrup, A. B. Bioorg. Med. Chem. Lett.2003, 13, 4455. https://doi.org/10.1016/j.bmcl.2003.09.008
  8. Clark, J. L.; Hollecker, L.; Mason, J. C.; Stuyver,L. J.; Tharnish, P. M.; Lostia, S.; McBrayer, T. R.; Schinazi, R.F.; Watanabe, K. A.; Otto, M. J.; Furman, P. A.; Stec, W. J.; Patterson,S. E.; Pankiewicz, K. W. J. Med. Chem. 2005, 48, 5504. https://doi.org/10.1021/jm0502788
  9. Smith, D. B.; Martin, J. A.; Klumpp, K.; Baker, S. J.; Blomgren, P.A.; Devos, R.; Granycome, C.; Hang, J.; Hobbs, C. J.; Jiang, W. R.;Laxton, C.; Le Pogam, S.; Leveque, V.; Ma, H.; Maile, G.; Merrett,J. H.; Pichota, A.; Sarma, K.; Smith, M.; Swallow, S.; Symons, J.;Vesey, D.; Najera, I.; Cammack, N. Bioorg. Med. Chem. Lett. 2007,17, 2570. https://doi.org/10.1016/j.bmcl.2007.02.004
  10. Li, H.; Baik, Y. C.; Hong, J. H. Bull. Korean Chem. Soc. 2009, 30, 1147. https://doi.org/10.5012/bkcs.2009.30.5.1147
  11. Liu, L. J.; Kim, S. W.; Lee, W.; Hong, J. H. Bull. Korean Chem. Soc. 2009, 30, 2989. https://doi.org/10.5012/bkcs.2009.30.12.2989
  12. Rondla, R.; Coats, S. J.; McBrayer, T. R.; Grier, J.; Johns, M.; Tharnish, P. M.; Whitaker, T.; Zhou, L.; Schinzai, R. F. Antiviral Chem. Chemother. 2009, 20, 99. https://doi.org/10.3851/IMP1400
  13. Li, H.; Yoo, J. C.; Hong, J. H.Nucleosides, Nucleotides & Nucleic Acids 2009, 28, 809. https://doi.org/10.1080/15257770903170294
  14. Ko, O.H.; Hong, J. H. Nucleosides, Nucleotides & Nucleic Acids 2009, 28,761. https://doi.org/10.1080/15257770903155642
  15. Eldrup, A. B.; Allerson, C. R.; Bennett, C. F.; Bera, S.; Bhat, B.; Bhat, N.; Bosserman, M. R.; Brooks, J.; Burlein, C.; Carrol, S. S.; Cook, P. D.; Getty, K. L.; MacCross, M.; McMasters, D. R.; Olsen, D. B.; Prakash, T. P.; Prhavc, M.; Song, Q. L.; Tomassini, J. E.; Xia, J. J. Med. Chem. 2004, 47, 2283. https://doi.org/10.1021/jm030424e
  16. Eldrup, A. B.; Prhavc, M.; Brooks, J.; Bhat, B.; Prakash, T. P.;Song, Q.; Bera, S.; Bhat, N.; Dande, P.; Cook, P. D.; Bennett, C. F.;Carroll, S. S.; Ball, R. G.; Bosserman, M.; Burlein, C.; Colwell, L.F.; Fay, J. F.; Flores, O. A.; Getty, K.; LaFemina, R. L.; Leone, J.;MacCoss, M.; McMasters, D. R.; Tomassini, J. E.; Von Langen,D.; Wolanski, B.; Olsen, D. B. J. Med. Chem. 2004, 47, 5284. https://doi.org/10.1021/jm040068f
  17. Koh, Y. H.; Shim, J. H.; Wu, J. Z.; Zhong, W.; Hong, Z.;Giradet, J.-C. J. Med. Chem. 2005, 48, 2867. https://doi.org/10.1021/jm049029u
  18. Carrol, S. S.;Tomassini, J. E.; Bosserman, M.; Getty, K.; Stahlhut, M. W.; Eldrup,A. B.; Bhat, B.; Hall, D.; Simcoe, A. L.; LaFemina, R.; Rutkowski,C. A.; Wolanski, B.; Yang, Z.; Migliaccio, G.; De Francesco,R.; Kuo, L. C.; MacCross, M.; Olsen, D. B. J. Biol. Chem. 2003,278, 11979. https://doi.org/10.1074/jbc.M210914200
  19. Kim, C. U.; Luh, B. Y.; Martin, J. C. J. Org. Chem. 1991, 56, 2642. https://doi.org/10.1021/jo00008a013
  20. Wu, T.; Froeyen, M.; Kempeneers, V.; Pannecouque, C.; Wang, J.;Busson, R.; De Clwecq, E.; Herdewijn, P. J. Am. Chem. Soc. 2005,127, 5056. https://doi.org/10.1021/ja043045z
  21. Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 25, 235.
  22. Iwasawa, N.; Kato, T.; Narasaka, K. Chem. Lett. 1988, 1721.
  23. Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988,110, 621. https://doi.org/10.1021/ja00210a064
  24. PErigaud, C.; Gosselin, G.; Lefebvre, I.; Girardet, J. L.; Benzaria,S.; Barber, I.; Imbach, J. L. Bioorg. Med. Chem. Lett. 1993, 3, 2521. https://doi.org/10.1016/S0960-894X(01)80709-5
  25. Shim, J.; Larson, G.; Lai, V.; Naim, S.; Wu, J. Z. Antiviral Res.2003, 58, 243. https://doi.org/10.1016/S0166-3542(03)00007-X

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