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Design, Synthesis and Antiviral Activity of 5-Hydroxymethyl-3-phosphonyl-4,5-dihydrofuran Analogs of Nucleotides

  • Lee, Hee-Yoon (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee, Ki-Ho (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Hah, Jung-Hwan (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Moon, Deuk-Kyu (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee, Chong-Kyo (Korea Research Institute of Chemical Technology)
  • Received : 2010.05.25
  • Accepted : 2010.06.14
  • Published : 2010.08.20

Abstract

Keywords

References

  1. Du, Y.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5701 https://doi.org/10.1021/jo0202233
  2. Hecker, S. J.; Erion, M. D. J. Med. Chem. 2008, 51, 2328. https://doi.org/10.1021/jm701260b
  3. De Clercq, E.; Holy, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. Nature 1986, 323, 464. https://doi.org/10.1038/323464a0
  4. Bronson, J. J.; Ghazzouli, I.; Hitchcock, M. J. M.; Webb, R. R., II.; Martin, J. C. J. Med. Chem. 1989, 32, 1457. https://doi.org/10.1021/jm00127a010
  5. Balzarini, J.; Naesens, L.; Herdewijn, P.; Rosenberg, I.; Holy, A.; Pauwels, R.; Baba, M.; Johns, D. G.; De Clercq, E. Proc. Natl. Acad. Sci. USA 1989, 86, 332. https://doi.org/10.1073/pnas.86.1.332
  6. Adefovir dipivoxil – anti-HIV and anti-HBV. Drugs Future 2000, 25, 844.
  7. Harnden, M. R.; Parkin, A.; Parratt, M. J.; Perkins, R. M. J. Med. Chem. 1993, 36, 1343 https://doi.org/10.1021/jm00062a006
  8. Holy, A.; Votruba, I.; Masojidkova, M.; Andrei, G.; Snoeck, R.; Naesens, L.; De Clerq, E.; Balzarini, J. J. Med. Chem. 2002, 45, 1918. https://doi.org/10.1021/jm011095y
  9. Piperno, A.; Chiacchio, M. A.; Iannazzo, D.; Romeo, R. Curr. Med. Chem. 2006, 13, 3675. https://doi.org/10.2174/092986706779026110
  10. Armstrong, P. D.; Cannon, J. G.; Long, J. P. Nature 1971, 220, 56.
  11. Spande, T. F.; Garaffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475. https://doi.org/10.1021/ja00035a048
  12. McGroddy, K. A.; Carter, A. A; Tubbert, M. M.; Oswald, R. E. Biophys. J. 1993, 64, 325. https://doi.org/10.1016/S0006-3495(93)81373-0
  13. Chen, X.; Wiemer, A. J.; Hohl, R. J.; Wiemer, D. F. J. Org. Chem. 2002, 67, 9331. https://doi.org/10.1021/jo020483k
  14. Bubenick, M.; Rej, R.; Nguyen-Ba, N.; Attardo, G.; Ouellet, F.; Chan, L. Bioorg. Med. Chem. Lett. 2002, 12, 2063.
  15. Gil, J. M.; Hah, J. H.; Oh, D. Y. Tetrahedron Lett. 1998, 39, 3205. https://doi.org/10.1016/S0040-4039(98)00460-2
  16. Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2951.
  17. Hah, J. H.; Gil, J. M.; Oh, D. Y. Tetrahedron Lett. 1999, 40, 8235. https://doi.org/10.1016/S0040-4039(99)01747-5
  18. Jeong, L. S.; Kim, H. O.; Moon, H. R.; Hong, J. H.; Yoo, S. J.; Choi, W. J.; Chun, M. W.; Lee, C.- K. J. Med. Chem. 2001, 44, 806. https://doi.org/10.1021/jm000342f
  19. Zheng, Y.; Nair, V. Tetrahedron 1999, 55, 11803. https://doi.org/10.1016/S0040-4020(99)00681-X
  20. Ma, S.; Gao, W. Synlett 2002, 65.
  21. Ichikawa, J.; Fujiwara, M.; Wada, Y.; Okauchi, T.; Minami, T. J. Chem. Soc. Chem. Commun. 2000, 1887.
  22. Feldman, K. S.; Wrobleski, M. L. J. Org. Chem. 2000, 65, 8659. https://doi.org/10.1021/jo0011080
  23. Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. https://doi.org/10.1016/S0040-4039(97)00315-8
  24. Alonso, I.; Carretero, J. C.; Garrido, J. L.; Magro, V.; Pedregal, C. J. Org. Chem. 1997, 62, 5682. https://doi.org/10.1021/jo970864b
  25. Ruzziconi, R.; Gourves, H. C.; Gourves, J.-P.; Corbel, B. Synlett 2001, 703.
  26. Pevzner, L. M.; Ignat’ev, V. M.; Ionin, B. I. Zh. Obshch. Kim. 1994, 64, 135
  27. Pevzner, L. M.; Ignat’ev, V. M.; Ionin, B. I. Chem. Abstr. 1994, 121, 134268u
  28. Brel, V. K. Synthesis 1999, 463.
  29. Qunter, A. A. Z.; Melman, A.; Srebnik, H. Synlett 2002, 61.
  30. Lee, C.-W.; Oh, D. Y. Heterocycles 1996, 43, 1171. https://doi.org/10.3987/COM-96-7437
  31. Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. J. Chem. Soc. Perkin Trans. 1 1998, 3979.
  32. Yu, K.-L.; Bronson, J. J.; Yang, H.; Patick, A.; Brankovan, V.; Datema, R.; Hithcock, M. J. M.; Martin, J. C. J. Med. Chem. 1993, 36, 2726. https://doi.org/10.1021/jm00071a003
  33. Barchi, J. J., Jr.; Jeong, L. S.; Maqbool, M. A.; Marquez, V. E. J. Biochem. Biophys. Methods 1997, 34, 11. https://doi.org/10.1016/S0165-022X(96)00032-2
  34. Snoeck, R.; Sakuma, T.; De Clerq, E.; Rosenberg, I.; Holy, A. Antimicrob. Agents Chemther. 1988, 32, 1839. https://doi.org/10.1128/AAC.32.12.1839
  35. Lee, Y.-S.; Kim, B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1395. https://doi.org/10.1016/S0960-894X(02)00182-8

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