Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of SATE Prodrug of 6'-Fluoro-6'-methyl-5'-noradenosine Nucleoside Phosphonic Acid as a New Class of Anti-HIV Agent

  • Li, Hua (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Yoo, Jin-Cheol (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Baik, Young-Chan (Hawon Pharmaceuticals Co.) ;
  • Lee, Won-Jae (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK21- Project Team, College of Pharmacy, Chosun University)
  • Received : 2010.06.23
  • Accepted : 2010.07.15
  • Published : 2010.09.20
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Abstract

A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

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References

  1. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. https://doi.org/10.1016/S0040-4020(01)88122-9
  2. Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745. https://doi.org/10.1021/cr00016a004
  3. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. https://doi.org/10.1016/S0040-4020(01)89258-9
  4. Crimmins, M. T. Tetrahedron 1998, 54, 9229. https://doi.org/10.1016/S0040-4020(98)00320-2
  5. Ariona, O.; Gomez, A. M.; Lopez, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919. https://doi.org/10.1021/cr0203701
  6. Zemlicka, J.; Gasser, R.; Freisler, J. V.; Horwitz, J. P. J. Am. Chem. Soc. 1972, 94, 3213. https://doi.org/10.1021/ja00764a053
  7. Mackman, R. L.; Boojamra, C. G.;Prasad, V.; Zhang, L.; Lin, K. Y.; Petrakovsky, O.; Babusis, D.;Chen, J.; Douglas, J.; Grant, D.; Hui, H. C.; Kim, C. U.; Markevitch,D. Y.; Vela, J.; Ray, A.; Cihlar, T. Bioorg. Med. Chem. Lett.2007, 17, 6785. https://doi.org/10.1016/j.bmcl.2007.10.038
  8. Boojamra, C. G.; Mackman, R. L.; Markevitch, D. Y.; Prasad,V.; Ray, A. S.; Douglas, J.; Grant, D.; Kim, C. U.; Cihlar, T. Bioorg. Med. Chem. Lett. 2008, 18, 1120. https://doi.org/10.1016/j.bmcl.2007.11.125
  9. Mackman, R. L.; Lin, K. Y.;Boojamra, C. G.; Hui, H.; Douglas, J.; Grant, D.; Petrakovsky, O.;Prasad, V.; Ray, A. S.; Cihlar, T. Bioorg. Med. Chem. Lett. 2008, 18, 1116. https://doi.org/10.1016/j.bmcl.2007.11.126
  10. Jones, R. J.; Bischofberger, N. Antiviral Res. 1995, 27, 1. https://doi.org/10.1016/0166-3542(95)00011-A
  11. Srinivas, R. V.; Robbins, B. L.; Connelly, M. C.; Gong, Y. F.; Bischofberger,N.; Fridland, A. Antimicrob. Agents Chemother. 1993,37, 2247. https://doi.org/10.1128/AAC.37.10.2247
  12. Perigaud, C.; Aubertin, A. M.; Benzaria, S.; Pelicano, H.; Girardet,J. L.; Maury, G.; Gosselin, G.; Kirn, A.; Imbach, J. L. Biochem. Pharmacol. 1994, 48, 11. https://doi.org/10.1016/0006-2952(94)90217-8
  13. Girardet, J. L.; Perigaud, C.;Aubertin, A. M.; Gosselin, G.; Kirn, A.; Imbach, J. L. Bioorg. Med. Chem. Lett. 1995, 5, 2981. https://doi.org/10.1016/0960-894X(95)00525-7
  14. Palu, G.; Stefanelli, S.; Rassu, M.; Parolin, C.; Balzarini, J.; DeClercq, E. Antiviral Res. 1991, 16, 115. https://doi.org/10.1016/0166-3542(91)90063-W
  15. Naesens, L.; Balzarini, J.; De Clercq, E. Rev. Med. Virol. 1994, 4, 147. https://doi.org/10.1002/rmv.1980040302
  16. Sirbu, D.; Falck-Pedersen, M. L.; Romming, C.; Undheim, K.Tetrahedron 1999, 55, 6703. https://doi.org/10.1016/S0040-4020(99)00316-6
  17. Shimizu, M.; Nakahara, Y. J. Fluorine Chem. 1999, 99, 95. https://doi.org/10.1016/S0022-1139(99)00180-3
  18. Kitade, Y.; Ando, T.; Yamaguchi, T.; Hori, A.; Nakanishi, M.; Ueno, Y. Bioorg. Med. Chem. 2006, 14, 5578. https://doi.org/10.1016/j.bmc.2006.04.023
  19. Michel, B. Y.; Peter, S. Tetrahedron 2007, 63, 9836. https://doi.org/10.1016/j.tet.2007.06.100
  20. Kim, A.; Oh, C. H.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2006, 25, 1399. https://doi.org/10.1080/15257770600918920
  21. Kim, A.; Hong. J. H. Nucleosides Nucleotides Nucleic Acids 2006, 25, 1. https://doi.org/10.1080/15257770500377698
  22. Liu, L. J.; Seo, R. S.; Yoo, S. W.; Choi, J.; Hong, J. H. Bull. Korean Chem. Soc. 2010, 31, 915. https://doi.org/10.5012/bkcs.2010.31.04.915
  23. Lefebvre, I.; Périgaud, C.; Pompon, A.; Aubertin, A. M.; Girardet,J. L.; Kirn, A.; Gosselin, G.; Imbach, J. L. J. Med. Chem. 1995,38, 3941. https://doi.org/10.1021/jm00020a007
  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. Benzaria, S.; Pelicano, H.; Johnson, R.; Maury, G.; Imbach, J. L.; Aubertin, A. M.; Obert, G.; Gosselin, G. J. Med. Chem. 1996, 39, 4958. https://doi.org/10.1021/jm960289o
  26. Pompon, A.; Lefebvre, I.; Imbach, J. L.; Kahn, S.; Farquhar, D. Antiviral Chem. Chemother. 1994, 5, 91.
  27. Lian, L. J.; Yoo, J. C.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2009, 28, 150. https://doi.org/10.1080/15257770902736434

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