Progress in the synthesis of carbocyclic nucleosides

Chinese Journal of Organic Chemistry

Volumn 28, Issue 11, 2008, Pages 1888-1898

  Fan, Xue Sen ^a   Zhang, Xin Ying ^a   Wang, Xia Q U ^a   Qu, Gui Rong ^a  

^a HENAN NORMAL UNIVERSITY   (China)

Author keywords

Antiviral activity; Carbocyclic nucleoside; Synthesis

Indexed keywords

EID: 59749095102     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (79)

1. (a) Chu, C. K. Recent Advances in Nucleosides: Chemistry and Chemotherapy, Elsevier, Amsterdam, 2002.
2. (b) Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties, Gordon and Breach Science Publishers, Amsterdam, 2001.
3. (c) Chu, C. K.; Baker, D. C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents, Plenum Press, New York, 1993.
4. (a) De Clercq, E. Nat. Rev. Drug Discov. 2002, 1, 13.
5. (b) Maury, G. Antiviral Chem. Chemother. 2000, 11, 165.
6. For recent reviews, see:
7. (a) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
8. (b) Wang, J.; Froeyen, M.; Herdewijn, P. In Advances in Antiviral Drug Design, Vol. 4, Ed.: De Clercq, E., Elsevier, Amsterdam, 2004, 119.
9. (c) Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875.
10. (d) Schneller, S. W. Curr. Top. Med. Chem. 2002, 2, 1087.
11. Herdewjin, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550.
12. (a) Marquez, V. E. Adv. Antiviral Drug Des. 1996, 2, 89.
13. (b) Wachtmeister, J.; Classon, B.; Samuelsson, B.; Kvarn-strom, I. Tetrahedron 1995, 51, 2029.
14. (c) Wachtmeister, J.; Classon, B.; Samuelsson, B.; Kvarnstrom, I. Tetrahedron 1997, 53, 1861.
15. (a) Rodriguez, J. B.; Comin, M. J. Mini-Rev. Med. Chem. 2003, 3, 95.
16. (b) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976.
17. (c) Hill, J. M.; Jenkins, G. N.; Rush, C. P.; Turner, N. J.; Willetts, A. J.; Buss, A. D.; Dawson, M. J.; Rudd, B. A. M. J. Am. Chem. Soc. 1995, 117, 5391.
18. (d) Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev. 1995, 169.
19. (e) Yin, X. Q.; Li, W. K.; Schneller, S. W. Tetrahedron Lett. 2006, 47, 9187.
20. (f) Kitade, Y.; Ando, T.; Yamaguchi, T.; Hori, A.; Naka-nishi, M.; Ueno, Y. Bioorg. Med. Chem. 2006, 14, 5578.
21. (g) Yang, M.; Schneller, S. W.; Korba, B. B. J. Med. Chem. 2005, 48, 5043.
22. Arita, M.; Adachi, K.; Ito, Y.; Sawaki, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049.
23. (a) Gallos, J. K.; Stathakis, C. I.; Kotoulas, S. S.; Koumbis, A. E. J. Org. Chem. 2005, 70, 6884.
24. (b) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677.
25. (a) Choi, W. J.; Moon, H. R.; Kim, H. O.; Yoo, B. N.; Lee, J. A.; Shin, D. H.; Jeong, L. S. J. Org. Chem. 2004, 69, 2634.
26. (b) Trost, B. M.; Madsen, R.; Guile, S. D. Tetrahedron Lett. 1997, 38, 1707.
27. Martinez, V. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
28. Moon, H. R.; Choi, W. J.; Kim, H. O.; Jeong, L. S. Chem. Lett. 2004, 33, 506.
29. Michel, B. Y.; Strazewski, P. Tetrahedron 2007, 63, 9836.
30. Glazer, R. I.; Knode, M. C. J. Biol. Chem. 1984, 259, 2964.
31. Shuto, S.; Obara, T.; Yoriya, M.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 324.
32. (a) Shuto, S.; Obara, T.; Saito, Y.; Andrei, G.; Snoeck, R.; De Clercq, E.; Matsuda, A. J. Med. Chem. 1996, 39, 2392.
33. (b) Yang, M.; Schneller, S. W. Bioorg. Med. Chem. Lett. 2005, 15, 149.
34. Rodriguez, S.; Edmont, D.; Mathe, C; Perigaud, C. Tetrahedron 2007, 63, 7165.
35. Zhang, H. W.; Schinazi, R. F.; Chu, C. K. Bioorg. Med. Chem. 2006, 14, 8314.
36. (a) Shealy, Y. F.; O'Dell, C. A.; Shannon, W. M.; Arnett, G. J. Med. Chem. 1984, 27, 1416.
37. (b) Shannon, W. M. In Advances in Chemotherapy of Acquired Immunodeficiency Syndrome, Eds.: Diasio, R. B.; Sommadossi, J. P., Pergammon Press, Inc., New York, 1990, p. 75.
38. (c) Price, P. M.; Banerjee, R.; Acs, G. Proc. Natl. Acad. Sci. U. S.A. 1989, 56, 8541.
39. (d) Boehme, R. E.; Beresford, A.; Hart, G. J.; Angier, S. J.; Thompson, G.; Van Wely, C.; Huang, J. L.; Mack, P.; Soide, K. F. Antiviral Res. 1994, 23, S(l), 97.
40. Lang, H.; Moser, H. E. Helv. Chim. Acta 1994, 77, 1527.
41. Wyatt, P. G.; Anslow, A. S.; Coomber, B. A.; Cousins, R. P. C; Evans, D. N.; Gilber, V. S.; Humber, D. C.; Paternoster, I. L.; Sollis, S. L.; Tapolczay, D. J.; Weingarten, G. G. Nucleosides Nucleotides 1995, 14, 2039.
42. Bray, B. L.; Dolan, S. C; Halter. B.; Lackey, J. W.; Schilling, M. B.; Tapolczay, D. J. Tetrahedron Lett. 1995, 36, 4483.
43. (a) Ludek, O. R.; Meier, C. Synthesis 2003, 2101.
44. (b) Ludek, O. R.; Meier, C. Synlett 2005, 3145.
45. (a) Langley, D. R.; Walsh, A. W.; Baldick, C. J.; Eggers, B. J.; Rose, R. E.; Levine, S. M.; Kapur, A. J.; Colonno, R. J.; Tenney, D. J. J. Virol. 2007, 81, 3992.
46. (b) Rivkin, A. Drugs Today 2007, 43, 201.
47. (c) Wong, D. K.; Yuen, M. F.; Ngai, V. W.; Fung, J.; Lai, C. L. Antiviral Ther. 2006, 11, 909.
48. (d) Yamanaka, G.; Wilson, T.; Innaimo, S.; Bisacchi, G. S.; Egli, P.; Rinehart, J. K.; Zahler, R.; Colonno, R. J. Antim- icrob. Agents Chemother. 1999, 43, 190.
49. Bisacchi, G. G.; Chao, S. T.; Bachard, C; Daris, J. P.; Innaimo, S.; Jacobs, G. A.; Kocy, P. O.; Lapointe P.; Martel, A.; Merchant, Z.; Slusarchyk, W. A.; Sundeen, J. E.; Young, M. G.; Colonno, R.; Zahler, R. Bioorg. Med. Chem. Lett. 1997, 7, 127.
50. Roy, A.; Schneller, S. W.; Keith, K. A.; Hartline, C. B.; Kern, E. R. Bioorg. Med. Chem. 2005, 13, 4443.
51. Roy, A.; Serbessa, T.; Schneller, S. W. Bioorg. Med. Chem. 2006, 14, 4980.
52. Kitade, Y.; Ando, T.; Yamaguchi, T.; Hon, A.; Nakanishi, M.; Ueno, Y. Bioorg. Med. Chem. 2006, 14, 5578.
53. Yang, Y. Y.; Meng, W. D.; Qing, F. L. Org. Lett. 2004, 6, 4257.
54. (a) Huang, W.; Miller, M. J.; De Clercq, E.; Balzarini, J. Org. Biomol. Chem. 2007, 5, 1164.
55. (b) Melroy, J.; Nair, V. Curr. Pharm. Des. 2005, 11, 3847.
56. (c) Vince, R.; Brownell, J. Biochem. Biophys. Res. Commun. 1990, 168, 912.
57. (d) Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
58. (a) Keiser, P.; Nassar, N. Expert Opin. Pharmacother. 2007, 8, 477.
59. (b) Storch, C. H.; Theile, D.; Lindenmaier, H.; Haefeli, W. E.; Weiss, J. Biochem. Pharmacol. 2007, 73, 1573.
60. (c) De Clercq, E. Verh. K. Acad. Geneeskd. Belg. 2007, 69, 81.
61. (d) De Clercq, E. Verh. K. Acad. Geneeskd. Belg. 2007, 69, 65.
62. (e) Kumar, P. N.; Sweet, D. E.; McDowell, J. A.; Symonds, W.; Lou, Y.; Hetherington, S.; Lafon, S. Antimicrob. Agents Chemother. 1999, 43, 603.
63. (f) Hughes, W.; McDowell, J. A.; Shenep, J.; Flynn, P.; Kline, M. W.; Yogey, R.; Symonds, W.; Lou, Y.; Hetherington, S. Antimicrob. Agents Chemother. 1999, 43, 609.
64. Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192.
65. Fang, Z.; Hong, J. H. Org. Lett. 2004, 6, 993.
66. Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719.
67. (a) Oh, C. H.; Hong, J. H. Nucleosides, Nucleotides Nucleic Acids 2007, 26, 403.
68. (b) Kim, A.; Hong, J. H.; Oh, C. H. Nucleosides, Nucleotides Nucleic Acids 2006, 25, 1399.
69. (c) Yan, Z.; Zhou, S.; Kern, E. R.; Zemlicka, J. Tetrahedron 2006, 62, 2608.
70. (d) Marquez, V. E. In Advances in Antiviral Drug Design, Vol. 2, Ed.: De Clercq, E., Elsevier, Amsterdam, 1996, p. 89.
71. Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uchiyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. J. Med. Chem. 1998, 41, 1284.
72. (a) Zhao, Y.; Yang, T. R; Lee, M.; Chun, B. K.; Du, J.; Schinazi, R. F.; Lee, D.; Newton, M. G.; Chu, C. K. Tetrahedron Lett. 1994, 35, 5405.
73. (b) Zhao, Y.; Yang, T. F.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236.
74. (c) Zhao, Y.; Lee, M.; Yang, T. F.; Chun, B. K.; Du, J.; Schinazi, R. F.; Chu, C. K. Nucleosides Nucleotides 1995, 14, 303.
75. (a) De Clercq, E.; Naesens, L.; De Bolle, L.; Schols, D.; Zhang, Y.; Neyts, J. Rev. Med. Virol. 2001, 381.
76. (b) Genovesi, E. V.; Lamb, L.; Medina, I.; Taylor, D.; Seifer, M.; Innaimo, S.; Colonno, R. J.; Clark, J. M. Antiviral Res. 2000, 48, 197.
77. (c) Tenney, D. J.; Yamanaka, G.; Voss, S. M.; Cianci, V.; Tuomari, A. V.; Sheaffer, A. K.; Alam, M.; Colonno, R. J. Antimicrob. Agents Chemother. 1997, 41, 2680.
78. Bisacchi, G. S.; Braitman, A.; Cianci, C. W.; Clark, J. M.; Field, A. K.; Hagen, M. E.; Hockstein, D. R.; Malley, M. F.; Mitt, T.; Slusarchyk, W. A.; Sundeen, J. E.; Terry, B. J.; Tuomari, A. V.; Weaver, E. R.; Young, M. G.; Zahler, R. J. Med. Chem. 1991, 34, 1415.
79. Kaiwar, V.; Reese, C. B.; Gray, E. J.; Neidle, S. J. Chem. Soc, Perkin Trans. 1 1995, 2281.