Synthesis and anti-HCV activity of a new 2′-deoxy-2′-fluoro- 2′-C-methyl nucleoside analogue

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 24, 2010, Pages 7297-7298

  Hu, Weidong ^a   Wang, Ping'An ^b   Song, Chuanjun ^a   Pan, Zhenliang ^a   Wang, Qiang ^a   Guo, Xiaohe ^c   Yu, Xuejun ^c   Shen, Zhenhua ^a   Wang, Shuyang ^a   Chang, Junbiao ^a  

^a ZHENGZHOU UNIVERSITY   (China)

^b HENAN UNIVERSITY   (China)

^c Henan Academy of Science   (China)

Author keywords

2 Deoxy 2 fluoro 2 C methyl nucleoside; Anti HCV activity

Indexed keywords

2' DEOXY 2' FLUORO 2' C METHYL NUCLEOSIDE ANALOG; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS C VIRUS; HUMAN; HUMAN CELL; VIRUS REPLICATION;

ANTIVIRAL AGENTS; CELL LINE; HEPACIVIRUS; HUMANS; NUCLEOSIDES; RNA, VIRAL; VIRAL NONSTRUCTURAL PROTEINS; VIRUS REPLICATION;

HEPATITIS C VIRUS;

EID: 78449278115     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.076     Document Type: Article

References (22)

1. M.J. Later World J. Gastroenterol. 13 2007 2436
2. J.A. Cuthbert Clin. Microbiol. Rev. 7 1994 505
3. A.M. Di Bisceglie Hepatology 31 2000 1014
4. T. Poynard, M.-F. Yuen, V. Ratziu, and C.L. Lai Lancet 362 2003 2095
5. For a review of anti-HIV and anti-HCV drugs, see: E. De Clercq Nat. Rev. Drug Disc. 6 2007 1001
6. S.S. Carroll, J.E. Tomassini, M. Bosserman, K. Getty, M.W. Stahlhut, A.B. Eldrup, B. Bhat, D. Hall, A.L. Simcoe, R. LaFemina, C.A. Rutkowski, B. Wolanski, Z. Yang, G. Migliaccio, R.D. Francesco, L.C. Kuo, M. MacCoss, and D.B. Olsen J. Biol. Chem. 278 2003 11979
7. A.B. Eldrup, M. Prhavc, J. Brooks, B. Bhat, T.P. Prakash, Q. Song, S. Bera, N. Bhat, P. Dande, P.D. Cook, C.F. Bennett, S.S. Carroll, R.G. Ball, M. Bosserman, C. Burlein, L.F. Colwell, J.F. Fay, O.A. Flores, K. Getty, R.L. LaFemina, J. Leone, M. MacCoss, D.R. McMasters, J.E. Tomassini, D.V. Langen, B. Wolanski, and D.B. Olsen J. Med. Chem. 47 2004 5284
8. J.L. Clark, L. Hollecker, J.C. Mason, L.J. Stuyver, P.M. Tharnish, S. Lostia, T.R. McBrayer, R.F. Schinazi, K.A. Watanabe, M.J. Otto, P.A. Furman, W.J. Stec, S.E. Patterson, and K.W. Pankiewicz J. Med. Chem. 48 2005 5504
9. P. Wang, B.-K. Chun, S. Rachakonda, J. Du, N. Khan, J. Shi, W. Stec, D. Cleary, B.S. Ross, and M.J. Sofia J. Org. Chem. 74 2009 6819
10. S. Wang, J. Chang, S. Pan, and K. Zhao Helv. Chim. Acta 87 2004 327
11. B. Zhao, J. Chang, Q. Wang, Y. Du, and K. Zhao Synlett 2008 2993
12. Chang, J.; Yu, X.; Wang, L.; Wang, Q.; Qi, X.; Dong, C. Faming Zhuanli Shengqing Gongkai Shuomingshu, CN 1626543, 2005; Chem. Abstr. 2005, 144, 150595.
13. Chang, J.; Yu, X.; Bao, X.; Ye, Z. Faming Zhuanli Shengqing Gongkai Shuomingshu, CN 1712409, 2005; Chem. Abstr. 2005, 145, 489507.
14. Chang, J.; Bao, X.; Wang, Q.; Guo, X.; Wang, W.; Qi, X. Faming Zhuanli Shengqing Gongkai Shuomingshu, CN 101177442, 2008; Chem. Abstr. 2008, 149, 32518.
15. Q. Wang, Y. Li, C. Song, K. Qian, C.-H. Chen, K.-H. Lee, and J. Chang Bioorg. Med. Chem. Lett. 20 2010 4053
16. J.L. Clark, J.C. Mason, A.J. Hobbs, L. Hollecker, and R.F. Schinazi J. Carbohydr. Chem. 25 2006 461
17. 3) for the α-anomer (more polar spot on TLC): 8.62 (1H, s), 8.11-7.36 (11H, m), 6.86 (1H, d, J = 18.2 Hz), 5.81 (1H, dd, J = 21.6, 8.7 Hz), 4.91 (1H, m), 4.72 (1H, dd, J = 12.2, 3.7 Hz), 4.61 (1H, dd, J = 12.2, 4.6 Hz) and 1.54 (3H, d, J = 22.0 Hz). Determination of the stereochemistry was based on a NOE correlation of ribofuranose H-1′ with H-3′ in the α anomer.
18. 3 requires 301.1112.
19. D.-R. Hwang, H.-Y. Lai, M.-L. Chang, J.T. Hsu, and C.-T. Yeh J. Virol. Methods 129 2005 170
20. D.-R. Hwang, Y.-C. Tsai, J.-C. Lee, K.-K. Huang, R.-K. Lin, C.-H. Ho, J.-M. Chiou, Y.-T. Lin, J.T. Hus, and C.-T. Yeh Antimicrob. Agents Chemother. 48 2004 2876
21. C.-T. Yeh, D.-R. Hwang, H.-Y. Lai, and J.T. Hsu Biochem. Biophys. Res. Commun. 310 2003 537
22. C.-T. Yeh, H.-Y. Lai, T.-C. Chen, C.-M. Chu, and Y.-F. Liaw J. Virol. 75 2001 11017