S-Aryltriazole acyclonucleosides: Synthesis and biological evaluation against hepatitis C virus

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 12, 2010, Pages 3610-3613

  Liu, Yang ^a   Xia, Yi ^b   Li, Wei ^a   Cong, Mei ^a   Maggiani, Alain ^b   Leyssen, Pieter ^c   Qu, Fanqi ^a   Neyts, Johan ^c   Peng, Ling ^b  

^a WUHAN UNIVERSITY   (China)

^b AIX MARSEILLE UNIVERSITÉ   (France)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Acyclonucleosides; Hepatitis C virus; S arylated triazole nucleosides; S arylation; Triazole nucleosides

Indexed keywords

ACYCLIC NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; TRIAZOLE;

AMMONOLYSIS; ANTIVIRAL ACTIVITY; ARTICLE; ARYLATION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HEPATITIS C VIRUS; LABORATORY; NONHUMAN; X RAY ANALYSIS;

ANTIVIRAL AGENTS; HEPACIVIRUS; MOLECULAR STRUCTURE; NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR; TRIAZOLES; X-RAY DIFFRACTION;

HEPATITIS C VIRUS;

EID: 77954215196     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.115     Document Type: Article

References (28)

1. S. Claire Nucleoside Mimetics: Their Chemistry and Biological Properties, Advanced Chemistry Texts 2001 Gordon and Beach Science Publishers UK
2. P. Herdewijn, Modified Nucleosides in Biochemistry, Biotechnology and Medicine 2008 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim
3. T. Miyasaka, H. Tanaka, M. Baba, H. Hayakawa, R.T. Walker, J. Balzarini, and E. De Clercq J. Med. Chem. 32 1989 2507
4. H. Tanaka, M. Baba, M. Ubasawa, H. Takashima, K. Sekiya, I. Nitta, S. Shigeta, R.T. Walker, E. De Clercq, and T. Miyasaka J. Med. Chem. 34 1991 1394
5. H. Tanaka, M. Baba, S. Saito, T. Miyasaka, H. Takashima, K. Sekiya, M. Ubasawa, I. Nitta, R.T. Walker, H. Nakashima, and E. De Clercq J. Med. Chem. 34 1991 1508
6. J.S. Ren, R. Esnouf, E. Garman, D. Somers, C. Ross, I. Kirby, J. Keeling, G. Darby, Y. Jones, D. Stuart, and D. Stammers Nat. Struct. Biol. 2 1995 293
7. J.Q. Wan, Y. Xia, Y. Liu, M.H. Wang, P. Rocchi, J.H. Yao, F.Q. Qu, J. Neyts, J.L. Iovanna, and L. Peng J. Med. Chem. 52 2009 1144
8. Y. Xia, Y. Liu, J.Q. Wan, M.H. Wang, P. Rocchi, F.Q. Qu, J. Neyts, J.L. Iovanna, and L. Peng J. Med. Chem. 52 2009 6083
9. R.Z. Zhu, M.H. Wang, Y. Xia, F.Q. Qu, J. Neyts, and L. Peng Bioorg. Med. Chem. Lett. 18 2008 3321
10. Y. Xia, W. Li, F.Q. Qu, Z.J. Fan, X.F. Liu, C. Berro, E. Rauzy, and L. Peng Org. Biomol. Chem. 5 2007 1695
11. Y. Xia, Z.J. Fan, J.H. Yao, Q. Liao, W. Li, F.Q. Qu, and L. Peng Bioorg. Med. Chem. Lett. 16 2006 2693
12. Y. Xia, F.Q. Qu, W. Li, Q.Y. Wu, and L. Peng Heterocycles 65 2005 345
13. W. Li, Y. Xia, Z.J. Fan, F.Q. Qu, Q.Y. Wu, and L. Peng Tetrahedron Lett. 49 2008 2804
14. R.Z. Zhu, F.Q. Qu, G. Quéléver, and L. Peng Tetrahedron Lett. 48 2007 2389
15. J.Q. Wan, R.Z. Zhu, Y. Xia, F.Q. Qu, Q.Y. Wu, G.F. Yang, J. Neyts, and L. Peng Tetrahedron Lett. 47 2006 6727
16. Q.Y. Wu, F.Q. Qu, J.Q. Wan, X. Zhu, Y. Xia, and L. Peng Helv. Chim. Acta 87 2004 811
17. Q.Y. Wu, F.Q. Qu, J.Q. Wan, Y. Xia, and L. Peng Nucleosides Nucleotides Nucleic Acids 2005 999
18. W. Li, Y.T. Fan, Y. Xia, P. Rocchi, R.Z. Zhu, F.Q. Qu, J. Neyts, J.L. Iovanna, and L. Peng Helv. Chim. Acta 92 2009 1503
19. Y. Liu, Y. Xia, Y.T. Fan, A. Maggiani, P. Rocchi, F.Q. Qu, J.L. Iovanna, and L. Peng Bioorg. Med. Chem. Lett. 20 2010 2503
20. D. Loakes Nucleic Acids Res. 29 2001 2437
21. Y. Xia, J.Q. Wan, F.Q. Qu, and L. Peng Synthesis of Nucleoside Analogues with Aromatic Systems Appended on the Triazole Nucleosides M. Hocek, Chemistry of Nucleic Acid Components Collection Symposium Series Vol. 10 2008 Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic Prague 224 228
22. 3CN under argon. The vessel was sealed and the reaction was carried out under microwave irradiation at 100 °C for 30 min, and then cooled to room temperature. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 2:1). The purified material was dried in vacuo to afford the corresponding product 3 as colorless oil.
23. 2. The washed residue was dried in vacuo to afford the corresponding product 4.
24. J.Q. Liu, and M.J. Robins J. Am. Chem. Soc. 129 2007 5962
25. 2 = 0.0712 (I > 2σ(I)), GOF = 1.005. CCDC 762236 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
26. 2), medium was removed and threefold serial dilutions in complete DMEM (without G418) of the test compounds were added in a total volume of 100 μL. After 4 days of incubation at 37 °C, cell culture medium was removed and luciferase activity was determined using the Steady-Glo luciferase assay system (Promega, Leiden, The Netherlands); the luciferase signal was measured using a Luminoskan ascent (Thermo, Vantaa, Finland).
27. J. Paeshuyse, A. Kaul, E. De Clercq, B. Rosenwirth, J.-M. Dumont, P. Scalfaro, R. Bartenschlager, and J. Neyts Hepatology 43 2006 761
28. L. Coelmont, J. Paeshuyse, M.P. Windisch, E. De Clercq, R. Bartenschlager, and J. Neyts Antimicrob. Agents Chemother. 50 2006 3444