Solid-Phase Synthesis and Screening of Macrocyclic Nucleotide-Hybrid Compounds Targeted to Hepatitis C NS5B

Chemistry - A European Journal

Volumn 10, Issue 1, 2004, Pages 173-181

  Smietana, Michael ^a   Johnson, Robert B ^b   Wang, Q May ^b   Kool, Eric T ^a  

^a STANFORD UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Antiviral agents; DNA structures; Solid phase synthesis; Structure activity relationships

Indexed keywords

DERIVATIVES; DNA; ENZYMES; GLASS; LEAD COMPOUNDS; SYNTHESIS (CHEMICAL);

STRUCTURAL VARIATIONS;

ORGANIC COMPOUNDS;

CYCLIC NUCLEOTIDE; DNA DIRECTED DNA POLYMERASE ALPHA; HEPATITIS C VIRUS NS5B ENZYME; MACROCYCLIC COMPOUND; PHOSPHORAMIDIC ACID DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE; RIBONUCLEOTIDE; THREONINE; UNCLASSIFIED DRUG; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SCREENING; DRUG SYNTHESIS; DRUG TARGETING; HEPATITIS C; IC 50; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIVIRAL AGENTS; BUTYRIC ACIDS; CYCLIZATION; DNA-DIRECTED DNA POLYMERASE; DRUG EVALUATION, PRECLINICAL; NUCLEOTIDES, CYCLIC; OLIGONUCLEOTIDES; PHASE TRANSITION; RIBONUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL NONSTRUCTURAL PROTEINS;

EID: 0346458586     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305402     Document Type: Article

References (32)

1. a) P. Ross, H. Weinhouse, Y. Aloni, D. Michaeli, P. Weinberg-Ohana, R. Mayer, S. Braun, E. de Vroom, G. A. van der Marel, J. H. van Boom, M. Benziman, Nature 1987, 325, 279-281;
2. b) C.-Y. L. Hsu, D. Dennis, Nucleic Acids Res. 1982, 10, 5637-5647.
3. a) E. T. Kool, Acc. Chem. Res. 1998, 31, 502-510;
4. b) E. T. Kool, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 1-28.
5. a) H. B. Gamper, M. W. Reed, T. Cox, J. S. Virosco, A. D. Adams, Nucleic Acids Res. 1993, 21, 145-150;
6. b) S. Rumney IV, E. T. Kool, Angew. Chem. 1992, 104, 1686-1689; Angew. Chem. Int. Ed. Engl. 1992, 31, 1617-1619.
7. b) S. Rumney IV, E. T. Kool, Angew. Chem. 1992, 104, 1686-1689; Angew. Chem. Int. Ed. Engl. 1992, 31, 1617-1619.
8. a) L. Wang, D. E. Ruffner, Nucleic Acid Res. 1998, 26, 2502-2504;
9. b) S. Wang, E. T. Kool, Nucleic Acid Res. 1994, 22, 2326-2333.
10. a) D. Beaudry, J.-P. Perreaut, Nucleic Acid Res. 1995, 23, 3064-3066;
11. b) G. W. Ashley, D. M. Kushlan, Biochemistry 1991, 30, 2927-2933;
12. c) C. S. Lim, C. A. Hunt, Nucleosides Nucleotides 1997, 16, 41-51.
13. E. Alazzouzi, N. Escaja, A. Grandas, E. Pedroso, Angew. Chem. 1997, 109, 1564-1567; Angew. Chem. Int. Ed. Engl. 1997, 36, 1506-1508.
14. E. Alazzouzi, N. Escaja, A. Grandas, E. Pedroso, Angew. Chem. 1997, 109, 1564-1567; Angew. Chem. Int. Ed. Engl. 1997, 36, 1506-1508.
15. M. Frieden, A. Grandas, E. Pedroso, Chem. Commun. 1999, 1593-1594.
16. R. Micura, Chem. Eur. J. 1999, 5, 2077-2082.
17. M. Smietana, E. T. Kool, Angew. Chem. 2002, 114, 3856-3859; Angew. Chem. Int. Ed. 2002, 41, 3704-3707.
18. M. Smietana, E. T. Kool, Angew. Chem. 2002, 114, 3856-3859; Angew. Chem. Int. Ed. 2002, 41, 3704-3707.
19. G. P. Miller, E. T. Kool, Org. Lett. 2002, 4, 3599-3601.
20. Nucleoside Q is shown in Scheme 3, structure k. For the preparation of nucleoside Q, see: J. C. Morales, E. T. Kool, J. Am. Chem. Soc. 1999, 121, 2323-2324.
21. R. Iyer, W. Egan, J. B. Regan, S. L. Beaucage, J. Am. Chem. Soc. 1990, 112, 1254-1255.
22. C. F. Bleczinski, C. Richert, Org. Lett. 2000, 2, 1697-1700.
23. a) K. Fukui, M. Morimoto, H. Segawa, K. Tanaka, T. Shimidzu, Bioconjugate Chem. 1996, 7, 349-355;
24. b) M. A. Reynolds, T. A. Beck, R. I. Hogrefe, A. McCaffrey, L. J. Arnold, Jr., M. M. Vaguefi, Bioconjugate Chem. 1992, 3, 366-374;
25. c) H. Asanuma, T. Takarada, T. Yoshida, D. Tamaru, X. Liang, M. Komiyama, Angew. Chem. 2001, 113, 2743-2745; Angew. Chem. Int. Ed. 2001, 40, 2671-2673;
26. c) H. Asanuma, T. Takarada, T. Yoshida, D. Tamaru, X. Liang, M. Komiyama, Angew. Chem. 2001, 113, 2743-2745; Angew. Chem. Int. Ed. 2001, 40, 2671-2673;
27. d) H. Asanuma, K. Shirasuka, T. Takarada, H. Kashida, M. Komiyama, J. Am. Chem. Soc. 2003, 125, 2217-2223.
28. a) Molecular Diversity and Combinatorial Chemistry: Libraries and Drug Discovery (Eds.: I. M. Chaiken, K. D. Janda), American Chemical Society, 1996;
29. b) K. J. Lee, A. Angulo, P. Ghazal, K. D. Janda, Org. Lett. 1999, 1, 1859-1862.
30. R. B. Johnson, X.-L. Sun, M. A. Hockman, E. C. Villarreal, M. Wakulchik, Q. M. Wang, Arch. Biochem. Biophys. 2000, 377, 129-134.
31. a) W. Zhang, Z. Luo, C.H.-T. Chen, D. P. Curran, J. Am. Chem. Soc. 2002, 124, 10443-10450;
32. S. M. Sternson, J. B. Louca, J. C. Wong, S. L. Schreiber, J. Am. Chem. Soc. 2001, 123, 1740-1747.