Synthesis of New 3′-, 5-, and N4-Modified 2′-O-Methylcytidine Libraries on Solid Support

Journal of Combinatorial Chemistry

Volumn 5, Issue 6, 2003, Pages 851-859

  Ding, Yili ^a   Habib, Qazi ^a   Shaw, Stephanie Z ^a   Li, David Y ^a   Abt, Jeffrey W ^a   Hong, Zhi ^a   An, Haoyun ^a  

^a Ribapharm Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; BENZENE DERIVATIVE; CYTIDINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; POLYSTYRENE DERIVATIVE; URIDINE DERIVATIVE;

ARTICLE; AUTOMATION; COMBINATORIAL LIBRARY; DERIVATIZATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SOLID STATE;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYTIDINE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; PEPTIDE LIBRARY;

EID: 0345119087     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0300199     Document Type: Article

References (36)

1. (a) Carbon, G. M.; Catapano, C. V.; Fernandes, D. J. Biochem. Pharmacol. 2001, 62, 101-110.
2. (b) Christensen, N. D.; Pickel, M. D.; Budgeon, L. R.; Kreider, J. W. Antiviral Res. 2000, 48, 131-142.
3. (a) De Clercq E.; Descamps, J.; Balzarini, J.; Giziewicz, J.; Barr, P. J.; Robins, M. J. J. Med. Chem. 1983, 26, 661-666.
4. (b) Bobek, M.; Kavai, I.; Sharma, R. A.; Grill, S.; Dutschman, G.; Cheng, Y.-C. J. Med. Chem. 1987, 30, 2154-2157.
5. (c) Shealy, Y. F.; O'Dell, C. A.; Arnett, G.; Shannon, W. M. J. Med. Chem. 1986, 29, 79-84.
6. Boudou-Vivet, V.; Mathe, C.; Gosselin, G. Nucleosides, Nucleotides, Nucleic Acids 2001, 20, 1029-1032.
7. (a) Wang, D.; Ts'o, P. Nucleosides Nucleotides 1996, 15, 387-397.
8. (b) Wang, D.; Meng, B.; Damha, M.; Just, G. Nucleosides Nucleotides 1995, 14, 1961-1984.
9. Sandberg, J.; Bouhana, K.; Gallegos, A.; Agrawal, A.; Grimm, S.; Wincott, F.; Reynolds, M.; Pavco, P.; Parry, T. Antisense Nucleic Acid Drug Dev. 1999, 9, 271-277.
10. (a) See the following special issues. Chem. Rev. 1997, 97 (2), 7. Chem. Rev. 1996, 96 (1). Acc. Chem. Res. 1996, 29 (3), 9.
11. (a) See the following special issues. Chem. Rev. 1997, 97 (2), 7. Chem. Rev. 1996, 96 (1). Acc. Chem. Res. 1996, 29 (3), 9.
12. (a) See the following special issues. Chem. Rev. 1997, 97 (2), 7. Chem. Rev. 1996, 96 (1). Acc. Chem. Res. 1996, 29 (3), 9.
13. (b) Franzen, R. G. J. Comb. Chem. 2000, 2, 195-214.
14. (c) Andres, C. J.; Denhart, D. J.; Deshpande, M. S.; Gillman, K. W. Comb. Chem. High Throughput Screening 1999, 2, 191-210.
15. (d) Kundu, B.; Khare, S. K.; Rastogi, S. K. Prog. Drug Res. 1999, 53, 90-156.
16. (e) Houghten, R. A.; Pinilla, C.; Appel, J. R.; Blondelle, S. E.; Dooley, C. T.; Eichler, J.; Nefzi, A.; Ostresh, J. M. J. Med. Chem. 1999, 42, 3743.
17. (f) Rinnova, M.; Lebl, M. Collect. Czech. Chem. Commun. 1996, 61, 171-231.
18. (a) An, H.; Cook, P. D. Chem. Rev. 2000, 100, 3311-3340.
19. (b) An, H.; Cummins, L. L.; Griffey, R. H.; Bharadwaj, R.; Haly, B. D.; Fraser, A. S.; Wilson-Lingardo, L.; Risen, L. M.; Wyatt, J. R.; Cook, P. D. J. Am. Chem. Soc. 1997, 119, 3696-3708.
20. (c) Barvian, M. R. Chemtracts - Org. Chem. 1998, 11, 639-646.
21. (d) Merritt, A. T. Comb. Chem. High Throughput Screening 1998, 1, 57-72.
22. (a) The Handbook of Nucleoside Synthesis; Vorbruggen, H., Ruh-Pohlenz, C., Eds.; John Wiley & Son: New York, 2001.
23. (b) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988; Vol. 1.
24. (c) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1991; Vol. 2.
25. (d) Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3.
26. Varaprasad, C. V.; Habib, Q.; Li, D. Y.; Huang, J.; Abt, J. W.; Rong, F. ; Hong, Z.; An, H. Tetrahedron 2003, 59, 2297-2307.
27. "Successful rate" for a plate of 96 compounds was defined as the percentage of the library members with more than 60% LC-MS purity as compared to all 96 compounds in the plate. Therefore, it represents the quality of a plate synthesized. Library members with more than 60% LC-MS purity were registered to the database for the biological screening to reduce false-positive and false-negative results. The higher the successful rate is, the higher quality the library has.
28. (a) Nyilas, A.; Chattopadhyaya, J. Acta Chem. Scand. 1986, B40, 826-830.
29. (b) Giziewicz, J.; Shugar, D. Acta Biochim. Pol. 1973, 20, 73-81.
30. (c) Yamauchi, K.; Nakagima, T.; Kinoshita, N. J. Chem. Soc., Perkin Trans. 1 1980, 2787-2792.
31. Edmonds, C. G.; Crain, P. F.; Hashizume, T.; Gupta, R.; Stetter, K. O.; McCloskey, J. A. J. Chem. Soc., Chem. Commun. 1987, 909-910.
32. Vagner, R. W.; Matteucci, M. D.; Grant, D.; Huang, T.; Froehler, B. C. Nature Biotechnol. 1996, 14, 840-844.
33. An, H.; Wang, T.; Cook, P. D. Tetrahedron Lett. 2000, 41, 7813-7816.
34. An, H.; Wang, T.; Maier, M. A.; Manoharan, M.; Ross, B. S.; Cook, P. D. J. Org. Chem. 2001, 66, 2789-2801.
35. (a) Asakura, J.-I.; Robins, M. J. J. Org. Chem. 1990, 55, 4928-4933.
36. (b) Matulic-Adamic, J.; Daniher, A. T.; Karpeisky, A.; Haeberli, P.; Sweedler, D.; Beigelman, L. Bioorg. Med. Chem. Lett. 2000, 10, 1299-1302.