Hydrolytic reactions of thymidine 5′-O-phenyl-N- alkylphosplioramidates, models of nucleoside 5′-monophosphate prodrugs

Chemistry - A European Journal

Volumn 13, Issue 30, 2007, Pages 8591-8599

  Ora, Mikko ^a   Ojanperä, Jarno ^a   Lönnberg, Harri ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

Hydrolysis; Kinetics; Nucleotides; Phosphoramidates; Prodrugs

Indexed keywords

AMINO ACIDS; CATALYSIS; ESTERS; HYDROLYSIS; NUCLEOPHILES; PHENOLS;

CARBOXYLIC ESTERS; DIASTEREOMERIC; HYDROLYTIC REACTIONS; NUCLEOPHILIC DISPLACEMENT; PHOSPHORAMIDATES; PRODRUGS; THYMIDINE;

NUCLEOTIDES;

NUCLEOSIDE; ORGANOPHOSPHORUS COMPOUND; PRODRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NUCLEOSIDES; ORGANOPHOSPHORUS COMPOUNDS; PRODRUGS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 35349013106     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700623     Document Type: Article

References (55)

1. E. DeClercq, A. Holy, Nat. Rev. Drug Discovery 2005, 4, 928-940.
2. D. Cahard, C. McGuigan. J, Balzarini, Mini-Rev. Med. Chem. 2004, 4, 371-381.
3. P. Poijärvi-Virta. H. Lönnberg. Curr. Med. Chem. 2006, 13, 3441-3465.
4. C. McGuigan, M.-J. Camarasa, H. Egberink, K. Hartman, A. Karlsson, C. F. Perno, J. Balzarini, int. Antiviral News 1997, 5, 19-21.
5. C. McGuigan, D. Cahard, H. M. Sheeka, E. De Clercq, J. Balzarini, J. Med. Chem. 1996, 39, 1748-1753.
6. C. McGuigan, R. N. Pathirana, J. Balzarini, E. De Clercq, J. Med. Chem. 1993, 36, 1048-1052.
7. J. Balzarini, J. Kruining, O. Wedgwood, C. Pannecouque, S. Aquaro, C.-F. Perno, L. Naesens, M. Witvrouw, R. Heijtink, E. De Clercq, C. McGuigan, FEBS Lett. 1997, 410, 324-328.
8. C McGuigan. O. Wedgwood. E. De Clercq, J. Balzarini. Bioorg. Med. Chem. Lett. 1996, 6, 2359-2362.
9. J. Balzarini, H. Egberink, K. Hartmann, A. Karlsson, C.-F. Perno, D. Cahard. L. Naesens, E. Thormar, E. De Clercq, C. McGuigan, Antiviral Res. 1996, 30, A18.
10. C. McGuigan, D. Cahard. A. Salgado, E. DeClercq, J. Balzarini, Antiviral Chem. Chemother. 1996, 7, 31-36.
11. J. Balzarini, A. Karlsson, S. Aquaro. C.-F. Perno, D. Cahard, L. Naesens, E. De Clercq, C. McGuigan, Proc. Natl. Acad. Sci. USA 1996, 93, 7295-7299.
12. J. S. Cooperwood, G. Gumina, F. D. Boudinot, C. K. Chu in Recent Advances in Nucleosides (Ed.: C. K. Chu), Elsevier, Amsterdam, 2002, pp. 91-147.
13. J. Zhu. H. Fu. Y. Jiang, Y Zhao, Synlett 2005, 1927-1929.
14. a) S. M. Gryaznov, N. I. Sokolova, Tetrahedron Lett. 1990, 31, 3205-3208;
15. b) S. M. Gryaznov, J.-K. Chen, J. Am. Chem. Soc. 1994, 116, 3143-3144.
16. A. W. Garrison, C. E. Boozer, J. Am. Chem. Soc 1968, 90, 3486-3494.
17. T. A. Modro, B. P. Rijkmans, J. Org. Chem. 1982, 47, 3208-3211.
18. E. K. Euranto in The Chemistry of Carboxylic Acids and Esters (Ed.: S. Patai), Interscience Publishers, London, 1969, pp. 549-564.
19. M. Ora, M. Oivanen, H. Lönnberg. J. Chem. Soc. Perkin Trans. 2 1996, 771-774.
20. a) R. Lohrmann. L. R. Orgel, J. Mol. Evol. 1976, 7, 253-267;
21. b) A. V. Azhayev, A. A. Krayevsky, X Smrt, Collect. Czech. Chem. Commun. 1979, 44, 792-798;
22. c) W. Bannwart, Helv. Chim. Acta 1988, 71, 1517-1527;
23. d) M. Mag, R. Schmidt, J. W. Engels, Tetrahedron Lett. 1992, 33, 7319-7322;
24. e) M. Mag, J. W. Engels, Tetrahedron 1994, 50, 10225-10234;
25. f) S. M. Gryaznov, H. Winter, Nucleic Acids Res. 1998, 26, 4160-4167;
26. g) M. Ora, K. Mattila, T. Lönnberg, M. Oivanen, H. Lönnberg, J. Am. Chem. Soc. 2002, 124, 14364-14372.
27. E. J. Sampson, J. Fedor, P. A. Benkovic, S. J. Benkovic, J. Org. Chem. 1973, 38, 1301-1306.
28. a) R. F. Hudson, L. Keay, J. Chem. Soc. 1960, 1859-1864;
29. b) P. S. Taylor, F. H. Westheimer, J. Am. Chem. Soc. 1965, 87, 553-559;
30. c) K. E. DeBruin, A. C. Padilla, D. M. Johnson, Tetrahedron Lett. 1971, 12, 4279-4280;
31. d) P. Haake. T. Koizumi. J. Am. Chem. Soc. 1973, 95, 8073-8079.
32. J. D. Chanley, E. Feageson, J. Am. Chem. Soc. 1963, 85, 1181-1190.
33. L. Öney, M. Caplow, J. Am. Chem. Soc. 1967, 89, 6972-6980.
34. S. J. Benkovic, E. J. Sampson, J. Am. Chem. Soc. 1971, 93, 4009-4016.
35. a) P. W. C Barnad, C. A. Bunton, D. R. Llewellyn, C A. Vernon, V. A. Welch, J. Chem. Soc. 1961, 2670-2676;
36. b) J. Engels, Z. Naturforsch. 1977, 32b, 807-809;
37. c) X Engels, Bioorg. Chem. 1979, 8, 9-16;
38. d) J. Varila, T. Hankamäki, M. Oivanen, L. H. Koole, H. Lönnberg, J. Org. Chem. 1997, 62, 893-898.
39. P. Tole, C. Lim, J. Am. Chem. Soc. 1994, 116, 3922-3931.
40. a) F. H. Westheimer, Acc. Chem. Res. 1968, J, 70-78;
41. b) D. A. Usher, D. I. Richardson, Jr., D. G. Oakenfull, J. Am. Chem. Soc. 1970, 92, 4699-4712;
42. c) D. M. Zhou, K. Taira, Chem. Rev. 1998, 98, 991-1026;
43. d) R. Breslow, S.D. Dong, Y. Webb, R. Xu, J. Am. Chem. Soc. 1996, 118, 6588-6600;
44. e) D. M. Perreault, E. V. Anslyn, Angew. Chem. 1997, 109, 470-490;
45. Angew. Chem. Int. Ed. Engl. 1997, 36, 432-450;
46. f) M. Oivanen, S. Kuusela, H. Lönnberg, Chem. Rev. 1998, 98, 961-990;
47. g) H. Lönnberg, R. Strömberg, A. Williams, Org. Biomol. Chem. 2004, 2, 2165-2167;
48. h) T. Lönnberg, H. Lönnberg, Curr. Opin. Chem. Biol. 2005, 9, 665-673.
49. a) N. K. Hamer, R. D. Tack. J. Chem. Soc. Perkin Trans. 2 1974, 1184-1187:
50. b) C. Brown, J. A. Boudreau. B. Hewitson, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1975, 888-895;
51. c) J. Mollin, F. Veverka, F. Kasparek, Collect. Czech. Chem. Commun. 1976, 41, 3245-3255;
52. d) F. Kasparek, J. Mollin, Collect. Czech. Chem. Commun. 1978, 43, 3420-3427;
53. e) F. Kasparek, X Mollin, Collect. Czech. Chem. Commun. 1980, 45, 386-396.
54. a) E. P. Serjeant, B. Dempsey, Ionization Constants of Organic Acids in Aqueous Solution, IUPAC Chemical Data Series No. 23, Pergamon, Oxford, 1979;
55. b) N. E. Good, G. D. Winget, W. Winter, T. N. Connolly. S. Izawa, R. M. M. Singh, Biochemistry 1966, 5, 467-477.