Synthesis of novel bi-, tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine derived from TSAO-T with nucleophiles

Journal of Organic Chemistry

Volumn 69, Issue 25, 2004, Pages 8758-8766

  Bonache, María Cruz ^a   Chamorro, Cristina ^a,c   Cordeiro, Alessandra ^a   Camarasa, María José ^a   Jimeno, María Luisa ^b   San Félix, Ana ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b CSIC   (Spain)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

NONNUCLEOPHILIC CONDITIONS; POLYCYCLIC NUCLEOSIDES; STEREOSELECTIVITY;

AMINES;

ENAMINE; NUCLEOSIDE;

ANALYTIC METHOD; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; DERIVATIZATION; DNA SEQUENCE; NUCLEOTIDE METABOLISM; POLYMERIZATION; REACTION ANALYSIS; RNA SEQUENCE; SEQUENCE HOMOLOGY; STEREOCHEMISTRY;

AMINES; ANTI-HIV AGENTS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR CONFORMATION; NUCLEOSIDES; SPIRO COMPOUNDS; STEREOISOMERISM; THYMIDINE;

EID: 10044231811     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048706p     Document Type: Article

References (61)

1. Herdewijn, P. Liebigs Ann. 1996, 1337.
2. (a) Kool, E. T. Chem. Rev. 1997, 97, 1473.
3. (b) Herdewijn, P. Biochim. Biophys. Acta 1999, 1489.
4. (c) Meldgaard, M.; Wengel, J. J. Chem. Soc., Perkin Trans, 1 2000, 3539.
5. (a) Tarköy, M.; Bolli, M.; Schweizer, B.; Leumann, C. Helv. Chim. Acta 1993, 76, 481.
6. (b) Tarköy, M.; Leumann, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1432.
7. (c) Egli, M.; Lubini, P.; Bolli, M.; Dobler, M.; Leumann, C. J. Am. Chem. Soc. 1993, 775, 5855.
8. (d) Tarköy, M., Bolli, M.; Leumann, C. Helv. Chim. Acta 1994, 77, 716.
9. (e) Litten, J. C.; Leumann, C. Helv. Chim. Acta 1996, 79, 1129.
10. (f) Bolli, M.; Litten, J. C.; Schütz, R.; Leumann, C. Chem. Biol. 1996, 3, 197.
11. (g) Steffens, R.; Leumann, C. J. Am. Chem. Soc. 1997, 119, 11548.
12. (a) Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331.
13. (b) Altmann, K.-H.; Imwinkelried, R.; Kesselring, R.; Rihs, G. Tetrahedron Lett. 1994, 35, 7625.
14. (c) Wang, G. Tetrahedron Lett. 2000, 41, 7139.
15. (a) Jones, R. J.; Swaminathan, S.; Milligan, J. F.; Wadwani, S.; Froehler, B. C.; Matteucci, M. D. J. Am. Chem. Soc. 1993, 115, 9816.
16. (b) Wang, J.; Matteucci, M. D. Bioorg. Med. Chem. Lett. 1997, 7, 229.
17. (c) Zou, R.; Matteucci, M. D. Tetrahedron Lett. 1996, 37, 941.
18. (d) Van Aerschot, A.; Verheggen, I.; Hendrix, C.; Herdewijn, P. Angew. Chem., Int. Ed, Engl. 1995, 34, 1338.
19. (a) Singh, S. K.; Nielsen, P.; Koshkin, A. A.; Wengel, J. Chem. Commun. 1998, 455.
20. (b) Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
21. (c) Singh, S. K.; Kumar, R.; Wengel, J. J. Org. Chem. 1998, 63, 10035.
22. (a) Ravn, J.; Nielsen, P. J. Chem. Soc., Perkin Trans, 1 2001, 985.
23. (b) Meldgaard, M.; Wengel, J. J. Chem. Soc., Perkin Trans, 1 2000, 3539.
24. (c) Kvaerno, L.; Wightman, R. H.; Wengel, J. J. Org. Chem. 2001, 66, 5106.
25. (d) Sorensen, M. H.; Nielsen, C.; Nielsen, P. J. Org. Chem. 2001, 66, 4878.
26. Marquez, V. E.; Ezzitouni, A.; Russ, P.; Siddiqui, M. A.; Ford, H., Jr.; Feldman, R. J.; Mitsuya, H.; George, C.; Barchi, J. J., Jr. J. Am. Chem. Soc. 1998, 720, 2780.
27. (a) Marquez, V. E.; Russ, P.; Alonso, R.; Siddiqui, M. A.; Hernández, S.; George, C.; Nicklaus, M. C.; Dai, F.; Ford, H., Jr. Helv. Chim. Acta 1999, 82, 2119.
28. (b) Jacobson, K. A.; Ji, X.-d.; Li, A.-H.; Melman, N.; Siddiqui, M. A.; Shin, K.-J.; Marquez, V. E.; Ravi, R. G. J. Med. Chem. 2000, 43, 2196.
29. (c) Comin, M. J.; Rodriguez, J. B.; Russ, P.; Marquez, V. Tetrahedron 2003, 59, 295.
30. (d) Choi, Y.; George, C.; Comin, M. J.; Barchi, J. J., Jr.; Kim, H. S.; Jacobson, K. A.; Baizarini, J.; Mitsuya, H.; Boyer, P. L.; Hughes, S. H.; Marquez, V. E. J. Med. Chem. 2003, 46, 3292.
31. (a) Lescop, C.; Huet, F. Tetrahedron 2000, 56, 2995.
32. (b) Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739.
33. (a) Olsen, A. G.; Rajwanshi, V. K.; Nielsen, C.; Wengel, J. J. Chem. Soc., Perkin Trans. 1 2000, 3610.
34. (b) Kvaerno, L.; Nielsen, C.; Wightman, R. H. Chem. Commun. 2000, 2903.
35. (c) Tronchet, J. M. J.; Brenas, L.; Barbalat-Rey, F.; Zsély, M.; Geoffroy, M. Nucleosides Nucleotides 1998, 17, 1019.
36. (a) Okabe, M.; Sun, R.-C. Tetrahedron Lett. 1989, 30, 2203.
37. (b) Beard, A. R.; Butler, P. I.; Mann, J.; Partlett, N. K. Carbohydr. Res. 1990, 205, 87.
38. Webb, T. R.; Mitsuya, H.; Broder, S. J. Med. Chem. 1988, 31, 1475.
39. Counde, O.-Y.; Kurz, W.; Eugui, E. M.; McRoberts, M. J.; Verheyden, J. P. H.; Kurz, L. J.; Walker, K. A. M. Tetrahedron Lett. 1992, 33, 41.
40. (a) Tronchet, J. M. J.; Zsély, M.; Lassout, O.; Barbalat-Rey, F.; Komaroni, I.; Geoffroy, M. J. Carbohydr. Chem. 1995, 14, 575.
41. (b) Tronchet, J. M. J.; Zsély, M.; Cápek, K.; Komaroni, I.; De Clercq, E.; Balzarini, J. Nucleosides Nucleotides 1994, 13, 1871.
42. (a) Camarasa, M. J.; Díaz-Ortiz, A.; Calvo-Mateo, A.; De las Heras, F. G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1989,32, 1732.
43. (b) Velázquez, S.; Camarasa, M. J. Tetrahedron 1992, 48, 1683.
44. Huss, S.; De las Heras, F. G. Tetrahedron 1991, 1727.
45. Velázquez, S.; Jimeno, M. L.; Huss, S.; Balzarini, J.; Camarasa, M. J. J. Org. Chem. 1994, 59, 7661.
46. (a) Camarasa, M. J.; Pérez-Pérez, M. J.; San-Félix, A.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 2721.
47. (b) Pérez-Pérez, M. J.; San-Félix, A.; Balzarini, J.; De Clercq, E.; Camarasa, M. J. J. Med. Chem. 1992, 35, 2988.
48. (c) Velázquez, S.; San-Félix, A.; Pérez- Pérez, M. J.; Balzarini, J.; De Clercq, E.; Camarasa, M. J. J. Med. Chem. 1993, 36, 3230.
49. (a) Balzarini, J.; Pérez-Pérez, M. J.; San-Félix, A.; Schols, D.; Perno, C. F.; Vandamme, A. M.; Camarasa, M. J.; De Clercq, E. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 4392.
50. (b) Balzarini, J.; Pérez-Pérez, M. J.; San-Félix, A.; Velázquez, S.; Camarasa, M. J.; De Clercq, E. Antimicrob. Agents Chemother. 1992, 36, 1073.
51. (c) Balzarini, J.; Pérez-Pérez, M. J.; San-Félix, A.; Camarasa, M. J.; Bathurst, I. C.; Barr, P. J.; De Clercq, E. J. Biol. Chem. 1992, 267, 11831.
52. (d) Camarasa, M. J.; San-Félix, A.; Pérez-Pérez, M. J.; Velázquez, S.; Alvarez, R.; Chamorro, C.; Jimeno, M. L.; Pérez, C.; Gago, F.; De Clercq, E.; Balzarini, J. J. Carbohydr. Chem. 2000, 19, 451.
53. (e) Camarasa, M. J.; San-Félix, A.; Velázquez, S.; Pérez-Pérez, M. J.; Gago, F.; Balzarini, J. Curr. Top. Med. Chem. 2004, 4, 945.
54. Chamorro, C.; Luengo, S. M.; Bonache, M. C.; Velázquez, S.; Pérez-Pérez, M. J.; Camarasa, M. J.; Gago, F.; Jimeno, M. L.; San-Félix, A. J. Org. Chem. 2003, 68, 6695.
55. Chamorro, C.; Pérez-Pérez, M. J.; Rodriguez-Barrios, F.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Félix, A.; Camarasa, M. J. Antiviral Res. 2001, 50, 207.
56. Ingate, S.; Pérez-Pérez, M. J.; De Clercq, E.; Balzarini, J.; Camarasa, M. J. Antiviral Res. 1995, 27, 281.
57. HyperChem TM. Windows Molecular Modelling System, Release 5.1; HyperCube: Waterloo, Ontario, Canada, 1997.
58. Pérez-Pérez, M. J.; Camarasa, M. J.; Díaz- Ortíz, A.; San-Félix, A.; De las Heras, F. G. Carbohydr. Res. 1991, 276, 399.
59. (a) Nair, V.; Purdy, D. F. Tetrahedron 1991, 47, 365.
60. (b) Cacchi, S.; Misiti, D.; LaTorre, F. Synthesis 1989, 243.
61. Rylander, P. N. Hydrogenation Methods; Academic Press: London, 1985; pp 82-93.