Synthesis of novel carbocyclic adenosine analogues as inhibitors of adenosine kinase

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2240-2249

  Cowart, Marion ^a   Bennett, Michael J ^a   Kerwin Jr , James F ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; ADENOSINE KINASE; ARISTEROMYCIN; NUCLEOSIDE ANALOG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033515550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981658m     Document Type: Article

References (72)

1. (a) Guranowski, A.; Montgomery, J. A.; Cantoni, G. L.; Chiang, P. K. Biochemistry 1981, 20, 110.
2. (b) De Clercq, E. Biochem. Pharmacol. 1987, 36, 2567-2575.
3. (a) Yaginuma, S.; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.; Otani, M. J. Antibiot. 1981, 23, 359.
4. (b) Borchardt, R.; Keller, B. T.; Patel-Thrombre, U. J. Biol. Chem. 1984, 259, 5353.
5. (a) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R., Tetrahedron 1994, 50, 10611.
6. (b) Patil, S. D.; Schneller, S. W.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clerq, E. J. Med. Chem. 1992, 35, 3372.
7. (c) Wolfe, M. S.; Lee, Y.; Bartlett, W. J.; Borcherding, D. R.; Borchardt, R. T. J. Med. Chem. 1992, 35, 1782.
8. (a) Borcherding, D. R.; Scholtz, S. A.; Borchardt, R. T. J. Org. Chem. 1987, 52, 5457.
9. (b) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621.
10. (c) Siddiqi, S. M.; Chen, X.; Schneller, S. W. Nucleosides Nucleotides 1993, 12, 267.
11. (d) Siddiqi, S. M.; Chen, X.; Rao, J.; Schneller, S. W. J. Med. Chem. 1995, 38, 1035.
12. (e) Siddiqi, S. M.; Chen, X.; Schneller; S. W.; Ikeda, S.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clerq, E. J. Med. Chem. 1994, 37, 551.
13. (f) Peterson, E. M.; Brownell, J.; Vince, R. J. Med. Chem. 1992, 35, 3991.
14. (g) Trost, B. M.; Madsen, R.; Guile, S. D. Tetrahedron Lett. 1997, 38, 1707.
15. (h) Marquez, V. E.; Lim, B. B.; Driscoll, J. S.; Snoeck, R.; Balzarini, J.; Ikeda, S.; Andrei, G.; De Clercq, E. J. Heterocycl. Chem. 1993, 30, 1393.
16. (i) Madhavan, G. V. B.; Martin, J. C. J. Org. Chem. 1986, 51, 1287.
17. (j) Bhagwat, S. S.; Cowart, M. U.S. Patent 5, 665, 721-A, 1997.
18. (a) Slusarchyk, W. A.; Young, M. G.; Bisacchi, G. S.; Hockstein, D. R.; Zahler, R. Tetrahedron Lett. 1989, 30, 6453-6456.
19. (b) Medich, J.; Kunnen, K. B.; Johnson, C. R. Tetrahedron. Lett. 1987, 28, 4131.
20. (c) Janson, M.; Svansson, L.; Kvarnström, I.; Classon, B.; Samuelsson, B. Nucleosides Nucleotides 1992, 11, 1739.
21. (d) Siddiqi, S. M.; Schneller et al. Nucleosides Nucleotides 1993, 12, 185.
22. (e) Benner, S. Tetrahedron Lett. 1991, 32, 7029.
23. (a) Gundersen, L.-L.; Benneche, T.; Rise, F.; Gogoll, A.; Unheim, K. Acta Chem Scand. 1992, 46, 761-771.
24. (b) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622.
25. (c) Da Silva, A. D.; Coimbra, E. S.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. Tetrahedron Lett. 1993, 34, 6745.
26. (d) Dyatkina, N.; Costisella, B.; Thiel, F.; Janta-Lipinski, M. Tetrahedron Lett. 1994, 35, 1961.
27. (e) Genet, J. P.; Balabane, M.; Backvall, J. E.; Nystrom, J. E. Tetrahedron Lett. 1983, 24, 2745.
28. (a) Patil, S. D.; Schneller, S. W. J. Heterocycl. Chem. 1991, 28, 823.
29. (b) Bergmeier, S. C.; Cobás, A. A.; Rapoport, H. J. Org. Chem. 1993, 58, 2369.
30. (c) Elliott, R. D.; Rener, G. A.; Riordan, J. M.; Secrist, J. A., III; Bennett, L. L. Jr.; Parker, W. B.; Montgomery, J. A. J. Med. Chem. 1994, 37, 739.
31. (d) Jung, M.; Offenbächer, G.; Rétey, J. Helv. Chem. Acta 1985, 66, 1915.
32. (a) Jacobson, K. A.; van Galen, P. J. M.; Williams, M. J. Med. Chem. 1992, 35, 407-422.
33. (b) Williams, M. Nucleosides Nucleotides 1991, 10, 1087-1099.
34. (c) Jacobson, K. A.; Trivedi, B. K.; Churchill, P. C.; Williams, M. Biochem. Pharmacol. 1991, 41, 1399-1410.
35. (d) Newby, A. C. Trends Biochem. Sci. 1984, 9, 42-44.
36. Marangos, P. J. Med. Hypotheses 1990, 32, 45-49.
37. Yamada, Y.; Goto, H.; Ogasawara, N. Biochim. Biophys. Acta 1980, 616, 199-207.
38. (a) Firestein, G.; Boyle, D.; Bullough, D. A.; Gruber, H. E.; Sajjadi, F. G.; Montag, A.; Sambol, B.; Mullane, K. M. J. Immunol. 1994, 152, 5853-5859.
39. (b) Williams, M. Nucleosides Nucleotides 1991, 10, 1087-1099.
40. (c) Cottam, H. B. Drugs Future 1994, 19, 485-491.
41. (d) Keil, G. J., II; DeLander, G. E. Life Sci. 1992, 57, 171-176.
42. (e) Poon, A.; Sawynok, J. Eur. J. Pharmacol. 1995, 286, 177-184.
43. (f) Rosengren, S.; Bong, G. W.; Firestein, G. S. J. Immun. 1995, 154, 5444-5451.
44. (g) Marangos, P. J.; von Lubitz, D.; Daval, J.-L.; Deckert, J. Curr. Future Trends Anticonvulsant, Anxiety, Stroke Ther. 1990, 331-349.
45. (h) Cronstein, B. N.; Naime, D.; Firestein, G. Arth. & Rheum. 1995, 38, 1040-1045.
46. (a) Miller, R. L.; Adamczyk, D. L.; Miller, W. H.; Koszalka, G. W.; Rideout, J. L.; Beacham, L. M., III; Chao, E. Y.; Haggerty, J. J.; Krenitsky, T. A.; Elion, G. B. J. Biol. Chem. 1979, 254, 2346-2352.
47. (b) Henderson, J. F.; Paterson, A. R. P.; Caldwell, I. C.; Paul, B.; Chan, M. C.; Lau, K. F. Cancer Chemother. Rep. 1972, 3, 71-85.
48. (c) Ilitzsch, M. H.; Uber, S. S.; Tankersley, K. O.; el Kouni, M. H. Biochem. Pharmacol. 1995, 49, 1501-1512.
49. (d) Bennett, L. L., Jr.; Hill, D. L. Mol. Pharmacol. 1975, 11, 803-808.
50. (e) Cowart, M.; Bennett, M. J.; Gfesser, G.; Bhagwat, S. S.; Kohlhaas, K. L.; Alexander, K. M.; Zhu, C.; Britton, D.; Lynch, J.; Yu, H.; Gunther, K.; Kerwin, J. F., Jr., Kowaluk, E. A. 213th Meeting of the American Chemical Society, San Francisco, Spring 1997; Paper 173.
51. Kirby, G. W.; McGuigan, H.; MacKinnon, J. W. M.; McLean, D.; Sharma, R. P. J. Chem. Soc., Perkin Trans. 1 1985, 1437-1442.
52. (a) Zhang, D.; Ghosh, A.; Süling, C.; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799.
53. (b) Ghosh, A.; Miller, M. J. Tetrahedron Lett. 1995, 36, 6399.
54. (c) Ghosh, A.; Ritter, A. R.; Miller, M. J. J. Org. Chem. 1995, 60, 5808.
55. (d) Vogt, P. F.; Hansel, J.-G.; Miller, M. J. Tetrahedron Lett. 1997, 38, 2803.
56. (a) Jung, M.; Offenbacher, G.; Retey, J. Helv. Chim. Acta 1983, 66, 1915-1921.
57. (b) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611.
58. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017-3020.
59. Trost, B. M. Acc. Chem. Res. 1980, 13, 385-393.
60. Hupe, D. J.; Wu, D. J. Am. Chem. Soc. 1977, 99, 7653.
61. Holy, A.; Dvorakova, H.; Jindrich, J.; Masojidkova, M.; Budesinsky, M.; Balzarini, J., Andrei, G.; De Clercq, E. J. Med. Chem. 1996, 39, 4073-4088.
62. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
63. Miller, L. J. Am. Chem. Soc. 1979, 101, 4481-4484.
64. Panzica, R. P.; Townsend, L. B. In Nucleic Acid Chemistry vol. 2; Townsend, L. B., Tipson, R. S., Eds.; John Wiley and Sons: New York, 1978; pp 111-116.
65. Trost, B.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-623.
66. Poli, G. Tetrahedron Lett. 1989, 30, 7385-7389.
67. (a) Earl, R. B.; Pugmire, R. J.; Revankar, G. R.; Townsend, L. B. J. Org. Chem. 1974, 40, 1822.
68. (b) Chenon, M.-T.; Pugmire, R. J.; Grant, D. M.; Panzica, R. P.; Townsend, L. B. J. Heterocycl. Chem. 1973, 10, 431.
69. (c) Hecht, S. M.; Werner, D.; Traficante, D. D.; Sundaralingam, M.; Prusiner, P.; Ito, T.; Sakurai, T. J. Org. Chem. 1975, 40, 1815.
70. (d) Oertel, F.; Winter, H.; Kazimierczuk, J. Z.; Vilpo, A.; Richter, P.; Seela, F. Liebigs Ann. Chem. 1992, 1165.
71. Note added in proof: two reports have recently been published of different syntheses of optically active 6 (Hedge, V. R., Seley, K. L., Schneller, S. W. J. Org. Chem. 1998, 63, 7092) and optically acitve 21a (Mulvihill, M. J.; Miller, M. J. Tetrahedron 1998, 54, 6605) by synthetic methods differing from that described here.
72. Note added in proof: two reports have recently been published of different syntheses of optically active 6 (Hedge, V. R., Seley, K. L., Schneller, S. W. J. Org. Chem. 1998, 63, 7092) and optically acitve 21a (Mulvihill, M. J.; Miller, M. J. Tetrahedron 1998, 54, 6605) by synthetic methods differing from that described here.