S-adenosylhomocysteine analogues with the carbon-5′ and sulfur atoms replaced by a vinyl unit

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5093-5096

  Andrei, Daniela ^a   Wnuk, Stanislaw F ^a  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; DRUG DERIVATIVE; S ADENOSYLHOMOCYSTEINE; SULFUR; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ADENOSINE; CATALYSIS; MOLECULAR STRUCTURE; S-ADENOSYLHOMOCYSTEINE; SULFUR; VINYL COMPOUNDS;

EID: 33750897019     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062026m     Document Type: Article

References (52)

1. (a) Yuan, C.-S.; Liu, S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, 1996; Vol. 2, pp 41-88.
2. (b) Turner, M. A.; Yang, X.; Yin, D.; Kuczera, K.; Borchardt, R. T.; Howell, P. L. Cell Biochem. Biophys. 2000, 33, 101-125.
3. (c) Wnuk, S. F. Mini-Rev. Med. Chem. 2001, 1, 307-316.
4. (a) Ueland, P. M. Pharmacol. Rev. 1982, 34, 223-253.
5. (b) Chiang, P. K. Pharmacol. Ther. 1998, 77, 115-134.
6. (a) Nehler, M. R.; Taylor, L. M.; Porter, J. M. Cardiovasc. Surgery 1997, 559-567.
7. (b) Refsum, H.; Ueland, P. M.; Nygard, O.; Vollset, S. E. Annu. Rev. Med. 1998, 49, 31-62.
8. (c) Schynder, G.; Roffi, M.; Pin, R.; Flammer, Y.; Lange, H.; Eberli, F. R.; Meier, B.; Turi, Z. G.; Hess, O. M. N. Engl. J. Med. 2001, 345, 1593-1600.
9. (a) Turner, M. A.; Yuan, C.-S.; Borchardt, R. T.; Hershfield, M. S.; Smith, G. D.; Howell, P. L. Nat. Struct. Biol. 1998, 5, 369-376.
10. (b) Yang, X.; Hu, Y.; Yin, D. H.; Turner, M. A.; Wang, M.; Borchardt, R. T.; Howell, P. L.; Kuczera, K.; Schowen, R. L. Biochemistry 2003, 42, 1900-1909.
11. (c) Hu, Y.; Komoto, J.; Huang, Y.; Gomi, T.; Ogawa, H.; Takata, Y.; Fujioka, M.; Takusagawa, F. Biochemistry 1999, 38, 8323-8333.
12. (a) Wnuk, S. F.; Yuan, C.-S.; Borchardt, R. T.; Baizarini, J.; De Clercq, E.; Robins, M. J. J. Med. Chem. 1994, 37, 3579-3587.
13. (b) Wnuk, S. F.; Mao, Y.; Yuan, C.-S.; Borchardt, R. T.; Andrei, J.; Baizarini, J.; De Clercq, E.; Robins, M. J. J. Med. Chem. 1998, 41, 3078-3083.
14. (c) Yuan, C.-S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. J. Biol. Chem. 1998, 273, 18191-18197.
15. For other examples on the hydrolytic activity of AdoHcy hydrolase, see: (a) Ref 1c.
16. (b) Yang, X.; Yin, D.; Wnuk, S. F.; Robins, M. J.; Borchardt, R.T. Biochemistry 2000, 39, 15234-15241. (4′-Haloacetylene adenosine analogues).
17. (c) Guillerm, G.; Guillerm, D.; Vandenplas-Witkowski, C.; Roginaux, H.; Carte, N.; Leize, E.; Van Dorsselaer, A.; De Clercq, E.; Lambert, C. J. Med. Chem. 2001, 44, 2743-2752. (5′-S-Allenyl-5′-thioadenosine).
18. (d) Jeong, L. S.; Yoo, S. J.; Lee, K. M.; Koo, M. J.; Choi, W. J.; Kim, H. O.; Moon, H. R.; Lee, M. Y.; Park, J. G.; Lee, S. K.; Chun, M. W. J. Med. Chem. 2003, 46, 201-203. (Fluoro-neplanocin A).
19. (e) Wnuk, S. F.; Lewandowska, E.; Sacasa, P. R.; Crain, L. N.; Zhang, J.; Borchardt, R. T.; De Clercq, E. J. Med. Chem. 2004, 47, 5251-5257. (4′-Enyne adenosine analogues).
20. (f) Guillerm, G.; Muzard, M.; Glapski, C. Bioorg. Med. Chem. Lett. 2004, 14, 5799-5802. (Haloethyl esters of homoadenosine-6′-carboxylic acid).
21. (g) Guillerm, G.; Muzard, M.; Glapski, C.; Pilard, S.; De Clercq, E. J. Med. Chem. 2006, 49, 1223-1226. [5′-Deoxy-5′-(cyanomethylene) adenosine].
22. Wnuk, S. F.; Robins, M. J. Can. J. Chem. 1991, 69, 334-338.
23. 5a and suitable alkylzinc bromide produced analogues of type A, see: Wnuk, S. F.; Lalama, J.; Andrei, D.; Garmendia, C.; Robert, J. S-Adenosylhomocysteine and S-ribosylhomocysteine analogues with sulfur atom replaced by the vinyl unit. Abstracts of Papers, Carbohydrate Division, 229th National Meeting of the American Chemical Society, San Diego, CA, March 13-17, 2005; American Chemical Society: Washington, DC, 2005; CARB-035.
24. 9c might give direct access to analogues B.
25. (b) Tan, Z.; Negishi, E.-I. Angew. Chem., Int. Ed. 2006, 45, 762-765.
26. (c) Andrei, D.; Wnuk, S. F. J. Org. Chem. 2006, 71, 405-408.
27. (a) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315.
28. (b) O'Donnell, M. J.; Polt, R. L. J. Org. Chern. 1982, 47, 2663-2666.
29. (a) Grubbs, R. H.; Chang, S.; Tetrahedron 1998, 54, 4413-4450.
30. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
31. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
32. (d) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
33. (e) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
34. Wnuk, S. F.; Robins, M. J. Can. J. Chem. 1993, 71, 192-198.
35. Pablo R. Sacasa, M. Sc. Thesis, Florida International University, 2003.
36. For recent reviews on application of metathesis towards synthesis of nucleoside analogues, see: (a) Agrofoglio, L. A.; Nolan, S. P. Curr. Top. Med. Chem. 2005, 5, 1541-1558.
37. Amblard, F.; Nolan, S. P.; Agrofoglio, L. A. Tetrahedron 2005, 61, 7067-7080.
38. (b) For an example on the self-metathesis reaction of carbohydrate-derived terminal olefins (e.g., 5,6-dideoxy-1,2-O-isopropylidene- α-D-ribo-hex-5-enofuranose), see: Hadwiger, P.; Stütz, A. E. Synlett 1999, 1787-1789.
39. (a) Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107-1108.
40. (b) Biagini, S. C. G.; Gibson, S. E.; Keen, S. P. J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499.
41. (c) Vasbinder, M. M.; Miller, S. J. J. Org. Chem. 2002, 67, 6240-6242.
42. (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
43. (b) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976.
44. 1H NMR analysis of the crude reaction mixtures showed the presence of other isomers in variable quantities of ∼2-8%.
45. (a) Dunn, M. J.; Jackson, R. F. W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
46. (b) Waelchli, R.; Beerli, C.; Meigel, H.; Revesz, L. Bioorg. Med. Chem. Lett. 1997, 7, 2831-2836.
47. (c) Löhr, B.; Orlich, S.; Kunz, H. Synlett 1999, 1139-1141.
48. (d) Bachmann, S.; Knudsen, K. R.; Jorgensen, K. A. Org. Biomol. Chem. 2004, 2, 2044-2049.
49. Schricker, B.; Thirring, K.; Berner, H. Bioorg. Med. Chem. Lett. 1992, 2, 387-390.
50. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
51. (b) Oh, S. S.; Butler, W. M.; Koreeda, M. J. Org. Chem. 1989, 54, 4499-4503.
52. Husstedt, U.; Schäfer, H. J. Tetrahedron Lett. 1981, 623-624.