Design and synthesis of new C-nucleosides as potential adenosine deaminase inhibitors

Tetrahedron

Volumn 66, Issue 50, 2010, Pages 9620-9628

  Tite, Tony ^a   Lougiakis, Nikolaos ^a   Myrianthopoulos, Vassilios ^a   Marakos, Panagiotis ^a   Mikros, Emmanuel ^a   Pouli, Nicole ^a   Tenta, Roxane ^b   Fragopoulou, Elisabeth ^b   Nomikos, Tzortzis ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b HAROKOPIO UNIVERSITY   (Greece)

Author keywords

Enthalpy of hydration; Mitsunobu; Nucleosides; Pyrazolopyridine

Indexed keywords

3 (BETA RIBOFURANOSYL)PYRAZOLO[3,4 C]PYRIDINE; 3 (BETA RIBOFURANOSYL)PYRAZOLO[4,3 B]PYRIDINE; 5 AMINO 3 (BETA RIBOFURANOSYL)PYRAZOLO[3,4 C]PYRIDINE; 5 AMINO 3 (BETA RIBOFURANOSYL)PYRAZOLO[4,3 B]PYRIDINE; ADENOSINE DEAMINASE INHIBITOR; C NUCLEOSIDE; PICOLINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; MITSUNOBU REACTION; MOLECULAR MODEL; PRIORITY JOURNAL; REDUCTION;

EID: 78449252739     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.005     Document Type: Article

References (38)

1. L.C. Kurz, and C. Frieden Biochemistry 26 1987 8450 8457
2. L. Frick, J.P. Neela, and R. Wolfenden Bioorg. Chem. 15 1987 100 108
3. G.K. Schroeder, and R. Wolfenden Biochemistry 46 2007 13638 13647
4. A. Aiuti Curr. Opin. Mol. Ther. 4 2002 515 522
5. R. Resta, and L.F. Thompson Immunol. Today 18 1997 371 374
6. G.G. Yegutkin Biochim. Biophys. Acta, Mol. Cell Res. 1783 2008 673 694
7. A. Ohta, and M. Sitkovsky Nature 414 2001 916 920
8. K.J. Broadley Expert Opin. Ther. Pat. 10 2000 1669 1692
9. M. Mandapathil, B. Hilldorfer, M.J. Szczepanski, M. Czystowska, M. Szajnik, J. Ren, S. Lang, E.K. Jackson, E. Gorelik, and T.L. Whiteside J. Biol. Chem. 285 2010 7176 7186
10. R.S. Hosmane Curr. Top. Med. Chem. 2 2002 1093 1109
11. G. Cristalli, S. Costanzi, C. Lambertucci, G. Lupidi, S. Vittori, R. Volpini, and E. Camaioni Med. Res. Rev. 21 2001 105 128
12. T. Terasaka, K. Tsuji, T. Kato, I. Nakanishi, T. Kinoshita, Y. Kato, M. Kuno, T. Inoue, K. Tanaka, and K. Nakamura J. Med. Chem. 48 2005 4750 4753
13. V.E. Marquez, G.K. Schroeder, O.R. Ludek, M.A. Siddiqui, A. Ezzitouni, and R. Wolfenden Nucleosides Nucleotides 28 2009 614 632
14. C. Lathia, G.F. Fleming, M. Meyer, M.J. Ratain, and L. Whitfield Cancer Chemother. Pharmacol. 50 2002 121 126
15. R.P. Agerwal, T. Spector, and R.E. Parks Biochem. Pharmacol. 26 1977 359 367
16. M. Rafel, F. Cervantes, J.M. Beltran, J. Zuazu, L.H. Nieto, C. Rayon, J.G. Talavera, and E. Montserrat Cancer 88 2000 352 357
17. C. La Motta, S. Sartini, L. Mugnaini, S. Salerno, F. Simorini, S. Taliani, A.-M. Marini, F. Da Settimo, A. Lavecchia, E. Novellino, L. Antonioli, M. Fornai, C. Blandizzi, and M. Del Tacca J. Med. Chem. 52 2009 1681 1692
18. T. Kinoshita, I. Nakanishi, T. Terasaka, M. Kuno, N. Seki, M. Warizaya, H. Matsumura, T. Inoue, K. Takano, H. Adachi, Y. Mori, and T. Fujii Biochemistry 44 2005 10562 10569
19. T. Kinoshita, T. Tada, and I. Nakanishi Biochem. Biophys. Res. Commun. 373 2008 53 57
20. V.N. Kourafalos, P. Marakos, N. Pouli, and L.B. Townsend Synlett 2002 1479 1482
21. V.N. Kourafalos, P. Marakos, N. Pouli, and L.B. Townsend J. Org Chem. 68 2003 6466 6469
22. S. Korouli, N. Lougiakis, P. Marakos, and N. Pouli Synlett 2008 181 184
23. V.N. Kourafalos, T. Tite, E. Mikros, P. Marakos, N. Pouli, and J. Balzarini Synlett 2008 3129 3132
24. S.D. Lindell, B.A. Moloney, B.D. Hewitt, C.G. Earnshaw, P.J. Dudfield, and J.E. Dancer Bioorg. Med. Chem. Lett. 9 1999 1985 1990
25. G. Bojack, C.G. Earnshaw, R. Klein, S.D. Lindell, C. Lowinski, and R. Preuss Org. Lett. 3 2001 839 842
26. D.K. Wilson, F.B. Rudolph, and F.A. Quiocho Science 252 1991 1278 1284
27. D. Chapman, and J. Hurst J. Chem. Soc., Perkin Trans. 1 1980 2398 2404
28. N. Lougiakis, P. Marakos, N. Pouli, and J. Balzarini Chem. Pharm. Bull. 56 2008 775 780
29. T.J. Cousineau, and J.A. Secrist III J. Org. Chem. 44 1979 4351 4358
30. W. Timpe, K. Dax, N. Wolf, and H. Weidmann Carbohydr. Res. 69 1975 51 60
31. P. Marakos, N. Pouli, D. Wise, and L.B. Townsend Synlett 1997 561 562
32. S.S. Kulkarni, and A.H. Newman Bioorg. Med. Chem. Lett. 17 2007 2987 2991
33. K.R. Romines, G.A. Freeman, L.T. Schaller, J.R. Cowan, S.S. Gonzales, J.H. Tidwell, C.W. Andrews, D.K. Stammers, R.J. Hazen, R.G. Ferris, S.A. Short, J.H. Chan, and L.R. Boone J. Med. Chem. 49 2006 727 739
34. 3).
35. 3).
36. T. Tite, N. Lougiakis, P. Marakos, and N. Pouli Synlett 2009 1741 1744
37. Jaguar 2002 Schrödinger, LLC New York, NY
38. F. Mohamadi, N.G.J. Richard, W.C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still J. Comput. Chem. 11 1990 440 467