Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 4, 2005, Pages 1239-1248

  Amblard, Franck ^a   Aucagne, Vincent ^a   Guenot, Pierre ^b   Schinazi, Raymond F ^c   Agrofoglio, Luigi A ^a  

^a Université d'Orléans   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antiviral activity; Furopyrimidine; Nucleosides

Indexed keywords

1 (4,5 DIHYDROXY 2 PENTENYL) 5 [2 (4 PENTYLPHENYL)ETHYNYL] 2,4(1H,3H) PYRIMIDINEDIONE; 1 [4 HYDROXY 3 (HYDROXYMETHYL) 2 BUTENYL] 5 [2 (4 PENTYLPHENYL)ETHYNYL] 2,4(1H,3H) PYRIMIDINEDIONE 3 (HYDROXYMETHYL) 2 BUTENYL 2,4(1H,3H) PYRIMIDINEDIONE; 1 N (2 HYDROXYETHOXYMETHYL) 5 (4 PENTYLPHENYLETHYNYL)URACIL; 1 N (2 HYDROXYETHOXYMETHYL) 5 (DEC 1 YNYL)URACIL; 1 N (2 HYDROXYETHOXYMETHYL) 5 (HEPT 1 YNYL)URACIL; 1 N (2 HYDROXYETHOXYMETHYL) 5 (PHENYLETHYNYL)URACIL; 3 (4,5 DIHYDROXY 2 PENTENYL) 6 (4 PENTYLPHENYL)FURO[2,3 D]PYRIMIDIN 2(3H) ONE; 3 (4,5 DIHYDROXY 2 PENTENYL) 6 OCTYLFURO[2,3 D]PYRIMIDIN 2(3H) ONE; 3 [4 HYDROXY 3 (HYDROXYMETHYL) 2 BUTENYL] 6 (4 PENTYLPHENYL)FURO[2,3 D]PYRIMIDIN 2(3H) ONE; 3 [4 HYDROXY 3 (HYDROXYMETHYL) 2 BUTENYL] 6 OCTYLFURO[2,3 D]PYRIMIDIN 2(3H) ONE; 3 N (2 HYDROXYETHOXYMETHYL) 6 (4 PENTYLPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 N (2 HYDROXYETHOXYMETHYL) 6 OCTYL 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 N (2 HYDROXYETHOXYMETHYL) 6 PENTYL 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 N (2 HYDROXYETHOXYMETHYL) 6 PHENYL 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 5 (1 DECYNYL) 1 (4,5 DIHYDROXY 2 PENTENYL) 2,4(1H,3H) PYRIMIDINEDIONE; 5 (1 DECYNYL) 1 [4 HYDROXY 3 (HYDROXYMETHYL) 2 BUTENYL] 2,4(1H,3H) PYRIMIDINEDIONE; 5 ACETYL 1 (4,5 DIHYDROXY 2 PENTENYL) 2,4(1H,3H) PYRIMIDINEDIONE; 5 ACETYL 1 [4 HYDROXY 3 (HYDROXYMETHYL) 2 BUTENYL] 2,4(1H,3H) PYRIMIDINEDIONE; ACICLOVIR; ANTIVIRUS AGENT; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFECT; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; VERO CELL;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; HIV; HUMANS; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; PYRIMIDINES; SIMPLEXVIRUS;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 12844249473     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.11.057     Document Type: Article

References (48)

1. L.A. Agrofoglio, and S.R. Challand Acyclic, Carbocyclic and l-Nucleosides 1998 Kluwer Academic Dordrecht
2. C.K. Chu, and S.J. Cutler J. Heterocycl. Chem. 23 1986 289
3. E. De Clerq, A. Holy, I. Rosenberg, T. Sakuma, J. Balzarini, and P.C. Maudgal Nature 323 1986 464
4. L. Naesens, R. Snoeck, G. Andrei, J. Balzarini, J. Neyts, and E. De Clercq Antiviral Chem. Chemother. 8 1997 1
5. H.S. Kim, D. Barak, K.T. Harden, J.L. Boyer, and K.A. Jacobson J. Med. Chem. 44 2001 3092
6. D.R. Borcherding, S. Narayanan, M. Hasobe, J.G. McKee, B.T. Keller, and R.T. Borchardt J. Med. Chem. 31 1988 1729
7. D.R. Haines, C.K. Tseng, and V.E. Marquez J. Med. Chem. 30 1987 943
8. G.B. Elion, P.A. Furman, J.A. Fyfe, P. De Miranda, L. Beauchamp, and H. Schaeffer J. Proc. Natl. Acad. Sci. U.S.A. 74 1977 5716
9. H.J. Schaeffer, L. Beauchamp, P. De Miranda, G.B. Elion, D.J. Buaer, and P. Collins Nature 272 1978 583
10. P.A. Furman, P. Miranda, M.H.S. De Clair, and G.B. Elion Antimicrob. Agents Chemother. 20 1981 518
11. E. De Clercq B. Testa Adv. Drug Res. 1988 Academic London pp 1
12. A.K. Field, M.E. Davies, C. DeWitt, H.C. Perry, R. Liou, J. Gemershausen, J.D. Karkas, W.T. Ashton, D.B.R. Johnston, and R.L. Tolman Proc. Nat. Acad. Sci. U.S.A. 80 1983 4139
13. D.F. Smee, J.C. Martin, J.P.H. Verheyden, and T.R. Matthews Antimicrob. Agents Chemother. 23 1983 676
14. J.C. Martin, C.A. Dvorak, D.F. Smee, T.R. Matthews, and J.P.H. Verheyden J. Med. Chem. 26 1983 759
15. K.K. Ogilvie, U.O. Cheriyan, B.K. Radatus, K.O. Smith, K.S. Galloway, and W.L. Kennel Can. J. Chem. 60 1982 3005
16. L.A. Agrofoglio, I. Gillaizeau, and Y. Saito Chem. Rev. 103 2003 1875
17. N.G. Kundu, B. Das, C.P. Spears, A. Majumdar, and S.-I. Kang J. Med. Chem. 33 1990 1975
18. N.G. Kundu, S.K. Dasgupta, L.N. Chaudhuri, J.S. Mahanty, C.P. Spears, and A.H. Shahinian Eur. J. Med. Chem. 28 1993 473
19. N.G. Kundu, J.S. Mahanty, and C.P. Spears Bioorg. Med. Chem. Lett. 6 1996 1497
20. R. Kumar, M. Nath, and J. Tyrrell J. Med. Chem. 45 2002 2032
21. E. De Clercq, J. Descamps, P. De Somer, P.J. Barr, A.S. Jones, and R.T. Walker Proc. Natl. Acad. Sci. U.S.A. 76 1979 2947
22. C. McGuigan, C.J. Yarnold, G. Jones, S. Velasquez, H. Barucki, A. Brancale, G. Andrei, R. Snoeck, E. De Clercq, and J. Balzarini J. Med. Chem. 42 1999 4479
23. C. McGuigan, H. Barucki, S. Blewett, A. Carangio, J.T. Erischen, G. Andrei, R. Snoeck, E. De Clercq, and J. Balzarini J. Med. Chem. 43 2000 4993
24. S. Srinivasan, C. McGuigan, G. Andrei, R. Snoeck, E. De Clercq, and J. Balzarini Bioorg. Med. Chem. Lett. 11 2001 391
25. C. McGuigan, A. Brancale, H. Barucki, S. Srinivasan, G. Jones, R. Pathirana, S. Blewett, R. Alvarez, C.J. Yarnold, A. Carangio, S. Velazquez, G. Andrei, R. Snoeck, and E. De Clercq Drugs Future 25 2000 1151
26. V.D. Patil, D.S. Wise, L.B. Towsend, and A. Bloch J. Med. Chem. 17 1974 1282
27. V.D. Patil, D.S. Wise, L.L. Wotring, L.C. Bloomer, and L.B. Towsend J. Med. Chem. 28 1985 423
28. N. Kifli, E. De Clercq, J. Balzarini, and C. Simons Bioorg. Med. Chem. 12 2004 4245
29. T. Mansour, C.A. Evans, M. Charron, and B.E. Korba Bioorg. Med. Chem. Lett. 7 1997 303
30. T. Mansour, C.A. Evans, M.A. Siddiqui, M. Charron, B. Zacharie, N. Nguyen-Ba, N. Lee, and B.E. Korba Nucleosides Nucleotides 16 1997 993
31. J.L. Kelley, J.E. Kelsey, W.R. Hall, M.P. Krochmal, and H.J. Schaeffer J. Med. Chem. 24 1981 753
32. M.J. Robins, and P.H. Hatfield Can. J. Chem. 60 1982 547
33. J.I. Asakura, and M.J. Robins J. Org. Chem. 55 1990 4928
34. K. Sonogashira Trost Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 521
35. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467
36. S. Takahashi, Y. Kuroyama, K. Sonogashira, and N. Hagihara Synthesis 1980 627
37. M.J. Robins, R.V. Vinayak, and S.G. Wood Tetrahedron Lett. 26 1990 3731
38. F. Amblard, S. Nolan, R.F. Schinazi, and L.A. Agrofoglio Tetrahedron Lett. 44 2004 9177
39. F. Amblard, S.P. Nolan, R.F. Schinazi, and L.A. Agrofoglio Tetrahedron 61 2005 537 544
40. M.J. Robins, and P.J. Barr J. Org. Chem. 48 1983 1854
41. M.J. Robins, and P.J. Barr Tetrahedron Lett. 22 1981 421
42. C.E. Castro, E.J. Gaughan, and D.C. Owsley J. Org. Chem. 31 1966 4071
43. R.C. Bleackey, A.S. Jones, and R.T. Walker Tetrahedron 32 1976 2795
44. V. Aucagne, F. Amblard, and L.A. Agrofoglio Synlett 13 2004 2406
45. J.A. Marshall, M.A. Wolf, and E.M. Wallace J. Org. Chem. 62 1997 367
46. R.F. Schinazi, J.-P. Sommadossi, V. Saalmann, D.L. Cannon, M.-W. Xie, G.C. Hart, G.A. Smith, and E.F. Hahn Antimicrob. Agents Chemother. 34 1990 1061
47. L.J. Stuyver, S. Lostia, M. Adams, J. Mathew, B.S. Pai, J. Grier, P. Thamish, Y. Choi, Y. Chong, H. Choo, C.K. Chu, M.J. Otto, and R.F. Schinazi Antimicrob. Agents Chemother. 46 2002 3854
48. R.F. Schinazi, J. Peters, D.D. Williams, D. Chance, and A.J. Nahmias Antimicrob. Agents Chemother. 22 1982 499