Synthesis and antiviral evaluation of (-)-3′-methylcarbovir, (-)-3′-methylabacavir, and modified purine analogues

Synthesis

Volumn , Issue 2, 2009, Pages 290-296

  Brémond, Paul ^a   Audran, Gérard ^a   Monti, Honoré ^a   De Clercq, Erik ^b   Pannecouque, Christophe ^b  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral agents; Azides; Carbocyclic nucleosides; Nucleobases; Stereoselective synthesis

Indexed keywords

ANTIVIRAL AGENTS; AZIDES; CARBOCYCLIC NUCLEOSIDES; NUCLEOBASES; STEREOSELECTIVE SYNTHESIS;

CARBOXYLATION; DERIVATIVES; NITROGEN COMPOUNDS; NUCLEOTIDES; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

3' METHYLABACAVIR; 3' METHYLCARBOVIR; ANTIVIRUS AGENT; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; NONHUMAN; QUANTUM YIELD; STRUCTURE ACTIVITY RELATION;

EID: 63849205569     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083213     Document Type: Article

References (48)

1. For reviews, see: (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
2. (b) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
3. (c) Ferrero, M.; Gotor, V. Chem. Rev. 2000, 100, 4319.
4. (d) Zu, X. F. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 651.
5. (e) Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875.
6. (f) Rodriguez, J. B.; Comin, M. Mini-Rev. Med. Chem. 2003, 3, 95.
7. Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550.
8. (a) Bennett, L. L.; Shannon, W. M.; Allan, P. W.; Arnett, G. Ann. N. Y. Acad. Sci. 1975, 255, 342.
9. (b) De Clercq, E. J. Med. Chem. 2005, 48, 1297.
10. (a) Vince, R.; Hua, M.; Brownell, J.; Daluge, S. M.; Lee, F. C.; Shannon, W. M.; Lavelle, G. C.; Qualls, J.; Weislow, O. S.; Kiser, R.; Canonico, P. G.; Schultz, R. H.; Narayanan, V. L.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Biochem. Biophys. Res. Commun. 1988, 156, 1046.
11. (b) Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
12. (c) Vince, R. Nucleic Acids Symp. Ser. 1991, 25, 193.
13. (d) Parker, W. B.; Shaddix, S. C.; Bowdon, B. J.; Rose, L. M.; Vince, R.; Shannon, W. M.; Bennett, L. L. Antimicrob. Agents Chemother. 1993, 37, 1004.
14. (a) Daluge, S. M. US Patent 5034394, 1991.
15. (b) Good, S. S.; Daluge, S. M.; Ching, S. V.; Ayers, K. M.; Mahony, W. B.; Faletto, M. B.; Domin, B. A.; Owens, B. S.; Dornsife, R. E.; McDowell, J. A.; Lafon, S. W.; Symonds, W. T. Antiviral Res. 1995, 26, A229.
16. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192.
17. (d) Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; St. Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082.
18. (e) Hervey, P. S.; Perry, L. M. Drugs 2000, 60, 447.
19. (f) Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 297.
20. (a) Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. J. Med. Chem. 1992, 35, 1882.
21. (b) Tanaka, M.; Norimine, Y.; Fujita, T.; Suemune, H. J. Org. Chem. 1996, 61, 6952.
22. Wang, J.; Jin, Y.; Rapp, K. L.; Bennett, M.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2005, 48, 3736.
23. Wang, J.; Jin, Y.; Rapp, K. L.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2007, 50, 1828.
24. Huang, W.; Miller, J. M.; De Clercq, E.; Balzarini, J. Org. Biomol. Chem. 2007, 5, 1164.
25. Sriram, D.; Yogeeswari, P.; Myneedu, N. S.; Saraswat, V. Bioorg. Med. Chem. Lett. 2006, 16, 2127.
26. Brémond, P.; Audran, G.; Aubin, Y.; Monti, H. Synlett 2007, 1124.
27. (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.
28. (b) Trost, B. M. J. Org. Chem. 2004, 69, 5813.
29. Audran, G.; Acherar, S.; Monti, H. Eur. J. Org. Chem. 2003, 5, 92.
30. Saville-Stones, E. A.; Lindell, S. D.; Jennings, N. S.; Head, J. C.; Ford, M. I. J. Chem. Soc., Perkin Trans. 1 1991, 2603.
31. Falck-Pedersen, M. L.; Benneche, T.; Undheim, K. Acta Chem. Scand. 1993, 47, 63.
32. (a) Shealy, Y. F.; Clayton, J. D. J. Pharm. Sci. 1973, 62, 1432.
33. (b) Taylor, S. J. C.; Sutherland, A. G.; Lee, C.; Wisdow, R.; Thomas, S.; Roberts, S. M.; Evans, C. T. J. Chem. Soc., Chem. Commun. 1990, 1120.
34. (c) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589.
35. Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886.
36. It is a general observation that the cis-1,4-disubstituted cyclopentenes present differences in the range of 1 ppm in the chemical shifts of their H-5 protons with the upfield proton assigned as syn to both substituents. Alternatively, the difference does not usually exceed 0.3 ppm for the transisomer, see: Marino, J. P.; Fernandez de la Pradilla, R.; Laborde, E. J. Org. Chem. 1987, 52, 4893; and references cited therein.
37. Anti-HIV Nucleosides: Past, Present and Future; Mitsuya, H., Ed.; R. G. Landes Co.: Georgetown TX, 1997.
38. (a) Montgomery, J. A.; Temple, C. Jr. J. Am. Chem. Soc. 1957, 79, 5238.
39. (b) Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc. 1966, 88, 3885.
40. (c) Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc. 1969, 91, 3075.
41. (d) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049.
42. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. J. Virol. Methods 1988, 20, 309.
43. Popovic, M.; Sarngadharan, M. G.; Read, E.; Gallo, R. C. Science 1984, 224, 497.
44. Barrè-Sinoussi, F.; Chermann, J. C.; Rey, F.; Nugeyre, M. T.; Chamaret, S.; Grest, J.; Dauget, C.; Axler-Blin, C.; Vezinet-Brun, F.; Rouzioux, C.; Rozenbaum, W.; Montagnier, L. Science 1983, 220, 868.
45. Miyoshi, I.; Taguchi, H.; Kobonishi, I.; Yoshimoto, S.; Ohtsuki, Y.; Shiraishi, Y.; Akagi, T. Gann Monogr. 1982, 28, 219.
46. De Clercq, E.; Descamps, J.; Verhelst, G.; Walker, R. T.; Jones, A. S.; Torrence, P. F.; Shugar, D. J. Infect. Dis. 1980, 141, 563.
47. De Clercq, E. Antimicrob. Agents Chemother. 1985, 28, 84.
48. De Clercq, E.; Holy, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. Nature 1986, 323, 464.