Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

Synthesis

Volumn , Issue 8, 2006, Pages 1313-1324

  Ludek, Olaf R ^a   Krämer, Tobias ^a   Balzarini, Jan ^b   Meier, Chris ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Carbocycles; Hydroborations; Mitsunobu reaction; Nucleosides; Stereoselective synthesis

Indexed keywords

BIOCONVERSION; ISOMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CARBOCYCLES; HYDROBORATIONS; MITSUNOBU REACTION; NUCLEOSIDES; STEREOSELECTIVE SYNTHESIS;

DRUG PRODUCTS;

1 (3' HYDROXY 2' HYDROXYMETHYLCYCLOPENTANYL)THYMINE; 1 (3' HYDROXY 2' HYDROXYMETHYLCYCLOPENTYL)THYMINE; 1 (6' CARBA 2' DESOXY ALPHA DEXTRO PENTOFURANOSYL)THYMINE; 1 (6' CARBA 2' DESOXY BETA DEXTRO THREO PENTOFURANOSYL)THYMINE; 1 BENZYLOXY 2 BENZYLOXYMETHYLCYCLOPENT 3 ENE; ABACAVIR; CARBOCYCLIC NUCLEOSIDE; CARBOVIR; CYCLOPENTANE; CYCLOPENTENE DERIVATIVE; ENTECAVIR; NUCLEOTIDE; PYRIMIDINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; HYDROBORATION; LIPOPHILICITY; MITSUNOBU REACTION; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; SYNTHESIS; VIRUS REPLICATION;

EID: 33646240368     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926411     Document Type: Article

References (51)

1. For selected reviews, see (a) De Clercq, E. Ann. New York Acad. Sci. 1994, 438.
2. (b) Nair, V.; Jahnke, T. S. Antimicrob. Agents Chemother. 1995, 39, 1017.
3. (c) Wilson, L. J.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis 1995, 1465.
4. (d) Pan, S.; Amankulor, N. M.; Zhao, K. Tetrahedron 1998, 54, 6587.
5. (e) Chu, C. K. Nucleic Acids Symp. Ser. 1996, 35, 1.
6. (f) Mitsuya, H. Anti-HIV Nucleosides: Past, Present and Future: Landes: Texas, 1997.
7. (a) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
8. (b) De Clercq, E. J. Med. Chem. 1995, 38, 2491.
9. (c) De Clercq, E. Nucleosides Nucleotides 1994, 13, 1271.
10. (d) Naesens, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Neyts, J.; De Clercq, E. Antivir. Chem. Chemother. 1997, 8, 1.
11. (e) Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.; Shigeta, S.; Matsuda, A. J. Med. Chem. 1999, 42, 2901.
12. (f) Paquette, L. A.; Bibart, R. T.; Seekamp, C. K.; Kahana, A. L. Org. Lett. 2001, 3, 4039.
13. (g) Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 297.
14. For reviews, see (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
15. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
16. (c) Marquez, V. E. In Advances in Antiviral Drug Design, Vol. 2; De Clercq, E., Ed.; JAI Press: Greenwich, 1996, 89.
17. (d) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
18. Marquez, V. E.; Ezzitouni, A.; Russ, P.; Siddiqui, M. A.; Ford, H.; Feldman, R. J.; Mitsuja, H.; George, C.; Barchi, J. J. J. Am. Chem. Soc. 1998, 120, 2780.
19. Béres, J.; Sági, G.; Tömösközi, I.; Gruber, L.; Baitz-Gács, E.; Ötvos, L.; De Clercq, E. J. Med Chem. 1990, 33, 1353.
20. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
21. Bisacchi G. S., Chao S. T., Bachard C., Daris J. P., Innaimo S., Jacobs G. A., Kocy O., Lapointe P., Martel A., Merchant Z., Slusarchyk W. A., Sundeen J. E., Young M. G., Colonno R., Zahler R.; Bioorg. Med. Chem. Lett.; 1997, 7, 127.
22. (a) Balzarini, J.; Baumgartner, H.; Bodenteich, M.; De Clercq, E.; Griengl, H. Nucleosides Nucleotides 1989, 8, 855.
23. (b) Wyatt, P. G.; Anslow, A. S.; Coomber, B. A.; Cousins, R. P. C.; Evans, D. N.; Gilbert, V. S.; Humber, D. C.; Paternoster, I. L.; Sollis, S. L.; Tapolczay, D. J.; Weingarten, G. G. Nucleosides Nucleotides 1995, 14, 2039.
24. Ludek, O. R.; Meier, C. Synthesis 2003, 2101.
25. Biggadike, K.; Borthwick, A. D.; Evans, D.; Exall, A. M.; Kirk, B. E.; Roberts, S. M.; Stephenson, L.; Youds, P. J. Chem. Soc., Perkin Trans. 1 1988, 549.
26. Mitsunobu, O. Synthesis 1981, 1.
27. Herdewijn, P.; Balzarini, J.; De Clercq, E.; Pauwels, R.; Baba, M.; Broder, S.; Vanderhaeghe, H. J. Med. Chem. 1987, 30, 1270.
28. (a) Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975.
29. (b) Brown, H. C.; Jadhav, P. K.; Mandal, A. K. Tetrahedron 1981, 37, 3547.
30. (c) Brown, H. C.; Ayyangar, N. R.; Zweifel, G. J. Org. Chem. 1964, 86, 397.
31. (d) Brown, H. C.; Knights, E. F.; Scouten, C. G. J. Am. Chem. Soc. 1974, 96, 7765.
32. (a) Jenny, T. F.; Previsani, N.; Benner, S. A. Tetrahedron Lett. 1991, 32, 7029.
33. (b) Jenny, T. F.; Horlacher, J.; Previsani, N.; Benner, S. A. Helv. Chim. Acta 1992, 75, 1944.
34. (c) Bonnal, C.; Chavis, C.; Lucas, M. J. Chem. Soc., Perkin Trans. 1994, 1, 1401.
35. (d) Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P. J. Org. Chem. 1995, 60, 1531.
36. (e) Borthwick, A. D.; Crame, A. J.; Exall, A. M.; Weingarten, G. G.; Mahmoudian, M. Tetrahedron Lett. 1995, 36, 6929.
37. (f) Schmitt, L.; Caperelli, C. A. Nucleosides Nucleotides 1997, 16, 2165.
38. (g) Choo, H.; Chong, Y.; Chu, C. K. Org. Lett. 2001, 3, 1471.
39. (h) Comins, D. L.; Jianhua, G. Tetrahedron Lett. 1994, 35, 2819.
40. Cruickshank, K. A.; Jiricny, J.; Reese, C. B. Tetrahedron Lett. 1984, 25, 681.
41. Tomoskozi, I.; Gruber, L.; Baitz Gacs, E.; Otvos, L.; De Clercq, E. J. Med. Chem. 1990, 33, 1353.
42. (a) Meier, C. Mini-Rev. Med. Chem. 2002, 2, 219.
43. (b) Meier, C. Advances in Antiviral Drug Design, Vol. 4; Elsevier: Amsterdam, 2004, 147.
44. Meier, C.; Lorey, M.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1998, 41, 1417.
45. Balzarini, J.; Aquaro, S.; Knispel, T.; Rampazzo, C.; Bianchi, V.; Perno, C.-F.; De Clercq, E.; Meier, C. Mol. Pharmacol. 2000, 58, 928.
46. (a) Meier, C.; Knispel, T.; Marquez, V. E.; Siddiqui, M. A.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1999, 42, 1615.
47. (b) Balzarini, J.; Haller-Meier, F.; De Clercq, E.; Meier, C. Antivir. Chem. Chemother. 2002, 12, 301.
48. (c) Meier, C.; Lomp, A.; Meerbach, A.; Wutzler, P. J. Med. Chem. 2002, 45, 5157.
49. (d) Meier, C.; Habel, L.; Haller-Meier, F.; Lomp, A.; Herderich, M.; Klöcking, R.; Meerbach, A.; Wutzler, P. Antivir. Chem. Chemother. 1998, 9, 389.
50. Wu, S.-Y.; Casida, J. E. Chem. Res. Toxicol. 1992, 5, 680.
51. Gathergood, N.; Knudsen, K. R.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1014.