Synthesis of isomeric nucleoside phosphonates: Cyclic analogs of the anti-HIV active compound, PMEA

Tetrahedron

Volumn 55, Issue 40, 1999, Pages 11803-11818

  Zheng, Xiaoping ^a   Nair, Vasu ^a  

^a E11 SSH   (United States)

Author keywords

Anti HIV activity; Cyclic phosphonates; Isonucleosides; NMR data; Stereoselective synthesis

Indexed keywords

9 (3 FLUORO 2 PHOSPHONOMETHOXYPROPYL)ADENINE; ADEFOVIR; ADENINE DERIVATIVE; ANTIRETROVIRUS AGENT; ANTIVIRUS AGENT; NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TENOFOVIR;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; ISOMERISM; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0033213912     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00681-X     Document Type: Article

References (31)

1. Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. USA, 1985, 82, 7096-7100.
2. Mitsuya, H.; Broder, S. Proc. Natl. Acad Sci. USA, 1986, 83, 1911-1915.
3. Yarchoan, R.; Mitsuya, H.; Thomas, R. V.; Pluda, J. M.; Hartman, N. R.; Perno, C-F.; Marczyk, K. S.; Allain, J-P.; Johns, D.; Broder, S. Science 1989, 245, 412-415.
4. Mitsuya, H.; Yarchoan, R.; Broder, S. Science 1990, 249, 1533-1544.
5. De Clercq, E. J. Med. Chem. 1995, 38, 2491-2517, and references therein.
6. Soudeyns, H.; Yao, X.-J.; Gao, Q,; Belleau, B.; Kraus, J.-L.; Nguyen-Ba, N.; Spira, B.; Wainberg, M. A. Antimicrob. Agents Chemother. 1991, 35, 1386-1390.
7. Schinazi, R. F.; Chu, C. K.; Peck, A.; McMillian, A.; Mathis, R.; Cannon, D.; Jeong, L-S.; Beach, J. W.: Choi, W-B.; Yeola, S.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 672-676.
8. Hao, Z.; Cooney, D. A.; Hartman, N. R.; Perno, C-F.; Fridland, A.; DeVico, A. L.; Sarngadharan, M. G.; Broder, S.; Johns, D. G. Mol. Pharmacol. 1988, 34, 431-435.
9. Cooney, D. A.; Ahluwalia, G.; Mitsuya, H.; Fridland, A.; Johnson, M. A.; Hao, Z.; Dalal, M.; Balzarini, J.; Broder, S.; Johns, D. G. Biochem. Pharmacol. 1987, 36, 1765-1768.
10. Huang, P.; Farquhar, D.; Plunkett, W. J. Biol. Chem. 1990, 265, 11914-11918.
11. Nair, V.; Sells, T. B. Biochim. Biophys. Acta 1992, 1119, 201-204.
12. Ho, H-T.; Hitchcock, M. J. M. Antimicrob. Agents Chemother. 1989, 33, 844-849.
13. Sastry, J. K.; Nehete, P. N.; Khan, S.; Nowak, B. J.; Plunkett, W.; Arlinghaus, R. B.; Farquhar, D. Mol. Pharmacol. 1992, 41, 441-445.
14. Puech, F.; Gosselin, G.; Lefebvre, I.; Pompon, A.; Aubertin, A-M.; Kirn, A.; Imbach, J-L. Antiviral Res. 1993, 22, 155-174.
15. Balzarini, J.; Holy, A.; Jindrich, J.; Dvorakova, H.; Hao, Z.; Snoeck, R.; Herdewijn, P.; Johns, D. G.; De Clercq, E. Proc. Natl. Acad. Sci. 1991, 88, 4961-4965.
16. Balzarini, J.; Holy, A.; Jindrich, J.; Naesens, L., Snoeck, R.; Schols, D.; De Clercq, E. Antimicro. Agents Chemther. 1993, 37, 332-338.
17. Balzarini, J.; Hao, Z.; Herdewijn, P.; Johns, D. G.; De Clercq, E. Proc. Natl. Acad Sci. 1991, 88, 1499-1503.
18. De Clercq, E. Clin. Microb. Rev. 1997, 10, 674-693, and references therein
19. Nair, V.; Jahnke, T. S. Antimicrob. Agents and Chemother. 1995, 39, 1017-1029, and references therein.
20. Bolon, P. J.; Sells, T. B.; Nuesca, Z. M.; Purdy, D. F.; Nair, V. Tetrahedron 1994, 50, 7747-7764; Nair, V.; Nuesca, Z. M. J. Am. Chem. Soc. 1992, 114, 7951-7953.
21. Bolon, P. J.; Sells, T. B.; Nuesca, Z. M.; Purdy, D. F.; Nair, V. Tetrahedron 1994, 50, 7747-7764; Nair, V.; Nuesca, Z. M. J. Am. Chem. Soc. 1992, 114, 7951-7953.
22. Nair, V.; St. Clair, M.; Reardon, J. E.; Krasny, H. C.; Hazen, R. J.; Paff, M. T.; Boone, L. R.; Tisdale, M.; Najera, I.; Dornsife, R. E.; Everett, D. R.; Borroto-Esoda, K.; Yale, J. L.; Zimmerman, T. P.; Rideout, J. L. Antimicrob. Agents and Chemother. 1995, 39, 1993-1999.
23. Albrecht, H. P.; Jones, G. H.; Moffatt, J. G. Tetrahedron 1984, 40, 79-87.
24. Jones, G. H.; Moffatt, J. G., J. Am. Chem. Soc. 1968, 90, 5337-5342.
25. Montgomery, J. A.; Laseter, A. G.; Hewson, K. J. Heterocycl. Chem. 1974, 11, 211-219.
26. Secrist, J. A.; Riggs, R. M.; Comber, R. N.; Montgomery, J. A. Nucleosides and Nucleotides, 1992, 11, 947-954.
27. Serra, C.; Dewynter, G.; Montero, J-L.; Imbach, J-L. Tetrahedron 1994, 50, 8427-8444.
28. Kofoed, T.; Ismail, A. E.; Pederson, E. B.; Nielsen, C. Societe Chimique de France Bulletin 1997, 59-65.
29. Meyers, A. I.; Lawson, J. P.; Walker, D. G.; Linderman, R. J. J. Org. Chem. 1986, 51, 5111-5123.
30. Ohler, E.; Zbiral, E. Synthesis 1991, 357-359.
31. Evelyn, L.; Hall, L. D.; Lynn, L.; Steiner, P. R.; Stokes, D. H. Carbohydrate Research 1973, 27, 21-27.