Synthesis and anti-HIV activity of GS-9148 (2′-Fd4AP), a novel nucleoside phosphonate HIV reverse transcriptase inhibitor

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 3, 2008, Pages 1120-1123

  Boojamra, Constantine G ^a   Mackman, Richard L ^a   Markevitch, David Y ^a   Prasad, Vidya ^a   Ray, Adrian S ^a   Douglas, Janet ^a   Grant, Deborah ^a   Kim, Choung U ^a   Cihlar, Tomas ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

Antiviral; HIV; Phosphonate; Resistance

Indexed keywords

2',3' DIDEHYDRO 2',3' DIDEOXY 2' FLUORO 5' O PHOSPHONOMETHYLADENOSINE; ANTIVIRUS AGENT; MITOCHONDRIAL DNA; MUTANT PROTEIN; RNA DIRECTED DNA POLYMERASE INHIBITOR; TENOFOVIR DISOPROXIL; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ANTIVIRAL SUSCEPTIBILITY; ARTICLE; CELL STRAIN HEPG2; CONTROLLED STUDY; DNA CONTENT; DRUG DESIGN; DRUG EFFECT; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SAFETY; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; MITOCHONDRIAL TOXICITY; MOLECULE; NONHUMAN; VIRUS TYPING; WILD TYPE;

ANTI-HIV AGENTS; DNA, MITOCHONDRIAL; FLUORINE; GUANOSINE; HIV REVERSE TRANSCRIPTASE; HUMANS; MOLECULAR STRUCTURE; NUCLEOSIDES; PHOSPHONIC ACIDS; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; ZIDOVUDINE;

EID: 38749083033     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.125     Document Type: Article

References (33)

1. Saliba G., and Yeni P. Pathol. Biol. 54 (2006) 545
2. Schinazi R.F., Hernandez-Santiago B.I., and Hurwitz S.J. Antiviral Res. 71 (2006) 322
3. Gilbert D.N., Moellering Jr. R.C., Eliopoulos G.M., and Sande M.A. The Sanford Guide to Antimicrobial Therapy. 37th ed. (2007), Antimicrobial Therapy, Inc., Sperryville, VA pp 151-158
4. Updated HIV treatment guidelines available at: . Also see Ref. 1.
5. Gallant J.E., DeJesus E., Arribas J.R., Pozniak A.L., Gazzard B., Campo R.E., Lu B., McColl D., Chuck S., Enejosa J., Toole J.J., Cheng A.K., et al. N. Eng. J. Med. 354 (2006) 251
6. McColl, D. #393, 7th International Congress on HIV Drug Therapy, Glasgow, 2004.
7. Johnson V.A., Brun-Vézinet F., Clotet B., Conway B., Kuritzkes D.R., Pillay D., Schapiro J.M., Telenti A., and Richman D. Top. HIV Med. 13 (2005) 125
8. Zemlicka J., Gasser R., Freisler J.V., and Horwitz J.P. J. Am. Chem. Soc. 94 (1972) 3213
9. Kim C.U., Luh B.Y., and Martin J.C. J. Org. Chem. 56 (1991) 2642
10. Mackman R.L., Boojamra C.G., Prasad V., Zhang L., Lin K.-Y., Petrakovsky O., Babusis D., Chen J., Douglas J., Grant D., Hui H.C., Kim C.U., Markevitch D.Y., Vela J., Ray A., and Cihlar T. Bioorg. Med. Chem. Lett. 17 (2007) 6785
11. Lim S.E., Ponamarev M.V., Longley M.J., and Copeland W.C. J. Mol. Biol. 329 (2003) 45
12. Antiviral Ther. 10 Suppl. 2 (2005)
13. Lewis W., Day B.J., and Copeland W.C. Nat. Rev., Drug Disc. 2 (2003) 812
14. Lund K.C., and Wallace K.B. Cadiovascular Toxicol. 4 (2004) 217
15. Lewis W. Antiviral Res. 58 (2003) 189
16. Lewis W., Kohler J.J., Hosseini S.H., Haase C.P., Copeland W.C., Bienstock R.J., Ludaway T., McNaught J., Russ R., Stuart T., and Santoianni R. AIDS 20 (2006) 675
17. Johnson A.A., Ray A.S., Hanes J., Suo Z., Colacino J.M., Anderson K.S., and Johnson K.A. J. Biol. Chem. 276 (2001) 40847
18. Cihlar, T.; Ray, A. S.; Boojamra, C. G.; Zhang, L.; Hui, H.; Laflamme, G.; Vela, J. E.; Grant, D.; Chen, J.; Myrick, F.; White, K. L.; Gao, Y.; Lin, K.-Y.; Douglas, J.; Parkin, N.; Carey, A.; Pakdaman, R.; Mackman, R. L. Antimicrob. Agents Chemother. 2007, in press, doi:10.1128/AAC.01215.07.
19. Murakami E., Ray A.S., Schinazi R.F., and Anderson K.S. Antiviral Res. 62 (2004) 57
20. Wong-Kai-In P., Parkes K.E.B., Kinchington D., Galpin S., Hope A.L., Roberts N.A., Martin J.A., Merrett J.H., Machin P., and Thomas G. Nucleosides Nucleotides 10 (1991) 401
21. Tsai C.-H., Doong S.-L., Johns D.G., Driscoll J.S., and Cheng Y.-C. Biochem. Pharmacol. 48 (1994) 1477
22. Kazimierczuk Z., Cottam H.B., Revankar G.R., and Robins R.K. J. Am. Chem. Soc. 106 (1984) 6379
23. Hanna N.B., Ramasamy K., Robins R.K., and Revankar G.R. J. Heterocycl. Chem. 25 (1988) 1899
24. Tann C.H., Brodfuehrer P.R., Brundidge S.P., Sapino Jr. C., and Howell H.G. J. Org. Chem. 50 (1985) 3644
25. Hanessian S., and Vatèle J.-M. Tetrahedron Lett. 22 (1981) 3579
26. Schaerer O.D., and Verdine G.L. J. Am. Chem. Soc. 117 (1995) 10781
27. Henn T.F.G., Garnett M.C., Chhabra S.R., Bycroft B.W., and Baldwin R.W. J. Med. Chem. 36 (1993) 1570
28. Rosowsky A., Kim S.-H., Trites D., and Wick M. J. Med. Chem. 25 (1982) 1034
29. Jung M.E., and Toyota A. J. Org. Chem. 66 (2001) 2624
30. Lee K., Choi Y., Gumina G., Zhou W., Schinazi R.F., and Chu C.K. J. Med. Chem. 45 (2002) 1313
31. Chambers D.J., Evans G.R., and Fairbanks A.J. Tetrahedron Lett. 44 (2003) 5221
32. McCarthy J.R., Matthews D.P., and Barney C.L. Tetrahedron Lett. 31 (1990) 973
33. Freeman G.A., Rideout J.L., Miller W.H., and Reardon J.E. J. Med. Chem. 35 (1992) 3192