Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2′-C-methyladenosine

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 15, 2007, Pages 5219-5229

  Butora, Gabor ^a   Olsen, David B ^a   Carroll, Steven S ^a   McMasters, Daniel R ^a   Schmitt, Christoph ^a   Leone, Joseph F ^a   Stahlhut, Mark ^a   Burlein, Christine ^a   MacCoss, Malcolm ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Adenosine deaminase; Hepatitis C; Hepatitis C virus; Nucleosides; RNA polymerase

Indexed keywords

1 (4 AMINO 5H PYRROLO[3,2 D]PYRIMIDIN 7 YL) 1,4 ANHYDRO 2' C METHYL DEXTRO RIBITOL; 1 (4 AMINOFURO[3,2 D]PYRIMIDIN 7 YL) 1,4 ANHYDRO 2 C METHYL DEXTRO RIBITOL; 2' C METHYL 7 DEAZAADENOSINE; 2' C METHYLADENOSINE; 7 OXA 7,9 DIDEAZA 2' C METHYLADENOSINE; 9 DEAZA 2' C METHYLADENOSINE; ADENOSINE DEAMINASE; ADENOSINE DERIVATIVE; CARBON; NUCLEIC ACID BASE; NUCLEOSIDE; UNCLASSIFIED DRUG; VALOPICITABINE; VIRUS RNA;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CORRELATION ANALYSIS; DEAMINATION; DRUG ACTIVITY; DRUG DEGRADATION; DRUG DESIGN; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS C VIRUS; HYDROGEN BOND; INHIBITION KINETICS; NONHUMAN; RNA REPLICATION; VIRUS INHIBITION;

ADENOSINE; ANTIVIRAL AGENTS; CELL LINE; HEPACIVIRUS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RNA, VIRAL; VIRUS REPLICATION;

HEPATITIS C VIRUS;

EID: 34249933126     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.020     Document Type: Article

References (35)

1. Management of Hepatitis C: 2002. National Institutes of Health Consensus Conference Statement, June 10-12, 2002.
2. Fried M.W., Shiffman M.L., Reddy K.R., Smith C., Marinos G., Goncales Jr. F.L., Haussinger D., Diago M., Carosi G., Dhumeaux D., Craxi A., Lin A., Hoffman J., and Yu J. New Engl. J. Med. 347 (2002) 975
3. McHutchison J.G., Gordon S.C., Schiff E.R., Shiffman M.L., Lee W.M., Rustgi V.K., Goodman Z.D., Ling M.-H., Cort S., Albrecht J.K., and The Hepatitis Interventional Therapy Group. New Engl. J. Med. 339 (1998) 1485
4. Moradpour D., and Blum H.E. Liver Int. 24 (2004) 519
5. Hügle T., and Cerny A. Rev. Med. Virol. 13 (2003) 361
6. Locarnini S.A., and Bartholomeusz A. J. Gastroent. Hepatol. 17 (2002) 442
7. Pierra C., Benzaria S., Amador A., Moussa A., Mathieu S., Storer R., and Gosselin G. Nucleosides, Nucleotides Nucleic Acids 24 (2005) 767
8. el Kouni M.H. Curr. Pharm. Design. 8 (2002) 581
9. Carroll S.S., Tomassini J.E., Bosserman M., Getty K., Stahlhut M.W., Eldrup A.B., Bhat B., Hall D., Simcoe A.L., LaFemina R., Rutkowski C.A., Wolanski B., Yang Z., Migliaccio G., De Francesco R., Kuo L.C., MacCoss M., and Olsen D.B. J. Biol. Chem. 278 (2003) 11979
10. Eldrup A.B., Allerson C.R., Bennett C.F., Bera S., Bhat B., Bhat N., Bosserman M.R., Brooks J., Burlein C., Carroll S.S., Cook P.D., Getty K.L., MacCoss M., McMasters D.R., Olsen D.B., Prakash T.P., Prhavc M., Song Q.L., Tomassini J.E., and Xia J. J. Med. Chem. 47 (2004) 2283
11. Olsen D.B., Eldrup A.B., Bartholomew L., Bhat B., Bosserman M.R., Ceccacci A., Colwell L.F., Fay J.F., Flores O.A., Getty K.L., Grobler J.A., LaFemina R.L., Markel E.J., Migliaccio G., Prhavc M., Stahlhut M.W., Tomassini J.E., MacCoss M., Hazuda D.J., and Carroll S.S. Antimicrob. Agents Ch. 48 (2004) 3944
12. Eldrup A.B., Prhavc M., Brooks J., Bhat B., Prakash T.P., Song Q., Bera S., Bhat N., Dande P., Cook P.D., Bennett C.F., Carroll S.S., Ball R.G., Bosserman M., Burlein C., Colwell L.F., Fay J.F., Flores O.A., Getty K., LaFemina R.L., Leone J., MacCoss M., McMasters D.R., Tomassini J.E., Von Langen D., Wolanski B., and Olsen D.B. J. Med. Chem. 47 (2004) 5284
13. Sideraki V., Mohamedali K.A., Wilson D.K., Chang Z., Kellems R.E., Quiocho F.A., and Rudolph F.B. Biochemistry 35 (1996) 7862
14. Liu M.C., Luo M.Z., Mozdziesz D.E., and Sartorelli A.C. Nucleosides, Nucleotides Nucleic Acids 24 (2005) 45
15. Girgis N.S., Michael M.A., Smee D.F., Alaghamandan H.A., Robins R.K., and Cottam H.B. J. Med. Chem. 33 (1990) 2750
16. Lim M.I., and Klein R.S. Tetrahedron Lett. 22 (1981) 25
17. Bhattacharya B.K., Lim M.I., Otter B.A., and Klein R.S. Tetrahedron Lett. 27 (1986) 815
18. Bio M.M., Xu F., Waters M., Williams J.M., Savary K.A., Cowden C.J., Yang C., Buck E., Song Z.J., Tschaen D.M., Volante R.P., Reamer R.A., and Grabowski E.J.J. J. Org. Chem. 69 (2004) 6257
19. Xu F., Simmons B., Savary K., Yang C., and Reamer R.A. J. Org. Chem. 69 (2004) 7783
20. Naimi E., Kumar P., Mcewan A.J.B., and Wiebe L.I. Nucleosides, Nucleotides Nucleic Acids 24 (2005) 173
21. Guibe F. Tetrahedron 54 (1998) 2967
22. Guibe F. Tetrahedron 53 (1997) 13509
23. Minakawa N., Kato Y., Uetake K., Kaga D., and Matsuda A. Tetrahedron 59 (2003) 1699
24. Laguzza B.C., and Ganem B. Tetrahedron Lett. 22 (1981) 1483
25. Yang S.G., Park M.Y., and Kim Y.H. Synlett (2002) 492
26. Taniguchi T., and Ogasawara K. Angew. Chem. Int. Ed. 37 (1998) 1136
27. De Bernardo S., and Weigele M. J. Org. Chem. 42 (1977) 109
28. Lim M.I., Klein R.S., and Fox J.J. Tetrahedron Lett. 21 (1980) 1013
29. Kirsch G., Cagniant D., and Cagniant P. J. Heterocycl. Chem. 19 (1982) 443
30. Lohmann V., Korner F., Koch J., Herian U., Theilmann L., and Bartenschlager R. Science 285 (1999) 110
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M.A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J., Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johns, B. Gaussian 03, Revision C.01.
32. Wavefunction, Inc., Irvine, CA.
33. Cristalli G., Costanzi S., Lambertucci C., Lupidi G., Vittori S., Volpini R., and Camaioni E. Med. Res. Rev. 21 (2001) 105
34. Wang Z.M., and Quiocho F.A. Biochemistry 37 (1998) 8314
35. Nobeli I., Price S.L., Lommerse J.P.M., and Taylor R. J. Comput. Chem. 18 (1997) 2060