Synthesis, cytostatic and anti-HCV activity of 6-(N-substituted aminomethyl)-, 6-(O-substituted hydroxymethyl)- and 6-(S-substituted sulfanylmethyl)purine nucleosides

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 5, 2008, Pages 2329-2366

  Šilhár, Peter ^a   Hocek, Michal ^a   Pohl, Radek ^a   Votruba, Ivan ^a   Shih, I hung ^b   Mabery, Eric ^b   Mackman, Richard ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b GILEAD SCIENCES   (United States)

Author keywords

Antivirals; Cytostatics; Nucleosides; Purines

Indexed keywords

6 (AZIDOMETHYL) 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 (BENZYLSULFANYLMETHYL) 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 (MERCAPTOMETHYL) 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 (METHOXYMETHYL) 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(2 ACETYLHYDRAZINYL)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(MORPHOLIN 4 YL)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(MORPHOLINO 4 YL)METHYL] 9 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)PURINE; 6 [(N ACETYL N BENZYL)AMINOMETHYL] 9 (2 DEOXY BETA DEXTRO ERYHTRO PENTOFURANOSYL)PURINE; 6 [(N ACETYL N BENZYL)AMINOMETHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(N ACETYL N CYCLOHEXYL)AMINOMETHYL] 9 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)PURINE; 6 [(N ACETYL N CYCLOHEXYL)AMINOMETHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(N ACETYL N CYCLOPROPYLAMINO)METHYL] 9 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)PURINE; 6 [(N ACETYL N CYCLOPROPYLAMINO)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(N ACETYL N METHYL)AMINOMETHYL] 9 (2 DEOXY BETA DEXTRO ERYHTRO PENTOFURANOSYL)PURINE; 6 [(N ACETYL N METHYL)AMINOMETHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(N BENZYL N METHYLAMINO)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(N METHYL N PHENYLAMINO)METHYL] 9 (2 DEXOY BETA DEXTRO ERYTHRO PENTOFURANOSYL)PURINE; 6 [(N METHYL N PHENYLAMINO)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(N,N DIMETHYLAMINO)METHYL] 9 (2 DEOXY BETA DEXTRO ERYHTRO PENTOFURANOSYL)PURINE; 6 [(N,N DIMETHYLAMINO)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(PIPERIDIN 1 YL)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [(PIPERIDIN 1 YL)METHYL] 9 (DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)PURINE; 6 [(THIAZOLIDIN 3 YL)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [N (HYDROXYCARBONYLMETHYL)AMINOMETHYL] 9 (BETA DEXTRO FIBOFURANOSYL)PURINE; 6 [N,N (DIISOPROPYLAMINO)METHYL] 9 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL]PURINE; 6 [N,N (DIISOPROPYLAMINO)METHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; 6 [N,N BIS(2 HYDROXYETHYL)AMINOMETHYL] 9 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)PURINE; 6 [N,N BIS(2 HYDROXYETHYL)AMINOMETHYL] 9 (BETA DEXTRO RIBOFURANOSYL)PURINE; PURINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE ARREST; CELL CYCLE S PHASE; CHEMICAL REACTION; CONTROLLED STUDY; CYTOSTASIS; DRUG SELECTIVITY; DRUG SYNTHESIS; HEPATITIS C VIRUS; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

AMINATION; ANIMALS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; CYTOSTATIC AGENTS; HEPACIVIRUS; HUMANS; HYDROXYLATION; MESYLATES; METHYLATION; MICE; MOLECULAR STRUCTURE; PURINE NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS;

HEPATITIS C VIRUS;

EID: 40749087170     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.11.067     Document Type: Article

References (32)

1. Hocek M., Holý A., Votruba I., and Dvořáková H. J. Med. Chem. 43 (2000) 1817-1825
2. Hocek M., Holý A., Votruba I., and Dvořáková H. Collect. Czech. Chem. Commun. 66 (2001) 483-499
3. Hocek M., Nauš P., Pohl R., Votruba I., Furman P.A., Tharnish P.M., and Otto M.J. J. Med. Chem. 48 (2005) 5869-5873
4. Gundersen L.-L., Nissen-Meyer J., and Spilsberg D. J. Med. Chem. 45 (2002) 1383-1386
5. Bakkestuen A.K., Gundersen L.-L., and Utenova B.T. J. Med. Chem. 48 (2005) 2710-2723
6. Cocuzza A.J., Chidester D.R., Culp S., Fitzgerald L., and Gilligan P. Bioorg. Med. Chem. Lett. 9 (1999) 1063-1066
7. Chang L.C.W., Spanjersberg R.F., von Frijtag Drabbe Kunzel J.K., Mulder-Krieger T., Brussee J., and IJzerman A.P. J. Med. Chem. 49 (2006) 2861-2867
8. Šilhár P., Pohl R., Votruba I., and Hocek M. Org. Lett. 6 (2004) 3225-3228
9. Šilhár P., Pohl R., Votruba I., and Hocek M. Collect. Czech. Chem. Commun. 70 (2005) 1669-1695
10. Šilhár P., Pohl R., Votruba I., and Hocek M. Collect. Czech. Chem. Commun. 71 (2006) 788-803
11. Hocek M., Šilhár P., and Pohl R. Collect. Czech. Chem. Commun. 71 (2006) 1484-1496
12. Čapek P., Pohl R., and Hocek M. J. Org. Chem. 69 (2004) 7985-7988
13. Čapek P., Pohl R., and Hocek M. J. Org. Chem. 70 (2005) 8001-8008
14. Hocek M. Eur. J. Org. Chem. (2003) 245-254
15. Agrofoglio L.A., Gillaizeau I., and Saito Y. Chem. Rev. 103 (2003) 1875-1916
16. Šilhár P., Pohl R., Votruba I., and Hocek M. Org. Biomol. Chem. 3 (2005) 3001-3007
17. Šilhár P., Pohl R., Votruba I., and Hocek M. Synthesis (2006) 1848-1852
18. Giner-Sorolla A., and Bendich A. J. Am. Chem. Soc. 80 (1958) 3932-3937
19. Herdewijn P., Van Aerschot A., and Pfleiderer W. Synthesis (1989) 961-962
20. Matsuda A., Satoh K., Miyasaka T., and Ueda T. Chem. Pharm. Bull. 32 (1984) 2048-2051
21. Hocek M., Masoji{dotless}́dková M., Holý A., Andrei G., Snoeck R., Balzarini J., and De Clercq E. Collect. Czech. Chem. Commun. 61 (1996) 1525-1537
22. Chaman E.S., and Golovchinskaya E.S. J. Gen. Chem. USSR (Engl. Transl.) 33 (1963) 3269-3274
23. Suemune H., and Miyasaka T. Nucleic Acids Res. Symp. Ser. 12 (1983) 1-4
24. Hocek M., Masoji{dotless}́dková M., and Holý A. Tetrahedron 53 (1997) 2291-2302
25. Stevens M.A., Giner-Sorolla A., Smith H., and Brown G.B. J. Org. Chem. 27 (1962) 567-572
26. Giner-Sorolla A., and Bendich A. J. Med. Chem. 8 (1965) 667-672
27. For a general review on reductive aminations, see. Larock R.C. Comprehensive Organic Transformations (1989), VCH Publishers 421-425
28. Roehm N.W., Rodgers GH., Hatfield S.M., and Glasebrook A.L. J. Immunol. Methods. 142 (1991) 257-265
29. Agarwal R.P., and Parks Jr. R.E. Adenosine deaminase from human erythrocytes. In: Hoffe P.A., and Jones M.E. (Eds). Methods in Enzymology 51 (1978), Academic Press 502-507
30. Stuyver L.J., Whitaker T., McBrayer T.R., Hernandez-Santiago B.I., Lostia S., Tharnish P.M., Ramesh M., Chu C.K., Jordan R., Shi J.X., Rachakonda S., Watanabe K.A., Otto M.J., and Schinazi R.F. Antimicrob. Agents Chemother. 47 (2003) 244-254
31. Scudiero D.A., Shoemaker RH., Paull K.D., Monks A., Tierney S., Nofziger TH., Currens M.J., Seniff D., and Boyd M.R. Cancer Res. 48 (1988) 4827-4833
32. Lohmann V., Korner F., et al. Science 285 (1999) 110-113