Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 3, 2008, Pages 1400-1424

  Kuchař, Martin ^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

Conjugate additions; Cytostatic activity; Nucleosides; Purines

Indexed keywords

6 (2 METHOXYETHYL) 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 (2 METHOXYETHYL) 9 (BETA D RIBOFURANOSYL)PURINE; 6 [(1,3 DITHIOLAN 2 YL)METHYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [(1,3 DITHIOLAN 2 YL)METHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (DIBUTYLAMINO)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (DIBUTYLAMINO)VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (DIBUTYLAMINO)VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (DIETHYLAMINO)ETHYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (DIETHYLAMINO)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (DIETHYLAMINO)VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (DIETHYLAMINO)VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (DIMETHYLAMINO)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (DIMETHYLAMINO)VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (DIMETHYLAMINO)VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (METHYLSULFANYL)ETHYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (METHYLSULFANYL)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (MORPHOLINE 4 YL)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (MORPHOLINE 4 YL)VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (MORPHOLINE 4 YL)VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (PIPERIDINE 1 YL)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (PIPERIDINE 1 YL)VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (PIPERIDINE 1 YL)VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (THIAZOLIDINE 1 YL)ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 (THIAZOLIDINE 1 YL)VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 (THIAZOLIDINE 2 YL)VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 [BENZYL(METHYL)AMINO]ETHYL] 9 (BETA D RIBOFURANOSYL)PURINE; 6 [2 [BENZYL(METHYL)AMINO]VINYL] 9 (2 DEOXY BETA D ERYTHROPENTAFURANOSYL)PURINE; 6 [2 [BENZYL(METHYL)AMINO]VINYL] 9 (BETA D RIBOFURANOSYL)PURINE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CYTOSTASIS; DRUG ACTIVITY; DRUG EFFECT; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN;

ALKYLATION; AMINATION; ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CELL SURVIVAL; HEPACIVIRUS; HUMANS; MICE; MOLECULAR STRUCTURE; PURINE NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

HEPATITIS C VIRUS;

EID: 38849135983     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.063     Document Type: Article

References (29)

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. Org. Biomol. Chem. 3 (2005) 3001-3007
11. Šilhár P., Pohl R., Votruba I., and Hocek M. Synthesis (2006) 1848-1852
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. Šilhár, P.; Hocek, M.; Pohl, R.; Votruba, I.; Shih, I.; Mabery, E.; Mackman, R. Bioorg. Med. Chem., submitted for publication.
15. Hocek M. Eur. J. Org. Chem. (2003) 245-254
16. Agrofoglio L.A., Gillaizeau I., and Saito Y. Chem. Rev. 103 (2003) 1875-1916
17. Yus M., and Foueblo F. In: Knochel P. (Ed). Handbook of Functionalized Organometallics, Applications in Synthesis (2005), Wiley-VCH, Weinheim, Germany 18-22
18. An alternative approach to this class of compounds was based on the cross-coupling with the Reformatsky reagent:. Hasni{dotless}́k Z., Šilhár P., and Hocek M. Tetrahedron Lett. 48 (2007) 5589-5592
19. Nagatsugi F., Kawasaki T., Usui D., Maeda M., and Sasaki S. J. Am. Chem. Soc. 121 (1999) 6753-6754
20. Kawasaki T., Nagatsugi F., Ali M.M., Maeda M., Sugiyama K., Hori K., and Sasaki S. J. Org. Chem. 70 (2005) 14-23
21. Ali M.M., Oishi M., Nagatsugi F., Mori K., Nagasaki Y., Kataoka K., and Sasaki S. Angew. Chem. Int. Ed. 45 (2006) 3136-3140
22. Øveras A.T., Bakkestuen A.K., Gundersen L.-L., and Rise F. Acta Chem. Scand. 51 (1997) 1116-1124
23. Liu F., Dalhus B., Gundersen L.-L., and Rise F. Acta Chem. Scand. 53 (1999) 269-279
24. Wang J.-F., Zhang L.-R., Yang Z.-J., and Zhang L.-H. Bioorg. Med. Chem. 12 (2004) 1425-1429
25. Kuchař M., Pohl R., Votruba I., and Hocek M. Eur. J. Org. Chem. (2006) 5083-5098
26. Nauš P., Votruba I., and Hocek M. Collect. Czech. Chem. Commun. 69 (2004) 1955-1970
27. 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
28. Scudiero D.A., Shoemaker R.H., Paull K.D., Monks A., Tierney S., Nofziger T.H., Currens M.J., Seniff D., and Boyd M.R. Cancer Res. 48 (1988) 4827-4833
29. Lohmann V., Korner F., et al. Science 285 (1999) 110-113