Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: Synthesis and antiviral evaluation

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 15, 2004, Pages 4245-4252

  Kifli, Nurolaini ^a   De Clercq, Erik ^b   Balzarini, Jan ^b   Simons, Claire ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral activity; Base modified nucleosides; Imidazo 1,2 c pyrimidine 2 carbonitrile; Imidazo 1,2 c pyrimidine 5 one

Indexed keywords

2 AMINOMETHYL 6 (2,3,5 TRI O TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL 5 OXO 5,6 DIHYDROIMIDAZO[1,2 C]PYRIMIDIN 5 ONE; 6 (BETA DEXTRO RIBOFURANOSYL) 2 6H IMIDAZO[1,2 C]PYRIMIDIN 5 ONE; 6 (BETA DEXTRO RIBOFURANOSYL) 2 ETHYL 6H IMIDAZO[1,2 C]PYRIMIDIN 5 ONE; 6 (BETA DEXTRO RIBOFURANOSYL) 2 METHYL 6H IMIDAZO[1,2 C]PYRIMIDIN 5 ONE; 6 (BETA DEXTRO RIBOFURANOSYL) 2 PHENYL 6H IMIDAZO[1,2 C]PYRIMIDIN 5 ONE; 6 (BETA DEXTRO RIBOFURANOSYL) 5 OXO 5,6 DIHYDROIMIDAZO[1,2 C]PYRIMIDINE 2 CARBONITRILE; IMIDAZO[1,2 C]PYRIMIDINE; NUCLEOSIDE DERIVATIVE; PHOSPHOTRANSFERASE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; ISOMERIZATION; MOLECULAR RECOGNITION; NONHUMAN; VIRUS STRAIN;

ANIMALS; ANTIVIRAL AGENTS; CERCOPITHECUS AETHIOPS; CYTOPATHOGENIC EFFECT, VIRAL; HELA CELLS; HUMANS; IMIDAZOLES; MOLECULAR CONFORMATION; NUCLEOSIDES; PYRIDAZINES; VERO CELLS;

CUCUMBER MOSAIC VIRUS;

EID: 3042750209     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.05.017     Document Type: Article

References (22)

1. Simons C. Nucleoside Mimetics: Their Chemistry and Biological Properties. Advanced Chemistry Text Series. Vol. 3:2001;Gordon and Breach Science, Amsterdam. p 192
2. Kinchington D., Balzarini J., De Clercq E., Daluge S., Field H.J. Int. Antivir. News. 8:2000;155-164
3. Harwood E.A., Hopkins P.B., Sigurdsson S.T. J. Org. Chem. 65:2000;2959-2964
4. Guickan K.M., Morales J.C., Kool E.T. J. Org. Chem. 63:1998;9652-9656
5. Rosler A., Pfleiderer W. Helv. Chim. Acta. 80:1997;1869-1881
6. Fisher B., Kabha E., Gendron F.-P., Beaudoin A.R. Nucleos. Nucleot. Nucl. 19:2000;1033-1054
7. Loakes D., Brown D.M., Mahmood N., Balzarini J., De Clercq E. Antivir. Chem. Chemother. 6:1995;371-378
8. McGuigan C., Yarnold C.J., Jones G., Velaquez S., Barucki H., Brancale A., Andrei G., Snoeck R., De Clercq E., Balzarini J. J. Med. Chem. 42:1999;4479-4484
9. Mansour T., Evans C.A., Charron M., Korba B.E. Bioorg. Med. Chem. Lett. 7:1997;303-308
10. Mansour T., Evans C.A., Siddiqui M.A., Charron M., Zacharie B., Nguyen-Ba N., Lee N., Korba B.E. Nucleos. Nucleot. 16:1997;993-1001
11. Patil V.D., Wise D.S., Townsend L.B., Bloch A. J. Med. Chem. 17:1974;1282-1285
12. Patil V.D., Wise D.S., Wotring L.L., Bloomer L.C., Townsend L.B. J. Med. Chem. 28:1985;423-427
13. Secrist J.A., Barrio J.R., Leonard N.J., Weber G. Biochemistry. 11:1972;3499-3506
14. Barrio J.R., Dammann L.G., Kirkegaard L.H., Switzer R.L., Leonard N.J. J. Am. Chem. Soc. 95:1973;961-962
15. Watanabe K.A., Fox J.J. Angew. Chem., Int. Ed. Engl. 5:1966;579-580
16. Corey E.J., Venkateswarlu A. J. Am. Chem. Soc. 94:1972;6190-6191
17. Baker R., Cummings W.J., Hayes J.F., Kumar A. J. Chem. Soc., Chem. Commun. 1986;1237-1239
18. Khana I.K., Yu Y., Huff R.M., Weier R.M., Xu X., Koszyk F.J., Collins P.W., Cogburn J.N., Isakson P.C., Koboldt C.M., Masferrer J.L., Perkins W.E., Seibert K., Veehuizen A.W., Yuan J., Yang D.-C., Zhang Y.Y. J. Med. Chem. 43:2000;3168-3185
19. De Clercq E., Descamps J., Verhelst G., Walker R.T., Jones A.S., Torrence P.F., Shugar D. J. Infect. Dis. 141:1980;563-574
20. Schols D., De Clercq E., Balzarini J., Baba M., Witvrouw M., Hosoya M., Andrei G., Snoeck R., Neyts J., Pauwells R., Nagry M., Györgyi- Edelényi J., Machovich R., Horvath I., Löw M., Görög S. Antivir. Chem. Chemother. 1:1990;233-240
21. De Clercq E., Holý A., Rosenberg I., Sakuma T., Balzarini J., Maudgal P.C. Nature. 323:1986;464-467
22. De Clercq E., Sakuma T., Baba M., Pauwels R., Balzarini J., Rosenberg I., Holý A. Antivir. Res. 8:1987;261-272