Synthesis and biological activity of some new 5′-O-acyl tiazofurin derivatives

European Journal of Medicinal Chemistry

Volumn 41, Issue 4, 2006, Pages 503-512

  Pejanović, Vjera ^a   Piperski, Vesna ^b   Uglješić Kilibarda, Dragana ^b   Tasić, Jelena ^b   Dačević, Mirjana ^b   Medić Mijačević, Ljubica ^a   Gunić, Esmir ^c   Popsavin, Mirjana ^a   Popsavin, Velimir ^a  

^a UNIVERSITY OF NOVI SAD   (Serbia)

^b Galenika AD   (Yugoslavia)

^c Valeant Pharmaceuticals International   (United States)

Author keywords

Anticancer agents; Apoptosis; Cytotoxicity; Prodrugs; Tiazofurin derivatives

Indexed keywords

2 (5 O ACETYL BETA DEXTRO RIBOFURANOSYL)THIAZOLE 4 CARBOXAMIDE; 2 (5 O BENZOYL BETA DEXTRO RIBOFURANOSYL)THIAZOLE 4 CARBOXAMIDE; 2 [5 O [6 (ALPHA,BETA DEXTRO GLUCOPYRANOS 3 YL)HEXANOYL] BETA DEXTRO RIBOFURANOSYL]THIAZOLE 4 CARBOXAMIDE; THIAZOLE DERIVATIVE; TIAZOFURIN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DNA; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; RIBAVIRIN;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL MEMBRANE PERMEABILITY; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; RAT; TUMOR CELL CULTURE; ANIMAL; BIOSYNTHESIS; CELL DIVISION; CELL SURVIVAL; DRUG EFFECT; GENETICS; INFRARED SPECTROPHOTOMETRY; MOUSE; NICK END LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL DIVISION; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHYSICAL; DNA, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IN SITU NICK-END LABELING; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; RIBAVIRIN; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646469365     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2006.01.005     Document Type: Article

References (37)

1. Grifantini M. Curr. Opin. Invest. Drugs 1 (2000) 257-262
2. Malek K., Boosalis M., Waraska K., Mitchell B.S., and Wright D.G. Leukemia Res. 28 (2004) 1125-1136
3. Wright D.G., Boosalis M., Malek K., and Waraska K. Leukemia Res. 28 (2004) 1137-1143
4. Wright D.G., Boosalis M.S., Waraska K., Oshry L.J., Weintraub L.R., and Vosburgh E. Anticancer Res. 16 (1996) 3349-3351
5. Tricot G., and Weber G. Anticancer Res. 16 (1996) 3341-3347
6. Weber G., Nagai M., Natsumeda Y., Eble J.N., Jayaram H.N., Paulik E., Zhen W.N., Hoffman R., and Tricot G. Cancer Commun. 3 (1991) 61-66
7. Pankiewicz K.W., Patterson S.E., Black P.L., Jayaram H.N., Risal D., Goldstein B.M., Stuyver L.J., and Schinazi R.F. Curr. Med. Chem. 11 (2004) 887-900 (For a recent review see)
8. Vranić-Mandušić V., Subota V., Savovski K., Medić L., Dramićanin T., Jozanov-Stankov O., Popov-Čeleketić D., Jokanović M., and Dimitrijević B. Toxicol. Lett. 146 (2004) 275-284
9. Tricot G., Jayaram H.N., Weber G., and Hoffman R. Int. J. Cell Cloning 8 (1990) 161-170
10. Navarre J.-M. D. Guianvarc'h, A. Farese-Di Giorgio, R. Condom, R. Benhida, Tetrahedron Lett. 44 (2003) 2199-2202
11. Franchetti P., Marchetti S., Cappellacci L., Yalowitz J.A., Jayaram H.N., Goldstein B.M., and Grifantini M. Bioorg. Med. Chem. Lett. 11 (2001) 67-69
12. Franchetti P., Marchetti S., Cappellacci L., Jayaram H.N., Yalowitz J.A., Goldstein B.M., Barascut J.-L., Dukhan D., Imbach J.-L., and Grifantini M. J. Med. Chem. 43 (2000) 1264-1270
13. Franchetti P., Marchetti S., Cappellacci L., Grifantini M., Goldstein B.M., Dukhan D., Barascut J.-L., and Imbach J.-L. Nucleosides Nucleotides 18 (1999) 679-680
14. Franchetti P., Cappellacci L., Abu Seikha G., Jayaram H.N., Gurudutt V.V., Sint T., Schneider B.P., Jones W.D., Goldstein B.M., Perra G., De Montis A., Loi A.G., La Colla P., and Grifantini M. J. Med. Chem. 40 (1997) 1731-1737
15. Franchetti P., Cappellacci L., Grifantini M., Barzi A., Nocentini G., Yang H., O'Conor A., Jayaram H.N., Corell C., and Goldstein B.M. J. Med. Chem. 38 (1995) 3829-3837
16. Nair V., and Wenzel T. ARKIVOC 14 (2004) 128-132
17. Popsavin M. Lj. Torović, V. Kojić, G. Bogdanović, V. Popsavin, Tetrahedron Lett. 45 (2004) 7125-7128
18. Liang C.W., Kim M.J., Jeong L.S., and Chun M.W. Nucleosides Nucleotides Nucleic Acids 22 (2003) 2039-2048
19. Popsavin M. Lj. Torović, V. Kojić, G. Bogdanović, S. Spaić, V. Popsavin. Bioorg. Med. Chem. Lett. 13 (2003) 3167-3170
20. Cappellacci L., Barboni G., Franchetti P., Martini C., Jayaram H.N., and Grifantini M. Nucleosides Nucleotides Nucleic Acids 22 (2003) 869-872
21. Zhang H.Y., Yu H.W., Ma L.T., Min J.M., and Zhang L.H. Tetrahedron Asymmetry 9 (1998) 141-149
22. Rivault F., Tranoy-Opalinski I., and Gesson J.-P. Bioorg. Med. Chem. 12 (2004) 675-682
23. Cai T.B., Tang X., Nagorski J., Brauschweiger P.G., and Wang P.G. Bioorg. Med. Chem. 11 (2003) 4971-4975
24. Nomura M., Shuto S., and Matsuda A. Bioorg. Med. Chem. 11 (2003) 2453-2461
25. Breistol K., Balzarini J., Sandvold M.L., Myhren F., Martinsen M., De Clercq E., and Fodstad O. Cancer Res. 59 (1999) 2944-2949
26. Meier C. Synlett (1998) 233-242
27. Dačević M.P., Tasić J.S., Pejanović V.M., Segal M.B., Uglješić-Kilibarda D.D., Isaković A.I., Begley D.J., Rakić L.M., and Redžić Z.B. J. Drug Targ. 10 (2002) 633-636
28. Hanna N.B., Upadhya K.G., Petrie C.R., Robins R.K., and Revankar G.R. Nucleosides Nucleotides 5 (1986) 343-362
29. Fuertes M., Garcia-Lopez M.T., Garcia-Munoz G., and Stud M. J. Org. Chem. 41 (1976) 4074-4077
30. Miljković D., Pietrzkowsky Z., Gunić E., and Seifert W. US patent 5 723 (1998) 589
31. Willie A.H., Kerr J.F.R., and Currie A.R. Int. Rev. Cytol. 68 (1980) 251-306
32. Gavrieli Y., Sherman Y., and Ben-Sasson S.A. J. Cell Biol. 119 (1992) 493-501
33. Piperski V., Vračar M., Jokanović M., Stukalov P., and Rakić L. Apoptosis 3 (1998) 345-352
34. Tasić J., Ristić S., Piperski V., Dačević M., Pejanović V., Jokanović M., and Mandić L. J. Pharm. Biomed. Anal. 30 (2002) 993-999
35. Franchetti P., Cappellacci L., Marchetti S., Martini C., Costa B., Varani K., Borea P.A., and Grifantini M. Bioorg. Med. Chem 8 (2000) 2367-2373 (and references cited therein)
36. Ramasamy K., Lewis A., Robins R.K., Raju N., Bharadway N., and Pejanović V. US patent 5 907 (1999) 36
37. Gebeyehu G., Marquez V.E., Kelley J.A., Cooney D.A., Jayaram H.N., and Johns D.G. J. Med. Chem. 26 (1983) 922-925