2-(3-Amino-3-deoxy-β-d-xylofuranosyl)thiazole-4-carboxamide: A new tiazofurin analogue with potent antitumour activity

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 20, 2006, Pages 5317-5320

  Popsavin, Mirjana ^a   Spaić, Saša ^a   Svirčev, Miloš ^a   Kojić, Vesna ^b   Bogdanović, Gordana ^b   Popsavin, Velimir ^a  

^a UNIVERSITY OF NOVI SAD   (Serbia)

^b Institute of Oncology Sremska Kamenica   (Yugoslavia)

Author keywords

2,5 Anhydro sugars; Antitumour agents; C Nucleosides; Epoxide ring opening; Thiazoles; Tiazofurin analogues

Indexed keywords

2 (3 AMINO 3 DEOXY BETA DEXTRO XYLOFURANOSYL)THIAZOLE 4 CARBOXAMIDE; GLUCOSE; THIAZOLE DERIVATIVE; TIAZOFURIN; TIAZOFURIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN K 562; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL LINE;

EID: 33748323116     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.07.086     Document Type: Article

References (40)

1. Srivastava P.C., Pickering M.V., Allen L.B., Streeter D.G., Campbell M.T., Witkowski J.T., Sidwell R.W., and Robins R.K. J. Med. Chem. 20 (1977) 256
2. For recent reviews on inhibition of IMPDH and guanine nucleotide synthesis, see:. 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
3. Christopherson R.I., Lyons S.D., and Wilson P.K. Acc. Chem. Res. 35 (2002) 961
4. Pankiewicz K.W. Exp. Opin. Ther. Patents 9 (1999) 55
5. Hedstrom L. Curr. Med. Chem. 6 (1999) 545
6. Jayaram H.N., Grusch M., Cooney D.A., and Krupitza G. Curr. Med. Chem. 6 (1999) 561
7. Franchetti P., and Grifantini M. Curr. Med. Chem. 6 (1999) 599
8. Robins R.K., Srivastava P.C., Narayanan V.L., Plowman L., and Paull K.D. J. Med. Chem. 25 (1982) 107
9. For recent reviews on biochemical and clinical impact of tiazofurin, see:. Weber G., Shen F., Orbán T.I., Kökeny S., and Olah E. Adv. Enzyme Regul. 43 (2003) 47
10. Grifantini M. Curr. Opin. Invest. Drugs 1 (2000) 257
11. The results of in vitro cytotoxicity testing of tiazofurin against a panel of 60 human tumour cells are available at: http://dtp.nci.nih.gov/dtpstandard/servlet/MeanGraphSummary?searchtype=NSC&outputformat=html&searchlist=286193.
12. Malek K., Boosalis M., Waraska K., Mitchell B.S., and Wright D.G. Leukemia Res. 28 (2004) 1125
13. Jayaram H.N., Lapis E., Tricot G.J., Kneebone P., Paulik E., Zhen W., Engeler G.P., Hoffman R., and Weber G. Int. J. Cancer 51 (1992) 182
14. Tricot G.J., Jayaram H.N., Lapis E., Natsumeda Y., Nichols C.R., Kneebone P., Heerema N., Weber G., and Hoffman R. Cancer Res. 49 (1989) 3696
15. Wright D.G., Boosalis M.S., Waraska K., Oshry L.J., Weintraub L.R., and Vosburgh E. Anticancer Res. 16 (1996) 3349
16. Tricot G., and Weber G. Anticancer Res. 16 (1996) 3341
17. For recent syntheses of tiazofurin analogues with modified sugar moieties, see:. Merino P., Tejero T., Unzurrunzaga F.J., Franco S., Chiacchio U., Saita M.G., Iannazzo D., Pipernoc A., and Romeo G. Tetrahedron: Asymmetry 16 (2005) 3865
18. Chiacchio U., Rescifina A., Saita M.G., Iannazzo D., Romeo G., Mates J.A., Tejero T., and Merino P. J. Org. Chem. 70 (2005) 8991
19. Chun M.W., Kim M.J., Shin J.H., and Jeong L.S. Nucleosides Nucleotides Nucleic Acids 24 (2005) 975
20. Nair V., and Wenzel T. ARKIVOC 14 (2004) 128
21. Liang C.W., Kim M.J., Jeong L.S., and Chun M.W. Nucleosides Nucleotides Nucleic Acids 22 (2003) 2039
22. Cappellacci L., Barboni G., Franchetti P., Martini C., Jayaram H.N., and Grifantini M. Nucleosides Nucleotides Nucleic Acids 22 (2003) 869
23. Franchetti P.S., Marchetti S., Cappellacci L., Jayaram H.M., Yalowitz J.A., Goldstein B.M., Barascut J.-L., Dukhan D., Imbach J.-L., and Grifantini M. J. Med. Chem. 43 (2000) 1264
24. Qu F., Hong J.H., Du J., Newton M.G., and Chu C.K. Tetrahedron 55 (1999) 9073
25. Zhang H.Y., Yu H.W., Ma L.T., Min J.M., and Zhang L.H. Tetrahedron: Asymmetry 9 (1998) 141
26. For example, the C-3 epimer of 3 has been evaluated in vitro for its ability to inhibit the growth of human 143B Osteosarcoma cells, but found to be completely inactive (see Ref. 8e).
27. Popsavin M., Torović Lj., Spaić S., Stankov S., and Popsavin V. Tetrahedron Lett. 41 (2000) 5737
28. Popsavin M., Torović Lj., Spaić S., Stankov S., Kapor A., Tomić Z., and Popsavin V. Tetrahedron 58 (2002) 569
29. Popsavin M., Torović Lj., Kojić V., Bogdanović G., Spaić S., and Popsavin V. Bioorg. Med. Chem. Lett. 13 (2003) 3167
30. Popsavin M., Torović Lj., Kojić V., Bogdanović G., and Popsavin V. Tetrahedron Lett. 45 (2004) 7125
31. Popsavin M., Torović Lj., Svirčev M., Kojić V., Bogdanović G., and Popsavin V. Bioorg. Med. Chem. Lett. 16 (2006) 2773
32. Suhadolnik R.J. Nucleoside Antibiotics (1970), Wiley-Interscience, New York
33. Suhadolnik R.J. Nucleosides as Biological Probes (1979), Wiley-Interscience, New York
34. Balzarini J. Pharm. World Sci. 16 (1994) 113
35. Popsavin M., Popsavin V., Vukojević N., Csanádi J., and Miljković D. Carbohydr. Res. 260 (1994) 145
36. Banaszek A., and Janisz B. Tetrahedron: Asymmetry 11 (2000) 4693
37. Secrist III J.A., and Logue M.W. J. Org. Chem. 37 (1972) 335
38. Aguilar E., and Meyers A.I. Tetrahedron Lett. 35 (1994) 2773
39. 2 ).
40. 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