Glycosyl and polyalcoholic prodrugs of lonidamine

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 7, 2008, Pages 2445-2450

  Giorgioni, G ^a   Ruggieri, S ^a   Di Stefano, A ^b   Sozio, P ^b   Cinque, B ^c   Di Marzio, L ^b   Santoni, G ^a   Claudi, F ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

^c UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

Anticancer; Lonidamine; Polyalcoholic; Polyhydric; Prodrug; Synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; LONIDAMINE; LONIDAMINE PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG POTENCY; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; HYDROLYSIS; NONHUMAN; PHYSICAL CHEMISTRY;

ABSORPTION; ADMINISTRATION, ORAL; ALCOHOLS; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; GLYCOSIDES; HUMANS; HYDROLYSIS; INDAZOLES; MODELS, CHEMICAL; PRODRUGS; RATS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 41149129726     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.02.046     Document Type: Article

References (24)

1. Corsi G., Palazzo G., Germani C., Scorza Barcellona P., and Silvestrini B. J. Med. Chem. 19 (1976) 778
2. Floridi A., Paggi M.G., D'Atri S., De Martino C., Marcante M.L., Silvestrini B., and Caputo A. Cancer Res. 41 (1981) 4661
3. Fanciulli M., Valentini A., Bruno T., Citro G., Zupi G., and Floridi A. Oncology Res. 8 (1996) 111
4. Raaphorst G.P., Feeley M.M., Heller D.P., Danjoux C.E., Martin L., Maroun J.A., and De Santis S.J. Anticancer Res. 10 (1990) 923
5. Zupi G., Greco C., Laudonio N., Benassi m., Solvestrini B., and Caputo A. Anticancer Res. 6 (1986) 1245
6. Rosbe K.W., Brann T.W., Holden S.A., Teicher B.A., and Frei E. Cancer Chemother. Pharmacol. 25 (1989) 32
7. Di Cosimo S., Ferretti G., Papaldo P., Carlini P., Fabi A., and Cognetti F. Drugs Today 39 (2003) 157
8. Price G.S., Page R.L., Riviere J.E., Cline J.M., and Thrall D.E. Cancer Chemother. Pharmacol. 38 (1996) 129
9. Palmieri G.F., Wehrle P., and Martelli S. Drug Dev. Ind. Pharm. 24 (1998) 653
10. Palmieri G.F., Cantalamessa F., Di Martino P., Nasuti C., and Martelli S. Drug Dev. Ind. Pharm. 28 (2002) 1241
11. Thomas M., Rivault F., Tranoy-Opalinski I., Roche J., Gesson J.-P., and Papot S. Bioorg. Med. Chem. Lett. 17 (2007) 983
12. Steffansen B., Nielsen C.U., Brodin B., Eriksson A.H., Andersen R., and Frokjaer S. Eur. J. Pharm. Sci. 21 (2004) 3
13. Gatenby R.A., and Gillies R.J. Int. J. Biochem. Cell Biol. 39 (2007) 1358
14. Brown R.S., and Wahl R.I. Cancer 72 (1993) 2979
15. 6): 8.14 (d, 2H), 7.85 (d, 2H), 7.66 (d, 2H), 7.52 (t, 2H), 7.35 (m, 4H), 6.96 (d, 2H), 5.84 (s, 4H), 4.52 (m, 6H), 1.38 (s, 6H).
16. 6): 8.18 (d, 1H), 7.86 (d, 1H), 7.71 (d, 1H), 7.53 (t, 1H), 7.37 (m, 2H), 6.98 (d, 1H), 5.88 (s, 2H), 5.53 (d, 1H), 4.68 (dd, 1H), 4.40 ( m, 4H), 4.20 ( m, 1H), 1.32, 1.42 and 1.50 (three s, 12H).
17. 6) δ 8.15 (d, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.45 (m, 3H), 6.95 (d, 1H), 5.86 (s, 2H).
18. 2O): 8.14 (d, 1H), 7.82 (d, 1H), 7.68 (d, 1H), 7.54 (t, 1H), 7.39 (m, 2H), 6.98 (m, 1H), 5.85 (s, 2H), 4.97 and 4.30 (two d, 1H, J′ = 3.4, J″ = 7.4), 4.42 (m, 2H), 4.12 and 3.83 (two m, 1H), 3.77 e 3.70 (two d, 1H, J′ = 3.4; J″ = 7.4).
19. For experimental details see. Quaglia W., Santoni G., Pigini M., Piergentili A., Gentili F., Buccioni M., Mosca M., Lucciarini R., Amantini C., Nabissi M.I., Ballarini P., Poggesi E., Leonardi A., and Giannella M. J. Med. Chem. 48 (2005) 7750
20. Grever, M. R.; Shepartz, S. A.; Chabner, B. A. The National Cancer Institute: Cancer Drug Discovery and Development Program. Semin. Oncol. 1992, 19, 622.
21. Brisdelli F., Coccia C., Cinque B., Cifone M.G., and Bozzi A. Mol Cell. Biochem. 296 (2007) 137
22. For experimental details see. Farghaly A.O. Eur. J. Med. Chem. 33 (1998) 123
23. Yalkowsky S.H., and Morozowich W. In: Ariens E.J. (Ed). A Physical Chemical Basis for the Design of Orally Active Prodrugs. Drug Design Vol. 9 (1980), Academic Press, New York 121
24. For experimental details see. Mahfouz N.M., Tarek A., and Ahmed K.D. Eur. J. Med. Chem. 33 (1988) 675