The development of the antitumour benzothiazole prodrug, phortress, as a clinical candidate

Current Medicinal Chemistry

Volumn 11, Issue 8, 2004, Pages 1009-1021

  Bradshaw, T D ^a   Westwell, Andrew D ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Antitumour benzothiazoles; Arylhydrocarbon receptor; Cytochrome P450 1A1; Drug development; Fluorination; Nitrenium ion; Prodrug

Indexed keywords

2 (4 AMINO 3 CYANOPHENYL) 5 FLUOROBENZATHIAZOLE; 2 (4 AMINO 3 METHYLPHENYL)BENZOTHIAZOLE; 5 FLUORO 2 (4 LYSYLAMINO 3 METHYLPHENYL)BENZOTHIAZOLE; 5F 203; ANTINEOPLASTIC AGENT; AROMATIC HYDROCARBON RECEPTOR; BENZOTHIAZOLE DERIVATIVE; CYTOCHROME P450 1A1; DOXORUBICIN; DRUG METABOLITE; PRODRUG; RESVERATROL; UNCLASSIFIED DRUG;

CELL DEATH; CELL NUCLEUS; DNA ADDUCT; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG SYNTHESIS; DRUG TRANSPORT; DRUG UPTAKE; ENZYME INDUCTION; HUMAN; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; REVIEW;

ANILINE COMPOUNDS; ANIMALS; ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; CYTOCHROME P-450 CYP1A1; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; PRODRUGS; THIAZOLES; TIME FACTORS;

EID: 1842484230     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867043455530     Document Type: Review

References (35)

1. Shi, D-F.; Bradshaw, T.D.; Wrigley, S.; McCall, C.J.; Lelieveld, P.; Fichtner, I.; Stevens, M.F.G. J. Med. Chem., 1996, 39, 3375-3384.
2. Bradshaw, T.D.; Stevens, M.F.G.; Westwell, A.D. Curr. Med. Chem., 2001, 8, 203-210.
3. Bradshaw, T.D.; Trapani, V.; Vasselin, D.A.; Westwell, A.D. Curr. Pharm. Des., 2002, 8, 2475-2490.
4. Patterson, L.H.; Murray, G.E. Curr. Pharm. Des., 2002, 8, 1335-1347.
5. Kashiyama, E., Hutchinson, I., Chua, M-S., Stinson, S.F., Phillips, L.R., Kaur, G., Sausville, E.A., Bradshaw, T.D., Westwell, A.D., Stevens, M.F.G. J. Med Chem., 1999, 42, 4172-4184.
6. Chua, M-S.; Kashiyama, E.; Bradshaw, T.D.; Stinson, S.F.; Brantley, E.; Sausville, E.A.; Stevens, M.F.G. Cancer Res., 2000, 60, 5196-5203.
7. Whitlock, J.P. Jr. Annu. Rev. Pharmacol. Toxicol., 1999, 39, 103-125.
8. Ma, Q.; Whitlock, J.P. Jr. J. Biol. Chem., 1997, 272, 8878-8884.
9. Hose, C.; Riviera, M.; Sausville, E.A.; Monks, A. Proc. Am. Assoc. Cancer Res., 2001, 42, 511.
10. Loaiza-Pérez, A.I.; Trapani, V.; Hose, C.; Singh, S.S.; Trepel, J.B.; Stevens, M.F.G.; Bradshaw, T.D.; Sausville, E.A. Mol. Pharmacol., 2002, 61, 13-19.
11. Stevens, M.F.G.; Heydon, R.T.; Martin, E.A.; Farmer, P.B.; Bradshaw, T.D.; Hutchinson, I.; Westwell, A.D.; Browne, H.L.; Trapani, V. Proc. Am. Assoc. Cancer Res., 2001, 42, 1754.
12. Hutchinson, I.; Chua, M-S.; Browne, H.L.; Trapani, V.; Bradshaw, T.D.; Westwell, A.D.; Stevens, M.F.G. J. Med. Chem., 2001, 44, 1446-1455.
13. Liehr, J.G. Mol. Pharmacol., 1983, 23, 278-28l.
14. Morgan, P.; Maggs, J.L.; Bulman-Page, P.C.; Hussian, F.; Park, B.K. Biochem. Pharmacol., 1992, 43, 985-994.
15. Bradshaw, T.D.; Bibby, M.C.; Double, J.A.; Fichtner, I.; Cooper, P.A.; Alley, M.C.; Donohue, S.; Stinson, S.F.; Tomaszewjski, J.E.; Sausville, E.A.; Stevens, M.F.G. Mol. Cancer Therap., 2002, 1, 239-246.
16. Trapani, V. PhD Thesis, University of Nottingham, 2002.
17. Hose, C.; Hollingshead, M.; Sausville, E.A.; Monks, A. Mol. Cancer Therap., in press.
18. Leong, C-O.; Gaskell, M.; Martin, E.A.; Heydon, R.T.; Farmer, P.B.; Bibby, M.C.; Cooper, P.A.; Double, J.A.; Bradshaw, T.D.; Stevens, M.F.G. Brit. J. Cancer, 2003, 88, 470-477.
19. O'Brien, S.E.; Browne, H.L.; Bradshaw, T.D.; Westwell, A.D.; Stevens, M.F.G. Org. Biomol. Chem., 2003, 1, 493-497.
20. Shi, D-F.; Bradshaw, T.D.; Chua, M-S.; Westwell, A.D.; Stevens, M.F.G. Bioorg. & Med. Chem. Lett., 2001, 11, 1093-1095.
21. Hutchinson, I.; Jennings, S.A.; Vishnuvajjala, B.R.; Westwell, A.D.; Stevens, M.F.G. J. Med Chem., 2002, 45, 744-747.
22. Pochopin, N.L.; Charman, W.N.; Stella, V.J. Int. J. Pharm., 1995, 121, 157-167.
23. Bradshaw, T.D.; Chua, M-S.; Browne, H.L.; Trapani, V.; Sausville, E.A.; Stevens, M.F.G. Brit. J. Cancer, 2002, 86, 1348-1354.
24. Hutchinson, I.; Bradshaw, T.D.; Matthews, C.S.; Stevens, M.F.G.; Westwell, A.D. Bioorg. & Med. Chem. Lett., 2003, 13, 471-474.
25. Kuffel, M.J.; Schroeder, J.C.; Pobst, L.J.; Naylor, S.; Reid, J.M.; Kaufmann, S.H.; Ames, M.M. Mol. Pharmacol., 2002, 62, 143-153.
26. Hutchinson, I., Stevens, M.F.G., Westwell, A.D. Tetrahedron Lett., 2000, 41, 425-428.
27. Roe, A., Tucker, W.P. J. Heterocycl. Chem., 1965, 2, 148-151.
28. McKittrick, B., Failli, A., Steffan, R.J., Soll, R.M., Hughes, P., Schmid, J., Asselin, A.A., Shaw, C.C., Noureldin, R., Gavin, G. J. Heterocycl. Chem., 1990, 27, 2151-2163.
29. Ishikawa, H., Uno, T., Miyamoto, H., Ueda, H., Tamaoka, H., Tominaga, M., Nakagawa, K. Chem. Pharm. Bull., 1990, 38, 9459-9462.
30. Spitulnik, M.J. Synthesis, 1976, 730-731.
31. Chang, Y.-H., Peak, J.D., Wierschke, S.W., Feld, W.A. Synth. Comm., 1993, 23, 663-670.
32. Schnur, R.C., Fliri, A.F.J., Kajiji, S., Pollack, V.A. J. Med. Chem., 1991, 34, 914-918.
33. Brown, G.D.; Wilson, H.; Westwell, A.D.; Hutchinson, I.; Stevens, M.F.G.; Price, P.M.; Aboagye, E.; Luthra, S.K.; Brady, F. J. Label. Compd. Radiopharm., 2001, 44 (Suppl. 1), S374-S375.
34. Sureau, R.F.M., Obellianne, P.M.J. US Patent 2,789,132; Chem. Abstr. 1957, 51, 15571.
35. Stevens, M.F.G.; Poote, T.D.; Westwell, A.D.; Hutchinson, I.P.; Chua, M-S. International Patent Number, WO 01 / 14354 A1 (Publication Date: March 1, 2001).