Imidazole substituted biphenyls: A new class of highly potent and in vivo active inhibitors of P450 17 as potential therapeutics for treatment of prostate cancer

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 9, 1999, Pages 1913-1924

  Wachall, Bertil G ^a   Hector, Markus ^a   Zhuang, Yan ^a   Hartmann, Rolf W ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

17 hydroxylase C17,20 lyase (P450 17); Antineoplastics; Enzyme inhibitors; Imidazole substituted biphenyls; QSAR; Theoretical calculations

Indexed keywords

ANTINEOPLASTIC AGENT; BIPHENYL DERIVATIVE; CYTOCHROME P450 INHIBITOR; IMIDAZOLE DERIVATIVE; KETOCONAZOLE; PREGNENOLONE;

ANIMAL CELL; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG POTENCY; HUMAN; HUMAN CELL; INHIBITION KINETICS; INTRAPERITONEAL DRUG ADMINISTRATION; NONHUMAN; PROSTATE CANCER; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SPECIES DIFFERENCE; TESTOSTERONE BLOOD LEVEL;

ANIMALS; BIPHENYL COMPOUNDS; ENZYME INHIBITORS; HUMANS; IMIDAZOLES; MALE; PROSTATIC NEOPLASMS; RATS; RATS, SPRAGUE-DAWLEY; SPECTRUM ANALYSIS; STEROID 17-ALPHA-HYDROXYLASE; STRUCTURE-ACTIVITY RELATIONSHIP; TESTOSTERONE;

EID: 0032835607     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00160-1     Document Type: Article

References (40)

1. Sergejew T., Hartmann R.W. J. Enzyme Inhib. 8:1994;113.
2. Barrie S.E., Jarman M. Endocr. Relat. Cancer. 3:1996;25.
3. Jarman, M.; Smith, H. J.; Nicholls, P. J.; Simons, C. Nat. Prod. Rep. 1998, 495.
4. Wächter G.A., Hartmann R.W., Sergejew T., Grün G.L., Ledergerber D. J. Med. Chem. 39:1996;834.
5. Chan F., Potter G.A., Barrie S.E., Haynes P.B., Rowlands M.G., Houghton J., Jarman M. J. Med. Chem. 39:1996;3319.
6. Potter G.A., Barrie S.E., Jarman M., Rowlands M.G. J. Med. Chem. 38:1995;2463.
7. Li J.-S., Son C., Brodie A.M.H. J. Med. Chem. 39:1996;4335.
8. Njar V.C.O., Hector M., Hartmann R.W. J. Bioorg. Med. Chem. 4:1996;1447.
9. Ling Y.-Z., Liu Y., Kato K., Klus G.T., Brodie A. J. Med. Chem. 40:1997;3297.
10. Njar V.C.O., Kato K., Nnane I.P., Grigoryev D.N., Long B.J., Brodie M.H.A. J. Med. Chem. 41:1998;902.
11. McCague R., Rowlands M.G., Barrie S.E., Houghton J. J. Med. Chem. 33:1990;3050.
12. Ahmed S., Smith J.H., Nicholls P.J., Whomsley R., Cariuk P. Drug Des. Discov. 13:1995;27.
13. Rowlands M.G., Barrie S.E., Chan F., Jarman M., McCague R., Potter G.A. J. Med. Chem. 38:1995;4191.
14. Hartmann R.W., Frotscher M., Ledergerber D., Wächter G.A., Grün G.L., Sergejew T.F. Arch. Pharm. Pharm. Med. Chem. 329:1996;251.
15. Hartmann R.W., Bayer H., Grün G., Sergejew T., Bartz U., Mitrenga M. J. Med. Chem. 38:1995;2103.
16. Hartmann R.W., Wächter G.A., Sergejew T., Würtz R., Düerkop J. Arch. Pharm. Pharm. Med. Chem. 328:1995;573.
17. Al-Hamrouni A.M., Ahmadi M., Nicholls P.J., Smith H.J., Lombardi P., Pestellini V. Pharm. Sci. 3:1997;259.
18. Laughton C.A., Neidle S. J. Med. Chem. 33:1990;3055.
19. Ayub M, Levell M.J. J. Steroid Biochem. 28:1987;521.
20. Ahmed S. Drug Des. Discov. 12:1994;77.
21. Patent; Welcome Found; DE 2903653; Chem. Abstr. 1979, 92, 58775.
22. Baggaley K.H., Heald M., Hindley R.M., Morgan B., Tee J.L., Green J. J. Med. Chem. 18:1975;833.
23. Miyaura N., Yanagi T., Suzuki A. Synth. Comm. 11:1981;513.
24. Kumada M. Pure Appl. Chem. 52:1980;669.
25. Negishi E., King A.O., Okukado N. J. Org. Chem. 42:1977;1821.
26. Späth E., Quietensky H. Chem. Ber. 60:1927;1882.
27. Bumagin N.A., Luzikova E.V. J. Organomet. Chem. 532:1997;271.
28. Cuberes M.R., Moreno-Manas M., Trius A. Synthesis. 3:1985;302.
29. Li J., Li Y., Brodie A.M.H. J. Med. Chem. 39:1996;4335.
30. Swart P., Swart A.C., Waterman R., Estabrook R.W., Mason J.I. J. Clin. Endocrinol. Metab. 77:1993;98.
31. De Coster R., Wouters W., Bruynseels J. J. Steroid Biochem. Molec. Biol. 56:1996;133.
32. Rekker, R. F.; Mannhold, R. In Calculation Of Drug Lipophilicity. The Hydrophobic Fragmental Approach; Verlag Chemie: Weinheim, 1992.
33. Seydel. J. K.; Schaper, K.-J. In Chemische Struktur und biologische Aktivität von Wirkstoffen; Verlag Chemie: Weinheim, 1979; pp. 266-295.
34. Kubinyi, H. In QSAR: Hansch Analysis And Related Approach; Mannhold, R.; Krogsgaard-Larsen, P.; Timmerman, H., Eds.; Verlag Chemie: Weinheim, 1993; pp 54-55.
35. Laughton C.A., Neidle S., Zvelebil M.J.J.M., Sternberg M.J.E. Biochem. Biophys. Res. Commun. 171:1990;1160.
36. Lin D., Zhang L-H., Chiao E., Miller W.L. Mol. Endocrinol. 8:1994;392.
37. Burke D.F., Laughton C.A., Neidle S. Anticancer Drug Des. 12:1997;113.
38. Gray, G. W.; Mosley, A. J. Chem. Soc., Perkin Trans. 2 1976, 97.
39. Patent; Sandoz AG; DE 2262340; Chem. Abstr. 1973, 79, 147435.
40. Hartmann R.W., Batzl C. J. Med. Chem. 29:1986;1363.