Derivatives of Tamoxifen. Dependence of Antiestrogenicity on the 4-Substituent

Journal of Medicinal Chemistry

Volumn 32, Issue 12, 1989, Pages 2527-2533

  Mccague, Raymond ^a   Leclercq, Guy ^b   Legros, Nicole ^b   Goodman, Joyce ^c   Blackburn, G Michael ^c   Foster, Allan B ^a   Jarman, Michael ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^b JULES BORDET INSTITUTE   (Belgium)

^c UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ESTRADIOL; ESTROGEN RECEPTOR; RADIOISOTOPE; TAMOXIFEN; TAMOXIFEN DERIVATIVE;

ANIMAL CELL; ARTICLE; BREAST CANCER; CATTLE; CELL CULTURE; CELL STRAIN MCF 7; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; UTERUS;

ANIMAL; CATTLE; CHEMISTRY; CYTOSOL; ESTROGEN ANTAGONISTS; FEMALE; RECEPTORS, ESTROGEN; SUPPORT, NON-U.S. GOV'T; TAMOXIFEN; TUMOR CELLS, CULTURED; UTERUS;

EID: 0024395769     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00132a006     Document Type: Article

References (38)

1. Heel, R. C.; Brogden, R. N.; Speight, T. M.; Avery, G. S. Drugs 1978, 16, 1.
2. Furr, B. J. A.; Jordan, V. C. Pharmacol. Ther. 1984, 25, 127.
3. Nicholson, R. I.; Daniel, P.; Gaskell, S. J.; Syne, J. S.; Davies, P.; Griffiths, K. Antihormones 1979, 253.
4. Jordan, V. C. Breast Cancer Res. Treat. 1982, 2, 123.
5. Daniel, C. P.; Gaskell, S. J.; Bishop, H.; Nicholson, R. I. J. Endocrinol. 1979, 83, 401.
6. Jordan, V. C.; Collins, M.; Rowsby, L.; Prestwich, G. J. Endocrinol. 1977, 75, 305.
7. Binart, N.; Catelli, M. G.; Geynet, C.; Puri, V.; Hahnel, R.; Mester, J.; Baulieu, E. E. Biochem. Biophys. Res. Commun. 1979. 91, 812.
8. Wakeling, A. E.; Slater, S. R. Cancer Treat. Rep. 1980, 64, 741
9. Jordan, V. C.; Naylor, K. E. Proc. Br. Pharmacol. Soc. 1978, 376 p.
10. Jordan. V. C.: Allen. K. E. Eur. J. Cancer 1980. 16. 239.
11. Jordan, V. C.; Allen, K. E. Antihormones 1979, 235.
12. Allen, K. E.; Clark, E. R.; Jordan, V. C. Br. J. Pharmacol. 1980, 68, 171 p.
13. Shani, J.; Gazit, A.; Livshitz, T.; Biran, S. J. Med. Chem. 1985, 28, 1504.
14. McCague, R. J. Chem. Soc. Perkin Trans. 1 1987, 1011.
15. Jarman, M.; McCague, R. J. Chem. Res., Synop. 1985, 116; J. Chem. Res., Miniprint 1985, 1342.
16. McCague, R. J. Chem. Res., Synop. 1986, 58; J. Chem. Res., Miniprint 1986, 771.
17. Olah, G. H.; Arvanaghi, M. Angew. Chem., Int. Ed. 1981, 20, 878.
18. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353
19. Collins, D. J.; Hobbs, J. J.; Emmens, C. W. J. Med. Chem. 1971, 14, 952.
20. Blackburn, G. M.; Goodman, J.; Smith, A. J. Acta Crystallogr. 1988, C 44, 1629.
21. Leclercq, G.; Devleeschouwer, N.; Heuson, J. C. J. Steroid Biochem. 1983, 19, 75.
22. Foster, A. B.; Jarman, M.; Leung, O. T.; McCague, R.; Le-Clercq, G.; Devleeschouwer, N. J. Med. Chem. 1985, 28, 1491.
23. Murray-Rust, P.; Motherwell, W. D. S. J. Am. Chem. Soc. 1979, 101, 4374.
24. Blaney, J. M.; Jorgensen, E. C.; Connolly, M. L.; Ferrin, T. E.; Langridge, R.; Oatley, S. J.; Burridge, J. M.; Blake, C. C. F. J. Med. Chem. 1982, 25, 785.
25. Bloomer, W. D.; McLaughlin, W. H.; Weichselbaum, R. R.; Tonnesen, G. L.; Hellman, S.; Seitz, D. E.; Hanson, R. N.; Adelstein, S. J.; Rosner, A. L.; Burnstein, N. A.; Nove, J. J.; Little, J. B. Int. J. Radiol. Biol. 1980, 38, 197.
26. Hunter, D. H.; Payne, N. C.; Rahman, A.; Richardson, J. F.; Ponce, Y. Z. Can. J. Chem. 1983, 61, 421.
27. Stoessel, S.; Leclercq, G. J. Steroid Biochem. 1986, 25.,677.
28. Gyling, M.; Leclercq, G. J. Steroid Biochem. 1988, 29, 1.
29. Gill, J. C.; Lockey, P. M.; Marples, B. A.; Traynor, J. R. J. Med. Chem. 1986, 29, 1537.
30. Martin, P. M.; Berthois, Y.; Jensen, E. V. Proc. Natl. Acad. Sci. U. S. A. 1988, 85, 2533.
31. Vignon, F.; Bouton, M. M.; Rochefort, H. Biochem. Biophys. Res. Commun. 1987. 146. 1502.
32. Su, H. D.; Mazzei, G. J.; Vogler, W. R.; Kuo, J. F. Biochem. Pharmacol. 1985, 34, 3649.
33. O'Brian, C. A.; Liskamp, R. M.; Solomon, D. H.; Weinstein, I. B. Cancer Res. 1985, 45, 2462.
34. Lam, H. Y. P. Biochem. Biophys. Res. Commun. 1984, 118, 27.
35. Sutherland, R. L.; Watts, C. K. W.; Hall, R. E.; Ruenitz, P. C. J. Steroid Biochem. 1987, 27, 891.
36. Brandes, L. J.; Bogdanovic, R. P.; Cawker, M. D.; Bose, R. Cancer Chemother. Pharmacol. 1986, 18, 21.
37. Leclercq, G.; Deboel, M.C.; Heuson, J. C. Int. J. Cancer 1976, 18. 750.
38. Olea-Serrano, N.; Devleeschouwer, N.; Leclercq, G.; Heuson, J. C. Eur. J. Cancer Clin. Oncol. 1985, 21, 1965.