Phenolic Metabolites of Clomiphene: [(E,Z)-2-[4-(l,2-Diphenyl-2-chlorovinyl)phenoxy]ethyl]diethylamine. Preparation, Electrophilicity, and Effects in MCF 7 Breast Cancer Cells

Journal of Medicinal Chemistry

Volumn 32, Issue 1, 1989, Pages 192-197

  Ruenitz, Peter C ^a   Arrendale, Richard F ^b   Schmidt, Walter F ^a   Thompson, Carolyn B ^a   Nanavati, Nitin T ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4' HYDROXY 3' METHOXYCLOMIFENE; 4' HYDROXYCLOMIFENE; CLOMIFENE DERIVATIVE; DRUG METABOLITE; ESTRADIOL; ESTROGEN RECEPTOR; RADIOISOTOPE; TAMOXIFEN; UNCLASSIFIED DRUG;

BREAST CANCER; CELL CULTURE; CELL GROWTH; CELL STRAIN MCF 7; CYTOTOXICITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

BINDING, COMPETITIVE; BREAST NEOPLASMS; CELL SURVIVAL; CHEMISTRY; CLOMIPHENE; ESTROGEN ANTAGONISTS; FEMALE; HUMAN; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, U.S. GOV'T, P.H.S.; TUMOR CELLS, CULTURED;

EID: 0024493863     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00121a035     Document Type: Article

References (20)

1. Lippman, M. E. In Williams Textbook of Endocrinology, 7th ed.; Wilson, J. D., Foster, D. W., Eds.; W. B. Saunders: Philadelphia, 1985; pp 1309–1319.
2. For convenience, the trans configurations of 1 and other tri-arylethylenes are illustrated.
3. Murphy, L. C.; Sutherland, R. L. J. Clin. Endocrinol. Me-tab. 1983, 57, 373–379. Hubinont, P. O., Leroy, F., Galand, P., Eds. Basic Action of Sex Steroids on Target Organs; S. Karger AG: Basel, 1971; pp 274–279.
4. Huppert, L. C. Fertil. Steril. 1979, 31, 1–8. Adashi, E. Y. Fertil. Steril. 1984, 42, 331–344.
5. Ruenitz, P. C.; Bagley, J. R.; Mokler, C. M. Biochem. Pharmacol. 1983, 32, 2941–2947. Ruenitz, P. C.; Bagley, J. R.; Watts, C. K. W.; Hall, R. E.; Sutherland, R. L. J. Med. Chem. 1986, 29, 2511–2519.
6. Ruenitz, P. C.; Arrendale, R. F.; George, G. D.; Thompson, C. B.; Mokler, C. M.; Nanavati, N. T. Cancer Res. 1987, 47, 4015–4019.
7. Ruenitz, P. C.; Bagley, J. R.; Nanavati, N. T. J. Med. Chem. 1988, 31, 1471–1475.
8. Coe, P. L.; Scriven, C. E. J. Chem. Soc., Perkin Trans. 1 1986, 475–477. Shani, J.; Gazit, A.; Livshitz, T.; Biran, S. J. Med. Chem. 1985, 28, 1504–1511. McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem. 1978, 43, 3255–3266.
9. Epstein, J.; Rosenthal, R. W.; Ess, R. J. Anal. Chem. 1955, 27, 1435–1439. Friedman, 0. M.; Boger, E. Anal. Chem. 1961. 33. 906–910.
10. Ruenitz, P. C.; Bagley, J. R.; Mokler, C. M. J. Med. Chem. 1982, 25, 1056–1060. Ruenitz, P. C.; Bagley, J. R. Biochem. Pharmacol. 1985. 34, 2807–2809.
11. Sutherland, R. L.; Hall, R. E.; Taylor, I. W. Cancer Res. 1983, 43, 3998–4006. Reddel, R. R.; Murphy, L. C.; Hall, R. E.; Sutherland, R. L. Cancer Res. 1985, 45, 1525–1531.
12. Chamberlain, N. F. The Practice of NMR Spectroscopy; Plenum: New York, 1974; p 267. Mukaiyama, T.; Aizawa, S.; Yamaguchi, T. Bull. Chem. Soc. Jpn. 1967, 40, 2641–2644. Akiyama, F. Bull. Chem. Soc. Jpn. 1977, 50, 936–938.
13. Katzenellenbogen, J. A.; Carlson, K. E.; Heiman, D. F.; Robertson, D. W.; Wei, L. L.; Katzenellenbogen, B. S. J. Biol. Chem. 1983, 258, 3487–3495.
14. LeClercq, G.; Devleeschouwer, N.; Heuson, J. C. J. Steroid Biochem. 1983, 19, 75–85.
15. Wei, L. L.; Mangel, W. F.; Katzenellenbogen, B. S. J. Steroid Biochem. 1985, 23, 875–881.
16. Sutherland, R. L.; Murphy, L. C. Mol. Cell. Endocrinol. 1982, 25, 5–23. Wakeling, A. E.; Valcaccia, B.; Newboult, E.; Green, L. R. J. Steroid Biochem. 1984, 20, 111–120. Rochefort, H.; Borgna, J. L.; Evans, E. J. Steroid Biochem. 1983,19, 69–74. Sutherland, R. L.; Watts, C. K. W.; Hall, R. E.; Ruenitz, P. C. J. Steroid Biochem. 1987, 27, 891–897.
17. Martin, S. A.; Costello, C. E.; Biemann, K. Anal. Chem. 1982, 54, 2362–2368.
18. Allen, R. E.; Palopoli, F. P.; Schumann, E. L.; Van Campen, M. G., Jr. U. S. Patent Chem. Abstr. 1960, 54, 5581e-5584e.
19. Ruenitz, P. C. Drug. Metab. Dispos. 1981, 9, 456–460.
20. Flavin, M. J. Biol. Chem. 1962, 237, 768–777.