Chemical synthesis of two novel diaryl ether dimers of estradiol-17β

Steroids

Volumn 69, Issue 1, 2004, Pages 61-65

  Lee, Anthony J ^a   Sowell, J Walter ^a   Cotham, William E ^a   Zhu, Bao Ting ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

Estradiol; Estrogen dimers; Nonpolar estrogen metabolites

Indexed keywords

2 BROMOESTRADIOL 3 O BENZYL ETHER; 4 BROMOESTRADIOL 3 O BENZYL ETHER; BENZYL DERIVATIVE; CARBON; CYTOCHROME P450; ESTRADIOL; ESTRADIOL DERIVATIVE; ETHER DERIVATIVE; HYDROXYL GROUP; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; CONTROLLED STUDY; DIMERIZATION; ESTROGEN SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROGENATION; LIVER MICROSOME; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 0346098089     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2003.10.003     Document Type: Article

References (17)

1. Cavalieri E.L., Stack D.E., Devanesan P.D., Todorovic R., Dwivedy I., Higginbotham S.et al. Molecular origin of cancer: catechol estrogen-3, 4-quinones as endogeneous tumor initators. Proc. Natl. Acad. Sci.: USA. 94:1997;10937-10942.
2. Cavalieri E, Frenkel K, Liehr JG, Rogan E, Roy D. Estrogens as endogenous genotoxic agents: DNA adducts and mutations. In: Cavalieri E and Rogan E (Eds.) JNCI Monograph: Estrogens as Endogenous Carcinogens in the Breast and Prostate. New York: Oxford Press, 2000. p 75-93.
3. Liehr J.G. Is estradiol a genotoxic mutagenic carcinogen? Endocr. Rev. 21:2000;40-54.
4. Das S.K., Taylor J.A., Korach K.S., Paria B.C., Dey S.K., Lubahn D.B. Estrogenic responses in estrogen receptor-alpha deficient mice reveal a distinct estrogen signaling pathway. Proc. Natl. Acad. Sci.: USA. 94:1997;12786-12791.
5. Bradlow H.L., Hershcopf R.J., Martucci C.P., Fishman J. Estradiol 16α-hydroxylation in the mouse correlates with mammary tumor incidence and presence of murine mammary tumor virus: a possible model for the hormonal etiology of breast cancer in humans. Proc. Natl. Acad. Sci.: USA. 82:1985;6295-6299.
6. Zhu B.T., Conney A.H. Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 19:1998;1-27.
7. Zhu B.T., Conney A.H. Is 2-methoxyestradiol an endogenous estrogen metabolite that inhibits mammary carcinogenesis? Cancer Res. 58:1998;2269-2277.
8. Mills L.H., Lee A.J., Parlow A.F., Zhu B.T. Preferential growth stimulation of mammary glands over uterine endometrium in female rats by a naturally occurring estradiol-17β-fatty acid ester. Cancer Res. 61:2001;5764-5770.
9. Mills L.H., Lee A.J., Zhu B.T. Naturally occurring estradiol-17β- fatty acid ester, but not estradiol-17β, preferentially induces the development of mammary tumor in female ACI rats. Proc. Am. Assoc. Cancer Res. 44:2003;786.
10. Chen S.H., Luo G.R., Wu X.S., Chen M., Zhao H.M. A new synthetic route to 2- and 4-methoxyestradiols by nucleophilic substitution. Steroids. 47:1986;63-66.
11. Utne T., Jobson R.B., Landgraf F.W. The synthesis of 2- and 4-bromoestradiol. J. Org. Chem. 33:1968;1654-1656.
12. Harrington P.M., Singh B.K., Szamosi I.T., Birk J.H. Synthesis and herbicidal activity of cyperin. J. Agri. Food Chem. 43:1995;804-808.
13. Weingarten H. Mechanism of the Ullmann condensation. J. Org. Chem. 29:1964;3624-3626.
14. Williams A.L., Kinney R.E., Bridger R.F. Solvent-assisted Ullmann ether synthesis. Reactions of dihydric phenols. J. Org. Chem. 32:1967;2501-2505.
15. Ullmann F. Ueber eine neue darstellungsweise von phenylathersalicylsaure. Chem. Ber. 37:1904;853-854.
16. Smith K., Jones D. A superior synthesis of diaryl ethers by the use of Ultrasound in the Ullmann reaction. J. Chem. Soc. Perkin Trans. 1:1992;407-408.
17. Palomo C, Oiarbide M, Lopez R, Gomez-Bengoa E. Phosphazene P-4-Bu-t base for the Ullmann biaryl ether synthesis. Chem Commun 1998;19:2091-2.