Steroids p. 157 - 169 (1993)
Update date:2022-07-31
Topics:
French, Andrew N.
Wilson, Scott R.
Welch, Michael J.
Katzenellenbogen, John A.
In an effort to assist in the preparation of ligands for the study of the estrogen receptor (ER), we have developed a new synthesis of 7α-substituted estradiols.The key step in the synthesis involves a copper-catalyzed, α-selective, 1,6-conjugate addition of 4-pentenyl magnesium bromide to a suitably protected 6-dehydrotestosterone derivative.Desaturation and then reductive aromatization of the resulting 7α-pentenyl androgen gave the 7α-pentenylestradiol in good yields.The α-stereoselectivity of this addition in the testosterone series, compared with the 19-nortestosterone series, is significantly improved by the presense of the C-19 methyl group, which shields the beta face from attack.A key intermediate was functionalized further by substitution with fluorine-18 to provide a potential imaging agent for positron emission tomography, and by conjugation with a BODIPY (Molecular Probes Inc., Eugene, OR, USA fluorophore to make a fluorescent probe for the estrogen receptor.The synthesis and biological evaluation of these analogs is presented, as well as a discussion of the improvements in the synthetic procedure.Keywords: steroids; estrogen receptor; fluorescence; breast tumor imaging; fluorine-18; 7α-substituted estrogen
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Doi:10.1021/jo00071a034
(1993)Doi:10.1021/ol403078e
(2014)Doi:10.1021/np400683h
(2013)Doi:10.1021/ol403281t
(2014)Doi:10.1021/om400933k
(2013)Doi:10.1016/0031-9422(93)85278-Y
(1993)