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2005
Steroids
U 0300
26- 118
7α,11β-Dimethyl-19-nortestosterone: A Potent and Selective Androgen Response
Modulator with Prostate-Sparing Properties. — Introduction of both 7α- and
11β-methyl groups into nortestosterone results in enhancement of androgenic activity
together with increased separation of effects on muscle and ventral prostate compared
with the two monomethyl homologues. Starting from 11β-methylnortestosterone (I),
the synthesis of 7α-analogue (VIII) is achieved by conjugate addition of a methyl group
utilizing lithium dimethyl cuprate, prepared in situ from dimethyl sulfide/cuprous complex and methyl lithium (V). Compound (VIII) seems to be an attractive candidate for
a potent and selective androgen response modulator in hormonal contraception and
replacement therapy. — (COOK, C. E.; KEPLER, J. A.; Bioorg. Med. Chem. Lett. 15
(2005) 4, 1213-1216; Org. Med. Chem., Res. Triangle Inst., Research Triangle Park,
NC 27709, USA; Eng.) — H. Hoennerscheid
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