119169-84-5Relevant academic research and scientific papers
Vinyl fluoride as a mimic of the 'intermediate' enol form in the 5α-reductase transformation: Synthesis and in vitro activity of (N-1′,1′-dimethylethyl)-3-haloandrost-3,5-diene-17β- carboxamides
Li, Xun,Singh, Shankar M.,Luu-The, Van,Cote, Jean,Laplante, Sylvie,Labrie, Fernand
, p. 55 - 60 (2007/10/03)
(N-1′,1′-Dimethylethyl)-3-haloandrost-3,5-diene-17ss- carboxamides (9-11) and the methyl ester 8 were prepared from 3-chloro/bromoandrost-3,5-diene-17β-carboxylic chloride/bromide (6/7), which were obtained from pregnenolone. In comparison with finasteride and 4-MA, compounds 8-11 showed very weak inhibitory activity (≤10% inhibition) on human type I 5 α-reductase (transfected 293 cells) at 100 and 1000 nM concentrations. Against the type II enzyme, chloro compounds 8 and 9, and bromo 10 had no effect at 100 nM concentration, however, they were weak inhibitors of the type II (6.0% 50 = 480 nM) was observed with the 3-vinyl fluoride analogue 11.
Improved Syntheses of Epristeride, a Potent Human 5α-Reductase Inhibitor
Baine, Neil H.,Owings, Franklin F.,Kline, Donald N.,Resnick, Theodore,Ping, Li-Jen,et al.
, p. 5987 - 5989 (2007/10/02)
Two improved syntheses of a potent human 5α-reductase inhibitor, epristeride, SK&F 105657, are described.The first synthesis starts from methyl 3-oxoandrost-4-ene-17β-carboxylate (1), which is converted to epristeride (5) in four synthetic steps in 44percent overall yield.The second synthesis starts from commercially available 3-oxoandrost-4-en-17β-carboxylic acid (7), which is converted to epristeride (5) in two synthetic steps in 63percent overall yield.Both syntheses are suitable for large scale production and have been employed to produce kilograms supplies of epristeride in high purity.
