119169-66-3Relevant academic research and scientific papers
Synthesis of 3-carboxy-20-keto steroid, SB 209963, a 5α-reductase inhibitor, by palladium-catalyzed hydroxycarbonylation
Yu, Marvin S.,Baine, Neil H.
, p. 3123 - 3124 (1999)
SB 209963 was produced in three steps starting from 17β- carboxyandrost-4-en-3-one. A palladium-catalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions withOUt epimerization at C17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions.
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.
