92472-70-3Relevant articles and documents
Acylimidazolides as Versatile Synthetic Intermediates for the Preparation of Sterically Congested Amides and Ketones: A Practical Synthesis of Proscar
Bhattacharya, A.,Williams, J.M.,Amato, J.S.,Dolling, U.-H.,Grabowski, E.J.J.
, p. 2683 - 2690 (2007/10/02)
Acylimidazolides react with magnesium amides to produce carboxamides in excellent yields, whereas Fe(III) catalyzed cross coupling between acylimidazolide and Grignard reagents produce ketones in high yields.These methods were utilized to prepare the α-reductase inhibitor Proscar as well as various 17β-amide and ketone analogs of Δ1-4-aza-5α-androsten-3-one.
Azasteroids as Inhibitors of Rat Prostatic 5α-Reductase
Rasmusson, Gary H.,Reynolds, Glenn F.,Utne, Torleif,Jobson, Ronald B.,Primka, Raymond L.,et al.
, p. 1690 - 1701 (2007/10/02)
A series of A-ring heterocyclic steroids has been prepared and tested for inhibition of rat prostatic steroid 5α-reductase in vitro.Strinkingly high inhibitory activity was found with a group of 17β-substituted 4-methyl-4-aza-5α-androstan-3-ones.These compounds were prepared from 3-keto-Δ4-precursors by oxidative (O3 or NaIO4-KMnO4) A-ring cleavage followed, in turn, by ring closure with an amine and hydrogenation over platinum catalyst.Other A-ring azasteroids were made by Beckmann rearrangement of oximes of 2-oxo-A-nor-, 3-oxo- and 4-oxo-5α-androstanes.An A-nor-2-oxo-3-azasteroid was prepared by oxidative decarbonylation of a precursor 2,3-dioxo-4-azasteroid with m-chloroperbenzoic acid.A-ring modifications of the 4-azasteroids included Δ1-unsaturation, 2- and 4-substituents, and 3-carbonyl replacements.Side chains at the 17-position were varied with an emphasis on carboxylate derivatives (salts, esters, and amides).
