Synthesis of (5alpha)-17-azaandrostan-3-ols and (5alpha)-17-aza-D-homoandrostan-3-ols and their N-acylated derivatives.
Two groups of N-acylated D-azasteroids (4 and 5) were synthesized to explore structure-activity relationships for steroid modulation of GABA(A) receptor function. The target compounds were prepared conveniently from (5alpha)-3-hydroxyandrostan-17-ones (6 and 7) via the intermediate (5alpha)-17-aza-D-homoandrostan-3-ols (14 and 15) or (5alpha)-17-azaandrostan-3-ols (18 and 19) precursors in high overall yields. A Beckmann rearrangement and a Hofmann rearrangement were employed as two key steps in the synthetic sequences.
Jiang
X
X
Department of Chemistry, Nanjing University, 210093, Nanjing, People's Republic of China.
Wang
J
J
Hu
J
J
Ge
Z
Z
Hu
Y
Y
Hu
H
H
Covey
D F
DF
D000732:Androstanols / Q000138:chemical synthesis*; D001378:Azasteroids / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D013329:Structure-Activity Relationship; D013696:Temperature
D000732:Androstanols; D001378:Azasteroids