Synthesis of (5 alpha)-17-azaandrostan-3-ols and (5 alpha)-17-aza-D-homoandrostan-3-ols and their N-acylated derivatives

Authors
Jiang, X Wang, J Hu, JX Ge, ZM Hu, YF Hu, HW Covey, DF
Citation
X. Jiang et al., Synthesis of (5 alpha)-17-azaandrostan-3-ols and (5 alpha)-17-aza-D-homoandrostan-3-ols and their N-acylated derivatives, STEROIDS, 66(8), 2001, pp. 655-662
Citations number
27
Categorie Soggetti
Biochemistry & Biophysics
Journal title
STEROIDS
ISSN journal
0039128X → ACNP
Volume
66
Issue
8
Year of publication
2001
Pages
655 - 662
Database
ISI
SICI code
0039-128X(200108)66:8<655:SO(AA(>2.0.ZU;2-9
Abstract
Two groups of N-acylated D-azasteroids (4 and 5) were synthesized to explor e structure-activity relationships for steroid modulation of GABA(A) recept or function. The target compounds were prepared conveniently from (5 alpha) -3-hydroxyandrostan-17-ones (6 and 7) via the intermediate (5 alpha)-17-aza -D-homoandrostan-3-ols (14 and 15) or (5 alpha)-17-azaandrostan-3-ols (18 a nd 19) precursors in high overall yields. A Beckmann rearrangement and a Ho fmann rearrangement were employed as two key steps in the synthetic sequenc es. (C) 2001 Elsevier Science Inc. All rights reserved.