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

Xin Jiang, Jie Wang, Jiaxin Hu, Zongming Ge, Yuefei Hu, Hongwen Hu, Douglas F. Covey

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Two groups of N-acylated D-azasteroids (4 and 5) were synthesized to explore structure-activity relationships for steroid modulation of GABAA receptor function. The target compounds were prepared conveniently from (5α)-3-hydroxyandrostan-17-ones (6 and 7) via the intermediate (5α)-17-aza-D-homoandrostan-3-ols (14 and 15) or (5α)-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.

Original languageEnglish
Pages (from-to)655-662
Number of pages8
JournalSteroids
Volume66
Issue number8
DOIs
StatePublished - 2001

Keywords

  • D-Azasteroids
  • GABA receptor
  • Synthesis

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