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

doi:10.1016/S0039-128X(01)00095-2

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 journal › Article › peer-review

20 Scopus citations

Abstract

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 (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 language	English
Pages (from-to)	655-662
Number of pages	8
Journal	Steroids
Volume	66
Issue number	8
DOIs	https://doi.org/10.1016/S0039-128X(01)00095-2
State	Published - 2001

Keywords

D-Azasteroids
GABA receptor
Synthesis

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10.1016/S0039-128X(01)00095-2

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

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.",

keywords = "D-Azasteroids, GABA receptor, Synthesis",

author = "Xin Jiang and Jie Wang and Jiaxin Hu and Zongming Ge and Yuefei Hu and Hongwen Hu and Covey, {Douglas F.}",

note = "Funding Information: We are grateful to the Education Ministry of China for financial support.",

year = "2001",

doi = "10.1016/S0039-128X(01)00095-2",

language = "English",

volume = "66",

pages = "655--662",

journal = "Steroids",

issn = "0039-128X",

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}

TY - JOUR

T1 - Synthesis of (5α)-17-azaandrostan-3-ols and (5α)-17-aza-D-homoandrostan-3-ols and their N-acylated derivatives

AU - Jiang, Xin

AU - Wang, Jie

AU - Hu, Jiaxin

AU - Ge, Zongming

AU - Hu, Yuefei

AU - Hu, Hongwen

AU - Covey, Douglas F.

N1 - Funding Information: We are grateful to the Education Ministry of China for financial support.

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

KW - D-Azasteroids

KW - GABA receptor

KW - Synthesis

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U2 - 10.1016/S0039-128X(01)00095-2

DO - 10.1016/S0039-128X(01)00095-2

M3 - Article

C2 - 11430998

AN - SCOPUS:0034743443

SN - 0039-128X

VL - 66

SP - 655

EP - 662

JO - Steroids

JF - Steroids

IS - 8

ER -

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

Abstract

Keywords

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