(3S,20S)-20-formyl-5α-pregn-7-en-3-yl-acetate | 23738-34-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,20S)-20-formyl-5α-pregn-7-en-3-yl-acetate
• 英文别名: (3S,20S)-20-formylpregn-7-en-3-yl acetate；3β-acetoxy-23,24-dinor-5α-chol-7-en-22-al；[(3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2S)-1-oxopropan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 23738-34-3
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: PSHFPHZGNDYMPD-SZCYIGQKSA-N

物化性质

• 熔点：
  136-138 °C(Solv: water (7732-18-5); acetone (67-64-1))
• 沸点：
  465.6±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,20S)-20-formyl-5α-pregn-7-en-3-yl-acetate 在 Lindlar's catalyst Wilkinson's catalyst 、 乙基溴化镁 、 氢气 、 二异丁基氢化铝 、 丙酸 作用下， 以 乙酸乙酯 、 甲苯 、 xylene 为溶剂， 反应 13.0h， 生成 星鱼甾醇
  参考文献：
  名称：

  Stereospecific synthesis of the marine sterol stellasterol, (22E,24S)-5.alpha.-ergosta-7,22-dien-3.beta.-ol

  摘要：

  DOI：

  10.1021/jo00321a041
• 作为产物：
  描述：

  星鱼甾醇 在 吡啶 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 16.03h， 生成 (3S,20S)-20-formyl-5α-pregn-7-en-3-yl-acetate
  参考文献：
  名称：

  Ergosterol analogs as inhibitors of cyclin dependent kinase 8

  摘要：

  DOI：

  10.1016/j.steroids.2022.108965

文献信息

• Die Synthese von 5α‐Stigmastatrien‐(7. 22.25)‐ol‐(3β)
  作者：Wolfgang Sucrow、Björn Girgensohn

  DOI：10.1002/cber.19701030314

  日期：1970.3

  bei der Claisen-Umlagerung mit dem keten-O.N-acetal5 das Amid 7 ergibt. Lithiumalanatreduktion und CopeAbbau führen zum Titelsterin 1. Aus den epimeren Formen von 4 erhält man in stereospezifischer Reaktion die beiden 24-epimeren Sterine 1. Die Stereochemie der Claisen-Umlagerung wird diskutiert.

  达斯Äthinylcarbinol 3 AUS3β乙酰氧基22.23-DINOR-5α-cholen-（7）-aldehyd（2）UND Butin-（1）-ylmagnesiumbromid wird的Zum Allylalkohol 4 hydriert，DER贝DER克莱森-Umlagerung MIT DEM keten- Ò。N-缩醛5 das Amid 7 ergibt。锂钛酸还原和应对Titelsterin 1。AUS巢穴epimeren福曼冯4 erhält男性在stereospezifischer Reaktion模具beiden 24 epimeren Sterine 1。Die StereochEMie der Claisen -Umlagerung wird diskutiert。
• Die Synthese von 5α‐Stigmastadien‐(7.25)ol‐(3β)
  作者：Wolfgang Sucrow、Björn Girgensohn

  DOI：10.1002/cber.19701030313

  日期：1970.3

  Das Titelsterin (1a) wird aus 3β-Acetoxy-22.23-dinor-5α-cholen-(7)-aldehyd (3) über den homologen Aldehyd 5, den Ketoester 9 und das Abbau-Ketolacetat 2b des Naturstoffs nach bekannten Methoden synthetisch dargestellt.

  Das Titelsterin（1a）与3β-乙酰氧基22.23-dinor-5α-cholen-（7）-醛（3）的同系物Aldehyd 5，酮酸酯9和das Abbau-Ketolacetat 2b des Naturstoffs nach bekannten Methoden合成物。
• Lathosterol side chain amides—A new class of human lathosterol oxidase inhibitors
  作者：Martin Giera、Delphine Renard、Florian Plössl、Franz Bracher

  DOI：10.1016/j.steroids.2007.10.015

  日期：2008.3

  Inhibition of cholesterol biosynthesis offers the opportunity for treatment of cardiovascular diseases. Numerous enzymes are involved in the post-squalene part of this biosynthesis, and selective inhibitors for almost all of the enzymes involved there have been described in literature. The only exception is the enzyme lathosterol oxidase (EC 1.14.21.6), for which up to now no selective inhibitor has been found. Up to date only triarimol has been reported as a weak inhibitor. In this paper we report on lathosterol side chain amides as a new class of selective lathosterol. oxidase inhibitors. To study the influence of different sterol amides on inhibition of this enzyme, numerous compounds were prepared and the sterol patterns resulting from incubation of HL 60 cells with these enzyme inhibitors were monitored in a whole cell screening assay by means of GUMS analysis. Small alkyl residues at the amide nitrogen (hydrogen and methyl) lead to an inhibition of the enzyme Delta 24-reductase, the N-ethyl and N-propyl derivatives show a dual action, inhibiting both Delta 24-reductase and lathosterol oxidase. Lathosterol- derived amides with larger substituents (butyl, isobutyl, tert-butyl, pentyl) at the amide nitrogen were found to be selective inhibitors of lathosterol oxidase. The corresponding 3 beta-acetoxy derivatives showed comparable activities and can be considered as prodrugs, since they are transformed into the 3 beta-hydroxy derivatives under the test conditions, as proven by HPLC analysis. (C) 2007 Elsevier Inc. All rights reserved.
• Sucrow,W. et al., Chemische Berichte, 1971, vol. 104, p. 3689 - 3703
  作者：Sucrow,W. et al.

  DOI：——

  日期：——
• DE964775
  申请人：——

  公开号：——

  公开（公告）日：——