5α-hydroxy-6-oxoandrostane-3β-yl acetate | 4725-53-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5α-hydroxy-6-oxoandrostane-3β-yl acetate
• 英文别名: Androstan-6-one, 3-(acetyloxy)-5-hydroxy-, (3beta,5alpha)-；[(3S,5R,8S,9S,10R,13S,14S)-5-hydroxy-10,13-dimethyl-6-oxo-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 4725-53-5
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: LRIBANRFGRIPNC-FPYHTYPQSA-N

物化性质

• 熔点：
  220-221 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  451.4±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5α-hydroxy-6-oxoandrostane-3β-yl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 3β,5α-dihydroxy-androst-6-one
  参考文献：
  名称：

  Sulfuric acid hydrolysis of 3β-hydroxy-5α, 6α-epoxyandrostane

  摘要：

  DOI：

  10.1016/0039-128x(65)90094-2
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 chromium(VI) oxide 、 potassium carbonate 、 一水合肼 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 丁酮 、 二乙二醇 为溶剂， 反应 20.0h， 生成 5α-hydroxy-6-oxoandrostane-3β-yl acetate
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n

文献信息

• One-pot, high yield synthesis of α-ketols from Δ5-steroids
  作者：Jorge A.R. Salvador、Vânia M. Moreira、James R. Hanson、Rui A. Carvalho

  DOI：10.1016/j.steroids.2005.11.002

  日期：2006.3

  a-Hydroxy ketones (alpha-ketols) are present in many compounds with biological activity. Several methods are available for the preparation of alpha-ketols but only a few of them describe the synthesis of steroid alpha-ketols from olefins. In this work, a new system consisting of KMnO4/Fe(ClO4)(3)center dot nH(2)O was used in order to achieve the direct conversion of Delta(5)-steroids to their corresponding alpha-ketols, in high yields. Consideration of the probable reaction mechanism is provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to assign H-1 and C-13 resonances of some synthesized compounds. This method has potential for the preparation of alpha-hydroxy ketones of biological interest. (c) 2005 Elsevier Inc. All rights reserved.
• Synthesis of Cytotoxic 6<i>E</i>-Hydroximino-4-ene Steroids:  Structure/Activity Studies
  作者：Noé Deive、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1021/jm010867n

  日期：2001.8.1

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.
• Sulfuric acid hydrolysis of 3β-hydroxy-5α, 6α-epoxyandrostane
  作者：Jacqueline Weinman、Serge Weinman

  DOI：10.1016/0039-128x(65)90094-2

  日期：1965.12