2α-hydroxyandrost-4-ene-3,17-dione | 571-17-5

• 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: 2α-hydroxyandrost-4-ene-3,17-dione
• 英文别名: 2α-hydroxy-4-androstene-3,17-dione；2alpha-Hydroxyandrost-4-ene-3,17-dione；(2R,8R,9S,10R,13S,14S)-2-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 571-17-5
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: TUUUEQXMRRIGLT-ZEHJPDPISA-N

物化性质

• 沸点：
  475.3±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2α-hydroxyandrost-4-ene-3,17-dione 在 碘化铵 、 2-巯基乙醇 作用下， 反应 0.75h， 生成
  参考文献：
  名称：

  甲酸甲酯的深入GC-MS / MS碎片分析和异美3-酮4-烯羟基类固醇的质谱鉴别评估。

  摘要：

  芳香酶抑制剂福尔马坦（4-羟基雄烷-4-烯-3,17-二酮）被列入世界反兴奋剂机构的《运动中禁用物质清单》。但是，它也像2-，6-和11-羟基异构体一样内源性地发生。这项研究的目的是使用GC / EI-MS区分不同的异构体，以增强检测的信心和测定的选择性。

  DOI：

  10.1002/rcm.8937
• 作为产物：
  描述：

  2α,3α-Dihydroxy-5α-cholestan-6-one 以 甲醇 为溶剂， 反应 72.0h， 以40%的产率得到2α,3α,6α-trihydroxy-5α-androstan-17-one
  参考文献：
  名称：

  Microbial degradation of 2α, 3α-dihydroxy-5α-cholestan-6-one by Mycobacterium vaccae

  摘要：

  2-alpha,3-alpha-Dihydroxy-5-alpha-cholestan-6-one (3), which had the substitution pattern of brassinosteroids in the A/B-ring moiety, was transformed by Mycobacterium vaccae to give 2-alpha,3-alpha,6-alpha-trihydroxy-5-alpha-androstan-17-one (4) and 2-alpha-hydroxyandrost-4-ene-3,17-dione (5). The structures of these compounds were determined by spectroscopic methods, especially H-1 nuclear magnetic resonance studies.

  DOI：

  10.1016/0039-128x(91)90021-m

文献信息

• Synthesis and evaluation of a new series of mechanism-based aromatase inhibitors
  作者：D. Lesuisse、J. F. Gourvest、C. Hartmann、B. Tric、O. Benslimane、D. Philibert、J. P. Vevert

  DOI：10.1021/jm00087a013

  日期：1992.5

  A series of new 4-(alkylthio)-substituted androstenedione analogues was designed as potential suicide inhibitors of aromatase on the basis of mechanistic considerations on the mode of action of the enzyme. Their synthesis and biological evaluation are described. Among the most interesting are the 4-[(difluoromethyl)thio]-, 4-[(fluoromethyl) thio]-, and 4-[(chloromethyl)thio]androstenediones 12,13, and 14 with respective IC50's of 2.7,0.8, and 0.94-mu-M. Compound 12 was a reversible inhibitor of aromatase while compounds 13 and 14 displayed time-dependent kinetics of inhibition with respective K(I)'s and half-times of inactivation of 30 nM and 3.75 min for 13 and 30 nM and 3 min for 14. The inhibition of aromatase by 14 was NADPH-dependent, and was protected by the presence of substrate (0.5-1-mu-M), while beta-mercaptoethanol (0.5 mM) failed to protect the enzyme from inactivation. Dialysis failed to reactivate aromatase previously inactivated by 14. The mechanistic implications of these findings are
• Synthesis and evaluation of bromoacetoxy 4-androsten-3-ones as active site-directed inhibitors of human placental aromatase
  作者：Mitsuteru Numazawa、Masachika Tsuji、Yoshio Osawa

  DOI：10.1016/0039-128x(86)90021-8

  日期：1986.11

  2 alpha-Bromoacetoxy (II), 6-bromoacetoxy (VII and X), and 19-bromoacetoxy (XII) derivatives of androstenedione and 17 beta-bromoacetoxy compounds (III, IV, XIII-XVI) were synthesized as potential affinity-labeling reagents for aromatase. 6 alpha-Bromoacetoxy derivative VII was the most potent inhibitor of human placental microsomal aromatase activity among this series. Its inhibitory activity was higher than that of the parent 6 alpha-hydroxy compound V, although other bromoacetates showed weaker inhibition of aromatase than the corresponding alcohols. The bromoacetates (except the 6 beta-bromoacetate X) inhibited aromatase activity in a time-dependent manner in the absence of NADPH, and the enzyme inactivation was blocked by the addition of androstenedione to the incubates. Kinetic analysis of the time- and concentration-dependent inhibition by the 6 beta-bromo-17 beta-bromoacetoxy compound XV gave an apparent Ki of 25 microM and kinact of 0.027 min-1.
• Mann, John; Pietrzak, Barbara, Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2681 - 2685
  作者：Mann, John、Pietrzak, Barbara

  DOI：——

  日期：——
• [EN] METHODS FOR COMPREHENSIVE PROFILING OF STEROID METABOLOME<br/>[FR] PROCÉDÉS POUR UN PROFILAGE COMPLET D'UN MÉTABOLOME STÉROÏDIEN
  申请人：UNIV CALIFORNIA

  公开号：WO2015161078A1

  公开（公告）日：2015-10-22

  The present invention provides a method for quantitating at least 100 steroids in a biological sample using ultra-performance liquid chromatography-tandem mass spectrometry. The present invention also provides a method for detecting an imbalance in steroid metabolism or the presence of cancer in an individual.
• In‐depth gas chromatography/tandem mass spectrometry fragmentation analysis of formestane and evaluation of mass spectral discrimination of isomeric 3‐keto‐4‐ene hydroxy steroids
  作者：Annette Sophie Kollmeier、Xavier Torre、Christian Müller、Francesco Botrè、Maria Kristina Parr

  DOI：10.1002/rcm.8937

  日期：2020.12.30

  The aromatase inhibitor formestane (4‐hydroxyandrost‐4‐ene‐3,17‐dione) is included in the World Anti‐Doping Agency’s List of Prohibited Substances in Sport. However, it also occurs endogenously as do its 2‐, 6‐ and 11‐hydroxy isomers. The aim of this study is to distinguish the different isomers using GC/EI‐MS for enhanced confidence in detection and selectivity for determination.

  芳香酶抑制剂福尔马坦（4-羟基雄烷-4-烯-3,17-二酮）被列入世界反兴奋剂机构的《运动中禁用物质清单》。但是，它也像2-，6-和11-羟基异构体一样内源性地发生。这项研究的目的是使用GC / EI-MS区分不同的异构体，以增强检测的信心和测定的选择性。