3β-acetoxyandrost-4-ene-6,17-dione | 19449-09-3

• 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: 3β-acetoxyandrost-4-ene-6,17-dione
• 英文别名: 3β-acetoxyandrost-4-en-17-one；3β-Acetoxy-Δ⁴-androstendion-(6,17)；[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-6,17-dioxo-2,3,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 19449-09-3
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: MGRXPDWGILOCHJ-AVZJEMISSA-N

物化性质

• 熔点：
  216-218 °C(Solv: acetone (67-64-1))
• 沸点：
  479.6±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxyandrost-4-ene-6,17-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 3β-acetoxyandrostane-6,17-dione
  参考文献：
  名称：

  Labler,L. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 2226 - 2237

  摘要：

  DOI：
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 chromium(VI) oxide 、 氯化亚砜 、 己二酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 丁酮 、 苯 为溶剂， 反应 28.0h， 生成 3β-acetoxyandrost-4-ene-6,17-dione
  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

• The scope and limitations of the reaction of δ5-steroids with mercury(II) trifluoroacetate
  作者：Peter L.D Ruddock、David J Williams、Paul B Reese

  DOI：10.1016/s0039-128x(98)00076-2

  日期：1998.12

  other mercury salts on the reaction were also studied. Treibs oxidation was successful in chloroform, carbon tetrachloride, and dibromomethane, but not in other solvents tested. 3β-Acetoxy-6-bromomercuriandrost-5-en-17-one was obtained in dibromomethane. Replacement of the reagent by mercury(II) trichloroacetate altered the intermediates formed but not the products. Mercury(II) tribromoacetate was unreactive

  摘要 研究了C-3 取代基对雄性5-烯与三氟乙酸汞(II) 在二氯甲烷中反应（改性Treibs 氧化）的影响。3β-Acyloxyandrost-5-en-17-ones 得到 3β-acyloxy-6β-hydroxyandrost-4-en-17-ones 伴随着 3β-acyloxy-6-chloromercuriandrost-5-en-17-ones。3β-Acetoxy-6β-trifluoroacetoxyandrost-4-en-17-one 和 3β-acetoxy-4β-trifluoroacetoxyandrost-5-en-17-one 是反应的中间体。氯汞类固醇的形成表明溶剂参与了反应。以 3α-acetoxyandrost-5-en-17-one 作为底物，观察到产物分布的完全逆转。3β-Haloandrost-5-en-17-ones 的主要产物反映了卤化物的
• 3β-hydroxyandrost-4-en-6-one derivatives as aromatase inhibitors
  作者：Mitsuteru Numazawa、Ayako Mutsumi、Masachika Tsuji

  DOI：10.1016/0039-128x(89)90004-4

  日期：1989.9

  The 3-formate (II), 3-acetate (III), 3-bromoacetate (IV), 3-propionate (V), 3-methyl ether (VI), and 3-deoxy-derivative (VII) of 3 beta-hydroxyandrost-4-ene-6,17-dione (I) were synthesized and tested in human placental microsomes for their ability to inhibit aromatase. II, III, and VII of this series were potent inhibitors of aromatase with the IC50's (1.7 and 3.3 microM) of the latter two comparable to that (1.2 microM) of 4-hydroxyandrostenedione. Kinetic studies showed that the three steroids are competitive inhibitors of the enzyme with Ki's of 16.0, 5.5, and 0.61 microM for II, III, and VII. Furthermore, II showed a time-dependent, pseudo-first order rate of inactivation of aromatase with Ki of 20.5 microM and kinact of 1.54 x 10(-2) min-1, while III gave a time-dependent, biphasic loss of the enzyme activity. NADPH and oxygen were required for the time-dependent inactivation and the substrate, androstenedione, prevented it.
• 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.
• Labler,L. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 2226 - 2237
  作者：Labler,L. et al.

  DOI：——

  日期：——