3β-methoxyandrost-4-ene-6,17-dione | 133233-44-0

• 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-methoxyandrost-4-ene-6,17-dione
• 英文别名: (3S,8R,9S,10R,13S,14S)-3-methoxy-10,13-dimethyl-2,3,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-6,17-dione
• CAS: 133233-44-0
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: YMUKHCWRZBKVLF-VLLQHRMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴-3,6-二羟基雄甾烷-17-酮-3-乙酸酯 在 氢氧化钾 、 jones reagent 、 silver(l) oxide 作用下， 以 吡啶 、 乙醇 、 丙酮 为溶剂， 反应 12.08h， 生成 3β-methoxyandrost-4-ene-6,17-dione
  参考文献：
  名称：

  3β-hydroxyandrost-4-en-6-one derivatives as aromatase inhibitors

  摘要：

  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.

  DOI：

  10.1016/0039-128x(89)90004-4

文献信息

• 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.