5-bromo-3β-hydroxy-5α-androstan-6,17-dione 3-acetate | 54604-81-8

• 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: 5-bromo-3β-hydroxy-5α-androstan-6,17-dione 3-acetate
• 英文别名: 3β-acetoxy-5-bromo-5α-androstane-6,17-dione；3β-Acetoxy-5-brom-5α-androstan-6,17-dion
• CAS: 54604-81-8
• 化学式: C₂₁H₂₉BrO₄
• 分子量: 425.363
• InChiKey: SAJBBXHQFITLIA-SXWHVLJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-bromo-3β-hydroxy-5α-androstan-6,17-dione 3-acetate 以 吡啶 为溶剂， 反应 3.5h， 以83%的产率得到3β-acetoxyandrost-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
• 作为产物：
  描述：

  5-溴-3,6-二羟基雄甾烷-17-酮-3-乙酸酯 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.08h， 生成 5-bromo-3β-hydroxy-5α-androstan-6,17-dione 3-acetate
  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

• Grenville et al., Journal of the Chemical Society, 1957, p. 4105,4108
  作者：Grenville et al.

  DOI：——

  日期：——
• The oxidation of a steroidal bromohydrin revisited
  作者：Bojan Hamlin Jennings、Lauren Marie Yelle

  DOI：10.1016/0039-128x(81)90003-9

  日期：1981.1

  A comparative study was made of the reactions of 5-bromo-3 beta, 6 beta-dihydroxy-5 alpha-androstan-17-one 3-acetate (1) with lead tetraacetate alone and in the presence of iodine in both high intensity visible light and in total darkness using a variety of solvents. Markedly different product profiles were obtained under the different reaction conditions, making our results of both practical importance and theoretical interest.