6α-bromoacetoxy-4-androstene-3,17-dione | 113947-56-1

• 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: 6α-bromoacetoxy-4-androstene-3,17-dione
• 英文别名: [(6S,8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-6-yl] 2-bromoacetate
• CAS: 113947-56-1
• 化学式: C₂₁H₂₇BrO₄
• 分子量: 423.347
• InChiKey: LNWSVVQNLWDXSM-QQOOJKGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  3
• 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

• 作为产物：
  描述：

  6α-hydroxy-androst-4-ene-3,17-dione 、 溴乙酰溴 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以48%的产率得到6α-bromoacetoxy-4-androstene-3,17-dione
  参考文献：
  名称：

  Synthesis and evaluation of bromoacetoxy 4-androsten-3-ones as active site-directed inhibitors of human placental aromatase

  摘要：

  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.

  DOI：

  10.1016/0039-128x(86)90021-8

文献信息

• 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.