<(3)H,(14)C>16α-bromo-4-androstene-3,17-dione | 110879-85-1

• 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: <(3)H,(14)C>16α-bromo-4-androstene-3,17-dione
• CAS: 110879-85-1
• 化学式: C₁₉H₂₅BrO₂
• 分子量: 371.283
• InChiKey: WSFGMEHHPWEPNC-QPANJCIISA-N

反应信息

• 作为反应物：
  描述：

  <(3)H,(14)C>16α-bromo-4-androstene-3,17-dione 在 sodium hydroxide 作用下， 以 吡啶 、 水 为溶剂， 反应 2.0h， 以45 mg的产率得到<1,2-(3)H,4-(14)C>16α-hydroxyandrostenedione
  参考文献：
  名称：

  Preparation of (1,2-3H,4-14C)16.ALPHA.-hydroxyandrostenedione and its use for radiometric determination of human placental aromatase activity.

  摘要：

  [1, 2-3H, 4-14C] 16α-Hydroxyandrostenedione (4) (3H, 3.20 mCi/mmol; 3H/14C = 222) was synthesized from commercially available [1, 2-3H, 4-14C] dehydroepiandrosterone (1) through bromination at C-16α of the 17-ketone 1 and controlled alkaline hydrolysis of the 16α-bromoketone 3, obtained from the brominated product 2 by 8 N CrO3 oxidation followed by p-toluenesulfonic acid treatment, as key reactions. The tritium distribution of the labeled 16α-ketol 4 was determined by chemical and biochemical methods to be 47% at C-1α, 18% at C-2α, and 35% at the β-side of C-1 and C-2. When the labeled ketol 4 was incubated with human placental microsomes and reduced nicotinamide adenine dinucleotide phosphate, the rate of 3H2O release into the medium was dependent upon protein concentration and incubation time. Aromatase activity obtained by the radiometric assay was comparable to that determined by the high-performance liquid chromatographic method.

  DOI：

  10.1248/cpb.35.2448
• 作为产物：
  描述：

  在 chromium(VI) oxide 、 对甲苯磺酸 作用下， 生成 <(3)H,(14)C>16α-bromo-4-androstene-3,17-dione
  参考文献：
  名称：

  Preparation of (1,2-3H,4-14C)16.ALPHA.-hydroxyandrostenedione and its use for radiometric determination of human placental aromatase activity.

  摘要：

  [1, 2-3H, 4-14C] 16α-Hydroxyandrostenedione (4) (3H, 3.20 mCi/mmol; 3H/14C = 222) was synthesized from commercially available [1, 2-3H, 4-14C] dehydroepiandrosterone (1) through bromination at C-16α of the 17-ketone 1 and controlled alkaline hydrolysis of the 16α-bromoketone 3, obtained from the brominated product 2 by 8 N CrO3 oxidation followed by p-toluenesulfonic acid treatment, as key reactions. The tritium distribution of the labeled 16α-ketol 4 was determined by chemical and biochemical methods to be 47% at C-1α, 18% at C-2α, and 35% at the β-side of C-1 and C-2. When the labeled ketol 4 was incubated with human placental microsomes and reduced nicotinamide adenine dinucleotide phosphate, the rate of 3H2O release into the medium was dependent upon protein concentration and incubation time. Aromatase activity obtained by the radiometric assay was comparable to that determined by the high-performance liquid chromatographic method.

  DOI：

  10.1248/cpb.35.2448