6-羟基-6-(羟基甲基)-雄甾-1,4-二烯-3,17-二酮 | 184972-11-0

• 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
• 中文名称: 6-羟基-6-(羟基甲基)-雄甾-1,4-二烯-3,17-二酮
• 英文名称: 6α/β-hydroxy-6α/β-hydroxymethylandrosta-1,4-dien-3,17-dione
• 英文别名: 6α/β-hydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3,17-dione；6ξ-hydroxy-6ξ-hydroxymethylandrosta-1,4-diene-3,17-dione；6-Hydroxy-6-(hydroxymethyl)androsta-1,4-diene-3,17-dione；(8R,9S,10R,13S,14S)-6-hydroxy-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 184972-11-0
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: NQQZWPXWZWALLC-YCNUYBHRSA-N

物化性质

• 沸点：
  534.8±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、二氯甲烷（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  依西美坦 在 高氯酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 6-羟基-6-(羟基甲基)-雄甾-1,4-二烯-3,17-二酮
  参考文献：
  名称：

  Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione)

  摘要：

  Exemestane (6-methylenandrosta-1,4-diene-3,17-dione; FCE 24304) is an orally active irreversible aromatase inhibitor which is in phase II clinical evaluation for the potential therapy of postmenopausal breast cancer. A series of exemestane analogs, with modifications at the 6-methylene group and with additional reduction at the 17-keto group, were synthesized as potential metabolites and tested in vitro for their effect on human placental aromatase. All these new analogs were found to be less potent in inhibiting aromatase than exemestane. The most effective compound was the 17beta-hydroxy-derivative (compound 2), which is 2.6-fold less potent than exemestane [50% inhibitory concentration (IC50) 69 and 27 nM, respectively]. The various C-6 modified derivatives of the 17-oxo series were found to inhibit the aromatase enzyme in the following descending order: 6-methylene (exemestane) > 6-spirooxirane (6) > 6beta-hydroxymethyl (11) > 6-hydroxymethyl (7) > 6beta-carboxy (13), showing IC50 values of 27, 206, 295, 2,300, and 7,200 nM, respectively. The 17beta-hydroxy analogs of some of the above mentioned compounds were also synthesized (3, 4, 12) and found to be 3-8-fold less potent than the corresponding 17-keto analogs.

  DOI：

  10.1016/0039-128x(93)90029-m