3-hydroxy-16β-(2-methoxyethylamino)estra-1,3,5(10)-trien-17-one | 137437-79-7

• 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-hydroxy-16β-(2-methoxyethylamino)estra-1,3,5(10)-trien-17-one
• CAS: 137437-79-7
• 化学式: C₂₁H₂₉NO₃
• 分子量: 343.466
• InChiKey: GNPYCDBOOPSWDJ-AGRFSFNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,3,5(10)-雌甾三烯-3,17-beta-二醇-16-酮 在 甲醇 作用下， 反应 2.0h， 生成 3-hydroxy-16β-(2-methoxyethylamino)estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Structure of the adduct of 16α-hydroxyestrone with a primary amine: evidence for the heyns rearrangement of steroidal D-ring α-hydroxyimines

  摘要：

  16-alpha-Hydroxyestrone, a product of estrogen 16-alpha-hydroxylation in humans that is suspected to be implicated in cell transformation, has been found to form stable adducts with nuclear components. The stable covalent adduct formed from 16-alpha-hydroxyestrone with 2-methoxyethylamine via the Heyns rearrangement of the alpha-hydroxyimine was identified as 3-hydroxy-17-beta-(2-methoxyethylamino)estra-1,3,5(10)-trien-16-one. Since the same product was obtained from 16-beta-hydroxyestrone with the amine, the alpha-hydroxyenamine is the most likely intermediate of the Heyns rearrangement. The adduct was fairly stable at 37 C in phosphate buffer (pH 7.4)/methanol (1:1 v/v), while the adduct formed from 16-oxoestradiol was disrupted reversely and completely within 6 hours. The evidence suggests that N-(3-hydroxy-16-oxoestra-1,3,5(10)-trien-17-beta-yl)amine is the partial structure of the stable adducts formed from D-ring alpha-ketol estrogens with proteins.

  DOI：

  10.1016/0039-128x(91)90068-7