17-(2-methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol | 137437-73-1

• 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: 17-(2-methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol
• 英文别名: (8R,9S,13S,14S,16R)-17-(2-methoxyethylimino)-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,16-diol
• CAS: 137437-73-1
• 化学式: C₂₁H₂₉NO₃
• 分子量: 343.466
• InChiKey: ZASBHVFYNQCOLL-YRIDSSQKSA-N

物化性质

• 沸点：
  510.9±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17-(2-methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol 在 甲醇 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.33h， 生成 17β-(2-methoxyethylamino)estra-1,3,5(10)-triene-3,16β-diol
  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
• 作为产物：
  描述：

  3,16alpha-二羟基雌甾-1,3,5(10)-三烯-17-酮3,16-二乙酸酯 、 2-甲氧基乙胺 反应 3.0h， 以100%的产率得到17-(2-methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol
  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

文献信息

• Effect of metal ions on the stable adduct formation of 16α-hydroxyestrone with a primary amine via the Heyns rearrangement
  作者：Shinichi Miyairi、Kaoru Maeda、Tomoyuki Oe、Toyoaki Kato、Akira Naganuma

  DOI：10.1016/s0039-128x(98)00118-4

  日期：1999.4

  16 alpha-Hydroxyestrone (16 alpha-OHE1), one of the major estrogen metabolites in humans that may plays a role in cell transformation, has been found to form stable adducts with nuclear proteins. The mechanism for the formation of a stable covalent adduct of 16 alpha- OHE1 with protein has been postulated via the Heyns rearrangement after Schiff base formation. The Heyns rearrangement on the steroidal D-ring alpha-hydroxyimine was investigated using 17-(2-methoxyethylimino)estra- 1,3,5(10)-triene-3,16 alpha-diol as a model intermediate. Rates of the Heyns rearrangement and hydrolysis of the steroidal alpha-hydroxyimine were determined by a high-performance liquid chromatography (HPLC) simultaneously. The Heyns rearrangement was demonstrated to be optimum at pH 6.2 and the reaction rate at physiological pH 7.3-7.5, was more than 90% of that at the optimum pH. On the other hand, modulator(s) to the reactions were also examined. According to our previous finding of the proton-mediated mechanism of the Heyns rearrangement, the effects of cationic metal ions on the reactions were examined with 29 metal chlorides. Five metal ions, Pt4+, Cu2+, Ni2+, Co2+, and Mn2+, suppressed the formation of Heyns product significantly while Fe2+, Y3+, Gd3+, and Er3+ slightly increased it. The suppression rate was synergistically enhanced by the combination of pt(4+) with Co2+, Cu2+, or Ni2+. These results suggest the five metal ions, Pt4+, Cu2+, Ni2+, Co2+, and Mn2+, reduce the formation of the Heyns product in vivo and, therefore, would be useful tools to clarify the implication of the stable adduct formation of 16 alpha-OHE1 with protein. (C) 1999 Elsevier Science Inc. All rights reserved.