4-羟基雌二醇3,4-二甲醚 | 26890-04-0

• 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: 4-羟基雌二醇3,4-二甲醚
• 英文名称: 4-hydroxyestradiol 3,4-dimethyl ether
• 英文别名: 4-hydroxyestradiol-3,4-dimethyl ether；4-hydroxyestradiol 3,4-dimethylether；(8R,9S,13S,14S,17S)-3,4-dimethoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 26890-04-0
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: MOXXDHQTZLRTMB-XQRBHQRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 1,3,5(10)-雌二醇-3,4,17beta-三醇 4-甲醚 以 甲醇 、 乙醚 为溶剂， 生成 4-羟基雌二醇3,4-二甲醚
  参考文献：
  名称：

  Methylation of Catechol Estrogen with Diazomethane

  摘要：

  通过薄层色谱法研究了二氮甲烷与邻苯二酚雌激素的甲基化反应的动态过程。在2-羟基雌激素反应中，C-3位置的羟基甲基化速率几乎与C-2羟基相同，而在4-羟基雌激素反应中，C-3羟基的甲基化速率是C-4羟基的2-3倍。在这些实验中，2-甲氧基雌酮、2-羟基雌酮3-甲基醚、4-甲氧基雌酮和4-羟基雌酮3-甲基醚的最高产率分别为32%、39%、13%和70%。此外，还描述了用三溴化硼脱除邻苯二酚雌激素二甲基醚的甲基化和4-羟基雌酮单甲基醚的合成。

  DOI：

  10.1248/cpb.31.3309

文献信息

• Clinical analysis on steroids. XXIX. Evidence for 4-hydroxylation of estradiol 17-sulfate by rat liver microsomes.
  作者：KAZUHIRO WATANABE、REIJI KIMURA、ITSUO YOSHIZAWA

  DOI：10.1248/cpb.32.2745

  日期：——

  When estradiol 17-sulfate was incubated with rat liver microsomes in the presence of a reduced nicotinamide adenine dinucleotide phosphate (NADPH)-generating system, 4-hydroxyestradiol 17-sulfate was obtained as a minor product accompanying the major metabolite, 2-hydroxyestradiol 17-sulfate. This 4-hydroxylation was shown to occur without cleavage of the conjugate group. At the substrate concentration of 200 μM, which is about twice the Km value of estradiol 17-sulfate 2-hydroxylase, the amounts of 2-and 4-hydroxylated products formed by liver microsomes from male rats were 15.03±1.43 and 0.23±0.01%, respectively. Analogous results were obtained with microsomes from female rats under the same conditions : the yields of 2-and 4-hydroxylated metabolites were 8.75±0.97 and 0.14±0.02%, respectively. Thus, the relative ratios of 2-and 4-hydroxylation of estradiol 17-sulfate were approximately 60 : 1 in both sexes. A synthesis of the authentic conjugate, 4-hydroxyestradiol 17-sulfate, and a method for its assay by high-performance liquid chromatography with an electrochemical detector are also described.

  当雌二醇17-硫酸盐与大鼠肝微粒体在还原型烟酰胺腺嘌呤二核苷酸磷酸（NADPH）生成系统的存在下孵育时，4-羟基雌二醇17-硫酸盐作为次要产物伴随主要代谢产物2-羟基雌二醇17-硫酸盐而产生。 4-羟基化反应无需共轭基断裂即可发生。 在底物浓度为200μM（约为雌二醇17-硫酸盐2-羟化酶Km值的两倍）时，雄性大鼠肝微粒体形成的2-和4-羟基化产物的量分别为15.03±1.43%和0.23±0.01%。 在相同条件下，雌性大鼠微粒体也获得了类似的结果：2-和4-羟基化代谢产物的产量分别为8.75±0.97%和0.14±0.02%。 因此，雌二醇17-硫酸盐的2-和4-羟基化反应的相对比率在两性中约为60：1。 还描述了4-羟基雌二醇17-硫酸盐的合成以及通过电化学检测器的高性能液
• Estrogenic compounds as antimitotic agents
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：EP1640009A1

  公开（公告）日：2006-03-29

  The application discloses methods of making medicaments for treating mammalian diseases characterised by abnormal cell mitosis by administering estradiol derivatives including those comprising colchicine or combretastatin A-4 structural motifs of general formulae found above in a dosage sufficient to inhibit cell mitosis. The application discloses novel compounds used in the methods.

  本申请公开了用于治疗以细胞有丝分裂异常为特征的哺乳动物疾病的药物的制造方法，其方法是施用雌二醇衍生物，包括含有上述通式中的秋水仙碱或考布他丁 A-4 结构基团的雌二醇衍生物，其剂量足以抑制细胞有丝分裂。该申请公开了用于上述方法的新型化合物。
• 2-Methoxyestradiol for the treatment of inflammatory disorders
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：EP1927359A2

  公开（公告）日：2008-06-04

  The applications discloses the treatment of inflammatory disorders, in particular those associated with rheumatoid, arthritis, gout, gouty arthritis and Behcet's syndrome, with 2-methoxyestradiol.

  该申请公开了用 2-甲氧基雌二醇治疗炎症性疾病，特别是与类风湿、关节炎、痛风、痛风性关节炎和白塞氏综合征有关的疾病。
• Estrogenic compounds as anti-mitotic agents
  申请人：D'Amato John Robert

  公开号：US20050020555A1

  公开（公告）日：2005-01-27

  The application discloses methods of treating mammalian diseases characterized by abnormal cell mitosis by administering estradiol derivatives including those comprising colchicine or combretastatin A-4 structural motifs of the general formulae found below in a dosage sufficient to inhibit cell mitosis. The application discloses novel compounds used in the methods.

  本申请公开了治疗以细胞有丝分裂异常为特征的哺乳动物疾病的方法，其方法是施用雌二醇衍生物，包括包含秋水仙碱或梳形他丁 A-4 结构基团的通式如下的衍生物，其剂量足以抑制细胞有丝分裂。 该申请公开了用于这些方法的新型化合物。
• EP0713393A4
  申请人：——

  公开号：EP0713393A4

  公开（公告）日：2000-10-25