2-甲氧基乙炔雌二醇 | 22415-44-7

• 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
• 中文名称: 2-甲氧基乙炔雌二醇
• 英文名称: 17a-Ethynyl-2-methoxyestradiol
• 英文别名: 2-methoxy-17α-ethynylestradiol；2-methoxy-17-ethynylestradiol；(8R,9S,13S,14S,17R)-17-ethynyl-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 22415-44-7
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: NRGDXTWZJCEVEB-PVHGPHFFSA-N

物化性质

• 熔点：
  159-161°C
• 沸点：
  476.0±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（微量）、吡啶（微量）、甲醇（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基乙炔雌二醇 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2-羟基炔雌醇
  参考文献：
  名称：

  Synthesis of compounds of potential value in the radioimmunoassay of 17α-ethynylestradiol and mestranol

  摘要：

  DOI：

  10.1016/0039-128x(74)90150-0
• 作为产物：
  描述：

  2-甲氧基雌素酮 、 乙炔氢锂 在 乙二胺 作用下， 以 二甲基亚砜 为溶剂， 生成 2-甲氧基乙炔雌二醇
  参考文献：
  名称：

  Synthesis of compounds of potential value in the radioimmunoassay of 17α-ethynylestradiol and mestranol

  摘要：

  DOI：

  10.1016/0039-128x(74)90150-0

文献信息

• Analogs of [(triethylsilyl)ethynyl]estradiol as potential antifertility agents
  作者：Richard H. Peters、David F. Crowe、Mitchell A. Avery、Wesley K. M. Chong、Masato Tanabe

  DOI：10.1021/jm00398a014

  日期：1988.3

  detail and the oral antifertility and oral estrogenic potencies of the compounds are described and compared. Of the various triethylsilyl compounds examined for an antifertility to estrogenic activity ration that would be more beneficial than that of a present agent, only 23 manifested the desired ratio. Compound 18, which was 66% as effective as ethynyl estradiol as an antifertility agent, had 0.1% of the

  制备了17种α-乙炔基类固醇并将其衍生化为相应的三乙基甲硅烷基化合物2-35，检查了抗生育性与雌激素活性的比，该比将比目前使用的试剂更有利。在所评估的三乙基甲硅烷基化合物中，只有23种显示了所需的比率，尽管另外两个没有三乙基甲硅烷基部分的化合物（18和26）具有相似的特性。在作者先前对乙炔基雌二醇衍生物的研究中，发现即使少量存在硅也是有益的。甲硅烷基衍生物显示出雌激素活性的降低以及口服抗生育活性水平的保持。关于内分泌失调和处方避孕药的不良副作用，这一发现是积极的。在目前的研究中，结合C-21三乙基甲硅烷基部分，研究了乙炔基雌二醇甾体核的A，B，C和D环结构变化的影响。详细描述了乙炔化和三乙基甲硅烷基化的一般方法，并描述了该化合物的口服抗生育能力和口服雌激素能力，并进行了比较。在各种三乙基甲硅烷基化合物中检测到的对雌激素活性比的抗育性比本发明试剂更有利，只有23种表现出所需的比例。作为抗生育
• 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。
• Chromatographic patterns of urinary ethynyl estrogen metabolites in various populations
  作者：Mary C. Williams、Joseph W. Goldzieher

  DOI：10.1016/0039-128x(80)90001-x

  日期：1980.9

  Radioactive mestranol (ME) and/or ethynylestradiol (EE) were administered to women in Nigeria, Sri Lanka, and the USA, and the types and patterns of radioactive urinary conjugates examined by Sephadex LH-20 chromatography. There are no differences in the total excretion of urinary radioactivity over 3 days. Consistent geographic differences appear to be present in the proportion of 3-, 17-, and 3,17-glucuronides. If confirmed on larger population samples, these observations may indicate significant geographic differences in the hepatic metabolism of ethynyl estrogens. High performance liquid chromatographic patterns of the urinary aglycone metabolites of ME and EE were examined in a number of women. The separation was accomplished on a Chromegaprep Diol column with a gradient of isopropanol in heptane. Ethynyl estrogen metabolism shows considerable individual variation. EE is usually the principal compound escreted following ME or EE administration. Unmetabolized ME is present in the ME profiles. The profiles of EE and ME are similar, with EE demonstrating a more complex pattern. Oxidative metabolism occurs chiefly at positions 2, 6 and 16 and is fairly extensive in the USA subjects. The Sri Lankan women generally show less of the oxidative products and the Nigerian group display a notable lack of oxidative metabolism. There is no difference in the metabolic patterns of long-term oral contraceptive users vs. non-users. Using silver sulfoethylcellulose column chromatography, from 14.1 to 34.7% of the excreted radiolabeled aglycones are non-ethynyl (i.e., either D-homo or de-ethynylated estrogens).