(17beta)-3-甲氧基雌甾-1,3,5(10)-三烯-2,17-二醇 | 5976-65-8

• 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: (17beta)-3-甲氧基雌甾-1,3,5(10)-三烯-2,17-二醇
• 英文名称: 2-Hydroxy-Estradiol-3-methyl ether
• 英文别名: 2-hydroxy-3-methoxyestra-1,3,5(10)-trien-2,17β-diol；estra-1,3,5(10)-trien-2,3,17β-triol 3-methyl ether；2-hydroxyestradiol 3-methyl ether；3-Methoxyestra-1,3,5(10)-trien-2,17β-diol；2-Hydroxy-oestradiol-3-methylaether；2-Hydroxyestradiol-3-methyl ether；(8R,9S,13S,14S,17S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2,17-diol
• CAS: 5976-65-8
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: MMKYSUOJWFKECQ-SSTWWWIQSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

3-O-甲基雌二醇是2-羟基雌二醇的人类已知代谢物。

3-O-methoxyestradiol is a known human metabolite of 2-hydroxyestradiol.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  (17beta)-3-甲氧基雌甾-1,3,5(10)-三烯-2,17-二醇 在 吡啶盐酸盐 作用下， 生成 2-羟基雌酚酮
  参考文献：
  名称：

  Catechol Derivatives of Estrogens¹

  摘要：

  DOI：

  10.1021/jo01074a026
• 作为产物：
  描述：

  4-bromo-2,3-dihydroxy-1,3,5⁽¹⁰⁾-estratrien-17-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 β-glucuronidase 、 无水碳酸镉 、 palladium dichloride 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 48.5h， 生成 (17beta)-3-甲氧基雌甾-1,3,5(10)-三烯-2,17-二醇
  参考文献：
  名称：

  New synthesis of 2-hydroxyestrogen 2-monoglucuronides.

  摘要：

  本文描述了合成儿茶酚雌激素 2-葡萄糖醛酸单酯的新合成路线。通过利用 3-羟基基团与 C-4 处大体积取代基的空间相互作用，选择性地将葡萄糖醛酸残基引入 C-2 羟基基团。为此，4-溴-2-羟基雌三醇 16,17-二乙酸酯被用作关键中间体。在碳酸镉存在下，儿茶酚与甲基 α-乙酰溴葡萄糖醛酸酯的 Koenigs-Knorr 反应优先朝向 C-2 羟基基团进行。随后的还原脱卤和碱性水解反应提供了所需的 2-羟基雌三醇 2-葡萄糖醛酸单酯。以类似的方式，2-羟基雌二醇和 2-羟基雌酮 2-葡萄糖醛酸单酯也可以制备。

  DOI：

  10.1248/cpb.36.419

文献信息

• Clinical analysis on steroids. XXII Preparation and high-performance liquid chromatographic determination of guaiacol estrogen 17.BETA.-conjugates: The enzymatic O-methylation products of 2-hydroxyestradiol 17.BETA.-conjugates.
  作者：KAZUHIRO WATANABE、ITSUO YOSHIZAWA

  DOI：10.1248/cpb.30.3231

  日期：——

  For the direct assay of the enzymatic O-methylation products of 2-hydroxyestradiol 17β-sulfate (2) and 17β-glucuronide (3), the corresponding guaiacol estrogens have been prepared as authentic specimens and their high-performance liquid chromatography (HPLC) was investigated. The materials synthesized were : potassium 3-hydroxy-2-methoxyestra-1, 3, 5 (10)-trien-17β-yl sulfate (7), potassium 2-hydroxy-3-methoxyestra-1, 3, 5 (10)-trien-17β-yl sulfate (13), potassium [3-hydroxy-2-methoxyestra-1, 3, 5 (10)-trien-17β-yl-β-D-glucopyranosid] uronate (9), and potassium [2-hydroxy-3-methoxyestra-1, 3, 5 (10)-trien-17β-yl-β-D-glucopyranosid]-uronate (15). These sulfates and glucuronides were separated quantitatively by reversed-phase HPLC. The separation was performed with a mixture of acetate buffer (50 mM, pH 5.0) and methanol (50 : 50) as the mobile phase on a column of ODS SIL. The eluates were monitored in terms of the absorbance at 280 nm. Calibration curves between the amounts of conjugated guaiacols and the peak heights on chromatograms were all linear. The results obtained by proposed HPLC method for the quantification of O-methylated products obtained by the incubation of 2 and/or 3 with purified rat liver catechol O-methyltransferase in the presence of (3H3C)-S-adenosyl-L-methionine were in good agreement with the results obtained by a different procedure, the reverse isotope dilution method.

  为了直接测定2-羟基雌二醇-17β-硫酸酯（2）和17β-葡萄糖苷酸（3）的酶促O-甲基化产物,已制备了相应的愈创木酚雌激素作为标准样品,并研究了其高效液相色谱法（HPLC）。合成的物质有:钾盐3-羟基-2-甲氧基雌-1,3,5（10）-三烯-17β-基硫酸酯（7）,钾盐2-羟基-3-甲氧基雌-1,3,5（10）-三烯-17β-基硫酸酯（13）,钾盐[3-羟基-2-甲氧基雌-1,3,5（10）-三烯17β-基-β-D-吡喃葡萄糖]苷酸（9）及钾盐[2-羟基-3-甲氧基雌-1,3,5（10）-三烯-17β-基-β-D-吡喃葡萄糖]苷酸（15）。这些硫酸酯和葡萄糖苷酸通过反相HPLC可以定量分离。分离以乙酸缓冲液（50mM,pH5.0）和甲醇（50∶50）混合液作为流动相,使用ODS-SIL柱进行。以280nm处的吸光度监测流出液。上样愈创木酚量与色谱峰高间的标准曲线均为线性。采用本HPLC方法对2和/或3与纯化的鼠肝儿茶酚-O-甲基转移酶在含（3H3C）-S-腺苷-L-甲硫氨酸条件下的体外甲基化产物进行的定量测定结果,与另一种方法,反向同位素稀释法所得结果具有很好的一致性。
• Methylation of Catechol Estrogen with Diazomethane
  作者：MASANORI TERANISHI、YOUICHI FUJII、MITSURU YAMAZAKI、SUSUMU MIYABO

  DOI：10.1248/cpb.31.3309

  日期：——

  Dynamic aspects of methylation of catechol estrogen with diazomethane were investigated by means of thin-layer chromatography. The methylation rate of the hydroxyl group at the C-3 position was almost the same as that of the C-2 hydroxyl group in the reaction of 2-hydroxyestrogen, and 2-3 times that of the C-4 hydroxyl group in the reaction of 4-hydroxyestrogen. In these experiments, the maximum yields of 2-methoxyestrone, 2-hydroxyestrone 3-methyl ether, 4-methoxyestrone and 4-hydroxyestrone 3-methyl ether were 32, 39, 13 and 70%, respectively. In addition, demethylation of catechol estrogen dimethyl ethers with boron tribromide and synthesis of 4-hydroxyestrone monomethyl ethers are described.

  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。
• [EN] ESTRATRIENE DERIVATIVES<br/>[FR] DERIVES D'ESTRATRIENE
  申请人：CRYPTOPHARMA PTY LTD

  公开号：WO2004101595A1

  公开（公告）日：2004-11-25

  Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness associated with asthma. The compounds also supress inflammation. The compounds are a class of estratriene derivates, and includes various derivatives of 2-methoxyestradiol comprising a group A, including a substituted aromatic substituent in the 2-, 6- or 17- position.

  调节间叶细胞功能的化合物和方法，例如平滑肌和成纤维细胞增殖或细胞因子表达，以及治疗与间叶细胞功能相关的疾病，例如与哮喘相关的气道高反应性。这些化合物还抑制炎症。这些化合物是一类雌三烯衍生物，包括各种2-甲氧基雌二醇衍生物，其中包括A组，包括在2-、6-或17-位置有取代芳香基团。
• Estratriene Derivatives
  申请人：Stewart George Alastair

  公开号：US20070275935A1

  公开（公告）日：2007-11-29

  Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness associated with asthma. The compounds also suppress inflammation. The compounds are a class of estratriene derivates, and includes various derivatives of 2-methoxyestradiol comprising a group A, including a substituted aromatic substituent in the 2-, 6- or 17-position.

  化合物和方法用于调节间充质细胞功能，例如平滑肌和成纤维细胞增殖或细胞因子表达，并用于治疗与间充质细胞功能相关的疾病，例如与哮喘相关的气道过度反应。这些化合物还可抑制炎症。这些化合物是一类雌三烯衍生物，包括2-甲氧基雌二醇的各种衍生物，其中包括A组，包括2-，6-或17-位取代芳香基取代物。
• A simple, convenient and chemoselective formylation of sterols by Vilsmeier reagent
  作者：Vandana Srivastava、Arvind Singh Negi、J.K. Kumar、M.M. Gupta

  DOI：10.1016/j.steroids.2006.03.005

  日期：2006.7

  Vilsmeier reagent (DMF-POCl3) was used as an efficient formylating agent. Several sterols having sec-hydroxyl group at 3/17-position have been modified into respective formate esters. The method is simple, mild, chemoselective and provides sec-alcoholic protection in good yields. (c) 2006 Elsevier Inc. All rights reserved.