2-羟基炔雌醇 | 50394-89-3

• 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-羟基炔雌醇
• 英文名称: 17alpha-Ethynyl-2-hydroxyestradiol
• 英文别名: 19-nor-17α-pregna-1,3,5(10)-trien-20-yne-2,3,17β-triol；2-hydroxy-17-α-ethynylestradiol；2-hydroxy-17α-ethynylestradiol；2-hydroxy-ethynylestradiol；2-Hydroxyethinylestradiol；(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-2,3,17-triol
• CAS: 50394-89-3
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: KQJCDKMHNQVWDV-BKRJIHRRSA-N

物化性质

• 熔点：
  220-223°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基炔雌醇 在 copper(ll) sulfate pentahydrate 、 叠氮基三甲基硅烷 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  细胞色素 P450 中的 1,2,3-三唑-血红素相互作用：功能强大的三唑-水-血红素复合物

  摘要：

  与咪唑 (IMZ) 和 1,2,4-三唑 (1,2,4-TRZ) 相比，等排的 1,2,3-三唑 (1,2,3-TRZ) 在细胞色素 P450 (CYP ) 抑制剂。这是令人惊讶的，因为 1,2,3-TRZ 很容易通过“点击”化学获得。为了理解 CYP 抑制剂中 1,2,3-TRZ 的这种代表性不足，对未取代的 IMZ、1,2,4-TRZ 和 1,2,3-TRZ 进行了热力学和密度泛函理论计算研究。结果表明，1,2,3-TRZ 对血红素铁的亲和力较低，包括一个可能源自溶剂-1,2,3-TRZ 相互作用的大的不利熵项；这种差异不仅仅是由于血红素-配体相互作用焓的差异。此外，1,2,3-TRZ 片段被整合到一个成熟的 CYP3A4 底物和基于机制的灭活剂中，17-α-乙炔雌二醇 (17EE)，通过点击化学。这种衍生的 17-click 产生的光谱与低自旋铁血红素铁（II 型）一致，而 17EE

  DOI：

  10.1021/bi300744z
• 作为产物：
  描述：

  炔雌醇 在 盐酸 、 sodium periodate 、 硝酸 、 sodium hydrogensulfite 、 溶剂黄146 、 sodium nitrite 作用下， 生成 2-羟基炔雌醇
  参考文献：
  名称：

  Convenient large scale preparation of catechol estrogens

  摘要：

  2-Hydroxyestrone, 2-hydroxyestradiol-17beta, 2-hydroxy-17alpha-ethynylestradiol, 2-hydroxyestriol, 4-hydroxyestrone, 4-hydroxyestradiol-17beta, 4-hydroxy-17alpha-ethynylestradiol and 4-hydroxyestriol are prepared on a preparative scale from the corresponding aminophenols using a new inverse oxidation procedure. By the synthesis described both the 2- and 4-hydroxylated estrogens are available in high yields.

  DOI：

  10.1016/0039-128x(76)90010-6

文献信息

• Modified, hydroxy-substituted aromatic structures having cytoprotective activity
  申请人：Washington University

  公开号：US20020103178A1

  公开（公告）日：2002-08-01

  The present invention is directed to modified, hydroxy-bearing aromatic ring structures having cytoprotective activity. More specifically, in a first embodiment the present invention is directed to phenolic compounds, and in particular steriods (e.g., estrogens), wherein a non-fused polycyclic, hydrophobic substituent is attached to the hydroxy-substituted A-ring thereof. The present invention is further directed to a process for conferring cytoprotection to a population of cells involving the administration of the compound.

  本发明涉及具有细胞保护活性的改性、含羟基的芳香环结构。更具体地说，在第一实施例中，本发明涉及酚类化合物，特别是类固醇（例如雌激素），其中非融合的多环、疏水基团附着于其羟基取代的A环上。本发明还涉及一种通过给予化合物的方法，赋予一群细胞细胞保护作用的过程。
• MODIFIED, HYDROXY-SUBSTITUTED AROMATIC STRUCTURES HAVING CYTOPROTECTIVE ACTIVITY
  申请人：Covey F. Douglas

  公开号：US20060009438A2

  公开（公告）日：2006-01-12

  Abstract of the Disclosure The present invention is directed to a process for conferring cytoprotection on a population of cells which comprises administering to that population of cells a compound comprising a hydroxy-substituted aromatic ring structure and a non-fused polycyclic, hydrophobic substituent attached thereto. In particular, the present invention is directed to such a process wherein the administered compound is phenolic, such as a steriod (e.g., estrogen), and has a non-fused polycyclic, hydrophobic substituent attached to the hydroxy-substituted A-ring thereof.

  本发明涉及一种用于给细胞群体提供细胞保护的方法，该方法包括向该细胞群体中投与一种化合物，所述化合物包含一个羟基取代的芳香环结构和一个附着于其上的非融合多环、疏水取代基。特别地，本发明涉及一种这样的方法，其中所投与的化合物为酚类，例如类固醇（例如雌激素），并且具有附着于其羟基取代的A环上的非融合多环、疏水取代基。
• Synthesis of compounds of potential value in the radioimmunoassay of 17α-ethynylestradiol and mestranol
  作者：P. Narasimha Rao

  DOI：10.1016/0039-128x(74)90150-0

  日期：1974.2
• A new efficient synthetic method for 2- and 4-hydroxy-17α-ethynyIestradiol
  作者：Xie Rugang、Chen Qiuyun、Xie Jin、Zhao Huaming

  DOI：10.1016/0039-128x(90)90085-p

  日期：1990.11

  The reaction of ethyl magnesium bromide and 17 alpha-ethynylestradiol with formaldehyde in the presence of triethyl phosphate or hexamethylphosphoramide gave the 2- and 4-formyl-17 alpha-ethynylestradiol in high yield. Treatment of the formyl derivatives with an alkaline solution of hydrogen peroxide in tetrahydrofuran afforded the corresponding catechols in almost quantitative yield. This new synthetic method was far superior to other methods, especially concerning simplicity, selectivity, and high yields.
• Ozonation of ethinylestradiol in aqueous-methanolic solution: direct monitoring by electrospray ionization mass spectrometry
  作者：Karla M. Vieira、Clésia C. Nascentes、Rodinei Augusti

  DOI：10.1590/s0103-50532010000500004

  日期：——

  The ozonolysis of ethinylestradiol (1), a synthetic steroidal estrogen, in an aqueous-methanolic solution was investigated. HPLC-UV analyses revealed that 1 was completely consumed after a 20 min reaction time either at pH 5 or 8. ESI(-)-MS (electrospray ionization mass spectrometry in the negative ion mode) monitoring also revealed the continuous consumption of 1 (detected as [1 - H](-) of m/z 295) concomitantly with the emergence of oxidation products. Chemical structures were proposed for these products based on the data of MS and MS/MS (the m/z values and fragmentation profiles of the anionic specie, respectively). These data, in conjunction with the well-established knowledge about the reactivity of organic molecules toward ozone in aqueous solution, were evaluated and an unprecedented reaction route for the ozonation of 1 could thus be suggested. Hence, the first step in this reaction sequence was ascribed to involve a 1,3-dipolar cycloaddition of ozone at the phenolic ring of 1 yielding the di-hydroxylated product 2 (detected as [2 - H](-) of m/z 311). The loss of acetylene as the unique dissociation channel for [2 - H](-) thus confirmed that such hydroxylation occurred at the phenolic ring rather than the acetylenic moiety of 1. Subsequent oxidations were proposed to be the origin of a number of other products, all of them bearing the COOH functionally (this was verified by the characteristic loss of CO2 during the dissociation of the related deprotonated molecules). The ESI(-)-MS records also revealed notable differences between the reaction conducted at pH 5 and 8, i.e. at slightly acid or basic media, respectively.