2-Ethenylestradiol

• 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: 2-Ethenylestradiol
• 英文别名: (8R,9S,13S,14S,17S)-13-methyl-2-vinyl-7,8,9,11,12,13,14,15,16,17-decahydro-6Hcyclopenta[a]phenanthrene-3,17-diol；2-Ethenyl estradiol；(8R,9S,13S,14S,17S)-2-ethenyl-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: BFKMKTXWLSOMEF-SSGANFLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Ethenylestradiol 在 咪唑 、 palladium on activated charcoal 、 氢气 、 环己酮 、 aluminum isopropoxide 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2-ethyl-3-O-(t-butyldimethylsilyl)estrone
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of new analogs of the anti-cancer agent 2-methoxyestradiol: potent inhibitors of angiogenesis

  摘要：

  对甾体2-甲氧基雌二醇的结构活性研究揭示了一种新的类似物，它表现出强大的抑制血管生成和细胞毒性效应。

  DOI：

  10.1039/c5ra03570h
• 作为产物：
  描述：

  雌二醇 在 三乙胺 、 magnesium chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 生成 2-Ethenylestradiol
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of new analogs of the anti-cancer agent 2-methoxyestradiol: potent inhibitors of angiogenesis

  摘要：

  对甾体2-甲氧基雌二醇的结构活性研究揭示了一种新的类似物，它表现出强大的抑制血管生成和细胞毒性效应。

  DOI：

  10.1039/c5ra03570h

文献信息

• Synthesis, Antitubulin and Antimitotic Activity, and Cytotoxicity of Analogs of 2-Methoxyestradiol, an Endogenous Mammalian Metabolite of Estradiol That Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site
  作者：Mark Cushman、Hu-Ming He、John A. Katzenellenbogen、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00012a003

  日期：1995.6

  In order to define the structural parameters associated with the antitubulin activity and cytotoxicity of 8-methoxyestradiol, a mammalian metabolite of estradiol, an array of analogs was synthesized and evaluated. The potencies of the new congeners as inhibitors of tubulin polymerization and colchicine binding were determined using tubulin purified from bovine brain, and the cytotoxicities of the new compounds were studied in a variety of cancer cell cultures. Maximum antitubulin activity was observed in estradiols having unbranched chain substituents at the 2-position with three non-hydrogen atoms. 2-Ethoxyestradiol and 2-((E)-1-propenyl)-estradiol were substantially more potent than 2-methoxyestradiol itself. The tubulin polymerization inhibitors in this series displayed significantly higher cytotoxicities in the MDA-MB-435 breast cancer cell line than in the other cell lines studied. The potencies of the analogs as cytotoxic and antimitotic agents in cancer cell cultures correlated with their potencies as inhibitors;of tubulin polymerization, supporting the hypothesis that inhibition of tubulin polymerization is the mechanism of the cytotoxic action of 2-methoxyestradiol and its congeners. Several of the more potent analogs were tested in an estrogen receptor binding assay, and their affinities relative to estradiol were found to be very low.
• Mild Arming and Derivatization of Natural Products via an In(OTf)₃-Catalyzed Arene Iodination
  作者：Cong-Ying Zhou、Jing Li、Satyamaheshwar Peddibhotla、Daniel Romo

  DOI：10.1021/ol100587j

  日期：2010.5.7

  Iodination of arene-containing natural products employing N-iodosuccinimide catalyzed by In(OTf)(3) at ambient temperature is reported as a versatile and mild method for natural product derivatization amenable to small scale. This process facilitates natural product derivatization of arene moieties for SAR studies, homo- and heterodimerization of natural products, and also conjugation with reporters such as biotin via subsequent metal-mediated coupling reactions.
• Synthesis, biological evaluation and molecular modeling of new analogs of the anti-cancer agent 2-methoxyestradiol: potent inhibitors of angiogenesis
  作者：Eirik Johansson Solum、Jing-Jy Cheng、Ingebrigt Sylte、Anders Vik、Trond Vidar Hansen

  DOI：10.1039/c5ra03570h

  日期：——

  Structural-activity studies on the steroid 2-methoxyestradiol revealed a new analog that exhibited potent inhibition of angiogenesis and cytotoxic effects.

  对甾体2-甲氧基雌二醇的结构活性研究揭示了一种新的类似物，它表现出强大的抑制血管生成和细胞毒性效应。