2-Iodoestradiol-17-acetate | 110370-91-7

• 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
• 英文名称: 2-Iodoestradiol-17-acetate
• 英文别名: 2-iodoestradiol 17β-acetate；2-Iodoestradiol 17beta-acetate；[(8R,9S,13S,14S,17S)-3-hydroxy-2-iodo-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 110370-91-7
• 化学式: C₂₀H₂₅IO₃
• 分子量: 440.321
• InChiKey: YSTGAOMPENJTFN-BKRJIHRRSA-N

物化性质

• 沸点：
  451.8±45.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Iodoestradiol-17-acetate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以58.5%的产率得到2-碘雌二醇
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00012a003
• 作为产物：
  描述：

  estradiol 在 copper diacetate 、 一氯化碘 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 2-Iodoestradiol-17-acetate
  参考文献：
  名称：

  雌二醇 17β-醋酸酯的新型区域选择性碘化

  摘要：

  使用乙酸中的碘-乙酸铜 (II) 直接碘化雌二醇 17β-乙酸酯 (3)，以高产率区域选择性地提供 2-碘衍生物。讨论了使用几种方法对 3 进行碘化。另一方面，3 与碘-溴化铜 (II) 的反应得到 4-溴衍生物 (7)，而不是 2-碘化合物。3-甲氧基-17β-乙酰氧基-1,3,5(10)-雌三烯 (4) 与碘-氯化铜 (II)-氯化铁 (III) 在乙酸中反应得到 2- (10) 和 4 -碘 (11) 衍生物。

  DOI：

  10.1246/bcsj.59.2459

文献信息

• Synthesis and Characterization of Hybrid Dimeric Steroid Spiroketals
  作者：Martín A. Iglesias-Arteaga、Martha C. Mayorquín-Torres、Mauricio Maldonado-Domínguez、Marcos Flores-Álamo

  DOI：10.1055/a-1647-7610

  日期：2022.2

  The synthesis of six dimeric spiroketals bearing an estradiol half fused to the 5α- or 5β-epimers of androstane, cholestane, and spirostane nuclei is described. The synthetic procedure comprises the Sonogashira­ coupling of different steroid alkynes with 2-iodoestradiol 17-monoacetate, followed by Pd-catalyzed spiroketalization. The structural characterization of the obtained hybrid dimers was performed

  描述了六个二聚体 spiroketals 的合成, 其中雌二醇一半与雄甾烷、胆甾烷和螺甾烷核的 5α-或 5β-差向异构体融合。合成过程包括不同类固醇炔烃与 2-碘雌二醇 17-单乙酸酯的 Sonogashira 偶联，然后是 Pd 催化的 spiroketalization。使用 1D 和 2D NMR 技术的组合对获得的混合二聚体进行结构表征，并辅以 DFT 计算。所得化合物之一的单晶 X 射线衍射证实了所提出的结构。
• Synthesis and characterization of a highly fluorescent benzofuran dimer derived from estradiol
  作者：Gerardo I. Santiago‐Sampedro、Martha C. Mayorquín‐Torres、Andrés Aguilar‐Granda、Martin A. Iglesias‐Arteaga

  DOI：10.1002/jhet.4783

  日期：2024.4

  Pd-catalyzed cyclization of a fluorescent dimer in which two cores of the potent estrogenic estradiol are bridged by the 1,4-diethynil benzene moiety led to a steroid dimer bearing the 1,4-di(benzofuran-2-yl)benzene. The obtained compound showed an intense blue fluorescence characterized by a broad emission band between 350 and 550 nm, with four maxima at 384, 403, 435, and 456 nm. The benzofuran dimer

  钯催化荧光二聚体的环化，其中强效雌激素雌二醇的两个核心通过 1,4-二乙炔基苯部分桥接，产生带有 1,4-二（苯并呋喃-2-基）苯的类固醇二聚体。所得化合物显示出强烈的蓝色荧光，其特征在于350至550 nm之间的宽发射带，在384、403、435和456 nm处有四个最大值。与合成前体相比，苯并呋喃二聚体的量子产率提高了 18 倍。
• 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.
• Novel Regioselective Iodination of Estradiol 17β-Acetate
  作者：C. Akira Horiuchi、Akinori Haga、J. Yasuo Satoh

  DOI：10.1246/bcsj.59.2459

  日期：1986.8

  Direct iodination of estradiol 17β-acetate (3) using iodine–copper(II) acetate in acetic acid afforded the 2-iodo derivative regioselectively in high yield. The iodination of 3 using several methods was discussed. On the other hand, the reaction of 3 with iodine–copper(II) bromide gave the 4-bromo derivative (7), not the 2-iodo compound. The reaction of 3-methoxy-17β-acetoxy-1,3,5(10)-estratriene (4)

  使用乙酸中的碘-乙酸铜 (II) 直接碘化雌二醇 17β-乙酸酯 (3)，以高产率区域选择性地提供 2-碘衍生物。讨论了使用几种方法对 3 进行碘化。另一方面，3 与碘-溴化铜 (II) 的反应得到 4-溴衍生物 (7)，而不是 2-碘化合物。3-甲氧基-17β-乙酰氧基-1,3,5(10)-雌三烯 (4) 与碘-氯化铜 (II)-氯化铁 (III) 在乙酸中反应得到 2- (10) 和 4 -碘 (11) 衍生物。