3-Ethoxycarbonylmethoxy-17β-hydroxyestra-1,3,5(10)-triene | 41164-35-6

• 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: 3-Ethoxycarbonylmethoxy-17β-hydroxyestra-1,3,5(10)-triene
• 英文别名: 3-ethyloxycarbonylmethylenoxyestradiol；ethyl estradiol-3-oxyacetate；ethyl 2-{[(17β)-17-hydroxyestra-1,3,5(10)-trien-3-yl]oxy}acetate；3-(ethoxycarbonylmethoxy)estradiol；3-ethoxycarbonylmethylene-17β-estradiol；ethyl estradiol-3-O-acetate；ethyl 2-[[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]acetate
• CAS: 41164-35-6
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: RESMDRRILLMGEL-KOVVAJLHSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  495.2±45.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Ethoxycarbonylmethoxy-17β-hydroxyestra-1,3,5(10)-triene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 为溶剂， 反应 8.0h， 生成 3-<2'-(2''-Hydroxyethylamino)ethoxy>-17β-(p-toluenesulfonoxy)estra-1,3,5(10)-triene
  参考文献：
  名称：

  Omar; Farghaly; Hazzaa, Pharmazie, 1983, vol. 38, # 7, p. 445 - 448

  摘要：

  DOI：
• 作为产物：
  描述：

  雌二醇 、 溴乙酸乙酯 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0~55.0 ℃ 、100.0 kPa 条件下， 反应 16.5h， 以88%的产率得到3-Ethoxycarbonylmethoxy-17β-hydroxyestra-1,3,5(10)-triene
  参考文献：
  名称：

  具有口服抗骨质疏松活性的新型雌二醇-RGD八肽偶联物的合成，评价和3D QSAR分析

  摘要：

  为了增强雌激素替代疗法（ERT）的效力，降低副作用并改善雌二醇的口服特性，已制备了6种新型雌二醇-RGD八肽偶联物。在卵巢切除的小鼠骨质疏松模型中，每天口服剂量为110.3 nmol / kg，它们的抗骨质疏松活性显着高于雌二醇和雌二醇-RGD四肽偶联物，它们的血栓形成和子宫内膜增生的风险明显低于雌二醇和雌二醇-RGD四肽共轭物的结合力。使用Cerius2的QSAR模块，对接受小鼠的雌二醇-RGD肽结合物的股骨重量和股骨灰分重量进行了3D QSAR。的[R 2 高达0.995和0.988的3D QSAR方程式表明，它们能够预测结合物的相对精确的抗骨质疏松活性。

  DOI：

  10.1016/j.ejmech.2008.09.036

文献信息

• 1-天冬缀-3-雌醇 ,其制备 ,纳米结构,抗骨质疏松活性和应用
  申请人：首都医科大学

  公开号：CN107686500A

  公开（公告）日：2018-02-13

  本发明公开了下式的1分子天冬氨酸缀合3分子雌二醇的化合物(简称1‑天冬缀‑3‑雌醇)，公开了它的制备方法，公开了它的纳米结构，进一步公开了它在化学阉割的雌性小鼠骨质疏松模型上的抗骨质疏松作用。因而本发明公开了它在制备抗骨质疏松药物中的应用前景。
• Nω-Asp-Nα-(17β-雌二醇-3-乙酰基)-Lys,其 制备 ,活性和应用
  申请人：首都医科大学

  公开号：CN109942662B

  公开（公告）日：2020-07-28

  本发明公开了下式的N ω ‑Asp‑N α ‑(17β‑雌二醇‑3‑乙酰基)‑Lys,公开了它的制备方法,公开了它与Ca 2+ 络合的逐级稳定常数,进一步公开了它在小鼠骨质疏松模型上的抗骨质疏松作用,因而本发明公开了它在制备抗骨质疏松药物中的应用。
• Immunosensors for Estradiol and Ethinylestradiol Based on New Synthetic Estrogen Derivatives: Application to Wastewater Analysis
  作者：Hussein Kanso、Lise Barthelmebs、Nicolas Inguimbert、Thierry Noguer

  DOI：10.1021/ac303406c

  日期：2013.2.19

  and screen-printed electrodes as sensing platforms. Four synthetic estrogen derivatives containing either a carboxylic group or an amine group at the C-3 position were synthesized and covalently bound to MBs functionalized with amine or carboxyl groups, respectively. The assay was based on competition between the free and immobilized estrogen for the binding sites of the primary antibody, with subsequent

  基于磁珠（MBs）作为固体支持物和丝网印刷电极作为传感平台的使用，描述了用于灵敏检测17-β雌二醇（E2）和炔雌醇（EE2）的新型电化学免疫传感器。合成了四种在C-3位上含有一个羧基或一个胺基的合成雌激素衍生物，它们分别共价键合到被胺或羧基官能化的MBs上。该测定基于游离和固定的雌激素之间对一抗结合位点的竞争，随后使用碱性磷酸酶标记的二抗进行揭示。进行了初步的比色测试，以验证合成雌激素对免疫识别的适用性并优化不同的实验参数。在第二步骤中，通过方波伏安法（SWV）进行电化学检测。在优化的工作条件下，电化学免疫传感器对E2和EE2表现出高度敏感的响应，检测限分别为1和10 ng / L。与其他激素的交叉反应性评估显示出极好的选择性。研发的设备已成功应用于加标水和天然水样品的分析。这些新型的免疫传感器具有灵敏度高，易于制备，制备时间短，检测时间短等优点。与其他激素的交叉反应性评估显示出极好的选择
• Improved Anti-Osteoporosis Potency and Reduced Endometrial Membrane Hyperplasia During Hormone Replacement Therapy with Estrogen−RGD Peptide Conjugates
  作者：Yu Xiong、Ming Zhao、Chao Wang、Heng Wei Chang、Shiqi Peng

  DOI：10.1021/jm070242a

  日期：2007.7.1

  To improve the specificity and potency of estrogen replacement therapy therapeutics while also minimizing the side effects such as bone resorption and thickening of the uterine wall, a series of novel estrogen-derived conjugates estradiol-3-RGD, estradiol-17-RGD, and estrone-3-RGD peptides have been prepared. In a mouse model, intraperitoneal (i.p.) administration of these estrogen-RGD peptide conjugates resulted in decreased serum concentrations of calcium and alkaline phosphatase, as well as increased levels of calcium, phosphorus, and minerals in the mouse femur. Furthermore, the anti-osteoporosis action of these conjugates followed a dose-dependent manner and was accompanied with no observable effects on endometrial cell hyperplasia. In addition to all of these compounds exhibiting biological activity when administered by the i.p. route, we were particularly pleased to note that the estradiol-3-RGD and estradiol-17-RGD conjugates were both orally active.
• 3D QSAR of novel estrogen–RGD peptide conjugates: Getting insight into structural dependence of anti-osteoporosis activity and side effect of estrogen in ERT
  作者：Ming Zhao、Jiangyuan Liu、Xiaoyi Zhang、Li Peng、Chunyu Li、Shiqi Peng

  DOI：10.1016/j.bmc.2009.03.057

  日期：2009.5

  To explore the structural dependence of the oral potency and side effect of estrogen-RGD peptide conjugates, here six novel conjugates were prepared via introducing RGD-tetrapeptides into both 3- and 17-positions of estradiol, and introducing RGD-octapeptides into 3-position of estrone. In an ovariectomized mouse model they exhibited higher anti-osteoporosis activity and lower side effect than estrogen. For 3D QSAR analysis the anti-osteoporosis activities of nine known conjugates estrogen-RGD tetrapeptide conjugates were also provided. Using Cerius(2) module their 3D QSAR analysis was performed, four equations with high r(2) values were established, and the structural dependence of the oral potency and side effect of them was elucidated. (C) 2009 Elsevier Ltd. All rights reserved.