17α-[(4-formylphenyl)]ethynylestra-1,3,5-(10)triene-3,17β-diol | 918803-11-9

• 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: 17α-[(4-formylphenyl)]ethynylestra-1,3,5-(10)triene-3,17β-diol
• 英文别名: 17α-[(4-formylphenyl)ethynyl]estra-1,3,5(10)-triene-3,17β-diol；(13S,16S,17S)-16-((4-hydroxyphenyl)ethynyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol；4-[2-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]benzaldehyde
• CAS: 918803-11-9
• 化学式: C₂₇H₂₈O₃
• 分子量: 400.518
• InChiKey: NEXZOSJLHWLQPV-VKINHPFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17α-[(4-formylphenyl)]ethynylestra-1,3,5-(10)triene-3,17β-diol 在 甲醇 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N-[2-[[4-[2-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]phenyl]methylamino]ethyl]acetamide
  参考文献：
  名称：

  激素-PAMAM树状大分子共轭物：聚合物动力学和系链结构影响配体对受体的访问。

  摘要：

  DOI：

  10.1002/anie.200601923
• 作为产物：
  描述：

  炔雌醇 、 对溴苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以76 %的产率得到17α-[(4-formylphenyl)]ethynylestra-1,3,5-(10)triene-3,17β-diol
  参考文献：
  名称：

  一种增强亚硝酰钌络合物细胞摄取的特洛伊木马方法

  摘要：

  亚硝酰钌 (RuNO) 配合物由于几个吸引人的特性而继续引起人们的广泛研究兴趣，这些特性使这些光活化一氧化氮 (NO˙) 供体在光活化化疗中的应用中具有吸引力。已经讨论了能够在水介质中传递细胞毒性浓度的 NO˙ 的候选分子的有趣例子。然而，大多数这些高极性和相对较大的分子是否能被细胞有效地整合的问题在很大程度上仍然没有得到解答。在本文中，我们介绍了用 17α-炔雌醇 (EE) 功能化的 RuNO 复合物的合成及其化学、光物理和光化学表征，17α-炔雌醇 ( EE ) 是一种半合成甾体激素，旨在充当分子特洛伊木马，用于靶向递送 RuNO 复合物。讨论围绕两个主要分子靶点，一个包含EE ( EE-Phtpy-RuNO )，另一个是缺乏该生物识别片段的参考化合物 ( Phtpy-RuNO )。虽然两种复合物在水性介质中表现出相似的光学吸收曲线和 NO˙ 释放效率，但在它们对真皮成纤维细胞的细胞摄

  DOI：

  10.1039/d3dt03480a

文献信息

• Design, synthesis and biological evaluation of novel estrogen-derived steroid metal complexes
  作者：Xinlong Zhang、Ziqing Zuo、Juan Tang、Kai Wang、Caihua Wang、Weiyan Chen、Changhao Li、Wen Xu、Xiaolin Xiong、Kangxiang Yuntai、Jian Huang、Xiaoli Lan、Hai-Bing Zhou

  DOI：10.1016/j.bmcl.2013.04.088

  日期：2013.7

  A new series of estrogen-derived metal complexes were synthesized and characterized. The functionalized estrogen receptor ligands were prepared by a four-step synthetic strategy, and then three transition metal Pd, Ni, Zn were introduced readily to give the title metal complexes, in which the squaramide was introduced as ion acceptor for the first time in the development of estrogen-derived metal complexes for estrogen receptor. Upon binding to estrogen receptors, all of the estrogen conjugates exhibited acceptable binding affinity (up to 4.04% relative to estradiol), and in transcription assays, all the compounds are agonists on ER alpha. Molecular modeling studies suggest a structural basis for the agonist activity of these compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• Steroidal bivalent ligands for the estrogen receptor: Design, synthesis, characterization and binding affinities
  作者：Andrew L. LaFrate、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1016/j.bmc.2009.04.016

  日期：2009.5

  Steroidal bivalent ligands for the estrogen receptor (ER) were designed using crystal structures of ER alpha dimers as a template. The syntheses of several 17 alpha-ethynylestradiol-based bivalent ligands with varying linker compositions and lengths are described. The binding affinities of these bivalent ligands for ERa and ER beta were determined. In the two series of bivalent ligands that we synthesized, there is a clear correlation between linker length and binding affinity, both of which reach a maximum at the same tether length. Further studies are underway to explore aspects of bivalent ligand and control compound binding to the ERs and their effects on ER dimer formation; these results will be reported in a subsequent publication. (C) 2009 Elsevier Ltd. All rights reserved.
• Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens
  作者：Hye-Yeong Kim、Johann Sohn、Gihani T. Wijewickrama、Praneeth Edirisinghe、Teshome Gherezghiher、Madhubani Hemachandra、Pei-Yi Lu、R. Esala Chandrasena、Mary Ellen Molloy、Debra A. Tonetti、Gregory R.J. Thatcher

  DOI：10.1016/j.bmc.2009.11.046

  日期：2010.1

  Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E-2) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E-2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer-E-2 conjugates, CD-E-2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm. (C) 2009 Elsevier Ltd. All rights reserved.