(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5-[[4-[(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]triazol-1-yl]methyl]-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol | 1215455-31-4

• 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: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5-[[4-[(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]triazol-1-yl]methyl]-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• CAS: 1215455-31-4
• 化学式: C₆₂H₉₃N₃O₃₆
• 分子量: 1456.42
• InChiKey: CFNMQQBDOSHKJA-WGCBWCQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.6
• 重原子数：
  101
• 可旋转键数：
  9
• 环数：
  26.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  605
• 氢给体数：
  22
• 氢受体数：
  38

反应信息

• 作为产物：
  描述：

  炔雌醇 、 6A-叠氮基-6A-脱氧-β-环糊精 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以64%的产率得到(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5-[[4-[(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]triazol-1-yl]methyl]-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
  参考文献：
  名称：

  Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.046

文献信息

• 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.