(8R,9S,13S,14S,17R)-17-((E)-2,6-dimethylstyryl)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate | 1380442-25-0

• 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: (8R,9S,13S,14S,17R)-17-((E)-2,6-dimethylstyryl)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate
• CAS: 1380442-25-0
• 化学式: C₃₀H₃₆O₃
• 分子量: 444.614
• InChiKey: WCULDNJZEKRKBG-RDORYVLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17R)-17-((E)-2,6-dimethylstyryl)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate 在 甲醇 、 sodium hydroxide 作用下， 以52%的产率得到(17α,20E)-21-[2,6-dimethylphenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol
  参考文献：
  名称：

  Synthesis and evaluation of 17α-(dimethylphenyl)vinyl estradiols as probes of the estrogen receptor-α ligand binding domain

  摘要：

  As part of our program to explore the influence of small structural modifications on the biological response of the estrogen receptor-alpha (ER alpha), we prepared and evaluated a series of mono-and di-substituted phenyl vinyl estradiols. The target compounds were prepared in 45-80% yields using the Stille coupling reaction and evaluated using competitive binding analysis with the ER alpha-ligand binding domain (hER alpha-LBD) and estrogenic activity (induction of alkaline phosphatase in Ishikawa cells). Results indicated that the 2,4- and 2,5-dimethyl derivatives, 5b and 5c, had the highest relative binding affinity (RBA = 20.5 and 37.3%) and relative stimulatory activity (RSA = 101.0% and 12.3%) of the di-methyl series. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.01.003
• 作为产物：
  描述：

  1,3-二甲基-2-碘苯 、 乙炔基雌二醇3-乙酸酯 在 三乙基硼 、 三正丁基氢锡 、 四(三苯基膦)钯 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 以52%的产率得到(8R,9S,13S,14S,17R)-17-((E)-2,6-dimethylstyryl)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate
  参考文献：
  名称：

  Synthesis and evaluation of 17α-(dimethylphenyl)vinyl estradiols as probes of the estrogen receptor-α ligand binding domain

  摘要：

  As part of our program to explore the influence of small structural modifications on the biological response of the estrogen receptor-alpha (ER alpha), we prepared and evaluated a series of mono-and di-substituted phenyl vinyl estradiols. The target compounds were prepared in 45-80% yields using the Stille coupling reaction and evaluated using competitive binding analysis with the ER alpha-ligand binding domain (hER alpha-LBD) and estrogenic activity (induction of alkaline phosphatase in Ishikawa cells). Results indicated that the 2,4- and 2,5-dimethyl derivatives, 5b and 5c, had the highest relative binding affinity (RBA = 20.5 and 37.3%) and relative stimulatory activity (RSA = 101.0% and 12.3%) of the di-methyl series. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.01.003