4-Fluoro-3-(O-tert-butyldimethylsilyl)oestrone | 133859-85-5

• 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: 4-Fluoro-3-(O-tert-butyldimethylsilyl)oestrone
• CAS: 133859-85-5
• 化学式: C₂₄H₃₅FO₂Si
• 分子量: 402.625
• InChiKey: IRMKYSBVIMGAJZ-CVJORQDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-Fluoro-3-(O-tert-butyldimethylsilyl)oestrone 在 4-二甲氨基吡啶 、 氢气 、 palladium(II) hydroxide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 3-O-tert-butyldimethylsilyl-4-fluoro-17β-(3'-trifluoromethylbenzenesulfonamido)-estra-1,3,5(10)-trien-3-ol
  参考文献：
  名称：

  A-ring substituted 17β-arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent reversible inhibitors of steroid sulfatase

  摘要：

  Steroid sulfatase (STS) catalyzes the hydrolysis of the sulfate ester group in biologically inactive sulfated steroids to give biologically active steroids. Inhibitors of STS are considered to be potential therapeutics for treating hormone-dependent cancers such as ER+ breast cancer. A series of 4-substituted 17 beta-arylsulfonamides of 17 beta-aminoestra-1,3,5(10)-trien-3-ol were prepared and examined as STS inhibitors. The presence of a NO2 or Br at the 2-position of the A-ring resulted in a decrease in potency compared to their A-ring-unsubstituted counterparts. However the presence of a nitro group or fluorine atom at the 4-position of the A-ring resulted in an increase in potency and one of these compounds exhibited a K-i(app) value of 1 nM. Modeling studies provided insight into how these compounds interact with active site residues. The anti-proliferative activity of the 3'-Br, 3'-CF3, 4-NO2-3'-Br and 4-NO2-3'-CF3 derivatives were examined using the NCI 60-cell-line panel and found to have mean graph midpoint values of 1.9-3.4 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.019
• 作为产物：
  描述：

  2-tert-butylestrone 在 咪唑 、 aluminum (III) chloride 、 三氟甲磺酸N-吡啶鎓 作用下， 以 硝基甲烷 、 二氯甲烷 、 1,1,2-三氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 4-Fluoro-3-(O-tert-butyldimethylsilyl)oestrone
  参考文献：
  名称：

  A-ring substituted 17β-arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent reversible inhibitors of steroid sulfatase

  摘要：

  Steroid sulfatase (STS) catalyzes the hydrolysis of the sulfate ester group in biologically inactive sulfated steroids to give biologically active steroids. Inhibitors of STS are considered to be potential therapeutics for treating hormone-dependent cancers such as ER+ breast cancer. A series of 4-substituted 17 beta-arylsulfonamides of 17 beta-aminoestra-1,3,5(10)-trien-3-ol were prepared and examined as STS inhibitors. The presence of a NO2 or Br at the 2-position of the A-ring resulted in a decrease in potency compared to their A-ring-unsubstituted counterparts. However the presence of a nitro group or fluorine atom at the 4-position of the A-ring resulted in an increase in potency and one of these compounds exhibited a K-i(app) value of 1 nM. Modeling studies provided insight into how these compounds interact with active site residues. The anti-proliferative activity of the 3'-Br, 3'-CF3, 4-NO2-3'-Br and 4-NO2-3'-CF3 derivatives were examined using the NCI 60-cell-line panel and found to have mean graph midpoint values of 1.9-3.4 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.019

文献信息

• Regioselective synthesis of a-ring halogenated derivatives of 17α-ethynyloestradiol
  作者：Philip C. Bulman Page、Fazal Hussain、Nicholas M. Bonham、Paul Morgan、James L. Maggs、B.Kevin Park

  DOI：10.1016/s0040-4020(01)87092-7

  日期：1991.1