4-[3,5-Bis(4-hydroxyphenyl)-1-propylpyrrol-2-yl]-3-fluorophenol | 1403674-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[3,5-Bis(4-hydroxyphenyl)-1-propylpyrrol-2-yl]-3-fluorophenol
• 英文别名: 4-[3,5-bis(4-hydroxyphenyl)-1-propylpyrrol-2-yl]-3-fluorophenol
• CAS: 1403674-87-2
• 化学式: C₂₅H₂₂FNO₃
• 分子量: 403.453
• InChiKey: YYLPTPJOWFJPTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间氟苯甲醚 在 aluminum (III) chloride 、 三溴化硼 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 98.0h， 生成 4-[3,5-Bis(4-hydroxyphenyl)-1-propylpyrrol-2-yl]-3-fluorophenol
  参考文献：
  名称：

  Influence of Chlorine or Fluorine Substitution on the Estrogenic Properties of 1-Alkyl-2,3,5-tris(4-hydroxyphenyl)-1H-pyrroles

  摘要：

  In continuation of Our previous work, several 1- alkyl-2,3,5-tris(4-hydroxyphenyl)aryl-1H-pyrroles with chlor-Me or fluorine substituents in the aryl residues were synthesized and tested for estrogen receptor (ER) binding at isolated ER alpha/ER beta. receptors (HAP assay), and. in trans activation assays using ER alpha-positive MCF-7/2a as well as U2-OS/ER alpha and U2-OS/ER beta cells. In the competition experiment at ER alpha the compounds displayed very high relative binding-affinities of up to 37% (determined for 8m) but with restricted subtype selectivity (e.g., ER alpha/ER beta (8ma) = 9). The highest estrogenic potency in ER alpha-positive MCP-7/2a cells was determined for 2,3,5-tris(2-fluoro-4-hydroxyphenyl)-1-prolayl-1H-pyriole 8m (EC50 = 23 nM), while in U2-OS/ER alpha cells 2-(2-fluoro-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1H propyl-1H pyrrole 8b (EC50 = 0.12 nM) was the Most potent agonist, only 30 fold less active than estradiol (E2, EC50 = 0.004 nM). In U2-OS/ER beta cells for all pyrroles no transactivation could be observed, which indicates that they are selective ER alpha agonists in Cellular systems.

  DOI：

  10.1021/jm300860j

文献信息

• Influence of Chlorine or Fluorine Substitution on the Estrogenic Properties of 1-Alkyl-2,3,5-tris(4-hydroxyphenyl)-1<i>H</i>-pyrroles
  作者：Anja Schäfer、Anja Wellner、Martin Strauss、Andreas Schäfer、Gerhard Wolber、Ronald Gust

  DOI：10.1021/jm300860j

  日期：2012.11.26

  In continuation of Our previous work, several 1- alkyl-2,3,5-tris(4-hydroxyphenyl)aryl-1H-pyrroles with chlor-Me or fluorine substituents in the aryl residues were synthesized and tested for estrogen receptor (ER) binding at isolated ER alpha/ER beta. receptors (HAP assay), and. in trans activation assays using ER alpha-positive MCF-7/2a as well as U2-OS/ER alpha and U2-OS/ER beta cells. In the competition experiment at ER alpha the compounds displayed very high relative binding-affinities of up to 37% (determined for 8m) but with restricted subtype selectivity (e.g., ER alpha/ER beta (8ma) = 9). The highest estrogenic potency in ER alpha-positive MCP-7/2a cells was determined for 2,3,5-tris(2-fluoro-4-hydroxyphenyl)-1-prolayl-1H-pyriole 8m (EC50 = 23 nM), while in U2-OS/ER alpha cells 2-(2-fluoro-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1H propyl-1H pyrrole 8b (EC50 = 0.12 nM) was the Most potent agonist, only 30 fold less active than estradiol (E2, EC50 = 0.004 nM). In U2-OS/ER beta cells for all pyrroles no transactivation could be observed, which indicates that they are selective ER alpha agonists in Cellular systems.