4-[5-Hydroxy-2-(4-hydroxy-phenyl)-3H-inden-1-yl]-benzoic acid | 866021-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-[5-Hydroxy-2-(4-hydroxy-phenyl)-3H-inden-1-yl]-benzoic acid
• 英文别名: 4-[5-hydroxy-2-(4-hydroxyphenyl)-3H-inden-1-yl]benzoic acid
• CAS: 866021-24-1
• 化学式: C₂₂H₁₆O₄
• 分子量: 344.367
• InChiKey: KERRBGPWKXNBGD-UHFFFAOYSA-N

物化性质

• 沸点：
  581.0±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[5-Hydroxy-2-(4-hydroxy-phenyl)-3H-inden-1-yl]-benzoic acid 、 甲醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以19%的产率得到methyl 4-(6-hydroxy-2-(4-hydroxyphenyl)-1H-inden-3-yl)benzoate
  参考文献：
  名称：

  Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands

  摘要：

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.

  DOI：

  10.1021/jm050226i
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-5-methoxy-1-indanone 在 2,6-二甲基吡啶 、 triethylamine trihydrofluoride 、 1,3-双(二苯基膦)丙烷 、 碘 、 palladium diacetate 、 三溴化硼 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.33h， 生成 4-[5-Hydroxy-2-(4-hydroxy-phenyl)-3H-inden-1-yl]-benzoic acid
  参考文献：
  名称：

  Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands

  摘要：

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.

  DOI：

  10.1021/jm050226i