7-bromo-6-methoxy-2-(4-methoxyphenyl)-2H-indazole | 848142-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-bromo-6-methoxy-2-(4-methoxyphenyl)-2H-indazole
• 英文别名: 7-Bromo-6-methoxy-2-(4-methoxyphenyl)indazole
• CAS: 848142-83-6
• 化学式: C₁₅H₁₃BrN₂O₂
• 分子量: 333.184
• InChiKey: OIHKZTCQXNCSFH-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  329.5±34.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-bromo-6-methoxy-2-(4-methoxyphenyl)-2H-indazole 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以63%的产率得到7-Bromo-2-(4-hydroxy-phenyl)-2H-indazol-6-ol
  参考文献：
  名称：

  Indazole Estrogens:  Highly Selective Ligands for the Estrogen Receptor β

  摘要：

  The estrogen receptors, ERalpha and ERbeta, are important pharmaceutical targets. To develop ERbeta-selective ligands, we synthesized a series of nonsteroidal compounds having a phenyl-2H-indazole core with different groups at C-3. Several of these show high affinity and good ERbeta selectivity, especially those with polar and/or polarizable substituents at this site (halogen, CF3, nitrile); the best compounds have affinities for ERbeta comparable to estradiol, with ERbeta affinity selectivity > 100. This potency and ERbeta selectivity is also seen in cell-based transcriptional assays, where several compounds showed ERbeta efficacies equivalent to that of estradiol with ERbeta potency selectivities of 100. These compounds might prove useful as selective pharmacological probes to study the biological actions of estrogens mediated through ERP, and they might lead to the development of useful pharmaceuticals. These findings also contribute to an evolving pharmacophore that characterizes certain nonsteroidal ligands having high ERbeta subtype affinity and potency selectivity.

  DOI：

  10.1021/jm049223g
• 作为产物：
  描述：

  2-溴-4-甲氧基溴苄 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 溴 、 sodium hexamethyldisilazane 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 29.25h， 生成 7-bromo-6-methoxy-2-(4-methoxyphenyl)-2H-indazole
  参考文献：
  名称：

  Indazole Estrogens:  Highly Selective Ligands for the Estrogen Receptor β

  摘要：

  The estrogen receptors, ERalpha and ERbeta, are important pharmaceutical targets. To develop ERbeta-selective ligands, we synthesized a series of nonsteroidal compounds having a phenyl-2H-indazole core with different groups at C-3. Several of these show high affinity and good ERbeta selectivity, especially those with polar and/or polarizable substituents at this site (halogen, CF3, nitrile); the best compounds have affinities for ERbeta comparable to estradiol, with ERbeta affinity selectivity > 100. This potency and ERbeta selectivity is also seen in cell-based transcriptional assays, where several compounds showed ERbeta efficacies equivalent to that of estradiol with ERbeta potency selectivities of 100. These compounds might prove useful as selective pharmacological probes to study the biological actions of estrogens mediated through ERP, and they might lead to the development of useful pharmaceuticals. These findings also contribute to an evolving pharmacophore that characterizes certain nonsteroidal ligands having high ERbeta subtype affinity and potency selectivity.

  DOI：

  10.1021/jm049223g