3-bromo-5-methoxy-2-(4-methoxyphenyl)-2H-indazole | 848142-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-bromo-5-methoxy-2-(4-methoxyphenyl)-2H-indazole
• 英文别名: 3-bromo-5-methoxy-2-(4-methoxyphenyl)indazole
• CAS: 848142-58-5
• 化学式: C₁₅H₁₃BrN₂O₂
• 分子量: 333.184
• InChiKey: XYKQSOBARBHUIN-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  334.9±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)：
  4.2
• 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：

  3-bromo-5-methoxy-2-(4-methoxyphenyl)-2H-indazole 在 palladium dihydroxide tris(dibenzylideneacetone)dipalladium (0) 、 三叔丁基膦 、 氢气 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 5-methoxy-2-(4-methoxyphenyl)-3-ethyl-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
• 作为产物：
  描述：

  4-甲氧基苯肼盐酸盐 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 3-bromo-5-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

文献信息

• [EN] ESTROGEN RECEPTOR BETA LIGANDS FOR THE PREVENTION AND TREATMENT OF MULTIPLE SCLEROSIS (MS) AND OTHER DEMYELINATING, INFLAMMATORY AND NEURODEGENERATIVE DISEASES<br/>[FR] LIGANDS BÊTA DU RÉCEPTEUR DES ŒSTROGÈNES POUR LA PRÉVENTION ET LE TRAITEMENT DE LA SCLÉROSE EN PLAQUES (SP) ET D'AUTRES MALADIES DÉMYÉLINISANTES, INFLAMMATOIRES ET NEURODÉGÉNÉRATIVES
  申请人：UNIV ILLINOIS

  公开号：WO2019226936A1

  公开（公告）日：2019-11-28

  4-Hydroxyphenyl-2H-indazol-5-ol compounds are estrogen receptor beta ligands that have immunomodulatory properties and increase oligodendrocyte survival, differentiation, and remyelination. The compounds, compositions, and kits are useful in the treatment of multiple sclerosis and endometriosis.

  4-羟基苯基-2H-吲哚-5-醇化合物是雌激素受体β配体，具有免疫调节特性，并增加少突胶质细胞的存活、分化和重髓鞘生成。这些化合物、组合物和试剂盒在治疗多发性硬化症和子宫内膜异位症方面具有用途。