6-methoxy-2-(4-methoxyphenyl)-2H-indazole | 848142-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-methoxy-2-(4-methoxyphenyl)-2H-indazole
• 英文别名: 6-Methoxy-2-(4-methoxyphenyl)indazole
• CAS: 848142-49-4
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: WVPKHIURRINHAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  304.1±34.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：

  6-methoxy-2-(4-methoxyphenyl)-2H-indazole 在 溴 、 溶剂黄146 作用下， 反应 12.0h， 以85%的产率得到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
• 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 、 sodium hexamethyldisilazane 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.25h， 生成 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

文献信息

• Assembly of Fully Substituted 2<i>H</i> -Indazoles Catalyzed by Cu₂ O Rhombic Dodecahedra and Evaluation of Anticancer Activity
  作者：Rajeeva Lochana Panchangam、Venkatraman Manickam、Kaushik Chanda

  DOI：10.1002/cmdc.201800707

  日期：2019.1.22

  methods for one-pot transformations are highly challenging in synthetic organic chemistry. In this study, the Cu2 O rhombic dodecahedra-catalyzed synthesis of 2H-indazoles is demonstrated with good to excellent yields from readily available chemicals. This one-pot procedure involves Cu2 O nanoparticle-catalyzed consecutive C-N, and N-N bond formation followed by cyclization to yield 2H-indazoles with

  一锅转化的同时形成CN和NN键的方法在合成有机化学中极具挑战性。在这项研究中，证明了Cu2 O菱形十二面体催化的2H-吲唑合成具有良好或极好的得自易得化学品的产率。此一锅法涉及Cu2 O纳米粒子催化的连续CN和NN键的形成，然后环化生成具有宽底物范围和高官能团耐受性的2H-吲唑。各种基于细胞的生物测定研究表明，2H-吲唑通常通过剂量依赖性方式诱导凋亡来抑制癌细胞的生长。此外，在MDA-MB-468细胞系中测试的2H-吲唑能够抑制癌细胞的迁移和侵袭。因此，
• Indazole Estrogens:  Highly Selective Ligands for the Estrogen Receptor β
  作者：Meri De Angelis、Fabio Stossi、Kathryn A. Carlson、Benita S. Katzenellenbogen、John A. Katzenellenbogen

  DOI：10.1021/jm049223g

  日期：2005.2.1

  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.