3-(5-bromo-2-methoxyphenyl)-1-phenyl-1H-pyrazole | 1360444-98-9

• 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-(5-bromo-2-methoxyphenyl)-1-phenyl-1H-pyrazole
• 英文别名: 3-(5-Bromo-2-methoxyphenyl)-1-phenylpyrazole
• CAS: 1360444-98-9
• 化学式: C₁₆H₁₃BrN₂O
• 分子量: 329.196
• InChiKey: ITKXCDSZDOEVBK-UHFFFAOYSA-N

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：
  0.06
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-methoxyphenyl)-1-phenyl-1H-pyrazole 在 四(三苯基膦)钯 、 三氟二甲基硫醚络合物 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 34.67h， 生成 5-allyl-3'-(1-phenyl-1H-pyrazol-3-yl)-[1,1'-biphenyl]-2,4'-diol
  参考文献：
  名称：

  Synthesis and neurite growth evaluation of new analogues of honokiol, a neolignan with potent neurotrophic activity

  摘要：

  A versatile synthetic route is reported towards the preparation of new analogues for potent neurotrophic agent biaryl-type lignan honokiol. A focused 24-membered library of derivatives containing five different groups at 5'-position of honokiol has been prepared in fair to good overall yields. Compared to the natural product, or to analogues with a short alkyl chain in this position, these new derivatives have lost most of the neurotrophic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.015
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 Jones reagent 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 8.5h， 生成 3-(5-bromo-2-methoxyphenyl)-1-phenyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis and neurite growth evaluation of new analogues of honokiol, a neolignan with potent neurotrophic activity

  摘要：

  A versatile synthetic route is reported towards the preparation of new analogues for potent neurotrophic agent biaryl-type lignan honokiol. A focused 24-membered library of derivatives containing five different groups at 5'-position of honokiol has been prepared in fair to good overall yields. Compared to the natural product, or to analogues with a short alkyl chain in this position, these new derivatives have lost most of the neurotrophic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.015

文献信息

• Synthesis and anti-neuroinflammatory activity of N-heterocyclic analogs based on natural biphenyl-neolignan honokiol
  作者：Yue Yuan、Lalita Subedi、Daesung Lim、Jae-Kyung Jung、Sun Yeou Kim、Seung-Yong Seo

  DOI：10.1016/j.bmcl.2018.11.014

  日期：2019.1

  Novel isoxazole and pyrazole analogs based on natural biphenyl-neolignan honokiol were synthesized and evaluated for their inhibitory activities against nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells. The isoxazole skeleton was constructed via nitrile oxide cycloaddition from oxime 3 and pyrazole was generated by condensation of 4-chromone and alkylhydrazine. Among the analogs, 13b and 14a showed stronger inhibitory activities with IC50 values of 8.9 and 1.2 mu M, respectively, than honokiol.