3-(3-苯基甲氧基苯基)苯酚 | 889950-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3-苯基甲氧基苯基)苯酚
• 英文名称: 3′-(benzyloxy)-[1,1′-biphenyl]-3-ol
• 英文别名: 3-(3-Benzyloxyphenyl)phenol；3-(3-phenylmethoxyphenyl)phenol
• CAS: 889950-90-7
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: ZAKREHXBTVSZAW-UHFFFAOYSA-N

物化性质

• 沸点：
  466.6±33.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  3-(3-苯基甲氧基苯基)苯酚 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 3′-hydroxy-[1,1′-biphenyl]-3-yl N-{6-[3-((2-acetamidoethyl)methylamino)phenoxy]hexyl} carbamate
  参考文献：
  名称：

  Identification of Bivalent Ligands with Melatonin Receptor Agonist and Fatty Acid Amide Hydrolase (FAAH) Inhibitory Activity That Exhibit Ocular Hypotensive Effect in the Rabbit

  摘要：

  Activation of melatonin receptors and inhibition of fatty acid amide hydrolase (FAAH) have both shown potential benefits for the treatment of glaucoma. To exploit the combination of these biological activities in single therapeutic agents, we designed dual-acting compounds sharing the pharmacophore elements required for the two targets, in search for balanced potencies as MT1/MT2 agonists and FAAH inhibitors. In particular, the N-anilinoethylamide scaffold, previously developed for melatonergic ligands, was decorated at meta position with a polymethylene linker bound to an O-arylcarbamate group, substituted according to known structure-activity relationships for FAAH inhibition. For the most active series, the N-anilinoethylamide portion was also replaced with the indole scaffold of melatonin. O-Biphenyl-3-ylcarbamate characterized by remarkable and balanced activity at both targets, in the nanomolar range for compound 29. Topical administration reduced elevated intraocular pressure in rabbits, with a longer action and improved efficacy compared to the reference compounds melatonin and URB597.

  DOI：

  10.1021/acs.jmedchem.8b00893
• 作为产物：
  描述：

  间溴苯酚 、 3-苄氧基苯硼酸 在 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.67h， 以81%的产率得到3-(3-苯基甲氧基苯基)苯酚
  参考文献：
  名称：

  Identification of Bivalent Ligands with Melatonin Receptor Agonist and Fatty Acid Amide Hydrolase (FAAH) Inhibitory Activity That Exhibit Ocular Hypotensive Effect in the Rabbit

  摘要：

  Activation of melatonin receptors and inhibition of fatty acid amide hydrolase (FAAH) have both shown potential benefits for the treatment of glaucoma. To exploit the combination of these biological activities in single therapeutic agents, we designed dual-acting compounds sharing the pharmacophore elements required for the two targets, in search for balanced potencies as MT1/MT2 agonists and FAAH inhibitors. In particular, the N-anilinoethylamide scaffold, previously developed for melatonergic ligands, was decorated at meta position with a polymethylene linker bound to an O-arylcarbamate group, substituted according to known structure-activity relationships for FAAH inhibition. For the most active series, the N-anilinoethylamide portion was also replaced with the indole scaffold of melatonin. O-Biphenyl-3-ylcarbamate characterized by remarkable and balanced activity at both targets, in the nanomolar range for compound 29. Topical administration reduced elevated intraocular pressure in rabbits, with a longer action and improved efficacy compared to the reference compounds melatonin and URB597.

  DOI：

  10.1021/acs.jmedchem.8b00893

文献信息

• Identification of Bivalent Ligands with Melatonin Receptor Agonist and Fatty Acid Amide Hydrolase (FAAH) Inhibitory Activity That Exhibit Ocular Hypotensive Effect in the Rabbit
  作者：Gilberto Spadoni、Annalida Bedini、Lucia Furiassi、Michele Mari、Marco Mor、Laura Scalvini、Alessio Lodola、Andrea Ghidini、Valeria Lucini、Silvana Dugnani、Francesco Scaglione、Daniele Piomelli、Kwang-Mook Jung、Claudiu T. Supuran、Laura Lucarini、Mariaconcetta Durante、Silvia Sgambellone、Emanuela Masini、Silvia Rivara

  DOI：10.1021/acs.jmedchem.8b00893

  日期：2018.9.13

  Activation of melatonin receptors and inhibition of fatty acid amide hydrolase (FAAH) have both shown potential benefits for the treatment of glaucoma. To exploit the combination of these biological activities in single therapeutic agents, we designed dual-acting compounds sharing the pharmacophore elements required for the two targets, in search for balanced potencies as MT1/MT2 agonists and FAAH inhibitors. In particular, the N-anilinoethylamide scaffold, previously developed for melatonergic ligands, was decorated at meta position with a polymethylene linker bound to an O-arylcarbamate group, substituted according to known structure-activity relationships for FAAH inhibition. For the most active series, the N-anilinoethylamide portion was also replaced with the indole scaffold of melatonin. O-Biphenyl-3-ylcarbamate characterized by remarkable and balanced activity at both targets, in the nanomolar range for compound 29. Topical administration reduced elevated intraocular pressure in rabbits, with a longer action and improved efficacy compared to the reference compounds melatonin and URB597.