2-methoxy-5-(phenylazo)biphenyl | 79380-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-methoxy-5-(phenylazo)biphenyl
• 英文别名: (6-methoxy-biphenyl-3-yl)-phenyl-diazene；(6-Methoxy-biphenyl-3-yl)-phenyl-diazen；5-Phenylazo-2-methoxy-biphenyl；4-Methoxy-3-phenyl-azobenzol
• CAS: 79380-81-7
• 化学式: C₁₉H₁₆N₂O
• 分子量: 288.349
• InChiKey: NEFYHIPWYPVKMP-QZQOTICOSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  439.7±33.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.95
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-(phenylazo)biphenyl 在 palladium on activated charcoal 硫酸 、 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 6-methoxy-[1,1'-biphenyl]-3-ol
  参考文献：
  名称：

  2,3-Dihydrobenzofuran-2-ones: a new class of highly potent antiinflammatory agents

  摘要：

  A series of 2,3-dihydrobenzofuran-2-one analogues of the mold metabolite wortmannin, which is a powerful antiinflammatory compound, was synthesized. Most of these compounds were tested for their ability to inhibit the carrageenin paw edema and the adjuvant-induced arthritis of the rat and for their ability to inhibit prostaglandin synthesis in vitro. Indomethacin and diclofenac were used as references. The results show that compounds bearing an alkyl or aryl group in position 6 and an additional substituent, preferably chlorine, in position 5 are very powerful antiinflammatory agents and inhibitors of prostaglandin synthesis. The most active among these compounds, 5-chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one, was significantly more potent than diclofenac in all testing models, more powerful than indomethacin in inhibiting acute inflammation and prostaglandin synthesis, and somewhat less potent than the latter compound in the adjuvant arthritis model.

  DOI：

  10.1021/jm00144a019
• 作为产物：
  描述：

  sodium 2-biphenylate 在 盐酸 、 sodium hydride 、 sodium nitrite 作用下， 反应 2.0h， 生成 2-methoxy-5-(phenylazo)biphenyl
  参考文献：
  名称：

  2,3-Dihydrobenzofuran-2-ones: a new class of highly potent antiinflammatory agents

  摘要：

  A series of 2,3-dihydrobenzofuran-2-one analogues of the mold metabolite wortmannin, which is a powerful antiinflammatory compound, was synthesized. Most of these compounds were tested for their ability to inhibit the carrageenin paw edema and the adjuvant-induced arthritis of the rat and for their ability to inhibit prostaglandin synthesis in vitro. Indomethacin and diclofenac were used as references. The results show that compounds bearing an alkyl or aryl group in position 6 and an additional substituent, preferably chlorine, in position 5 are very powerful antiinflammatory agents and inhibitors of prostaglandin synthesis. The most active among these compounds, 5-chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one, was significantly more potent than diclofenac in all testing models, more powerful than indomethacin in inhibiting acute inflammation and prostaglandin synthesis, and somewhat less potent than the latter compound in the adjuvant arthritis model.

  DOI：

  10.1021/jm00144a019

文献信息

• Synthesis of 8-(3-Diethylaminopropylamino)-6-methoxy-5-phenylquinoline¹
  作者：H. R. Snyder、Nelson R. Easton

  DOI：10.1021/ja01212a047

  日期：1946.8
• 2,3-Dihydrobenzofuran-2-ones: a new class of highly potent antiinflammatory agents
  作者：Annemarie Closse、Walter Haefliger、Daniel Hauser、Hans Ulrich Gubler、Beatrice Dewald、Marco Baggiolini

  DOI：10.1021/jm00144a019

  日期：1981.12

  A series of 2,3-dihydrobenzofuran-2-one analogues of the mold metabolite wortmannin, which is a powerful antiinflammatory compound, was synthesized. Most of these compounds were tested for their ability to inhibit the carrageenin paw edema and the adjuvant-induced arthritis of the rat and for their ability to inhibit prostaglandin synthesis in vitro. Indomethacin and diclofenac were used as references. The results show that compounds bearing an alkyl or aryl group in position 6 and an additional substituent, preferably chlorine, in position 5 are very powerful antiinflammatory agents and inhibitors of prostaglandin synthesis. The most active among these compounds, 5-chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one, was significantly more potent than diclofenac in all testing models, more powerful than indomethacin in inhibiting acute inflammation and prostaglandin synthesis, and somewhat less potent than the latter compound in the adjuvant arthritis model.