2-[2-(2,6-dichloro-3-methoxy-4-phenylmethoxyanilino)phenyl]-N,N-dimethylacetamide | 131663-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[2-(2,6-dichloro-3-methoxy-4-phenylmethoxyanilino)phenyl]-N,N-dimethylacetamide
• CAS: 131663-36-0
• 化学式: C₂₄H₂₄Cl₂N₂O₃
• 分子量: 459.372
• InChiKey: JEKSTWXYIZBZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(2,6-dichloro-3-methoxy-4-phenylmethoxyanilino)phenyl]-N,N-dimethylacetamide 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 10.42h， 生成 2-[(2,6-二氯-3-甲氧基-4-羟基苯基)氨基]苯乙酸
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.

  DOI：

  10.1021/jm00171a008
• 作为产物：
  描述：

  2-(2-碘苯基)-N,N-二甲基乙酰胺 、 2,6-Dichloro-3-methoxy-4-phenylmethoxyaniline 在 copper(l) iodide 、 铜 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 100.0h， 生成 2-[2-(2,6-dichloro-3-methoxy-4-phenylmethoxyanilino)phenyl]-N,N-dimethylacetamide
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.

  DOI：

  10.1021/jm00171a008

文献信息

• Cyclooxygenase- und 5-Lipoxygenase-inhibierende Hydroxansäurederivate
  申请人：CIBA-GEIGY AG

  公开号：EP0377896A2

  公开（公告）日：1990-07-18

  Verbindungen der Formel worin Ar₁ einen unsubstituierten oder substituierten Arylrest bedeutet, Ar₂ einen unsubstituierten oder substituierten Arylenrest bedeutet, R₁ Wasserstoff oder einen aliphatischen oder araliphatischen Rest bedeutet, R₂ einen aliphatischen oder araliphatischen Rest bedeutet, R₃ Wasser­stoff, Niederalkyl oder Niederalkanoyl darstellt und Z einen zweiwerti­gen aliphatischen Rest bedeutet, und ihre Salze sind in an sich bekannter Weise herstellbar. Die verbindungen erweisen sich als duale Hemmer von Cyclooxygenase und S-Lipoxygenase. Sie können als Antiinflammatorikum und/oder als antiallergikum verwendet werden.

  式中的化合物 其中 Ar₁ 是未取代或取代的芳基，Ar₂ 是未取代或取代的芳烯基，R₁ 是氢或脂肪族或脂肪族基，R₂ 是脂肪族或脂肪族基，R₃ 是氢、低级烷基或低级烷酰基，Z 是二价脂肪族基。这些化合物被证明是环氧化酶和 S-脂氧合酶的双重抑制剂。它们可用作消炎药和/或抗过敏药。
• Synthesis and quantitative structure-activity relationships of diclofenac analogs
  作者：Peter Moser、Alfred Sallmann、Irmgard Wiesenberg

  DOI：10.1021/jm00171a008

  日期：1990.9

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.