2-(4-hydroxyphenyl)-N-methyl-N-phenethylacetamide | 950832-96-9

• 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-(4-hydroxyphenyl)-N-methyl-N-phenethylacetamide
• 英文别名: 2-(4-hydroxyphenyl)-N-methyl-N-(2-phenylethyl)acetamide
• CAS: 950832-96-9
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: DCWKVZJZWJVKDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯乙基对甲苯基砜 、 2-(4-hydroxyphenyl)-N-methyl-N-phenethylacetamide 在 18-冠醚-6 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 以89%的产率得到2-[4-(2-chloroethoxy)phenyl]-N-methyl-N-phenethylacetamide
  参考文献：
  名称：

  芳基链烷酸的抗白三烯苯乙基氨基衍生物治疗溃疡性结肠炎

  摘要：

  制备了一系列带有甲基（苯乙基）氨基的芳基链烷酸衍生物，并评估了它们对LTB 4生物合成的抑制作用。回归分析表明，该活性对α-甲基和α-未取代的链烷酸衍生物的亲脂性的抛物线依赖性略有不同。由α-未取代的链烷酸得到的关系被先前制备的类似的芳族丙烯酸衍生物组所扩展，而回归系数和统计标准没有任何变化。结论是，活性最高的化合物属于2-芳基丙酸衍生物，其亲脂性接近log  P opt（= 6.97）。但一般而言，与先前制备的一系列衍生物IV相比，所研究化合物酸性部分的结构变化并未产生LTB 4生物合成抑制作用的实质性改善。在三种炎症动物模型中评估了所研究化合物的抗炎作用，并跟踪了它们在溃疡性结肠炎（UC）治疗中的可能用途。从12种评估的化合物中，有4种化合物比标准的柳氮磺胺吡啶在UC抑制中的活性更高，但是可以说，与以前的芳环酸酯衍生物相比，芳环和羧基之间的连接链的变化并没有显着改善该活性。酸。LTB之

  DOI：

  10.1016/j.ejmech.2008.02.030
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-N-methyl-N-phenethylacetamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到2-(4-hydroxyphenyl)-N-methyl-N-phenethylacetamide
  参考文献：
  名称：

  Antileukotrienic N-arylethyl-2-arylacetamides in the treatment of ulcerative colitis

  摘要：

  A series of arylacetic acid derivatives bearing methyl(aryiethyl)amino groups were prepared and their antileukotrienic activities involving LTB4 were evaluated. Regression analysis has shown a strong dependence of these activities on lipophilicity for both LTB4 receptor binding and inhibition of LTB4 biosynthesis; parabolic relationships were derived. The values of slopes of the ascending linear parts of these dependences indicate various types of hydrophobic binding at the site of ligand interaction with relevant biomacromolecules. The anti-inflammatory effect of the compounds under study was also evaluated in three animal models of inflammation and their possible utilization in the treatment of ulcerative colitis (UC) was followed. The importance of antileukotrienic activities for the anti-inflammatory effect, especially in the model of UC was discussed, but further experiments are necessary to confirm the respective relations. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.01.014

文献信息

• Antileukotrienic phenethylamido derivatives of arylalkanoic acids in the treatment of ulcerative colitis
  作者：Richard Junek、Miloslav Kverka、Antonín Jandera、Vladimíra Panajotová、Dalibor Šatinský、Miloš Macháček、Miroslav Kuchař

  DOI：10.1016/j.ejmech.2008.02.030

  日期：2009.1

  connecting chain between aromatic ring and carboxyl did not bring about the important improvement of this activity in comparison with previous derivatives of arylacetic acids. Possible relation between LTB4 biosynthesis inhibition and ulcerative colitis is seriously broken by the compound 8a with carbonyl as the additional functional group on the connecting chain between carboxyl and aromatic ring.

  制备了一系列带有甲基（苯乙基）氨基的芳基链烷酸衍生物，并评估了它们对LTB 4生物合成的抑制作用。回归分析表明，该活性对α-甲基和α-未取代的链烷酸衍生物的亲脂性的抛物线依赖性略有不同。由α-未取代的链烷酸得到的关系被先前制备的类似的芳族丙烯酸衍生物组所扩展，而回归系数和统计标准没有任何变化。结论是，活性最高的化合物属于2-芳基丙酸衍生物，其亲脂性接近log  P opt（= 6.97）。但一般而言，与先前制备的一系列衍生物IV相比，所研究化合物酸性部分的结构变化并未产生LTB 4生物合成抑制作用的实质性改善。在三种炎症动物模型中评估了所研究化合物的抗炎作用，并跟踪了它们在溃疡性结肠炎（UC）治疗中的可能用途。从12种评估的化合物中，有4种化合物比标准的柳氮磺胺吡啶在UC抑制中的活性更高，但是可以说，与以前的芳环酸酯衍生物相比，芳环和羧基之间的连接链的变化并没有显着改善该活性。酸。LTB之
• Antileukotrienic N-arylethyl-2-arylacetamides in the treatment of ulcerative colitis
  作者：Richard Junek、Bohumila Brůnová、Miloslav Kverka、Vladimíra Panajotová、Antonín Jandera、Miroslav Kuchař

  DOI：10.1016/j.ejmech.2007.01.014

  日期：2007.8

  A series of arylacetic acid derivatives bearing methyl(aryiethyl)amino groups were prepared and their antileukotrienic activities involving LTB4 were evaluated. Regression analysis has shown a strong dependence of these activities on lipophilicity for both LTB4 receptor binding and inhibition of LTB4 biosynthesis; parabolic relationships were derived. The values of slopes of the ascending linear parts of these dependences indicate various types of hydrophobic binding at the site of ligand interaction with relevant biomacromolecules. The anti-inflammatory effect of the compounds under study was also evaluated in three animal models of inflammation and their possible utilization in the treatment of ulcerative colitis (UC) was followed. The importance of antileukotrienic activities for the anti-inflammatory effect, especially in the model of UC was discussed, but further experiments are necessary to confirm the respective relations. (c) 2007 Elsevier Masson SAS. All rights reserved.