Methyl 5-[2-[methyl(2-phenylethyl)amino]-2-oxoethyl]-2-phenylbenzoate | 181268-52-0

• 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: Methyl 5-[2-[methyl(2-phenylethyl)amino]-2-oxoethyl]-2-phenylbenzoate
• CAS: 181268-52-0
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: YLWQYXBYELVQEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 5-[2-[methyl(2-phenylethyl)amino]-2-oxoethyl]-2-phenylbenzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以59%的产率得到4-[(Methyl-phenethyl-carbamoyl)-methyl]-biphenyl-2-carboxylic acid
  参考文献：
  名称：

  A Novel Series of [2-[Methyl(2-phenethyl)amino]-2-oxoethyl]benzene-Containing Leukotriene B₄ Antagonists:  Initial Structure−Activity Relationships

  摘要：

  This report describes the synthesis of a new class of LTB(4) receptor antagonists containing [2-[methyl(2-phenethyl)amino]-2-oxoethyl]benzene as a key binding domain for interaction with high-affinity LTB(4) receptors. In addition to this binding domain, two other structural features, an acid function and a lipophilic group, are also required by these compounds for high binding affinity, Our studies indicate that maximal binding affinity in this series is controlled by the spatial relationship of these groups relative to one another, The structure-activity relationships are discussed, The most potent compound in this chemical series, (E)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (32), has an IC50 of 2 nM in a guinea pig spleen cell membrane assay, In the whale-cell human neutrophils binding assay, (Z)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (30) was the most potent compound with an IC50 of 50 nM.

  DOI：

  10.1021/jm9506985
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲酸甲酯 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 硫酸 、 氢溴酸 、 双氧水 、 potassium carbonate 、 溶剂黄146 、 lithium chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 99.5h， 生成 Methyl 5-[2-[methyl(2-phenylethyl)amino]-2-oxoethyl]-2-phenylbenzoate
  参考文献：
  名称：

  A Novel Series of [2-[Methyl(2-phenethyl)amino]-2-oxoethyl]benzene-Containing Leukotriene B₄ Antagonists:  Initial Structure−Activity Relationships

  摘要：

  This report describes the synthesis of a new class of LTB(4) receptor antagonists containing [2-[methyl(2-phenethyl)amino]-2-oxoethyl]benzene as a key binding domain for interaction with high-affinity LTB(4) receptors. In addition to this binding domain, two other structural features, an acid function and a lipophilic group, are also required by these compounds for high binding affinity, Our studies indicate that maximal binding affinity in this series is controlled by the spatial relationship of these groups relative to one another, The structure-activity relationships are discussed, The most potent compound in this chemical series, (E)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (32), has an IC50 of 2 nM in a guinea pig spleen cell membrane assay, In the whale-cell human neutrophils binding assay, (Z)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (30) was the most potent compound with an IC50 of 50 nM.

  DOI：

  10.1021/jm9506985