3-[3-[2-[Methyl(2-phenylethyl)amino]-2-oxoethyl]-5-phenylmethoxyphenyl]but-2-enoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[3-[2-[Methyl(2-phenylethyl)amino]-2-oxoethyl]-5-phenylmethoxyphenyl]but-2-enoic acid
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: OZIZIDNVWOMCNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二苄氧基苯乙酮 在 chromium(VI) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 lithium hydroxide 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 硫酸 、 氢溴酸 、 双氧水 、 sodium hydride 、 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 191.0h， 生成 3-[3-[2-[Methyl(2-phenylethyl)amino]-2-oxoethyl]-5-phenylmethoxyphenyl]but-2-enoic 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

文献信息

• A Novel Series of [2-[Methyl(2-phenethyl)amino]-2-oxoethyl]benzene-Containing Leukotriene B₄ Antagonists:  Initial Structure−Activity Relationships
  作者：Fu-Chih Huang、Wan-Kit Chan、Kevin J. Moriarty、Gregory Poli、Matthew M. Morrissette、Robert A. Galemmo、James D. Warus、William P. Dankulich、Charles A. Sutherland

  DOI：10.1021/jm9506985

  日期：1996.1.1

  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.