cis-3-Carboxyvinyl-4-benzyloxyphenylacetic acid | 142588-44-1

• 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: cis-3-Carboxyvinyl-4-benzyloxyphenylacetic acid
• 英文别名: (Z)-3-[5-(carboxymethyl)-2-phenylmethoxyphenyl]prop-2-enoic acid
• CAS: 142588-44-1
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: DZODDPWUFIZPJI-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-3-Carboxyvinyl-4-benzyloxyphenylacetic acid 在 盐酸 、 lithium hydroxide 、 碘 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 35.33h， 生成 trans-N-methyl-N-phenethyl-2-[4-benzyloxy-3-(2carbomethoxyvinyl)phenyl]acetamide
  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：

  溴甲苯 、 (Z)-3-[5-(carboxymethyl)-2-hydroxyphenyl]prop-2-enoic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 cis-3-Carboxyvinyl-4-benzyloxyphenylacetic 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

• Substituted monocyclic aryl compounds exhibiting selective leukotriene
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05232948A1

  公开（公告）日：1993-08-03

  Monocyclic aryl compounds having selective LTB.sub.4 antagonists properties and comprising an amido substituent, a substituent group having a terminal carboxylic acid or derivative thereof and a lipophilic substituent, therapeutic compositions and methods of treatment of disorders which result from LTB.sub.4 activity using the monocyclic aryl compounds are disclosed.

  本发明揭示了具有选择性LTB.sub.4拮抗剂特性的单环芳基化合物，其中包括一个酰胺取代基，一个具有末端羧酸或其衍生物的取代基团和一个亲脂性取代基，以及使用这些单环芳基化合物治疗由LTB.sub.4活性引起的疾病的治疗组合物和治疗方法。
• SUBSTITUTED MONOCYCLIC ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B 4? ANTAGONIST ACTIVITY
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：EP0538416A1

  公开（公告）日：1993-04-28
• EP0538416A4
  申请人：——

  公开号：EP0538416A4

  公开（公告）日：1994-05-18
• SUBSTITUTED MONOCYCLIC ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B 4 ANTAGONIST ACTIVITY
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：EP0538416B1

  公开（公告）日：1995-08-09
• US5232948A
  申请人：——

  公开号：US5232948A

  公开（公告）日：1993-08-03