1-[(E)-3-(Trifluoromethyl)-4-(2,3-dihydro-1,4-benzodioxin-6-ylthio)cinnamoyl]piperidine-3-carboxylic 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: 1-[(E)-3-(Trifluoromethyl)-4-(2,3-dihydro-1,4-benzodioxin-6-ylthio)cinnamoyl]piperidine-3-carboxylic acid
• 英文别名: 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidine-3-carboxylic acid
• 化学式: C₂₄H₂₂F₃NO₅S
• 分子量: 493.504
• InChiKey: XEKXLTGSRAVVJK-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-哌啶甲酸 、 (E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]prop-2-enoic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-[(E)-3-(Trifluoromethyl)-4-(2,3-dihydro-1,4-benzodioxin-6-ylthio)cinnamoyl]piperidine-3-carboxylic acid
  参考文献：
  名称：

  Discovery of Potent Antagonists of Leukocyte Function-Associated Antigen-1/Intercellular Adhesion Molecule-1 Interaction. 3. Amide (C-Ring) Structure−Activity Relationship and Improvement of Overall Properties of Arylthio Cinnamides

  摘要：

  The interaction of LFA-1 and ICAM-1 plays an important role in the cell adhesion process. On the basis of previously reported SAR and structural information on the binding of our p-arylthiocinnamide series to LFA-1, we have identified the cyclic amide (C-ring) as a site for modification. Improvement in potency and, more importantly, in the physical properties and pharmacokinetic profiles of the leading compounds resulted from this modification. One of the best compounds (11f) is also shown to reduce myocardial infarct size in rat.

  DOI：

  10.1021/jm010059w

文献信息

• Discovery of Potent Antagonists of Leukocyte Function-Associated Antigen-1/Intercellular Adhesion Molecule-1 Interaction. 3. Amide (C-Ring) Structure−Activity Relationship and Improvement of Overall Properties of Arylthio Cinnamides
  作者：Zhonghua Pei、Zhili Xin、Gang Liu、Yihong Li、Edward B. Reilly、Nathan L. Lubbers、Jeffery R. Huth、James T. Link、Thomas W. von Geldern、Bryan F. Cox、Sandra Leitza、Yi Gao、Kennan C. Marsh、Peter DeVries、Greg F. Okasinski

  DOI：10.1021/jm010059w

  日期：2001.8.1

  The interaction of LFA-1 and ICAM-1 plays an important role in the cell adhesion process. On the basis of previously reported SAR and structural information on the binding of our p-arylthiocinnamide series to LFA-1, we have identified the cyclic amide (C-ring) as a site for modification. Improvement in potency and, more importantly, in the physical properties and pharmacokinetic profiles of the leading compounds resulted from this modification. One of the best compounds (11f) is also shown to reduce myocardial infarct size in rat.