3-[4-(2-isopropylphenylsulfanyl)-3-nitrophenyl]acrylic acid | 280752-62-7

• 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-[4-(2-isopropylphenylsulfanyl)-3-nitrophenyl]acrylic acid
• 英文别名: (2-isopropylphenyl)[2-nitro-4-(E-(carboxy)ethenyl)phenyl]sulfide；(E)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-enoic acid
• CAS: 280752-62-7
• 化学式: C₁₈H₁₇NO₄S
• 分子量: 343.403
• InChiKey: XDSKCZFJBUVZIG-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[4-(2-isopropylphenylsulfanyl)-3-nitrophenyl]acrylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-1-(3-Hydroxymethyl-piperazin-1-yl)-3-[4-(2-isopropyl-phenylsulfanyl)-3-nitro-phenyl]-propenone
  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
• 作为产物：
  描述：

  2-异丙基苯硫酚 、 4-氯-3-硝基肉桂酸 在 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 生成 3-[4-(2-isopropylphenylsulfanyl)-3-nitrophenyl]acrylic acid
  参考文献：
  名称：

  Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds

  摘要：

  本发明涉及新型肉桂酰胺化合物，用于治疗炎症和免疫性疾病以及脑血管痉挛，以及含有这些化合物的药物组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。

  公开号：

  US20040116518A1

文献信息

• Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds
  申请人：Abbott Laboratories

  公开号：US20040116518A1

  公开（公告）日：2004-06-17

  The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases and cerebral vasospasm, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及新型肉桂酰胺化合物，用于治疗炎症和免疫性疾病以及脑血管痉挛，以及含有这些化合物的药物组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• 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.