(2E)-3-{2-[(2,4-dichlorophenyl)thio]phenyl}acrylic acid | 280752-47-8

• 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: (2E)-3-{2-[(2,4-dichlorophenyl)thio]phenyl}acrylic acid
• 英文别名: trans-2-[(2,4-dichlorophenyl)thio]cinnamic acid；(E)-3-[2-(2,4-dichlorophenyl)sulfanylphenyl]prop-2-enoic acid
• CAS: 280752-47-8
• 化学式: C₁₅H₁₀Cl₂O₂S
• 分子量: 325.215
• InChiKey: VTZFPBIIWCXMIP-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-3-{2-[(2,4-dichlorophenyl)thio]phenyl}acrylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (E)-3-[2-(2,4-dichlorophenyl)sulfanylphenyl]prop-2-enoyl chloride
  参考文献：
  名称：

  Discovery of Novel p-Arylthio Cinnamides as Antagonists of Leukocyte Function-Associated Antigen-1/Intracellular Adhesion Molecule-1 Interaction. 1. Identification of an Additional Binding Pocket Based on an Anilino Diaryl Sulfide Lead

  摘要：

  The interaction between leukocyte function-associated antigen-1 (LFA-1), a member of the beta (2)-integrin family of adhesion molecules, and intracellular adhesion molecule ICAM-1 (cd54) is thought to play a critical role in the inflammatory process. On the basis of an anilino diaryl sulfide screening lead 1, in combination with pharmacophore analysis of other screening hits, we have identified an adjacent binding pocket. Subsequently, a p-ethenylcarbonyl linker was discovered to be optimal for accessing this binding site. Solution-phase parallel synthesis enabled rapid optimization of the cinnamides for this pocket. In conjunction with fine-tuning of the diaryl substituents, we discovered a novel series of potent, nonpeptide inhibitors of LFA-1/ICAM-1 interaction, exemplified by A-286982 (28h), which has IC50 values of 44 and 35 nM in an LFA-1/ICAM-1 binding assay and LFA-l-mediated cellular adhesion assay, respectively.

  DOI：

  10.1021/jm0002782
• 作为产物：
  描述：

  2,4-二氯苯硫酚 在 哌啶 、 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2E)-3-{2-[(2,4-dichlorophenyl)thio]phenyl}acrylic acid
  参考文献：
  名称：

  Discovery of Novel p-Arylthio Cinnamides as Antagonists of Leukocyte Function-Associated Antigen-1/Intracellular Adhesion Molecule-1 Interaction. 1. Identification of an Additional Binding Pocket Based on an Anilino Diaryl Sulfide Lead

  摘要：

  The interaction between leukocyte function-associated antigen-1 (LFA-1), a member of the beta (2)-integrin family of adhesion molecules, and intracellular adhesion molecule ICAM-1 (cd54) is thought to play a critical role in the inflammatory process. On the basis of an anilino diaryl sulfide screening lead 1, in combination with pharmacophore analysis of other screening hits, we have identified an adjacent binding pocket. Subsequently, a p-ethenylcarbonyl linker was discovered to be optimal for accessing this binding site. Solution-phase parallel synthesis enabled rapid optimization of the cinnamides for this pocket. In conjunction with fine-tuning of the diaryl substituents, we discovered a novel series of potent, nonpeptide inhibitors of LFA-1/ICAM-1 interaction, exemplified by A-286982 (28h), which has IC50 values of 44 and 35 nM in an LFA-1/ICAM-1 binding assay and LFA-l-mediated cellular adhesion assay, respectively.

  DOI：

  10.1021/jm0002782

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。
• Novel amides that activate soluble guanylate cyclase
  申请人：——

  公开号：US20040121994A1

  公开（公告）日：2004-06-24

  Compounds of formula (I) 1 are useful for increasing cGMP levels in a mammal.

  式(I)1的化合物对于增加哺乳动物体内cGMP水平是有用的。
• Cell adhesion-inhibiting antiinflammatory and immune-suppressive
  申请人：Abbott Laboratories

  公开号：US06110922A1

  公开（公告）日：2000-08-29

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

  本发明涉及一种新型的肉桂酰胺化合物，用于治疗炎症和免疫性疾病，包括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。
• Cell adhesion-inhibiting anti-inflammatory and immune-suppressive compounds
  申请人：Abbott Laboratories

  公开号：EP1481968A2

  公开（公告）日：2004-12-01

  The present invention relates to cinnamide compounds of formula (I), in which at least one of R1 to R5 is a "cis-cinnamide" (a) or a "trans-cinnamide" (b) and the other variables are as defined in the claims, that are useful for treating inflammatory and immune diseases, to pharmaceutical compositions containing these compounds and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及式（I）的肉桂酰胺化合物，其中 R1 至 R5 中至少有一个是 "顺式肉桂酰胺"（a）或 "反式肉桂酰胺"（b），其他变量如权利要求中所定义，本发明涉及可用于治疗炎症和免疫疾病的肉桂酰胺化合物、含有这些化合物的药物组合物以及抑制哺乳动物炎症或抑制免疫反应的方法。
• USRE039197E1
  申请人：——

  公开号：——

  公开（公告）日：——