(2-methoxyphenyl)[2-chloro-3-trifluoromethyl-4-(E-carboxyethenyl)phenyl]sulfide | 280753-13-1

• 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: (2-methoxyphenyl)[2-chloro-3-trifluoromethyl-4-(E-carboxyethenyl)phenyl]sulfide
• 英文别名: (E)-3-[3-chloro-4-(2-methoxyphenyl)sulfanyl-2-(trifluoromethyl)phenyl]prop-2-enoic acid
• CAS: 280753-13-1
• 化学式: C₁₇H₁₂ClF₃O₃S
• 分子量: 388.795
• InChiKey: HWLPULSBRGURBX-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-methoxyphenyl)[2-chloro-3-trifluoromethyl-4-(E-carboxyethenyl)phenyl]sulfide 在 sodium hydroxide 、 草酰氯 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 3.5h， 生成 (2-methoxyphenyl)[2-chloro-3-trifluoromethyl-4-(E-((4-carboxypiperidin-1-yl)carbonyl)ethenyl)phenyl]sulfide
  参考文献：
  名称：

  Discovery of Novel p-Arylthio Cinnamides as Antagonists of Leukocyte Function-Associated Antigen-1/Intercellular Adhesion Molecule-1 Interaction. 4. Structure−Activity Relationship of Substituents on the Benzene Ring of the Cinnamide

  摘要：

  We have shown that p-arylthio cinnamides can inhibit the interaction of LFA-1 and ICAM-1, which is involved in cell adhesion and the inflammatory process. We now show that 2,3-disubstitution on the aryl portion of the cinnamide results in enhanced activity over mono substitution on the ring. The best 2,3-substituents were chlorine and trifluoromethyl groups. Compounds 39 and 40 which contain two CF3 groups have IC50 values of 0.5 and 0.1 nM, respectively, in inhibiting JY8 cells expressing LFA-1 on their surface, from adhering to ICAM-1. The structure-activity relationship (SAR) was examined using an NMR based model of the LFA-1 I domain/compound 31 complex. One of our compounds (38) was able to reduce cell migration in two different in vivo experiments.

  DOI：

  10.1021/jm0103108
• 作为产物：
  描述：

  2-氯-3-羟基三氟甲苯 在 哌啶 、 吡啶 、 calcium hydroxide 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 2.8h， 生成 (2-methoxyphenyl)[2-chloro-3-trifluoromethyl-4-(E-carboxyethenyl)phenyl]sulfide
  参考文献：
  名称：

  Discovery of Novel p-Arylthio Cinnamides as Antagonists of Leukocyte Function-Associated Antigen-1/Intercellular Adhesion Molecule-1 Interaction. 4. Structure−Activity Relationship of Substituents on the Benzene Ring of the Cinnamide

  摘要：

  We have shown that p-arylthio cinnamides can inhibit the interaction of LFA-1 and ICAM-1, which is involved in cell adhesion and the inflammatory process. We now show that 2,3-disubstitution on the aryl portion of the cinnamide results in enhanced activity over mono substitution on the ring. The best 2,3-substituents were chlorine and trifluoromethyl groups. Compounds 39 and 40 which contain two CF3 groups have IC50 values of 0.5 and 0.1 nM, respectively, in inhibiting JY8 cells expressing LFA-1 on their surface, from adhering to ICAM-1. The structure-activity relationship (SAR) was examined using an NMR based model of the LFA-1 I domain/compound 31 complex. One of our compounds (38) was able to reduce cell migration in two different in vivo experiments.

  DOI：

  10.1021/jm0103108

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.

  本发明涉及一种新型肉桂酰胺化合物，可用于治疗炎症和免疫性疾病以及脑血管痉挛，以及包含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。