3'-氯-4'-氟-4-联苯基羧酸 | 195457-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3'-氯-4'-氟-4-联苯基羧酸
• 中文别名: 2-甲基-2-戊基-1,3-二噁戊环
• 英文名称: 3'-Chloro-4'-fluoro-biphenyl-4-carboxylic acid
• 英文别名: 4-(3-Chloro-4-fluorophenyl)benzoic acid
• CAS: 195457-73-9
• 化学式: C₁₃H₈ClFO₂
• 分子量: 250.657
• InChiKey: WAWQPHGUJGYFMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±35.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯甲酸 、 3-氯-4-氟苯硼酸 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 Wang resin 作用下， 生成 3'-氯-4'-氟-4-联苯基羧酸
  参考文献：
  名称：

  NMR-Based Discovery of Lead Inhibitors That Block DNA Binding of the Human Papillomavirus E2 Protein

  摘要：

  The E2 protein is required far the replication of human papillomaviruses (HPVs), which are responsible for anogenital warts and cervical carcinomas, Using an NMR-based screen, we tested compounds for binding to the DNA-binding domain of the HPV-E2 protein. Three classes of compounds were identified which bound to two distinct sites on the protein. Biphenyl and biphenyl ether compounds containing a carboxylic acid bind to a site near the DNA recognition helix and inhibit the binding of E2 to DNA. Benzophenone-containing compounds which lack a carboxylic acid group bind to the beta-barrel formed by the dimer intel face and exhibit negligible effects on the binding of E2 to DNA. Structure-activity relationships from the biphenyl and biphenyl ether compounds were combined to produce a compound [5-(3'-(3 '',5 ''-dichlorophenoxy)phenyl)-2,4-pentadienoic acid] with an IC50 value of approximately 10 mu M. This compound represents a useful lead for the development of antiviral agents that interfere with HPV replication and further illustrates the usefulness of the SAR by NMR method in the drug discovery process.

  DOI：

  10.1021/jm9703404

文献信息

• ARYL/HETARYLAMIDES AS MODULATORS OF THE EP2 RECEPTOR
  申请人：Buchmann Bernd

  公开号：US20090023741A1

  公开（公告）日：2009-01-22

  The present invention relates to aryl/hetarylamide derivatives of the general formula I, process for their preparation, and the use thereof for the manufacture of pharmaceutical compositions for the treatment of disorders and indications connected with the EP 2 receptor.

  本发明涉及通式I的芳基/杂环酰胺衍生物，其制备方法，以及用于制造治疗与EP2受体相关的疾病和适应症的药物组合物的用途。
• [EN] ARYL/HETARYLAMIDES AS MODULATORS OF THE EP2 RECEPTOR<br/>[FR] ARYL/HÉTARYLAMIDES EN TANT QUE MODULATEURS DU RÉCEPTEUR EP2
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2008152099A2

  公开（公告）日：2008-12-18

  [EN] The present invention relates to aryl/ hetarylamide derivativ es of the general formula (I), process for their preparation, and the use thereof for the manufacture of pharmaceutical compositions for the treatment of disorders and indications connected with the EP2 receptor.
  [FR] La présente invention porte sur des dérivés d'aryle/hétarylamide de la formule générale (I), sur un procédé pour leur préparation et sur l'utilisation de ceux-ci dans la fabrication de compositions pharmaceutiques pour le traitement de troubles et d'indications associés au récepteur EP2.
• NMR-Based Discovery of Lead Inhibitors That Block DNA Binding of the Human Papillomavirus E2 Protein
  作者：Philip J. Hajduk、Jürgen Dinges、Gregory F. Miknis、Megan Merlock、Tim Middleton、Dale J. Kempf、David A. Egan、Karl A. Walter、Terry S. Robins、Suzy B. Shuker、Thomas F. Holzman、Stephen W. Fesik

  DOI：10.1021/jm9703404

  日期：1997.9.1

  The E2 protein is required far the replication of human papillomaviruses (HPVs), which are responsible for anogenital warts and cervical carcinomas, Using an NMR-based screen, we tested compounds for binding to the DNA-binding domain of the HPV-E2 protein. Three classes of compounds were identified which bound to two distinct sites on the protein. Biphenyl and biphenyl ether compounds containing a carboxylic acid bind to a site near the DNA recognition helix and inhibit the binding of E2 to DNA. Benzophenone-containing compounds which lack a carboxylic acid group bind to the beta-barrel formed by the dimer intel face and exhibit negligible effects on the binding of E2 to DNA. Structure-activity relationships from the biphenyl and biphenyl ether compounds were combined to produce a compound [5-(3'-(3 '',5 ''-dichlorophenoxy)phenyl)-2,4-pentadienoic acid] with an IC50 value of approximately 10 mu M. This compound represents a useful lead for the development of antiviral agents that interfere with HPV replication and further illustrates the usefulness of the SAR by NMR method in the drug discovery process.