N-(2-chloro-4-nitrophenyl)-4-hydroxy-[1,1‘-biphenyl]-3-carboxamide | 1428329-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-chloro-4-nitrophenyl)-4-hydroxy-[1,1‘-biphenyl]-3-carboxamide
• 英文别名: N-(2-chloro-4-nitrophenyl)-2-hydroxy-5-phenylbenzamide
• CAS: 1428329-00-3
• 化学式: C₁₉H₁₃ClN₂O₄
• 分子量: 368.776
• InChiKey: OPCFESYTPXDZHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-碘水杨酸 、 2-氯-4-硝基苯胺 在 palladium diacetate 、 三溴化磷 、 potassium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(2-chloro-4-nitrophenyl)-4-hydroxy-[1,1‘-biphenyl]-3-carboxamide
  参考文献：
  名称：

  Small molecule modulators of Wnt/β-catenin signaling

  摘要：

  The Wnt signal transduction pathway is dysregulated in many highly prevalent diseases, including cancer. Unfortunately, drug discovery efforts have been hampered by the paucity of targets and drug-like lead molecules amenable to drug discovery. Recently, we reported the FDA-approved anthelmintic drug Niclosamide inhibits Wnt/beta-catenin signaling by a unique mechanism, though the target responsible remains unknown. We interrogated the mechanism and structure-activity relationships to understand drivers of potency and to assist target identification efforts. We found inhibition of Wnt signaling by Niclosamide appears unique among the structurally-related anthelmintic agents tested and found the potency and functional response was dependent on small changes in the chemical structure of Niclosamide. Overall, these findings support efforts to identify the target of Niclosamide inhibition of Wnt/beta-catenin signaling And the discovery of potent and selective modulators to treat human disease. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.101

文献信息

• [EN] CHEMICAL MODULATORS OF SIGNALING PATHWAYS AND THERAPEUTIC USE<br/>[FR] MODULATEURS CHIMIQUES DES VOIES DE SIGNALISATION ET UTILISATION THÉRAPEUTIQUE
  申请人：UNIV DUKE

  公开号：WO2016210289A1

  公开（公告）日：2016-12-29

  Described are methods of treating a disease associated with dysregulation of the Wnt/Frizzled signaling pathway. The methods include identifying subjects in need of therapy, administering inhibitors of the Wnt/Frizzled signaling pathway, pharmaceutical compositions including the inhibitors, and methods of using the compounds and compositions for treating cancer, bacterial and viral infection, lupus, type II diabetes, nonalcoholic steatohepatitis (NASH) and nonalcoholic fatty liver disease (NAFLD) in a subject.

  描述了治疗与Wnt/Frizzled信号通路失调相关的疾病的方法。这些方法包括识别需要治疗的对象，给予Wnt/Frizzled信号通路抑制剂，包括这些抑制剂的药物组合物，以及使用这些化合物和组合物治疗癌症、细菌和病毒感染、红斑狼疮、2型糖尿病、非酒精性脂肪肝炎（NASH）和非酒精性脂肪肝病（NAFLD）的方法。
• Chemical modulators of signaling pathways and therapeutic use
  申请人：Duke University

  公开号：US10905665B2

  公开（公告）日：2021-02-02

  Described are methods of treating a disease associated with dysregulation of the Wnt/Frizzled signaling pathway. The methods include identifying subjects in need of therapy, administering inhibitors of the Wnt/Frizzled signaling pathway, pharmaceutical compositions including the inhibitors, and methods of using the compounds and compositions for treating cancer, bacterial and viral infection, lupus, type II diabetes, nonalcoholic steatohepatitis (NASH) and nonalcoholic fatty liver disease (NAFLD) in a subject.

  描述了治疗与 Wnt/Frizzled 信号通路失调有关的疾病的方法。这些方法包括鉴定需要治疗的受试者、施用 Wnt/Frizzled 信号通路抑制剂、包括抑制剂的药物组合物，以及使用化合物和组合物治疗受试者的癌症、细菌和病毒感染、狼疮、II 型糖尿病、非酒精性脂肪性肝炎（NASH）和非酒精性脂肪肝（NAFLD）的方法。
• CHEMICAL MODULATORS OF SIGNALING PATHWAYS AND THERAPEUTIC USE
  申请人：Duke University

  公开号：EP3313388A1

  公开（公告）日：2018-05-02
• Small molecule modulators of Wnt/β-catenin signaling
  作者：Robert A. Mook、Minyong Chen、Jiuyi Lu、Larry S. Barak、H. Kim Lyerly、Wei Chen

  DOI：10.1016/j.bmcl.2013.01.101

  日期：2013.4

  The Wnt signal transduction pathway is dysregulated in many highly prevalent diseases, including cancer. Unfortunately, drug discovery efforts have been hampered by the paucity of targets and drug-like lead molecules amenable to drug discovery. Recently, we reported the FDA-approved anthelmintic drug Niclosamide inhibits Wnt/beta-catenin signaling by a unique mechanism, though the target responsible remains unknown. We interrogated the mechanism and structure-activity relationships to understand drivers of potency and to assist target identification efforts. We found inhibition of Wnt signaling by Niclosamide appears unique among the structurally-related anthelmintic agents tested and found the potency and functional response was dependent on small changes in the chemical structure of Niclosamide. Overall, these findings support efforts to identify the target of Niclosamide inhibition of Wnt/beta-catenin signaling And the discovery of potent and selective modulators to treat human disease. (C) 2013 Elsevier Ltd. All rights reserved.