4-(4-Fluoro-phenyl)-4-oxo-N-phenyl-butyramide | 38752-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-Fluoro-phenyl)-4-oxo-N-phenyl-butyramide
• 英文别名: 4-(4-fluorophenyl)-4-oxo-N-phenylbutanamide
• CAS: 38752-59-9
• 化学式: C₁₆H₁₄FNO₂
• 分子量: 271.291
• InChiKey: JKZUNPYXLQXDCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-phenyl)-4-oxo-N-phenyl-butyramide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 4-(4-fluorophenyl)-4-hydroxy-N-phenylbutanamide
  参考文献：
  名称：

  COMPOUNDS TO INHIBIT CALCIUM/CALMODULIN DEPENDENT PROTEIN KINASE II AND APPLICATIONS THEREOF

  摘要：

  提供了一些新型苯磺酰胺化合物，可以抑制钙/钙调蛋白激酶II（CaMKII）的活性，以及含有这些苯磺酰胺化合物的药物组合物。此外，还提供了使用这些苯磺酰胺化合物治疗与CaMKII活性有关的疾病或病症（如黄病毒感染）的方法。

  公开号：

  US20190300475A1
• 作为产物：
  描述：

  苯胺 、 3-(4-氟苯甲酰基)丙酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以92%的产率得到4-(4-Fluoro-phenyl)-4-oxo-N-phenyl-butyramide
  参考文献：
  名称：

  COMPOUNDS TO INHIBIT CALCIUM/CALMODULIN DEPENDENT PROTEIN KINASE II AND APPLICATIONS THEREOF

  摘要：

  提供了一些新型苯磺酰胺化合物，可以抑制钙/钙调蛋白激酶II（CaMKII）的活性，以及含有这些苯磺酰胺化合物的药物组合物。此外，还提供了使用这些苯磺酰胺化合物治疗与CaMKII活性有关的疾病或病症（如黄病毒感染）的方法。

  公开号：

  US20190300475A1

文献信息

• Modulation of 11β-hydroxysteroid dehydrogenase type 1 activity by 1,5-substituted 1H-tetrazoles
  作者：Scott P. Webster、Margaret Binnie、Kirsty M.M. McConnell、Karen Sooy、Peter Ward、Michael F. Greaney、Andy Vinter、T. David Pallin、Hazel J. Dyke、Matthew I.A. Gill、Ines Warner、Jonathan R. Seckl、Brian R. Walker

  DOI：10.1016/j.bmcl.2010.04.055

  日期：2010.6

  Inhibitors of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD1) show promise as drugs to treat metabolic disease and CNS disorders such as cognitive impairment. A series of 1,5-substituted 1H-tetrazole 11 beta-HSD1 inhibitors has been discovered and chemically modified. Compounds are selective for 11 beta-HSD1 over 11 beta-HSD2 and possess good cellular potency in human and murine 11 beta-HSD1 assays. A range of in vitro stabilities are observed in human liver microsome assays. (C) 2010 Elsevier Ltd. All rights reserved.
• Benzenesulfonamide Derivatives as Calcium/Calmodulin-Dependent Protein Kinase Inhibitors and Antiviral Agents against Dengue and Zika Virus Infections
  作者：Wei-Chia Chen、Yogy Simanjuntak、Li-Wei Chu、Yueh-Hsin Ping、Yi-Ling Lee、Yi-Ling Lin、Wen-Shan Li

  DOI：10.1021/acs.jmedchem.9b01779

  日期：2020.2.13

  Emerging and resurging mosquito-borne flaviviruses are an important public health challenge. The increased prevalence of dengue virus (DENY) infection has had a significant socioeconomic impact on epidemic countries. The recent outbreak of Zika virus (ZIKV) has created an international public health emergency because ZIKV infection has been linked to congenital defects and Guillain-Barre syndrome. To develop potentially prophylactic antiviral drugs for combating these acute infectious diseases, we have targeted the host calcium/calmodulin-dependent kinase II (CaMKII) for inhibition. By using CaMKII structure-guided inhibitor design, we generated four families of benzenesulfonamide (BSA) derivatives for SAR analysis. Among these substances, N-(4-cyclohepty1-4-oxobuty1)-4-methoxy-N-phenylbenzenesulfonamide (9) showed superior properties as a lead CaMKII inhibitor and antiviral agent. BSA 9 inhibited CaMKII activity with an IC50 value of 0.79 mu M and displayed EC50 values of 1.52 mu M and 1.91 mu M against DENY and ZIKV infections of human neuronal BE(2)C cells, respectively. Notably, 9 significantly reduced the viremia level and increased animal survival time in mouse-challenge models.
• COMPOUNDS TO INHIBIT CALCIUM/CALMODULIN DEPENDENT PROTEIN KINASE II AND APPLICATIONS THEREOF
  申请人：ACADEMIA SINICA

  公开号：US20190300475A1

  公开（公告）日：2019-10-03

  Provided are novel benzenesulfonamide compounds that inhibit calcium/calmodulin-dependent protein kinase II (CaMKII) and pharmaceutical compositions containing the benzenesulfonamide compounds. Also provided are methods of using the benzenesulfonamide compounds to treat diseases or conditions that are associated with CaMKII activity, such as a flavivirus infection.

  提供了一些新型苯磺酰胺化合物，可以抑制钙/钙调蛋白激酶II（CaMKII）的活性，以及含有这些苯磺酰胺化合物的药物组合物。此外，还提供了使用这些苯磺酰胺化合物治疗与CaMKII活性有关的疾病或病症（如黄病毒感染）的方法。