[3-[[[5-Cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]-methylsulfonylamino]methyl]phenyl]boronic acid | 1331942-27-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: [3-[[[5-Cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]-methylsulfonylamino]methyl]phenyl]boronic acid
• CAS: 1331942-27-8
• 化学式: C₂₇H₂₆BFN₂O₆S
• 分子量: 536.389
• InChiKey: CQLNBWIRHOHQQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-环丙基-2-(4-氟苯基)-N-甲基-6-(甲基磺酰氨基)苯并呋喃-3-甲酰胺 、 3-溴甲基苯硼酸 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以20%的产率得到[3-[[[5-Cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]-methylsulfonylamino]methyl]phenyl]boronic acid
  参考文献：
  名称：

  Discovery of a Potent Boronic Acid Derived Inhibitor of the HCV RNA-Dependent RNA Polymerase

  摘要：

  A boronic acid moiety was found to be a critical pharmacophore for enhanced in vitro potency against wild-type hepatitis C replicons and known clinical polymorphic and resistant HCV mutant replicons. The synthesis, optimization, and structure-activity relationships associated with inhibition of HCV replication in a subgenomic replication system for a series of non-nucleoside boron-containing HCV RNA-dependent RNA polymerase (NS5B) inhibitors are described. A summary of the discovery of 3 (GSK5852), a molecule which entered clinical trials in subjects infected with HCV in 2011, is included.

  DOI：

  10.1021/jm400317w