N-(4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)-2-fluorobenzamide | 1443114-10-0

• 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-(4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)-2-fluorobenzamide
• 英文别名: N-[4-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-yl]-2-fluorobenzamide
• CAS: 1443114-10-0
• 化学式: C₁₆H₁₀FN₅O₂
• 分子量: 323.286
• InChiKey: HHCLGAAQDLMHRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)-2-fluorobenzamide 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 N-(4-(1-(2-(4-aminophenyl)-2-oxoethyl)-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)-2-fluorobenzamide
  参考文献：
  名称：

  Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy

  摘要：

  Targeting host cell factors required for virus replication provides an alternative to targeting pathogen components and represents a promising approach to develop broad-spectrum antiviral therapeutics. High-throughput screening (HTS) identified two classes of inhibitors (2 and 3) with broad-spectrum antiviral activity against ortho- and paramyxoviruses including influenza A virus (IAV), measles virus (MeV), respiratory syncytial virus (RSV), and human parainfluenza virus type 3 (HPIV3). Hit-to-lead optimization delivered inhibitor 28a, with EC50 values of 0.88 and 0.81 mu M against IAV strain WSN and MeV strain Edmonston, respectively. It was also found that compound 28a delivers good stability in human liver S9 fractions with a half-life of 165 min. These data establish 28a as a promising lead for antiviral therapy through a host-directed mechanism.

  DOI：

  10.1021/ml400166b
• 作为产物：
  描述：

  邻氟苯甲酰氯 、 4-(1H-苯并咪唑-2-基)-1,2,5-恶二唑-3-胺 在 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以69%的产率得到N-(4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)-2-fluorobenzamide
  参考文献：
  名称：

  Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy

  摘要：

  Targeting host cell factors required for virus replication provides an alternative to targeting pathogen components and represents a promising approach to develop broad-spectrum antiviral therapeutics. High-throughput screening (HTS) identified two classes of inhibitors (2 and 3) with broad-spectrum antiviral activity against ortho- and paramyxoviruses including influenza A virus (IAV), measles virus (MeV), respiratory syncytial virus (RSV), and human parainfluenza virus type 3 (HPIV3). Hit-to-lead optimization delivered inhibitor 28a, with EC50 values of 0.88 and 0.81 mu M against IAV strain WSN and MeV strain Edmonston, respectively. It was also found that compound 28a delivers good stability in human liver S9 fractions with a half-life of 165 min. These data establish 28a as a promising lead for antiviral therapy through a host-directed mechanism.

  DOI：

  10.1021/ml400166b

文献信息

• Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy
  作者：Terry W. Moore、Kasinath Sana、Dan Yan、Stefanie A. Krumm、Pahk Thepchatri、James P. Snyder、José Marengo、Richard F. Arrendale、Andrew J. Prussia、Michael G. Natchus、Dennis C. Liotta、Richard K. Plemper、Aiming Sun

  DOI：10.1021/ml400166b

  日期：2013.8.8

  Targeting host cell factors required for virus replication provides an alternative to targeting pathogen components and represents a promising approach to develop broad-spectrum antiviral therapeutics. High-throughput screening (HTS) identified two classes of inhibitors (2 and 3) with broad-spectrum antiviral activity against ortho- and paramyxoviruses including influenza A virus (IAV), measles virus (MeV), respiratory syncytial virus (RSV), and human parainfluenza virus type 3 (HPIV3). Hit-to-lead optimization delivered inhibitor 28a, with EC50 values of 0.88 and 0.81 mu M against IAV strain WSN and MeV strain Edmonston, respectively. It was also found that compound 28a delivers good stability in human liver S9 fractions with a half-life of 165 min. These data establish 28a as a promising lead for antiviral therapy through a host-directed mechanism.