ethyl (E)-2-((5-chloropyridin-3-yl)diazenyl)-3-(4-fluorophenyl)-3-oxopropanoate | 1596216-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (E)-2-((5-chloropyridin-3-yl)diazenyl)-3-(4-fluorophenyl)-3-oxopropanoate
• CAS: 1596216-92-0
• 化学式: C₁₆H₁₃ClFN₃O₃
• 分子量: 349.749
• InChiKey: TXOAXAQLPULZSG-QZQOTICOSA-N

物化性质

• 沸点：
  448.5±45.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-((5-chloropyridin-3-yl)diazenyl)-3-(4-fluorophenyl)-3-oxopropanoate 在 盐酸 、 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以266 mg的产率得到(E)-4-((5-chloropyridin-3-yl)diazenyl)-3-(4-fluorophenyl)-1H-pyrazol-5-ol
  参考文献：
  名称：

  Synthesis and structure–activity analysis of diphenylpyrazolodiazene inhibitors of the HIV-1 Nef virulence factor

  摘要：

  HIV-1 Nef is a critical AIDS progression factor yet underexplored target for antiretroviral drug discovery. A recent high-throughput screen for pharmacological inhibitors of Nef-dependent Src-family kinase activation identified a diphenylpyrazolodiazene hit compound with submicromolar potency in HIV-1 replication assays against a broad range of primary Nef variants. This compound, known as 'B9', binds directly to Nef and inhibits its dimerization in cells as a possible mechanism of action. Here were synthesized a diverse set of B9 analogs and identified structural features essential to antiretroviral activity. Chemical modifications to each of the three rings present in the parent compound were identified that did not compromise antiviral action. These analogs will guide the development of next-generation compounds with appropriate pharmacological profiles for assessment of antiretroviral activity in vivo. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.045
• 作为产物：
  描述：

  3-氨基-5-氯吡啶 、 4-氟苯甲酰乙酸乙酯 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 溶剂黄146 、 甲醇 为溶剂， 反应 0.75h， 生成 ethyl (E)-2-((5-chloropyridin-3-yl)diazenyl)-3-(4-fluorophenyl)-3-oxopropanoate
  参考文献：
  名称：

  Synthesis and structure–activity analysis of diphenylpyrazolodiazene inhibitors of the HIV-1 Nef virulence factor

  摘要：

  HIV-1 Nef is a critical AIDS progression factor yet underexplored target for antiretroviral drug discovery. A recent high-throughput screen for pharmacological inhibitors of Nef-dependent Src-family kinase activation identified a diphenylpyrazolodiazene hit compound with submicromolar potency in HIV-1 replication assays against a broad range of primary Nef variants. This compound, known as 'B9', binds directly to Nef and inhibits its dimerization in cells as a possible mechanism of action. Here were synthesized a diverse set of B9 analogs and identified structural features essential to antiretroviral activity. Chemical modifications to each of the three rings present in the parent compound were identified that did not compromise antiviral action. These analogs will guide the development of next-generation compounds with appropriate pharmacological profiles for assessment of antiretroviral activity in vivo. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.045