ethyl 6-amino-7-[4-(4-fluorophenyl)-1-piperazinyl]-1-tert-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate | 304897-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 6-amino-7-[4-(4-fluorophenyl)-1-piperazinyl]-1-tert-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS: 304897-91-4
• 化学式: C₂₆H₃₁FN₄O₃
• 分子量: 466.556
• InChiKey: PSXFWGVVTOMRCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.8
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-amino-7-[4-(4-fluorophenyl)-1-piperazinyl]-1-tert-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 sodium hydroxide 作用下， 反应 3.5h， 以87%的产率得到6-Amino-1-tert-butyl-7-[4-(4-fluoro-phenyl)-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  6-Aminoquinolones as New Potential Anti-HIV Agents

  摘要：

  A series of 6-aminoquinolone compounds were evaluated for their in vitro activity against human immunodeficiency virus type 1 (HIV-1). Compound 12a, bearing a methyl substituent at the N-1 position and a 4-(2-pyridyl)-1-piperazine moiety at the C-7 position, was the most active in inhibiting HIV-1 replication on de novo infected C8166 human lymphoblastoid cell lines. The 12a EC50 value was 0.1 mu M, a 7-20-fold lower concentration relative to that for compounds 8a and 7a containing a cyclopropyl and tert-butyl substituent at the N-1 position, respectively. When the C-6 amino group was replaced with a fluorine atom, a decreased antiviral effect was observed. The observed effects are selective, since potency is substantially reduced when testing the compounds against the herpes simplex virus type 1 (HSV-1). Active quinolone derivatives very efficiently interact with TAR RNA, which suggests a nucleic acid-targeted mechanism of action.

  DOI：

  10.1021/jm9903390
• 作为产物：
  描述：

  1-(4-氟苯基)哌嗪 在 镍 氢气 作用下， 以 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、207.73 kPa 条件下， 反应 6.0h， 生成 ethyl 6-amino-7-[4-(4-fluorophenyl)-1-piperazinyl]-1-tert-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  6-Aminoquinolones as New Potential Anti-HIV Agents

  摘要：

  A series of 6-aminoquinolone compounds were evaluated for their in vitro activity against human immunodeficiency virus type 1 (HIV-1). Compound 12a, bearing a methyl substituent at the N-1 position and a 4-(2-pyridyl)-1-piperazine moiety at the C-7 position, was the most active in inhibiting HIV-1 replication on de novo infected C8166 human lymphoblastoid cell lines. The 12a EC50 value was 0.1 mu M, a 7-20-fold lower concentration relative to that for compounds 8a and 7a containing a cyclopropyl and tert-butyl substituent at the N-1 position, respectively. When the C-6 amino group was replaced with a fluorine atom, a decreased antiviral effect was observed. The observed effects are selective, since potency is substantially reduced when testing the compounds against the herpes simplex virus type 1 (HSV-1). Active quinolone derivatives very efficiently interact with TAR RNA, which suggests a nucleic acid-targeted mechanism of action.

  DOI：

  10.1021/jm9903390