1-tert-Butyl-6-fluoro-4-oxo-7-(4-pyridin-2-yl-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-tert-Butyl-6-fluoro-4-oxo-7-(4-pyridin-2-yl-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 1-Tert-butyl-6-fluoro-4-oxo-7-[4-(2-pyridyl)piperazin-1-yl]quinoline-3-carboxylic acid；1-tert-butyl-6-fluoro-4-oxo-7-(4-pyridin-2-ylpiperazin-1-yl)quinoline-3-carboxylic acid
• 化学式: C₂₃H₂₅FN₄O₃
• 分子量: 424.475
• InChiKey: XNBXEJAEIXAJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(叔丁基)-7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-tert-Butyl-6-fluoro-4-oxo-7-(4-pyridin-2-yl-piperazin-1-yl)-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