6-Amino-4-oxo-1,7-bis-(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: 6-Amino-4-oxo-1,7-bis-(4-pyridin-2-yl-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6-Amino-4-oxo-1,7-bis[4-(2-pyridyl)piperazin-1-yl]quinoline-3-carboxylic acid；6-amino-4-oxo-1,7-bis(4-pyridin-2-ylpiperazin-1-yl)quinoline-3-carboxylic acid
• 化学式: C₂₈H₃₀N₈O₃
• 分子量: 526.598
• InChiKey: IKCGFUNPARXQEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  7-Chloro-6-nitro-4-oxo-1-(4-pyridin-2-yl-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 盐酸 、 氢气 、 镍 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 6-Amino-4-oxo-1,7-bis-(4-pyridin-2-yl-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Structure Modifications of 6-Aminoquinolones with Potent Anti-HIV Activity

  摘要：

  We have recently discovered that 6-aminoquinolone derivatives could be valid leads for the development of new anti-HIV agents because of their new and diversified mode of action. In fact, studies carried out on the lead WM5 showed that this derivative is able to inhibit the Tat-mediated long terminal repeat driven transcription, an essential step in the HIV-1 replication cycle. Thus, starting from lead WM5, we performed the design and synthesis of an enlarged series of 6-aminoquinolones, which permitted some very potent anti-HIV 6-amino derivatives to be obtained and the structure-activity relationship to be delineated. Some derivatives, 26c, 26e, 26i, and 26j, proved to be highly effective in inhibiting HIV replication at 50% inhibitory concentration in the range of 0.0087-0.7 mug/mL in MT-4, PBMCs and CEM cell lines coupled with positive selectivity indexes that reach values higher than 1000 on CEM cell lines for compounds 26e and 26i. Time-of-addition experiments clearly confirm that the new, potent 6-aminoquinolones interact at a postintegration step in the replication cycle of HIV.

  DOI：

  10.1021/jm049721p