6-amino-1-methyl-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic acid | 1178570-32-5

• 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-1-methyl-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 6-Amino-1-methyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 1178570-32-5
• 化学式: C₁₅H₁₈N₄O₃
• 分子量: 302.333
• InChiKey: TXOSIBMHZBOWDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.9
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-amino-1-methyl-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic acid 、 9-chloro-11-ethyl-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 以32%的产率得到6-amino-7-[4-(11-ethyl-6-oxo-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-9-yl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Exploiting the anti-HIV 6-desfluoroquinolones to design multiple ligands

  摘要：

  It is getting clearer that many drugs effective in different therapeutic areas act on multiple rather than single targets. The application of polypharmacology concepts might have numerous advantages especially for disease such as HIV/AIDS, where the rapid emergence of resistance requires a complex combination of more than one drug. In this paper, we have designed three hybrid molecules combining WM5, a quinolone derivative we previously identified as HIV Tat-mediated transcription (TMT) inhibitor, with the tricyclic core of nevirapine and BILR 355BS (BILR) non-nucleoside reverse transcriptase inhibitors (NNRTIs) to investigate whether it could be possible to obtain molecules acting on both transcription steps of the HIV replicative cycle. One among the three designed multiple ligands, reached this goal. Indeed, compound 1 inhibited both TMT and reverse transcriptase (RT) activity. Unexpectedly, while the anti-TMT activity exerted by compound 1 resulted into a selective inhibition of HIV-1 reactivation from latently infected OM10.1 cells, the anti-RT properties shown by all of the synthesized compounds did not translate into an anti-HIV activity in acutely infected cells. Thus, we have herein produced the proof of concept that the design of dual TMT-RT inhibitors is indeed possible, but optimization efforts are needed to obtain more potent derivatives.

  DOI：

  10.1016/j.bmc.2014.07.018