(8S)-N-{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-5,6,7,8-tetrahydro-8-quinolinamine

• 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: (8S)-N-{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-5,6,7,8-tetrahydro-8-quinolinamine
• 英文别名: (8S)-N{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-5,6,7,8-tetrahydro-8-quinolinamine；(8S)-N-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine
• 化学式: C₂₂H₂₈N₆
• 分子量: 376.505
• InChiKey: ITPSDEVJHDJOQI-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8S)-N-{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-5,6,7,8-tetrahydro-8-quinolinamine 、 2,2,2-三氟乙醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 N-{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-N-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydro-8-quinolinamine
  参考文献：
  名称：

  Imidazopyridine-5,6,7,8-tetrahydro-8-quinolinamine derivatives with potent activity against HIV-1

  摘要：

  Synthesis of several novel imidazopyridine-5,6,7,8-tetrahydro-8-quinolinamine derivatives with potent activity against HIV are described. Synthetic approaches allowing for variation of the substitution pattern are outlined and resulting changes in antiviral activity and pharmacokinetics are highlighted. Several compounds with low nanomolar anti-HIV activity and oral bioavailability are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.056
• 作为产物：
  描述：

  (8S)-N-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-N-{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-5,6,7,8-tetrahydro-8-quinolinamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(8S)-N-{[5-(4-methyl-1-piperazinyl)imidazo[1,2-a]pyridin-2-yl]methyl}-5,6,7,8-tetrahydro-8-quinolinamine
  参考文献：
  名称：

  Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397

  摘要：

  An improved, scalable synthesis of the CXCR4 antagonist GSK812397 is described. This new route was recently scaled up in 50 L fixed equipment to afford 1.2 kg of drug substance in five steps with an overall yield of 20% and >99% chemical and enantiomeric purity.

  DOI：

  10.1021/op9000675

文献信息

• Chemical Compounds
  申请人：Gudmundsson Kristian

  公开号：US20070232615A1

  公开（公告）日：2007-10-04

  The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind to a chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 of a target cell.

  本发明提供了一种新型化合物，它们以一种与趋化因子受体结合的方式对目标细胞表现出对HIV感染的保护作用，并影响天然配体或趋化因子与目标细胞的CXCR4等受体的结合。
• CHEMICAL COMPOUNDS
  申请人：GUDMUNDSSON Kristjan

  公开号：US20070254910A1

  公开（公告）日：2007-11-01

  The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind to a chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 of a target cell.

  本发明提供了一种新型化合物，它们以一种与趋化因子受体结合的方式对靶细胞表现出对HIV感染的保护作用，并影响自然配体或趋化因子与靶细胞的CXCR4等受体的结合。
• WO2007/27999
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006036816A3

  公开（公告）日：2006-06-15
• WO2007/87549
  申请人：——

  公开号：——

  公开（公告）日：——