3-(2-{[methyl(5,6,7,8-tetrahydro-8-quinolinyl)amino]methyl}-1H-benzimidazol-4-yl)-1-propanal | 934967-92-7

• 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: 3-(2-{[methyl(5,6,7,8-tetrahydro-8-quinolinyl)amino]methyl}-1H-benzimidazol-4-yl)-1-propanal
• 英文别名: 3-(2-{[Methyl(5,6,7,8-tetrahydro-8-quinolinyl)amino]methyl}-1H-benzimidazol-4-yl)propanal；3-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1H-benzimidazol-4-yl]propanal
• CAS: 934967-92-7
• 化学式: C₂₁H₂₄N₄O
• 分子量: 348.448
• InChiKey: MELVUNWTHBEXFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-{[methyl(5,6,7,8-tetrahydro-8-quinolinyl)amino]methyl}-1H-benzimidazol-4-yl)-1-propanal 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以13%的产率得到N-{[4-(3-aminopropyl)-1H-benzimidazol-2-yl]methyl}-N-methyl-5,6,7,8-tetrahydro-8-quinolinamine
  参考文献：
  名称：

  Amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1

  摘要：

  Several novel amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines were synthesized which had potent activity against HIV-1. The synthetic approaches adopted allowed for variation of the substitution pattern and resulting changes in antiviral activity are highlighted. This led to the identification of compounds with low and sub-nanomolar anti-HIV-1 activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.037
• 作为产物：
  描述：

  3-(2-{[methyl(5,6,7,8-tetrahydro-8-quinolinyl)amino]methyl}-1H-benzimidazol-4-yl)-1-propanol 在 IBX polystyrene 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-(2-{[methyl(5,6,7,8-tetrahydro-8-quinolinyl)amino]methyl}-1H-benzimidazol-4-yl)-1-propanal
  参考文献：
  名称：

  [EN] CHEMICAL COMPOUNDS
  [FR] COMPOSES CHIMIQUES

  摘要：

  公开号：

  WO2006023400A3

文献信息

• Chemical Compounds
  申请人：Gudmundsson Kristjan

  公开号：US20080045537A1

  公开（公告）日：2008-02-21

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

  本发明提供了一种化合物，可以通过结合趋化因子受体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：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1789045A2

  公开（公告）日：2007-05-30
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006023400A3

  公开（公告）日：2006-06-08
• Amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1
  作者：Kristjan S. Gudmundsson、Paul R. Sebahar、Leah D’Aurora Richardson、John F. Miller、Elizabeth M. Turner、John G. Catalano、Andrew Spaltenstein、Wendell Lawrence、Michael Thomson、Stephen Jenkinson

  DOI：10.1016/j.bmcl.2009.07.037

  日期：2009.9

  Several novel amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines were synthesized which had potent activity against HIV-1. The synthetic approaches adopted allowed for variation of the substitution pattern and resulting changes in antiviral activity are highlighted. This led to the identification of compounds with low and sub-nanomolar anti-HIV-1 activity. (C) 2009 Elsevier Ltd. All rights reserved.