1,1-dimethylethyl 4-[2-(aminomethyl)-1H-benzimidazol-4-yl]-1-piperazinecarboxylate | 1190854-33-1

• 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: 1,1-dimethylethyl 4-[2-(aminomethyl)-1H-benzimidazol-4-yl]-1-piperazinecarboxylate
• 英文别名: tert-butyl 4-[2-(aminomethyl)-1H-benzimidazol-4-yl]piperazine-1-carboxylate
• CAS: 1190854-33-1
• 化学式: C₁₇H₂₅N₅O₂
• 分子量: 331.418
• InChiKey: VLPUSAKFCHJKTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-二氢-5H-喹啉-8-酮 、 1,1-dimethylethyl 4-[2-(aminomethyl)-1H-benzimidazol-4-yl]-1-piperazinecarboxylate 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 tert-butyl 4-(2-(((5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-1H-benzo[d]imidazol-4-yl)piperazine-1-carboxylate
  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：

  1,1-dimethylethyl 4-{2-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1H-benzimidazol-4-yl}-1-piperazinecarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以99%的产率得到1,1-dimethylethyl 4-[2-(aminomethyl)-1H-benzimidazol-4-yl]-1-piperazinecarboxylate
  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

文献信息

• Chemical Compounds
  申请人：Gudmundsson Kristjan

  公开号：US20080214562A1

  公开（公告）日：2008-09-04

  The present invention provides 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.

  本发明提供了一些化合物，这些化合物以与趋化因子受体结合的方式对目标细胞表现出对HIV感染的保护效果，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。
• 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.