tert-butyl 2-(((2-cyano-4-(methoxycarbonyl)benzyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-1H-benzo[d]imidazole-1-carboxylate | 421551-54-4

• 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: tert-butyl 2-(((2-cyano-4-(methoxycarbonyl)benzyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-1H-benzo[d]imidazole-1-carboxylate
• 英文别名: 2-{[(2-Cyano-4-methoxycarbonyl-benzyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester；tert-butyl 2-[[(2-cyano-4-methoxycarbonylphenyl)methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazole-1-carboxylate
• CAS: 421551-54-4
• 化学式: C₃₂H₃₃N₅O₄
• 分子量: 551.645
• InChiKey: ITAGXQXARAISQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(((2-cyano-4-(methoxycarbonyl)benzyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-1H-benzo[d]imidazole-1-carboxylate 在 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 tert-butyl 2-(((2-aminomethyl-4-(methoxycarbonyl)benzyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-1H-benzo[d]imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis and SAR of novel CXCR4 antagonists that are potent inhibitors of T tropic (X4) HIV-1 replication

  摘要：

  An early lead from the AMD070 program was optimized and a structure-activity relationship was developed for a novel series of heterocyclic containing compounds. Potent CXCR4 antagonists were identified based on anti-HIV-1 activity and Ca(2+) flux inhibition that displayed good pharmacokinetics in rat and dog. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.023
• 作为产物：
  描述：

  tert-butyl 2-((5,6,7,8-tetrahydroquinolin-8-ylamino)methyl)-1H-benzo[d]imidazole-1-carboxylate 、 4-(溴甲基)-3-氰基苯甲酸甲酯 在 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以98%的产率得到tert-butyl 2-(((2-cyano-4-(methoxycarbonyl)benzyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-1H-benzo[d]imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis and SAR of novel CXCR4 antagonists that are potent inhibitors of T tropic (X4) HIV-1 replication

  摘要：

  An early lead from the AMD070 program was optimized and a structure-activity relationship was developed for a novel series of heterocyclic containing compounds. Potent CXCR4 antagonists were identified based on anti-HIV-1 activity and Ca(2+) flux inhibition that displayed good pharmacokinetics in rat and dog. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.023

文献信息

• Chemokine receptor binding heterocyclic compounds
  申请人：——

  公开号：US20030028022A1

  公开（公告）日：2003-02-06

  Compounds which modulate chemokine receptor activities are disclosed. These compounds are preferably tertiary amines comprising tetrahydroquinoline and benzimidazole.

  本发明揭示了调节趋化因子受体活性的化合物。这些化合物通常为包含四氢喹啉和苯并咪唑的三级胺。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS
  申请人：ANORMED INC.

  公开号：EP1317451A1

  公开（公告）日：2003-06-11
• US6734191B2
  申请人：——

  公开号：US6734191B2

  公开（公告）日：2004-05-11
• US7091217B2
  申请人：——

  公开号：US7091217B2

  公开（公告）日：2006-08-15
• US7807694B2
  申请人：——

  公开号：US7807694B2

  公开（公告）日：2010-10-05