3-({Methyl[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino}methyl)isoquinoline-4-carbonitrile | 1228073-42-4

• 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: 3-({Methyl[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino}methyl)isoquinoline-4-carbonitrile
• 英文别名: 3-[[methyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]isoquinoline-4-carbonitrile
• CAS: 1228073-42-4
• 化学式: C₂₁H₂₀N₄
• 分子量: 328.417
• InChiKey: JHBTXBYZKXAZBG-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-({Methyl[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino}methyl)isoquinoline-4-carbonitrile 在 氨 、 氢气 作用下， 以 甲醇 为溶剂， 以53%的产率得到(8S)-N-[[4-(aminomethyl)-3-isoquinolyl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine
  参考文献：
  名称：

  Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity

  摘要：

  Using AMD070 as a starting point for structural modification, a novel series of isoquinoline CXCR4 antagonists was developed. A structure-activity scan of alternate lower heterocycles led to the 3-isoquinolinyl moiety as an attractive replacement for benzimidazole. Side chain optimization in the isoquinoline series led to a number of compounds with low nanomolar anti-HIV activities and promising rat PK properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.118
• 作为产物：
  描述：

  3-bromomethyl-4-cyano-isoquinoline 、 (S)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到3-({Methyl[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino}methyl)isoquinoline-4-carbonitrile
  参考文献：
  名称：

  Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity

  摘要：

  Using AMD070 as a starting point for structural modification, a novel series of isoquinoline CXCR4 antagonists was developed. A structure-activity scan of alternate lower heterocycles led to the 3-isoquinolinyl moiety as an attractive replacement for benzimidazole. Side chain optimization in the isoquinoline series led to a number of compounds with low nanomolar anti-HIV activities and promising rat PK properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.118

文献信息

• Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity
  作者：John F. Miller、Kristjan S. Gudmundsson、Leah D’Aurora Richardson、Stephen Jenkinson、Andrew Spaltenstein、Michael Thomson、Pat Wheelan

  DOI：10.1016/j.bmcl.2010.03.118

  日期：2010.5

  Using AMD070 as a starting point for structural modification, a novel series of isoquinoline CXCR4 antagonists was developed. A structure-activity scan of alternate lower heterocycles led to the 3-isoquinolinyl moiety as an attractive replacement for benzimidazole. Side chain optimization in the isoquinoline series led to a number of compounds with low nanomolar anti-HIV activities and promising rat PK properties. (C) 2010 Elsevier Ltd. All rights reserved.