(8S)-N-[[4-(3-aminopropyl)-3-isoquinolyl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine | 1228073-63-9

• 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: (8S)-N-[[4-(3-aminopropyl)-3-isoquinolyl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine
• 英文别名: (8S)-N-[[4-(3-aminopropyl)isoquinolin-3-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine
• CAS: 1228073-63-9
• 化学式: C₂₃H₂₈N₄
• 分子量: 360.502
• InChiKey: UHUJJNZHSVYANG-QFIPXVFZSA-N

物化性质

• 沸点：
  553.0±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (8S)-N-[[4-(3-aminopropyl)-3-isoquinolyl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine 在 三乙酰氧基硼氢化钠 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以81%的产率得到(S)-N-((4-(3-(dimethylamino)propyl)isoquinolin-3-yl)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-[3-({Methyl[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino}methyl)isoquinolin-4-yl]propanenitrile 在 氨 、 氢气 作用下， 以 甲醇 为溶剂， 以70%的产率得到(8S)-N-[[4-(3-aminopropyl)-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

文献信息

• Small-Molecule Fluorescent Ligands for the CXCR4 Chemokine Receptor
  作者：Sebastian Dekkers、Birgit Caspar、Joëlle Goulding、Nicholas D. Kindon、Laura E. Kilpatrick、Leigh A. Stoddart、Stephen J. Briddon、Barrie Kellam、Stephen J. Hill、Michael J. Stocks

  DOI：10.1021/acs.jmedchem.3c00151

  日期：——

  The C–X–C chemokine receptor type 4, or CXCR4, is a chemokine receptor found to promote cancer progression and metastasis of various cancer cell types. To investigate the pharmacology of this receptor, and to further elucidate its role in cancer, novel chemical tools are a necessity. In the present study, using classic medicinal chemistry approaches, small-molecule-based fluorescent probes were designed

  C–X–C 趋化因子受体 4 型或 CXCR4 是一种趋化因子受体，被发现可促进各种癌细胞类型的癌症进展和转移。为了研究这种受体的药理学，并进一步阐明它在癌症中的作用，需要新的化学工具。在本研究中，使用经典的药物化学方法，基于先前报道的小分子拮抗剂设计并合成了基于小分子的荧光探针。在这里，我们报告了三种不同化学类别的荧光探针的开发，这些荧光探针在基于荧光的新型 NanoBRET 结合测定中显示出与 CXCR4 受体的特异性结合（p K D范围 6.6–7.1)。由于它们在 CXCR4 上保留了亲和力，我们进一步报告了它们在竞争结合实验和共聚焦显微镜中的用途，以研究该受体的药理学和细胞分布。
• 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.