2-Nonyl-3-prop-2-ynyl-imidazo[4,5-c]quinoline | 1314034-72-4

• 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: 2-Nonyl-3-prop-2-ynyl-imidazo[4,5-c]quinoline
• 英文别名: 2-nonyl-3-prop-2-ynylimidazo[4,5-c]quinoline
• CAS: 1314034-72-4
• 化学式: C₂₂H₂₇N₃
• 分子量: 333.476
• InChiKey: INUKZKUSPNQTEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二氨基喹啉 在 磷酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 2-Nonyl-3-prop-2-ynyl-imidazo[4,5-c]quinoline
  参考文献：
  名称：

  Preliminary evaluation of a 3H imidazoquinoline library as dual TLR7/TLR8 antagonists

  摘要：

  Toll-like receptors (TLR) -7 and -8 are thought to play an important role in immune activation processes underlying the pathophysiology of HIV and several clinically important autoimmune diseases. Based on our earlier findings of TLR7-antagonistic activity in a 3H imidazoquinoline, we sought to examine a pilot library of 3H imidazoquinolines for dual TLR7/8 antagonists, since they remain a poorly explored chemotype. 2D-NOE experiments were employed to unequivocally characterize the compounds. A quinolinium compound 12, bearing p-methoxybenzyl substituents on N3 and N5 positions was identified as a lead. Compound 12 was found to inhibit both TLR7 and TLR8 at low micromolar concentrations. Our preliminary results suggest that alkylation with electron-rich substituents on the quinoline N5, or conversely, elimination of the fixed charge of the resultant quaternary amine on the quinolinium may yield more active compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.052

文献信息

• Preliminary evaluation of a 3H imidazoquinoline library as dual TLR7/TLR8 antagonists
  作者：Nikunj M. Shukla、Subbalakshmi S. Malladi、Victor Day、Sunil A. David

  DOI：10.1016/j.bmc.2011.04.052

  日期：2011.6

  Toll-like receptors (TLR) -7 and -8 are thought to play an important role in immune activation processes underlying the pathophysiology of HIV and several clinically important autoimmune diseases. Based on our earlier findings of TLR7-antagonistic activity in a 3H imidazoquinoline, we sought to examine a pilot library of 3H imidazoquinolines for dual TLR7/8 antagonists, since they remain a poorly explored chemotype. 2D-NOE experiments were employed to unequivocally characterize the compounds. A quinolinium compound 12, bearing p-methoxybenzyl substituents on N3 and N5 positions was identified as a lead. Compound 12 was found to inhibit both TLR7 and TLR8 at low micromolar concentrations. Our preliminary results suggest that alkylation with electron-rich substituents on the quinoline N5, or conversely, elimination of the fixed charge of the resultant quaternary amine on the quinolinium may yield more active compounds. (C) 2011 Elsevier Ltd. All rights reserved.