4-azido-3-nitroquinoline

• 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: 4-azido-3-nitroquinoline
• 英文别名: 3-Nitro-4-azidoquinoline
• 化学式: C₉H₅N₅O₂
• 分子量: 215.171
• InChiKey: BJVPBGYNTPQSSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-azido-3-nitroquinoline 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以700 mg的产率得到3,4-二氨基喹啉
  参考文献：
  名称：

  Regioisomerism-dependent TLR7 agonism and antagonism in an imidazoquinoline

  摘要：

  Chronic immune activation is a hallmark of progressive HIV infection. Recent reports point to the engagement of toll-like receptor 7 (TLR7) and -9 by viral RNA as contributing to the activation of innate immune responses, which drive viral replication leading to immune exhaustion. The only known class of TLR7 antagonists is single-stranded phosphorothioate oligonucleotides, which has been demonstrated to inhibit immune activation in human and Rhesus macaque in vitro models. The availability of a selective and potent small-molecule TLR7 antagonist should allow the evaluation of potential benefits of suppression of TLR7-mediated immune activation in HIV/AIDS. Gardiquimod is a known N-1-substituted 1H-imidazoquinoline TLR7 agonist, the synthesis of which has not been published. We show that the 3H regioisomer is completely inactive as a TLR7 agonist and is weakly antagonistic. A des-amino precursor of the 3H regioisomer is more potent as a TLR7 antagonist, with an IC50 value of 7.5 mu M. This class of compound may serve as a starting point for the development of small-molecule inhibitors of TLR7. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.100
• 作为产物：
  描述：

  4-氯-3-硝基喹啉 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以77%的产率得到4-azido-3-nitroquinoline
  参考文献：
  名称：

  Dyall, Leonard K.; Wah, Wong Ming, Australian Journal of Chemistry, 1985, vol. 38, # 7, p. 1045 - 1059

  摘要：

  DOI：

文献信息

• Dyall, Leonard K.; Wah, Wong Ming, Australian Journal of Chemistry, 1985, vol. 38, # 7, p. 1045 - 1059
  作者：Dyall, Leonard K.、Wah, Wong Ming

  DOI：——

  日期：——
• Regioisomerism-dependent TLR7 agonism and antagonism in an imidazoquinoline
  作者：Nikunj M. Shukla、Matthew R. Kimbrell、Subbalakshmi S. Malladi、Sunil A. David

  DOI：10.1016/j.bmcl.2009.02.100

  日期：2009.4

  Chronic immune activation is a hallmark of progressive HIV infection. Recent reports point to the engagement of toll-like receptor 7 (TLR7) and -9 by viral RNA as contributing to the activation of innate immune responses, which drive viral replication leading to immune exhaustion. The only known class of TLR7 antagonists is single-stranded phosphorothioate oligonucleotides, which has been demonstrated to inhibit immune activation in human and Rhesus macaque in vitro models. The availability of a selective and potent small-molecule TLR7 antagonist should allow the evaluation of potential benefits of suppression of TLR7-mediated immune activation in HIV/AIDS. Gardiquimod is a known N-1-substituted 1H-imidazoquinoline TLR7 agonist, the synthesis of which has not been published. We show that the 3H regioisomer is completely inactive as a TLR7 agonist and is weakly antagonistic. A des-amino precursor of the 3H regioisomer is more potent as a TLR7 antagonist, with an IC50 value of 7.5 mu M. This class of compound may serve as a starting point for the development of small-molecule inhibitors of TLR7. (c) 2009 Elsevier Ltd. All rights reserved.