3-nitropyridine-4-carbonyl azide | 852102-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-nitropyridine-4-carbonyl azide
• 英文别名: 3-nitroisonicotinoyl azide
• CAS: 852102-17-1
• 化学式: C₆H₃N₅O₃
• 分子量: 193.122
• InChiKey: AGUPRCWYYCVQBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitropyridine-4-carbonyl azide 以 苯 为溶剂， 生成 3-nitropyridin-4-yl isocyanate
  参考文献：
  名称：

  异亚硝基吡啶基酯

  摘要：

  我们在此报告异氰酸3-3-硝基-4-吡啶基酯9和异氰酸5-硝基-2-吡啶基酯18的首次制备。它们是由相应的酰基叠氮化物的Curtius重排而形成8和17，从3-硝基-4-吡啶羧酸甲酯制备6 经由酰肼7和5-硝基-吡啶甲酸16分别。通过硝化4-吡啶甲酸甲酯5和硝化并氧化2-甲基吡啶14来生成底物6和16。3-硝基-4-吡啶基异氰酸酯9可以保存在干燥溶液中，并且在室温下稳定数周，而5-硝基-2-吡啶基异氰酸酯18的稳定性较差，应立即用于合成目的。

  DOI：

  10.1002/jhet.5570420213
• 作为产物：
  描述：

  3-nitropyridine-4-carbonylhydrazide 在 sodium nitrite 作用下， 生成 3-nitropyridine-4-carbonyl azide
  参考文献：
  名称：

  异亚硝基吡啶基酯

  摘要：

  我们在此报告异氰酸3-3-硝基-4-吡啶基酯9和异氰酸5-硝基-2-吡啶基酯18的首次制备。它们是由相应的酰基叠氮化物的Curtius重排而形成8和17，从3-硝基-4-吡啶羧酸甲酯制备6 经由酰肼7和5-硝基-吡啶甲酸16分别。通过硝化4-吡啶甲酸甲酯5和硝化并氧化2-甲基吡啶14来生成底物6和16。3-硝基-4-吡啶基异氰酸酯9可以保存在干燥溶液中，并且在室温下稳定数周，而5-硝基-2-吡啶基异氰酸酯18的稳定性较差，应立即用于合成目的。

  DOI：

  10.1002/jhet.5570420213

文献信息

• Formulating a new basis for the treatment against botulinum neurotoxin intoxication: 3,4-Diaminopyridine prodrug design and characterization
  作者：Joseph S. Zakhari、Isao Kinoyama、Mark S. Hixon、Antonia Di Mola、Daniel Globisch、Kim D. Janda

  DOI：10.1016/j.bmc.2011.09.019

  日期：2011.11

  Botulism is a disease characterized by neuromuscular paralysis and is produced from botulinum neurotoxins (BoNTs) found within the Gram positive bacterium Clostridium botulinum. This bacteria produces the most deadliest toxin known, with lethal doses as low as 1 ng/kg. Due to the relative ease of production and transport, the use of these agents as potential bioterrorist weapons has become of utmost concern. No small molecule therapies against BoNT intoxication have been approved to date. However, 3,4-diaminopyridine (3,4-DAP), a potent reversible inhibitor of voltage-gated potassium channels, is an effective cholinergic agonist used in the treatment of neuromuscular degenerative disorders that require cholinergic enhancement. 3,4-DAP has also been shown to facilitate recovery of neuromuscular action potential post botulinum intoxication by blocking K(+) channels. Unfortunately, 3,4-DAP displays toxicity largely due to blood-brain-barrier (BBB) penetration. As a dual-action prodrug approach to cholinergic enhancement we have designed carbamate and amide conjugates of 3,4-DAP. The carbamate prodrug is intended to be a slowly reversible inhibitor of acetylcholinesterase (AChE) along the lines of the stigmines thereby allowing increased persistence of released acetylcholine within the synaptic cleft. As a secondary activity, cleavage of the carbamate prodrug by AChE will afford the localized release of 3,4-DAP, which in turn, will enhance the pre-synaptic release of additional acetylcholine. Being a competitive inhibitor with respect to acetylcholine, the activity of the prodrug will be greatest at the synaptic junctions most depleted of acetylcholine. Here we report upon the synthesis and biochemical characterization of three new classes of prodrugs intended to limit previously reported stability and toxicity issues. Of the prodrugs examined, compound 32, demonstrated the most clinically relevant half-life of 2.76 h, while selectively inhibiting AChE over butyrylcholinesterase-a plasma-based high activity esterase. Future in vivo studies could provide validation of prodrug 32 as a potential treatment against BoNT intoxication as well as other neuromuscular disorders. (C) 2011 Elsevier Ltd. All rights reserved.
• Nitropyridyl isocyanates
  作者：Jarle Holt、Trygve Andreassen、Jan M. Bakke、Anne Fiksdahl

  DOI：10.1002/jhet.5570420213

  日期：2005.3

  the first preparation of 3-nitro-4-pyridyl isocyanate 9 and 5-nitro-2-pyridyl isocyanate 18. They were formed by Curtius rearrangement of the corresponding acyl azides 8 and 17, prepared from methyl 3-nitro-4-pyridinecarboxylate 6 via the hydrazide 7 and 5-nitro-picolinic acid 16, respectively. The substrates 6 and 16 were generated by nitration of methyl 4-pyridinecarboxylate 5 and nitration and oxidation

  我们在此报告异氰酸3-3-硝基-4-吡啶基酯9和异氰酸5-硝基-2-吡啶基酯18的首次制备。它们是由相应的酰基叠氮化物的Curtius重排而形成8和17，从3-硝基-4-吡啶羧酸甲酯制备6 经由酰肼7和5-硝基-吡啶甲酸16分别。通过硝化4-吡啶甲酸甲酯5和硝化并氧化2-甲基吡啶14来生成底物6和16。3-硝基-4-吡啶基异氰酸酯9可以保存在干燥溶液中，并且在室温下稳定数周，而5-硝基-2-吡啶基异氰酸酯18的稳定性较差，应立即用于合成目的。