3-氨基-4-乙酰氨基吡啶 | 145255-15-8

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-氨基-4-乙酰氨基吡啶
• 中文别名: 4-乙酰氨基-3-氨基吡啶
• 英文名称: N-(3-aminopyridin-4-yl)acetamide
• 英文别名: 4-acetylamino-3-aminopyridine；4-acetamido-3-aminopyridine；3-Amino-4-acetylaminopyridine
• CAS: 145255-15-8
• 化学式: C₇H₉N₃O
• mdl: MFCD08235180
• 分子量: 151.168
• InChiKey: NAAZXRDKBDXLMS-UHFFFAOYSA-N

物化性质

• 沸点：
  429.2±30.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S28,S36/37/39,S45
• 危险类别码：
  R25,R26,R36/37/38
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-氨基-4-乙酰氨基吡啶 在 溶剂黄146 作用下， 反应 1.5h， 以97%的产率得到2-甲基咪唑[4,5-C]吡啶
  参考文献：
  名称：

  通过4-酰基氨基吡啶的硝化合成3,4-二氨基吡啶和咪唑并[4,5- c ]吡啶

  摘要：

  探索了基于4-酰基氨基吡啶3a，3b直接硝化制备3,4-二氨基吡啶（5）和咪唑并[4,5- c ]吡啶7a，7b的新方法。

  DOI：

  10.1002/jhet.5570360505
• 作为产物：
  描述：

  4-乙酰氨基-3-硝基吡啶 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、700.0 kPa 条件下， 反应 23.0h， 以97%的产率得到3-氨基-4-乙酰氨基吡啶
  参考文献：
  名称：

  通过4-酰基氨基吡啶的硝化合成3,4-二氨基吡啶和咪唑并[4,5- c ]吡啶

  摘要：

  探索了基于4-酰基氨基吡啶3a，3b直接硝化制备3,4-二氨基吡啶（5）和咪唑并[4,5- c ]吡啶7a，7b的新方法。

  DOI：

  10.1002/jhet.5570360505

文献信息

• <i>N</i>-acyl and<i>N</i>-alkoxycarbonyl derivatives of 1<i>H</i>-1,2,3-triazolo-[4,5-<i>c</i>]pyridine; Preparation and application
  作者：Jarle Holt、Anne Fiksdahl

  DOI：10.1002/jhet.5570430223

  日期：2006.3

  The synthetic transformations are facilitated by the one-pot preparation of 1a-e followed by the direct reaction with the amines or amino acid. The present method thus offers an efficient and convenient protocol for the in situ preparation of triazolopyridine reagents to be used directly for the protection of amines and amino acids. N-Acyl- and N-alkoxycarbonyl triazolopyridines (1a-e) were readily prepared

  研究了N-取代的1,2,3-三唑并[4,5- c ]吡啶1a-e的N-酰化和N-烷氧羰基化能力。易于制备烷氧基羰基三唑并吡啶衍生物（1c-e），产率为81-96％（相应的四氟硼酸酯> 95％）。通过形成氨基和氨基甲酸酯保护的伯胺衍生物，已证明三唑并[4，5- c ]吡啶（1）可作为良好的离去基团。该方法对于N-叔丁氧羰基（N-BOC）保护氨基酸，苯丙氨酸。一锅制备1a-e，然后与胺或氨基酸直接反应，可促进合成转化。因此，本方法提供了用于原位制备直接用于保护胺和氨基酸的三唑并吡啶试剂的有效且方便的方案。N-酰基和N-烷氧基羰基三唑并吡啶（1a-e）可以通过胺保护，吡啶硝化，硝基还原和重氮化/环化从4-氨基吡啶（4）分四步轻松制备。所有反应都在非常温和的条件下提供了高产率快速转化的优点。
• Aminopyridine compounds
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0503627A1

  公开（公告）日：1992-09-16

  An aminopyridine compound represented by the formula: wherein n represents 0 or 1; Z represents =S, =O, =NCN or =CHNO₂; R₁ represents -CN, -NR₃R₄, -CONR₃R₄, -NHNR₃R₄, -NHCONHR₃, -NHSO₂R₃ or -SR₃; R₂ represents H, or substituted or unsubstituted alkyl; R₃ and R₄, which may be the same or different, represent H, substituted or unsubstituted alkyl, aryl, substituted or unsubstituted acyl or alkoxycarbonyl group; and R₃ and R₄ may form a heterocyclic ring together with a nitrogen atom to which R₃ and R₄ are bound, through another heteroatom or without it; or an acid salt thereof, which is excellent in pharmacological effect and repressed in side effects as a drug for circulatory diseases.

  一种由式表示的氨基吡啶化合物： 其中 n 代表 0 或 1；Z 代表 =S、=O、=NCN 或 =CHNO₂；R₁ 代表 -CN、-NR₃R₄、-CONR₃R₄、-NHNR₃R₄、-NHCONHR₃、-NHSO₂R₃ 或 -SR₃； R₂ 代表 H、取代或未取代的烷基； R₃ 和 R₄ 可以相同或不同，代表 H、取代或未取代的烷基、芳基、取代或未取代的酰基或烷氧基羰基； R₃ 和 R₄ 可以通过另一个杂原子或不通过另一个杂原子与 R₃ 和 R₄ 所结合的氮原子一起形成一个杂环；或其酸盐，作为治疗循环系统疾病的药物，药理作用优异，副作用小。
• 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.
• Rasala, D., Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84
  作者：Rasala, D.

  DOI：——

  日期：——
• US5262415A
  申请人：——

  公开号：US5262415A

  公开（公告）日：1993-11-16