3-amino-4-benzamidopyridine | 918550-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-4-benzamidopyridine
• 英文别名: N-(3-aminopyridin-4-yl)benzamide
• CAS: 918550-20-6
• 化学式: C₁₂H₁₁N₃O
• mdl: MFCD17153917
• 分子量: 213.239
• InChiKey: SZLOJKOWPMPOBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4-benzamidopyridine 在 tetrafluoroboric acid 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以100%的产率得到
  参考文献：
  名称：

  1 H -1,2,3-三唑并-[4,5- c ]吡啶的N-酰基和N-烷氧基羰基衍生物；制备及应用

  摘要：

  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。

  DOI：

  10.1002/jhet.5570430223
• 作为产物：
  描述：

  N1-(4-吡啶基)苯甲酰胺 在 palladium on activated charcoal 氢气 、 五氧化二氮 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 为溶剂， 20.0 ℃ 、700.0 kPa 条件下， 反应 21.5h， 生成 3-amino-4-benzamidopyridine
  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

• Synthesis of alkylsulfinyl substituted 2-phenylimidazo [4,5-c] pyridines
  申请人：ELI LILLY AND COMPANY

  公开号：EP0266897A1

  公开（公告）日：1988-05-11

  The present invention provides a process for preparing an alkylsulfinyl 2- phenylimidazo[4,5-c]pyridine of the formulae or wherein: R¹ is hydrogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, or halogen; R³ is C₁-C₄ alkylsulfinyl in either the 2ʹ, 4ʹ, or 6ʹ position; R² and R⁴ independently are hydrogen, hydroxy, halo, cyano, trifluoromethyl, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₂-C₄ alkenyloxy, C₂-C₄ alkynyloxy, C₁-C₄ hydroxy-alkyloxy, cyanomethoxy, amino, mono- or di-C₁-C₄ alkylamino, comprising reacting an N-(3-amino-4-pyridinyl)alkylthiobenzamide of the formula wherein: R¹, R² and R⁴ are as defined above; and R⁵ is a C₁-C₄ alkylthio in either the 2ʹ, 4ʹ, or 6ʹ-position, with an oxidizing agent in a lower alkanoic acid solvent at a temperature of about -20°C to about 50°C.

  本发明提供了一种制备 2-苯基咪唑并[4,5-c]吡啶的烷基亚磺酰基的工艺，其式为 或 其中 R¹ 是氢、C₁-C₄ 烷基、C₁-C₄ 烷氧基或卤素； R³ 是位于 2ʹ、4ʹ或 6ʹ位的 C₁-C₄烷基亚磺酰基； R² 和 R⁴ 分别为氢、羟基、卤代、氰基、三氟甲基、C₁-C₄ 烷基、C₁-C₄ 烷氧基、C₂-C₄烯氧基、C₂-C₄炔氧基、C₁-C₄羟基烷氧基、氰基甲氧基、氨基、单-或双-C₁-C₄烷基氨基、 包括使 N-(3-氨基-4-吡啶基)烷基硫代苯甲酰胺反应，其式为 其中 R¹、R² 和 R⁴ 如上定义；和 R⁵是2ʹ、4ʹ或6ʹ位的C₁-C₄烷硫基，在低级烷酸溶剂中与氧化剂在约-20℃至约50℃的温度下反应。
• 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.
• US4740599A
  申请人：——

  公开号：US4740599A

  公开（公告）日：1988-04-26
• US7256287B2
  申请人：——

  公开号：US7256287B2

  公开（公告）日：2007-08-14
• <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。