5-fluoro-2-nitro-N-(pyridin-2-ylmethyl)aniline | 1322565-00-3

• 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: 5-fluoro-2-nitro-N-(pyridin-2-ylmethyl)aniline
• CAS: 1322565-00-3
• 化学式: C₁₂H₁₀FN₃O₂
• mdl: MFCD17062187
• 分子量: 247.229
• InChiKey: QKRGXLRRCKBVNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-nitro-N-(pyridin-2-ylmethyl)aniline 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 4-fluoro-2-N-(pyridin-2-ylmethyl)benzene-1,2-diamine
  参考文献：
  名称：

  Synthesis of Mono- and Di-fluorinated Benzimidazoles

  摘要：

  AbstractThree efficient methods to synthesize mono‐ and di‐fluorinated benzimidazoles are reported. These methods provide 5‐amino‐6‐fluoro‐benzimidazoles (5), 5,7‐difluoro‐benzimidazoles (10), and 6‐fluoro‐benzimidazoles (13) starting from commercially available 1,5‐difluoro‐2,4‐dinitrobenzene (DFDNB), 2,3,4,5‐tetrafluoro‐6‐nitrobenzoic acid (TFNBA), and 2,4‐difluoro‐1‐nitrobenzene (DFNB), respectively.

  DOI：

  10.1002/cjoc.201190200
• 作为产物：
  描述：

  2-氨甲基吡啶 、 2,4-二氟硝基苯 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成 5-fluoro-2-nitro-N-(pyridin-2-ylmethyl)aniline
  参考文献：
  名称：

  发现和表征2-硝基-5-（4-（苯磺酰基）哌嗪-1-基）-N-（吡啶-4-基甲基）苯胺作为埃及伊蚊Kir1（AeKir1）通道的新型抑制剂。

  摘要：

  蚊子传播的虫媒病毒疾病，例如寨卡病毒，登革热和基孔肯雅热，是由感染的成年雌性埃及伊蚊传播给人类的，并影响了世界上很大一部分人口。Ae的Kir1频道。aegypti（AeKir1）是蚊子Malpighian（肾）肾小管功能中的重要离子通道，可以对其进行操纵以破坏蚊子的排泄功能。先前我们已经报道了针对AeKir1通道活跃的各种支架的发现。在这里，我们报告了作为AeKir1抑制剂的新型2-硝基-5-（4-（苯磺酰基）哌嗪-1-基）-N-（吡啶-4-基甲基）苯胺支架的合成和生物学特性。与以前报道的支架相比，这种新型支架在体外更有效，并且该分子可杀死蚊子幼虫。

  DOI：

  10.1021/acsinfecdis.8b00368

文献信息

• Benzimidazole derivatives useful as CB-1 inverse agonists
  申请人：Janssen Pharmaceutica NV

  公开号：US10118900B2

  公开（公告）日：2018-11-06

  The present invention is directed to benzimidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions mediated by the CB-1 receptor; more particularly, use in the treatment of disorders and conditions responsive to inverse agonism of the CB-1 receptor. More particularly, the compounds of the present invention are useful in the treatment of metabolic disorders.

  本发明涉及苯并咪唑衍生物、含有苯并咪唑衍生物的药物组合物及其在治疗由 CB-1 受体介导的紊乱和病症中的用途；更具体地说，是在治疗对 CB-1 受体的反向激动有反应的紊乱和病症中的用途。更具体地说，本发明的化合物可用于治疗代谢紊乱。
• BENZIMIDAZOLE DERIVATIVES USEFUL AS CB-1 INVERSE AGONISTS
  申请人：Janssen Pharmaceutica NV

  公开号：US20170057929A1

  公开（公告）日：2017-03-02

  The present invention is directed to benzimidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions mediated by the CB-1 receptor; more particularly, use in the treatment of disorders and conditions responsive to inverse agonism of the CB-1 receptor. More particularly, the compounds of the present invention are useful in the treatment of metabolic disorders.
• [EN] BENZIMIDAZOLE DERIVATIVES USEFUL AS CB-1 INVERSE AGONISTS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE UTILES À TITRE D'AGONISTES INVERSES DE CB-1
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2017035114A1

  公开（公告）日：2017-03-02

  The present invention is directed to benzimidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions mediated by the CB-1 receptor; more particularly, use in the treatment of disorders and conditions responsive to inverse agonism of the CB-1 receptor. More particularly, the compounds of the present invention are useful in the treatment of metabolic disorders.
• Discovery and Characterization of 2-Nitro-5-(4-(phenylsulfonyl)piperazin-1-yl)-<i>N</i>-(pyridin-4-ylmethyl)anilines as Novel Inhibitors of the <i>Aedes aegypti</i> Kir1 (<i>Ae</i>Kir1) Channel
  作者：Christopher D. Aretz、M. Jane Morwitzer、Austin G. Sanford、Alicia M. Hogan、Madelene V. Portillo、Sujay V. Kharade、Meghan Kramer、James B. McCarthey、Renata Rusconi Trigueros、Peter M. Piermarini、Jerod S. Denton、Corey R. Hopkins

  DOI：10.1021/acsinfecdis.8b00368

  日期：2019.6.14

  infected adult female Aedes aegypti mosquitoes and affect a large portion of the world's population. The Kir1 channel in Ae. aegypti ( AeKir1) is an important ion channel in the functioning of mosquito Malpighian (renal) tubules and one that can be manipulated in order to disrupt excretory functions in mosquitoes. We have previously reported the discovery of various scaffolds that are active against

  蚊子传播的虫媒病毒疾病，例如寨卡病毒，登革热和基孔肯雅热，是由感染的成年雌性埃及伊蚊传播给人类的，并影响了世界上很大一部分人口。Ae的Kir1频道。aegypti（AeKir1）是蚊子Malpighian（肾）肾小管功能中的重要离子通道，可以对其进行操纵以破坏蚊子的排泄功能。先前我们已经报道了针对AeKir1通道活跃的各种支架的发现。在这里，我们报告了作为AeKir1抑制剂的新型2-硝基-5-（4-（苯磺酰基）哌嗪-1-基）-N-（吡啶-4-基甲基）苯胺支架的合成和生物学特性。与以前报道的支架相比，这种新型支架在体外更有效，并且该分子可杀死蚊子幼虫。
• Synthesis of Mono- and Di-fluorinated Benzimidazoles
  作者：Wu Liang、Gang Liu

  DOI：10.1002/cjoc.201190200

  日期：2011.5

  AbstractThree efficient methods to synthesize mono‐ and di‐fluorinated benzimidazoles are reported. These methods provide 5‐amino‐6‐fluoro‐benzimidazoles (5), 5,7‐difluoro‐benzimidazoles (10), and 6‐fluoro‐benzimidazoles (13) starting from commercially available 1,5‐difluoro‐2,4‐dinitrobenzene (DFDNB), 2,3,4,5‐tetrafluoro‐6‐nitrobenzoic acid (TFNBA), and 2,4‐difluoro‐1‐nitrobenzene (DFNB), respectively.