6-((1-aminocyclohexyl)ethynyl)-3-fluoro-N'-hydroxypicolinimidamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-((1-aminocyclohexyl)ethynyl)-3-fluoro-N'-hydroxypicolinimidamide
• 英文别名: 6-[2-(1-aminocyclohexyl)ethynyl]-3-fluoro-N'-hydroxypyridine-2-carboximidamide
• 化学式: C₁₄H₁₇FN₄O
• 分子量: 276.314
• InChiKey: BKSSYMCNXZZYBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  97.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-((1-aminocyclohexyl)ethynyl)-3-fluoropicolinonitrile 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以79%的产率得到6-((1-aminocyclohexyl)ethynyl)-3-fluoro-N'-hydroxypicolinimidamide
  参考文献：
  名称：

  溴氰氟吡啶核的 Sonogashira 交叉偶联反应：获得 5- 和 6-炔基氟吡啶胺肟支架

  摘要：

  我们公开了一种通用的两步程序，以从 5- 和 6-溴-3-氟-2-氰基吡啶和广泛的容易获得的 5- 和 6-炔基-3-氟-2-吡啶胺肟中获得迄今为止未知的和正在探索的第一步是使用 Sonogashira 交叉偶联获得可用的和工作台稳定的末端炔烃。在用羟胺处理炔基氟氰基吡啶后，极性胺肟基团的生成是在后期实现的。这种温和且操作简单的两步室温工艺与对映纯手性底物和各种功能兼容，包括游离醇、未保护和 CBz 保护的胺、丙酮化物、苄基醚、酰胺、酰亚胺、双取代炔烃和张力饱和杂环。

  DOI：

  10.1002/ejoc.202100563

文献信息

• 6-Substituted 3-Fluoro-2-Pyridinaldoxime, 3-Fluoro-2-pyridine hydroxamic acid, and 3-Fluoro-2-Pyridinamidoxime scaffolds
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US11370772B2

  公开（公告）日：2022-06-28

  Disclosed is a compound of formula (II), as well as to a process for preparing the compounds of formula (II) by a chemoselective Sonogashira reaction. It also relates to a pharmaceutical composition including at least one compound of formula (II) and at least one pharmaceutically acceptable support. Finally, it relates to the use of such a compound as a medicine, preferably in the treatment of a nervous and/or respiratory failure due to intoxication with at least one organophosphorous nerve agent; in the treatment of neurological diseases such as Alzheimer's disease; and/or in the treatment of cancer; and/or for use as antiviral drug.

  本发明公开了一种式 (II) 化合物，以及通过化学选择性 Sonogashira 反应制备式 (II) 化合物的工艺。还涉及一种药物组合物，包括至少一种式（II）化合物和至少一种药学上可接受的支持物。最后，本发明还涉及此类化合物作为药物的用途，优选用于治疗至少一种有机磷神经毒剂中毒引起的神经和/或呼吸衰竭；治疗神经系统疾病，如阿尔茨海默病；和/或治疗癌症；和/或用作抗病毒药物。
• 6-SUBSTITUTED 3-FLUORO-2-PYRIDINALDOXIME, 3-FLUORO-2-PYRIDINE HYDROXAMIC ACID, AND 3-FLUORO-2-PYRIDINAMIDOXIME SCAFFOLDS
  申请人：Centre National de la Recherche Scientifique

  公开号：EP3697769A1

  公开（公告）日：2020-08-26
• [EN] 6-SUBSTITUTED 3-FLUORO-2-PYRIDINALDOXIME, 3-FLUORO-2-PYRIDINE HYDROXAMIC ACID, AND 3-FLUORO-2-PYRIDINAMIDOXIME SCAFFOLDS<br/>[FR] 3-FLUORO-2-PYRIDINALDOXIME À SUBSTITUTION EN POSITION 6, ACIDE HYDROXAMIQUE DE 3-FLUORO-2-PYRIDINE ET ÉCHAFAUDAGES DE 3-FLUORO-2-PYRIDINAMIDOXIME
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2019076986A1

  公开（公告）日：2019-04-25

  The present invention relates to a compound of formula (II), as well as to a process for preparing the compounds of formula (II) by a chemoselective Sonogashira reaction. It also relates to a pharmaceutical composition comprising at least one compound of formula (II) and at least one pharmaceutically acceptable support. Finally, it relates to the use of such a compound as a medicine, preferably in the treatment of a nervous and/or respiratory failure due to intoxication with at least one organophosphorous nerve agent; in the treatment of neurological diseases such as Alzheimer's disease; and/or in the treatment of cancer; and/or for use as antiviral drug.
• Sonogashira Cross‐Coupling Reaction of Bromocyanofluoro Pyridine Compounds: Access to 5‐ and 6‐Alkynylfluoropyridinamidoximes Scaffolds
  作者：Franck Razafindrainibe、Camille Voros、Yerri Jagadeesh、Nimmakayala Mallikarjuna Reddy、Allan Tissier、Keven Mardy、Norbert Reihanian‐Hadany、Richard C. D. Brown、Rachid Baati

  DOI：10.1002/ejoc.202100563

  日期：2021.8.13

  alkynes, using Sonogashira cross-coupling, as the first step. The generation of the polar amidoxime group is realized at a late-stage upon treatment of the alkynylfluorocyanopyridine by hydroxylamine. This mild and operationally simple two-step room temperature process is compatible with enantiopure chiral substrates and various functionality including free alcohols, unprotected and CBz-protected amines

  我们公开了一种通用的两步程序，以从 5- 和 6-溴-3-氟-2-氰基吡啶和广泛的容易获得的 5- 和 6-炔基-3-氟-2-吡啶胺肟中获得迄今为止未知的和正在探索的第一步是使用 Sonogashira 交叉偶联获得可用的和工作台稳定的末端炔烃。在用羟胺处理炔基氟氰基吡啶后，极性胺肟基团的生成是在后期实现的。这种温和且操作简单的两步室温工艺与对映纯手性底物和各种功能兼容，包括游离醇、未保护和 CBz 保护的胺、丙酮化物、苄基醚、酰胺、酰亚胺、双取代炔烃和张力饱和杂环。