2-fluoropyridine-3-aldoxime | 1319649-65-4

• 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: 2-fluoropyridine-3-aldoxime
• 英文别名: N-[(2-fluoropyridin-3-yl)methylidene]hydroxylamine
• CAS: 1319649-65-4
• 化学式: C₆H₅FN₂O
• 分子量: 140.117
• InChiKey: KSBHELBYFCZELP-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  246.3±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 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：
  45.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-fluoropyridine-3-aldoxime 在 四(三苯基膦)钯 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 生成 5-[3-(2-fluoropyridin-3-yl)-1,2-oxazol-5-yl]-2-propan-2-yl-3H-isoindol-1-one
  参考文献：
  名称：

  芳基异恶唑衍生物作为代谢型谷氨酸受体1拮抗剂的合成及生物学评价：神经性疼痛的潜在治疗方法

  摘要：

  谷氨酸是主要的兴奋性神经递质，已知能激活大脑中代谢型和离子型谷氨酸受体。在这些谷氨酸受体中，代谢型谷氨酸受体1（mGluR1）与多种脑部疾病有关，包括焦虑症，精神分裂症和慢性疼痛。数项研究表明，mGluR1信号传导的阻断减少了动物模型中的疼痛反应，表明mGluR1是治疗神经性疼痛的有希望的靶标。在这项研究中，我们开发了具有芳基异恶唑支架的mGluR1拮抗剂，并鉴定了几种在体内具有口服活性的化合物。我们相信这些化合物可以作为研究mGluR1的作用的有用工具，并且可以潜在地治疗神经性疼痛。

  DOI：

  10.1016/j.bmcl.2015.01.035
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 在 potassium permanganate 、 tetrafluoroboric acid 、 氯化亚砜 、 Pd-BaSO₄ 、 盐酸羟胺 、 氢气 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 生成 2-fluoropyridine-3-aldoxime
  参考文献：
  名称：

  Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

  摘要：

  Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pK(a)) and second-order rate constants (k(ox)-) of the fluorinated pyridinealdoximes towards satin were measured. 2,3,5,6-Tetrafluoropyridine-4-aldoxime had the best profile: its k(ox)- approached that of the therapeutic oxime P2S (310 vs. 120 l mol(-1) min(-1)), but its higher pK(a) (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK(a) nearer to 8 and enhance their therapeutic potential. Crown Copyright (c) 2011 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.05.028

文献信息

• Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning
  作者：Christopher M. Timperley、R. Eric Banks、Ian M. Young、Robert N. Haszeldine

  DOI：10.1016/j.jfluchem.2011.05.028

  日期：2011.8

  Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pK(a)) and second-order rate constants (k(ox)-) of the fluorinated pyridinealdoximes towards satin were measured. 2,3,5,6-Tetrafluoropyridine-4-aldoxime had the best profile: its k(ox)- approached that of the therapeutic oxime P2S (310 vs. 120 l mol(-1) min(-1)), but its higher pK(a) (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK(a) nearer to 8 and enhance their therapeutic potential. Crown Copyright (c) 2011 Published by Elsevier B.V. All rights reserved.
• Synthesis and biological evaluation of aryl isoxazole derivatives as metabotropic glutamate receptor 1 antagonists: A potential treatment for neuropathic pain
  作者：Gyeong hi Cho、TaeHun Kim、Woo Seung Son、Seon Hee Seo、Sun-Joon Min、Yong Seo Cho、Gyochang Keum、Kyu-Sung Jeong、Hun Yeong Koh、Jiyoun Lee、Ae Nim Pae

  DOI：10.1016/j.bmcl.2015.01.035

  日期：2015.3

  Glutamate is the major excitatory neurotransmitter and known to activate the metabotropic and ionotropic glutamate receptors in the brain. Among these glutamate receptors, metabotropic glutamate receptor 1 (mGluR1) has been implicated in various brain disorders including anxiety, schizophrenia and chronic pain. Several studies demonstrated that the blockade of mGluR1 signaling reduced pain responses

  谷氨酸是主要的兴奋性神经递质，已知能激活大脑中代谢型和离子型谷氨酸受体。在这些谷氨酸受体中，代谢型谷氨酸受体1（mGluR1）与多种脑部疾病有关，包括焦虑症，精神分裂症和慢性疼痛。数项研究表明，mGluR1信号传导的阻断减少了动物模型中的疼痛反应，表明mGluR1是治疗神经性疼痛的有希望的靶标。在这项研究中，我们开发了具有芳基异恶唑支架的mGluR1拮抗剂，并鉴定了几种在体内具有口服活性的化合物。我们相信这些化合物可以作为研究mGluR1的作用的有用工具，并且可以潜在地治疗神经性疼痛。