[4-(4-nitrophenyl)-2-oxido-1,2,5-oxadiazol-3-yl]methanol | 1147334-72-2

• 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: [4-(4-nitrophenyl)-2-oxido-1,2,5-oxadiazol-3-yl]methanol
• 英文别名: 3-(hydroxymethyl)-4-(4-nitrophenyl)-1,2,5-oxadiazole 2-oxide；[4-(4-Nitrophenyl)-2-oxido-1,2,5-oxadiazol-2-ium-3-yl]methanol
• CAS: 1147334-72-2
• 化学式: C₉H₇N₃O₅
• 分子量: 237.172
• InChiKey: IRWIFMMDUSBFPK-UHFFFAOYSA-N

物化性质

• 沸点：
  503.7±60.0 °C(predicted)
• 密度：
  1.66±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-(4-nitrophenyl)-2-oxido-1,2,5-oxadiazol-3-yl]methanol 在 copper(l) iodide 、 sodium azide 、 L-半胱氨酸 、 重氧水 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 85.17h， 生成
  参考文献：
  名称：

  Furoxans (1,2,5-Oxadiazole-N-Oxides) as Novel NO Mimetic Neuroprotective and Procognitive Agents

  摘要：

  Furoxans (1,2,5-oxadiazole-N-oxides) are thiol-bioactivated NO-mimetics that have not hitherto been studied in the CNS. Incorporation of varied substituents adjacent to the furoxan ring system led to modulation of reactivity toward bioactivation, studied by HPLC-MS/MS analysis of reaction products. Attenuated reactivity unmasked the cytoprotective actions of NO in contrast to the cytotoxic actions of higher NO fluxes reported previously for furoxans. Neuroprotection was observed in primary neuronal cell cultures following oxygen glucose deprivation (OGD). Neuroprotective activity was observed to correlate with thiol-dependent bioactivation to produce NO2-, but not with depletion of free thiol itself. Neuroprotection was abrogated upon cotreatment with a sGC inhibitor, ODQ, thus supporting activation of the NO/sGC/CREB signaling cascade by furoxans. Long-term potentiation (LTP), essential for learning and memory, has been shown to be potentiated by NO signaling, therefore, a peptidomimetic furoxan was tested in hippocampal slices treated with oligomeric amyloid-beta peptide (A beta) and was shown to restore synaptic function. The novel observation of furoxan activity of potential therapeutic use in the CNS warrants further studies.

  DOI：

  10.1021/jm201504s
• 作为产物：
  描述：

  4-硝基肉桂醇 在 sodium nitrite 作用下， 反应 16.0h， 生成 [4-(4-nitrophenyl)-2-oxido-1,2,5-oxadiazol-3-yl]methanol
  参考文献：
  名称：

  Selective Methylmagnesium Chloride Mediated Acetylations of Isosorbide: A Route to Powerful Nitric Oxide Donor Furoxans

  摘要：

  Isosorbide was functionalized with furoxan for the first time to give adducts that release nitric oxide up to 7.5 times faster than the commercial vasodilator, isosorbide-5-mononitrate (Is5N). The synthesis was facilitated by MeMgCl-mediated selective acetylation of isosorbide or selective deacetylation of isosorbide-2,5-diacetate, which was rationalized in terms of a more stable 5-alkoxide magnesium salt using DFT. Isosorbide-furoxans are safer to handle than Is5N due to greater thermal stability.

  DOI：

  10.1021/acs.orglett.8b01060

文献信息

• [EN] FUROXANS AS THERAPIES FOR NEURODEGENERATIVE DISORDERS<br/>[FR] FUROXANES UTILISÉS EN TANT QUE THÉRAPIES POUR DES TROUBLES NEURODÉGÉNÉRATIFS
  申请人：UNIV TOLEDO

  公开号：WO2018093762A1

  公开（公告）日：2018-05-24

  Furoxan compounds, compositions comprising the same, and methods of making and using the same, are described.

  Furoxan化合物、包含该化合物的组合物以及制备和使用该化合物的方法被描述。
• Furoxans as therapies for neurodegenerative disorders
  申请人：The University of Toledo

  公开号：US10590119B2

  公开（公告）日：2020-03-17

  Furoxan compounds, compositions comprising the same, and methods of making and using the same, are described.

  描述了呋喃类化合物、包含呋喃类化合物的组合物以及制造和使用呋喃类化合物的方法。
• Synthesis of oxadiazole-2-oxide analogues as potential antischistosomal agents
  作者：Ganesha Rai、Craig J. Thomas、William Leister、David J. Maloney

  DOI：10.1016/j.tetlet.2009.01.120

  日期：2009.4

  The synthesis of several 1,2,5-oxadiazole-2-oxide (Furoxan) analogues is described herein. These compounds were prepared in an effort to probe the SAR around the phenyl substituent and oxadiazole core for our studies toward thioredoxin-glutathione reductase (TGR) inhibition and antischistosomal activity. Published by Elsevier Ltd.
• FUROXANS AS THERAPIES FOR NEURODEGENERATIVE DISORDERS
  申请人：The University of Toledo

  公开号：US20190308959A1

  公开（公告）日：2019-10-10

  Furoxan compounds, compositions comprising the same, and methods of making and using the same, are described.