4-(hydroxymethyl)-3-phenylfuroxan | 135733-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(hydroxymethyl)-3-phenylfuroxan
• 英文别名: (5-Oxido-4-phenyl-1,2,5-oxadiazol-5-ium-3-yl)methanol
• CAS: 135733-31-2
• 化学式: C₉H₈N₂O₃
• 分子量: 192.174
• InChiKey: YQJVSOOSLONNLH-UHFFFAOYSA-N

物化性质

• 熔点：
  44-46 °C
• 沸点：
  418.5±47.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 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：
  71.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(hydroxymethyl)-3-phenylfuroxan 在 二溴亚砜 、 sodium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Oxido-4-(phenoxymethyl)-3-phenyl-1,2,5-oxadiazol-2-ium
  参考文献：
  名称：

  Synthesis and preliminary biological profile of new NO-donor tolbutamide analogues

  摘要：

  We describe a new class of NO-donor hypoglycemic products obtained by joining tolbutamide, a typical hypoglycemic sulfonylurea, with a NO-donor moiety through a hard link. As NO-donors we chose either furoxan (1,2,5-oxadiazole 2-oxide) derivatives or the classical nitrooxy function. A preliminary biological characterization of these compounds, including stimulation of insulin release from cultured rat pancreatic beta-cells and in vitro vasodilator and anti-aggregatory activities, is reported. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.103
• 作为产物：
  描述：

  3-(hydroxymethyl)-4-phenylfuroxan 以 甲苯 为溶剂， 生成 4-(hydroxymethyl)-3-phenylfuroxan
  参考文献：
  名称：

  NO供体化合物及其药物组合物和应用

  摘要：

  本发明涉及医药技术领域，特别涉及一种可用于治疗肺动脉高压的NO供体化合物、其药学上可接受的盐、其药物组合物，该化合物可以在生物体内释放出一氧化氮(NO)和肺动脉高压(PAH)的其他途径靶向治疗药物，能够通过简单方便的给药实现良好的双靶点治疗PAH的效果。

  公开号：

  CN115959996A

文献信息

• Synthesis of Furoxans from Styrenes under Basic or Neutral Conditions
  作者：Ryosuke Matsubara、Yuta Saeki、Jianhua Li、Kazuo Eda

  DOI：10.1055/s-0033-1338436

  日期：——

  NOBF4 under basic or even almost neutral reaction conditions. Acid-sensitive functional groups are tolerated under the developed basic conditions. For the substrates having poor reactivity, almost neutral conditions (using pyridine equimolar to NOBF4) are suitable for better yields. Furoxans (1,2,5-oxadiazole 2-oxides) can be synthesized from the corresponding styrenes using NOBF4 under basic or even

  摘要 呋喃烷（1,2,5-恶二唑2-氧化物）可以在碱性或几乎中性的反应条件下，使用NOBF 4由相应的苯乙烯合成。在已开发的基本条件下可以耐受酸敏感性官能团。对于反应性较差的底物，几乎中性的条件（使用与NOBF 4等摩尔的吡啶）适合提高产率。 呋喃烷（1,2,5-恶二唑2-氧化物）可以在碱性或几乎中性的反应条件下，使用NOBF 4由相应的苯乙烯合成。在已开发的基本条件下可以耐受酸敏感性官能团。对于反应性较差的底物，几乎中性的条件（使用与NOBF 4等摩尔的吡啶）适合提高产率。
• Synthesis of Furoxans (1,2,5-oxadiazole 2-oxides) from Styrenes and Nitrosonium Tetrafluoroborate in Non-Acidic Media and Mechanistic Study
  作者：Ryosuke Matsubara、Akihiro Ando、Yuta Saeki、Kazuo Eda、Naoki Asada、Tomoaki Tsutsumi、Yong Soon Shin、Masahiko Hayashi

  DOI：10.1002/jhet.2360

  日期：2016.7

  corresponding styrenes using nitrosonium tetrafluoroborate as the nitrosation reagent in pyridine (basic media) or dichloromethane (neutral media). Acid‐sensitive functional groups were tolerated under these conditions. The probable reaction mechanism was elucidated. The experimental results support an ionic reaction pathway in contrast to the conventional acidic conditions with a radical mechanism.

  在吡啶（碱性介质）或二氯甲烷（中性介质）中，使用四氟硼酸亚硝酸盐作为亚硝化试剂，由相应的苯乙烯合成了多种呋喃烷（1,2,5-恶二唑2-氧化物）。在这些条件下可以耐受酸敏感性官能团。阐明了可能的反应机理。与具有自由基机理的常规酸性条件相比，实验结果支持了离子反应途径。
• Structure Mechanism Insights and the Role of Nitric Oxide Donation Guide the Development of Oxadiazole-2-Oxides as Therapeutic Agents against Schistosomiasis
  作者：Ganesha Rai、Ahmed A. Sayed、Wendy A. Lea、Hans F. Luecke、Harinath Chakrapani、Stefanie Prast-Nielsen、Ajit Jadhav、William Leister、Min Shen、James Inglese、Christopher P. Austin、Larry Keefer、Elias S. J. Arnér、Anton Simeonov、David J. Maloney、David L. Williams、Craig J. Thomas

  DOI：10.1021/jm901021k

  日期：2009.10.22

  Schistosomiasis is a chronic parasitic disease affecting hundreds of millions of individuals worldwide. Current treatment depends on a single agent, praziquantel, raising concerns of emergence of resistant parasites. Here, we continue our explorations of an oxadiazole-2-oxide class of compounds we recently identified as inhibitors of thioredoxin glutathione reductase (TGR), a selenocysteine-containing flavoenzyme required by the parasite to maintain proper cellular redox balance. Through systematic evaluation of the core molecular structure of this chemotype, we define the essential pharmacophore, establish a link between the nitric oxide donation and TGR inhibition, determine the selectivity for this chemotype versus related reductase enzymes, and present evidence that these agents can be modified to possess appropriate drug metabolism and pharmacokinetic properties. The mechanistic link between exogenous NO donation and parasite injury is expanded and better defined. The results of these studies verify the utility of oxadiazole-2-oxides as novel inhibitors of TGR and as efficacious antischistosomal agents.
• Antiplatelet activity and TNF-α release inhibition of phthalimide derivatives useful to treat sickle cell anemia
  作者：Rafael C. Chelucci、Isabela J. de Oliveira、Karina P. Barbieri、Maria E. Lopes-Pires、Marisa C. Polesi、Diego E. Chiba、Iracilda Z. Carlos、Sisi Marcondes、Jean L. Dos Santos、ManChin Chung

  DOI：10.1007/s00044-019-02371-z

  日期：2019.8

  Sickle Cell Anemia (SCA) is one of the most prevalent hereditary hematological diseases worldwide. The disease is characterized by chronic inflammation, hypercoagulable state, and pro-thrombotic profile, which lead the vaso-occlusive process. In this work, we described the antiplatelet activity and the ability to reduce tumor necrosis factor-alpha (TNF-) levels of phthalimide derivatives. All compounds inhibited platelet aggregation induced by collagen and adenosine diphosphate, at levels ranging from 26.0 to 74.2% and 30.7 to 79.6%, respectively. The compounds exhibited reduced bleeding time compared to acetylsalicylic acid (ASA). Moreover, compounds 4c and 10c inhibited TNF- levels at 73.5% and 65.0%, respectively. These findings suggest that phthalimide derivatives 4c and 10c are promising lead compounds useful to prevent vaso-occlusion and inflammation associated with the sickle cell anemia.[GRAPHICS].
• Synthesis, characterization, and biological evaluation of furoxan coupled ibuprofen derivatives as anti-inflammatory agents
  作者：Mohd Amir、Mohd Wasim Akhter、Ozair Alam

  DOI：10.1007/s00706-015-1557-x

  日期：2016.3

  A series of furoxan-based nitric oxide releasing ibuprofen derivatives were synthesized and tested for their anti-inflammatory, analgesic, ulcerogenic, lipid peroxidation, and hepatotoxic properties. The compounds exhibited more protection than ibuprofen with regard to gastric toxicity. Among the tested compounds 4-[2-[2-(4-isobutylphenyl)propanamido] ethoxycarbonyl]-3-methylfuroxan and 4-[2-[2-(4-isobutylphenyl)propanoyl]hydrazinecarbonyl]-3-phenylfuroxan emerged as most active anti-inflammatory agents with reduced gastrotoxicity. The results showed that incorporation of NO donating group caused a moderate increase in anti-inflammatory activity with a marked decrease in gastric ulcerations compared to their parent drug ibuprofen. A molecular docking study of all the compounds was also performed to provide the binding modes of COX-1 enzyme. Among all the titledcompounds, 4-[2-[2-(4isobutylphenyl)propanamido]ethoxycarbonyl]-3-methylfuroxan was found to be most potent and have high docking score showing favorable orientation within the COX-1 binding site.