4-formyl-3-phenylfuroxan | 135733-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-formyl-3-phenylfuroxan
• 英文别名: 5-Oxo-4-phenyl-1,2,5lambda~5~-oxadiazole-3-carbaldehyde；5-oxido-4-phenyl-1,2,5-oxadiazol-5-ium-3-carbaldehyde
• CAS: 135733-35-6
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: DLXWGLICLICZTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-formyl-3-phenylfuroxan 在 jones reagent 作用下， 生成 α-oximinophenylacetonitrile oxide
  参考文献：
  名称：

  Calvino; Di Stilo; Fruttero, Il Farmaco, 1993, vol. 48, # 2, p. 321 - 334

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(hydroxymethyl)-4-phenylfuroxan 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 生成 4-formyl-3-phenylfuroxan
  参考文献：
  名称：

  Calvino; Di Stilo; Fruttero, Il Farmaco, 1993, vol. 48, # 2, p. 321 - 334

  摘要：

  DOI：

文献信息

• Synthesis and Structural Characterization of the Trimeric Furoxan (= Furazan 2-Oxide) System, a New Potent Vasodilating Moiety
  作者：Andrea M. Gasco、Clara Cena、Antonella Di Stilo、Giuseppe Ermondi、Claudio Medana、Alberto Gasco

  DOI：10.1002/hlca.19960790706

  日期：1996.10.30

  series of terfuroxan (= terfurazan trioxide) derivatives 1a–h and 2a–j are reported (Schemes 1 and 2). Structural assignments were confirmed principally by mass and 13C- and 1H-NMR spectroscopy. The extent and the initial rate of NO release in the presence of thiol cofactor was evaluated for each derivative. Vasodilator effects of all the terfuroxan derivatives were evaluated on endothelium-denuded strips

  据报道，一系列的呋喃喃（=三氟叔丁基）衍生物1a–h和2a–j的合成，结构表征和NO供体特性（方案1和2）。主要通过质量以及13 C-和1 H-NMR光谱确认结构归属。对于每种衍生物，评估在硫醇辅因子存在下NO释放的程度和初始速率。在用去甲肾上腺素预收缩的大鼠主动脉内皮剥除的条带上评估了所有特氟沙星衍生物的血管舒张作用。在10m̈M氧合血红蛋白（HbO 2），这是众所周知的NO清道夫。整个系列显示出高血管舒张力；活性最高的三氟呋喃（1a，b，g和2i）的效力是作为参考的三硝酸甘油酯的5-10倍（见表3）。在HbO 2存在下观察到的效能降低与NO参与血管舒张作用一致。4,3'：4'，4''连接（系列1；呋喃喃编号）产生了最有效的化合物。构象因素似乎在该活动中起重要作用。取代基的理化性质与衍生物的效力之间没有明确的关系。
• 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.
• 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.
• Gasco; Fruttero; Sorba, Arzneimittel-Forschung/Drug Research, 1992, vol. 42, # 7, p. 921 - 925
  作者：Gasco、Fruttero、Sorba、Gasco、Budriesi、Chiarini

  DOI：——

  日期：——
• Gasco, Andrea Marcello; Fruttero, Roberta; Sorba, Giovanni, Liebigs Annalen der Chemie, 1991, # 11, p. 1211 - 1213
  作者：Gasco, Andrea Marcello、Fruttero, Roberta、Sorba, Giovanni、Gasco, Alberto

  DOI：——

  日期：——