4-phenyl-3-furoxanylcarbaldehyde oxime | 151733-56-1

• 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-phenyl-3-furoxanylcarbaldehyde oxime
• 英文别名: 3-(Nitrosomethylidene)-4-phenyl-1,2,5-oxadiazol-2(3H)-ol；N-[(2-oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methylidene]hydroxylamine
• CAS: 151733-56-1
• 化学式: C₉H₇N₃O₃
• 分子量: 205.173
• InChiKey: FSLMKWFSILVTIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-phenyl-3-furoxanylcarbaldehyde oxime 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90 mg的产率得到2-羟基-5-苯基-3-氧杂-2lambda5,4-二氮杂环戊并-1,4-二烯-1-甲腈
  参考文献：
  名称：

  Synthesis of furoxan derivatives: DABCO-mediated cascade sulfonylation/cyclization reaction of α-nitro-ketoximes

  摘要：

  A convenient and efficient method for the synthesis of furoxan derivatives from alpha-nitro-ketoximes and sulfonyl chlorides is reported. A wide variety of furoxan derivatives were smoothly obtained in good yields via a DABCO-mediated cascade sulfonylation/cyclization process under mild conditions. The usefulness of this method was also demonstrated by the conversions of the furoxan products into other promising compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.031
• 作为产物：
  描述：

  4-phenylfuroxan-3-carboxaldehyde 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 4-phenyl-3-furoxanylcarbaldehyde oxime
  参考文献：
  名称：

  Structure Mechanism Insights and the Role of Nitric Oxide Donation Guide the Development of Oxadiazole-2-Oxides as Therapeutic Agents against Schistosomiasis

  摘要：

  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.

  DOI：

  10.1021/jm901021k

文献信息

• Versatile approach to heteroarylfuroxan derivatives from oximinofuroxans via a one-pot, nitration/thermolysis/[3+2]-cycloaddition cascade
  作者：Alexander A. Larin、Leonid L. Fershtat、Ivan V. Ananyev、Nina N. Makhova

  DOI：10.1016/j.tetlet.2017.09.013

  日期：2017.10

  simple, general, and regioselective method has been developed for the synthesis of a series of heteroarylfuroxans, including isoxazolyl-, isoxazolinyl- and (1,2,4-oxadiazolyl)furoxans. The described method is based on a cascade of one-pot processes, including the nitration of furoxancarbaldehyde oximes, thermolysis of the formed nitrolic acids to generate furoxancarbonitrile oxides, and [3+2]-cycloaddition

  已经开发了一种简单，通用和区域选择性的方法来合成一系列杂芳基呋喃喃，包括异恶唑基-，异恶唑啉基-和（1,2,4-恶二唑基）呋喃。所描述的方法基于一系列的一锅法，包括硝化呋喃甲醛甲醛肟，热分解生成的硝酸以生成呋喃羰基腈，以及[3 + 2]-环加成反应和适当的双极性亲和性–炔烃，烯烃或活化的腈。
• 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。
• Gasco, Andre A Marcello; Boschi, Donatella; Stilo, Antonella Di, Arzneimittel-Forschung/Drug Research, 1998, vol. 48, # 3, p. 212 - 218
  作者：Gasco, Andre A Marcello、Boschi, Donatella、Stilo, Antonella Di、Medana, Claudio、Gasco, Alberto、Martorana, Piero Antonio、Schoenafinger, Karl

  DOI：——

  日期：——
• Gasco, Andrea Marcello; Stilo, Antonella Di; Fruttero, Roberta, Liebigs Annalen der Chemie, 1993, # 4, p. 441 - 444
  作者：Gasco, Andrea Marcello、Stilo, Antonella Di、Fruttero, Roberta、Sorba, Giovanni、Gasco, Alberto、Sabatino, Piera

  DOI：——

  日期：——
• Furoxans as Nitric Oxide Donors. 4-Phenyl-3-furoxancarbonitrile: Thiol-Mediated Nitric Oxide Release and Biological Evaluation
  作者：Claudio Medana、Giuseppe Ermondi、Roberta Fruttero、Antonella Di Stilo、Carlo Ferretti、Alberto Gasco

  DOI：10.1021/jm00051a020

  日期：1994.12