3-phenyl-4-(phenylsulfonyl)furoxan | 76016-71-2

• 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: 3-phenyl-4-(phenylsulfonyl)furoxan
• 英文别名: 4-Benzenesulfonyl-3-phenyl-furazan 2-oxide；4-(benzenesulfonyl)-2-oxido-3-phenyl-1,2,5-oxadiazol-2-ium
• CAS: 76016-71-2
• 化学式: C₁₄H₁₀N₂O₄S
• 分子量: 302.31
• InChiKey: FSTIOGUUUMQBCU-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: methanol (67-56-1))
• 沸点：
  548.6±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-phenyl-4-(phenylsulfonyl)furoxan 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 三氟乙酸 为溶剂， 反应 27.0h， 生成 4-(2-Hydroxyethylsulfonyl)-3-phenylfuroxan
  参考文献：
  名称：

  不对称取代的呋喃喃。第18部分。呋喃烷系统和相关呋喃酮中的微笑重排

  摘要：

  制备和phenylfurazans的碱促进的重排微笑（串联一），3-苯基呋喃烷（系列b）和4-苯呋喃（系列Ç）轴承2-羟基（1），2-羟基乙基（2），carbamoylmethylthio（3）和carbamoylmethylsulfonyl（4）在式杂环功能进行说明。在相似的条件下，系列a和b的化合物给出了预期的Smiles重排产物，唯一的例外是酰胺衍生物3水解成相应的酸。4-苯基呋喃烷系列对Smiles重排的行为是完全不同的。在接近于相应的3-苯基异构体所采用的条件下，1c和2c分解成未确定的极性产物。提供3c作为主要产品3-巯基4-苯基呋喃山而4c提供（Z）-2-羟基亚氨基-2-苯基乙腈。讨论了这些产物形成的可能机理。

  DOI：

  10.1039/b104845g
• 作为产物：
  描述：

  3-phenyl-4-phenylthiofuroxan 在 potassium permanganate 、 溶剂黄146 作用下， 以80%的产率得到3-phenyl-4-(phenylsulfonyl)furoxan
  参考文献：
  名称：

  不对称取代的呋喃喃。第16部分†。碱性介质中苯磺酰基取代的呋喃烷与乙醇和乙硫醇的反应

  摘要：

  讨论了使用苯磺酰基取代的呋喃类化合物作为柔性中间体，用于合成新型功能化的呋喃类化合物，其潜在的生物学特性引起人们的兴趣。在碱性介质中，苯磺酰甲酰基苯基磺酰基呋喃喃异构体7a和7b与乙醇和乙硫醇反应，分别得到预期的醚和硫化物。根据实验方法，双（苯磺酰基）呋喃喃（1）与乙醇在碱性介质中反应，得到3-苯磺酰基-4-乙氧基呋喃喃（2）或二乙氧基呋喃喃（3）。相反，1与乙硫醇的反应给出了取代化合物和4-苯磺酰基-3-乙基硫呋喃的混合物（11）。化合物的结构已经通过核磁共振波谱进行了鉴定，并且在3-苯磺酰基-4-乙基硫代呋喃（9b）的情况下，通过X射线分析得以证实。

  DOI：

  10.1002/jhet.5570330220

文献信息

• Structural and biological characterization of new hybrid drugs joining an HDAC inhibitor to different NO-donors
  作者：Sandra Atlante、Konstantin Chegaev、Chiara Cencioni、Stefano Guglielmo、Elisabetta Marini、Emily Borretto、Carlo Gaetano、Roberta Fruttero、Francesco Spallotta、Loretta Lazzarato

  DOI：10.1016/j.ejmech.2017.12.047

  日期：2018.1

  pathologic contexts. Here we further investigated the power of their combination in a single hybrid molecule. Nitrooxy groups or substituted furoxan derivatives were joined to the α-position of the pyridine ring of the selective class I HDAC inhibitor MS-275. Biochemical analysis showed that the association with the dinitrooxy compound 31 or the furoxan derivative 16 gives hybrid compounds the ability

  HDAC抑制剂和NO供体已经独立显示出其在病理学背景下的广泛治疗潜力。在这里，我们进一步研究了它们在单个杂合分子中结合的能力。将硝基氧基或取代的呋喃烷衍生物连接至选择性I类HDAC抑制剂MS-275的吡啶环的α位。生化分析表明，与二硝基氧基化合物31或呋喃喃衍生物16的结合赋予杂化化合物保留单部分活性的能力。然后在肌肉分化测定中测试了这两个新的杂合分子。带有部分31的杂化化合物促成以高度多核纤维为特征的大型肌管的形成，可能是由于对成肌细胞表达的强诱导所致。由于它们独特的生物学特性，这些化合物可能代表了心血管，神经肌肉和炎性疾病的新治疗工具。
• NOBF4-Mediated Assembly of the Sydnone Imine Scaffold in the Synthesis of Double Nitric Oxide Donors
  作者：Leonid L. Fershtat、Alexander D. Shuvaev、Egor S. Zhilin

  DOI：10.1055/a-2011-7264

  日期：——

  step was developed. The described protocol excludes the isolation of carcinogenic N-nitrosamines, operates broad substrate scope, and enables the preparation of fully substituted sydnone imines linked to the furoxan ring via different linkers or directly through C–C bond. Synthesized library of furoxan-sydnone imine hybrids demonstrated a promising ability to release NO in a wide range of concentrations

  开发了一种直接构建呋喃-苯酮亚胺双 NO-供体的方法，该方法涉及 NOBF 4介导的 α-氨基腈的亚硝化-环化序列作为关键合成步骤。所描述的协议不包括致癌性N -nitrosamines的分离, 操作范围广泛, 并能够通过不同的连接器或直接通过 C-C 键连接到呋喃环的完全取代的 sydnone 亚胺。合成的呋喃-苯酮亚胺杂化物库展示了在广泛浓度范围内释放 NO 的有前途的能力，这对各种生物医学见解很有用。
• ——
  作者：Donatella Boschi、Antonella Di Stilo、Clara Cena、Marco Lolli、Roberta Fruttero、Alberto Gasco

  DOI：10.1023/a:1012136030849

  日期：——

  Purpose. A series of derivatives having a propranolol-like moiety linked to NO-donor furoxan substructures were synthesized. The main objective of this investigation was to obtain agents with mixed No-dependent vasodilating and beta-blocking activities.Methods. Most of the target compounds were synthesized from the appropriate furoxans bearing XCH2CH2NH2 (X = O, S, SO2) chains at the 4 position of the ring, using AI(C2H5)(3) in methylene chloride solution and (+/-)2,3-epoxypropyl 1-naphtyl ether. Two of the final products (X = CONH) were obtained by coupling the appropriate furoxancarboxylic acids with N-[2-hydroxy-3-(1-naphthoxy)propyl]ethylenediamine. beta(1)- and beta(2)-blocking activities were examined on isolated guinea pig right atria and on guinea pig trachea respectively. Vasodilating properties were assessed on endothelium denuded strips of rat aortaResult. Some derivatives behave as well balanced "hybrids" displaying NO-dependent vasodilating and beta-blocking properties in the same concentration range. Some others display either prevalent beta-blocking or vasodilating activity. Generally speaking hybrid formation lowers the affinity for beta-receptors, in particular for beta(2)-type, to give an increase in beta(1)/beta(2) selectivity.Conclusions. The furoxan system is a flexible tool in designing analogues of propranolol whose NO-donating and beta-blocking properties are modulated over a wide range.
• Water Soluble Furoxan Derivatives as NO Prodrugs
  作者：Giovanni Sorba、Claudio Medana、Roberta Fruttero、Clara Cena、Antonella Di Stilo、Ubaldina Galli、Alberto Gasco

  DOI：10.1021/jm960379t

  日期：1997.2.1

  The synthesis, characterization, NO donor properties, and in vitro vasodilating activity of a series of water soluble furoxans (5-14a,b) are described. AU of the compounds released NO when treated with a large excess of cysteine under physiological conditions (pH 7.4; 37 degrees C). The amount of NO produced after 1 h of incubation was evaluated by detecting nitrites, via the Griess reaction. Derivatives 5b, 7b, and 14b were able to release nitric oxide also in the absence of the thiol cofactor. The initial rates of NO release were determined at different concentrations, using a spectrophotometric technique based on the NO-induced oxidation of oxyhemoglobin (HbO(2)) to methemoglobin (MetHb). The initial rates of NO release were Linearly dependent on the concentrations of the single compounds. The vasodilating potency (EC(50)) of all the derivatives was assessed on rat aortic. strips precontracted with noradrenaline. Correlation between potency and initial NO release rate is discussed.
• Synthesis and preliminary pharmacological characterisation of a new class of nitrogen-containing bisphosphonates (N-BPs)
  作者：Marco L. Lolli、Barbara Rolando、Paolo Tosco、Shilpi Chaurasia、Antonella Di Stilo、Loretta Lazzarato、Eva Gorassini、Riccardo Ferracini、Simonetta Oliaro-Bosso、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.bmc.2010.02.058

  日期：2010.4

  A new series of bisphosphonates bearing either the nitrogen-containing NO-donor furoxan (1,2,5-oxadiazole 2-oxide) system or the related furazan (1,2,5-oxadiazole) in lateral chain has been developed. pK(a) values and affinity for hydroxyapatite were determined for all the compounds. The products were able to inhibit osteoclastogenesis on RAW 246.7 cells at 10 mu M concentration. The most active compounds were further assayed on human PBMC cells and on rat microsomes. Unlike most nitrogen-containing bisphosphonates which target farnesyl pyrophosphate synthase, experimental and theoretical investigations suggest that the activity of our derivatives may be related to different mechanisms. The furoxan derivatives were also tested for their ability to relax rat aorta strips in view of their potential NO-dependent vasodilator properties. (C) 2010 Elsevier Ltd. All rights reserved.