3,4-bis-(phenylsulfonyl)furazan | 98384-57-7

• 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: 3,4-bis-(phenylsulfonyl)furazan
• 英文别名: bis(benzenesulfonyl)furazan；3,4-Di(benzenesulfonyl)-1,2,5-oxadiazole；3,4-bis(benzenesulfonyl)-1,2,5-oxadiazole
• CAS: 98384-57-7
• 化学式: C₁₄H₁₀N₂O₅S₂
• 分子量: 350.376
• InChiKey: RGWDUVWEUZQUIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-bis-(phenylsulfonyl)furazan 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 三苯基膦 、 甲胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 tert-butyl {2-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]ethyl}carbamate
  参考文献：
  名称：

  羟基1,2,5-恶二唑基部分是羧基的生物等排体。γ-氨基丁酸（GABA）相关化合物的合成，电离常数和药理学表征。

  摘要：

  合成了三个含有氨基烷基取代基的4-取代的1,2,5-恶二唑-3-醇（γ-氨基丁酸（GABA）的类似物和同系物），以研究羟基1,2,5-恶二唑基部分是GABA受体上的羧基。目标化合物的pK（a）值接近GABA。在培养的大脑皮层神经元的GABA（A）受体上，鉴定出弱激动剂和部分激动剂谱，表明4-羟基-1,2,5-恶二唑-3-基单元是非经典的羧基生物等排体。

  DOI：

  10.1021/jm051288b
• 作为产物：
  描述：

  呋咱氮氧化物供体 在 三甲氧基磷 作用下， 反应 1.0h， 以90%的产率得到3,4-bis-(phenylsulfonyl)furazan
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1012136030849

文献信息

• Nitric Oxide Donor β₂-Agonists:  Furoxan Derivatives Containing the Fenoterol Moiety and Related Furazans
  作者：M. Federica Buonsanti、Massimo Bertinaria、Antonella Di Stilo、Clara Cena、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm0704595

  日期：2007.10.1

  has been joined with furoxan NO-donor moieties to give new NO-donor beta2-agonists. The furazan analogues, devoid of the property to release NO, were also synthesized for comparison. All the compounds retained beta2-agonistic activity at micromolar or submicromolar concentration when tested on guinea pig tracheal rings precontracted with carbachol. Among the furoxan derivatives, the NO contribution

  非诺特罗（一种用于治疗的β2肾上腺素受体激动剂）的结构已与呋喃喃的NO供体基团结合在一起，得到了新的NO供体β2受体激动剂。还合成了不具有释放NO的性质的呋喃赞类似物以进行比较。当在与卡巴胆碱预收缩的豚鼠气管环上进行测试时，所有化合物在微摩尔或亚微摩尔浓度下均保持β2激动活性。在呋喃喃衍生物中，在微摩尔浓度的产物15b中，NO对气管舒张的作用是明显的。所有这些新的NO供体杂种都能够扩张与去氧肾上腺素预收缩的大鼠主动脉条。呋喃喃和呋喃山衍生物均显示出比非诺特罗更大的抗氧化活性。
• Structure–Activity Relationship Studies on Tetrahydroisoquinoline Derivatives: [4′-(6,7-Dimethoxy-3,4-dihydro-1<i>H</i>-isoquinolin-2-ylmethyl)biphenyl-4-ol] (<b>MC70</b>) Conjugated through Flexible Alkyl Chains with Furazan Moieties Gives Rise to Potent and Selective Ligands of P-glycoprotein
  作者：Stefano Guglielmo、Loretta Lazzarato、Marialessandra Contino、Maria G. Perrone、Konstantin Chegaev、Antonio Carrieri、Roberta Fruttero、Nicola A. Colabufo、Alberto Gasco

  DOI：10.1021/acs.jmedchem.6b00252

  日期：2016.7.28

  P-glycoprotein (P-gp) is a well-known membrane transporter expressed in a number of strategic biological barriers, where it exerts a protective effect of paramount importance. Conversely it is one of the main causes of multidrug resistance (MDR), being capable of effluxing many chemotherapeutics. In a development of previous research, a small library of compounds was created conjugating diversely substituted

  P-糖蛋白（P-gp）是在许多战略性生物屏障中表达的众所周知的膜转运蛋白，在其中发挥了至关重要的保护作用。相反，它是多药耐药性（MDR）的主要原因之一，能够排出许多化学治疗药。在先前研究的发展中，创建了一个小的化合物文库，将各种取代的呋喃山环与著名的P-gp抑制剂MC70结合在一起。评估了这些化合物对P-gp和另一种转运蛋白（MRP1）的效能，表观渗透性（P app）及其诱导ATPase活性的能力，从而描绘出完整的功能概况。与铅化合物不同，它们显示了底物的作用机理和对P-gp的高选择性。有关其活性的数据范围从低微摩尔到亚纳摩尔EC 50，最有趣的化合物是15（0.97 nM），19（1.3 nM），25（0.60 nM）和27（0.90 nM）。
• New praziquantel derivatives containing NO-donor furoxans and related furazans as active agents against Schistosoma mansoni
  作者：Stefano Guglielmo、Daniela Cortese、Francesca Vottero、Barbara Rolando、Valerie P. Kommer、David L. Williams、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.ejmech.2014.07.007

  日期：2014.9

  praziquantel hybrid compounds was obtained by combining praziquantel (PZQ) and furoxan moieties in a single entity. NO-donor properties of the furoxan derivatives were evaluated by detecting nitrite after incubation of the products in 7.4 pH buffered solution in the presence of l-cysteine. Structurally-related furazans, devoid of NO release capacity, were also synthesized for control purposes. All

  通过将吡喹酮 (PZQ) 和呋喃酮部分组合在一个实体中，获得了一系列 NO 供体吡喹酮杂化化合物。通过在存在L-半胱氨酸的情况下将产物在 7.4 pH 缓冲溶液中温育后检测亚硝酸盐来评估呋喃酮衍生物的 NO 供体性质。为了控制目的，还合成了结构相关的呋喃嗪，缺乏 NO 释放能力。研究了所有产品抑制重组曼氏血吸虫硫氧还蛋白谷胱甘肽还原酶（TGR）的能力。与 PZQ 相比，评估了在产品存在下培养的成年曼氏血吸虫蠕虫的活动性和死亡。结果分析表明，一些产品同时具有PZQ和NO依赖性抗寄生虫特性。化合物6、7、18和24成为最有趣的平衡杂种，值得对 PZQ 抗性寄生虫进行进一步研究。
• Heterocyclic ring cleavage upon collision-induced dissociation of deprotonated 3-hydroxy-1,2,5-oxadiazoles (3-hydroxyfurazans)
  作者：J. Stuart Grossert、Agnese C. Pippione、Donatella Boschi、Marco L. Lolli、Robert L. White

  DOI：10.1002/jms.3724

  日期：2015.12

  A series of 4-substituted 3-hydroxyfurazans were subjected to electrospray ionization tandem mass spectrometry. At low collision energy, oxyisocyanate ([O=C=N–O]−, m/z 58) was formed as the predominant product ion from each deprotonated 3-hydroxyfurazan, indicating cleavage of the heterocyclic ring. The facile energetics of this characteristic fragmentation process was confirmed by density functional computations.

  对一系列 4-取代的 3-羟基呋喃进行了电喷雾离子化串联质谱分析。在低碰撞能量下，氧异氰酸酯（[O=C=N-O]-，m/z 58）形成为每个去质子化 3-羟基呋喃的主要产物离子，表明杂环被裂解。密度泛函计算证实了这一特征碎裂过程的简易能量学原理。
• Nicorandil analogues containing NO-donor furoxans and related furazans
  作者：Donatella Boschi、Clara Cena、Antonella Di Stilo、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/s0968-0896(00)00098-5

  日期：2000.7

  The synthesis and in vitro vasodilating properties of hybrid compounds in which furoxan (1,2,5-oxadiazole 2-oxide) moieties, endowed with different NO-donor properties, were substituted for the nitroxy function of Nicorandil are reported. The corresponding cyanoguanidine analogues are also considered. This approach has led to a series of vasorelaxing compounds devoid of affinity for K-ATP channels, whose activity is prevalently due to their ability to activate sGC, at the concentrations of the experiments. Related furazan (1,2,5-oxadiazole) derivatives, unable to release nitric oxide were also prepared and studied for control. The amide analogues of Nicorandil display feeble vasorelaxing action not involving the activation of K+ channels, while in the guanidine analogues, this mechanism seems to underlie this action. (C) 2000 Elsevier Science Ltd. All rights reserved.