3-(苯磺酰基)-4-苯基-1,2,5-恶二唑 | 76016-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(苯磺酰基)-4-苯基-1,2,5-恶二唑
• 英文名称: 3-Phenylsulfonyl-4-phenylfurazan
• 英文别名: 3-phenyl-4-phenylsulfonylfurazan；3-(Benzenesulfonyl)-4-phenyl-1,2,5-oxadiazole
• CAS: 76016-70-1
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: OUVAQVRCZMBAKW-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C(Solv: methanol (67-56-1))
• 沸点：
  507.6±52.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 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：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(苯磺酰基)-4-苯基-1,2,5-恶二唑 在 sodium hydroxide 、 甲基磺酰氯 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Ethenesulfonyl-4-phenyl-furazan
  参考文献：
  名称：

  一些呋喃喃砜和相关呋喃酮的合成及其抗疟活性。

  摘要：

  合成在3或4位带有砜部分的呋喃喃衍生物，并测试其对恶性疟原虫的氯喹敏感的D10和耐氯喹的W2菌株的抗疟作用。考虑将呋喃赞类似物进行比较。活性最高的化合物是-SO2R基团在呋喃烷系统的3位上的产物。后一种物质在microM范围内表现出抗疟疾活性，可能与其释放NO的能力有关。

  DOI：

  10.1016/j.ejmech.2005.05.001
• 作为产物：
  描述：

  3-amino-4-phenylfuroxan 在 sodium hydroxide 、 双氧水 、 溶剂黄146 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 反应 45.0h， 生成 3-(苯磺酰基)-4-苯基-1,2,5-恶二唑
  参考文献：
  名称：

  Calvino; Mortarini; Gasco, European Journal of Medicinal Chemistry, 1980, vol. 15, # 5, p. 485 - 487

  摘要：

  DOI：

文献信息

• 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）。
• 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.
• H3 receptor ligands: new imidazole H3-antagonists endowed with NO-donor properties
  作者：Massimo Bertinaria

  DOI：10.1016/s0014-827x(03)00023-5

  日期：2003.3

  Synthesis and pharmacological properties of a group of compounds obtained by coupling the H(3)-antagonist SKF 91486 with the NO-donor 3-phenylfuroxan-4-yloxy and 3-benzenesulfonylfuroxan-4-yloxy moieties, as well as with the corresponding furazan analogues, devoid of NO-donating properties, are reported. All the products were tested for their H(3)-antagonistic and H(2)-agonistic properties on electrically-simulated guinea-pig ileum segments and guinea-pig papillary muscle, respectively. All the synthesised compounds displayed good H(3)-antagonistic properties (pA(2) range 7.02-8.49) while behaving only as weak partial H(2)-agonists. Derivative 28, the best NO-donor of the series, was able to trigger a dual NO-dependent muscle relaxation and H(3)-antagonistic effect on guinea-pig illeum.
• [3-(1 H -Imidazol-4-yl)propyl]guanidines containing furoxan moieties
  作者：Massimo Bertinaria、Antonella Di Stilo、Paolo Tosco、Giovanni Sorba、Enzo Poli、Cristina Pozzoli、Gabriella Coruzzi、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/s0968-0896(02)00651-x

  日期：2003.4

  Synthesis and pharmacological characterisation of a series of products obtained by coupling the H-3-antagonist SKF 91486 through appropriate spacers with the NO-donor 3-phenylfuroxan-4-yloxy and 3-benzenesulfonylfuroxan-4-yloxy moieties, as well as with the corresponding furazan substructures, devoid of NO-donating properties, are reported. All the products were tested for their H-3-antagonistic and H-2-agonistic properties on electrically-stimulated guinea-pig ileum segments and guinea-pig papillary muscle, respectively. The whole series of compounds displayed good H-3-antagonist behaviour and feeble partial H-2-agonist activity. Among furoxan derivatives, the benzenesulfonyl hybrid 28, a good NO-donor, triggered a dual NO-dependent muscle relaxation and H3-antagonistic effect on guinea-pig intestine. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A new class of NO-donor H3-antagonists
  作者：Paolo Tosco、Massimo Bertinaria、Antonella Di Stilo、Elisabetta Marini、Barbara Rolando、Giovanni Sorba、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.farmac.2003.12.008

  日期：2004.5

  Synthesis and pharmacological characterisation of a series of compounds obtained by joining, through appropriate spacers, NO-donor furoxan and nitrooxy moieties to the imidazole ring, as well as their structurally related analogues devoid of NO-donating properties are described. All the products were studied for their capacity to interact with H3-receptors present on the guinea-pig ileum and with H2-receptors present on guinea-pig right atrium. The whole series of products displayed reversible H3-antagonistic activity. No activity on H2-receptors was observed when the products were tested at 10 microM concentration. Many of the products were also able to induce partial relaxation when added to the bath after electrical contraction of the guinea-pig ileum during the study of their H3-antagonism. This phenomenon seems to be dependent on various factors; for some compounds it proved to be dependent on NO-mediated sGC activation, for other products it could be due to their weak M3-antagonism. The investigation of the lipophilic-hydrophilic balance of all the products indicates, for many of them, an ideal value to cross the blood-brain barrier.