3-(phenylsulfonyl)-4-(phenylthio)furazan | 691356-55-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylsulfonyl)-4-(phenylthio)furazan
• 英文别名: 3-(Benzenesulfonyl)-4-phenylsulfanyl-1,2,5-oxadiazole
• CAS: 691356-55-5
• 化学式: C₁₄H₁₀N₂O₃S₂
• 分子量: 318.377
• InChiKey: FGMSTTAYIYQDMB-UHFFFAOYSA-N

物化性质

• 熔点：
  72.5-73 °C
• 沸点：
  496.4±55.0 °C(Predicted)
• 密度：
  1.50±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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(phenylsulfonyl)-4-(phenylthio)furazan 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 3-[3-(1H-Imidazol-4-yl)-propoxy]-4-phenylsulfanyl-furazan
  参考文献：
  名称：

  A new class of NO-donor H3-antagonists

  摘要：

  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.

  DOI：

  10.1016/j.farmac.2003.12.008
• 作为产物：
  描述：

  苯硫酚 、 3,4-bis-(phenylsulfonyl)furazan 在 三乙胺 作用下， 以 乙腈 为溶剂， 以91%的产率得到3-(phenylsulfonyl)-4-(phenylthio)furazan
  参考文献：
  名称：

  A new class of NO-donor H3-antagonists

  摘要：

  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.

  DOI：

  10.1016/j.farmac.2003.12.008

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）。