4-phenylsulfonylfuroxan-3-carboxamide | 1235476-35-3

• 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: 4-phenylsulfonylfuroxan-3-carboxamide
• 英文别名: 4-(benzenesulfonyl)-2-oxido-1,2,5-oxadiazol-2-ium-3-carboxamide
• CAS: 1235476-35-3
• 化学式: C₉H₇N₃O₅S
• 分子量: 269.238
• InChiKey: JQHWIBLQDQJXQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-phenylsulfonylfuroxan-3-carboxamide 在 吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到4-phenylsulfonylfuroxan-3-carbonitrile
  参考文献：
  名称：

  Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein

  摘要：

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.

  DOI：

  10.1021/jm100066y
• 作为产物：
  描述：

  4-phenylthiofuroxan-3-carboxamide 在 双氧水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到4-phenylsulfonylfuroxan-3-carboxamide
  参考文献：
  名称：

  Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein

  摘要：

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.

  DOI：

  10.1021/jm100066y

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）。
• NITRIC OXIDE FUROXAN DERIVATIVE COMPOUNDS ENDOWED WITH ANTITUMORAL ACTIVITY
  申请人：Viola Antonella

  公开号：US20120021007A1

  公开（公告）日：2012-01-26

  The present invention relates to nitric oxide furoxan derivative compounds which showed to be active in the treatment of tumors. In addition, they may be used as adjuvants in cancer immunotherapy.