4-(4-fluorophenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole | 882289-35-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(4-fluorophenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole
• 英文别名: Cyto5H11；4-(4-fluorophenyl)sulfanyl-7-nitro-2,1,3-benzoxadiazole
• CAS: 882289-35-2
• 化学式: C₁₂H₆FN₃O₃S
• 分子量: 291.262
• InChiKey: ZJIWLIYXWOPEDX-UHFFFAOYSA-N

物化性质

• 沸点：
  487.7±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole 在 sodium hydrogen sulfide 作用下， 以 aq. buffer 为溶剂， 生成 对氟苯硫酚 、 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol
  参考文献：
  名称：

  Development of Selective Colorimetric Probes for Hydrogen Sulfide Based on Nucleophilic Aromatic Substitution

  摘要：

  Hydrogen sulfide is an important biological signaling molecule and an important environmental target for detection. A major challenge in developing H2S detection methods is separating the often similar reactivity of thiols and other nudeophiles from H2S. To address this need, the nucleophilic aromatic substitution (SNAr) reaction of H2S with electron-poor aromatic electrophiles was developed as a strategy to separate H2S and thiol reactivity. Treatment of aqueous solutions of nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) thioethers with H2S resulted in thiol extrusion and formation of nitrobenzofurazan thiol (lambda(max) = 534 nm). This reactivity allows for unwanted thioether products to be converted to the desired nitrobenzofurazan thiol upon reaction with H2S. The scope of the reaction was investigated using a Hammett linear free energy relationship study, and the determined rho = +0.34 is consistent with the proposed S(N)2Ar reaction mechanism. The efficacy of the developed probes was demonstrated in buffer and in serum with associated submicromolar detection limits as low as 190 nM (buffer) and 380 nM (serum). Furthermore, the sigmoidal response of nitrobenzofurazan electrophiles with H2S can be fit to accurately quantify H2S. The developed detection strategy offers a manifold for H2S detection that we foresee being applied in various future applications.

  DOI：

  10.1021/jo4008095
• 作为产物：
  描述：

  对氟苯硫酚 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 以 乙醇 为溶剂， 反应 0.42h， 以71%的产率得到4-(4-fluorophenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus

  摘要：

  The identification of a novel hit compound inhibitor of the protein-protein interaction between the influenza RNA-polymerase PA and PB1 subunits has been accomplished by means of high-throughput screening. A small family of structurally related molecules has been synthesized and biologically evaluated with most of the compounds showing micromolar potency of inhibition against viral replication. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.048

文献信息

• 2,1,3-BENZOXADIAZOL DERIVATIVES FOR THE INHIBITION OF INFLUENZA A AND B VIRUS AND RESPIRATORY SYNCYTIAL VIRUS REPLICATION
  申请人：Pike Pharma GmbH

  公开号：EP2427442A1

  公开（公告）日：2012-03-14
• Compounds that inhibit human DNA ligases and methods of treating cancer
  申请人：University of Maryland, Baltimore

  公开号：US20140113891A1

  公开（公告）日：2014-04-24

  Methods for treating cancer using compounds that inhibit human DNA ligases. Methods for using compounds that inhibit human DNA ligases to provide insights into the reaction mechanisms of human DNA ligases, for example to identify the human DNA ligase involved in different DNA repair pathways. Screening methods for compounds that inhibit human DNA ligases.
• US8445537B2
  申请人：——

  公开号：US8445537B2

  公开（公告）日：2013-05-21
• US9073896B2
  申请人：——

  公开号：US9073896B2

  公开（公告）日：2015-07-07
• US9664696B1
  申请人：——

  公开号：US9664696B1

  公开（公告）日：2017-05-30