4-(4-methoxyphenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole | 53619-62-8

• 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-methoxyphenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole
• 英文别名: 7-(4-methoxyphenylthio)-4-nitrobenzofurazan；4-(4-Methoxyphenyl)sulfanyl-7-nitro-2,1,3-benzoxadiazole
• CAS: 53619-62-8
• 化学式: C₁₃H₉N₃O₄S
• 分子量: 303.298
• InChiKey: KQMVBJBEJZHNEM-UHFFFAOYSA-N

物化性质

• 沸点：
  514.7±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole 在 sodium hydrogen sulfide 作用下， 以 aq. buffer 为溶剂， 生成 4-甲氧基苯硫酚 、 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：

  4-甲氧基苯硫酚 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 三乙胺 作用下， 以67%的产率得到4-(4-methoxyphenylthio)-7-nitrobenzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection

  摘要：

  Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.

  DOI：

  10.1021/jm400786q

文献信息

• Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus
  作者：Ulrich Kessler、Daniele Castagnolo、Mafalda Pagano、Davide Deodato、Martina Bernardini、Beatrice Pilger、Charlene Ranadheera、Maurizio Botta

  DOI：10.1016/j.bmcl.2013.08.048

  日期：2013.10

  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.
• Rosso, Mauro Domenico del; Nunno, Leonardo Di; Florio, Saverio, Journal of the Chemical Society. Perkin transactions II, 1980, p. 239 - 242
  作者：Rosso, Mauro Domenico del、Nunno, Leonardo Di、Florio, Saverio、Amorese, Antonio

  DOI：——

  日期：——
• US9664696B1
  申请人：——

  公开号：US9664696B1

  公开（公告）日：2017-05-30