4-[(4-Methoxyphenyl)methylsulfanyl]-2,1,3-benzoxadiazol-7-amine | 1448552-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-[(4-Methoxyphenyl)methylsulfanyl]-2,1,3-benzoxadiazol-7-amine
• 英文别名: 4-[(4-methoxyphenyl)methylsulfanyl]-2,1,3-benzoxadiazol-7-amine
• CAS: 1448552-72-4
• 化学式: C₁₄H₁₃N₃O₂S
• 分子量: 287.342
• InChiKey: LCWCEJAXPUZJLR-UHFFFAOYSA-N

物化性质

• 沸点：
  495.7±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(4-Methoxyphenyl)methylsulfanyl]-2,1,3-benzoxadiazol-7-amine 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.03h， 以75%的产率得到7-(4-methoxybenzylthio)benzo[c][1,2,5]oxadiazol-4-amine hydrochloride
  参考文献：
  名称：

  对抗甲型流感病毒H1N1：苯并呋喃山衍生物作为病毒RNA聚合酶抑制剂的合成，分子建模和生物学评估

  摘要：

  由PA，PB1和PB2三个亚基组成的流感RNA聚合酶复合物是开发新抗病毒药物的有希望的目标。合成了庞大的苯并呋喃化合物文库，并针对流感病毒A / WSN / 33（H1N1）进行了分析。发现大多数新衍生物通过破坏亚基PA和PB1之间形成的复合物来抑制病毒RNA聚合酶复合物而发挥作用。还进行了对接研究，以阐明PA中PB1结合位点内苯并呋喃类的结合方式，并鉴定参与其作用机理的氨基酸。预测的结合姿势与生物学数据完全一致，为合理开发更有效的PA–PB1抑制剂奠定了基础。

  DOI：

  10.1002/cmdc.201300378
• 作为产物：
  描述：

  4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 盐酸 、 铁粉 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.84h， 生成 4-[(4-Methoxyphenyl)methylsulfanyl]-2,1,3-benzoxadiazol-7-amine
  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

• [EN] BENZO[C][1,2,5]OXADIAZOLE FOR THE TREATMENT OF DISEASES CAUSED BY HELICOBACTER<br/>[FR] BENZO [C] [1,2,5] OXADIAZOLE POUR LE TRAITEMENT DE MALADIES PROVOQUÉES PAR HELICOBACTER
  申请人：UNIV ZARAGOZA

  公开号：WO2020234424A1

  公开（公告）日：2020-11-26

  The present invention relates to new compounds which are benzo[c][1,2,5]oxadiazole derivatives, and the use thereof in the treatment of infectious diseases caused by Helicobacter pylori. Also, the present invention relates to a pharmaceutical composition and to a combined preparation both comprising said compounds

  本发明涉及一种新的化合物，即苯并[c][1,2,5]噁二唑衍生物，以及其在治疗由幽门螺杆菌引起的传染病中的应用。此外，本发明涉及一种药物组合物和一种包含该化合物的联合制剂。
• Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against <i>Helicobacter pylori</i> Infection
  作者：Juan J. Galano、Miriam Alías、Reyes Pérez、Adrian Velázquez-Campoy、Paul S. Hoffman、Javier Sancho

  DOI：10.1021/jm400786q

  日期：2013.8.8

  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.
• Design, Synthesis, and Efficacy Testing of Nitroethylene- and 7-Nitrobenzoxadiazol-Based Flavodoxin Inhibitors against <i>Helicobacter pylori</i> Drug-Resistant Clinical Strains and in <i>Helicobacter pylori</i>-Infected Mice
  作者：Sandra Salillas、Miriam Alías、Valérie Michel、Alejandro Mahía、Ainhoa Lucía、Liliana Rodrigues、Jessica Bueno、Juan José Galano-Frutos、Hilde De Reuse、Adrián Velázquez-Campoy、José Alberto Carrodeguas、Carlos Sostres、Javier Castillo、José Antonio Aínsa、María Dolores Díaz-de-Villegas、Ángel Lanas、Eliette Touati、Javier Sancho

  DOI：10.1021/acs.jmedchem.9b00355

  日期：2019.7.11

  Helicobacter pylori (Hp) infection is the main cause of peptic ulcer and gastric cancer. Hp eradication rates have fallen due to increasing bacterial resistance to currently used broad-spectrum antimicrobials. We have designed, synthesized, and tested redox variants of nitroethylene- and 7-nitrobenzoxadiazole-based inhibitors of the essential Hp protein flavodoxin. Derivatives of the 7-nitrobenzoxadiazole lead, carrying reduced forms of the nitro group and/or oxidized forms of a sulfur atom, display high therapeutic indexes against several reference Hp strains. These inhibitors are effective against metronidazole-, clarithromycin-, and rifampicin-resistant Hp clinical isolates. Their toxicity for mice after oral administration is low, and, when administered individually at single daily doses for 8 days in a mice model of Hp infection, they decrease significantly Hp gastric colonization rates and are able to eradicate the infection in up to 60% of the mice. These flavodoxin inhibitors constitute a novel family of Hp-specific antimicrobials that may help fight the constant increase of Hp antimicrobial-resistant strains.
• [EN] BENZO[C][1,2,5]OXADIAZOLE DERIVATIVES FOR TREATING DISEASES CAUSED BY HELICOBACTER<br/>[ES] DERIVADOS DE BENZO[C][1,2,5]OXADIAZOL PARA EL TRATAMIENTO DE ENFERMEDADES CAUSADAS POR HELICOBATER<br/>[FR] DÉRIVÉS DE BENZO[C][1,2,5]OXADIAZOL POUR LE TRAITEMENT DE MALADIES CAUSÉES PAR HELICOBACTER
  申请人：UNIV ZARAGOZA

  公开号：WO2015104433A1

  公开（公告）日：2015-07-16

  La presente invención se refiere a derivados de benzo[c][1,2,5]oxadiazol, además de su uso como antibióticos y más particularmente para el tratamiento y/o prevención de enfermedades causadas por bacterias, particularmente de enfermedades causadas por Helicobacter.
• 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.