4-bromo-N-[1-(4-nitrophenyl)ethylideneamino]aniline | 444771-86-2

• 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-bromo-N-[1-(4-nitrophenyl)ethylideneamino]aniline
• CAS: 444771-86-2
• 化学式: C₁₄H₁₂BrN₃O₂
• 分子量: 334.172
• InChiKey: DNFFVIXNXOMPDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  445.5±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-N-[1-(4-nitrophenyl)ethylideneamino]aniline 在 hydrazine hydrate 、 potassium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 25.25h， 生成 1-(4-bromophenyl)-3-(4-nitrophenyl)-4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)pyrazole
  参考文献：
  名称：

  New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents

  摘要：

  A new series of pyrazole derivatives were synthesized by hybridization with five-membered heterocyclic moieties such as thiazoles, thiazolidinones, 1,3,4-thiadiazoles and pyrazolines. The compounds were evaluated for their in vivo antimalarial activity against Plasmodium berghei infected mice and the most active derivatives were further examined for their in vitro antimalarial activity against chloroquine resistant (RKL9) strain of Plasmodium falciparum. Compounds 2c, 2d, 4b, 4c, 4d, 5a, 6c, 8c and 9b had more than 90% parasite suppression activity of that found with the antimalarial reference standard drug, chloroquine phosphate and had lower IC50 values than chloroquine. Compounds 4b and 9b were the most active derivatives, and their activities were 5-fold higher than chloroquine. All the newly synthesized compounds were evaluated for their in vitro antileishmanial activity against Leishmania aethiopica promastigotes and amastigote. The results showed that compounds 2c, 2d, 3d, 4b, 4c, 4d and 5a had lower or similar IC50 values than the reference standard drugs, amphotericin B and miltefosine. Compound 3d had the highest antileishmanial activity. Collectively, compounds 2c, 2d, 4b, 4c, 4d and 5a exhibited dual activity against malaria and leishmaniasis and were safe and well tolerated by the experimental animals orally up to 300 mg/kg and parenterally up to 100 mg/kg. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.038
• 作为产物：
  描述：

  对硝基苯乙酮 、 对溴苯肼 以 乙醇 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 4-bromo-N-[1-(4-nitrophenyl)ethylideneamino]aniline
  参考文献：
  名称：

  [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  [FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C

  摘要：

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。

  公开号：

  WO2010111483A1

文献信息

• [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111483A1

  公开（公告）日：2010-09-30

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• 10.1016/j.molstruc.2024.139350
  作者：Sultana, Razia、Ali, Asghar、Rana, Manish、Ahmad, Iqbal、Kamthan, Mohan、Nouman、Mehandi, Rabiya、Rahisuddin

  DOI：10.1016/j.molstruc.2024.139350

  日期：——

  1,3,4-Oxadiazole derivatives containing pyrazole moiety 5a–5l and amine substituted oxadiazole derivatives 5m-5p were synthesized and also characterized by spectroscopic methods such as FT-IR, 1H, 13C NMR spectroscopy, and mass spectrometry. Compounds 5a–5p were tested for their in vitro antibacterial activity against gram-positive (Bacillus subtilis and Staphylococcus aureus) and gram-negative (Pseudomonas

  合成了含有吡唑部分 5a-5l 和胺取代的噁二唑衍生物 5m-5p 的 1,3,4-噁二唑衍生物，并通过 FT-IR、1H、13C NMR 波谱和质谱等光谱方法进行了表征。与药物环丙沙星 （CIP） 相比，使用琼脂孔盘扩散法测试化合物 5a-5p 对革兰氏阳性（枯草芽孢杆菌和金黄色葡萄球菌）和革兰氏阴性（铜绿假单胞菌和大肠杆菌）细菌菌株的体外抗菌活性。被认为通过使用吸收滴定、发射滴定、圆二色谱、与 EtBr 的竞争性结合和循环伏安法研究了最活跃的类似物 5e 和 5f 与 CT-DNA 相互作用的能力，结果表明化合物通过嵌入模式与 CT-DNA 结合。发现 5e 和 5f 的结合常数 （Kb） 分别为 1.07 × 105 和 1.30 × 105。从荧光光谱中进一步发现 5e 和 5f 的线性 Stern-Volmer 常数 （Kf） 分别为 1.84 × 105、4.3 × 105。薛定谔版本
• Synthesis, spectral characterization of pyrazole derived Schiff base analogs: molecular dynamic simulation, antibacterial and DNA binding studies
  作者：Razia Sultana、Asghar Ali、Charmy Twala、Rabiya Mehandi、Manish Rana、Daraksha Yameen、Mohammad Abid、Rahisuddin

  DOI：10.1080/07391102.2023.2179541

  日期：——
• INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20190127365A1

  公开（公告）日：2019-05-02

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种具有式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• New heterocyclic hybrids of pyrazole and its bioisosteres: Design, synthesis and biological evaluation as dual acting antimalarial-antileishmanial agents
  作者：Adnan A. Bekhit、Ahmed M.M. Hassan、Heba A. Abd El Razik、Mostafa M.M. El-Miligy、Eman J. El-Agroudy、Alaa El-Din A. Bekhit

  DOI：10.1016/j.ejmech.2015.02.038

  日期：2015.4

  A new series of pyrazole derivatives were synthesized by hybridization with five-membered heterocyclic moieties such as thiazoles, thiazolidinones, 1,3,4-thiadiazoles and pyrazolines. The compounds were evaluated for their in vivo antimalarial activity against Plasmodium berghei infected mice and the most active derivatives were further examined for their in vitro antimalarial activity against chloroquine resistant (RKL9) strain of Plasmodium falciparum. Compounds 2c, 2d, 4b, 4c, 4d, 5a, 6c, 8c and 9b had more than 90% parasite suppression activity of that found with the antimalarial reference standard drug, chloroquine phosphate and had lower IC50 values than chloroquine. Compounds 4b and 9b were the most active derivatives, and their activities were 5-fold higher than chloroquine. All the newly synthesized compounds were evaluated for their in vitro antileishmanial activity against Leishmania aethiopica promastigotes and amastigote. The results showed that compounds 2c, 2d, 3d, 4b, 4c, 4d and 5a had lower or similar IC50 values than the reference standard drugs, amphotericin B and miltefosine. Compound 3d had the highest antileishmanial activity. Collectively, compounds 2c, 2d, 4b, 4c, 4d and 5a exhibited dual activity against malaria and leishmaniasis and were safe and well tolerated by the experimental animals orally up to 300 mg/kg and parenterally up to 100 mg/kg. (C) 2015 Elsevier Masson SAS. All rights reserved.