2-[(4-bromophenyl)-hydrazono]malononitrile | 55653-04-8

• 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: 2-[(4-bromophenyl)-hydrazono]malononitrile
• 英文别名: 4-bromophenyl-hydrazonomalononitrile；(4-bromophenyl)carbonohydrazonoyl dicyanide；N-(4-bromophenyl)carbonohydrazonoyl dicyanide；2-[(4-bromophenyl)hydrazinylidene]propanedinitrile
• CAS: 55653-04-8
• 化学式: C₉H₅BrN₄
• 分子量: 249.069
• InChiKey: JJDIGWXKILXPDT-UHFFFAOYSA-N

物化性质

• 沸点：
  337.6±44.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4-bromophenyl)-hydrazono]malononitrile 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 以85%的产率得到4-bromophenylhydrazono-1H-tetrazol-5-yl-acetonitrile
  参考文献：
  名称：

  Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles

  摘要：

  In this study, some substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 2l).

  DOI：

  10.1007/s00044-009-9177-9
• 作为产物：
  描述：

  4-溴苯胺 、 丙二腈 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 2.5h， 以94%的产率得到2-[(4-bromophenyl)-hydrazono]malononitrile
  参考文献：
  名称：

  Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds

  摘要：

  通过微波介导的环化反应获得了4-氨基-3-氰基-N-芳基吡唑，从而实现了各种杂环骨架的多样化合成。

  DOI：

  10.1039/c4ob01951b

文献信息

• Pyrazole compounds
  申请人：——

  公开号：US20030060453A1

  公开（公告）日：2003-03-27

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  提供药物组合物和化合物。发明的化合物显示出抗增殖活性，并且可能促进缺乏正常细胞周期和死亡调控的细胞的凋亡。发明的一个实施例提供了化合物与生理可接受载体组合的药物组合物。该药物组合物可用于治疗过度增殖障碍，包括肿瘤生长、淋巴增殖性疾病、血管生成。发明的化合物是取代吡唑和吡唑啉。
• Iodine-Catalyzed Diazenylation with Arylhydrazine Hydrochlorides in Air
  作者：Dinesh S. Barak、Shashikant U. Dighe、Ilesha Avasthi、Sanjay Batra

  DOI：10.1021/acs.joc.7b03149

  日期：2018.4.6

  A mild approach to diazenylation of active methylene compounds and N-heterocyclic compounds with arylhydrazine hydrochlorides in the presence of iodine under basic aerobic conditions was developed. The reaction could be executed either under heating or in the presence of blue LED light, though the latter condition was found to be relatively efficient. Presumably, the aryldiazene produced by oxidation

  在碱性好氧条件下，在碘的存在下，开发了一种温和的方法，用碘化肼盐酸盐将活性亚甲基化合物和N-杂环化合物二氮杂烯基化。该反应可以在加热下或在蓝色LED灯的存在下进行，尽管发现后者条件是相对有效的。据推测，由芳基肼盐酸盐的氧化反应制得的芳基二氮烯是在碘存在下由活性亚甲基化合物产生的自由基中间体的氮清除剂，以产生重氮化合物。介绍了该协议的范围和局限性。
• Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3
  作者：M. Lourdes Sciú、Victor Sebastián-Pérez、Loreto Martinez-Gonzalez、Rocio Benitez、Daniel I. Perez、Concepción Pérez、Nuria E. Campillo、Ana Martinez、E. Laura Moyano

  DOI：10.1080/14756366.2018.1530223

  日期：2019.1.1

  of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies

  抽象的 大量研究强调了糖原合酶激酶3（GSK-3）在与阿尔茨海默氏病（AD）相关的多个过程中的意义。因此，GSK-3已成为治疗该神经退行性疾病的关键治疗靶标。据此，我们报告了乙基4-氧代-吡唑并[4,3- d] [1-3]三嗪-7-羧酸盐及其作为GSK-3抑制剂的生物学评估。分子建模研究使我们能够开发出优化化学结构的新型支架。还描述了酶中潜在的结合模式测定以及催化位点中关键特征的分析。此外，吡唑并三嗪酮穿越血脑屏障（BBB）的能力通过被动扩散进行了评估，对GSK-3抑制作用强并且渗透到中枢神经系统（CNS）的人表现出对tau蛋白过度磷酸化的神经保护特性。基于模型。这些新的脑可渗透的吡唑并三嗪酮可用于关键的体内研究，并可被视为进一步优化AD治疗的新线索。
• Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds
  作者：Laurent Le Corre、Lotfi Tak-Tak、Arthur Guillard、Guillaume Prestat、Christine Gravier-Pelletier、Patricia Busca

  DOI：10.1039/c4ob01951b

  日期：——

  The obtention of 4-amino-3-cyano-N-arylpyrazoles via a μW mediated cyclization allowed the diversity oriented syntheses of various heteroyclic scaffolds.

  通过微波介导的环化反应获得了4-氨基-3-氰基-N-芳基吡唑，从而实现了各种杂环骨架的多样化合成。
• Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1<i>H</i>-pyrazole-5-carboxylate as an HIV-1 replication inhibitor
  作者：Jeanne Fichez、Cathia Soulie、Laurent Le Corre、Sophie Sayon、Stéphane Priet、Karine Alvarez、Olivier Delelis、Patrick Gizzi、Guillaume Prestat、Christine Gravier-Pelletier、Anne-Geneviève Marcelin、Vincent Calvez、Patricia Busca

  DOI：10.1039/d0md00025f

  日期：——

  screened our in-house library of pyrazole-based compounds to evaluate their in cellulo activity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure–activity-relationship study (SAR) to be built. Further

  受已知基于吡唑的 HIV 抑制剂的抗病毒活性的启发，我们筛选了我们内部的基于吡唑的化合物库，以评估它们在纤维素中对 HIV-1 复制的活性。从单轮和多轮感染测定中显示出具有非常相似结构的两个命中是无毒的并且以剂量依赖性方式具有活性。他们系列的化学扩展允许建立深入和一致的结构-活性-关系研究 (SAR)。进一步的 ADME 评估导致选择了 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1 H-pyrazole-5-carboxylate 具有有利的药代动力学特征。最后，对其作用方式的检查表明，该化合物不属于三种主要的抗 HIV 药物，这是在病毒耐药性背景下最令人感兴趣的特征。