[2-(2-硝基苯基)亚肼基]丙二腈 | 55653-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [2-(2-硝基苯基)亚肼基]丙二腈
• 英文名称: 2-[(2-nitrophenyl)hydrazono]malononitrile
• 英文别名: Carbonyl cyanide 2-nitrophenylhydrazone；2-[(2-nitrophenyl)hydrazinylidene]propanedinitrile
• CAS: 55653-13-9
• 化学式: C₉H₅N₅O₂
• mdl: MFCD00784670
• 分子量: 215.171
• InChiKey: NKWOBFAONPVDDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 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：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(2-硝基苯基)亚肼基]丙二腈 在 一水合肼 作用下， 生成 4-(o-nitrophenylazo)-3,5-diamino-1H-pyrazole
  参考文献：
  名称：

  含有吡唑和苯基吡唑的新型杂环二偶氮染料。第1部分：合成，表征，溶剂极性和酸碱敏感性特征

  摘要：

  在0〜5℃下，将一系列重氮化的苯胺和苯胺衍生物与丙二腈在吡啶中的溶液反应，得到1a-1m的化合物。然后通过将芳基偶氮丙二腈化合物与肼偶合来合成4-芳基偶氮-3，5-二氨基-1H-吡唑（2a-2m）衍生物。最后，将合成的吡唑衍生物2a-2m化合物再次重氮化。通过使这些重氮化的化合物与3-氨基-5-羟基-1-苯基吡唑反应，得到了新的13种杂环二偶氮染料（3a-3m）加入了染料文献和染料行业。这些新合成的化合物的结构通过元素分析和光谱方法进行表征，例如傅立叶变换红外光谱-原子吸收全反射率（FT-IR-ATR），1 H-核磁共振（1 H NMR）光谱和质谱。然后研究了在二甲基亚砜，二甲基甲酰胺，乙腈，乙酸，甲醇和氯仿中的溶剂变色性质和溶剂作用。此外，研究了有机和无机酸和碱对化合物吸收光谱的影响以及苯环键合基团的取代作用。

  DOI：

  10.1016/j.molstruc.2021.129960
• 作为产物：
  描述：

  2-硝基苯胺 、 丙二腈 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 2.5h， 以88%的产率得到[2-(2-硝基苯基)亚肼基]丙二腈
  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

• 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。
• Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles
  作者：Serkan Yavuz、Özlem Aydın、Servet Çete、Ali Dişli、Yılmaz Yıldırır

  DOI：10.1007/s00044-009-9177-9

  日期：2010.3

  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).
• 4-Arylazo-3,5-diamino-1<i>H</i>-pyrazole CDK Inhibitors:  SAR Study, Crystal Structure in Complex with CDK2, Selectivity, and Cellular Effects
  作者：Vladimír Kryštof、Petr Cankař、Iveta Fryšová、Jan Slouka、George Kontopidis、Petr Džubák、Marián Hajdúch、Josef Srovnal、Walter F. de Azevedo、Martin Orság、Martina Paprskářová、Jakub Rolčík、Aleš Látr、Peter M. Fischer、Miroslav Strnad

  DOI：10.1021/jm0605740

  日期：2006.11.1

  In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl] phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.
• Rymareva; Torgasheva; Zelikhover, Russian Journal of General Chemistry, 1997, vol. 67, # 9, p. 1417 - 1423
  作者：Rymareva、Torgasheva、Zelikhover、Bel'skii

  DOI：——

  日期：——
• Sturdik, Ernest; Durcova, Edita; Mikes, Vladimir, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 11, p. 2819 - 2825
  作者：Sturdik, Ernest、Durcova, Edita、Mikes, Vladimir、Dadak, Vladimir、Balaz, Stefan、et al.

  DOI：——

  日期：——