(E)-N'-benzylidene-4-nitrobenzohydrazide | 7462-01-3

• 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: (E)-N'-benzylidene-4-nitrobenzohydrazide
• 英文别名: N'-benzylidene-4-nitrobenzohydrazide；N-[(E)-benzylideneamino]-4-nitrobenzamide
• CAS: 7462-01-3
• 化学式: C₁₄H₁₁N₃O₃
• 分子量: 269.26
• InChiKey: IXZPFOAOCXACKD-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (E)-N'-benzylidene-4-nitrobenzohydrazide 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(4-aminobenzoyl)-2-benzalhydrazine
  参考文献：
  名称：

  Discovery of novel thymidylate synthase (TS) inhibitors that influence cancer angiogenesis and metabolic reprogramming in NSCLC cells

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115600
• 作为产物：
  描述：

  对硝基苯甲酸甲酯 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 16.0h， 生成 (E)-N'-benzylidene-4-nitrobenzohydrazide
  参考文献：
  名称：

  Discovery of novel thymidylate synthase (TS) inhibitors that influence cancer angiogenesis and metabolic reprogramming in NSCLC cells

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115600

文献信息

• Comparative studies on the pyrolysis ofN-arylideneaminoamides: Kinetic and mechanistic studies
  作者：Nouria A. Al-Awadi、Yehia A. Ibrahim、Mehul Patel、Bobby J. George、Alya M. Al-Etiabi

  DOI：10.1002/kin.20219

  日期：2007.2

  Rates of thermal decomposition of title compounds have been measured using a static reaction system. They undergo a unimolecular first-order elimination to give arylnitrile and the corresponding substituted amides. The decomposition parallels that of N-arylidenamino cyclic amide. The relative elimination rates at 600 K were calculated. The kinetic data reveal that the electronic effects of substituents

  使用静态反应系统测量了标题化合物的热分解速率。它们经历单分子一级消除，得到芳腈和相应的取代酰胺。分解与 N-芳基氨基环酰胺的分解相似。计算了 600 K 时的相对消除率。动力学数据表明，甲基、苯基、苄基和烯丙基等取代基的电子效应与亚芳基氮原子上的孤对电子离域的相反方向有关。© 2006 Wiley Periodicals, Inc. Int J Chem Kinet 39: 59–66, 2007
• Lanthanide–EDTA complexes covalently bonded on Fe₃O₄@SiO₂ magnetic nanoparticles promote the green, stereoselective synthesis of <i>N</i>-acylhydrazones
  作者：João Batista M. de Resende Filho、Nathália Kellyne S. M. Falcão、Gilvan P. Pires、Luiz Fernando S. de Vasconcelos、Sávio M. Pinheiro、José Maurício dos Santos Filho、Marília Imaculada Frazão Barbosa、Antônio Carlos Doriguetto、Ercules E. S. Teotonio、Juliana A. Vale

  DOI：10.1039/c9nj02916h

  日期：——

  and applicability of green procedures. In this work, lanthanide–EDTA complexes covalently bonded on Fe3O4@SiO2 magnetic nanoparticles (Fe3O4@SiO2-xN-EDTA–Ln3+, with x = 1, 2, or 3 N spacer groups, and Ln3+ = La3+, Ce3+, Sm3+, Eu3+, Gd3+, Tb3+, Er3+ or Yb3+) were prepared and investigated as a heterogeneous catalyst for the synthesis of N-acylhydrazones. The target molecules were obtained in good to excellent

  在最近几年中，已经开发出许多使用磁性纳米材料基催化剂的合成方法，这些方法对于绿色工艺的效率，选择性和适用性具有相当大的优势。在这项工作中，镧系元素-EDTA络合物共价键合在Fe 3 O 4 @SiO 2磁性纳米颗粒上（Fe 3 O 4 @SiO 2 - x N-EDTA-Ln 3+，其中x = 1、2或3 N间隔基并且Ln 3+ = La 3+，Ce 3+，Sm 3+，Eu 3+，Gd 3+，Tb 3+，Er制备了3+或Yb 3+）并作为合成N-酰基hydr的非均相催化剂进行了研究。在温和条件下反应时间短，易回收催化剂的浓度低后，仅以E-非对映异构体的形式获得了高至优异收率的目标分子。
• Towards a Catalytic Asymmetric Version of the [3+2] Cycloaddition between Hydrazones and Cyclopentadiene
  作者：Svetlana Tsogoeva、Alexandru Zamfir

  DOI：10.1055/s-0030-1260467

  日期：2011.6

  ved silicon Lewis acid, has been described for the [3+2] cycloaddition of N-benzoylhydrazone to cyclopentadiene to afford a cycloadduct in high dia­stereomeric ratio of 95:5 (syn/anti) and enantiomeric excess of 89%. These results provide insights in the future design and development of highly active and enantioselective silicon Lewis acids for this and other cycloaddition types. cycloaddition - silicon

  已经描述了一种新颖且易于获得的无金属催化体系，即原位生成的BINOL-磷酸盐衍生的硅路易斯酸，用于N-苯甲酰hydr的[3 + 2]环加成反应生成环戊二烯，从而以高非对映异构体比例提供环加合物。 95：5（syn / anti）和对映体过量89％。这些结果为这种和其他环加成类型的高活性和对映选择性硅路易斯酸的未来设计和开发提供了见识。 环加成-硅-hydr-路易斯酸-氮杂环
• Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists
  作者：Mohamed Shahien、Mohamed Elagawany、Sadichha Sitaula、Shaimaa S. Goher、Sheryl L. Burris、Ryan Sanders、Amer Avdagic、Cyrielle Billon、Lamees Hegazy、Thomas P. Burris、Bahaa Elgendy

  DOI：10.1016/j.bioorg.2020.104079

  日期：2020.9

  Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERR alpha emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERR beta/gamma selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERR alpha agonism. We successfully engineered high affinity ERR alpha agonism into a chemical scaffold that displays selective ERR beta/gamma agonist activity (GSK4716), providing novel ERR alpha/beta/gamma pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERR alpha. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERR alpha and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1 alpha and PGC-1 beta, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.
• FLOWERS W. T.; ROBINSON J. F.; TOYLOR D. R.; TIPPING A. E., J. CHEM. SOC. PERKIN TRANS., PART 1, 1981, NO 2, 349-355
  作者：FLOWERS W. T.、 ROBINSON J. F.、 TOYLOR D. R.、 TIPPING A. E.

  DOI：——

  日期：——