(E)-4-nitro-N'-(4-nitrobenzylidene)benzohydrazide | 51771-32-5

• 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)-4-nitro-N'-(4-nitrobenzylidene)benzohydrazide
• 英文别名: 4-nitro-benzoic acid-(4-nitro-benzylidenehydrazide)；4-Nitro-benzoesaeure-(4-nitro-benzylidenhydrazid)；(4-Nitro-benzal)-4-nitro-benzhydrazid；4-Nitro-benzaldehyd-(4-nitro-benzoylhydrazon)；4-nitro-N'-[(E)-(4-nitrophenyl)methylidene]benzohydrazide；4-nitro-N-[(E)-(4-nitrophenyl)methylideneamino]benzamide
• CAS: 51771-32-5
• 化学式: C₁₄H₁₀N₄O₅
• 分子量: 314.257
• InChiKey: RHCJSSRUUPNHBF-OQLLNIDSSA-N

物化性质

• 熔点：
  164 °C(Solv: ethanol (64-17-5))
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 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：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对硝基苯甲酸甲酯 在 cobalt(II) diacetate tetrahydrate 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (E)-4-nitro-N'-(4-nitrobenzylidene)benzohydrazide
  参考文献：
  名称：

  温和条件下乙酸 Co(II) 辅助酰肼直接合成酰腙

  摘要：

  以弱碱K 2 CO 3和市售Co(OAc) 2 .4H 2 O盐为催化剂，在温和条件下，实现了一种原子经济且高效的由酰肼制备多动力酰基（芳基和杂芳基）腙的方法。反应条件以甲醇为溶剂。此外，一些新型酰基腙的E/Z光开关行为已被紫外-可见光谱证实。

  DOI：

  10.1002/asia.202300755

文献信息

• Curtius; Melsbach, Journal fur praktische Chemie (Leipzig 1954), 1910, vol. <2> 81, p. 536
  作者：Curtius、Melsbach

  DOI：——

  日期：——
• 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.
• Co(II) Acetate‐Assisted Direct Synthesis of Acyl Hydrazones from Acyl Hydrazides under Mild Conditions
  作者：Adwitiya Pal、Krishna Mohan Das、Subham Sau、Arunabha Thakur

  DOI：10.1002/asia.202300755

  日期：2023.11.16

  efficient method to prepare multi-dynamic acyl (aryl and heteroaryl) hydrazones from acyl hydrazides has been achieved by using mild base K2CO3 and commercially available Co(OAc)2.4H2O salt as catalyst under mild reaction conditions with methanol as solvent. Additionally, the E/Z photoswitching behavior of some of the new acyl hydrazones has been witnessed by UV-vis spectroscopy.

  以弱碱K 2 CO 3和市售Co(OAc) 2 .4H 2 O盐为催化剂，在温和条件下，实现了一种原子经济且高效的由酰肼制备多动力酰基（芳基和杂芳基）腙的方法。反应条件以甲醇为溶剂。此外，一些新型酰基腙的E/Z光开关行为已被紫外-可见光谱证实。