3-(2-nitrophenylhydrazono)pentane-2,4-dione | 24756-10-3

• 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: 3-(2-nitrophenylhydrazono)pentane-2,4-dione
• 英文别名: 3-(2-(2-nitrophenyl)hydrazineylidene)pentane-2,4-dione；2,3,4-Pentantrion-3-<2'-nitrophenylhydrazon>；2,3,4-Pentantrion-3-(2-nitro-phenylhydrazon)；2,3,4-Pentantrion-3-(3-nitro-phenyl-hydrazon)；β.δ-Dioxo-γ-(2-nitro-phenylhydrazono)-pentan；pentane-2,3,4-trione 3-[(2-nitro-phenyl)-hydrazone]；Pentan-2,3,4-trion-3-(2-nitro-phenylhydrazon)；3-(2-Nitro-phenylhydrazono)-pentandion-(2.4)；(2-Nitro-benzolazo)-acetylaceton；3-[(2-nitrophenyl)hydrazinylidene]pentane-2,4-dione
• CAS: 24756-10-3
• 化学式: C₁₁H₁₁N₃O₄
• 分子量: 249.226
• InChiKey: NXAYCMAUERMXAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  237 °C(Solv: ethanol (64-17-5))
• 沸点：
  395.2±44.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  101.67
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(2-nitrophenylhydrazono)pentane-2,4-dione 在 氯仿 、 氯 作用下， 生成 C-acetyl-N-(2-nitrophenyl)hydrazidoyl chloride
  参考文献：
  名称：

  196.卤素对芳基偶氮乙酰丙酮的作用

  摘要：

  DOI：

  10.1039/jr9340000930
• 作为产物：
  描述：

  2-硝基苯胺 、 乙酰丙酮 在 盐酸 、 sodium nitrite 、 sodium hydroxide 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以99%的产率得到3-(2-nitrophenylhydrazono)pentane-2,4-dione
  参考文献：
  名称：

  2'-和2'，6'-位的甲基和硝基取代的3-（芳基肼基）戊烷-2,4-二酮的合成及结构研究

  摘要：

  通过戊烷-2,4-二酮与相应的芳基重氮盐之间的Japp–Klingemann反应形成的一系列系统的邻甲基和硝基取代的芳基azo 2–6已合成并通过X射线晶体结构分析进行了研究，并添加了量子化学计算。发现基于DFT计算的最佳分子几何结构，能够确定相关的旋转势垒，并使用“分子中的原子”方法计算出的键和环临界点与实验数据相对应，涉及特定的分子构象和氢邻位键合环结构-取代，因此使对该化合物类别的可靠结构预测成为可能。版权所有©2007 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1225

文献信息

• Arylazo‐3,5‐dimethylisoxazoles: Azoheteroarene Photoswitches Exhibiting High <i>Z</i> ‐Isomer Stability, Solid‐State Photochromism, and Reversible Light‐Induced Phase Transition
  作者：Pravesh Kumar、Anjali Srivastava、Chitranjan Sah、Sudha Devi、Sugumar Venkataramani

  DOI：10.1002/chem.201902150

  日期：2019.9.12

  contrasting color changes in solution and the solid state. Besides, many of the derivatives exhibit partial phase transition upon UV irradiation. The highlight of this class of photoswitches is the reversible light-induced phase transition between solid and liquid phases in the parent compound, which can be used in patterned crystallization. These results show that this new class of azoheteroarene based photoswitches

  合成了可逆光转换的苯基偶氮-3,5-二甲基异恶唑和37个芳基取代的衍生物。这些化合物在溶液和固态中具有出色的光开关能力。通过借助于NMR光谱的动力学研究，证明了高的Z-异构体稳定性。有趣的是，大多数衍生物在溶液和固态中显示出光诱导的对比色变化。此外，许多衍生物在紫外线照射下表现出部分相变。这类光开关的亮点是母体化合物中固相和液相之间可逆的光诱导相变，可用于图案化结晶。这些结果表明，这种基于偶氮杂芳烃的新型光开关具有在各种领域中有用的机会。
• Synthesis of substituted dihydro-1H-pyrazoles and 1H-pyrazoles via formal [4+1] annulation of α-arylhydrazonoketones and dimethyl sulfonium methylides
  作者：Bicheng Deng、Chaoran Li、Jingwen Yuan、Chitturi Bhujanga Rao、Yanning Zhao、Rui Zhang、Dewen Dong

  DOI：10.1016/j.tet.2019.01.061

  日期：2019.4

  formal [4+1] annulation of readily available α-arylhydrazonoketones and dimethyl sulfonium methylides is described, which involving tandem ylide-mediated addition and nucleophilic cyclization reactions. This transformation features mild reaction conditions, simple execution, good to high yields, and provides straightforward synthesis of substituted dihydro-1H-pyrazoles and 1H-pyrazoles via C-C and

  描述了易于获得的α-芳基肼酮和二甲基sulf亚甲基化的正式[4 + 1]环化反应，涉及串联叶立德介导的加成反应和亲核环化反应。这种转变提供反应条件温和，简单执行，良好的产量高，并且提供被取代的二氢1的简单的合成ħ -pyrazoles和1所ħ -pyrazoles经由Ç - Ç和CN键形成。
• New 3,4,5-trisubstituted isoxazole derivatives with potential biological properties
  作者：Carlos Bustos、Elies Molins、Juan-Guillermo Cárcamo、Marcelo N. Aguilar、Christian Sánchez、Ignacio Moreno-Villoslada、Hiroyuki Nishide、Angela Mesías-Salazar、Ximena Zarate、Eduardo Schott

  DOI：10.1039/c4nj02427c

  日期：——

  Synthesis of (E)-3,5-dimethyl-4-(R-phenyldiazenyl)isoxazoles was carried out by reacting β-diketohydrazones (R-C6H4-NHNC(COCH3)2) with hydroxylammonium chloride, where R = 4-N(CH3)2(1), 4-OH(2), 4-CH3(3), 4-OCH3(4), 4-H(5), 4-Cl(6) 4-Br(7), 4-CO2H(8), 4-CO2CH2CH3(9), 4-COCH3(10), 4-CN(11), 4-NO2(12), 4-CH2CO2CH2CH3(13), 3-Cl(14), 2-OH(15), 2-Cl(16), 2-NO2(17), 2-CO2H(18). All compounds were characterized

  （E）-3,5-二甲基-4-（R-苯基二氮烯基）异恶唑的合成是通过将β-二酮hydr（R -C 6 H 4 -NHN C（COCH 3）2）与羟基氯化铵反应进行的，其中R = 4-N（CH 3）2（1），4-OH（2），4-CH 3（3），4-OCH 3（4），4-H（5），4-Cl（6）4 -Br（7），4-CO 2 H（8），4-CO 2 CH2 CH 3（ 9），4-COCH 3（ 10），4-CN（ 11），4-NO 2（ 12），4-CH 2 CO 2 CH 2 CH 3（ 13），3-Cl（ 14） ，2-OH（ 15），2-Cl（ 16），2-NO 2（ 17），2-CO 2 H（ 18）。所有化合物均通过EA和分光光度法进行表征。化合物（ 7）和（ 17）中的两种的晶体结构），通过X射线衍射法解决。进行DFT和TDDFT计算是为了表征跃迁中涉及的分子几何形状和分子轨道。此外
• Reaction of 2, 3, 4-pentantrione-3-arylhydrazones with<i>N, N</i>-dimethylhydrazine: Formation of substituted 1<i>H</i>-pyrazoles<i>via</i>demethylation
  作者：Himatkumar V. Patel、Kavita A. Vyas、Sudhanshu P. Pandey、Peter S. Fernandes

  DOI：10.1080/00397919209409257

  日期：1992.11

  A novel one-step synthesis of 4-arylazo-1H-1,3,5-trimethylpyrazoles is accomplished by reaction of N,N-dimethylhydrazine with 2,3,4-pentantrione-3-arylhydrazones via an unusual demethylation.
• 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma
  作者：Anisha Viswanathan、Dinesh Kute、Aliyu Musa、Saravanan Konda Mani、Vili Sipilä、Frank Emmert-Streib、Fedor I. Zubkov、Atash V. Gurbanov、Olli Yli-Harja、Meenakshisundaram Kandhavelu

  DOI：10.1016/j.ejmech.2019.01.021

  日期：2019.3

  Nerve growth factor receptor (NGFR), a member of kinase protein, is emerging as an important target for Glioblastoma (GBM) treatment. Overexpression of NGFR is observed in many metastatic cancers including GBM, promoting tumor migration and invasion. Hydrazones have been reported to effectively interact with receptor tyrosine kinases (RTKs). We report herein the synthesis of 23 arylhydrazones of active methylene compounds (AHAMCs) compounds and their anti-proliferative activity against GBM cell lines, LN229 and U87. Compound 8234, 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile, was identified as the most active anti-neoplastic compound, with the IC50 value ranging 87 mu M - 107 mu M Molecular docking simulations of the synthesized compounds into the active site of tyrosine receptor kinase A (TrkA), demonstrated a strong binding affinity with 8234 and concurs well with the obtained biological results. 8234 was found to be a negative regulator of PI3K/Akt/mTOR pathway and an enhancer of p53 expression. In addition, 8234 treated GBM cells exhibited the downregulation of cyclins, cyclin-dependent kinases and other key molecules involved in cell cycle such as CCNE, E2F, CCND, CDK6, indicating that 8234 induces cell cycle arrest at G1/S. R234 also exerted its apoptotic effects independent of caspase3/7 activity, in both cell lines. In U87 cells, 8234 induced oxidative effects whereas LN229 cells annulled oxidative stress. The study thus concludes that 8234, being a negative modulator of RTKs and cell cycle inhibitor, may represent a novel class of anti-GBM drugs. (C) 2019 Elsevier Masson SAS. All rights reserved.