4-carboxyl phenyl-hydrazono-ethyl-2,3-dioxobutyrate | 34582-83-7

• 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: 4-carboxyl phenyl-hydrazono-ethyl-2,3-dioxobutyrate
• 英文别名: ethyl 2-(4-carboxyphenyl)hydrazono-3-oxobutyrate；4-[2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazin-yl]benzoic acid；4-[N'-(1-ethoxycarbonyl-2-oxo-propylidene)-hydrazino]-benzoic acid；4-[2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyl]benzoic acid
• CAS: 34582-83-7
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: XRKXRANKVWFPCU-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C(Solv: ethanol (64-17-5))
• 沸点：
  439.4±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  105.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-carboxyl phenyl-hydrazono-ethyl-2,3-dioxobutyrate 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以58.5%的产率得到(Z)-4-(2-(3-methyl-5-oxoisoxazol-4(5H)-ylidene)hydrazinyl)benzoic acid
  参考文献：
  名称：

  一族具有潜在生物学特性的取代肼基异恶唑酮

  摘要：

  已经报道了一种新的3,4,5-三取代异恶唑酮的合成，表征和生物学研究，从而研究了一系列（Z）-3-甲基-4-（2-（R-苯基）苯二甲叉基）异恶唑-5（通过β-二酮hydr与氯化铵反应制备了4 H）-one。所有产品均使用EA，UV-Vis，FT-IR，1 H-NMR，13进行表征C-NMR光谱和HMBC。通过X射线衍射方法解析了三种化合物的晶体和分子结构。进行密度泛函理论（DFT）和时变DFT（TDDFT）计算，以更好地解释这些新合成的化合物的实验行为。此外，通过MTT还原法测试了在人早幼粒细胞白血病细胞HL-60中的细胞毒性和抗增殖作用的报道，表明大多数新合成的化合物具有重要的抗肿瘤活性。最活跃isoxazolones是在反转录聚合酶链反应（RT-PCR）实验中使用，以确定对表达水平的影响米使用抗凋亡Bcl 2，促凋亡Bax和增殖抑制蛋白p21 WAF-1编码的RNA 。因此，有可能完全

  DOI：

  10.1039/c5nj02604k
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对氨基苯甲酸 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 4-carboxyl phenyl-hydrazono-ethyl-2,3-dioxobutyrate
  参考文献：
  名称：

  芳香族氨基酸的杂环化：融合，非融合和螺多杂环衍生物的新型合成和抗菌活性。

  摘要：

  摘要可商购的p氨基苯甲酸被用作新颖的稠合的合成的前体，非稠合，螺环和多杂环衍生物轴承茚，咪唑，吡唑，和/或经由除了简单和方便的试剂如茚三酮，三嗪核ö -苯二胺和二硫化碳。实验步骤简单明了，分离出的产品收率为15–86％，并且。通过光谱数据证实了它们的结构。评价合成的化合物对某些革兰氏阳性和革兰氏阴性细菌的抗菌活性。

  DOI：

  10.1134/s1070428020060159

文献信息

• Synthesis of arylhydrazone-based molecular switches using aryldiazonium silica sulfate nanocomposites and analysis of their isomerization
  作者：Amin Zarei、Leila Khazdooz、Solmaz Soltani、Alireza Najafi Chermahini、Hamidreza Aghaei、Alireza Abbaspourrad

  DOI：10.1016/j.dyepig.2021.109544

  日期：2021.10

  each synthesized compound in these two solvents. By changing the solvent from CHCl3 to DMSO, the E/Z ratios decreased. The results demonstrated that the ΔG° values for the formation of Z isomers were more negative than those of the E isomers in DMSO. This is why Z isomers are more stable than E isomers in DMSO. The results of density functional theory (DFT) calculations at B3LYP/6–311++G (d,p) level

  报道了一种通过芳基重氮硅硫酸盐纳米复合材料与丙二腈、乙酰乙酸乙酯和二甲酮反应来合成一系列芳基腙的快速有效方法。所有反应均在室温下在水中进行，相应的产物以 77-87% 的产率获得。使用乙酰乙酸乙酯合成的芳基腙中存在两种分子内氢键，使这些化合物能够通过围绕腙C N 键旋转而转换，从而导致它们的E和Z构型之间的可逆异构化。这种转换可以通过改变溶剂的极性来控制。在 CHCl 3 中研究了每种合成化合物的E/Z比和二甲基亚砜。E/Z的比率是使用1 H NMR 数据在 CDCl 3和 DMSO- d 6中计算的，并用于计算每种合成化合物在这两种溶剂中的EZ异构化的ΔG ° 。通过将溶剂从 CHCl 3改为 DMSO，E/Z比降低。结果表明，在 DMSO 中形成Z异构体的 Δ G ° 值比E异构体的更负。这就是为什么Z异构体比E更稳定DMSO 中的异构体。B3LYP/6–311++G (d,p) 理论水平的密度泛函理论
• An efficient one-pot synthesis of pyrazolyl-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazin-6-yl)-2H-pyran-2-one derivatives via multicomponent approach and their potential antimicrobial and nematicidal activities
  作者：Santhosh Penta、Kranthi Kumar Gadidasu、Srinivas Basavoju、Vedula Rajeswar Rao

  DOI：10.1016/j.tetlet.2013.07.148

  日期：2013.10

  -2-one derivatives have been efficiently synthesized in excellent yields via one-pot, multi-component approach. The importance of this methodology is that in a one-pot operation four new bonds (3C–N and 1C–S) are generated. The structure of compound 5a was confirmed by single-crystal X-ray diffraction. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against

  一系列简单和/或芳基，亚肼基heteryl吡唑基- [1,2,4]三唑并[3,4的b ] [1,3,4]噻二嗪-6-基）-2- ħ -吡喃-2-酮通过一锅多组分方法，可以高效合成高产率的衍生物。这种方法的重要性在于，在一锅操作中会生成四个新的键（3C–N和1C–S）。化合物5a的结构通过单晶X射线衍射确认。新合成的化合物其在体外对革兰氏阳性细菌（抗微生物活性进行评价金黄色葡萄球菌和枯草芽孢杆菌），革兰氏阴性细菌（大肠埃希氏菌和克氏杆菌肺炎），针对抗真菌活性白色念珠菌，以及对杀线虫活性南方根结线虫。在所有化合物中，6f对被测细菌，真菌和线虫均显示出优异的抗菌和杀线虫活性。
• Synthesis and biological evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives
  作者：P. Horrocks、M. R. Pickard、H. H. Parekh、S. P. Patel、Ravindra B. Pathak

  DOI：10.1039/c3ob27290g

  日期：——

  3-(4-Chlorophenyl)-4-substituted pyrazole derivatives were synthesised and tested for their in vitro antifungal activity. Some compounds showed very good antifungal activity against four pathogenic strains of fungi. The same compounds exhibited an interesting activity against the tested strain of Mycobacterium tuberculosis H37Rv. The results suggest that 1,3,4-oxadiazoles and 5-pyrazolinones bearing

  合成了3-（4-氯苯基）-4-取代的吡唑衍生物，并测试了它们的体外抗真菌活性。一些化合物对四种病原性真菌显示出非常好的抗真菌活性。相同的化合物对测试的结核分枝杆菌H37Rv菌株表现出令人感兴趣的活性。结果表明，带有核心吡唑支架的1,3,4-恶二唑和5-吡唑啉酮可能是有前途的抗真菌和抗结核药。
• Regioselective CC bond cleavage in arylhydrazones of 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-diones
  作者：Reza Solhnejad、Farqana S. Aliyeva、Abel M. Maharramov、Rafiga A. Aliyeva、Famil M. Chyragov、Atash V. Gurbanov、Kamran T. Mahmudov、Maximilian N. Kopylovich

  DOI：10.1016/j.molstruc.2013.07.035

  日期：2013.10

  New (Z)-2-(2-(para-substituted phenyl)hydrazono)-4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-diones with chloro (1), bromo (2) and carboxy (3) substituents were synthesized and characterized by ESI-MS, IR, H-1 and C-13 NMR spectroscopies and elemental analysis. The regioselective carbon-carbon bond cleavage with the formation (E)-2-(2-(4-substituted phenyl) hydrazono)-1-(thiophen-2-yl)ethanones was achieved upon heating (80 degrees C) of 1-3 in methanol-water. Crown Copyright (C) 2013 Published by Elsevier B.V. All rights reserved.
• Design, synthesis, analgesic, anti-inflammatory activity of novel pyrazolones possessing aminosulfonyl pharmacophore as inhibitors of COX-2/5-LOX enzymes: Histopathological and docking studies
  作者：Mohamed A. Abdelgawad、Madlen B. Labib、Waleed A.M. Ali、Gehan Kamel、Amany A. Azouz、EL-Shaymaa EL-Nahass

  DOI：10.1016/j.bioorg.2018.03.011

  日期：2018.8

  A series of newly synthesized 4-aryl-hydrazonopyrazolones were designed and their structures were confirmed by spectral and elemental analyses. All synthesized compounds were evaluated for their in vitro COXs, 5-LOX inhibition, in vivo analgesic and anti-inflammatory activities. Compounds 5d, 5f and 5i were found to be the most potent COX-2/5-LOX inhibitors with superior COX-2 selectivity index values (SI = 5.29-5.69) to reference standard celecoxib (SI = 3.52). Four compounds; 5b, 5c, 5d and 5f showed excellent anti-inflammatory activity (% edema inhibition = 72.72-54.54%) and perfect ED50 values (ED50 = 0.044-0.104 mmol/kg) relative to celecoxib (ED50 = 0.032 mmol/kg). To explore the most active compounds, ulcerogenic effect on stomach in comparison with indomethacin and celecoxib in addition to histopathological investigations were performed. Compound 5f showed better gastric profile (UI = 2.33) than celecoxib (UI = 3.00). Also, 5f caused 50% increase in thermal pain threshold close to reference drug indomethacin (53.13%). Docking study of all the target compounds into COX-2 and 5-LOX active sites was performed to rational their anti-inflammatory activities. (C) 2018 Elsevier Inc. All rights reserved.