ethyl 2-(2-carboxyphenyl)hydrazono-3-oxobutyrate

• 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: ethyl 2-(2-carboxyphenyl)hydrazono-3-oxobutyrate
• 英文别名: 2-(2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyl)benzoic acid；2-(2-Carboxyphenylhydrazono)-acetessigsaeureaethylester；Acetylglyoxalsaeureethylester-2-carboxyphenylhydrazon；2-(1-ethoxycarbonyl-2-oxo-propylidenehydrazino)-benzoic acid；β-Oxo-α-(2-carboxy-phenylhydrazono)-buttersaeureaethylester；2-(1-Aethoxycarbonyl-2-oxo-propylidenhydrazino)-benzoesaeure；2-[2-(1-ethoxy-1,3-dioxobutan-2-ylidene)hydrazinyl]benzoic acid
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: TVLKRELDODHZPJ-UHFFFAOYSA-N

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：

  ethyl 2-(2-carboxyphenyl)hydrazono-3-oxobutyrate 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 2-[2-(1-(1H-benzo[d]imidazol-2-yl)-2-(2-(2-cyanoacetyl)hydrazono)propylidene)hydrazinyl]benzoic acid
  参考文献：
  名称：

  一些作为潜在抗癌剂的 2-取代苯并咪唑衍生物的合成、表征和生物筛选

  摘要：

  合成、表征和评估了 22 种含有 2-取代苯并咪唑核心的新多环化合物在体外对抗三种最普遍的癌症。七种化合物对乳腺癌、肺癌或中枢神经系统癌细胞系显示出出色的抗肿瘤活性。

  DOI：

  10.3184/174751916x14577069096465
• 作为产物：
  描述：

  o-Carboxybenzenediazonium 、 乙酰乙酸乙酯 在 乙醇 、 sodium acetate 作用下， 生成 ethyl 2-(2-carboxyphenyl)hydrazono-3-oxobutyrate
  参考文献：
  名称：

  Buelow; Schaub, Chemische Berichte, 1908, vol. 41, p. 2365

  摘要：

  DOI：

文献信息

• 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。
• A family of substituted hydrazonoisoxazolones with potential biological properties
  作者：Carlos Bustos、Elies Molins、Juan-Guillermo Cárcamo、Marcelo N. Aguilar、Christian Sánchez、Ignacio Moreno-Villoslada、Hiroyuki Nishide、Ximena Zarate、Eduardo Schott

  DOI：10.1039/c5nj02604k

  日期：——

  activity. The most active isoxazolones were used in reverse transcription polymerase chain reaction (RT-PCR) experiments to determine the effect on the expression levels on mRNA encoding using the anti-apoptotic, Bcl 2, pro-apoptotic, Bax, and the proliferation inhibition, p21WAF-1, proteins. Therefore, it was possible to fully characterize the complete library of 15 isoxazolones and to show that most

  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
• A Facile Synthesis of Aryl-Substituted Hydrazono-Pyrazolyl[1,2,4]triazolo[3,4-<i>b</i>][1,3,4][thiadiazol]-coumarin Derivatives
  作者：Archi Sharma、Gudala Satish、Santhosh Penta

  DOI：10.1002/jhet.2362

  日期：2016.7

  inimitable and therapeutic coumarin‐substituted fused[1,2,4]triazolo‐[3,4‐b][1,3,4]thiadizole derivatives were synthesized by the cyclocondensation reaction of 2‐oxo‐2H‐chromene‐3‐carboxylic acid (1) and 4‐amino‐5‐hydrazinyl‐4H‐[1,2,4]‐triazole‐3‐thiol (2) by using phosphorous oxychloride as a cyclizing agent. This cyclized intermediate 3‐(3‐hydrazino‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazol‐6‐yl)‐chromen‐2‐one

  通过2-氧代-2- H 2-色烯-3的环缩合反应合成了一些不可替代的治疗性香豆素取代的稠合[1,2,4]三唑-[3,4- b ] [1,3,4]噻二唑衍生物。羧酸（1）和4-氨基-5-肼基-4- H- [1,2,4]-三唑-3-硫醇（2），使用三氯氧磷作为环化剂。该环化的中间体3-（3-肼基-[1,2,4]三唑[3,4- b ] [1,3,4]噻二唑-6-基）-铬-2--1（3）之后缩合在NaOAc / MeOH中，在回流条件下，各种2-（2-芳基肼基）-3-氧代丁酸乙酯（4）提供相应的新系列芳基取代的肼基-吡唑基-[1,2,4]三唑并[3,4-b ] [1,3,4] [噻二唑]-香豆素衍生物（5），具有良好的收率。在元素分析，IR，1 H NMR和质谱研究的基础上，建立了新合成化合物的结构。
• New, Convenient, One-Pot Method for the Synthesis of Thiazolyl-pyrazolones from Dehydroacetic Acid Derivative via a Multicomponent Approach
  作者：Santhosh Penta、Rajeswar Rao Vedula

  DOI：10.1080/00397911.2011.558969

  日期：2012.12.1

  Abstract A convenient one-pot method for the synthesis of thiazolyl-pyrazolones was described in excellent yields. Reaction of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one with thiosemicarbazide and ethyl 2-(2-arylhydrazono)-3-oxobutanoates in anhydrous ethanol under reflux conditions afforded the corresponding 4-(2-arylhydrazono)-1-(4-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)thiazol-2-yl)-3

  摘要 描述了一种方便的一锅法合成噻唑基-吡唑啉酮，收率很高。3-(2-溴乙酰基)-4-羟基-6-甲基-2H-吡喃-2-酮与氨基硫脲和2-(2-芳基肼基)-3-氧代丁酸乙酯在回流条件下在无水乙醇中反应得到相应的4 -(2-arylhydrazono)-1-(4-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)thiazol-2-yl)-3-methyl-1H-pyrazol-5( 4H)-一种收率良好。新合成化合物的结构是在元素分析、红外、1H 核磁共振和质谱研究的基础上建立的。图形概要
• 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.