ethyl 2-((4-nitrophenyl)hydrazono)-3-oxobutanoate

• 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-((4-nitrophenyl)hydrazono)-3-oxobutanoate
• 英文别名: ethyl (2-p-nitrophenylhydrazono)-3-oxobutanoate；ethyl 2-(4-nitrophenyl)hydrazono-3-oxobutyrate；ethyl 2-(2-(4-nitrophenyl)hydrazono)-3-oxobutanoate；AHE-2；2-(4-nitro-phenylhydrazono)-3-oxo-butyric acid ethyl ester；β-Oxo-α-(4-nitro-phenylhydrazono)-buttersaeure-aethylester；2-(4-Nitro-phenylhydrazono)-3-oxo-buttersaeure-aethylester；(4-Nitro-benzolazo)-acetessigsaeure-aethylester；ethyl 2-[(4-nitrophenyl)hydrazinylidene]-3-oxobutanoate
• 化学式: C₁₂H₁₃N₃O₅
• 分子量: 279.252
• InChiKey: MJUWBBVBBZOLSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 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：
  0.25
• 拓扑面积：
  110.9
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((4-nitrophenyl)hydrazono)-3-oxobutanoate 在 溴 、 溶剂黄146 作用下， 生成 ethyl γ-bromo-(4-nitrophenyl)azoacetoacetate
  参考文献：
  名称：

  Chattaway; Ashworth, Journal of the Chemical Society, 1933, p. 478

  摘要：

  DOI：
• 作为产物：
  描述：

  3-oxo-2-(phenylhydrazono)butyric acid ethyl ester 在 硝酸 、 溶剂黄146 作用下， 生成 ethyl 2-((4-nitrophenyl)hydrazono)-3-oxobutanoate
  参考文献：
  名称：

  Buelow; Haas, Chemische Berichte, 1910, vol. 43, p. 2662

  摘要：

  DOI：

文献信息

• Efficient, One-Pot Synthesis of Triazolothiadiazinyl-pyrazolone and Pyrazolyl-triazolothiadiazine Derivatives via Multicomponent Reaction
  作者：Tewodros Birhanu Aychiluhim、Vedula Rajeswar Rao

  DOI：10.1080/00397911.2012.721917

  日期：2014.5.19

  Abstract A one-pot, multicomponent reaction of 3-(2-bromo acetyl)coumarins, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and different derivatives of ethyl 2-(2-(aryl)hydrazono)-3-oxobutanoates provide an efficient and direct method for the synthesis of 4-(arylydrazono)-3-methyl-1-(6-(coumarin-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1H-pyrazol-5(4H)-ones (4a–h). A similar methodology

  摘要 3-(2-溴乙酰基)香豆素、4-氨基-5-肼基-4H-[1,2,4]三唑-3-硫醇和不同的乙基2-( 2-(芳基)腙)-3-氧代丁酸酯为合成4-(芳基腙)-3-甲基-1-(6-(香豆素-3-基)-7H-[1,2]提供了一种有效而直接的方法,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1H-pyrazol-5(4H)-ones (4a–h)。还开发了一种类似的方法来使用乙酰丙酮、4-氨基-5-肼基-4H-[1,2,4]三唑-3-硫醇和苯甲溴化物的不同衍生物合成吡唑基-三唑噻二嗪（9a-f） . 所得产物通过分析和光谱数据表征。图形概要
• Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives
  作者：Moustafa T. Gabr、Nadia S. El-Gohary、Eman R. El-Bendary、Mohamed M. El-Kerdawy、Nanting Ni、Mona I. Shaaban

  DOI：10.1016/j.cclet.2015.09.004

  日期：2015.12

  Abstract New series of benzothiazole derivatives were designed and synthesized. The newly synthesized compounds were screened for their antibacterial activity against Escherichia coli, Staphylococcus aureus and Bacillus cereus. Compounds 6j and 6o showed the highest activity against E. coli and S. aureus. The antifungal activity of these compounds was also tested against Candida albicans and Aspergillus

  摘要设计合成了一系列新的苯并噻唑衍生物。筛选新合成的化合物对大肠杆菌，金黄色葡萄球菌和蜡状芽孢杆菌的抗菌活性。化合物6j和6o显示出对大肠杆菌和金黄色葡萄球菌的最高活性。还测试了这些化合物对白色念珠菌和烟曲霉293的抗真菌活性。化合物4c，4g和6j显示出对白色念珠菌的最高活性。另外，化合物4a和6j显示出对烟曲霉293的有希望的活性。检查了相同的化合物对紫罗兰色杆菌ATCC 12472的抗群体感应活性，而化合物4a，6j和6p显示了中等活性。合成的化合物的体外细胞毒性测试是针对宫颈癌（Hela）和肾成纤维细胞癌（COS-7）细胞系进行的。结果表明，所有测试的化合物对两种细胞系的IC50值均> 50μmol/ L。还评估了化合物4a–c，5a，6g，h，6j，6l，6o和7c，d的分子特性，毒性，药物相似性和药物得分概况。
• Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties
  作者：Udaya Pratap Singh、Hans Raj Bhat、Amita Verma、Mukesh Kumar Kumawat、Rajinder Kaur、S. K. Gupta、Ramendra K. Singh

  DOI：10.1039/c3ra41604f

  日期：——

  A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

  一种新的系列含有吡唑和嘧啶杂合化合物的苯肼酮已被设计，这一设计基于Lipinski五条规则，并通过从不同苯胺的重氮化反应开始，随后与乙酰乙酸、乙基乙酰乙酸和乙基氰乙酸的活性甲基化反应生成肼酮衍生物。目标杂合化合物是在生成的肼酮衍生物与肼、苯肼和尿素环化反应后合成的。这些分子随后在TZM-bl细胞系中进行了抗HIV活性测试。此外，还进行了MTT法以确定活性化合物的细胞毒性。为了说明这些分子的关键结构特征，还对最活跃化合物在HIV-RT蛋白的NNIBP进行了分子对接分析。目标化合物的抗菌活性也针对四种革兰氏阳性菌和四种革兰氏阴性人类病原体进行了检测。所有分子均显示出强效的抗HIV活性以及显著的细菌抑制作用。
• 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