4-(4-ethylphenyl)-2,4-dioxobutanoic acid | 64393-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-ethylphenyl)-2,4-dioxobutanoic acid
• 英文别名: 4-(4-ethyl-phenyl)-2,4-dioxo-butyric acid
• CAS: 64393-82-4
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: XNLKAHGKMATIAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-ethylphenyl)-2,4-dioxobutanoic acid 在 一水合肼 、 溶剂黄146 作用下， 以89%的产率得到3-(4-乙基苯基)-1H-吡唑-5-羧酸
  参考文献：
  名称：

  5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII

  摘要：

  Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.052
• 作为产物：
  描述：

  对乙基苯乙酮 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-(4-ethylphenyl)-2,4-dioxobutanoic acid
  参考文献：
  名称：

  Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase

  摘要：

  alpha,gamma-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the gamma position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.

  DOI：

  10.1021/jm0342109

文献信息

• Synthesis, Intramolecular Cyclization, and Antinociceptive Activity of Substituted 2-[2-(4-Nitrobenzoyl)hydrazinylidene]-4-oxobut-2-enoic Acids
  作者：E. I. Denisova、D. V. Lipin、K. Yu. Parkhoma、I. O. Devyatkin、D. A. Shipilovskikh、S. V. Chashchina、R. R. Makhmudov、N. M. Igidov、S. A. Shipilovskikh

  DOI：10.1134/s1070428021120083

  日期：2021.12

  New substituted 2-[2-(4-nitrobenzoyl)hydrazinylidene]-4-oxobut-2-enoic acids have been synthesized by condensation of 4-nitrobenzohydrazide with 4-aryl-2,4-dioxobutanoic acids, and their intramolecular cyclization in the presence of propionic anhydride afforded the corresponding substituted 3-[2-(4-nitrobenzoyl)hydrazinylidene]furan-2(3H)-ones. The synthesized compounds were evaluated for their antinociceptive

  4-硝基苯甲酰肼与4-芳基-2,4-二氧代丁酸缩合合成新的取代的2-[2-(4-硝基苯甲酰基)亚肼基]-4-氧代丁-2-烯酸，并在分子内环化丙酸酐的存在提供了相应的取代的3-[2-(4-硝基苯甲酰基)亚肼基]呋喃-2(3H)-酮。评价合成的化合物的镇痛活性。
• Synthesis, Intramolecular Cyclization, and Anti-inflammatory Activity of Substituted 2-[2-(4-R-Benzoyl)hydrazinylidene]-4-oxobutanoic Acids
  作者：D. V. Lipin、E. I. Denisova、D. A. Shipilovskikh、R. R. Makhmudov、N. M. Igidov、S. A. Shipilovskikh

  DOI：10.1134/s1070428022120041

  日期：2022.12

  Abstract The substrate scope of the procedure for the synthesis of 2-[2-(4-R-benzoyl)hydrazinylidene]-4-oxobutanoic acids was expanded, and their intramolecular cyclization in the presence of propionic anhydride was studied. The synthesized compounds were evaluated for their anti-inflammatory activity and acute toxicity. Some compounds showed a significant anti-inflammatory activity at a level comparable

  摘要 扩大了2-[2-(4-R-苯甲酰基)亚肼基]-4-氧代丁酸合成过程的底物范围，研究了它们在丙酸酐存在下的分子内环化反应。对合成化合物的抗炎活性和急性毒性进行了评估。一些化合物显示出显着的抗炎活性，其水平相当于或超过医学上使用的参考药物。
• Synthesis, Intramolecular Cyclization, and Analgesic Activity of Substituted 2-[2-(Furancarbonyl)hydrazinylydene]-4-oxobutanoic Acids
  作者：S. N. Igidov、A.Yu. Turyshev、R. R. Makhmudov、D. A. Shipilovskikh、N. M. Igidov、S. A. Shipilovskikh

  DOI：10.1134/s1070363222090067

  日期：2022.9

  proposed for the synthesis of substituted 2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic acids by the reaction of 4-aryl-2,4-dioxobut-2-enoic acids with furan-2-carbohydrazide. It was found that substituted 2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic acids undergo intramolecular cyclization in the presence of propionic anhydride to form the corresponding substituted 2-[2-(furan-2-carbonyl

  摘要 提出了一种由4-aryl-2,4-dioxobut-2-enoic酸与furan-2反应合成取代的2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic酸的方法。 -碳酰肼。发现取代的2-[2-(呋喃-2-羰基)亚肼基]-4-氧代丁酸在丙酸酐存在下发生分子内环化形成相应的取代的2-[2-(呋喃-2-羰基)亚肼基]-4-氧代丁酸。对所得化合物的镇痛活性和急性毒性进行了研究，发现所得化合物具有显着的镇痛活性和低毒性。根据药物毒性分类，生成的取代的2-[2-(呋喃-2-羰基)亚肼基]-4-氧代丁酸和2-[5-芳基-2-氧代呋喃-3(2 H)-亚叉基]furan-2-carbohydrazides属于V类几乎无毒的药物。
• Chemistry of oxalyl derivatives of methyl ketones
  作者：Yu. S. Andreichikov、S. P. Tendryakova、Yu. A. Nalimova、L. A. Voronova

  DOI：10.1007/bf00480663

  日期：1977.6
• 1,3,4,6-tetracarbonyl compounds. 3. synthesis, structural features, and antimicrobial activity of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones
  作者：N. M. Igidov、E. N. Koz'minykh、O. A. Sof'ina、T. M. Shironina、V. O. Koz'minykh

  DOI：10.1007/bf02251994

  日期：1999.11