2-(2,4-dinitrophenylhydrazono)-propanoic acid | 790-12-5

• 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: 2-(2,4-dinitrophenylhydrazono)-propanoic acid
• 英文别名: pyruvic acid 2,4-dinitrophenyl hydrazone；2,4-dinitrophenylhydrazone of pyruvic acid；pyruvate-2,4-dinitrophenylhydrazone；2-(2,4-dinitro-phenylhydrazono)-propionic acid；2-(2,4-Dinitro-phenylhydrazono)-propionsaeure；Brenztraubensaeure-(2.4-dinitro-phenylhydrazon)；Pyruvic acid 2,4-dinitrophenylhydrazone；2-[(2,4-dinitrophenyl)hydrazinylidene]propanoic acid
• CAS: 790-12-5
• 化学式: C₉H₈N₄O₆
• 分子量: 268.186
• InChiKey: CVWXLIFTNILJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2,4-dinitrophenylhydrazono)-propanoic acid 在 氯化亚砜 作用下， 生成 2-((Z)-2,4-dinitro-phenylhydrazono)-propionic acid methyl ester
  参考文献：
  名称：

  van Duin, Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 68,71

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-(((2-(p-tolyldiazenyl)phenyl)thio)imino)propanoate 、 2,4-二硝基苯肼盐酸盐 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 以0.04 g的产率得到2-(2,4-dinitrophenylhydrazono)-propanoic acid
  参考文献：
  名称：

  One-Pot Oxidation of Alanine and Its Ethyl Ester with a Mild Oxidant 4′-Methylazobenzene-2-sulfenyl Bromide

  摘要：

  One-pot oxidation of alanine and its ethyl ester with a mild oxidant 4'-methylazobenzene-2-sulfenyl bromide is described. Using a nonreactively water-soluble electrophilic species, 4'-methylazobenzene-2-sulfenyl bromide, with L-alanine and its ethyl ester (in 3:1 molar proportions) in aqueous solution at room temperature, the corresponding sulfenimines are prepared. On hydrolysis in acidic medium at room temperature, these sulfenimines give ethanal and pyruvic acid respectively.

  DOI：

  10.1080/00397911.2010.515361

文献信息

• Oxidation of some α-hydroxy acids by tetraethylammonium chlorochromate: A kinetic and mechanistic study
  作者：Preeti Swami、D. Yajurvedi、P. Mishra、Pradeep K. Sharma

  DOI：10.1002/kin.20466

  日期：2010.1

  kinetic isotope effect (kH/kD = 5.63 at 298 K). The reaction does not exhibit the solvent isotope effect. The reaction is catalyzed by the hydrogen ions. The hydrogen ion dependence has the following form: kobs = a + b[H+]. Oxidation of p‐methylmandelic acid has been studied in 19 different organic solvents. The solvent effect has been analyzed by using Kamlet's and Swain's multiparametric equations. A

  乙醇酸，乳酸，苹果酸和一些取代的扁桃酸在二甲基亚砜中被四乙基氯铬酸铵（TEACC）氧化导致形成相应的含氧酸。该反应在TEACC和羟基酸中均为一级。反应失败，导致丙烯腈聚合。α-氘代扁桃酸的氧化表明存在主要的动力学同位素效应（在298 K时k H / k D = 5.63）。该反应不表现出溶剂同位素效应。该反应由氢离子催化。氢离子依赖性具有以下形式：k obs = a + b [H + ]。p的氧化甲基扁桃酸已经在19种不同的有机溶剂中进行了研究。通过使用Kamlet和Swain的多参数方程分析了溶剂效应。提出了一种涉及通过铬酸酯的氢化物离子转移的机理。©2009 Wiley Periodicals，Inc.国际化学杂志Kinet 42：50-55，2010年
• Biocatalytic Reversal of Advanced Glycation End Product Modification
  作者：Nam Y. Kim、Tyler N. Goddard、Seungjung Sohn、David A. Spiegel、Jason M. Crawford

  DOI：10.1002/cbic.201900158

  日期：2019.9.16

  Advanced glycation end products (AGEs) are a heterogeneous group of molecules that emerge from the condensation of sugars and proteins through the Maillard reaction. Despite a significant number of studies showing strong associations between AGEs and the pathologies of aging-related illnesses, it has been a challenge to establish AGEs as causal agents primarily due to the lack of tools in reversing

  高级糖基化终产物（AGEs）是通过梅拉德反应从糖和蛋白质的缩合中出现的一种异质分子。尽管大量研究表明AGEs与衰老相关疾病的病理之间有很强的联系，但由于缺乏在分子水平上逆转AGE修饰的工具，将AGEs确立为病因一直是一个挑战。在这里，我们显示MnmC，一种参与细菌tRNA修饰途径的酶，能够将AGEs羧乙基赖氨酸（CEL）和羧甲基赖氨酸（CML）还原回其天然赖氨酸结构。结合结构同源性分析，定点诱变和蛋白质结构域解剖研究，我们产生了一种MnmC变体，其游离氨基酸形式对CEL具有改进的催化性能。我们表明，这种酶变异体对CEL修饰的拟肽和已建立为AGEs（RAGE）受体的真正配体的含AGE肽也具有活性。我们的数据表明，MnmC变体是有望发展AGE逆转工具和更好地了解AGE生物学的主要催化剂。
• Novel Substrate Specificity of Designer 3-Isopropylmalate Dehydrogenase Derived from Thermus thermophilus HB8
  作者：Masaaki FUJITA、Hideyuki TAMEGAI、Tadashi EGUCHI、Katsumi KAKINUMA

  DOI：10.1271/bbb.65.2695

  日期：2001.1

  Redesigning of an enzyme for a new catalytic reaction and modified substrate specificity was exploited with 3-isopropylmalate dehydrogenase (IPMDH). Point-mutation on Gly-89, which is not in the catalytic site but near it, was done by changing it to Ala, Ser, Val, and Pro, and all the mutations changed the substrate specificity. The mutant enzymes showed higher catalytic efficiency (kcat/Km) than the native IPMDH when malate was used as a substrate instead of 3-isopropylmalate. More interestingly, an additional insertion of Gly between Gly-89 and Leu-90 significantly altered the substrate-specificity, although the overall catalytic activity was decreased. Particularly, this mutant turned out to efficiently accept D-lactic acid, which was not accepted as a substrate by wild-type IPMDH at all. These results demonstrate the opportunity for creating novel enzymes by modification of amino acid residues that do not directly participate in catalysis, or by insertion of additional residues.

  对酶进行重新设计以适应新的催化反应并修改底物特异性，采用了3-异丙基苹果酸脱氢酶（IPMDH）。通过将Gly-89（不在催化位点但靠近它）突变为Ala、Ser、Val和Pro，进行了点突变，所有突变均改变了底物特异性。当以苹果酸作为底物而不是3-异丙基苹果酸时，突变酶的催化效率（kcat/Km）高于天然IPMDH。更有趣的是，在Gly-89和Leu-90之间额外插入Gly显著改变了底物特异性，尽管整体催化活性下降。特别是，这个突变体有效地接受D-乳酸，而野生型IPMDH根本不接受该底物。这些结果表明，通过修改不直接参与催化的氨基酸残基或插入额外的残基，有机会创造出新型酶。
• Novel Hydrazone Derivatives of 3‐Bromopyruvate: Synthesis, Evaluation of the Cytotoxic Effects, Molecular Docking and ADME Studies
  作者：Farzaneh Beygi、Azar Mostoufi、Ayyub Mojaddami

  DOI：10.1002/cbdv.202100754

  日期：2022.6

  3-BP inhibits hexokinase II (HK II), molecular docking of 3-BP derivatives was carried out using AutoDock 4.2. The binding energies of these derivatives were greater than 3-BP, indicating that they had a higher affinity for HK II. For validation of docking, a 40 ns MD simulation was performed. SwissADME was used to predict pharmacokinetics, drug-likeness, and ADME parameters of the screened compounds

  合成了一系列 3-溴丙酮酸 (3-BP) 衍生物以开发新的有效抗癌剂。使用 FT-IR、 1 H-、13 C-NMR 光谱和元素分析 (CHN)表征化合物的化学结构。研究了它们对四种癌细胞系的细胞毒活性，包括结肠 (SW1116)、乳腺癌 (MDA-MB-231)、肺癌 (A549) 和肝癌 (HepG2) 癌细胞系。在合成的化合物中，与 3-BP 相比， 3b显示出有希望的细胞毒活性，IC 50针对 A549、MDA-MB-231、SW1116 和 HepG2 细胞系的值分别为 16.3 μM、19.1 μM、27.8 μM 和 14.5 μM。此外，研究了这些化合物对 MCF-10A（一种正常的乳腺细胞系）的影响，以确定它们在致瘤细胞和非致瘤细胞之间的选择性。由于 3-BP 抑制己糖激酶 II (HK II)，因此使用 AutoDock 4.2 进行 3-BP 衍生物的分子对接。这些衍
• Role of Ethylenediammonium Dichromate in the Kinetic and Mechanistic Analysis of the Oxidation of Glycolic and Lactic Acids in Aqueous AcOH Medium
  作者：H. Jain、P. Kharetiya、D. Panday

  DOI：10.1007/s10953-023-01359-z

  日期：——

  In aqueous acetic acid medium, the kinetics of oxidation of glycolic and lactic acid by ethylenediammonium dichromate [enH2Cr2O7] have been explored. The oxidation product is the corresponding oxoacid. The conventional UV–vis spectrophotometric method is used to study the reaction kinetics. First-order kinetics has been observed concerning [enH2Cr2O7] and with substrate the order is less than two.

  在乙酸水溶液介质中，研究了重铬酸乙二胺 [enH 2 Cr 2 O 7 ]氧化乙醇酸和乳酸的动力学。氧化产物是相应的含氧酸。传统的紫外可见分光光度法用于研究反应动力学。已观察到关于[enH 2 Cr 2 O 7 ]的一级动力学，并且对于底物，该级数小于二。相对于底物的分数阶依赖性证实了氧化剂和底物在限速步骤之前结合形成复合物。反应速率随着[H + ]浓度的增加而增加。乙醇酸主要动力学同位素效应的存在，在 298K 时k H / k D = 5.97（丙乙醇酸和氘乙醇酸的速率常数之比）表明是 C-H 键断裂而不是 C-C 键断裂。发现溶剂极性的变化对氧化速率有显着影响。根据实验数据，提出了不稳定循环过渡态的形成以及随后的分子内质子转移。在类似条件下研究了乳酸的氧化。

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